Process for producing deuterated aromatic compounds

Abstract

A method for manufacturing a deuterated aromatic compound includes a step of deuterating the aromatic compound in a deuterium-containing solvent. The aromatic compound has a structure in which two or more aromatic rings are bonded together via connecting bonds. At least one of the two or more aromatic rings in the aromatic compound is a fused aromatic ring. The at least one of the fused aromatic rings has an aromatic ring comprising a first fused ring atom having the connecting bonds involved in the bonding with other aromatic rings, and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides. At least one of the second fused ring atom and the third fused ring atom is not an atom constituting a six-membered ring in a ring fused with the aromatic ring comprising the first fused ring atom, the second fused ring atom, and the third fused ring atom.

Description

Technical Field

[0001] This invention relates to a method for manufacturing deuterated aromatic compounds. Background Technology

[0002] Organic electroluminescent devices (hereinafter, sometimes referred to as "organic EL devices") are used in full-color displays such as mobile phones and televisions. When a voltage is applied to an organic EL device, holes are injected from the anode into the emissive layer, and electrons are injected from the cathode into the emissive layer. Then, in the emissive layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%.

[0003] To improve the performance of organic EL devices, various studies have been conducted on the compounds used in organic EL devices. Examples of the performance characteristics of organic EL devices include, for instance, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0004] For example, in Patent Document 1 and Patent Document 2, deuterated compounds and their manufacturing methods are described as compounds used as organic EL elements.

[0005] Patent Document 1 describes a method for deuterating an anthracene compound in which an aryl group is bonded to the carbon atoms at the 9th and 10th positions of an anthracene.

[0006] Patent document 2 describes a method including multiple steps for synthesizing deuterated intermediates and a method for synthesizing deuterated diarylpyrene using multiple deuterated intermediates.

[0007] Existing technical documents

[0008] Patent documents

[0009] Patent Document 1: Korean Patent No. 10-1427457

[0010] Patent Document 2: Korean Patent No. 10-1790854 Summary of the Invention

[0011] The problem that the invention aims to solve

[0012] In the method described in Patent Document 1, the efficiency (deuteration rate) of deuterating protium in the molecule of an aryl-substituted anthracene compound is low.

[0013] To manufacture deuterated diarylpyrene using the method described in Patent Document 2, multiple steps are required, resulting in low manufacturing efficiency.

[0014] The purpose of this invention is to provide a method for manufacturing deuterated aromatic compounds, which can efficiently produce deuterated aromatic compounds with a high deuteration rate.

[0015] Methods for solving problems

[0016] According to one aspect of the present invention, a method for manufacturing a deuterated aromatic compound is provided, comprising a step of deuterating the aromatic compound in a deuterium-containing solvent, wherein the aromatic compound has a structure in which two or more aromatic rings are bonded together via connecting bonds, at least one of the two or more aromatic rings of the aromatic compound is a fused aromatic ring, and the at least one of the fused aromatic rings has an aromatic ring comprising a first fused ring atom having the connecting bonds involved in the bonding with other aromatic rings, and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides, wherein at least one of the second fused ring atom and the third fused ring atom is not an atom constituting a six-membered ring in a ring fused with the aromatic ring comprising the first fused ring atom, the second fused ring atom and the third fused ring atom.

[0017] According to one aspect of the present invention, a method for manufacturing deuterated aromatic compounds can be provided, which can efficiently produce deuterated aromatic compounds with high deuteration rates. Attached Figure Description

[0018] Figure 1 The image shows the 1H NMR spectrum of a deuterated aromatic compound produced by the method described in Example 1.

[0019] Figure 2 The image shows the 1H NMR spectrum of the aromatic compound used in the manufacturing method of Example 1. Detailed Implementation

[0020] The method for manufacturing a deuterated aromatic compound according to this embodiment is a method for manufacturing a deuterated aromatic compound. The method for manufacturing a deuterated aromatic compound according to this embodiment includes a step of deuterating the aromatic compound in a deuterium-containing solvent. The aromatic compound has a structure in which two or more aromatic rings are bonded together via connecting bonds within the molecule. At least one of the two or more aromatic rings in the aromatic compound is a fused aromatic ring. At least one of the fused aromatic rings comprises a first fused ring atom having the connecting bonds involved in bonding with other aromatic rings, and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides. At least one of the second fused ring atom and the third fused ring atom is not an atom constituting a six-membered ring in a ring fused with the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom.

[0021] The aromatic compounds used in the method for manufacturing deuterated aromatic compounds in this embodiment are undeuterated aromatic compounds (sometimes referred to as non-deuterated aromatic compounds).

[0022] In this specification, an aromatic ring refers to a ring with 4n+2 π electrons (n ​​being a positive integer including 0). An aromatic ring is at least one of an aromatic hydrocarbon ring and an aromatic heterocycle.

[0023] The ring fused with an aromatic ring comprising a first fused ring atom, a second fused ring atom, and a third fused ring atom is preferably a five-membered ring, a six-membered ring, a seven-membered ring, or an eight-membered ring, more preferably a five-membered ring or a six-membered ring.

[0024] "At least one of the second fused ring atom and the third fused ring atom is not an atom of a six-membered ring in a ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom and the third fused ring atom" means, for example, as shown in (E1), (E2) or (E3) below.

[0025] (E1) One of the second and third fused ring atoms is an atom that constitutes a six-membered ring fused with an aromatic ring containing the first, second, and third fused ring atoms. The other of the second and third fused ring atoms is not an atom that constitutes a ring other than the aromatic ring containing the first, second, and third fused ring atoms. (The other of the second and third fused ring atoms is only contained in the aromatic ring containing the first, second, and third fused ring atoms.)

[0026] (E2) One of the second fused ring atom and the third fused ring atom is an atom that forms a six-membered ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom and the third fused ring atom, and the other of the second fused ring atom and the third fused ring atom is an atom that forms a five-membered ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom and the third fused ring atom.

[0027] (E3) The second and third fused ring atoms are not atoms that form a ring fused with an aromatic ring containing the first, second, and third fused ring atoms.

[0028] The atoms constituting the ring fused with an aromatic ring containing a first fused ring atom, a second fused ring atom, and a third fused ring atom are carbon atoms or heteroatoms. Examples of heteroatoms include oxygen atoms, sulfur atoms, nitrogen atoms, boron atoms, and phosphorus atoms.

[0029] For example, the following compound BH-A conforms to the aromatic compounds used in the method for manufacturing deuterated aromatic compounds of this embodiment.

[0030] [Chemical Formula 1]

[0031]

[0032] Compound BH-A has four aromatic rings (two benzene rings and two pyrene rings) within its molecule. Compound BH-A has a structure in which the four aromatic rings are bonded via connecting bonds (single bonds). Of the four aromatic rings in compound BH-A, two are fused aromatic rings (pyrene rings). As shown in the structural formula below, the pyrene rings in compound BH-A have an aromatic ring A1, which comprises a first fused ring atom C1 having a connecting bond involved in the bonding with the other aromatic ring B1 (benzene ring), and atoms flanking the first fused ring atom C1. 相 The adjacent second fused ring atom C2 and the third fused ring atom C3.

[0033] [Chemical Formula 2]

[0034]

[0035] In compound BH-A, the second fused ring atom C2 is not an atom that forms a six-membered ring, i.e., ring A2, which is fused with the aromatic ring A1 containing the first fused ring atom C1, the second fused ring atom C2, and the third fused ring atom C3. The third fused ring atom C3 is an atom that forms ring A2, which is fused with the aromatic ring A1. The second fused ring atom C2 and the third fused ring atom C3 of the aromatic ring A1 in compound BH-A correspond to the situation described in (E1) above.

[0036] For example, the following compound Ref-BH-A does not conform to the aromatic compounds used in the method for manufacturing deuterated aromatic compounds of this embodiment.

[0037] [Chemical Formula 3]

[0038]

[0039] Compound Ref-BH-A has three aromatic rings (one benzene ring, one anthracene ring, and one dibenzofuran ring) within its molecule. Compound Ref-BH-A has a structure in which the three aromatic rings are linked by connecting bonds (single bonds). Of the three aromatic rings in compound Ref-BH-A, two are fused aromatic rings (anthracene ring and a dibenzofuran ring). As shown in the structural formula below, the anthracene ring in compound Ref-BH-A has an aromatic ring A1, which comprises a first fused ring atom C1 having a connecting bond involved in the bonding with the other aromatic ring B1 (benzene ring), and a second fused ring atom C2 and a third fused ring atom C3 adjacent to the first fused ring atom C1 on both sides. Aromatic ring A1 also comprises a first fused ring atom C4 having a connecting bond involved in the bonding with the other aromatic ring (dibenzofuran ring), and a second fused ring atom C5 and a third fused ring atom C6 adjacent to the first fused ring atom C4 on both sides. The first fused ring atom C4 is bonded to an aromatic ring D1 that constitutes the dibenzofuran ring, which is another aromatic ring, via a linking bond.

[0040] [Chemical Formula 4]

[0041]

[0042] In compound Ref-BH-A, the second fused ring atoms C2 and C5 are atoms that constitute the six-membered ring A2, which is fused with the aromatic ring A1. Furthermore, in compound Ref-BH-A, the third fused ring atoms C3 and C6 are atoms that constitute the six-membered ring A3, which is fused with the aromatic ring A1. Thus, in compound Ref-BH-A, the second fused ring atoms C2 and C5, and the third fused ring atoms C3 and C6, are all atoms that constitute either ring A2 or ring A3, which is fused with the aromatic ring A1. Therefore, compound Ref-BH-A does not conform to the aromatic compound used in the method for manufacturing the deuterated aromatic compound of this embodiment.

[0043] If, as in compound Ref-BH-A, the second and third fused ring atoms are atoms that constitute ring A2 or ring A3 fused with aromatic ring A1, then the hydrogen atoms bonded to the carbon atoms near the second and third fused ring atoms of ring A2 or ring A3 and the hydrogen atoms bonded to aromatic ring B1 or aromatic ring D1 are close to each other, creating large sites in the molecule. Hydrogen atoms located in such large sites are not easily deuterated.

[0044] In the method for manufacturing deuterated aromatic compounds according to this embodiment, at least one of the fused aromatic rings is preferably a fused aromatic ring having three or more rings fused together.

[0045] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the fused aromatic ring is preferably a fused aromatic hydrocarbon ring with 10 or more and 30 or less carbon atoms or a fused aromatic heterocycle with 9 or more and 30 or less carbon atoms.

[0046] In the method for producing deuterated aromatic compounds according to this embodiment, at least one of the fused aromatic rings is preferably selected from pyrene ring, fluoranthene ring, benzo[a]fluoranthene ring, phenanthrene ring, benzo[a]phenanthrene ring, etc. cyclohexane, benzo[a] The ring is selected from at least one of the following: triphenylene ring, benzotriphenylene ring, benzoxanthine ring, anthracene ring (wherein the carbon atom at least one of the positions 1 to 8 of the anthracene ring has the aforementioned connecting bond), and benzo[a]anthracene ring (wherein the carbon atom at least one of the positions 1 to 6 and 8 to 11 of the benzo[a]anthracene ring has the aforementioned connecting bond).

[0047] In the method for manufacturing deuterated aromatic compounds according to this embodiment, at least one of the fused aromatic rings is preferably selected from at least any one of the rings shown in the following formulas (101) to (148).

[0048] [Chemical Formula 5]

[0049]

[0050] [Chemical Formula 6]

[0051]

[0052] [Chemical Formula 7]

[0053]

[0054] [Chemical Formula 8]

[0055]

[0056] (In the above formulas (101) to (148), * represents the bonding position of the above-mentioned connecting bond in the aromatic compound with other aromatic rings.)

[0057] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the fused aromatic ring preferably does not contain the rings shown in the following formulas (X1), (X2), (X3) and (X4).

[0058] [Chemical Formula 9]

[0059]

[0060] (In the above formulas (X1), (X2), (X3), and (X4), * represents the bonding position of the above-mentioned linking bond in the aromatic compound with other aromatic rings.)

[0061] For example, in the fused ring shown in the above formula (102), the second and third fused ring atoms of the aromatic ring bonded with the connecting bond are equivalent to the case (E3) above.

[0062] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the aromatic compound has two or more fused aromatic rings. Preferably, each of these two or more fused aromatic rings has an aromatic ring comprising a first fused ring atom, a second fused ring atom, and a third fused ring atom, corresponding to any of the cases (E1), (E2), or (E3) described above. More preferably, it has an aromatic ring comprising a first fused ring atom, a second fused ring atom, and a third fused ring atom, corresponding to any of the cases (E1) or (E3) described above. In one embodiment, the two or more fused aromatic rings have identical structures. In another embodiment, the two or more fused aromatic rings have different structures. It should be noted that "identical structure" means that the ring skeletons of the two or more fused aromatic rings are identical, and the positions of the connecting bonds are identical.

[0063] In the method for manufacturing deuterated aromatic compounds according to this embodiment, when the aromatic compound has multiple fused aromatic rings, it is preferable that each of these multiple fused aromatic rings has an aromatic ring, which includes a first fused ring atom having a connecting bond involved in bonding with other aromatic rings, and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides, wherein at least one of the second fused ring atom and the third fused ring atom is not an atom constituting a six-membered ring in a ring fused with the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom.

[0064] In the method for manufacturing deuterated aromatic compounds according to this embodiment, when the aromatic compound has multiple fused aromatic rings, these multiple fused aromatic rings are preferably selected from at least one of the rings shown in the above formulas (101) to (148).

[0065] The aromatic compound used in the method for manufacturing the deuterated aromatic compound of this embodiment may have two or more rings selected from the rings shown in formulas (101) to (148) above. The two or more rings selected from the rings shown in formulas (101) to (148) above may be the same as or different from each other.

[0066] The aromatic compound used in the method for manufacturing the deuterated aromatic compound of this embodiment is preferably composed of a first fused ring atom, a second fused ring atom, and a third fused ring atom in the fused aromatic ring, which is equivalent to any one of the cases (E1), (E2), and (E3) described above. It is also preferable to have multiple groups of first fused ring atoms, second fused ring atoms, and third fused ring atoms that are equivalent to any one of the cases (E1) and (E3) described above.

[0067] The fused aromatic ring in the aromatic compound used in the method for producing the deuterated aromatic compound of this embodiment may have multiple bonds connecting it to other aromatic rings. Preferably, the first fused ring atom having these bonds is adjacent to the second and third fused ring atoms on both sides, and at least one of the second and third fused ring atoms is not an atom constituting a ring fused with the aromatic ring containing the first, second, and third fused ring atoms.

[0068] For example, as an alternative to the fused aromatic ring shown in the above formula (101) having a connecting bond, the fused aromatic ring shown in the following formula (149) can be cited.

[0069] [Chemical Formula 10]

[0070]

[0071] The fused aromatic ring shown in formula (149) above comprises aromatic ring A11 and aromatic ring A13, wherein aromatic ring A11 contains a first fused ring atom C having a connecting bond involved in the bonding with other aromatic rings. 11 and on both sides with the first fused ring atom C 11 The adjacent second fused ring atom C 12 and the third fused ring atom C 13 The aromatic ring A13 contains a first fused ring atom C having a connecting bond involved in bonding with other aromatic rings. 14 and on both sides with the first fused ring atom C 14 The adjacent second fused ring atom C 15 and the third fused ring atom C 16 .

[0072] In the fused aromatic ring shown in formula (149) above, the second fused ring atom C 12 The third fused ring atom C is not one of the atoms that constitutes the rings A12 and A14 fused with the aromatic ring A11. 13 These are the atoms that make up the ring A12, which is fused with the aromatic ring A11.

[0073] In the fused aromatic ring shown in formula (149) above, the second fused ring atom C 15The third fused ring atom C is not one of the atoms that constitutes the rings A12 and A14 fused with the aromatic ring A13. 16 These are atoms that constitute ring A14, which is fused with aromatic ring A13.

[0074] The aromatic compound used in the method for producing the deuterated aromatic compound of this embodiment preferably does not have an anthracene ring.

[0075] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the deuterium-containing solvent preferably contains deuterium in the solvent molecule. The deuterium-containing solvent preferably contains at least one solvent selected from hexadeuterated benzene (benzene-d6, C6D6), heavy water (D2O), benzene-d4 (C6D4H2), and octadeuterated toluene (toluene-d8, CD3C6D5), and more preferably hexadeuterated benzene (C6D6) or heavy water (D2O).

[0076] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the amount of deuterium-containing solvent used is defined as 1 mL of deuterium-containing solvent relative to 1 g of aromatic compound (protium). The amount of deuterium-containing solvent used is, for example, 5 (v / w) or more and 10,000 (v / w) or less, preferably 10 (v / w) or more and 1,000 (v / w) or less, and more preferably 50 (v / w) or more and 500 (v / w) or less.

[0077] In the method for producing deuterated aromatic compounds according to this embodiment, in the step of deuterating the aromatic compound in a deuterium-containing solvent, it is preferable to use at least one catalyst capable of exchanging protium for deuterium, for example, a Lewis acid H / D exchange catalyst is also preferred.

[0078] In the method for manufacturing deuterated aromatic compounds according to this embodiment, in the step of deuterating the aromatic compound in a deuterium-containing solvent, it is preferable to use at least one catalyst selected from aluminum catalyst, platinum catalyst and palladium catalyst.

[0079] Examples of aluminum catalysts include aluminum trichloride and ethyl aluminum chloride.

[0080] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the amount of aluminum catalyst used relative to the aromatic compound (protium) is, for example, 0.1 molar equivalents or more and 20 molar equivalents or less, preferably 0.5 molar equivalents or more and 10 molar equivalents or less, and more preferably 1 molar equivalents or more and 5 molar equivalents or less.

[0081] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the reaction temperature of the step of deuterating the aromatic compound in a deuterated solvent is, for example, 0°C or higher and the boiling point of the deuterated solvent used in this step is below, preferably 20°C or higher and the boiling point of the deuterated solvent is below, more preferably 40°C or higher and the temperature is below -10°C relative to the boiling point of the deuterated solvent. "The temperature is below -10°C relative to the boiling point of the deuterated solvent" means, for example, when the deuterated solvent is heavy water (boiling point: 101.4°C), 101.4 - 10 = 91.4°C.

[0082] In the method for manufacturing deuterated aromatic compounds according to this embodiment, the step of deuterating the aromatic compound in a deuterium-containing solvent preferably further includes: a step of dissolving the aromatic compound (protium gas) as a reactant in a deuterium-containing solvent to obtain a solution, and a step of adding a catalyst to the solution to cause the reaction. The catalyst is a catalyst capable of exchanging protium for deuterium, and preferably at least one catalyst selected from aluminum catalysts, platinum catalysts, and palladium catalysts.

[0083] In addition, in the process of deuterating an aromatic compound in a deuterium-containing solvent, for example, the aromatic compound and a mixed catalyst composed of a palladium catalyst and a platinum catalyst (mass ratio 1:1) in an amount of 0.01% to 200% by mass relative to the total mass of the aromatic compound (the total amount of palladium metal and platinum metal relative to the total mass of the aromatic compound is 0.0005% to 20% by mass relative to the total mass of the aromatic compound) are added to the solvent to be deuterated (an amount of 1 equivalent to 1 equivalent to 20,000 equivalents or less, preferably 10 equivalents to 700 equivalents or less relative to 1 equivalent of the mixed catalyst), the reaction system is sealed, the system is replaced with hydrogen, and the reaction is carried out in an oil bath at a temperature of about 20°C to 200°C for about 30 minutes to 100 hours with stirring.

[0084] The deuteration rate of the deuterated aromatic compound produced by the method for producing deuterated aromatic compounds according to this embodiment is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.

[0085] The deuteration rate of deuterated aromatic compounds can be determined by NMR analysis.

[0086] (Specific examples of aromatic compounds)

[0087] In the method for manufacturing deuterated aromatic compounds according to this embodiment, specific examples of the aromatic compounds used include the following compounds, as well as compounds obtained by replacing deuterium (D) with protium (H) in the specific examples of deuterated aromatic compounds described later. However, the present invention is not limited to these specific examples of aromatic compounds.

[0088] [Chemical Formula 11]

[0089]

[0090] (Specific examples of deuterated aromatic compounds)

[0091] Specific examples of deuterated aromatic compounds produced by the method for producing deuterated aromatic compounds according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples of deuterated aromatic compounds.

[0092] [Chemical Formula 12]

[0093]

[0094] [Chemical Formula 13]

[0095]

[0096] [Chemical Formula 14]

[0097]

[0098] [Chemical Formula 15]

[0099]

[0100] [Chemical Formula 16]

[0101]

[0102] [Chemical Formula 17]

[0103]

[0104] [Chemical Formula 18]

[0105]

[0106] [Chemical Formula 19]

[0107]

[0108] [Chemical Formula 20]

[0109]

[0110] [Chemical Formula 21]

[0111]

[0112] [Chemical Formula 22]

[0113]

[0114] [Chemical Formula 23]

[0115]

[0116] [Chemical Formula 24]

[0117]

[0118] According to the method for manufacturing deuterated aromatic compounds of this embodiment, protium in the molecule of an aromatic compound having a defined fused polycyclic skeleton can be effectively deuterated.

[0119] Conventional methods for deuterating protium in the molecules of aromatic compounds require steps of synthesizing intermediates that deuterate the aromatic rings constituting the aromatic compounds individually, and using the deuterated intermediates to synthesize compounds in which protium is deuterated.

[0120] The method for manufacturing deuterated aromatic compounds in this embodiment involves a step of deuterating an aromatic compound (protium) having the same skeleton as the deuterium to be manufactured in a deuterated solvent. This step allows for the deuteration of protium in the molecule of the aromatic compound. Therefore, compared with conventional methods, the manufacturing method has fewer steps and can be manufactured efficiently.

[0121] Furthermore, although the deuteration rate is low in the method of deuterating aromatic compounds having 9,10-anthracene dimethyl as a fused polycyclic skeleton, the method for producing deuterated aromatic compounds according to this embodiment can produce deuterated aromatic compounds with a higher deuteration rate.

[0122] The deuterated aromatic compounds produced by the method for producing deuterated aromatic compounds according to this embodiment can be used as materials for various purposes, such as as materials for organic electroluminescent elements.

[0123] Organic electroluminescent devices (sometimes called organic EL devices) have an organic layer between two electrodes, an anode and a cathode. This organic layer comprises at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further comprise inorganic compounds. In an organic EL device, at least one of the organic layers is a light-emitting layer. Therefore, the organic layer may, for example, consist of a single light-emitting layer, or it may comprise layers that can be used in an organic EL device. The layers that can be used in an organic EL device are not particularly limited, and examples include at least one layer selected from hole injection layers, hole transport layers, electron blocking layers, electron injection layers, electron transport layers, and hole blocking layers.

[0124] The organic layer of the organic EL element is preferably composed of any of the following layers.

[0125] Electron blocking layer / light-emitting layer / hole blocking layer

[0126] Hole injection layer / electron blocking layer / light-emitting layer / hole blocking layer

[0127] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer

[0128] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer

[0129] Electron blocking layer / light-emitting layer / hole blocking layer / electron injection layer

[0130] Electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer

[0131] Electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0132] Hole injection layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection layer

[0133] Hole injection layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer

[0134] Hole injection layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0135] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection layer

[0136] Hole transport layer / electron blocking layer / luminescent layer / hole blocking layer / electron transport layer

[0137] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0138] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron injection layer

[0139] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron transport layer

[0140] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron transport layer / electron injection layer

[0141] The deuterated aromatic compound manufactured by the method of this embodiment is preferably contained in the organic layer of at least one of the organic EL elements. The deuterated aromatic compound may be contained in multiple layers.

[0142] Deuterated aromatic compounds can be contained alone in a layer or together with at least one other compound. Other compounds contained in a layer together with deuterated aromatic compounds can be either undeuterated (sometimes called non-deuterated compounds) or deuterated compounds.

[0143] It should be noted that the present invention is not limited to the embodiments described above. Modifications and improvements made within the scope of achieving the objectives of the present invention are included in the present invention. For example, the specific materials, reaction conditions, structures, shapes, etc., in the implementation of the present invention can be modified and improved within the scope of achieving the objectives of the present invention.

[0144] Example

[0145] The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[0146] <Compound Manufacturing>

[0147] (Example 1)

[0148] Example 1 relates to a method for producing compound BH-1, which is a deuterated aromatic compound. The synthetic route of compound BH-1 is shown below.

[0149] [Chemical Formula 25]

[0150]

[0151] (1) Synthesis of deuterium (compound BH-1)

[0152] Under an argon atmosphere, 19.0 g of protium (compound BH-A), a non-deuterated aromatic compound, and 1140 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 4.6 g of aluminum chloride. The mixture was heated and stirred at 40 °C for 29 hours. After cooling to room temperature, 300 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography and then recrystallized using a mixed solvent of toluene and hexane to obtain 15.3 g of an orange solid (yield: 77%). Mass spectrometry analysis of the orange solid revealed it to be compound BH-1, a deuterated aromatic compound, with a molecular weight of 580.85 and an m / e ratio of 581.

[0153] [Calculation of the deuteration rate of the deuterium (compound BH-1)]

[0154] The protium of the standard (compound BH-A, molecular weight: 554.69) was determined by NMR in deuterated tetrahydrofuran at a concentration of 10.2 mg (0.0184 mmol). Figure 2 The aromatic compound (compound BH-A) used in the manufacturing method of Example 1. 1 HNMR spectrum. With dibromomethane as the reference and set to 100, the total integral value of protons in the molecule is 13259.62, and the number of protons in one molecule is 26.

[0155] On the other hand, 9.9 mg (0.0170 mmol) of the deuterium (compound BH-1, molecular weight: 580.85) was also determined by NMR in deuterated tetrahydrofuran. Figure 1 The deuterated aromatic compound (compound BH-1) was manufactured using the method described in Example 1. 1 ¹H NMR spectrum. With dibromomethane as the reference value and set to 100, the total integral value of protons in the molecule is 802.61. Considering the molar ratio of protium to deuterium, the total integral value of incompletely deuterated protons in the deuterium is 802.61 × (0.0184 / 0.0170) = 868.71. Based on the total integral values ​​of protons in the deuterium and protium, the deuteration rate is 93.4%, as shown in the following formula.

[0156] {1-(868.71 / 13259.62)}×100=93.4%

[0157] The manufacturing method of Example 1 can efficiently produce deuterated aromatic compounds (compound BH-1) with high deuteration rates because it uses an aromatic compound (compound BH-A) with a specified ring structure.

[0158] (Example 2)

[0159] Example 2 relates to a method for producing compound BH-2, which is a deuterated aromatic compound. The synthetic route of compound BH-2 is shown below.

[0160] [Chemical Formula 26]

[0161]

[0162] (2) Synthesis of deuterium (compound BH-2)

[0163] Under an argon atmosphere, 10.0 g of protium (compound BH-B), a non-deuterated aromatic compound, and 1200 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 50 °C to dissolve the reactants, followed by the addition of 3.5 g of aluminum chloride. The mixture was heated and stirred at 60 °C for 40 hours. After cooling to room temperature, 500 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 7.2 g of a pale yellow solid (yield: 69%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-2, a deuterated aromatic compound, with a molecular weight of 420.61 and an m / e ratio of 421.

[0164] (Example 3)

[0165] Example 3 relates to a method for producing compound BH-3, which is a deuterated aromatic compound. The synthetic route of compound BH-3 is shown below.

[0166] [Chemical Formula 27]

[0167]

[0168] (3) Synthesis of deuterium (compound BH-3)

[0169] Under a nitrogen atmosphere, 5.0 g of protium (compound BH-C), a non-deuterated aromatic compound, and 800 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 2.2 g of aluminum chloride. The mixture was heated and stirred at 40 °C for 30 hours. After cooling to room temperature, 300 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, filtered, and the precipitated solid was collected. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 2.9 g of a pale yellow solid (yield: 55%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-3, a deuterated aromatic compound, with a molecular weight of 648.92 and an m / e ratio of 649.

[0170] (Example 4)

[0171] Example 4 relates to a method for producing compound BH-4, which is a deuterated aromatic compound. The synthetic route of compound BH-4 is shown below.

[0172] [Chemical Formula 28]

[0173]

[0174] (4) Synthesis of deuterium (compound BH-4)

[0175] Under an argon atmosphere, 8.0 g of protium (compound BH-D), a non-deuterated aromatic compound, and 900 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 2.7 g of aluminum chloride. The mixture was heated and stirred at 40 °C for 50 hours. After cooling to room temperature, 300 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 6.5 g of a pale yellow solid (yield: 77%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-4, a deuterated aromatic compound, with a molecular weight of 468.72 and an m / e ratio of 469.

[0176] (Example 5)

[0177] Example 5 relates to a method for producing compound BH-5, which is a deuterated aromatic compound. The synthetic route of compound BH-5 is shown below.

[0178] [Chemical Formula 29]

[0179]

[0180] (5) Synthesis of deuterium (compound BH-5)

[0181] Under an argon atmosphere, 7.5 g of protium (compound BH-E), a non-deuterated aromatic compound, and 1000 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 2.2 g of aluminum chloride. The mixture was heated and stirred at 40 °C for 40 hours. After cooling to room temperature, 300 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 6.2 g of a pale yellow solid (yield: 78%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-5, a deuterated aromatic compound, with a molecular weight of 468.72 and an m / e ratio of 469.

[0182] (Example 6)

[0183] Example 6 relates to a method for producing compound BH-6, which is a deuterated aromatic compound. The synthetic route of compound BH-6 is shown below.

[0184] [Chemical Formula 30]

[0185]

[0186] (6) Synthesis of deuterium (compound BH-6)

[0187] Under an argon atmosphere, 2.5 g of protium (compound BH-F), a non-deuterated aromatic compound, and 500 mL of deuterated toluene (CD3C6H5) were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 2.1 g of aluminum chloride. The mixture was heated and stirred at 70 °C for 65 hours. After cooling to room temperature, 150 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 1.8 g of a pale yellow solid (yield: 69%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-6, a deuterated aromatic compound, with a molecular weight of 500.73 and m / e = 501.

[0188] (Example 7)

[0189] Example 7 relates to a method for producing compound BH-7, a deuterated aromatic compound. The synthetic route for compound BH-7 is shown below.

[0190] [Chemical Formula 31]

[0191]

[0192] (7) Synthesis of deuterium (compound BH-7)

[0193] Under an argon atmosphere, 5.0 g of protium (compound BH-G), a non-deuterated aromatic compound, and 1200 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 2.4 g of aluminum chloride. The mixture was heated and stirred at 40 °C for 35 hours. After cooling to room temperature, 500 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, filtered, and the precipitated solid was collected. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 3.9 g of a pale yellow solid (yield: 75%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-7, a deuterated aromatic compound, with a molecular weight of 596.85 and an m / e ratio of 597.

[0194] (Example 8)

[0195] Example 8 relates to a method for producing compound BH-8, which is a deuterated aromatic compound. The synthetic route of compound BH-8 is shown below.

[0196] [Chemical Formula 32]

[0197]

[0198] (8) Synthesis of deuterium (compound BH-8)

[0199] Under an argon atmosphere, 5.0 g of protium (compound BH-H), a non-deuterated aromatic compound, and 1500 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 45 °C to dissolve the reactants, followed by the addition of 4.2 g of aluminum chloride. The mixture was heated and stirred at 50 °C for 55 hours. After cooling to room temperature, 500 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, and the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized from a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 2.1 g of a pale yellow solid (yield: 67%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-8, a deuterated aromatic compound, with a molecular weight of 500.73 and m / e = 501.

[0200] (Example 9)

[0201] Example 9 relates to a method for producing compound BH-9, which is a deuterated aromatic compound. The synthetic route of compound BH-9 is shown below.

[0202] [Chemical Formula 33]

[0203]

[0204] (9) Synthesis of deuterium (compound BH-9)

[0205] Under an argon atmosphere, 4.0 g of protium (compound BH-J), a non-deuterated aromatic compound, and 2000 mL of hexadeuterated benzene d6 were added to a flask. The mixture was heated to 50 °C to dissolve the reactants, followed by the addition of 2.8 g of aluminum chloride. The mixture was heated and stirred at 60 °C for 48 hours. After cooling to room temperature, 500 mL of heavy water was added dropwise, and the organic layer was separated. The organic layer was concentrated, filtered, and the precipitated solid was collected. The obtained solid was washed with water and acetone. The washed solid was purified by silica gel column chromatography, recrystallized with a mixed solvent of toluene and hexane, and washed with ethyl acetate to obtain 2.4 g of a pale yellow solid (yield: 57%). Mass spectrometry analysis of the pale yellow solid revealed it to be compound BH-9, a deuterated aromatic compound, with a molecular weight of 604.87 and an m / e ratio of 605.

Claims

1. A method for manufacturing deuterated aromatic compounds, It includes the process of deuterating aromatic compounds in a deuterium-containing solvent. The aromatic compound has a structure consisting of two or more aromatic rings bonded together by connecting bonds. The aromatic compound has two or more aromatic rings, two or more of which are fused aromatic rings. The fused aromatic ring is a fused aromatic hydrocarbon ring with 10 or more but less than 30 carbon atoms, or a fused aromatic heterocycle with 9 or more but less than 30 carbon atoms. At least one of the fused aromatic rings has an aromatic ring comprising a first fused ring atom having the connecting bond involved in the bonding with other aromatic rings, and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides. At least one of the second fused-ring atom and the third fused-ring atom is not an atom of a six-membered ring in a ring fused with an aromatic ring containing the first fused-ring atom, the second fused-ring atom, and the third fused-ring atom. At least one of the fused aromatic rings is selected from... pyrene ring, fluoranthene rings, Benzofluoranthene ring, Philippine Ring, Benzenephenanthrene ring, Ring, Benzenecyclohexane, Sanya benzene ring, Benzotriane ring, At least one ring of benzo[a]anthracene ring, and benzo[a]anthracene ring. wherein The carbon atom at positions 1-6 and 8-11 of the benzo[a]anthracene ring has the connecting bond. The aromatic compound does not have an anthracene ring. The deuteration rate of the deuterated aromatic compound is above 70%.

2. The method for producing a deuterated aromatic compound according to claim 1, wherein, The deuterium-containing solvent contains deuterium in its solvent molecules.

3. The method for producing the deuterated aromatic compound according to claim 1 or 2, wherein, The deuterium-containing solvent comprises at least one solvent selected from hexadeuterated benzene (benzene-d6, C6D6), heavy water (D2O), benzene-d4 (C6D4H2), and octadeuterated toluene (toluene-d8, CD3C6D5).

4. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The deuterium-containing solvent is hexadeuterated benzene or heavy water.

5. The method for producing the deuterated aromatic compound according to claim 1 or 2, wherein, The ring fused with the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom is a five-membered ring, a six-membered ring, a seven-membered ring, or an eight-membered ring.

6. The method for producing the deuterated aromatic compound according to claim 1 or 2, wherein, The ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom is a five-membered ring or a six-membered ring.

7. The method for producing the deuterated aromatic compound according to claim 1 or 2, wherein, The atoms constituting the ring fused with the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom are carbon atoms or heteroatoms.

8. The method for producing the deuterated aromatic compound according to claim 7, wherein, The heteroatoms are selected from the group consisting of oxygen atoms, sulfur atoms, nitrogen atoms, boron atoms, and phosphorus atoms.

9. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The second fused ring atom and the third fused ring atom satisfy the following (E1), (E2) or (E3). (E1) One of the second fused-ring atoms and the third fused-ring atom is an atom constituting a six-membered ring fused with an aromatic ring comprising the first fused-ring atom, the second fused-ring atom, and the third fused-ring atom. The other of the second fused ring atom and the third fused ring atom is not an atom that constitutes a ring other than the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom, but is only included in the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom; (E2) One of the second fused-ring atom and the third fused-ring atom is an atom that constitutes a six-membered ring fused with an aromatic ring containing the first fused-ring atom, the second fused-ring atom and the third fused-ring atom, and the other of the second fused-ring atom and the third fused-ring atom is an atom that constitutes a five-membered ring fused with an aromatic ring containing the first fused-ring atom, the second fused-ring atom and the third fused-ring atom; (E3) The second fused ring atom and the third fused ring atom are not atoms that constitute a ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom and the third fused ring atom.

10. The method for producing a deuterated aromatic compound according to claim 9, wherein, Each of the fused aromatic rings has an aromatic ring comprising the first fused ring atom, the second fused ring atom, and the third fused ring atom, corresponding to any of the cases (E1), (E2), or (E3).

11. The method for producing a deuterated aromatic compound according to claim 9, wherein, Each of the fused aromatic rings has an aromatic ring comprising the first fused ring atom, the second fused ring atom, and the third fused ring atom, corresponding to either (E1) or (E3).

12. The method for producing a deuterated aromatic compound according to claim 9, wherein, The aromatic compound has multiple groups in the fused aromatic ring that correspond to any one of the cases (E1), (E2), and (E3), consisting of the first fused ring atom, the second fused ring atom, and the third fused ring atom.

13. The method for producing the deuterated aromatic compound according to claim 9, wherein, The aromatic compound has multiple groups in the fused aromatic ring that correspond to either (E1) or (E3), consisting of the first fused ring atom, the second fused ring atom, and the third fused ring atom.

14. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, Two or more of the fused aromatic rings have the same structure as each other.

15. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, Two or more of the fused aromatic rings have different structures from each other.

16. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, Each of the fused aromatic rings has an aromatic ring comprising the first fused ring atom, the second fused ring atom, and the third fused ring atom, wherein at least one of the second fused ring atom and the third fused ring atom is not an atom of a six-membered ring in a ring fused with the aromatic ring comprising the first fused ring atom, the second fused ring atom, and the third fused ring atom.

17. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, At least one of the fused aromatic rings is selected from... pyrene ring, fluoranthene rings, At least one of the rings selected from benzo[fluoranthracene] and benzo[xanthonium] rings.

18. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, At least one of the fused aromatic rings is selected from at least one ring chosen from the rings shown in formulas (101) to (122) and (125) to (148) below. In formulas (101) to (122) and (125) to (148), * represents the bonding position of the connecting bond in the aromatic compound with other aromatic rings.

19. The method for producing a deuterated aromatic compound according to claim 18, wherein, The fused aromatic rings are all selected from the rings shown in formulas (101) to (122) and (125) to (148).

20. The method for producing a deuterated aromatic compound according to claim 18, wherein, At least one of the fused aromatic rings is selected from at least one of the rings shown in formulas (107) to (111), (116) to (121), (125) to (133) and (138) to (148).

21. The method for producing a deuterated aromatic compound according to claim 18, wherein, The aromatic compound has two or more rings selected from the rings shown in formulas (101) to (122) and (125) to (148), wherein the two or more rings selected from the rings shown in formulas (101) to (122) and (125) to (148) are the same as or different from each other.

22. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The fused aromatic ring does not contain the rings shown in formulas (X1), (X2), (X3), and (X4) below. In formulas (X1), (X2), (X3), and (X4), * represents the bonding position of the connecting bond in the aromatic compound with other aromatic rings.

23. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, In the process of deuterating the aromatic compound in the deuterium-containing solvent, at least one catalyst capable of exchanging protium for deuterium is used.

24. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, In the process of deuterating the aromatic compound in the deuterium-containing solvent, a Lewis acid H / D exchange catalyst is used.

25. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, In the process of deuterating the aromatic compound in the deuterium-containing solvent, at least one catalyst selected from aluminum catalysts, platinum catalysts, and palladium catalysts is used.

26. The method for producing a deuterated aromatic compound according to claim 25, wherein, The aluminum catalyst is aluminum trichloride and ethyl aluminum chloride.

27. The method for producing a deuterated aromatic compound according to claim 25, wherein, The amount of the aluminum catalyst used is more than 0.1 molar equivalents and less than 20 molar equivalents relative to the aromatic compound.

28. The method for producing a deuterated aromatic compound according to claim 25, wherein, The amount of the aluminum catalyst used is more than 0.5 molar equivalents and less than 10 molar equivalents relative to the aromatic compound.

29. The method for producing a deuterated aromatic compound according to claim 25, wherein, The amount of aluminum catalyst used is more than 1 molar equivalent and less than 5 molar equivalent relative to the aromatic compound.

30. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The aromatic compounds are undeuterated aromatic compounds.

31. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The fused aromatic ring in the aromatic compound has multiple bonds connecting it to other aromatic rings.

32. The method for producing a deuterated aromatic compound according to claim 31, wherein, The first fused ring atom having the connecting bond is adjacent to the second fused ring atom and the third fused ring atom on both sides, and at least one of the second fused ring atom and the third fused ring atom is not an atom that constitutes a ring fused with an aromatic ring containing the first fused ring atom, the second fused ring atom and the third fused ring atom.

33. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, When 1 mL of deuterium-containing solvent is used relative to 1 g of the aromatic compound, which is defined as 1 (v / w), the amount of deuterium-containing solvent used is 5 (v / w) or more and 10,000 (v / w) or less.

34. The method for producing a deuterated aromatic compound according to claim 33, wherein, The amount of the deuterium-containing solvent used is 10 (v / w) or more and 1000 (v / w) or less.

35. The method for producing a deuterated aromatic compound according to claim 33, wherein, The amount of the deuterium-containing solvent used is 50 (v / w) or more and 500 (v / w) or less.

36. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The reaction temperature for the process of deuterating the aromatic compound in the deuterated solvent is above 0°C and the boiling point of the deuterated solvent used in the process is below that of the solvent.

37. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The reaction temperature for the process of deuterating the aromatic compound in the deuterium-containing solvent is above 20°C and below the boiling point of the deuterium-containing solvent.

38. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The reaction temperature for the process of deuterating the aromatic compound in the deuterium-containing solvent is above 40°C and below the boiling point of the deuterium-containing solvent, which is -10°C.

39. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The step of deuterating the aromatic compound in the deuterium-containing solvent includes: The steps of dissolving the aromatic compound, which is a reactant, in the deuterium-containing solvent to obtain a solution, and... The process of adding a catalyst capable of exchanging protium for deuterium to the solution and causing the reaction.

40. The method for producing a deuterated aromatic compound according to claim 39, wherein, The catalyst is selected from at least one of aluminum catalysts, platinum catalysts, and palladium catalysts.

41. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The deuterated aromatic compound produced has a deuteration rate of 80% or more, which is determined by NMR analysis.

42. The method for producing a deuterated aromatic compound according to claim 41, wherein, The deuterated aromatic compound produced has a deuteration rate of over 90%.

43. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The aromatic compound is any of the following compounds: 。 44. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The deuterated aromatic compound produced is any one of the following compounds: 。 45. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The deuterated aromatic compound produced is any one of the following compounds: 。 46. ​​The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The aromatic compound is any one of the compounds obtained by replacing all deuterium (D) with protium (H) in the following compounds. 。 47. The method for producing a deuterated aromatic compound according to claim 1 or 2, wherein, The aromatic compound is any one of the following compounds: BH-A, BH-B, BH-C, BH-D, BH-E, BH-F, BH-G, BH-H, and BH-J. 。

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