JP2003261519A - Method for producing triarylamine - Google Patents

Abstract

(57) [Summary] The present invention relates to an aryl bromide raw material and the like.
An object of the present invention is to suppress the production amount of a bisaryl derivative or a dehalogenated arene derivative, which is an impurity, and safely synthesize arylamines with high activity and high selectivity. In a reaction for synthesizing a triarylamine by reacting a monoarylamine with an aryl halide, a catalyst comprising an arylphosphine represented by the general formula [1] and a palladium compound in the presence of a base. A method for producing a triarylamine, which is used. General formula [1] (In the formula, R ^{1 to} R ⁹ each independently represent a hydrogen atom or the like. Ar ^{1 to} Ar ^{4 each} represent a substituted or unsubstituted aryl group.)

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing triarylamines.

[0002]

Triarylamines are very important compounds in the field of organic electroluminescence. Conventionally, a method for synthesizing a triarylamine from an arylamine and an aryl halide using a copper catalyst is known as a method for synthesizing a triarylamine (O Organic Chemistry Vol. 9, 179 (1972), Asakura Shoten, Experimental Chemistry Course Vol. 20, 284 (1992) Maruzen, etc.).

Recently, Nishiyama and Korie et al. Reported a method for synthesizing a triarylamine from an arylamine compound and an aryl halide (Tetrahedro).
nLett. , 39, 617 (1998), Tetra
hedron Lett. , 39, 2367 (199
8)). In this method, a triarylamine is synthesized from an arylamine and an aryl halide in the presence of a base using a catalyst composed of tri-t-butylphosphine and a palladium compound.

[0004]

However, in the method using a copper catalyst, the yield of the product triarylamines is low because of the use of a large amount of copper catalyst and the need for a high reaction temperature. There was a flaw. Further, there is also a problem that it is difficult to purify the triarylamines from the reaction system because the product is strongly colored.

Further, in the method using tri-t-butylphosphine and a palladium compound as a catalyst, tri-t-butylphosphine may spontaneously ignite in the air, so that it is necessary to handle it with extreme caution. Further, the melting point of tri-t-butylphosphine is 30 ° C., and it is a glassy solid at a temperature of 25 ° C. or lower at which synthesis is usually performed, and it is very inconvenient to handle.

[0006]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that aryl bromide, aryl iodide, and aryl bromide can be obtained by using a catalyst containing an arylphosphine and a palladium compound.
It was found that the production amount of the bisaryl derivative or the dehalogenated arene derivative, which is an impurity, can be suppressed from the aryl chloride and further the aryl fluoride raw material, and the highly active and highly selective arylamines can be safely synthesized, The present invention has been completed.

That is, the present invention comprises an arylphosphine represented by the general formula [1] and a palladium compound in the presence of a base in the reaction of reacting a monoarylamine with an aryl halide to synthesize a triarylamine. The present invention relates to a method for producing triarylamines, which comprises using a catalyst consisting of General formula [1]

[Chemical 3] (In the formula, R ^{1 to} R ⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted N,
An N-dialkylamino group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. However, adjacent substituents, or R ⁴ and R ⁵ may be bonded to each other to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle. Ar ^{1 to} Ar ⁴ represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. ) Further, the present invention comprises an arylphosphine represented by the general formula [1] and a palladium compound in the presence of a base in a reaction for reacting a diarylamine and an aryl halide to synthesize a triarylamine. The present invention relates to a method for producing triarylamines, which is characterized by using a catalyst. General formula [2]

[Chemical 4] (In the formula, R ^{1 to} R ⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted N,
An N-dialkylamino group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. However, adjacent substituents, or R ⁴ and R ⁵ may be bonded to each other to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle. Ar ^{1 to} Ar ⁴ represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. ) Further, in the present invention, the arylphosphines are bis (2-
It relates to a method for producing the above triarylamines, which is diphenylphosphinophenyl) ether.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.

The aryl halide used in the present invention is an aryl chloride, an aryl bromide, an aryl iodide or an aryl fluoride, and is not particularly limited, but the aryl group may be, for example, an alkyl group in addition to a halogen atom. It may have a substituent such as a group, an alkoxy group, a phenoxy group, a trifluoromethyl group and an acyl group. In the present invention, the aryl group also contains a condensed cyclic hydrocarbon group.

The aryl halide used in the present invention is not particularly limited, but specifically, bromobenzene, o-bromotoluene, m-bromotoluene, p-bromotoluene, 2-bromo-m. -Xylene,
2-bromo-p-xylene, 3-bromo-o-xylene, 4-
Bromo-o-xylene, 4-bromo-m-xylene, 5-bromo-m-xylene, o-bromoanisole, m-bromoanisole, p-bromoanisole, o-bromophenol,
m-bromophenol, p-bromophenol, 1-bromo-2,4-dimethoxybenzene, 1-bromo-2,5-dimethoxybenzene, 2-bromobenzotrifluoride, 3-
Bromobenzotrifluoride, 4-bromobenzotrifluoride, 2-bromophenethyl alcohol, 3-bromophenethyl alcohol, 4-bromophenethyl alcohol,
5-bromo-1,2,4-trimethylbenzene, 1-bromo
-3- (trifluoromethoxy) benzene, 1-bromo-4
-(Trifluoromethoxy) benzene, 2-bromobiphenyl, 3-bromobiphenyl, 4-bromobiphenyl, 4
-Bromo-1,2- (methylenedioxy) benzene, 1-bromonaphthalene, 2-bromonaphthalene, 1-bromo-2-
Methylnaphthalene, 1-bromo-4-methylnaphthalene,
Aryl bromides such as 9-bromoanthracene, 9-bromo-2-methoxyanthracene, 9-bromo-10-phenylanthracene; chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene,
2-chloro-m-xylene, 2-chloro-p-xylene, 3-
Chloro-o-xylene, 4-chloro-o-xylene, 4-chloro-m-xylene, 5-chloro-m-xylene, o-chloroanisole, m-chloroanisole, p-chloroanisole, o-chlorophenol, m-chlorophenol, p-
Chlorophenol, 1-chloro-2,4-dimethoxybenzene, 1-chloro-2,5-dimethoxybenzene, 2-chlorobenzotrifluoride, 3-chlorobenzotrifluoride, 4-chlorobenzotrifluoride, 2 -Chlorophenethyl alcohol, 3-chlorophenethyl alcohol, 4-chlorophenethyl alcohol, 5-chloro-1,2,4-trimethylbenzene, 1-chloro-3- (trifluoromethoxy) benzene, 1-chloro-4- ( Trifluoromethoxy) benzene, 2-chlorobiphenyl, 3-chlorobiphenyl, 4-chlorobiphenyl, 4-chloro-1,2- (methylenedioxy) benzene, 1-chloronaphthalene, 2-chloronaphthalene, 1-chloro- 2-methylnaphthalene, 1-
Aryl chlorides such as chloro-4-methylnaphthalene, 9-chloroanthracene, 9-chloro2-methoxyanthracene, 9-chloro10-phenylanthracene; iodobenzene, o-iodotoluene, m-iodotoluene, p-iodotoluene. 2-iodo-m-xylene,
2-iodo-p-xylene, 3-iodo-o-xylene, 4-
Iodo-o-xylene, 4-iodo-m-xylene, 5-iodo-m-xylene, o-iodoanisole, m-iodoanisole, p-iodoanisole, o-iodophenol,
m-iodophenol, p-iodophenol, 1-iodo-2,4-dimethoxybenzene, 1-iodo-2,5-dimethoxybenzene, 2-iodobenzotrifluoride, 3-
Iodobenzotrifluoride, 4-iodobenzotrifluoride, 2-iodophenethyl alcohol, 3-iodophenethyl alcohol, 4-iodophenethyl alcohol,
5-iodo-1,2,4-trimethylbenzene, 1-iodo
-3- (trifluoromethoxy) benzene, 1-iodo-4
-(Trifluoromethoxy) benzene, 2-iodobiphenyl, 3-iodobiphenyl, 4-iodobiphenyl, 4
-Iodo-1,2- (methylenedioxy) benzene, 1-iodonaphthalene, 2-iodonaphthalene, 1-iodo-2-
Methylnaphthalene, 1-iodo-4-methylnaphthalene,
Aryl iodides such as 9-iodoanthracene, 9-iodo2-methoxyanthracene and 9-iodo10-phenylanthracene; fluorobenzene, o-fluorotoluene, m-fluorotoluene, p-fluorotoluene, 2-fluoro-m -Xylene, 2-fluoro-p-xylene, 3-fluoro-o-xylene, 4-fluoro-o-xylene, 4-fluoro-m-xylene, 5-fluoro-m-xylene, o-fluoroanisole, m- Fluoroanisole, p-fluoroanisole, o-fluorophenol,
m-fluorophenol, p-fluorophenol, 1-
Fluoro-2,4-dimethoxybenzene, 1-fluoro-
2,5-dimethoxybenzene, 2-fluorobenzotrifluoride, 3-fluorobenzotrifluoride, 4-fluorobenzotrifluoride, 2-fluorophenethyl alcohol, 3-fluorophenethyl alcohol, 4-fluorophenethyl alcohol, 5 -Fluoro-1,2,4-trimethylbenzene, 1-fluoro-3- (trifluoromethoxy) benzene, 1-fluoro-4- (trifluoromethoxy) benzene, 2-fluorobiphenyl, 3-fluorobiphenyl, 4- Fluorobiphenyl, 4-fluoro-1,
2- (methylenedioxy) benzene, 1-fluoronaphthalene, 2-fluoronaphthalene, 1-fluoro-2-methylnaphthalene, 1-fluoro-4-methylnaphthalene, 9-
Examples include arylfluorides such as fluoroanthracene, 9-fluoro-2-methoxyanthracene, and 9-fluoro10-phenylanthracene.

Further, 1,2-dibromobenzene, 1,3-
Dibromobenzene, 1,4-dibromobenzene, 9,1
0-dibromoanthracene, 9,10-dichloroanthracene, 4,4'-dibromobiphenyl, 4,4'-dichlorobiphenyl, 4,4'-iodobiphenyl, 1-bromo
-2-Fluorobenzene, 1-Bromo-3-fluorobenzene, 1-Bromo-4-fluorobenzene, 2-Bromochlorobenzene, 3-Bromochlorobenzene, 4-Bromochlorobenzene, 2-Bromo-5-chlorotoluene, 3- Bromo-
4-chlorobenzotrifluoride, 5-bromo-2-chlorobenzotrifluoride, 1-bromo-2,3-dichlorobenzene, 1-bromo-2,6-dichlorobenzene, 1-bromo-
3,5-dichlorobenzene, 2-bromo-4-fluorotoluene, 2-bromo-5-fluorotoluene, 3-bromo-4-
Fluorotoluene, 4-bromo-2-fluorotoluene,
An aryl halide having two or more halogen atoms such as 4-bromo-3-fluorotoluene can also be exemplified as the aryl halide used in the present invention.

As the monoarylamines and diarylamines used in the present invention, in addition to general aromatic amines, metal amides and the like can be used.

The monoarylamines are not particularly limited, but for example, aniline, o-fluoroaniline, m-fluoroaniline, p-fluoroaniline, o-anisidine, m-anisidine, p-anisidine,
o-toluidine, m-toluidine, p-toluidine, 1-
Examples thereof include aromatic primary amines such as naphthylamine, 2-naphthylamine, 2-aminobiphenyl, and 4-aminobiphenyl.

Further, 1,2-phenylenediamine, 1,3
-Phenylenediamine, 1,4-phenylenediamine,
Monoarylamines having two or more aromatic primary amino groups such as 1,5-diaminonaphthalene, 1,8-diaminonaphthalene and 2,3-diaminonaphthalene are also exemplified as the monoarylamine used in the present invention. be able to.

The diarylamines are not particularly limited, and examples thereof include diphenylamine and di-o.
-Tolylamine, di-m-tolylamine, di-p-tolylamine, bis (2-methoxyphenyl) amine, bis (3-methoxyphenyl) amine, bis (4-methoxyphenyl) amine, N-phenyl-o-tolylamine,
N-phenyl-m-tolylamine, N-phenyl-p-
Trilylamine, N-phenyl-2-methoxyamine, N
-Phenyl-3-methoxyamine, N-phenyl-4-
Methoxyamine, N-phenyl-1-naphthylamine,
Examples thereof include diphenylamine derivatives such as N-phenyl-2-naphthylamine.

Diarylamines having two or more aromatic secondary amino groups such as N, N'-diphenyl-p-phenylenediamine and N, N'-di-2-naphthyl-p-phenylenediamine are also included in the present invention. It can be exemplified as the diarylamine used in the invention.

Although the metal amides are not particularly limited, examples thereof include aminotin compounds and aminoborane compounds, which can be synthesized by a known method. For example, an aminotin compound can be synthesized by heating (N, N-diethylamino) tributyltin and the corresponding primary amine or secondary amine in toluene under argon. The aminoborane compound can be synthesized from primary amines or secondary amines corresponding to tris (diethylamino) borane.

In the present invention, the amine compound is reacted in an amount of 0.1 mol to an excess of 1 mol of the aryl halide, or 0.1 mol to an excess of 1 mol of a halogen atom on the ring of the aryl halide. If it exists in the system,
Since the unreacted amine compound becomes complicated to recover, it is more preferably in the range of equimolar to 30 times the molar amount of the aryl halide, or equimolar to 1 mol of the halogen atom on the ring of the aryl halide. It may be present in the reaction system in a 60-fold molar range.

The palladium compound used in the present invention is not particularly limited, but for example, tetravalent palladium compounds such as sodium hexachloropalladium (IV) tetrahydrate, potassium hexachloropalladium (IV) acid, etc., Palladium (II) chloride, palladium (II) bromide, palladium (II) acetate, palladium acetylacetonate (II), dichlorobis (benzonitrile) palladium (II), dichlorobis (acetonitrile) palladium (II), dichlorobis (triphenyl) Phosphine) palladium (II), dichlorotetraamminepalladium (II), dichloro (cycloocta-
Divalent palladium compounds such as 1,5-diene) palladium (II) and palladium trifluoroacetate (II), tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium chloroform complex (0 ), Tetrakis (triphenylphosphine) palladium (0), and other zero-valent palladium compounds.

In the present invention, the amount of the palladium compound used is not particularly limited, but is usually 0.000001 to 0.001 in terms of palladium based on 1 mol of the aryl halide.
It is in the range of 20 mol%. If the palladium compound is within the above range, arylamines can be synthesized with a high selectivity, but in order to further improve the activity, a more preferable amount of the palladium compound is used because an expensive palladium compound is used. Is in the range of 0.0001 to 10 mol% in terms of palladium with respect to 1 mol of the aryl halide.

In the present invention, the arylphosphines used in combination with the palladium compound are those represented by the general formula [1], for example, bis (2-
Diphenylphosphinophenyl) ether, 9,9-dimethyl-4,5-bis (diphenylphosphino) xanthene, 2,8-dimethyl-4,6-bis (diphenylphosphino) phenoxatin, 6,8-bis (diphenyl) Phosphino) benzo [kl] xanthene, 4,6-bis (diphenylphosphino) -10,11-dihydrodibenzo [b,
f] oxepin, 4,6-bis (diphenylphosphino)
Examples thereof include dibenzofuran. Among them, in order to improve the selectivity of arylamines, bis (2
-Diphenylphosphinophenyl) ether is more preferred.

In the present invention, the amount of the arylphosphine used is usually 0.01 to 1 with respect to the palladium compound.
It may be used in the range of 0000 times mol. If the amount of the arylphosphines used is within the above range, the selectivity of the arylamines does not change, but in order to further improve the activity, also from the use of expensive arylphosphines, A more preferable amount of arylphosphine used is in the range of 0.1 to 10 times by mole with respect to the palladium compound.

In the present invention, the palladium compound and the arylphosphine are essential, and they are combined and added as a catalyst to the reaction system. The addition method may be added to the reaction system alone, or may be added in the form of a complex in advance.

The base used in the present invention includes
It may be selected from an inorganic base and / or an organic base and is not particularly limited, but more preferably sodium.
-Methoxide, sodium-ethoxide, potassium-methoxide, potassium-ethoxide, lithium-tert-butoxide, sodium-tert-butoxide, potassium
Alkali metal alkoxides such as -tert-butoxide, which can be added to the reaction field as they are, or prepared in situ from alkali metal, alkali metal hydride or alkali metal hydroxide and alcohol, and then added to the reaction field. May be offered.

The amount of the base used is preferably 0.5 times or more mol based on the hydrogen halide produced in the reaction. When the amount of the base is less than 0.5 times by mole, the yield of arylamines may be low. Although the yield of arylamines does not change even if the base is added in a large excess, the post-treatment operation after the reaction is complicated, so the more preferable amount of the base is in the range of 1 to 5 times by mole. .

The reaction in the present invention is usually carried out in the presence of an inert solvent. The solvent used is not particularly limited as long as it is a solvent that does not significantly inhibit the reaction, and is not particularly limited, but aromatic solvents such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, etc. Ether type organic solvent, acetonitrile,
Examples thereof include dimethylformamide, dimethylsulfoxide, hexamethylphosphotriamide and the like. Of these, more preferred are aromatic organic solvents such as benzene, toluene and xylene.

The present invention can be carried out under normal pressure, under an atmosphere of an inert gas such as nitrogen or argon, or under pressure.

The present invention is carried out at a reaction temperature of 20 ° C to 300 ° C, more preferably 50 ° C to 200 ° C.

In the present invention, the reaction time is not constant depending on the amounts of aryl halide, amine compound, base, palladium compound and trialkylphosphine and the reaction temperature, but may be selected from the range of several minutes to 72 hours.

After the completion of the reaction, the desired compound can be obtained by a conventional method.

[0031]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. The yields shown below were calculated based on the aryl halide used as the raw material.

Example 1 30 equipped with a cooling pipe, a thermometer, and a blade-type stirring rod
After putting 100 mL of toluene into a 0 mL four-necked flask and flowing nitrogen for about 10 minutes, diphenylamine 21.1 was added.
2 g, p-bromotoluene 17.79 g, palladium acetate 0.58 g, bis (2-diphenylphosphinophenyl) ether 2.80 g, sodium t-butoxy 1
Add 4.01 g in order and heat to 110 ° C under nitrogen stream 3
Stir for hours. After completion of the reaction, the reaction solution was cooled to about 40 ° C. and transferred to a separating funnel. Add 50 mL of water to this
After adding and shaking for about 5 minutes, the organic layer was separated. Further, the organic phase was separated by shaking twice with 50 mL of water, and the organic phase was dried over magnesium sulfate. After magnesium sulfate was filtered off, the desired product was separated by column chromatography (silica gel, toluene) and recrystallized from methanol to obtain 25.24 g of desired 4-tolyldiphenylamine. The yield at this time was 78%.

Example 2 Bis (2-diphenylphosphinophenyl) ether was added to 9,9-dimethyl-4,5-bis (diphenylphosphino)
The same operation as in Example 1 was carried out except that the amount of xanthene was changed to 3.01 g to obtain 18.45 g of the desired 4-tolyldiphenylamine. At this time, the yield was 57%.

Example 3 p-Bromotoluene was added to 4-bromoanisole 19.45.
The same operation as in Example 1 was carried out except that the amount of 4-methoxyphenyldiphenylamine 28.
55 g was obtained. At this time, the yield was 83%.

Example 4 p-Bromotoluene was added to 4-bromobiphenyl 24.24.
The same operation as in Example 1 was carried out except that the amount was changed to g to obtain 26.20 g of the desired biphenyldiphenylamine. At this time, the yield was 65%.

Example 5 20 equipped with a cooling pipe, a thermometer, and a blade-type stirring rod
58 g of toluene was put into a 0 mL four-necked flask, and nitrogen was circulated for about 10 minutes, and then 1-aminonaphthalene 1.61 was added.
g, p-bromotoluene 4.23 g, sodium t-butoxide 2.59 g, palladium acetate 0.126 g, bis
(2-diphenylphosphinophenyl) ether 1.21
g were sequentially added, and the mixture was heated to 110 ° C. under a nitrogen stream and stirred for 3 hours. After completion of the reaction, the reaction solution was cooled to about 40 ° C. and transferred to a separating funnel. After adding 50 mL of water to this and shaking for about 5 minutes, the organic phase was separated. Further, the organic phase was separated by shaking twice with 50 mL of water, and the organic phase was dried over magnesium sulfate. After removing magnesium sulfate by filtration, column chromatography (silica gel, toluene)
The desired product was separated by and recrystallized with methanol to obtain 2.34 g of the desired ditolylnaphthylamine. The yield at this time was 65%.

Example 6 4.63 g of 4-bromoanisole was added to p-bromotoluene.
The same operation as in Example 5 was performed except that the target bis (4-methoxyphenyl) naphthylamine was changed to 2.
94 g were obtained. At this time, the yield was 73%.

Comparative Example 1 The same procedure as in Example 1 was repeated except that the bis (2-diphenylphosphinophenyl) ether was changed to 1.05 g of tri-t-butylphosphine which is a trialkylphosphine. Pretreatment was required. Tri-t-butylphosphine was liquefied by heating with hot air or a water bath under a nitrogen stream. Liquid tri-t-butylphosphine 1.
Weigh 05 g, add 10 mL of toluene, and add t-
A toluene solution of butylphosphine was prepared.

As described above, the birds adjusted in advance
Example 1 using a toluene solution of t-butylphosphine
The same operation as above was performed to obtain 22.01 g of desired 4-tolyldiphenylamine. The yield at this time was 68%.

[0040]

INDUSTRIAL APPLICABILITY According to the present invention, triarylamines are safer, simpler, and more active by using a catalyst composed of an aryl halide and an amine compound in the presence of a base, and an arylphosphine and a palladium compound.・ Since it can be synthesized with high selectivity, it is extremely meaningful industrially.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) // C07B 61/00 300 C07B 61/00 300 F term (reference) 4H006 AA02 AC52 BA25 BA30 BA45 BA53 BB11 BB61 4H039 CA71 CD10 CD20

Claims (3)

[Claims] 1. A catalyst comprising an arylphosphine represented by the general formula [1] and a palladium compound in the presence of a base in a reaction for synthesizing a triarylamine by reacting a monoarylamine and an aryl halide. A process for producing triarylamines, which comprises using General formula [1] (In the formula, R ^{1 to} R ⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted N,
An N-dialkylamino group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. However, adjacent substituents, or R ⁴ and R ⁵ may be bonded to each other to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle. Ar ^{1 to} Ar ⁴ represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. ) 2. A catalyst comprising an arylphosphine represented by the general formula [1] and a palladium compound in the presence of a base in the reaction for reacting a diarylamine and an aryl halide to synthesize triarylamines. A method for producing triarylamines, which comprises using the same. General formula [2] (In the formula, R ^{1 to} R ⁸ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted N,
An N-dialkylamino group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. However, adjacent substituents, or R ⁴ and R ⁵ may be bonded to each other to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocycle. Ar ^{1 to} Ar ⁴ represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. ) 3. The method for producing triarylamines according to claim 1 or 2, wherein the arylphosphine is bis (2-diphenylphosphinophenyl) ether.