JP2024004495A - Method for producing deuterated aromatic compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing deuterated aromatic compound in which deuterated aromatic compound having high a high deuteration ratio can be efficiently produced.

SOLUTION: A method for producing a deuterated aromatic compound includes a process of deuterating an aromatic compound in deuterium-containing solvent. The aromatic compound has a structure in which two or more aromatic rings are bonded via a bonding hand in a molecule, where at least one of the two or more aromatic rings that the aromatic compound has is a condensed aromatic ring, at least one of the condensed aromatic ring has an aromatic ring including a first condensed ring atom having the bonding hand regarding bond with other aromatic rings, and a second condensed ring atom and a third condensed ring atom adjacent to the first condensed ring atom on both sides, and at least one of the second condensed ring atom and the third condensed ring atom is not an atom constituting a 6-membered ring out of a ring condensed for an aromatic ring having the first condensed ring atom, the second condensed ring atom and the third condensed ring atom.

SELECTED DRAWING: Figure 1

COPYRIGHT: (C)2024,JPO&INPIT

Description

The present invention relates to a method for producing a deuterated aromatic compound.

Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are applied to full-color displays such as mobile phones and televisions. When a voltage is applied to the organic EL element, holes are injected from the anode into the emissive layer, and electrons are injected from the cathode into the emissive layer. Then, in the light emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
In order to improve the performance of organic EL devices, various studies have been made on compounds used in organic EL devices. Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life span.

For example, Patent Document 1 and Patent Document 2 describe deuterated compounds and methods for producing the same as compounds for organic EL devices.
Patent Document 1 describes a method for deuterating an aryl-substituted anthracene compound in which an aryl group is bonded to the 9- and 10-position carbon atoms of anthracene.
Patent Document 2 describes a method including a plurality of steps for synthesizing a deuterated intermediate and a step of synthesizing a deuterated diarylpyrene using a plurality of deuterated intermediates. has been done.

Korean Registered Patent No. 10-1427457 Korean Registered Patent No. 10-1790854

In the method described in Patent Document 1, the efficiency of deuterating light hydrogen in the molecule of the aryl-substituted anthracene compound (deuteration rate) is low.
In order to produce deuterated diarylpyrene by the method described in Patent Document 2, multiple steps are required and the production efficiency is low.

An object of the present invention is to provide a method for producing a deuterated aromatic compound that can efficiently produce a deuterated aromatic compound with a high degree of deuteration.

According to one aspect of the present invention, there is provided a method for producing a deuterated aromatic compound, the method comprising: deuterating an aromatic compound in a deuterium-containing solvent; The aromatic compound has a structure in which two or more aromatic rings are bonded via a bond in the molecule, and at least one of the two or more aromatic rings possessed by the aromatic compound is a fused aromatic ring. and at least one of the fused aromatic rings includes a first fused ring atom having the bond for bonding to another aromatic ring, and a second fused ring that is adjacent to the first fused ring atom on both sides. atom and a third fused ring atom, and at least one of the second fused ring atom and the third fused ring atom includes the first fused ring atom, the second fused ring atom, and the third fused ring atom. Provided is a method for producing a deuterated aromatic compound in which the atoms condensed to an aromatic ring containing a third fused ring atom are not atoms constituting a six-membered ring.

According to one aspect of the present invention, it is possible to provide a method for producing a deuterated aromatic compound that can efficiently produce a deuterated aromatic compound with a high degree of deuteration.

1 is a ¹ H NMR spectrum of a deuterated aromatic compound produced by the production method according to Example 1. 1 is a ¹ H NMR spectrum of an aromatic compound used in the production method according to Example 1.

The method for producing a deuterated aromatic compound of this embodiment is a method for producing a deuterated aromatic compound. The method for producing a deuterated aromatic compound of the present embodiment includes a step of deuterating an aromatic compound in a deuterium-containing solvent. The aromatic compound has a structure in which two or more aromatic rings are bonded via bonds within the molecule. At least one of the two or more aromatic rings that the aromatic compound has is a fused aromatic ring. At least one of the fused aromatic rings includes a first fused ring atom having the bond for bonding to another aromatic ring, a second fused ring atom adjacent to the first fused ring atom on both sides, and and a third fused ring atom. At least one of the second fused ring atom and the third fused ring atom is a ring fused to an aromatic ring including the first fused ring atom, the second fused ring atom, and the third fused ring atom. , is not an atom constituting a 6-membered ring.

The aromatic compound used in the method for producing a deuterated aromatic compound of this embodiment is a non-deuterated aromatic compound (sometimes referred to as a non-deuterated aromatic compound).

In this specification, an aromatic ring means a ring in which the number of π electrons is 4n+2 (n is a positive integer including 0). The aromatic ring is at least one of an aromatic hydrocarbon ring and an aromatic heterocycle.

The ring fused to the aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom is preferably a 5-membered ring, a 6-membered ring, a 7-membered ring, or an 8-membered ring, More preferably, it is a 5-membered ring or a 6-membered ring.

"At least one of the second fused ring atom and the third fused ring atom is a 6-membered ring among the rings fused to the aromatic ring including the first fused ring atom, the second fused ring atom, and the third fused ring atom. "Not an atom constituting" means, for example, the following (E1), (E2) or (E3).

(E1) One of the second fused ring atom and the third fused ring atom constitutes a 6-membered ring fused to an aromatic ring containing 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 included only 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 constitutes a 6-membered ring fused to an aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom. an atom, and the other of the second fused ring atom and the third fused ring atom constitutes a 5-membered ring fused to an aromatic ring containing the first fused ring atom, the second fused ring atom, and the third fused ring atom It is an atom that

(E3) Both the second condensed ring atom and the third condensed ring atom are not atoms constituting a ring condensed to an aromatic ring containing the first condensed ring atom, the second condensed ring atom, and the third condensed ring atom. .

The atoms constituting the ring condensed to the aromatic ring including the first condensed ring atom, the second condensed ring atom, and the third condensed ring atom are carbon atoms or heteroatoms, and the heteroatoms include, for example, oxygen atoms. , sulfur atom, nitrogen atom, boron atom and phosphorus atom.

For example, the following compound BH-A corresponds to an aromatic compound used in the method for producing a deuterated aromatic compound of the present embodiment.

Compound BH-A has four aromatic rings in the molecule. Compound BH-A has a structure in which four aromatic rings are bonded via bonds (single bonds). Of the four aromatic rings that compound BH-A has, two are fused aromatic rings (pyrene rings). As shown in the structural formula below, the pyrene ring that compound BH-A has has a first condensed ring atom C1 having a bond related to a bond with another aromatic ring B1 (benzene ring), and a first condensed ring atom _C1 . ₁ and a second fused ring atom C ₂ and a third fused ring atom C ₃ adjacent on both sides.

In compound BH-A, the second fused ring atom C ₂ is a 6-membered aromatic ring A1 containing the first fused ring atom C ₁ , the second fused ring atom C ₂ and the third fused ring atom C ₃ It is not an atom constituting ring A2, which is a ring. The third condensed ring atom _C3 is an atom constituting ring A2 condensed to aromatic ring A1. The second fused ring atom C ₂ and the third fused ring atom C ₃ of ring A1 in compound BH-A correspond to the case of (E1) above.

For example, the following compound Ref-BH-A does not correspond to the aromatic compound used in the method for producing a deuterated aromatic compound of the present embodiment.

Compound Ref-BH-A has three aromatic rings in the molecule. The compound Ref-BH-A has a structure in which three aromatic rings are bonded via a bond (single bond). Of the three aromatic rings that the compound Ref-BH-A has, two are fused aromatic rings (anthracene ring and dibenzofuran ring). As shown in the structural formula below, the anthracene ring that the compound Ref-BH-A has has a first condensed ring atom _C1 having a bond related to a bond with another aromatic ring B1 (benzene ring), and a first condensed ring. It has an aromatic ring A1 including an atom _C1 and a second condensed ring atom _C2 and a third condensed ring atom _C3 adjacent on both sides. The aromatic ring A1 has a first condensed ring atom C4 having a bond for bonding with another aromatic ring (dibenzofuran ring), and a second condensed ring atom _C4 adjacent to the first condensed ring atom _C4 on both sides. ₅ and a third fused ring atom _C6 . The first condensed ring atom _C4 is bonded to one aromatic ring D1 constituting the dibenzofuran ring as another aromatic ring via a bond.

In compound Ref-BH-A, the second fused ring atoms C ₂ and C ₅ are atoms constituting ring A2, which is a 6-membered ring fused to aromatic ring A1. Furthermore, in compound Ref-BH-A, the third fused ring atoms C ₃ and C ₆ are atoms constituting ring A3, which is a 6-membered ring fused to aromatic ring A1. Thus, in the compound Ref-BH-A, the second fused ring atoms C ₂ and C ₅ and the third fused ring atoms C ₃ and C ₆ are both ring A2 or ring A3 fused to the aromatic ring A1. Since these are constituent atoms, the compound Ref-BH-A does not correspond to the aromatic compound used in the method for producing a deuterated aromatic compound of the present embodiment.
As in the compound Ref-BH-A, when the second condensed ring atom and the third condensed ring atom are atoms constituting ring A2 or ring A3 condensed to aromatic ring A1, the third condensed ring atom of ring A2 or ring A3 is Hydrogen atoms bonded to carbon atoms near the second fused ring atom and third fused ring atom and hydrogen atoms bonded to ring B1 or ring D1 are close to each other, creating a bulky site in the molecule. Hydrogen atoms that occur and are located in such bulky sites are less likely to be deuterated.

In the method for producing a deuterated aromatic compound of the present embodiment, at least one of the condensed aromatic rings is preferably a condensed aromatic ring in which three or more rings are condensed.

In the method for producing a deuterated aromatic compound of the present embodiment, the fused aromatic ring is a fused aromatic hydrocarbon ring having 10 to 30 ring carbon atoms or a fused aromatic ring having 9 to 30 ring atoms. Preferably it is a heterocycle.

In the method for producing a deuterated aromatic compound of the present embodiment, at least one of the fused aromatic rings is a pyrene ring, a fluoranthene ring, a benzofluoranthene ring, a phenanthrene ring, a benzophenanthrene ring, a chrysene ring, a benzochrysene ring, Triphenylene ring, benzotriphenylene ring, benzoxanthene ring, anthracene ring (provided that at least one of the carbon atoms at the 1st to 8th positions of the anthracene ring has the above-mentioned bond), and benzo[a]anthracene ring (however, At least one of the carbon atoms at positions 1 to 6 and positions 8 to 11 of the benzo[a]anthracene ring has the bond. .

In the method for producing a deuterated aromatic compound of the present embodiment, at least one of the condensed aromatic rings is at least one selected from the group consisting of rings represented by the following formulas (101) to (144). A ring is preferred.

(In the formulas (101) to (144), each * independently represents a bonding position of the bond to another aromatic ring in the aromatic compound.)

In the method for producing a deuterated aromatic compound of the present embodiment, the fused aromatic ring preferably does not include a ring represented by the following formulas (X1), (X2), (X3), and (X4).

(In the formulas (X1), (X2), (X3) and (X4), * is each independently a bonding position of the bond to another aromatic ring in the aromatic compound.)

For example, in the condensed ring represented by the formula (102), the second condensed ring atom and the third condensed ring atom of the aromatic ring to which the bond is bonded correspond to the above-mentioned case (E3).

In the method for producing a deuterated aromatic compound of the present embodiment, the aromatic compound has two or more condensed aromatic rings, and the two or more condensed aromatic rings are all the above-mentioned (E1), ( It is preferable to have an aromatic ring containing a first condensed ring atom, a second condensed ring atom, and a third condensed ring atom corresponding to either case E2) or (E3), and the above-mentioned (E1) or ( It is more preferable to have an aromatic ring containing a first condensed ring atom, a second condensed ring atom, and a third condensed ring atom corresponding to any of the cases of E3). In one embodiment, two or more fused aromatic rings have the same structure. In one embodiment, the two or more fused aromatic rings are of different structures. Note that the same structure means that the positions of the ring skeleton and the bond are the same.

In the method for producing a deuterated aromatic compound of the present embodiment, when the aromatic compound has a plurality of condensed aromatic rings, each of these plurality of condensed aromatic rings has a bond bond related to a bond with another aromatic ring. and a second fused ring atom and a third fused ring atom adjacent to the first fused ring atom on both sides, the second fused ring atom and the third fused ring atom are At least one of the ring atoms is preferably not an atom constituting a 6-membered ring among the rings condensed to the aromatic ring including the first condensed ring atom, the second condensed ring atom, and the third condensed ring atom.

In the method for producing a deuterated aromatic compound of the present embodiment, when the aromatic compound has a plurality of condensed aromatic rings, all of these plurality of condensed aromatic rings are represented by the above formulas (101) to (144). It is preferable that at least one ring is selected from the group consisting of rings.

The aromatic compound used in the method for producing a deuterated aromatic compound of the present embodiment has a first condensed ring corresponding to any of the cases (E1), (E2), or (E3) described above in the condensed aromatic ring. It is also preferable that the first fused ring has a plurality of sets consisting of a ring atom, a second fused ring atom, and a third fused ring atom, and corresponds to either of the above cases (E1) or (E3). It is also preferable to have a plurality of sets consisting of atoms, second condensed ring atoms, and third condensed ring atoms.

The fused aromatic ring in the aromatic compound used in the method for producing a deuterated aromatic compound of this embodiment may have multiple bonds to other aromatic rings. The first fused ring atoms having the bond are adjacent to the second fused ring atoms and the third fused ring atoms on both sides, and at least one of the second fused ring atoms and the third fused ring atoms is adjacent to the second fused ring atoms and the third fused ring atoms. It is preferable that the atom is not an atom constituting a ring condensed to an aromatic ring including a first condensed ring atom, a second condensed ring atom, and a third condensed ring atom.
For example, one embodiment of the case where the fused aromatic ring represented by the above formula (101) further has a bond is a fused aromatic ring represented by the following formula (148).

The fused aromatic ring represented by the above formula (148) includes a first fused ring atom C 11 having a bond for bonding to another aromatic ring, and a first fused ring atom C ₁₁ adjacent to the first fused ring atom C ₁₁ on both sides. An aromatic ring A11 containing two condensed ring atoms _C12 and a third condensed ring atom _C13 , a first condensed ring atom _C14 having a bond related to a bond with another aromatic ring, and a first condensed ring atom It includes an aromatic ring A13 that includes C ₁₄ and a second fused ring atom C ₁₅ and a third fused ring atom C ₁₆ adjacent on both sides.
In the fused aromatic ring represented by formula (148), the second fused ring atom C ₁₂ is not an atom constituting ring A12 and ring A14 condensed to aromatic ring A11, but is a third fused ring atom C ₁₃ is an atom constituting ring A12 condensed with aromatic ring A11.
In the fused aromatic ring represented by formula (148), the second fused ring atom C ₁₅ is not an atom constituting ring A12 and ring A14 that are fused to aromatic ring A13, but is a third fused ring atom C ₁₆ is an atom constituting ring A14 condensed to aromatic ring A13.

It is also preferable that the aromatic compound used in the method for producing a deuterated aromatic compound of this embodiment does not have an anthracene ring.

In the method for producing a deuterated aromatic compound of the present embodiment, the deuterium-containing solvent preferably contains deuterium in the solvent molecule. Deuterium-containing solvents include heavy benzene (benzene-d6, C ₆ D ₆ ), heavy water (D ₂ O), benzene-d4 (C ₆ D ₄ H ₂ ), and heavy toluene (toluene-d8, CD ₃ C ₆ D ₅ ), and the deuterium-containing solvent is more preferably heavy benzene (C ₆ D ₆ ) or heavy water (D ₂ O).

In the method for producing a deuterated aromatic compound of the present embodiment, it is preferable to use at least one catalyst that can exchange light hydrogen into deuterium in the step of deuterating the aromatic compound in a deuterium-containing solvent. It is also preferred to use, for example, Lewis acid H/D exchange catalysts.

In the method for producing a deuterated aromatic compound of the present embodiment, in the step of deuterating the aromatic compound in a deuterium-containing solvent, at least one selected from the group consisting of an aluminum catalyst, a platinum catalyst, and a palladium catalyst is used. Preference is given to using one type of catalyst.

Examples of the aluminum catalyst include aluminum trichloride and ethylaluminum chloride.

Further, the step of deuterating an aromatic compound in a deuterium-containing solvent may include, for example, an aromatic compound and a palladium catalyst of 0.01% by mass or more and 200% by mass or less based on the total mass of the aromatic compound. and a platinum catalyst (mass ratio 1:1) (the total of palladium metal and platinum metal is 0.0005% by mass or more and 20% by mass or less based on the total mass of the aromatic compound), which is deuterated. In addition to the solvent (in an amount of 1 equivalent or more and 20,000 equivalents or less, preferably 10 equivalents or more and 700 equivalents or less per equivalent of the mixed catalyst), the reaction system is sealed, and the system is replaced with hydrogen gas, The mixture is stirred and reacted in an oil bath at a temperature of about 20° C. or more and 200° C. or less for about 30 minutes or more and 100 hours or less.

The deuteration rate of the deuterated aromatic compound produced by the method for producing a deuterated aromatic compound of the present embodiment is preferably 70% or more, more preferably 80% or more, and 90% or more. % or more is more preferable.
The deuteration rate of a deuterated aromatic compound can be determined by NMR analysis.

(Specific examples of aromatic compounds)
In the method for producing a deuterated aromatic compound of the present embodiment, specific examples of the aromatic compound used include the following compounds. However, the present invention is not limited to these specific examples of aromatic compounds.

(Specific examples of deuterated aromatic compounds)
Specific examples of the deuterated aromatic compound produced by the method for producing a deuterated aromatic compound of the present embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of deuterated aromatic compounds.

According to the method for producing a deuterated aromatic compound of the present embodiment, light hydrogen in the molecule of an aromatic compound having a predetermined condensed polycyclic skeleton can be efficiently deuterated.
The conventional method for deuterating light hydrogen in molecules of aromatic compounds consists of a step of synthesizing an intermediate in which the aromatic rings constituting the aromatic compound are individually deuterated, and a step of synthesizing an intermediate in which the aromatic rings constituting the aromatic compound are individually deuterated. This required a step of synthesizing a compound in which the light hydrogen in the molecule was deuterated using a deuterated compound.
The method for producing a deuterated aromatic compound of the present embodiment includes a step of deuterating an aromatic compound (light hydrogen compound) having the same skeleton as the deuterium compound to be produced in a deuterium-containing solvent. Since the light hydrogen in the molecule of the compound can be deuterated, the production method requires fewer steps and can be produced more efficiently than conventional methods.
Further, in the method of deuterating an aromatic compound having 9,10-anthracenediyl as a condensed polycyclic skeleton, the deuteration rate is low, but according to the method for producing a deuterated aromatic compound of this embodiment. , deuterated aromatic compounds can be produced with a higher deuteration rate.

The deuterated aromatic compound produced by the method for producing a deuterated aromatic compound of the present embodiment can be used as a material for various purposes, for example, it can also be used as a material for an organic electroluminescent device. .
An organic electroluminescent device (sometimes referred to as an organic EL device) includes an organic layer between an anode and a cathode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating a plurality of layers made of organic compounds. The organic layer may further contain an inorganic compound. In an organic EL element, at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, one light emitting layer, or may include layers that can be employed in an organic EL element. Layers that can be employed in the organic EL device are not particularly limited, but may be selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron barrier layer, an electron injection layer, an electron transport layer, and a hole barrier layer. At least one of the layers is mentioned.
The organic layer of the organic EL element preferably has one of the following layer configurations, for example.
・Electron barrier layer / Emissive layer / Hole blocking layer ・Hole injection layer / Electron barrier layer / Emissive layer / Hole blocking layer ・Hole transport layer / Electron barrier layer / Emissive layer / Hole blocking layer ・Hole injection Layer/Hole transport layer/Electron barrier layer/Emissive layer/Hole barrier layer/Electron barrier layer/Emissive layer/Hole barrier layer/Electron injection layer/Electron barrier layer/Emissive layer/Hole barrier layer/Electron transport layer・Electron barrier layer / Emissive layer / Hole barrier layer / Electron transport layer / Electron injection layer ・Hole injection layer / Electron barrier layer / Emissive layer / Hole barrier layer / Electron injection layer ・Hole injection layer / Electron barrier layer /Emissive layer/Hole blocking layer/Electron transport layer/Hole injection layer/Electron barrier layer/Emissive layer/Hole blocking layer/Electron transport layer/Electron injection layer/Hole transport layer/Electron barrier layer/Emissive layer/ Hole blocking layer/electron injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer /Electron injection layer/Hole injection layer/Hole transport layer/Electron barrier layer/Emissive layer/Hole barrier layer/Electron injection layer/Hole injection layer/Hole transport layer/Electron barrier layer/Emissive layer/Hole Barrier layer/electron transport layer/hole injection layer/hole transport layer/electron barrier layer/light emitting layer/hole barrier layer/electron transport layer/electron injection layer

The deuterated aromatic compound produced by the method for producing a deuterated aromatic compound of the present embodiment is preferably contained in at least one of the organic layers of the organic EL element. The deuterated aromatic compound may be contained in multiple layers.

The deuterated aromatic compound may be contained alone in one layer, or may be contained together with at least one other compound. The other compounds contained in one layer together with the deuterated aromatic compound may each independently be a non-deuterated compound (sometimes referred to as a non-deuterated compound). , deuterated compounds may also be used.

It should be noted that the present invention is not limited to the above-described embodiments, and any changes, improvements, etc. that can achieve the purpose of the present invention are included in the present invention. For example, the specific materials, reaction conditions, structure, shape, etc. in carrying out the present invention may be changed or improved within the scope of achieving the purpose of the present invention.

Examples according to the present invention will be described below. The present invention is not limited in any way by these Examples.

<Manufacture of compounds>
(Example 1)
Example 1 relates to a method for producing compound BH-1 as a deuterated aromatic compound. A synthetic scheme for compound BH-1 is shown below.

(1) Synthesis of deuterium (compound BH-1) Under an argon atmosphere, 19.0 g of light hydrogen (compound BH-A) as a non-deuterated aromatic compound, 4.6 g of aluminum chloride, and heavy benzene d ₆ was added to the flask, and the mixture was stirred under reflux at 40°C for 29 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was washed with water and acetone. The washed solid was recrystallized with a mixed solvent of toluene and hexane to obtain 15.3 g (yield: 77%) of an orange solid. As a result of mass spectrometry analysis, this orange solid was found to be compound BH-1 as a deuterated aromatic compound, with a molecular weight of 580.85 and m/e=581.

[Calculation of deuteration rate of deuterium body (compound BH-1)]
NMR measurement was performed on 10.2 mg (0.0184 mmol) of a standard light hydrogen compound (compound BH-A, molecular weight: 554.69) in deuterahydrofuran. FIG. 2 is a ¹ H NMR spectrum of the aromatic compound (compound BH-A) used in the production method according to Example 1. The total integrated value of protons in the molecule was 13259.62, and the number of protons in one molecule was 26, when methane dibromide was taken as a reference value of 100.
On the other hand, 9.9 mg (0.0170 mmol) of a deuterium compound (compound BH-1, molecular weight: 580.85) was also subjected to NMR measurement in deuterahydrofuran. FIG. 1 is a ¹ H NMR spectrum of the deuterated aromatic compound (compound BH-1) produced by the production method according to Example 1. The total integral value of protons in the molecule was 802.61, when methane dibromide was taken as a reference and 100. Taking into consideration the molar ratio of light hydrogen and deuterium, the total integral value of protons that could not be deuterated in deuterium is 802.61×(0.0184/0.0170)=868. It was 71. When calculated based on the total integral value of protons of the deuterium body and the total integral value of protons of the light hydrogen body, the deuteration rate was 93.4% as shown in the following calculation formula.
{1-(868.71/13259.62)}×100=93.4%

Since the production method according to Example 1 used an aromatic compound (compound BH-A) having a predetermined ring structure, it was possible to efficiently produce a deuterated aromatic compound (compound BH-1) with a high degree of deuteration. Manufactured.

Claims (7)

A method for producing a deuterated aromatic compound, the method comprising:
a step of deuterating an aromatic compound in a deuterium-containing solvent;
The aromatic compound has a structure in which two or more aromatic rings are bonded via a bond within the molecule,
At least one of the two or more aromatic rings possessed by the aromatic compound is a fused aromatic ring,
At least one of the fused aromatic rings includes a first fused ring atom having the bond for bonding to another aromatic ring, a second fused ring atom adjacent to the first fused ring atom on both sides, and having an aromatic ring comprising a third fused ring atom,
At least one of the second fused ring atom and the third fused ring atom is a ring fused to an aromatic ring including the first fused ring atom, the second fused ring atom, and the third fused ring atom. , is not an atom that constitutes a 6-membered ring,
A method for producing a deuterated aromatic compound. The method for producing a deuterated aromatic compound according to claim 1,
The deuterium-containing solvent is heavy benzene or heavy water,
A method for producing a deuterated aromatic compound. In the method for producing a deuterated aromatic compound according to claim 1 or 2,
At least one of the fused aromatic rings is a fused aromatic ring in which three or more rings are fused,
A method for producing a deuterated aromatic compound. In the method for producing a deuterated aromatic compound according to any one of claims 1 to 3,
At least one of the fused aromatic rings is
pyrene ring,
fluoranthene ring,
benzofluoranthene ring,
phenanthrene ring,
benzophenanthrene ring,
Chrysene ring,
benzochrysene ring,
triphenylene ring,
benzotriphenylene ring,
benzoxanthene ring,
an anthracene ring (however, at least one of the carbon atoms at positions 1 to 8 of the anthracene ring has the above-mentioned bond), and a benzo[a]anthracene ring (however, the 1st to 8th positions of the benzo[a]anthracene ring) At least one of the carbon atoms at the 6th and 8th to 11th positions has the above-mentioned bond.
A method for producing a deuterated aromatic compound. In the method for producing a deuterated aromatic compound according to any one of claims 1 to 3,
At least one of the fused aromatic rings is at least one ring selected from the group consisting of rings represented by the following formulas (101) to (144),
A method for producing a deuterated aromatic compound.

(In the formulas (101) to (144), each * independently represents a bonding position of the bond to another aromatic ring in the aromatic compound.) In the method for producing a deuterated aromatic compound according to any one of claims 1 to 5,
The fused aromatic ring does not include a ring represented by the following formulas (X1), (X2), (X3) and (X4),
A method for producing a deuterated aromatic compound.

(In the formulas (X1), (X2), (X3) and (X4), * is each independently a bonding position of the bond to another aromatic ring in the aromatic compound.) In the method for producing a deuterated aromatic compound according to any one of claims 1 to 6,
In the step of deuterating the aromatic compound in a deuterium-containing solvent, at least one catalyst selected from the group consisting of an aluminum catalyst, a platinum catalyst, and a palladium catalyst is used.
A method for producing a deuterated aromatic compound.