JP2019131487A - Triaryltriazine compound, and manufacturing method therefor - Google Patents

Abstract

To overcome problems that a halogen added article is produced as by product because a transition metal halide affects as a halogenation agent when a triaryltriazine compound is manufactured by reacting an aromatic nitrile compound and aromatic acid chloride in the presence of the transition metal halide, and that reduction and removal of the halogen added article is needed because the halogen added article has adverse effects on performance of an organic electroluminescent element.SOLUTION: There are provided a triaryltriazine compound less in content of a halogen added article by reacting an aromatic nitrile compound and aromatic acid chloride at a temperature in a range of 15 to 65°C in the presence of a transition metal halide to manufacture an oxonium salt compound, and further reacting the oxonium salt compound with an amine source, a manufacturing method therefor.SELECTED DRAWING: None

Description

  The present invention relates to a triaryltriazine compound useful as a synthetic intermediate for a charge transport material used in an organic electroluminescent device, and a method for producing the same.

  Triaryltriazine compounds having the same or different aromatic groups at the 2-position, 4-position, and 6-position of the 1,3,5-triazine ring are very useful as charge transport materials used in, for example, organic electroluminescence devices (For example, Patent Documents 1 and 2).

  As a method for producing these compounds, a method of reacting an aromatic nitrile compound and an aromatic acid chloride in the presence of a transition metal halogen compound is generally used (for example, Patent Document 3). In this method, the transition metal halogen compound acts as a Lewis acid, but partly acts as a halogenating agent, so that there is a problem that a halogen adduct is by-produced. It is widely known that when the halogen adduct remains in the charge transport material, it adversely affects the performance of the organic electroluminescent device, and it has been an urgent task to remove the halogen adduct.

  According to the method of Patent Document 3, 4-cyanobiphenyl and 3-bromo-5-chlorobenzoic acid chloride were reacted in the presence of antimony chloride. As a result, the halogen adduct contained 1.2 to 1.6% in terms of LC purity. To obtain triaryltriazine compounds (results shown in Comparative Examples 1-2). The resulting triaryltriazine compound was further induced into a charge transport material, but impurities derived from the halogen adduct were by-produced and a high-purity charge transport material could not be obtained. It became difficult. That is, removal or reduction of the halogen adduct is required.

  As a method for removing the halogen adduct, a purification method such as distillation or recrystallization is generally used. However, the halogen adduct is generally difficult to purify and remove because it has similar chemical and physical properties to the target triaryltriazine compound.

  As a method for reducing the amount of the halogen adduct produced, a method in which no transition metal halogen compound is used can be mentioned. As the method, a method of introducing a substituent stepwise from cyanuric chloride as a starting material (for example, Non-Patent Document 1), a method of producing a triaryltriazine compound from an aromatic amidine compound and an aromatic aldehyde compound ( For example, Patent Document 4) has been reported. Although these methods do not produce a halogen adduct as a by-product, there are problems in industrial production methods such as requiring multi-step processes, using special reaction raw materials, and low reaction selectivity.

Patent 531824 Patent No. 5761907 Japanese Patent No. 5529407 Patent 5719528

Advanced Synthesis & Catalysis, 359 (14), 2514-2519 (2017)

  An object of the present invention is to provide a method for producing a triaryltriazine compound capable of reducing the production amount of a halogen adduct while using a transition metal halogen compound that is excellent in terms of industrial productivity, and An object of the present invention is to provide a high-purity triaryltriazine compound with a low content of the halogen adduct by the production method.

  As a result of intensive studies to solve the above problems, the present inventors have reacted an aromatic nitrile compound and an aromatic acid chloride in the presence of a transition metal halogen compound at a temperature in the range of 15 to 65 ° C. As a result, it was found that the by-product of the halogen adduct to be reduced can be suppressed, and the present invention has been completed.

  That is, the present invention relates to the general formula (1)

(In the formula, Ar ¹ and Ar ² each independently represent an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms. X represents I, Br. , Cl or F. n represents an integer of 1 to 6.)
The halogen-added triaryltriazine compound represented by the formula (2) is contained in a range of 1.0% or less in terms of LC purity.

(In the formula, Ar ¹ and Ar ² have the same meaning as in the general formula (1).)
It is related with the triaryl triazine compound represented by these.

In the present invention, the Ar ² is represented by the following formula (3):

It is related with the triaryl azine compound which is group represented by these.

The present invention also relates to a triarylazine compound wherein each Ar ¹ is independently a monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms.

  The present invention also provides a general formula (4)

(In the formula, Ar ¹ represents an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms.)
An aromatic nitrile compound represented by the general formula (5)

(In the formula, Ar ² represents an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms.)
Wherein an oxonium salt compound is produced in the presence of a transition metal halogen compound in the temperature range of 15 to 65 ° C., and the oxonium salt compound is further reacted with an amine source. The present invention relates to a method for producing a triaryltriazine compound represented by the general formula (1).

  Further, in the present invention, the substrate concentration of the aromatic nitrile compound represented by the general formula (4) is 2.0 mol / L or less, and the substrate concentration of the aromatic acid chloride represented by the general formula (5) Is 1.0 mol / L or less, and relates to a method for producing the triaryltriazine.

  Furthermore, the present invention relates to a method for producing the triaryltriazine, wherein the transition metal halogen compound is antimony chloride.

  According to the present invention, a high-purity triaryltriazine compound having a small content of a halogen-added triaryltriazine compound can be easily produced industrially. Further, by inducing the obtained triaryltriazine compound, a high-purity charge transport material can be obtained, which can contribute to improving the performance of the organic electroluminescent device, and the present invention is extremely useful industrially.

  Hereinafter, the present invention will be described in more detail.

In the general formulas (1) and (2), Ar ¹ and Ar ² each independently represent an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms. Represent. X represents I, Br, Cl, or F. n represents an integer of 1 to 6.

The monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms which may be substituted represented by Ar ¹ and Ar ² is not particularly limited. Biphenyl group which may have, naphthyl group which may have substituent, anthracenyl group which may have substituent, pyrenyl group which may have substituent, and substituent A terphenyl group which may have a substituent, a phenanthracenyl group which may have a substituent, a perylenyl group which may have a substituent, or a triphenylenyl group which may have a substituent. It is done.

  The substituent on the monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms which may be substituted is not particularly limited, and examples thereof include halogen elements (I, Br , Cl or F), methyl group, ethyl group, alkyl group having 3 to 18 carbon atoms (for example, n-propyl group, i-propyl group, n-butyl group, sec-butyl group, tert-butyl group, n -Hexyl group, cyclohexyl group, cyclohexadienyl group, octyl group, benzyl group, or phenethyl group), a halogenated alkyl group having 1 to 18 carbon atoms (for example, trifluoromethyl group, etc.), methoxy group, ethoxy group, C3-C18 alkoxy group (for example, n-propyloxy group, i-propyloxy group, n-butyloxy group, sec-butyloxy group, tert-butyloxy group) n-hexyloxy group, cyclohexyloxy group, cyclohexadienyloxy group, octyloxy group, benzyloxy group, phenethyloxy group, etc.), C1-C18 halogenated alkoxy group (for example, trifluoromethoxy group, etc.), C3-C24 aromatic groups (phenyl group, tolyl group, pyridyl group, pyrimidyl group, carbazolyl group, dibenzothienyl group, dibenzofuranyl group, etc.), nitro group, cyano group and the like can be mentioned.

Ar ¹ is not particularly limited in that it can be derived into a charge transport material. For example, each of them independently represents a monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms. (This group includes a halogen element, methyl group, trifluoromethyl group, methoxy group, benzyloxy group, trifluoromethoxy group, phenyl group, tolyl group, pyridyl group, carbazolyl group, dibenzothienyl group, dibenzofuranyl group, nitro group, Or an unsubstituted or substituted aromatic hydrocarbon group having 10 to 24 carbon atoms, more preferably a biphenylyl group. , A naphthyl group, or a terphenyl group is more preferable.

Ar ² is not particularly limited in that it can be induced into a charge transport material, but for example, a group represented by the following general formula (1-1) is preferable.

(Z in the formula represents I, Br, Cl, or F, and Z may be the same or different from each other. M represents an integer of 0 to 5)
The m is preferably 1, 2, or 3, more preferably 1 or 2, in terms of induction to the charge transport material.

Further, the monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms which may be substituted represented by Ar ² is particularly limited in that it can be derived into a charge transport material. For example, a group represented by the following formula (3) is more preferable.

  That is, for the halogen-added triaryltriazine compound represented by the general formula (1), the following general formula (1 ′)

(Wherein, ^Ar 1, X, and for n is ^Ar 1, X, and synonymous with n in the general formula (1).)
It is preferable that it is a halogen addition triaryl triazine compound represented by these.

  The triaryltriazine compound represented by the general formula (2) is represented by the following general formula (2 ').

(Wherein the Ar ¹ has the same meaning as Ar ¹ in formula (1 ').)
It is preferable that it is a triaryl triazine compound represented by these.

In the general formula (1), X represents I, Br, Cl, F. n represents an integer of 1 to 6. X may be substituted with either Ar ^{1 or} Ar ² , or may be substituted with any one of them.

  N in the general formula (1) is preferably 1, 2 or 3, more preferably 1 or 2 in terms of easy by-production.

  Although it does not specifically limit as a compound represented by General formula (1), For example, the following can be illustrated. In addition, the compound represented by General formula (1) is contained as a by-product in the compound represented by General formula (2) manufactured by the manufacturing method mentioned later, The catalyst which advances the said manufacturing method A by-product in which a halogen element derived from a Lewis acid (transition metal halogen compound) used as is unintentionally added to the compound represented by the general formula (2) is shown. That is, the compound represented by the general formula (1) is characterized by having n extra halogen elements than the compound represented by the general formula (2). The “n extra halogen elements X” peculiar to the general formula (1) are bonded to any aromatic ring carbon atom of the halogen-added triaryltriazine compound represented by the general formula (1). The halogen-added triaryltriazine compound represented by the general formula (1) is a product by-produced with the production of the triaryltriazine compound represented by the general formula (2), and usually has a number of structures. Consists of isomers.

  The triaryltriazine compound represented by the general formula (2) has the following reaction formula:

(In the reaction formula, Ar ¹ and Ar ² have the same definitions as above. Y ⁻ represents a counter anion.)
It can manufacture from the process shown by. That is, the triaryltriazine compound can be produced by Step 1 (Oxonium salt production step) and Step 2 (Triazine production step).

  Hereinafter, Step 1: Oxonium salt production step will be described.

  It can be produced by reacting the aromatic nitrile compound represented by the general formula (4) and the aromatic acid chloride represented by the general formula (5) in the presence of a transition metal halogen compound. The aromatic nitrile compound (4) and the aromatic acid chloride (5) can be produced by methods known to those skilled in the art.

  In the oxonium salt (6), the molar ratio of the aromatic nitrile compound (4) and the aromatic acid chloride (5) is not particularly limited, but is, for example, in the range of 5: 1 to 1: 1. It is preferable, and 2: 1 to 1.5: 1 is more preferable in terms of good reaction selectivity.

The transition metal halogen compound preferably has Lewis acidity and is not particularly limited. For example, TiCl ₄ , ZrCl ₄ , MnCl ₂ , MnBr ₂ , FeCl ₃ , FeBr ₃ , ZnCl ₂ , BF ₃ , AlCl ₃ , AlBr ₃ , SnCl ₅ , SbCl ₃ , SbCl ₅ , SbBr _5, etc., and FeCl ₃ , AlCl ₃ , SnCl ₃ , or SbCl ₅ are more preferable in terms of easy availability. SbCl ₅ is more preferable in that the reaction yield is good. The amount of the transition metal halogen compound used is not particularly limited, but is preferably 1.0 to 5.0 molar equivalents relative to the aromatic acid chloride (5), and has good reaction yield and selectivity. And 1.0 to 1.5 molar equivalents are more preferable.

  In the reaction, a solvent may be optionally used. The solvent used is not particularly limited, and examples thereof include dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene, trichlorobenzene, and nitrobenzene, and the reaction yield and selectivity are good. Of these, chloroform or chlorobenzene is preferred. The solvent may be used alone or in combination of two or more.

  The amount of the solvent used is not particularly limited. For example, a range in which the substrate concentration of the aromatic nitrile compound (4) is 2.0 mol / L or less is preferable, and the substrate concentration of the aromatic acid chloride (5) is preferable. Is preferably 1.0 mol / L or less, more preferably the aromatic nitrile compound (4) has a substrate concentration of 1.4 mol / L or less, and the aromatic acid chloride (5) has a substrate concentration of A range of 0.7 mol / L or less is more preferable. When the substrate concentration of the aromatic nitrile compound (4) exceeds 2.0 mol / L and the substrate concentration of the aromatic acid chloride (5) exceeds 1.0 mo / L, the transition metal halogen compound acts as a halogenating agent. However, the by-product amount of perhalogenated adduct tends to increase.

  The reaction temperature of this step 1 (oxonium salt production step) may be in the range of 15 ° C. to 65 ° C., but it is 25 ° C. to 55 ° C. in terms of reaction yield and selectivity (suppression of perhalogen adduct). A range is preferred. When carried out at a reaction temperature of 65 ° C. or higher, the amount of perhalogenated adduct tends to increase. Further, when the reaction temperature is 15 ° C. or lower, the reaction yield tends to decrease.

  The reaction time varies depending on the type of substrate, the type of solvent, and the reaction temperature, and thus is not particularly limited, but it is usually preferably in the range of 1 to 24 hours.

  The reaction is preferably performed in an inert gas atmosphere such as nitrogen or argon, and can be performed at normal pressure or under pressure. After completion of the reaction, the solvent may be removed under vacuum or normal pressure or may be used in the next step 2 as it is.

In the oxonium salt compound represented by the general formula (6), Y ⁻ represents a counter anion and is derived from a Lewis acid (transition metal halogen compound) used in the reaction. Y ⁻ is not particularly limited, and examples thereof include TiCl ₅ ⁻ , ZrCl ₅ ⁻ , MnCl ₃ ⁻ , MnBr ₂ Cl ⁻ , FeCl ₄ ⁻ , FeBr ₃ Cl ⁻ , ZnCl ₃ ⁻ , BF ₃ Cl ⁻ , AlCl ₄ ⁻ , AlBr ₃ Cl ⁻ , SnCl ₆ ⁻ , SbCl ₄ ⁻ , SbCl ₆ ⁻ , or SbBr ₅ Cl ⁻ can be mentioned, and AlCl ₄ ⁻ and FeCl are easy to obtain and have good reaction yield. ₄ ^-, or SbCl ₆ ^- is preferable.

  Hereinafter, Step 2: Triazine production step will be described.

  The triaryltriazine compound (2) can be produced by reacting the oxonium salt compound represented by the general formula (6) with an ammonia source.

  The ammonia source can also be expressed as an ammonia compound, and is not particularly limited. For example, ammonia or ammonium chloride can be used, and ammonia is preferable in that the reaction yield is good. Ammonia can be passed as a gas into the reaction system, but is preferably dissolved in a solvent such as water, methanol, ethanol, diethyl ether, dichloromethane or the like and used as an ammonia solution in terms of simple operation. The concentration of the ammonia solution is preferably 1% by weight to a saturated solution, and a saturated solution is preferable in terms of reaction yield. The molar ratio of the oxonium salt compound (6) and the ammonia source is preferably 1: 1 to 1: 100, and more preferably 1: 1 to 1:30 in terms of a good reaction yield.

  The method of adding the ammonia source may be a method of adding to the oxonium salt compound (6) or a method of adding the oxonium salt compound (6) to the ammonia source.

  Examples of the solvent used in the reaction include the same solvents as those exemplified in Step 1. Chloroform, chlorobenzene, or dichlorobenzene is preferable in that the reaction yield is good. The solvent may be used alone or in combination of two or more.

  Although the reaction temperature of this process 2 (triazine production | generation process) has the preferable range of -50 degreeC-50 degreeC, the range of -30 degreeC-5 degreeC is more preferable at the point of reaction yield and selectivity. By carrying out in this temperature range, the triaryltriazine compound (2) can be obtained with good yield.

  The reaction time varies depending on the type of substrate, the type of solvent, and the reaction temperature, and is not particularly limited, but the reaction can usually be completed within a range of 1 hour to 24 hours.

  The reaction is preferably performed in an inert gas atmosphere such as nitrogen or argon, and can be performed at normal pressure or under pressure.

  After completion of the reaction, it can be generally treated by a known method, and can be isolated by a general purification method such as column chromatography or crystallization as necessary.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail using an Example, these Examples show the outline | summary of this invention and this invention is not limited to these Examples.

[measuring equipment]
The reaction yield and purity were calculated by HPLC (high performance liquid chromatography) analysis. Identification was performed by NMR. The apparatus used is shown below.

HPLC apparatus: Agilent 1120 Compact LC
Column: ZORBAX Eclipse XDB-C18 (5 μm, 4.6 mm ID × 250 mm)
Detector: SD-8022 UV-visible detector (measurement wavelength 254 nm)
NMR apparatus: Gemini 200 (300 MHz, manufactured by Varian)
Reference Example 1 (2,4- (diphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine)

  A 200 mL flask equipped with a thermometer and condenser was charged with 3-bromo-5-chlorobenzoic acid chloride (4.85 g, 19.1 mmol), benzonitrile (3.94 g, 38.2 mmol), and chlorobenzene (27 mL, 3- Bromo-5-chlorobenzoic acid chloride substrate concentration 0.70 mol / L) was charged and the internal temperature was cooled to 0 to 5 ° C., and then antimony pentachloride (5.7 g, 19.1 mmol) was added dropwise over 1 hour. . After completion of dropping, the mixture was aged at 100 ° C. for 5 hours and then cooled to 0 to 5 ° C. When the cooled reaction solution was dropped into a 28% aqueous ammonia solution (32 mL, 534 mmol) cooled to 0 to 5 ° C. over 1 hour, a white solid was precipitated. After completion of the dropwise addition, the mixture was further stirred at a temperature of 20 to 30 ° C. for 12 hours, and then filtered to obtain a white solid (20.8 g). After adding o-dichlorobenzene (164 mL) to the obtained white solid and dissolving by heating, the insoluble component is filtered off and recrystallized from the obtained filtrate to obtain 2,4- (diphenyl) which is the target product. A white solid (yield 3.87 g, yield 48%, purity 99.5%) of -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine was obtained. As a result of the purity measurement, no chloro adduct was detected.

¹ H-NMR (CDCl ₃ ): δ 8.76 (dd, J = 1.7, 1.5 Hz, 1H), 8.74 (dd, J = 7.2, 1.5 Hz, 4H), 8.66 (Dd, J = 1.9, 1.4 Hz, 1H), 7.74 (dd, J = 1.9, 1.7 Hz, 1H) 7.64 (tt, J = 7.2, 1.5 Hz, 2H), 7.59 (t, J = 7.2 Hz, 4H).

  Comparative Example 1 (2,4- (bisbiphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine)

  To a 200 mL flask with thermometer and condenser was added 3-bromo-5-chlorobenzoic acid chloride (4.85 g, 19.1 mmol), 4-cyanobiphenyl (6.84 g, 38.2 mmol), and chlorobenzene (77 mL, 3-bromo-5-chlorobenzoic acid chloride substrate concentration of 0.25 mol / L) was cooled to an internal temperature of 0-5 ° C., and then antimony pentachloride (5.7 g, 19.1 mmol) was added over 1 hour. It was dripped. After completion of dropping, the mixture was aged at 100 ° C. for 5 hours and then cooled to 0 to 5 ° C. When the cooled reaction solution was dropped into a 28% aqueous ammonia solution (32 mL, 534 mmol) cooled to 0 to 5 ° C. over 1 hour, a white solid was precipitated. The mixture was further stirred for 12 hours at a temperature of 20 to 30 ° C., and then filtered to obtain a white solid (23.9 g). After adding o-dichlorobenzene (328 mL) to the obtained white solid and dissolving with heating, the insoluble component was filtered off and recrystallized from the obtained filtrate to obtain 2,4- (bisbiphenyl) which is the target product. ) -6- (3-Bromo-5-chlorophenyl) -1,3,5-triazine as a white solid (yield 5.8 g, 53% yield, purity 98.4%, chloro adduct 1.2%) Obtained.

¹ H-NMR (CDCl ₃ ): δ 7.40-7.43 (m, 2H), 7.49-7.54 (m, 4H), 7.71-7.76 (m, 5H), 7 .83 (d, J = 8.1 Hz, 4H), 8.70 (brs, 1H), 8.82-8.85 (m, 5H).

Comparative Example 2
The same experimental operation as in Comparative Example 1 was performed except that the amount of chlorobenzene used was changed to 29 mL (substrate concentration of 3-bromo-5-chlorobenzoic acid chloride: 0.70 mol / L). White solid of 2,4- (bisbiphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine, the target product (yield 4.9 g, yield 45%, purity 97.8) %, Chloro adduct 1.6%).

Example 1
The same experimental operation as in Comparative Example 1 was carried out except that the aging temperature after dropping antimony pentachloride was changed to 55 ° C. White solid of 2,4- (bisbiphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine, which is the target product (yield 5.3 g, yield 48%, purity 99.6) %, Chloro adduct 0.2%).

Example 2
The same experimental operation as in Comparative Example 1 was carried out except that the aging temperature after dropping antimony pentachloride was changed to 25 ° C. 2,4- (Bisbiphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine, a white solid (yield 4.8 g, yield 44%, purity 99.5) %, Chloro adduct 0.3%).

Example 3
Comparative Example, except that the amount of chlorobenzene used was changed to 29 mL (3-bromo-5-chlorobenzoic acid chloride substrate concentration 0.70 mol / L), and the aging temperature after addition of antimony pentachloride was changed to 55 ° C. The same experimental procedure as 1 was performed. White solid of 2,4- (bisbiphenyl) -6- (3-bromo-5-chlorophenyl) -1,3,5-triazine, which is the target product (yield 5.8 g, 53% yield, purity 98.8) %, Chloro adduct 0.6%).

  The results of Reference Example 1, Examples 1 to 3 and Comparative Examples 1 and 2 are shown in Table 1.

  In Table 1, the chloro adducts in Examples 1 to 3 and Comparative Examples 1 and 2 are represented by the following formula (7).

The compound represented by these is represented. Moreover, the density | concentration (mol / L) in a table | surface represents the substrate concentration (mol / L) of the substrate applicable to the aromatic acid chloride represented by the said General formula (5).

Claims (6)

General formula (1)

(In the formula, Ar ¹ and Ar ² each independently represent an optionally substituted monocyclic, linked, or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms. X represents I, Br, Cl represents F or F. n represents an integer of 1 to 6.)
The halogen-added triaryltriazine compound represented by the formula (2) is contained in a range of 1.0% or less in terms of LC purity.

(In the formula, Ar ¹ and Ar ² have the same meaning as in the general formula (1).)
A triaryltriazine compound represented by the formula: Ar ² represents the following formula (3)

The triaryltriazine compound according to claim 1, wherein the triaryltriazine compound is represented by the formula: The triaryltriazine compound according to claim 1, wherein Ar ¹ is each independently a monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms. General formula (4)

(In the formula, Ar ¹ represents an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms.)
An aromatic nitrile compound represented by the general formula (5)

(In the formula, Ar ² represents an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 24 carbon atoms.)
Wherein an oxonium salt compound is produced in the presence of a transition metal halogen compound in the temperature range of 15 to 65 ° C., and the oxonium salt compound is further reacted with an amine source. The method for producing a triaryltriazine compound according to claim 1. The substrate concentration of the aromatic nitrile compound represented by the general formula (4) is 2.0 mol / L or less, and the substrate concentration of the aromatic acid chloride represented by the general formula (5) is 1.0 mol / L. The method for producing a triaryltriazine according to claim 4, wherein the triaryltriazine is L or less. 6. The method for producing a triaryltriazine according to claim 4, wherein the transition metal halogen compound is antimony chloride.