JP2020094034A - Triazine compound, material for organic electroluminescent element, and organic electroluminescent element - Google Patents

Abstract

To provide a triazine compound that contributes to the formation of an organic electroluminescent element that exhibits high luminous efficiency and long service life properties, and has a high glass transition temperature, and a material for organic electroluminescent element and an organic electroluminescent element containing the triazine compound.SOLUTION: A triazine compound has a specific structure represented by the following formula.SELECTED DRAWING: Figure 2

Description

The present disclosure relates to a triazine compound, a material for an organic electroluminescence device, and an organic electroluminescence device.

The organic electroluminescence device has been put into practical use mainly for small mobile applications. However, performance improvement is essential for further expansion of applications, and materials having high luminous efficiency characteristics and long life characteristics are required. In addition, when the organic electroluminescent element is used in high temperature regions or in vehicle applications, it is necessary to assume that it will be used under high temperatures. Therefore, a material having a high glass transition temperature is required as a material for the organic electroluminescent element. Be done.

Patent Document 1 discloses a triazine compound which is a material for an organic electroluminescence device capable of highly efficiently reducing a driving voltage.
Patent Document 2 discloses a triazine compound which is a material for an organic electroluminescence device having high heat resistance and capable of reducing a driving voltage.

JP, 2017-178931, A JP, 2011-63584, A

However, the market demands for expanding applications and expanding usable environments are very strong, and the triazine compounds according to Patent Documents 1 and 2 are related to three properties of high glass transition temperature, high luminous efficiency and long life characteristics. It cannot be said that these are sufficiently satisfied, and there is a demand for a material that achieves the above three characteristics in a higher level.

Therefore, one aspect of the present disclosure is directed to providing a triazine compound having a high glass transition temperature, which contributes to the formation of an organic electroluminescent device that exhibits high emission efficiency and long life characteristics.
Further, another aspect of the present disclosure is directed to providing a material for an organic electroluminescence device containing the above triazine compound.
Still another aspect of the present disclosure is directed to providing an organic electroluminescent device that exhibits high luminous efficiency and long life characteristics and can be used in various applications or under various environments.

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

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group or a naphthyl group;
Ar ³ is a tricyclic or tetracyclic fused ring,
Aromatic hydrocarbon group,
A nitrogen-containing aromatic group consisting of only a 6-membered ring, or
Represents a heteroaromatic group in which the heteroatom is a Group 16 element;
Ar ⁴ represents a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group, or a diazanaphthyl group;
Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently one or more selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group. Optionally substituted with groups;
X represents a phenylene group, a naphthylene group, an azaphenylene group, a diazaphenylene group, an azanaphthylene group or a diazanaphthylene group;
p represents 0, 1 or 2;
When p is 2, the two Xs may be the same or different.

A material for an organic electroluminescence device according to another aspect of the present disclosure contains the above triazine compound.

An organic electroluminescent device according to still another aspect of the present disclosure contains the above triazine compound.

According to one aspect of the present disclosure, it is possible to provide a triazine compound having a high glass transition temperature, which contributes to the formation of an organic electroluminescent device that exhibits high emission efficiency and long life characteristics. Further, according to another aspect of the present disclosure, it is possible to provide a material for an organic electroluminescence device containing the triazine compound. Furthermore, according to still another aspect of the present disclosure, it is possible to provide an organic electroluminescent device that exhibits high emission efficiency and long life characteristics and can be used for various applications.

It is a schematic sectional drawing which shows an example of the laminated constitution of the organic electroluminescent element concerning one aspect of this indication. It is a schematic sectional drawing which shows the example (structure of element example-1) of another laminated constitution of the organic electroluminescent element concerning one aspect of this indication.

Hereinafter, the triazine compound according to one embodiment of the present disclosure will be described in detail.

<Triazine compound>
A triazine compound according to one embodiment of the present disclosure is a triazine compound represented by the formula (1):

In the formula,
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group or a naphthyl group;
Ar ³ is a tricyclic or tetracyclic fused ring,
Aromatic hydrocarbon group,
A nitrogen-containing aromatic group consisting of only a 6-membered ring, or
Represents a heteroaromatic group in which the heteroatom is a Group 16 element;
Ar ⁴ represents a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group, or a diazanaphthyl group;

Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently one or more selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group. Optionally substituted with groups;
X represents a phenylene group, a naphthylene group, an azaphenylene group, a diazaphenylene group, an azanaphthylene group or a diazanaphthylene group;
p represents 0, 1 or 2;
When p is 2, the two Xs may be the same or different.

Hereinafter, the triazine compound represented by the formula (1) may be referred to as a triazine compound (1). The definition of the substituent in the triazine compound (1) and its preferred specific examples are as follows.

[Regarding Ar ¹ and Ar ² ]
Ar ¹ and Ar ² each independently represent a phenyl group, a biphenylyl group or a naphthyl group. Ar ¹ and Ar ² are each independently substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group. Good.

Ar ¹ and Ar ² are preferably the same group. When Ar ¹ and Ar ² are the same group, the triazine compound (1) can be easily synthesized.
From the standpoint that the triazine compound (1) has excellent electron transporting material properties, Ar ¹ and Ar ² are preferably each independently an unsubstituted phenyl group, biphenylyl group or naphthyl group.

As Ar ¹ and Ar ² , each independently, for example, a phenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, a p-fluorophenyl group, a m-fluorophenyl group, an o-fluorophenyl group, 3,5-difluorophenyl group, 2,4,6-trifluorophenyl group, pentafluorophenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group, 1-naphthyl group, 2- Naphthyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl -4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl- 2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 2-(2-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 4 -(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3 -(4-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 2-(3-methylpyridin-2-yl)phenyl group, 3-(3-methylpyridin-2-yl)phenyl group, 4 -(3-Methylpyridin-2-yl)phenyl group, 2-(4-methylpyridin-2-yl)phenyl group, 3-(4-methylpyridin-2-yl)phenyl group, 4-(4-methyl Pyridin-2-yl)phenyl group, 2-(5-methylpyridin-2-yl)phenyl group, 3-(5-methylpyridin-2-yl)phenyl group, 4-(5-methylpyridin-2-yl) ) Phenyl group, 2-(6-methylpyridin-2-yl)phenyl group, 3-(6-methylpyridin-2-yl)phenyl group, 4-(6-methylpyridin-2-yl)phenyl group, 2 -(2-Methylpyridin-3-yl)phenyl group, 3-(2-methylpyridin-3-yl)phenyl group, 4-(2-methylpyridin-3-yl)phenyl group, 2-(4-methyl) Pyridin-3-yl) Phenyl group, 3-(4-methylpyridin-3-yl)phenyl group, 4-(4-methylpyridin-3-yl)phenyl group, 2-(5-methylpyridin-3-yl)phenyl group, 3- (5-Methylpyridin-3-yl)phenyl group, 4-(5-methylpyridin-3-yl)phenyl group, 2-(6-methylpyridin-3-yl)phenyl group, 3-(6-methylpyridine) -3-yl)phenyl group, 4-(6-methylpyridin-3-yl)phenyl group, 2-(2-methylpyridin-4-yl)phenyl group, 3-(2-methylpyridin-4-yl) Phenyl group, 4-(2-methylpyridin-4-yl)phenyl group, 2-(3-methylpyridin-4-yl)phenyl group, 3-(3-methylpyridin-4-yl)phenyl group, 4- (3-methylpyridin-4-yl)phenyl group and the like can be mentioned.

[About Ar ³ ]
In Formula (1), Ar ³ is a tricyclic or tetracyclic fused ring,
Aromatic hydrocarbon group,
A nitrogen-containing aromatic group consisting of only a 6-membered ring, or
It represents a heteroaromatic group in which the hetero atom is a Group 16 element.
Ar ³ may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group.

Examples of the aromatic hydrocarbon group which is a tricyclic or tetracyclic condensed ring include a phenanthryl group, anthryl group, pyrenyl group, fluorenyl group, benzofluorenyl group, triphenylenyl group and fluoranthenyl group. Be done. These groups may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group and a diazanaphthyl group.

Ar ³ is a fluorine atom, a methyl group, a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group and a diazanaphthyl group in that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device. It is preferably a tricyclic or tetracyclic fused aromatic hydrocarbon group which may be substituted with one or more groups selected from the group consisting of groups.
Further, Ar ³ is preferably an unsubstituted condensed aromatic hydrocarbon group in terms of easy synthesis of the triazine compound (1).

Examples of the nitrogen-containing aromatic group consisting of only a 6-membered ring which is a condensed ring of 3 or 4 rings include, for example, benzo[b]quinolyl group, benzo[c]quinolyl group, benzo[f]quinolyl group, benzo Examples include [g]quinolyl group, benzo[h]quinolyl group, phenazinyl group, azapyrenyl group, diazapyrenyl group, azatriphenylenyl group and diazatriphenylenyl group. These groups may be substituted with one or more groups selected from the group consisting of fluorine atom, methyl group, phenyl group, naphthyl group, azaphenyl group, diazaphenyl group, azanaphthyl group and diazanaphthyl group.

Ar ³ is an unsubstituted benzo[b]quinolyl group, benzo[c]quinolyl group, or benzo[f]quinolyl in that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device. A group, a benzo[g]quinolyl group, a benzo[h]quinolyl group, an azapyrenyl group, a diazapyrenyl group, an azatriphenylenyl group, and a diazatriphenylenyl group are preferable.

Examples of the heteroaromatic group which is a tricyclic or tetracyclic fused ring hetero atom and is a group 16 element include, for example, dibenzothiophenyl group, dibenzofuranyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group. Etc. These groups may be substituted with one or more groups selected from the group consisting of fluorine atom, methyl group, phenyl group, naphthyl group, azaphenyl group, diazaphenyl group, azanaphthyl group and diazanaphthyl group.

Ar ³ is preferably an unsubstituted dibenzofuranyl group or a dibenzothiophenyl group in that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device.

[About Ar ⁴ ]
Ar ⁴ represents a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group or a diazanaphthyl group. These groups may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group, and a diazanaphthyl group.

Examples of Ar ⁴ include a phenyl group, a naphthyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, a quinoxalinyl group and a quinazolinyl group. These groups may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group and a diazanaphthyl group.

Ar ⁴ is a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a naphthyl group, a pyridyl group, and a methyl group in that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device. Pyridyl group, dimethylpyridyl group, phenylpyridyl group, diphenylpyridyl group, pyrimidyl group, methylpyrimidyl group, dimethylpyrimidyl group, phenylpyrimidyl group, diphenylpyrimidyl group, pyrazyl group, methylpyrazyl group or phenylpyrazyl group Preferably.

[About X]
X represents a phenylene group, an azaphenylene group, a diazaphenylene group, a naphthylene group, an azanaphthylene group or a diazanaphthylene group.

Examples of X include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 2,3-pyridylene group, 2,4-pyridylene group, 2,5-pyridylene group, and 2, 6-pyridylene group, 2,4-pyrimidylene group, 2,5-pyrimidylene group, 2,5-pyrazylene group, 1,2-naphthylene group, 1,3-naphthylene group, 1,4-naphthylene group, 1,5 -Naphthylene group, 1,6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group, 2,4-naphthylene group, 2,5-naphthylene group, 2,6- Naphthylene group, 2,7-naphthylene group, 2,8-naphthylene group, 2,3-quinolylene group, 2,4-quinolylene group, 2,5-quinolylene group, 2,6-quinolylene group, 2,7-quinolylene group Group, 2,8-quinolylene group, 3,4-quinolylene group, 3,5-quinolylene group, 3,6-quinolylene group, 3,7-quinolylene group, 3,8-quinolylene group, 4,5-quinolylene group , 4,6-quinolylene group, 4,7-quinolylene group, 4,8-quinolylene group, 5,8-quinolylene group, 2,3-quinoxarylene group, 2,5-quinoxarylene group, 2,6-quinoxarylene group, 2,4-quinazolylene group, 2,5-quinazolylene group, 2,6-quinazolylene group and the like can be mentioned.

It is preferable that X is a phenylene group or an azaphenylene group, since the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device, and a 1,2-phenylene group, 1,3- It is more preferably a phenylene group, a 1,4-phenylene group, a 2,3-pyridylene group, a 2,4-pyridylene group, a 2,5-pyridylene group, or a 2,6-pyridylene group.

[About p]
p represents 0, 1, or 2. When p is 2, the two Xs may be the same or different.
From the viewpoint that the triazine compound (1) contributes to the formation of a higher performance organic electroluminescent device, p is more preferably 0 or 1.

[Specific Examples of Triazine Compound (1)]
Specific examples of the triazine compound (1) include the following (A-1) to (A-285), but the present disclosure is not limited thereto. As the triazine compound (1), (A-3), (A-39), (A-49), (A-53), (A- 54), (A-58), (A-62), (A-98), (A-106), (A-122), (A-129), (A-130), (A-182). , (A-254) and (A-269) are preferable.

Next, a method for producing the triazine compound (1) will be described.
The triazine compound (1) can be produced by the methods shown in the following synthetic routes (i) to (vi).

In formulas (2) to (12),
^{Ar 1, Ar 2, Ar 3} , Ar 4, X, and p definitions are respectively the same as ^{Ar 1, Ar 2, Ar 3} , Ar 4, X, and p as defined in the formula (1);
Y ¹ , Y ² , Y ³ and Y ⁴ each independently represent a halogen atom;
R ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group;
The two R ^{1 s} of B(OR ¹ ) ₂ may be the same or different;
Two R ¹ , an oxygen atom, and a boron atom may form a ring.

Examples of the halogen atom represented by Y ¹ , Y ² , Y ³ and Y ⁴ include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and in terms of a good yield of the triazine compound (1). , Chlorine atom or bromine atom is preferred.

Examples of B(OR ¹ ) ₂ include B(OH) ₂ , B(OMe) ₂ , B(O ⁱ Pr) ₂ , B(OBu) ₂ , B(OPh) _{2, and the} like. In addition, 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(OR ¹ ) ₂ when two R ¹ , an oxygen atom, and a boron atom form a ring include, for example, groups represented by the following (I) to (VI): The group represented by (II) is preferable because it can be exemplified and the yield is good.

The coupling reaction in the synthetic routes (i) to (vi) is performed by using the halogenated aryl compound represented by the formula (2), (3), (4), (11) or (12) and the formula (5), A method for reacting a boron compound represented by (6), (7), (8), (9) or (10) in the presence of a palladium catalyst and a base, which is a general Suzuki-Miyaura reaction condition. Can be applied.

The boron compound can be produced, for example, according to the method disclosed in The Journal of Organic Chemistry, Volume 60, page 7508, 1995 or The Journal of Organic Chemistry, Volume 65, page 164, 2000.
The aryl halide can be produced, for example, according to Journal of the American Chemical Society, Vol. 74, p. 6289, 1952 or Synlett, p. 808, 2002. Moreover, you may use a commercial item. From the viewpoint of good reaction yield, the aryl halide is preferably used in an amount of 0.5 to 3.0 molar equivalents with respect to the boron compound.

In the boronation reaction in the synthetic routes (iii) to (vi), the halogenated aryl compound represented by the formula (2), (3) or (4) is added to a boron raw material (for example, pinacolate) in the presence of a palladium catalyst and a base. Borane, bispinacolatodiboron, etc.) to produce a boron compound represented by the formula (5), (6), (7) or (8). These boron compounds can be produced, for example, according to the method disclosed in The Journal of Organic Chemistry, Volume 60, page 7508, 1995 or Tetrahedron Letters, Volume 38, page 3447, 1997.

Examples of the palladium catalyst used in the above-mentioned coupling reaction and boration reaction include palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. Further, complex compounds such as π-allyl palladium chloride dimer, palladium acetylacetonato, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium; and Dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine) And a palladium complex having a tertiary phosphine such as dichlorobis(tricyclohexylphosphine)palladium as a ligand. These can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound.

Examples of the tertiary phosphine 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 (Diphenylphosphino)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, 2-dicyclohexyl phosphino-2',4',6'-triisopropyl biphenyl, etc. are mentioned.

Among them, a palladium complex having a tertiary phosphine as a ligand is preferable in terms of good yield, and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl or tricyclohexylphosphine as a ligand is preferable. The palladium complex having is more preferable.

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, more preferably 1:2 to 3:1 in terms of good yield. preferable. The amount of the palladium catalyst used in the above coupling reaction and boration reaction is not limited, but in terms of good yield, the molar equivalent of the palladium catalyst is in the range of 0.005 to 0.5 molar equivalent to the boron compound. Is preferred.

Examples of the base used in the above-mentioned coupling reaction and boration reaction include metal hydroxide salts such as sodium hydroxide, potassium hydroxide and calcium hydroxide, metals such as sodium carbonate, potassium carbonate, lithium carbonate and cesium carbonate. Carbonate, metal acetate such as potassium acetate and sodium acetate, metal phosphate such as potassium phosphate and sodium phosphate, metal fluoride salt such as sodium fluoride, potassium fluoride and cesium fluoride, sodium methoxide, Examples thereof include metal alkoxides such as potassium methoxide, sodium ethoxide, potassium isopropyl oxide and potassium tert-butoxide. Of these, metal carbonates or metal phosphates are preferable, and potassium carbonate or potassium phosphate is more preferable, from the viewpoint of good reaction yield. There is no particular limitation on the amount of base used. From the viewpoint 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.

The above-mentioned coupling reaction and boration reaction can be carried out in a solvent.
Examples of the solvent include water, diisopropyl ether, dibutyl ether, cyclopentylmethyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, dimethoxyethane and the like; benzene, toluene, xylene, mesitylene, tetralin. Such as aromatic hydrocarbons; carbonic acid esters such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, Esters such as γ-lactone; N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), N-methylpyrrolidone (NMP) and other amides; N,N,N′,N′-tetramethylurea (TMU) Urea such as N,N′-dimethylpropyleneurea (DMPU); dimethyl sulfoxide (DMSO), methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, 2, Alcohol such as 2,2-trifluoroethanol; and the like. These may be used alone or may be mixed in any ratio and used. The amount of solvent used is not particularly limited. Among these, water, ether, amide, alcohol, and a mixed solvent thereof are preferable in terms of good reaction yield, and a mixed solvent of THF and water or a mixed solvent of toluene and 1-butanol is more preferable.

The above-mentioned coupling reaction and boration reaction can be carried out at a temperature appropriately selected from 0°C to 200°C, and at a temperature appropriately selected from 60°C to 160°C in terms of good reaction yield. It is preferably carried out.

The above-mentioned coupling reaction and boration reaction can be carried out after the reaction by appropriately combining general purification treatments such as recrystallization, column chromatography, sublimation purification, preparative HPLC, etc. to obtain the desired product. You can

The triazine compound (1) can be used for organic electronic devices such as organic electroluminescent devices and photoelectric devices.

<Material for organic electroluminescent device>
A material for an organic electroluminescence device according to an aspect of the present disclosure contains the triazine compound (1) described above.
The triazine compound (1) can be used, for example, as an electron transport material for an organic electroluminescence device. The material for organic electroluminescent devices containing the triazine compound (1) exhibits high luminous efficiency and long life characteristics, and contributes to the production of organic electroluminescent devices that can be used in various applications or under various environments.

<Organic electroluminescent device>
Hereinafter, an organic electroluminescence device containing the triazine compound (1) (hereinafter, may be simply referred to as an organic electroluminescence device) will be described.

An organic electroluminescent element according to one aspect of the present disclosure contains a triazine compound (1).
The configuration of the organic electroluminescent element is not particularly limited, but examples thereof include the configurations (i) to (v) shown below.

(I): Anode/light emitting layer/cathode (ii): Anode/hole transporting layer/light emitting layer/cathode (iii): Anode/light emitting layer/electron transporting layer/cathode (iv): Anode/hole transporting 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 it is composed of a light emitting layer and a layer between the light emitting layer and the cathode in view of excellent light emitting characteristics of the organic electroluminescent device. It is preferably contained in one or more layers selected from the group. Therefore, in the case of the configurations shown in (i) to (v) above, the triazine compound (1) may be contained in one or more layers selected from the group consisting of a light emitting layer, an electron transport layer, and an electron injection layer. preferable.

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

FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescence device containing a triazine compound according to an aspect of the present disclosure.
The organic electroluminescent device 100 includes 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, and conversely, 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, the hole injection layer 3 may be omitted, and the hole transport layer 4 may be directly provided on the anode 2. Good. In addition, a single layer having the functions of a plurality of layers, such as an electron injecting/transporting layer having both the function of the electron injection layer and the function of the electron transport layer in a single layer, It may be a configuration provided instead of. Further, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be composed of a plurality of layers.

<<Layer Containing Triazine Compound (1)>>
In the configuration example shown in FIG. 1, the organic electroluminescent device 100 contains the triazine compound (1) in one or more layers selected from the group consisting of the light emitting layer 5, the electron transport layer 6 and the electron injection layer 7. In particular, the electron transport layer 6 preferably contains the triazine compound (1). The triazine compound (1) may be contained in a plurality of layers included in the organic electroluminescence device.
In addition, below, the organic electroluminescent element 100 in which the electron carrying layer 6 contains the triazine compound (1) is demonstrated.

[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, and the like. Among these, a glass plate, a quartz plate, and a light-transmissive plastic film are preferable.
Examples of the light-transmissive plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyether imide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC). ), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.
It should be noted that in the case of a structure in which light emission is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

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

[Hole injection layer 3, hole transport layer 4]
A hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side between the anode 2 and a light emitting layer 5 described later.
The hole injection layer and the hole transport layer have a function of transmitting the holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer should be interposed between the anode and the light emitting layer. Causes many holes to be injected into the light emitting layer at a lower electric field.

Further, the hole injection layer and the hole transport layer also function as a layer having an electron barrier property. 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 blocked by the electron barrier existing at the interface between the light emitting layer and the hole injection layer and/or the hole transport layer. The leakage into the hole injection layer and/or the hole transport layer is suppressed. As a result, the electrons are accumulated at the interface in the light emitting layer, resulting in effects such as improvement in light emission efficiency, and an organic electroluminescent device having excellent light emitting performance can be obtained.

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

Specific examples of the material for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcones. Derivative, oxazole derivative, styrylanthracene derivative, fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aniline copolymer, conductive polymer oligomer (particularly thiophene oligomer), porphyrin compound, aromatic tertiary amine compound, styryl Examples thereof include amine compounds. Among these, a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound are preferable, and an aromatic tertiary amine compound is particularly preferable, from the viewpoint of good performance of the organic electroluminescent device.

Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl and 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-tolylamino) Phenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- 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-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino] Biphenyl (NPD), 4,4′,4″-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA) and the like can be mentioned.

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

The hole injection layer and the hole transport layer may have a single structure made of one kind or two or more kinds of materials, and may have a laminated structure made of a plurality of layers having the same composition or different compositions.

[Light emitting layer 5]
A light emitting layer 5 is provided between the hole transport layer 4 and an electron transport layer 6 described later.
Examples of the material of the light emitting layer include a phosphorescent light emitting material, a fluorescent light emitting material, and a heat-activated delayed fluorescent light emitting material. In the light emitting layer, electron-hole pairs are recombined, and as a result, light emission occurs.

The emissive layer may consist of a single low molecular weight material or a single polymeric material, but more commonly it consists of a host material doped with a guest compound. The emission mainly originates from the dopant and can have any color.

Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi(4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl), BCzVBi(4,4′-bis(9-ethyl-3-carbazovinylene)1, 1'-biphenyl), TBADN (2-tert-butyl-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 can be mentioned.

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

Examples of the phosphorescent dopant include organic metal complexes of transition metals such as iridium, platinum, palladium and osmium.

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

Further, 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 the layer (hole transport layer 4 or electron transport layer 6) adjacent to the light emitting layer. This can further increase the current efficiency of the organic electroluminescent device.

The light emitting layer may have a single-layer structure made of one or more kinds of materials, or a laminated structure made of a plurality of layers having the same composition 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 later.
The electron transport layer has a function of transmitting 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). In addition to the triazine compound (1), the electron transport layer may further include one or more kinds selected from conventionally known electron transport materials.
When the triazine compound (1) is not contained in the electron transport layer but is contained in the other layer, one or more kinds selected from conventionally known electron transport materials should be used as the electron transport material constituting the electron transport layer. You can

Examples of conventionally known electron transporting materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of the alkali metal complex, the alkaline earth metal complex, and the earth metal complex include 8-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato)zinc, and bis(8-hydroxyquinolinato)copper. , Bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, 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-quinolinate)(o -Cresolato) gallium, bis(2-methyl-8-quinolinato)-1-naphtholate aluminum, bis(2-methyl-8-quinolinato)-2-naphtholate gallium and the like.

The electron transport layer may have a single-layer structure composed of one or more materials, or a laminated structure composed of a plurality of layers having the same composition or different compositions.
In the organic electroluminescence device according to this aspect, an electron injection layer may be provided for the purpose of improving the electron injection property and improving device characteristics (for example, light emission efficiency, constant voltage drive, or high durability).

[Electron injection layer 7]
An electron injection layer 7 is provided between the electron transport layer 6 and a cathode 8 described later.
The electron injection layer has a function of transmitting 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 with a lower electric field.

Examples of the material for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane, and anthrone. Organic compounds are mentioned. The electron injection layer may be made of various oxides such as SiO ₂ , AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiO, TaO, TaON, TaN, C, nitrides, oxynitrides. Inorganic compounds such as

[Cathode 8]
A cathode 8 is provided on the electron injection layer 7.
In the case of an organic electroluminescence device having a structure in which only the light emission that has passed through the anode is taken out, the cathode can be formed of any conductive material.

Examples of the material of the cathode include a metal having a low work function (hereinafter, also referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof. Here, the metal having a low work function is, for example, a metal having a work function of 4 eV or less.
Specific examples of the material of the cathode include sodium, sodium-potassium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide (Al ₂ O ₃ ). Mixtures, indium, lithium/aluminum mixtures, rare earth metals and the like.
Among them, from the viewpoint of electron injecting property and durability against oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value, for example, a magnesium/silver mixture, magnesium /Aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide (Al ₂ O ₃ ) mixture, lithium/aluminum mixture and the like are preferable.

[Method of forming each layer]
Each of the layers described above excluding the electrodes (anode, cathode) is formed by thinning it by a known method such as a vacuum vapor deposition method, a spin coating method, a casting method, and an LB (Langmuir-Blodgett method) method. be able to. The material of each layer may be used alone, or may be used together with a material such as a binder resin and a solvent, if necessary.
The thickness of each layer thus formed is not particularly limited and may be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

The anode and the cathode can be formed by thinning the electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering, or a pattern having a desired shape may be formed by photolithography after forming a thin film by vapor deposition or sputtering.
The film thickness of the anode and the cathode is preferably 1 μm or less, more preferably 10 nm or more and 200 nm or less.

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

The organic electroluminescence device may be used as a kind of lamp for lighting or as an exposure light source, or a projection device of a type that projects an image on a screen or a display of a type that directly visually recognizes a still image or a moving image. It may be used as a device (display). When an organic electroluminescent element is used as a display device for reproducing a moving image, 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 manufactured by using two or more kinds of organic electroluminescent elements having different emission colors.

The triazine compound (1) can provide an organic electroluminescent device having remarkably excellent luminous efficiency and long-life characteristics when used as an electron transport layer, as compared with conventionally known triazine compounds. Further, the triazine compound (1) has high amorphous property due to its steric hindrance skeleton and has high film quality stability. Therefore, it is expected that the driving stability of the organic electroluminescent device and the luminous efficiency are improved. Moreover, the triazine compound (1) has high chemical stability due to its characteristic skeleton, and can contribute to prolonging the life of the organic electroluminescence device.

By using the triazine compound (1) as an electron transport layer of an organic electroluminescent device, it is possible to provide a triazine compound capable of achieving high voltage driving, high efficiency and long life of the device. Furthermore, it is possible to provide an organic electroluminescence device using the triazine compound (1), which can be driven at a low voltage, can be highly efficient, and can have a long life.

Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not construed as being limited to these examples.

[ ¹ H-NMR measurement]
Bruker ASCEND 400 (400 MHz; manufactured by BRUKER) was used for ¹ H-NMR measurement. ¹ H-NMR was measured using deuterated chloroform (CDCl ₃ ) as a measurement solvent and tetramethylsilane (TMS) as an internal standard substance. As reagents, commercially available products were used.

[DSC measurement (glass transition temperature, crystallization temperature, melting point)]
The glass transition temperature, the crystallization temperature, and the melting point were measured using a DSC (Differential Scanning Calorimetry) device DSC7020 (product name, manufactured by Hitachi High-Tech Science Co., Ltd.). Aluminum oxide (Al ₂ O ₃ ) was used as a reference in the DSC measurement, and the sample was measured at 10 mg.
As a pretreatment for the measurement, the sample was melted by increasing the temperature from 30° C. to a temperature equal to or higher than the melting point at a rate of 15° C./min, and then rapidly cooled with liquid nitrogen. Subsequently, the temperature of the pretreated sample was increased from 30° C. at a rate of 5° C./min, and the glass transition temperature, crystallization temperature, and melting point were measured.

[FDMS measurement]
The FDMS measurement was performed using M-80B manufactured by Hitachi, Ltd.

[Measurement of light emission characteristics]
The emission characteristics of the organic electroluminescence device were evaluated under a 25° C. environment by applying a direct current to the devices produced in the respective examples (described later) and using a luminance meter BM-9 (product name, manufactured by Topcon Technohouse). did.

Synthesis Example-1

Thionyl chloride (295 g, 2.5 mol) was added to 4-bromo-3-chlorobenzoic acid (152 g, 650 mmol) and DMF (2 mL), and the mixture was heated under reflux for 20 hours. After cooling to room temperature, the low boiling fraction was distilled off under reduced pressure to obtain 4-bromo-3-chlorobenzoyl chloride. This product was used in the next step without purification.
4-Bromo-3-chlorobenzoyl chloride (164 g, 650 mmol) and benzonitrile (146 g, 1.4 mol) were suspended in monochlorobenzene (1.3 L) under an argon atmosphere. While cooling this suspension in an ice bath, antimony chloride (82 mL, 650 mmol) was added dropwise, and the mixture was stirred at 0°C for 15 minutes and then at 70°C for 12 hours. After the reaction, the reaction mixture was added dropwise to 30%-aqueous ammonia (2 L) while cooling with an ice bath, and the mixture was stirred at room temperature for 8 hours. The resulting solid was collected by filtration and washed with water. The obtained solid was suspended in toluene (5 L), and heated and stirred at 110°C for 30 minutes. This suspension was filtered, and low-boiling components were distilled off under reduced pressure from the filtrate. The obtained solid was washed with methanol and hexane, and the crude product obtained was repeatedly recrystallized from toluene to give 2-(4-bromo-3-chlorophenyl)-4,6-diphenyl- as a white solid. 1,3,5-triazine (150 g, 55%) was obtained.

¹ H-NMR (CDCl ₃ ): δ 7.58-7.66 (m, 6H), 7.82 (d, J=8.4 Hz, 1H), 8.52 (dd, J=8.4, 2) 0.0 Hz, 1 H), 8.76 (brd, J=6.7 Hz, 4 H), 8.84 (d, J=2.0 Hz, 1 H).

Synthesis Example-1

Under an argon atmosphere, 2-(4-bromo-3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (10.1 g, 24 mmol), bispinacolatodiborone (7.25 g, 29 mmol), Bis(triphenylphosphine)palladium dichloride (842 mg, 1.2 mmol) and potassium acetate (8.50 g, 86 mmol) were suspended in THF (48 mL) and stirred at 80° C. for 21 hours. After cooling to room temperature, chloroform was added to the reaction mixture to extract the organic layer, and the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, and saturated saline. After adding sodium sulfate and activated carbon to the organic layer and stirring, the solid content was removed by filtration through Celite, and the solvent was evaporated. The crude product was suspended in hexane and collected by filtration to give 2-[3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- as a yellow solid. Yield)phenyl]-4,6-diphenyl-1,3,5-triazine was obtained (6.5 g, 52%).

¹ H-NMR (CDCl ₃ ): δ1.43 (s, 12H), 7.57-7.65 (m, 6H), 7.88 (d, J=7.8Hz, 1H), 8.61( dd, J=7.8 Hz, 1.4 Hz, 1H), 8.75 (d, J=1.4 Hz, 1H), 8.78 (brd, J=6.6 Hz, 4H).

Synthesis Example-2

2-[3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3 under an argon atmosphere. 5-triazine (6.40 g, 14 mmol), 3-bromo-2,6-dimethylpyridine (2.1 mL, 16 mmol), and bis(triphenylphosphine)palladium dichloride (295 mg, 0.42 mmol) in THF (28 mL). ). A 2.0 M potassium phosphate aqueous solution (25 mL) was added to this suspension, and the mixture was stirred at 80° C. for about 16 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture and the precipitated solid was collected by filtration and washed with water and methanol. The obtained solid was dissolved in chloroform (600 mL), the insoluble portion was filtered with filter paper, activated carbon was added to the filtrate, and the mixture was stirred for a while. After stirring, Celite filtration was performed, and low boiling components were distilled off from the filtrate to obtain a crudely purified product. By repeatedly recrystallizing the crude product with toluene, the desired product 2-[3-chloro-4-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1, 3,5-triazine was obtained (2.8 g, 45%).

¹ H-NMR (CDCl ₃ ): δ 2.40 (s, 3H), 2.63 (s, 3H), 7.12 (d, J=7.8 Hz, 1H), 7.43 (d, J=). 8.0 Hz, 1 H), 7.44 (d, J=7.8 Hz, 1 H), 7.57-7.67 (m, 6 H), 8.73 (dd, J=8.0 Hz, 1.6 Hz) , 1H), 8.80 (brd, J=6.6 Hz, 4H), 8.88 (d, J=1.6 Hz, 1H).

Synthesis Example-3

2-[3-chloro-4-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (2.53 g, 5.6 mmol) under an argon atmosphere. , And 9-phenanthreneboronic acid (1.88 g, 8.45 mmol) were suspended in a mixed solvent of 1-butanol (56 mL) and toluene (51 mL). To this suspension was added a solution of palladium acetate (126 mg, 0.56 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (476 mg, 1.1 mmol) in toluene (5 mL), and 5 M-. Aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at 120° C. for 41 hours. After allowing to cool to room temperature, ethyl acetate and chloroform were added to the reaction mixture to extract an organic layer, and the organic layer was washed with water and then with saturated saline. Sodium sulfate and activated carbon were added to the organic layer, and the mixture was stirred and then filtered through Celite to distill off low-boiling components. The obtained crude product was recrystallized from toluene and purified by silica gel column chromatography (chloroform:ethyl acetate=2:1) to give the desired product, 2-[3-(phenanthren-9-yl)-4-. (2,6-Dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (Compound A-39) was obtained (1.6 g, 48%).

¹ H-NMR (CDCl ₃ ): δ2.44 (s, 3H), 2.83 (brs, 3H), 6.56 (brs, 1H), 7.52-7.71 (m, 14H), 7 .82 (brs, 1H), 8.67 (d, J=8.0 Hz, 1H), 8.70 (brs, 1H), 8.76 (brd, J=6.8 Hz, 4H), 8.88. (Brs, 1H) 8.94 (dd, J=8.0 Hz, 1.8 Hz, 1H).

The glass transition temperature of the obtained compound A-39 was 135° C., the melting point thereof was 292° C., and the crystallization temperature was not detected.

Synthesis Example-4

Under an argon atmosphere, 2-(4-bromo-3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (8.03 g, 19 mmol), 2-biphenylboronic acid (4.52 g, 23 mmol), Bis(triphenylphosphine)palladium dichloride (667 mg, 1.0 mmol) and 2M-potassium phosphate aqueous solution (34 mL, 68 mmol) were suspended in THF (190 mL), and the mixture was stirred at 80° C. for 21 hours. After allowing to cool to room temperature, ethyl acetate and water were added to the reaction mixture to extract an organic layer, and the organic layer was washed with water and then with saturated saline. Sodium sulfate and activated carbon were added to the organic layer and the mixture was stirred. Chloroform was further added to suspend the solution, the solid content was removed by Celite filtration, and the low-boiling component was distilled off under reduced pressure from the resulting solution. The crude product was recrystallized from toluene to give 2-[2-chloro-1,1':2',1"-terphenyl-4-yl]-4,6 as a white solid. -Diphenyl-1,3,5-triazine was obtained (yield 6.70 g, 71% yield).

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.21 (m, 5H), 7.31 (d, J=8.0 Hz, 1H), 7.43 (d, J=7). .3 Hz, 1 H), 7.45-7.53 (m, 3 H), 7.55-7.64 (m, 6 H), 8.54 (dd, J=8.0, 1.6 Hz, 1 H) , 8.76 (brd, J=7.4 Hz, 5H).

Synthesis Example-5

The resulting 2-[2-chloro-1,1′:2′,1″-terphenyl-4-yl]-4,6-diphenyl-1,3,5-triazine (3.37 g) under an argon atmosphere. , 6.8 mmol), 9-phenanthreneboronic acid (1.96 g, 8.8 mmol), palladium acetate (76 mg, 0.36 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl( 324 mg, 0.68 mmol) and 5M aqueous sodium hydroxide solution (5.4 mL, 27 mmol) were suspended in THF (68 mL) and stirred for 20 hours at 80° C. After cooling to room temperature, chloroform and water were added. The organic layer was extracted with water, and the organic layer was washed with water and then with saturated brine, sodium sulfate and activated carbon were added to the organic layer, and the mixture was stirred. The crude product was recrystallized from toluene to give white solid 4,6-diphenyl-2-[2-(9-phenanthrenyl)-1,1':2'. , 1″-terphenyl-4-yl]-1,3,5-triazine (Compound A-3) was obtained (amount 3.30 g, yield 75%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 6.44-7.25 (m, 9H), 7.38-7.94 (m, 13H), 8.60-8.65 (m, 3H). ), 8.74 (d, J=7.3 Hz, 4H), 8.94 (brd, J=7.3 Hz, 1H).

Synthesis Example-6

Under an atmosphere of argon, 2-[3"-chloro-1,1':2',1"-terphenyl-5"-yl]-4,6-diphenyl-1,3,5-triazine (3.34 g , 6.7 mmol), 9,9-dimethyl-2-fluoreneboronic acid (2.40 g, 10 mmol), palladium acetate (76 mg, 0.34 mmol), and 2-dicyclohexylphosphino-2′,4′,6′. -Triisopropylbiphenyl (286 mg, 0.67 mmol) was suspended in 1,4-dioxane (67 mL), 2 M aqueous sodium hydroxide solution (6.1 mL) was added to the suspension, and the mixture was stirred at 110°C. The mixture was stirred for 40 hours, allowed to cool to room temperature, water and chloroform were added to the reaction mixture, the organic layer was extracted, activated carbon and sodium sulfate were added to the extract, and the mixture was stirred for a while. The low-boiling fraction was distilled off, the crude product was recrystallized from toluene (115° C., 5 mL), and the precipitated solid was separated by filtration. ), a white solid 2-[2-(9,9-dimethyl-9H-fluoren-2-yl)-1,1′:2′,1″-terphenyl-4-yl]-4. , 6-Diphenyl-1,3,5-triazine (Compound A-98) was obtained (2.3 g, 52%).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.81 (dd, J=8.0 Hz, 1.8 Hz, 1 H), 8.78 (ddd, J=6.6 Hz, 1.6 Hz, 1. 4 Hz, 4 H), 8.68 (d, J=1.8 Hz, 1 H), 7.54-7.63 (m, 7 H) 7.43-7.48 (m, 2 H), 7.29-7 .41 (m, 4H), 7.15 (J=7.6 Hz, 1.2 Hz, 1H), 7.07 (t, J=7.4 Hz, 4H), 6.79 (t, J=7. 8 Hz, 2 H), 6.79 (d, J=1.2 Hz, 1 H), 6.72 (dd, J=7.8 Hz, 1.6 Hz, 1 H), 6.64 (dd, J=8.4 Hz) , 1.4 Hz, 1H), 1.28 (s, 3H), 1.19 (s, 3H).

Synthesis Example-7
4,6-Diphenyl-2-[2-(phenanthrene-9-yl)-3'-(2,6-phenylpyridin-4-yl)biphenyl-4-yl]-1,3,5-triazine (Compound A-49) was synthesized according to the following synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-49 had FDMS=791.

Synthesis Example-8
4,6-diphenyl-2-[2-(phenanthrene-9-yl)-4'-(2-pyridyl)biphenyl-4-yl]-1,3,5-triazine (Compound A-53) was prepared as follows. It was synthesized according to the synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-53 had FDMS=791.

Synthesis Example-9
4,6-diphenyl-2-[2-(phenanthrene-9-yl)-4'-(3-pyridyl)biphenyl-4-yl]-1,3,5-triazine (Compound A-54) was prepared as follows. It was synthesized according to the synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-54 had FDMS=639.

Synthesis Example-10
4,6-diphenyl-2-[2-(phenanthrene-9-yl)-3'-(3-pyridyl)biphenyl-4-yl]-1,3,5-triazine (Compound A-58) was prepared as follows. It was synthesized according to the synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-58 had FDMS=639.

Synthesis Example-11
4,6-diphenyl-2-[2-(phenanthrene-9-yl)-2'-(3-pyridyl)biphenyl-4-yl]-1,3,5-triazine (Compound A-62) was prepared as follows. It was synthesized according to the synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-62 had FDMS=639.

Synthesis Example-12
4,6-Diphenyl-2-[2-(anthracen-9-yl)-biphenyl-4-yl]-1,3,5-triazine (Compound A-129) was synthesized according to the following synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-129 was FDMS=639.

Synthesis Example-13
4,6-Diphenyl-2-[2-(anthracen-9-yl)-1,1′:2′,1″-terphenyl-4-yl]-1,3,5-triazine (Compound A- 130) was synthesized according to the synthetic route below. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-130 was FDMS=638.

Synthesis Example-14
4,6-diphenyl-2-[2-(dibenzofuran-4-yl)-4'-(3-pyridyl)biphenyl-4-yl]-1,3,5-triazine (Compound A-269) was prepared as follows. It was synthesized according to the synthetic route. The synthesis conditions were the same as in Synthesis Examples 1 to 6. The obtained compound A-54 had FDMS=629.

Reference example-1
2-[3-(4-Methyl-3-pyridyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl- which is the compound described in Synthesis Example 2 of JP-A-2017-178931. 1,3,5-triazine (ETL-1 below) was synthesized and its DSC measurement was carried out. The glass transition temperature of this compound was 113°C, the crystallization temperature was 197°C, and the melting point was 240°C. The compound was synthesized by the method described in JP-A-2017-178931, and the DSC measurement was conducted under the same conditions as in Synthesis Example-1 in the present specification (conditions described in paragraph [0090]). went.

Reference example-2

Under a nitrogen atmosphere, 2-[3-chloro-5-(phenanthrene-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 (55.0 mg, 0.12 mmol), 1,4 -Dioxane (50 mL) and 2M-tripotassium phosphate aqueous solution (2.9 mL, 5.8 mmol) were added to a 300 mL four-necked flask, and the mixture was stirred at 95°C for 6 hours. The obtained reaction liquid was allowed 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 hexane to give a gray powder. The obtained gray powder was purified by recrystallizing with toluene to obtain the desired product, 4,6-diphenyl-2-[5-(phenanthren-9-yl)-biphenyl-3-yl]-1,3. A gray powder of 5-triazine (Compound ETL-2) (yield 700 mg, yield 65%) was obtained.

¹ H-NMR (CDCl ₃ ): δ7.45 (t, J=7.3 Hz, 1H), 7.52-7.63 (m, 9H), 7.67 (t, J=7.2 Hz, 1H). ), 7.73 (t, J=7.8 Hz, 1.3 Hz, 2H), 7.84 (dd, J=8.1 Hz, 1.0 Hz, 2H), 7.88 (s, 1H), 7 .98 (dd, J=7.8 Hz, 1.4 Hz, 1H), 8.01-8.04 (m, 2H), 8.77-8.80 (m, 5H), 8.85 (d, J=8.3 Hz, 1 H), 8.93 (t, J=1.7 Hz, 1 H), 9.12 (t, J=1.7 Hz, 1 H).

Reference example-3

4,6-Diphenyl-2-[6-(triphenylen-1-yl)-biphenyl-3-yl]-1,3,5-triazine (ETL-3) was added to Example 7 of WO2018/095390. It was synthesized by the method described in.
FDMS: 611

The glass transition temperature of the obtained compound ETL-2 was 108°C, the crystallization temperature was 207°C, and the melting point was 260°C. The DSC measurement was performed under the same conditions as in Synthesis Example-1 of the present application.

From the above results, it was found that the triazine compound obtained in Synthesis Example-3 has a higher glass transition temperature than the conventionally known triazine compounds obtained in Reference Example-1 and Reference Example-2. Furthermore, it was found that the triazine compound obtained in Synthesis Example-3 had low crystallinity due to the characteristics of its skeleton, and the crystallization temperature was not detected or had a high crystallization temperature. Therefore, the triazine compound (1) can be expected to have a high amorphous property when forming a thin film, and it is presumed that the triazine compound (1) exhibits high driving stability and high luminous efficiency when an organic electroluminescent device using the triazine compound (1) is produced. To be done.

Then, device evaluation was carried out using the obtained compound.

[Evaluation as the electron transport layer 6]
Element Example-1 (see FIG. 2)
(Preparation of substrate 1 and anode 2)
As the substrate 1 having the anode 2 on its surface, a glass substrate with an ITO transparent electrode in which a 2 mm wide indium-tin oxide (ITO) film (film thickness 110 nm) was patterned in a stripe shape was prepared. Next, this substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet ray cleaning.

(Preparation for vacuum deposition)
Each layer was vacuum-deposited by a vacuum vapor deposition method on the substrate subjected to the surface treatment after washing to form each layer in a laminated manner.
First, the glass substrate was introduced into a vacuum vapor deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa. Then, the respective layers were formed in the following order according to the film forming conditions of each layer. In addition, each organic material was formed into a film by a resistance heating method.

(Preparation 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-fluorene-2 -Amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were formed into a 10 nm film at a ratio of 99:1 (mass ratio). Hole injection 3 was made. 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-fluorene-2 -Amine was formed into a film with a thickness of 85 nm at a rate of 0.2 nm/sec to form the 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 5 nm film at a rate of 0.15 nm/sec. The second hole transport layer 42 was produced.

(Production 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 20 nm was deposited at a ratio of 95:5 (mass ratio) to form a light emitting layer 5. The film formation rate was 0.1 nm/sec.

(Preparation of hole blocking layer 9)
Sublimated and purified 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4,6-diphenyl-1,3,5- A film of triazine was formed to a thickness of 6 nm at a rate of 0.05 nm/sec to form the hole blocking layer 9.

(Production of electron transport layer 6)
2-[3-(phenanthren-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (synthesized in Synthesis Example-3 The compound A-39) and 8-hydroxyquinolinolato lithium (hereinafter, Liq) were formed into a 25 nm film at a ratio of 50:50 (mass ratio) to prepare an electron transport layer 6. The film formation rate was 0.15 nm/sec.

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

(Production of cathode 8)
Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe (anode 2) on the substrate 1, and the cathode 8 was formed. The cathode was formed into a two-layer structure by depositing silver/magnesium (mass ratio 1/10) and silver in this order at 80 nm and 20 nm, respectively. The silver/magnesium film formation rate was 0.5 nm/sec, and the silver film formation rate was 0.2 nm/sec.

As described above, an organic electroluminescence device 100 having a light emitting area of 4 mm ² as shown in FIG. 2 was produced. The respective film thicknesses were measured with a stylus type film thickness meter (DEKTAK, manufactured by Bruker).

Further, this element was sealed in a nitrogen atmosphere glove box having oxygen and water concentrations of 1 ppm or less. The sealing was performed by using a bisphenol F type epoxy resin (manufactured by Nagase Chemtex) for the glass sealing cap and the film-forming substrate (element).

Element Example-2
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq were deposited at a ratio of 50:50 (mass ratio) at a thickness of 25 nm (deposition rate: 0.15 nm/sec), instead of Compound A-49 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Device Example-3
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq were deposited at a ratio of 50:50 (mass ratio) at a ratio of 25 nm (deposition rate: 0.15 nm/sec), instead of Compound A-53 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Device Example-4
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq at a ratio of 50:50 (mass ratio) at a ratio of 25 nm (deposition rate 0.15 nm/sec), instead of Compound A-54 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Element Example-5
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq were deposited at a ratio of 50:50 (mass ratio) at a ratio of 25 nm (deposition rate: 0.15 nm/sec), instead of Compound A-58 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Element Example-6
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq were deposited at a ratio of 50:50 (mass ratio) at a film thickness of 25 nm (deposition rate: 0.15 nm/sec), Compound A-62 and Liq were 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Element Example-7
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq were deposited at a ratio of 50:50 (mass ratio) at a rate of 25 nm (deposition rate: 0.15 nm/sec), instead of Compound A-182 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Element Example-8
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq at a ratio of 50:50 (mass ratio) at a ratio of 25 nm (film formation rate 0.15 nm/sec), instead of Compound A-269 and Liq at 50:50. An organic electroluminescence device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (film formation rate: 0.15 nm/sec).

Element reference example-1
In Device Example-1, 2-[3-(phenanthrene-9-yl)-(2,6-dimethylpyridin-3-yl)phenyl]-4,6-diphenyl-1,3 was formed on the electron transport layer 6. , 5-triazine (Compound A-39) and Liq at a ratio of 50:50 (mass ratio) at a film thickness of 25 nm (deposition rate 0.15 nm/sec), ETL-1 and Liq at 50:50 ( An organic electroluminescent device was produced in the same manner as in Example 1 except that the film was formed at a ratio of (mass ratio) of 25 nm (deposition rate: 0.15 nm/sec).

A direct current was applied to the produced organic electroluminescent device, and the light emitting characteristics were evaluated according to the method described in the above measurement of light emitting characteristics.
As the light emission characteristics, the voltage (V) when a current density of 10 mA/cm ² was passed and the current efficiency (cd/A) were measured, and the device life during continuous lighting was measured. The device lifetime was measured luminance decay time at the time of continuous lighting when driving the initial luminance 1000 cd / m ^2, to measure the time required until the luminance (cd / m ²⁾ is reduced 3%. The values of voltage (V), current efficiency (cd/A), and life are expressed as relative values when element reference example-1 is set to 100. The results are shown in Table 1.

[Evaluation as hole blocking layer 9]
Element Example-9
In the device example-1, the hole blocking layer 9 was formed with 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4. , 6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec), and compound A-3 was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec). Produced an organic electroluminescent device in the same manner as in Device Example-1.

Element Example-10
In the device example-1, the hole blocking layer 9 was formed with 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4. , 6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec), and compound A-98 was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec). Produced an organic electroluminescent device in the same manner as in Device Example-1.

Element Example-11
In the device example-1, the hole blocking layer 9 was formed with 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4. , 6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec), and compound A-129 was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec). Produced an organic electroluminescent device in the same manner as in Device Example-1.

Element Example-12
In the device example-1, the hole blocking layer 9 was formed with 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4. , 6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec), and compound A-130 was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec). Produced an organic electroluminescent device in the same manner as in Device Example-1.

Element reference example-2
In the device example-1, the hole blocking layer 9 was formed with 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)[1,1′-biphenyl]-3-yl]-4. , 6-diphenyl-1,3,5-triazine was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec), and compound ETL-3 was deposited to a thickness of 6 nm (deposition rate of 0.05 nm/sec). Produced an organic electroluminescent device in the same manner as in Device Example-1.

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

As the light emission characteristics, the voltage (V) when a current density of 10 mA/cm ² was passed and the current efficiency (cd/A) were measured, and the device life during continuous lighting was measured. The device lifetime was measured luminance decay time at the time of continuous lighting when driving the initial luminance 1000 cd / m ^2, to measure the time required until the luminance (cd / m ²⁾ is reduced 3%. The values of voltage (V), current efficiency (cd/A), and life are expressed as relative values when element reference example-2 is 100. The results are shown in Table 2.

From Tables 1 and 2, it was found that the organic electroluminescent device using the triazine compound (1) was highly excellent in voltage, luminous efficiency and device life as compared with 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 51. First hole transport layer 52. Second hole transport layer 100. Organic electroluminescent device

Claims (10)

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 ³ is a tricyclic or tetracyclic fused ring,
Aromatic hydrocarbon group,
A nitrogen-containing aromatic group consisting of only a 6-membered ring, or
Represents a heteroaromatic group in which the heteroatom is a Group 16 element;
Ar ⁴ represents a phenyl group, an azaphenyl group, a diazaphenyl group, a naphthyl group, an azanaphthyl group, or a diazanaphthyl group;
Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are each independently one or more selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group. Optionally substituted with groups;
X represents a phenylene group, a naphthylene group, an azaphenylene group, a diazaphenylene group, an azanaphthylene group or a diazanaphthylene group;
p represents 0, 1 or 2;
When p is 2, the two Xs may be the same or different. The triazine compound according to claim 1, wherein Ar ¹ and Ar ² are the same group. The triazine compound according to claim 1 or 2, wherein Ar ¹ and Ar ² each independently represent an unsubstituted phenyl group, biphenylyl group or naphthyl group. Ar ³ may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, a phenyl group, a naphthyl group, an azaphenyl group, a diazaphenyl group, an azanaphthyl group and a diazanaphthyl group, a tricyclic or The triazine compound according to any one of claims 1 to 3, which is a tetracyclic condensed aromatic hydrocarbon group. The triazine compound according to any one of claims 1 to 4, wherein Ar ³ is an unsubstituted tricyclic or tetracyclic fused aromatic hydrocarbon group. Ar ⁴ represents a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a naphthyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a diphenylpyridyl group, a pyrimidyl group, a methylpyrimidyl group, a dimethylpyrimidyl group. The triazine compound according to any one of claims 1 to 5, which is a dil group, a phenylpyrimidyl group, a diphenylpyrimidyl group, a pyrazyl group, a methylpyrazyl group or a phenylpyrazyl group. The triazine compound according to any one of claims 1 to 6, wherein X is a phenylene group or an azaphenylene group. The triazine compound according to any one of claims 1 to 7, wherein p is 0 or 1. A material for an organic electroluminescence device, containing the triazine compound according to claim 1. An organic electroluminescent device containing the triazine compound according to claim 1.