JP7624812B2 - Triazine compounds having a xanthenyl group - Google Patents

Description

This disclosure relates to a triazine compound, a method for producing the same, and a material for an organic electroluminescent device.

Organic electroluminescent devices have started to be put to practical use, mainly for small mobile devices. Although recent organic electroluminescent devices have been gradually improved, further performance improvements are required. In particular, there is a strong demand for longer life from the viewpoint of expanding the range of applications of organic electroluminescent devices.
Moreover, organic electroluminescent devices are beginning to be put to practical use in applications other than small mobile applications, for example, as in-vehicle display devices.

Patent Document 1 discloses a triazine compound having a specific structure as an electron transport material. According to Patent Document 1, the triazine compound can provide an organic electroluminescent device with excellent life, voltage, or luminous efficiency.

Patent No. 6464944

However, there is a very strong demand from the market for an expansion of applications, and the triazine compound in Patent Document 1 does not fully meet these demands in terms of extending the device life, so further improvements are required.

Therefore, one aspect of the present invention is directed to providing a triazine compound and a material for an organic electroluminescent element that contribute to the production of an organic electroluminescent element that can exhibit an excellent element life, as well as a method for producing the triazine compound.
Another aspect of the present invention is directed to providing an organic electroluminescent device that can exhibit an excellent device life.

The triazine compound according to one embodiment of the present disclosure is represented by formula (1):

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atom,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two ^R2 may be joined together to form a 5- or 6-membered ring, including the carbon atom to which they are attached;
R ³ may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
When p is 2, two L's may be different from each other.

A method for producing a triazine compound represented by formula (1) according to another aspect of the present disclosure includes a coupling reaction between a compound represented by formula (2) and a compound represented by formula (3):

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two ^R2 's may be joined together to form a 5- or 6-membered ring, including the carbon atom to which they are bonded;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
^M1 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^Y1 and ^Y2 each independently represent a chlorine atom, a bromine atom, or an iodine atom;
Each ^Y3 independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group;
Each ^Y4 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group;
The two (OY ⁴ ) groups may be joined together to form a ring with the boron atom;
^X1 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group or an iodine atom.

A method for producing a triazine compound represented by formula (1) according to another aspect of the present disclosure includes a coupling reaction between a compound represented by formula (4) and a compound represented by formula (5):

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
In addition, two R2 ^'s may be joined together to form a 5- or 6-membered ring, including the carbon atom to which they are bonded;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
^X2 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom;
^M2 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^Y1 and ^Y2 each independently represent a chlorine atom, a bromine atom, or an iodine atom;
Each ^Y3 independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group;
Each ^Y4 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group;
The two (OY ⁴ ) groups may be joined together to form a ring with the boron atom.

A material for organic electroluminescent devices according to another embodiment of the present disclosure contains the above-mentioned triazine compound.
An organic electroluminescent device according to another embodiment of the present disclosure contains the above-mentioned triazine compound.

According to one aspect of the present disclosure, it is possible to provide a triazine compound and a material for an organic electroluminescent element that contribute to the production of an organic electroluminescent element that achieves an excellent element life, as well as a method for producing the triazine compound.
According to another aspect of the present disclosure, it is possible to provide an organic electroluminescent device that achieves an excellent device life.

FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescence element according to one embodiment of the present disclosure. FIG. 2 is a schematic cross-sectional view showing another example of a laminate structure of an organic electroluminescence element according to one embodiment of the present disclosure (structure of element example 1).

The triazine compound according to one embodiment of the present disclosure will be described in detail below.
The triazine compound according to one embodiment of the present disclosure is represented by formula (1):

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atom,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two ^R2 may be joined together to form a 5- or 6-membered ring, including the carbon atom to which they are attached;
R ³ may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
When p is 2, two L's may be different from each other.

The inventors speculate that the above problem can be solved by introducing a xanthenyl group into an appropriate position in the molecule of a triazine compound having a structure as shown in formula (1), thereby improving durability against holes.

Hereinafter, the triazine compound according to one embodiment of the present disclosure (hereinafter, also simply referred to as triazine compound (1)) will be described in more detail.
The triazine compound (1) is represented by any one of formulas (1a), (1b), (1c), and (1d).

In formulas (1a) to (1d), Ar ¹ , Ar ² , R ¹ , R ² , R ³ , L, Z and p are the same as those in formula (1).

In terms of ease of synthesis of the triazine compound (1), the compound represented by formula (1a) is preferred.
The definitions of Ar ¹ , Ar ² , R ¹ , R ² , R ³ , L, Z and p in the triazine compound (1) will be explained below.

[Regarding Ar ¹ and Ar ² ]
^Ar1 and ^Ar2 each independently represent a phenyl group, a biphenylyl group, or a naphthyl group. ^Ar1 and ^Ar2 each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group.
In view of the excellent electron transporting material properties of the triazine compound (1), it is preferable that Ar ¹ and Ar ² each independently represent a phenyl group or a biphenylyl group.
From the viewpoint of ease of synthesis of the triazine compound (1), it is preferable that Ar ¹ and Ar ² are the same group.

[Regarding ^R1 ]
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
It represents a nitrogen-containing heterocyclic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
^R1 is
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
It is preferably a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.

Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, and a fluoranthenyl group. In terms of ease of synthesis of the triazine compound (1), R ¹ is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms, more preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthrenyl group, and particularly preferably a phenyl group or a biphenylyl group.

Nitrogen-Containing Heterocyclic Group Examples of the nitrogen-containing heterocycle include a pyridyl group, a piperidyl group, a benzo[b]quinolyl group, a phenylpyridyl group, and a carbazolyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device, it is preferable that R ¹ is a pyridyl group, a dimethylpyridyl group, or a phenylpyridyl group.

[Regarding ^R2 ]
R ² may be the same or different;
a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or
It represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
It is preferable that at least one of ^R2 is an alkyl group having 1 to 6 carbon atoms.

The alkyl group having 1 to 6 carbon atoms may be, for example, any of linear, branched, and cyclic alkyl groups, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, a cyclobutyl group, etc. From the viewpoint of ease of synthesis of the triazine compound (1), it is preferable that R ² is a methyl group.

Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, and a fluorenyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In terms of ease of synthesis of the triazine compound (1), it is preferable that R ² is an unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms substituted with a methyl group, and a phenyl group is particularly preferable.

In addition, two ^R2 may form a 5- or 6-membered ring together with the carbon atom to which they are bonded. Examples of the 5- or 6-membered ring include cyclopentane, cyclopentene, cyclopentadiene, cyclohexyl, cyclohexene, and 1,4-cyclohexadiene. In terms of ease of synthesis of triazine compound (1), it is preferable that the 5- or 6-membered ring is cyclopentane or cyclohexane.

[Regarding ^R3 ]
R ³ is the same or different,
a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or
It represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
R ³ is the same or different,
A hydrogen atom, or
An alkyl group having 1 to 6 carbon atoms is preferred.

The alkyl group having 1 to 6 carbon atoms may be, for example, any of linear, branched, and cyclic alkyl groups, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, a cyclobutyl group, etc. From the viewpoint of ease of synthesis of the triazine compound (1), it is preferable that R ³ is a methyl group.

Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, and a fluorenyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In terms of ease of synthesis of the triazine compound (1), it is preferable that R ³ is a phenyl group.

In addition, two ^R3 may form a 5- or 6-membered ring together with the carbon atom to which they are bonded. Examples of the 5- or 6-membered ring include cyclopentane, cyclopentene, cyclopentadiene, cyclohexyl, cyclohexene, cyclohexadiene, and benzene. In terms of ease of synthesis of the triazine compound (1), it is preferable that the 5- or 6-membered ring is cyclopentane or benzene.

[Regarding Z]
Z represents an oxygen atom or a sulfur atom. Z is preferably an oxygen atom in that the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance.

[About L]
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms.
Examples of the phenylene group include an orthophenylene group, a metaphenylene group, and a paraphenylene group. In order that the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance, it is preferable that L is a metaphenylene group or a paraphenylene group which may be substituted with a phenyl group, a naphthyl group, or an alkyl group having 1 to 4 carbon atoms.

[Regarding p]
p represents 0, 1 or 2;
When p is 2, the two Ls may be different from each other. p is preferably 0 or 1, since the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance.

[Specific examples of triazine compound (1)]
Specific examples of the triazine compound (1) are not particularly limited, but include compounds having structures represented by the following formulas (1-1) to (1-165).

Next, a method for producing a triazine compound according to another embodiment of the present disclosure (hereinafter, referred to as a method for producing triazine compound (1)) will be described.
The triazine compound (1) can be produced by step 1 or 2 shown in the following reaction scheme.
That is, the method for producing the triazine compound (1) is as follows:
or comprising subjecting a compound represented by formula (2) and a compound represented by formula (3) to a coupling reaction.
The method includes subjecting a compound represented by formula (4) and a compound represented by formula (5) to a coupling reaction.

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
In addition, two R2 ^'s may be joined together to form a 5- or 6-membered ring, including the carbon atom to which they are bonded;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
When p is 2, two L's may be different from each other.
^M1 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^M2 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^Y1 and ^Y2 each independently represent a chlorine atom, a bromine atom, or an iodine atom;
Each ^Y3 independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group;
Each ^Y4 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group;
X ¹ represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom;
^X2 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom;
The two (OY ⁴ ) groups may be joined together to form a ring with the boron atom.
It is preferred that ^M1 or ^M2 is B( ^OY4 ) ₂ .

Step 1 is a step of producing triazine compound (1) by coupling reaction of triazine compound (2) and compound (3) in the presence of a catalyst as necessary. In step 1, the target product can be obtained in good yield by applying reaction conditions for general coupling reactions such as the Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, and Stille reaction. When applying reaction conditions for the Suzuki-Miyaura reaction to step 1, it is preferable to carry out the reaction in the presence of a base. In addition, a palladium catalyst is preferable as the catalyst.

The compound represented by formula (2) used in step 1 can be synthesized, for example, by the method disclosed in Japanese Patent No. 5,312,824, or by a reaction for synthesizing a general organometallic compound from a compound represented by formula (4) (see, for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363).
Examples of the compound represented by formula (2) include compounds having structures shown in the following formulas (2-1) to (2-95), but the present invention is not limited thereto. In formulas (2-1) to (2-95), ^M1 has the same definition as in formula (2).

The group represented by ^M1 is not particularly limited, but examples thereof include ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , and B( ^OY4 )2 in which two ( ^OY4 ) groups may be combined together to form a ring with a boron atom. Among these, B( ^OY4 ) _{2 is} preferred.

ZnY ¹ and MgY ² are not particularly limited, but examples thereof include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI.
Sn(Y ³ ) ₃ is not particularly limited, but examples thereof include Sn(Me) ₃ and Sn(Bu) ₃ .
Examples of B(OY ⁴ ) ₂ include, but are not limited to, B(OH) ₂ , B(OMe) ₂ , B(O ⁱ Pr) ₂ , B(OBu) ₂ , and B(OPh) ₂ . Me represents a methyl group, ⁱ Pr represents an isopropyl group, Bu represents a butyl group, and Ph represents a phenyl group. Examples of B(OY ⁴ ) ₂ in which two (OY ⁴ ) groups are united to form a ring with a boron atom include, but are not limited to, the following groups (I) to (VI), with the group (II) being preferred in terms of good yield.

The compound (3) used in step 1 can be produced, for example, according to the method of Japanese Patent No. 6023635. Alternatively, a commercially available product may be used.
Examples of compound (3) include the following formulas (3-1) to (3-12), but the present invention is not limited thereto. In formulas (3-1) to (3-12), ^X1 has the same definition as in formula (3).

The leaving group represented by ^X1 is not particularly limited, but examples thereof include a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, and an iodine atom, and a chlorine atom or a bromine atom is preferred in terms of the yield of the triazine compound (1). However, in terms of the availability of raw materials, it may be preferable to use a trifluoromethanesulfonyloxy group.

The palladium catalyst that can be used in step 1 is not particularly limited, but specifically includes
Palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate;
Complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, and dichlorobis(benzonitrile)palladium; and
Palladium complexes having a tertiary phosphine as a ligand, such as dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, and dichlorobis(tricyclohexylphosphine)palladium;
Examples include:

Palladium complexes having a tertiary phosphine as a ligand can also be prepared in the reaction system by adding a tertiary phosphine to a palladium salt or complex compound. Examples of tertiary phosphines that can be used in this case include triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, bis(diphenylphosphine), and tert-butyldiphenylphosphine. Examples include 2-dicyclohexylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, tri(2-furyl)phosphine, tri(o-tolyl)phosphine, tris(2,5-xylyl)phosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl.

Among these, palladium complexes having a tertiary phosphine as a ligand are preferred because of their good yield, and palladium complexes having 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or triphenylphosphine as a ligand are even more preferred.

The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:2 to 3:1 in terms of good yield. There is no limit to the amount of palladium catalyst used in step 1, but in terms of good yield, it is preferable that the molar equivalent of the palladium catalyst be in the range of 0.005 to 0.5 molar equivalents relative to the boron compound.

The base used in step 1 is not particularly limited, but examples thereof include metal hydroxide salts such as sodium hydroxide, potassium hydroxide, calcium hydroxide, etc.; metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, etc.; metal acetates such as potassium acetate, sodium acetate, etc.; metal phosphates such as potassium phosphate, sodium phosphate, etc.; metal fluoride salts such as sodium fluoride, potassium fluoride, cesium fluoride, etc.; metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, potassium tert-butoxide, etc. Among these, metal carbonates and metal phosphates are preferred in terms of good reaction yield, and potassium carbonate or potassium phosphate is more preferred. There is no particular limit to the amount of base, but in terms of good reaction yield, the molar ratio of the base to the boron compound is preferably in the range of 1:2 to 10:1, and more preferably in the range of 1:1 to 4:1.

Step 1 can be carried out in a solvent, and examples of the solvent include water; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone. Examples of the solvent include esters such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU), N,N'-dimethylpropyleneurea (DMPU), and alcohols such as dimethylsulfoxide (DMSO), methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and the like. These may be mixed in any ratio. There is no particular limit to the amount of solvent used. Among these, water, ethers, amides, alcohols, or mixed solvents thereof are preferred in terms of good reaction yield, and a mixed solvent of THF and water is more preferred.

Step 1 can be carried out at a temperature appropriately selected from 0° C. to 200° C., and is preferably carried out at a temperature appropriately selected from 40° C. to 150° C. in terms of good reaction yield.
The product of step 1 can be obtained by carrying out a normal treatment after completion of the reaction. If necessary, it may be purified by recrystallization, column chromatography, sublimation, preparative HPLC, or the like.

Next, step 2 will be described.
Step 2 is a step of producing triazine compound (1) by coupling reaction of a compound represented by formula (4) with a compound represented by formula (5) in the presence of a catalyst as necessary. In step 2, the target product can be obtained in good yield by applying reaction conditions for general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc. When the reaction conditions for the Suzuki-Miyaura reaction are applied to step 2, it is preferable to carry out the reaction in the presence of a base. In addition, a palladium catalyst is preferable as the catalyst.

The triazine compound represented by formula (4) used in step 2 can be produced, for example, according to the method disclosed in JP-A-2018/115151.
Examples of the triazine compound represented by formula (4) include compounds in which M ¹ in formulas (2-1) to (2-95), which are specific examples of the compound represented by formula (2), is replaced with X ^2. Here, X ² has the same meaning as in formula (4).

The leaving group represented by ^X2 is not particularly limited, but examples thereof include a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, and an iodine atom. In terms of the good yield of the triazine compound (1), a chlorine atom or a bromine atom is preferred.

The compound represented by formula (5) used in step 2 can be produced, for example, according to U.S. Patent Publication No. 2014/0239279. It can also be synthesized from the compound represented by formula (3) using a reaction for synthesizing a general organometallic compound (for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363), or a commercially available product may be used.

The compound represented by formula (5) can be exemplified by a skeleton in which ^X1 in the compounds represented by formulas (3-1) to (3-12) is replaced with ^M2 . ^M2 has the same definition as in formula (5).

The palladium catalyst, base, solvent, reaction temperature, and post-treatment (purification) that can be used in step 2 are the same as those exemplified in step 1, and the preferred configurations are also the same.

Triazine compound (1) can be used for organic electronic devices such as organic electroluminescent devices and photoelectric devices. Among these, triazine compound (1) is preferably used as a material for organic electroluminescent devices.

<Materials for organic electroluminescence devices>
The material for organic electroluminescent devices according to one embodiment of the present disclosure contains the above-mentioned triazine compound (1).
The triazine compound (1) can be used, for example, as an electron transport material for an organic electroluminescent device. The material for an organic electroluminescent device containing the triazine compound (1) contributes to the production of an organic electroluminescent device that can achieve high levels of luminous efficiency and life.

<Organic electroluminescent device>
The material for organic electroluminescent devices according to one embodiment of the present disclosure contains the above-mentioned triazine compound (1).

<Organic electroluminescent device>
An organic electroluminescent device containing the triazine compound (1) (hereinafter, may be simply referred to as an organic electroluminescent device) will be described below.
The organic electroluminescent device according to one embodiment of the present disclosure contains a triazine compound (1).
The configuration of the organic electroluminescent device is not particularly limited, but examples thereof include the following configurations (i) to (v).
(i): anode/light-emitting layer/cathode (ii): anode/hole-transport layer/light-emitting layer/cathode (iii): anode/light-emitting layer/electron-transport layer/cathode (iv): anode/hole-transport layer/light-emitting layer/electron-transport layer/cathode (v): anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-transport layer/electron-injection layer/cathode

The triazine compound (1) may be contained in any of the above layers, but in terms of excellent light-emitting properties of the organic electroluminescent device, it is preferable that the triazine compound (1) is contained in one or more layers selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode. Therefore, in the case of the configurations shown in (i) to (v) above, it is preferable that the triazine compound (1) is contained in one or more layers selected from the group consisting of the light-emitting layer, the electron transport layer, and the electron injection layer.

Hereinafter, an organic electroluminescent device according to one embodiment of the present disclosure will be described in more detail with reference to FIG. 1, taking the above configuration (v) as an example.
1 has a so-called bottom emission type element configuration, the organic electroluminescence device according to one embodiment of the present disclosure is not limited to a bottom emission type element configuration. That is, the organic electroluminescence device according to one embodiment of the present disclosure may have another known element configuration, such as a top emission type.

Figure 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device containing a triazine compound according to one embodiment of the present disclosure.

The organic electroluminescent device 100 comprises a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 in this order. However, some of these layers may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the light-emitting layer 5 and the electron transport layer 6, or the hole injection layer 3 may be omitted and the hole transport layer 4 may be provided directly on the anode 2. In addition, a single layer having the functions of multiple layers, such as an electron injection/transport layer having the functions of both the electron injection layer and the electron transport layer in a single layer, may be provided instead of the multiple layers. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be made up of multiple layers.

<<Layer Containing Triazine Compound (1)>>
1, the organic electroluminescent device 100 contains a triazine compound (1) in one or more layers selected from the group consisting of a light-emitting layer 5, an electron transport layer 6, and an electron injection layer 7. In particular, it is preferable that the electron transport layer 6 contains the triazine compound (1). The triazine compound (1) may be contained in a plurality of layers of the organic electroluminescent device.
In the following, an organic electroluminescent device 100 in which the electron transport layer 6 contains the triazine compound (1) will be described.

[Substrate 1]
The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate.
Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, a plastic film, etc. Among these, a glass plate, a quartz plate, and a light-transmitting plastic film are preferable.
Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.
In the case of a configuration in which light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[Anode 2]
An anode 2 is provided on the substrate 1 (on the side of the hole injection layer 3).
Examples of the anode material include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (e.g., 4 eV or more). Specific examples of the anode material include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ , and ZnO.
In the case of an organic electroluminescent device in which light is extracted through the anode, the anode is formed of a conductive transparent material that is transparent or substantially transparent to the emitted light.

[Hole injection layer 3, hole transport layer 4]
Between the anode 2 and a light-emitting layer 5 described below, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side.

The hole injection layer and hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer, and by interposing this hole injection layer and hole transport layer between the anode and the light-emitting layer, more holes are injected into the light-emitting layer with a lower electric field.

The hole injection layer and the hole transport layer also function as electron barrier layers. That is, the electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light emitting layer are prevented from leaking to the hole injection layer and/or the hole transport layer due to the electron barrier present at the interface between the light emitting layer and the hole injection layer and/or the hole transport layer. As a result, the electrons are accumulated at the interface within the light emitting layer, which brings about effects such as improved light emitting efficiency, and an organic electroluminescent element with excellent light emitting performance is obtained.

The material for the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property. The material for the hole injection layer and the hole transport layer may be either organic or inorganic.

Specific examples of materials for the hole injection layer and hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred in terms of the good performance of the organic electroluminescent device, and aromatic tertiary amine compounds are particularly preferred.

Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Examples include di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA), etc.

Inorganic compounds such as p-type Si and p-type SiC can also be used as examples of materials for the hole injection layer and hole transport layer.

The hole injection layer and the hole transport layer may be a single structure made of one or more materials, or may be a laminate structure made of multiple layers of the same or different compositions.

[Light-emitting layer 5]
The light-emitting layer 5 is provided between the hole transport layer 4 and the electron transport layer 6 described below.
Examples of materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

The light-emitting layer may consist of a single small molecule material or a single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from the dopant and can be of any color.

Examples of host materials include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, examples of the compound include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like.

Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, and the like. The fluorescent dopant may be a combination of two or more selected from these.

Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

Specific examples of fluorescent and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

The light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole transport layer 4 or electron transport layer 6). This can further increase the current efficiency of the organic electroluminescent device.

The light-emitting layer may be a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions.

[Electron transport layer 6]
An electron transport layer 6 is provided between the light emitting layer 5 and an electron injection layer 7 described below.
The electron transport layer has a function of transporting electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

As described above, the electron transport layer preferably contains the triazine compound (1). The electron transport layer may further contain, in addition to the triazine compound (1), one or more types selected from conventionally known electron transport materials.
In addition, when the triazine compound (1) is not contained in the electron transport layer but is contained in another layer, one or more types selected from conventionally known electron transport materials can be used as the electron transport material constituting the electron transport layer.

Conventionally known electron transport materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include 8-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, and tris(8-hydroxyquinolinato) gallium. bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato)-1-naphtholato aluminum, bis(2-methyl-8-quinolinato)-2-naphtholato gallium, etc.

The electron transport layer may be a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions.

In the organic electroluminescent device according to this embodiment, an electron injection layer may be provided for the purpose of improving the electron injection properties and improving the device characteristics (e.g., luminous efficiency, constant voltage driving, or high durability).

[Electron injection layer 7]
An electron injection layer 7 is provided between the electron transport layer 6 and a cathode 8 which will be described later.
The electron injection layer has a function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane, anthrone, etc. Examples of materials for the electron injection layer include inorganic compounds such as various oxides, nitrides, and oxynitrides, such as _SiO2 , AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C.

[Cathode 8]
A cathode 8 is provided on the electron injection layer 7 .
In the case of an organic electroluminescence element having a configuration in which only light emitted through the anode is extracted, the cathode can be formed from any conductive material.
Examples of materials for the cathode include metals with a small work function (hereinafter also referred to as electron injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, the metals with a small work function are, for example, metals with a work function of 4 eV or less.
Specific examples of cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium/copper mixtures, magnesium/silver mixtures, magnesium/aluminum mixtures, magnesium/indium mixtures, aluminum/aluminum oxide (Al ₂ O ₃ ) mixtures, indium, lithium/aluminum mixtures, rare earth metals, and the like.
Among these, from the viewpoints of electron injectability and durability against oxidation, etc., preferred are mixtures of an electron injecting metal and a second metal which has a larger and more stable work function than the electron injecting metal, such as a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide ( _Al2O3 ) mixture, and _a lithium/aluminum mixture.

[Method of forming each layer]
Each layer except for the electrodes (anode, cathode) described above can be formed by forming a thin film by a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. The material for each layer may be used alone or, if necessary, together with a material such as a binder resin or a solvent.
There is no particular restriction on the thickness of each layer thus formed, and it can be appropriately selected depending on the circumstances, but it is usually in the range of 5 nm to 5 μm.

The anode and cathode can be formed by forming a thin film of the electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask of the desired shape during vapor deposition or sputtering, or a thin film may be formed by vapor deposition or sputtering, and then a pattern of the desired shape may be formed by photolithography.

The thickness of the anode and cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

The layer containing triazine compound (1) may be used in combination with the above-mentioned conventionally known electron transporting material. Thus, for example, triazine compound (1) and a conventionally known electron transporting material may be co-deposited, or a layer of a conventionally known electron transporting material may be laminated on a layer of triazine compound (1).

Organic electroluminescent elements may be used as a type of lamp for illumination or exposure light sources, as a projection device that projects images onto a screen, or as a display device that directly displays still or moving images. When using organic electroluminescent elements as a display device for playing moving images, the driving method may be a simple matrix (passive matrix) method or an active matrix method. In addition, a full-color display device can be produced by using two or more types of organic electroluminescent elements that emit different light colors.

When used as an electron transport layer, triazine compound (1) can provide an organic electroluminescent device that is significantly superior in luminous efficiency and long life characteristics compared to conventionally known triazine compounds. Furthermore, triazine compound (1) has high amorphousness and high film quality stability due to its steric hindrance skeleton. This provides effects such as improved driving stability and improved luminous efficiency of organic electroluminescent devices. Furthermore, triazine compound (1) has high chemical stability due to its characteristic skeleton, and can contribute to the long life of organic electroluminescent devices.

The triazine compound (1) can be used as an electron transport layer in an organic electroluminescent device to provide a triazine compound that can achieve low-voltage operation, high efficiency, and long life of the device to a high degree. Furthermore, it is possible to provide an organic electroluminescent device that can achieve low-voltage operation, high efficiency, and long life by using the triazine compound (1).

The present invention will be described in more detail below with reference to examples, but the present invention should not be construed as being limited in any way by these examples.

[ ¹ H-NMR measurement]
For ¹ H-NMR measurements, a Bruker ASCEND 400 (400 MHz; manufactured by BRUKER) was used. ¹ H-NMR was performed using deuterated chloroform (CDCl ₃ ) as the measurement solvent and tetramethylsilane (TMS) as the internal standard. The measurements were performed using

[Emission characteristic measurement]
The light emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the device prepared in each Example (described later) in a 25° C. environment using a luminance meter BM-9 (product name, manufactured by Topcon Technohouse Corporation).
The reagents used were commercially available.

Synthesis Example 1

Under an argon atmosphere, 2-{3-(2-biphenylyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-4,6-diphenyl-1,3,5-triazine (7.24 g), 3-bromo-9,9-dimethylxanthene (2.54 g), palladium acetate (59 mg), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (252 mg) were suspended in THF (90 mL). To this suspension was added 2.0 M potassium carbonate aqueous solution (13 mL), and the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified by recrystallization (toluene) to obtain the desired 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine (compound 1-2) (4.31 g, 73%).

¹ HNMR (CDCl ₃ ) δ1.66 (s, 6H), 7.06-7.13 (m, 3H), 7.20-7.24 (m, 2H), 7.27-7.37 (m, 6H), 7 .44-7.46 (m, 2H), 7.50 -7.65 (m, 9H), 7.69-7.72 (m, 1H), 8.73 (t, J=1.6Hz, 1H), 8.76-8.80 (m, 4H) , 8.81 (t, J=1.6Hz, 1H).

Synthesis Example 2

Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (4.00 g, 7.8 mmol), tris(dibenzylideneacetone)dipalladium (108 mg, 0.12 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (200 mg, 0.47 mmol), and 2M tripotassium phosphate (12 mL, 24 mmol) were suspended in THF (68 mL). Further, a mixture of 3-bromo-9,9-dimethyl-9H-xanthene and 9,9-dimethyl-9H-xanthene (5.30 g, 3-bromo-9,9-dimethyl-9H-xanthene:9,9-dimethyl-9H-xanthene=55:45) dissolved in THF (10 mL) was added dropwise. Thereafter, this reaction mixture was stirred at 80° C. for 16 hours. After cooling to room temperature, chloroform (150 mL) was added to the reaction mixture to extract the organic layer, which was then washed with water and then with saturated saline. Sodium sulfate and activated carbon were added to the extract and stirred at room temperature for a while, followed by filtration through Celite, and low boiling points were distilled off from the filtrate under reduced pressure. The resulting solid was recrystallized from toluene (115°C, 5 mL) to obtain the desired white solid of 2-[3-(9,9-dimethyl-9H-xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-14) (yield: 2.9 g, 62%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.05 (t, J = 1.6Hz, 1H), 8.79-8.82 (m, 5H), 7.89-7.92 (m, 2H), 7.67 -7.73 (m, 3H), 7.52-7.66 (m, 9H), 7 .45 (dd, J=7.7, 1.6Hz, 1H), 7.22 (dd, J=7.9, 1.7Hz, 1H), 7.12 (d, J=8.4Hz, 1H) ), 7.08-7.13 (m, 2H), 1.73 (s, 6H).

Synthesis Example 3

Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-terphenyl-3-yl]-1,3,5-triazine (3.90 g, 6.6 mmol), 3-bromo-9,9-dimethyl-9H-thioxanthene (2.43 g, 8.0 mmol), palladium acetate (75 mg, 0.33 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (316 mg, 0.66 mmol) were suspended in THF (66 mL). To this suspension was added 2M potassium phosphate aqueous solution (10 mL, 20 mmol), and the mixture was heated to reflux for 18 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 110°C for a while, after which it was filtered through Celite and low boiling points were distilled off from the filtrate under reduced pressure. The obtained solid was purified by recrystallization (toluene) to obtain the desired 2-[5-(9,9-dimethyl-9H-thioxanthen-3-yl)-1,1':2',1''-terphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-77) (yield: 2.81 g, 62%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.81 (t, J = 1.6Hz, 1H), 8.73-8.78 (m, 4H), 8.71 (t, J = 1.6Hz, 1H) , 7.64-7.70 (m, 1H), 7.44-7.70 (m, 14H), 7.18-7.34 (m, 8H), 1.71 (s, 6H).

Synthesis Example 4

Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (64.6 mg, 0.13 mmol), 3-bromo-9-methyl-9-phenyl-9H-xanthene (42.6 mg, 0.14 mmol), palladium acetate (1.6 mg, 6.9 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (6.6 mg, 14 μmol) were suspended in THF (1.4 mL). 2M potassium phosphate aqueous solution (0.2 mL, 0.44 mmol) was added to this suspension, and the mixture was heated to reflux for 18 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 110°C for a while, then filtered through Celite, and low boiling points were distilled off from the filtrate under reduced pressure. The obtained solid was purified by column chromatography (hexane/chloroform), and then washed with hexane to obtain the desired 2-[3-(9-methyl-9-phenyl-9H-xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-152) (yield: 58.6 mg, 71%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.96 (s, 1H), 8.76-8.82 (m, 5H), 7.81 (d, J = 7.7Hz, 1H), 7.73 (s, 1H), 7.56-7.69 (m, 8H), 7.48-7.54 (m, 2H), 7.43 (d, J=7.7Hz, 1H), 7.37 (d, J=7.4Hz, 2H), 7.28 (d, J=7.4Hz, 2H), 7.12-7.24 (m, 5H), 6.96 (td, J=7.4Hz, 1.1Hz, 1H), 6.89 (dd, J=7.8Hz, 1.5Hz, 1H), 2.02 (s, 3H).

Synthesis Example 5

Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-terphenyl-3-yl]-1,3,5-triazine (32 mg, 54 μmol), 2'-chloro-spiro[cyclohexane-1,9'-[9H]thioxanthene] (17 mg, 57 μmol), palladium acetate (0.4 mg, 1.6 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.5 mg, 3.2 μmol) were suspended in THF (0.54 mL). 2M potassium phosphate aqueous solution (0.32 mL, 0.16 mmol) was added to this suspension, and the mixture was heated to reflux for 22 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was filtered off. The resulting solid was purified by silica gel column chromatography (hexane:ethyl acetate=98:2) and preparative thin layer chromatography (hexane:ethyl acetate=9:1) to obtain the desired 2-[5-spiro[cyclohexane-1,9'-[9H]thioxanthene]-3-yl)-1,1':2',1''-terphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-160) (yield: 4.2 mg, 10%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.86 (dd, J = 1.7, 1.6Hz, 1H), 8.75-8.77 (m, 4H), 8.70 (dd, J = 1.6, 1.6Hz, 1H), 7.67-7.69(m , 1H), 7.47-7.66 (m, 14H), 7.15-7.32 (m, 8H), 2.29-2.41 (m, 4H), 1.72 (brs, 4H) ), 0.83-0.90 (m, 2H).

Synthesis Example 6

Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (100 mg, 0.20 mmol), 3-chloro-7H-benzo[c]xanthene (57.3 mg, 0.22 mmol), palladium acetate (2.2 mg, 9.8 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (9.3 mg, 20 μmol) were suspended in THF (2.0 mL). 2M potassium phosphate aqueous solution (0.3 mL, 0.59 mmol) was added to this suspension, and the mixture was heated to reflux for 16 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dissolved in chloroform and filtered through a silica gel pad (hexane:chloroform = 1:1), and low boiling points were removed from the filtrate by vacuum distillation to obtain the desired 2-[3-(7H-benzo[c]xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-158) (yield: 43.0 mg, 35%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.05 (dd, J = 1.7Hz, 2.0Hz, 1H), 8.76-8.82 (m, 5H), 8.42 (d, J = 8.2Hz, 1H), 7.94 (dd, J=1.7Hz, 2.0Hz, 1H), 7.90 (m, 1H), 7.82 (d, J = 8.1Hz, 1H) 7.46-7.75 (m, 15H), 7.34 (d, J = 8.3Hz, 1H) , 7.28 (d, J=8.3Hz, 1H), 4.31 (s, 2H).

Reference Example 1

Under a nitrogen atmosphere, 2-[3-chloro-5-(phenanthren-9-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (1.00 g, 1.9 mmol), phenylboronic acid (282 mg, 2.3 mmol), palladium acetate (13.0 mg, 0.06 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 55.0 mg, 0.12 mmol), 1,4-dioxane (50 mL) and 2M aqueous tripotassium phosphate solution (2.9 mL, 5.8 mmol) were added to a 300 mL four-neck flask and stirred at 95°C for 6 hours. After allowing the resulting reaction solution to cool to room temperature, water (100 mL) was added to the reaction mixture, and the precipitate was collected by filtration and washed with water, methanol and then hexane to obtain a gray powder. The resulting gray powder was purified by recrystallization with toluene to obtain the target product, 4,6-diphenyl-2-[5-(phenanthren-9-yl)-biphenyl-3-yl]-1,3,5-triazine (compound ETL-1), as a gray powder (yield 700 mg, 65%).

¹ H-NMR (CDCl ₃ ): δ9.12 (t, J=1.7Hz, 1H) 8.93 (t, J=1.7Hz, 1H), 8.85 (d, J=8.3Hz, 1H) , 8.77-8.80 (m, 5H), 8.01-8.04 (m, 2H), 7.98 (dd, J=7.8Hz, 1.4Hz, 1H) , 7.88 (s, 1H), 7.84 (dd, J = 8.1Hz, 1.0Hz, 2H), 7.73 (t, J = 7.8Hz, 1.3Hz , 2H), 7.67 (t, J=7.2Hz, 1H), 7.52-7.63 (m, 9H), 7.45 (t, J=7.3Hz, 1H).

Next, the obtained compound was used to carry out element evaluation.
Element Example 1 (see FIG. 2)

(Preparation of Substrate 1 and Anode 2)
A glass substrate with an indium tin oxide (ITO) transparent electrode, on which a 2 mm wide ITO film (thickness: 110 nm) was patterned in a stripe shape, was prepared as the substrate 1 having an anode 2 on its surface. Next, this substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning.

(Preparation for vacuum deposition)
After cleaning and surface treatment, each layer was deposited by vacuum deposition on the substrate by vacuum deposition, forming a laminate of each layer.
First, the glass substrate was placed in a vacuum deposition chamber, and the pressure was reduced to 1.0×10 ⁻⁴ Pa. Then, each layer was produced according to the film-forming conditions in the following order. Each organic material was formed by a resistance heating method.

(Fabrication of Hole Injection Layer 3)
Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a ratio of 99:1 (mass ratio) to form a 10 nm film to prepare hole injection layer 3. The film formation rate was 0.1 nm/sec.

(Preparation of First Hole Transport Layer 41)
Sublimation-purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film of 85 nm at a rate of 0.2 nm/sec to prepare a first hole transport layer 41 .

(Preparation of second hole transport layer 42)
Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1′-biphenyl-4-yl)amine was formed into a film having a thickness of 5 nm at a rate of 0.15 nm/sec to prepare a second hole transport layer 42 .

(Preparation of Light-Emitting Layer 5)
Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9′-spirofluorene were mixed in a ratio of 95:5 (mass ratio) to form a film of 20 nm, thereby producing the light-emitting layer 5. The film formation rate was 0.1 nm/sec.

(Preparation of Hole Blocking Layer 9)
The 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine synthesized in Synthesis Example 1 was deposited to a thickness of 6 nm at a rate of 0.05 nm/sec to form a hole blocking layer 9 .

(Preparation of Electron Transport Layer 6)
Sublimation-purified 4'-{4-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl]-1,1'-biphenylcarbonitrile and 8-hydroxyquinolinolatolithium (hereinafter, Liq) were mixed in a mass ratio of 50:50 to form a 25 nm film, thereby producing an electron transport layer 6. The film formation rate was 0.15 nm/sec.

(Fabrication of Electron Injection Layer 7)
Liq was deposited at a rate of 0.02 nm/sec to a thickness of 1 nm to form an electron injection layer 7 .

(Preparation of Cathode 8)
Finally, a metal mask was placed so as to be perpendicular to the ITO stripes (anode 2) on the substrate 1, and a cathode 8 was formed. The cathode had a two-layer structure in which silver/magnesium (mass ratio 1/10) and silver were formed in this order to thicknesses of 80 nm and 20 nm, respectively. The film formation rate of silver/magnesium was 0.5 nm/sec, and the film formation rate of silver was 0.2 nm/sec.

In this manner, an organic electroluminescent device 100 having a light-emitting area ^{of 4} mm2 was produced as shown in Fig. 2. The thickness of each film was measured using a stylus film thickness meter (DEKTAK, manufactured by Bruker).
The element was then sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less by sealing a glass sealing cap and the film-formed substrate (element) with bisphenol F type epoxy resin (manufactured by Nagase Chemtex Corporation).

Element Reference Example 1
An organic electroluminescent device was produced in the same manner as in Element Example 1, except that in the hole blocking layer 9, instead of forming a film of 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine at a rate of 0.05 nm/sec to a thickness of 6 nm, ETL-1 was formed at a rate of 0.05 nm/sec.

A direct current was applied to the fabricated organic electroluminescent device, and the light-emitting characteristics were evaluated according to the method described in the light-emitting characteristic measurement above.

As the light emitting characteristics, the voltage (V) and current efficiency (cd/A) when a current density of 10 mA/ ^cm2 was applied were measured, and the element life during continuous lighting was measured. The element life was measured by measuring the luminance decay time during continuous lighting when driven at an initial luminance of 1000 cd/ ^m2 , and measuring the time required for the luminance (cd/ ^m2 ) to decrease by 2%. The values of voltage (V), current efficiency (cd/A) and life were expressed as relative values when the element reference example-1 was taken as 100. The results are shown in Table 1.

From Table 1, it was found that the organic electroluminescent device using triazine compound (1) has a significantly longer device life than the reference example.

1. Substrate 2. Anode 3. Hole injection layer 4. Hole transport layer 5. Light emitting layer 6. Electron transport layer 7. Electron injection layer 8. Cathode 9. Hole blocking layer 41. First hole transport layer 42. Second hole transport layer 100. Organic electroluminescent device

Claims (17)

Triazine compound represented by formula (1):
In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
At least one of the two ^R2's represents an alkyl group having 1 to 6 carbon atoms , or
Two ^R2 's, together with the carbon atom to which they are attached, form a cyclopentane or cyclohexane ring;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
When p is 2, two L's may be different from each other. The triazine compound according to claim 1, which is a compound represented by formula (1a):
In the formula, Ar ¹ , Ar ² , R ¹ , R ² , R ³ , Z, L and p are as defined in formula (1) above. 3. The triazine compound according to claim 1, wherein Ar ¹ and Ar ² each independently represent a phenyl group or a biphenylyl group. The triazine compound according to any one of claims 1 to 3, wherein Ar ¹ and Ar ² are the same group. ^R1 is
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
5. The triazine compound according to claim 1, which is a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. The triazine compound according to any one of claims 1 to 5, wherein R ¹ is a phenyl group, a biphenyl group, a naphthyl group, or a phenanthrenyl group. R ³ is the same or different,
A hydrogen atom, or
The triazine compound according to any one of claims 1 to 6, wherein the alkyl group has 1 to 6 carbon atoms. The triazine compound according to any one of claims 1 to 7, wherein Z is an oxygen atom. The triazine compound according to any one of claims 1 to 8, wherein L is a metaphenylene group or a paraphenylene group, which may be substituted with a phenyl group, a naphthyl group, or an alkyl group having 1 to 4 carbon atoms. The triazine compound according to any one of claims 1 to 9, wherein p is 0 or 1. A method for producing a triazine compound represented by formula (1), comprising subjecting a compound represented by formula (2) and a compound represented by formula (3) to a coupling reaction:
In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
At least one of the two ^R2's represents an alkyl group having 1 to 6 carbon atoms , or
Two ^R2 's, together with the carbon atom to which they are attached, form a cyclopentane or cyclohexane ring;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
^M1 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^Y1 and ^Y2 each independently represent a chlorine atom, a bromine atom, or an iodine atom;
Each ^Y3 independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group;
Each ^Y4 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group;
The two (OY ⁴ ) groups may be joined together to form a ring with the boron atom;
^X1 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group or an iodine atom. A method for producing a triazine compound represented by formula (1), comprising subjecting a compound represented by formula (4) and a compound represented by formula (5) to a coupling reaction:
In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group, or a naphthyl group;
Ar ¹ and Ar ² each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
^R1 is
Hydrogen atoms,
an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or
represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms;
R ² may be the same or different;
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
At least one of the two ^R2's represents an alkyl group having 1 to 6 carbon atoms , or
Two ^R2 's, together with the carbon atom to which they are attached, form a cyclopentane or cyclohexane ring;
R ³ is the same or different,
Hydrogen atoms,
an alkyl group having 1 to 6 carbon atoms, or
represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms;
Two adjacent ^R3 's may be joined together to form a 5- or 6-membered ring including the carbon atoms to which they are bonded;
Z represents an oxygen atom or a sulfur atom;
L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms;
p represents 0, 1 or 2;
^X2 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom;
^M2 represents ^ZnY1 , ^MgY2 , Sn( ^Y3 ) ₃ , or B( ^OY4 ) ₂ ;
^Y1 and ^Y2 each independently represent a chlorine atom, a bromine atom, or an iodine atom;
Each ^Y3 independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group;
Each ^Y4 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group;
The two (OY ⁴ ) groups may be joined together to form a ring with the boron atom. The method for producing a triazine compound according to claim 11 or 12, wherein M ¹ or M ² is B(OY ⁴ ) ₂ . The process according to any one of claims 11 to 13, wherein the coupling reaction is carried out in the presence of a palladium catalyst, and the palladium catalyst is a palladium catalyst having a tertiary phosphine as a ligand. The process according to any one of claims 11 to 14, wherein the coupling reaction is carried out in the presence of a palladium catalyst, and the palladium catalyst has triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl as a ligand. A material for an organic electroluminescent device, comprising the triazine compound according to any one of claims 1 to 10. An organic electroluminescent device comprising the triazine material according to any one of claims 1 to 10.

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