JP2023066154A - Alkyl triazine compound - Google Patents

Abstract

To provide a triazine compound that contributes to forming an organic electroluminescent device having excellent two properties of drive voltage and luminous efficiency, and has a partial structure contributing to luminous efficiency properties.SOLUTION: The present invention provides a compound represented by the formula (1) (where at least one of R1-R4 is a C1-18 alkyl group with the remainder being an optionally substituted C6-18 aromatic hydrocarbon group or the like, and R5 is a hydrogen atom, an optionally substituted C6-18 aromatic hydrocarbon group or the like, or an aromatic substituted silyl group).SELECTED DRAWING: Figure 1

Description

The present disclosure relates to an alkyltriazine compound, and further to a material for an organic electroluminescent device, an electron-transporting material for an organic electroluminescent device, and an organic electroluminescent device containing the alkyltriazine compound.

Organic electroluminescence devices have begun to be put into practical use, mainly for small mobile applications. However, performance improvement is essential for further expansion of applications, and materials with low-voltage drive characteristics, high luminous efficiency characteristics, and long-life characteristics are in demand. Patent document 1 discloses a triazine compound which is a material for an organic electroluminescent device having a long life and excellent luminescence properties. Moreover, Patent Document 2 discloses that a material into which an alkylpyrimidyl group is introduced is effective in improving the characteristics of an organic electroluminescence device.

Japanese Patent Application Laid-Open No. 2007-314503 JP 2015-027986 A

With respect to the three characteristics of driving voltage, luminous efficiency, and life characteristics required for expanding the range of applications, the triazine compounds according to Patent Documents 1 and 2 are said to sufficiently satisfy these depending on the application. Therefore, there is a demand for a material that achieves the above three characteristics at a higher level. In particular, there is a need for materials for organic electroluminescent devices that have better properties than known materials in two properties, luminous efficiency and driving voltage.

Therefore, one aspect of the present invention is directed to providing a triazine compound having a partial structure that contributes to luminous efficiency characteristics, which contributes to the formation of an organic electroluminescent device that is excellent in both characteristics of driving voltage and luminous efficiency. there is Further, still another aspect of the present invention is directed to providing an organic electroluminescence device exhibiting high luminous efficiency and long life characteristics.

As a result of intensive studies to solve the above problems, the present inventors have found that by introducing a triazyl group substituted with an alkyl group into the triazine derivative used in the electron transport layer, the device efficiency can be improved and the driving voltage can be reduced. The present inventors have found that it is effective in reducing this, and have completed the present invention. That is, the present invention relates to the following (a) to (f).

(a) an alkyltriazine compound represented by formula (1);

During the ceremony,
At least one of R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 18 carbon atoms, and the remainder of R ¹ , R ² , R ³ and R ⁴ each have an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted with an alkyl group, phenyl group, pyridyl group or cyano group having 1 to 18 carbon atoms; or an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or A heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring optionally substituted with a cyano group; represents:
L represents a divalent aromatic hydrocarbon group consisting only of a 6-membered ring or a divalent nitrogen-containing aromatic group consisting only of a 6-membered ring:
p represents 0, 1 or 2:
q represents 0, 1 or 2:
When p is 2, L may be the same or different:
R ⁵ is a hydrogen atom; an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted by an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; an alkyl group having 1 to 18 carbon atoms; a heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring optionally substituted with a group, a phenyl group, a pyridyl group or a cyano group; or a silyl group represented by Si(Ar) ₃ ; :
Each Ar independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms.

(b) Of R ¹ , R ² , R ³ and R ⁴ , R ¹ , R ² , R ³ and R ⁴ other than alkyl groups having 1 to 18 carbon atoms are alkyl groups having 1 to 6 carbon atoms The alkyltriazine compound according to (a), which is an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted with a phenyl group, a pyridyl group or a cyano group.

(c) The alkyltriazine compound according to (a) or (b), wherein L is a divalent aromatic hydrocarbon group composed only of 6-membered rings.

(d) the alkyltriazine compound according to any one of (a) to (c), wherein p is 0 or 1;

(E) The alkyltriazine compound according to any one of (I) to (D), wherein p is 0.

(f) R ⁵ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group; or a silyl group represented by Si(Ar) ₃ ; the alkyltriazine compound according to any one of (a) to (e).

(g) R ⁵ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group; or a triphenylsilyl group; the alkyltriazine compound according to any one of (a) to (f).

(h) The alkyltriazine compound according to any one of (a) to (g), wherein q is 0 or 1.

(i) at least one of R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 6 carbon atoms, and the remaining R ¹ , R ² , R ³ and R ⁴ each have 6 carbon atoms; The alkyltriazine compound according to any one of (i) to (h), which is an aromatic hydrocarbon group of 1 to 18.

(J) at least one of R ¹ , R ² , R ³ and R ⁴ is a methyl group, and the remaining R ¹ , R ² , R ³ and R ⁴ are each aromatic carbonized aromatic having 6 to 12 carbon atoms; The alkyltriazine compound according to any one of (i) to (li), which is a hydrogen group.

(i) The alkyltriazine compound according to (i), represented by any one of the following formulas A-1 to A-8.

(w) A material for an organic electroluminescence device, containing the alkyltriazine compound according to any one of (a) to (l).

(W) An electron-transporting material for an organic electroluminescence device, containing the alkyltriazine compound according to any one of (I) to (L).

(f) An organic electroluminescence device containing the alkyltriazine compound according to any one of (a) to (r).

According to one aspect of the present invention, it is possible to provide an alkyltriazine compound that contributes to the formation of an organic electroluminescent device that exhibits low-voltage drive characteristics and luminous efficiency characteristics at a high level. Further, according to another aspect of the present invention, it is possible to provide a material for an organic electroluminescence device containing the alkyltriazine compound. According to still another aspect of the present invention, it is possible to provide an organic electroluminescence device exhibiting high luminous efficiency and long life characteristics.

1 is a schematic cross-sectional view of a first preferred embodiment of an organic electric field element containing an alkyltriazine compound, which is one aspect of the present invention. FIG. 1 is a schematic cross-sectional view of a second preferred embodiment of an organic electric field element containing an alkyltriazine compound, which is one aspect of the present invention. FIG.

The alkyltriazine compound (hereinafter sometimes referred to as alkyltriazine compound (1)) according to one embodiment of the present invention is described in detail below.

<Alkyltriazine compound (1)>
Alkyltriazine compound (1) according to one aspect of the present invention is a triazine compound represented by formula (1):

[Regarding R ¹ , R ² , R ³ and R ⁴ ]
R ¹ , R ² , R ³ and R ⁴ may each independently be substituted with an alkyl group having 1 to 18 carbon atoms; an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; an aromatic hydrocarbon group having 6 to 18 carbon atoms; or an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group, or a cyano group having 4 to 17 carbon atoms composed only of a 6-membered ring optionally substituted with a cyano group. represents a heteroaromatic group of However, at least one of R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 18 carbon atoms.

In an embodiment of the present invention, "aromatic hydrocarbon group" means a group composed of one or more aromatic rings. The aromatic hydrocarbon group may be a single aromatic ring group, a group formed by connecting a plurality of aromatic ring groups via carbon bonds, or a condensed polycyclic aromatic may be a family group.

Further, the "heteroaromatic group" may be composed of only a 6-membered ring, and may be a group of one heteroaromatic ring, or a plurality of aromatic rings containing a heteroaromatic ring. It may be a group formed by connecting the groups with carbon bonds, or a condensed polycyclic heteroaromatic group having a structure in which a plurality of aromatic ring groups containing a heteroaromatic ring are condensed. good.

Examples of R ¹ , R ² , R ³ and R ⁴ include methyl group, cyclohexylmethyl group, ethyl group, 2-cyclopentylethyl group, propyl group, 2-methylpropyl group, 2,2-dimethylpropyl group, 3 -cyclopropylpropyl group, isopropyl group, cyclopropyl group, butyl group, 2-methylbutyl group, 3-methylbutyl group, 1-methylpropyl group, 1,2-dimethylpropyl group, 1,1-dimethylethyl group, cyclobutyl group , pentyl group, 2-methylpentyl group, 3-ethylpentyl group, 2,4-dimethylpentyl group, 2-pentyl group, 2-methylpentan-2-yl group, 4,4-dimethylpentan-2-yl group , 3-pentyl group, 3-ethylpentan-3-yl group, cyclopentyl group, 2,5-dimethylcyclopentyl group, 3-ethylcyclopentyl group, hexyl group, 2-methylhexyl group, 3,3-dimethylhexyl group, 4-ethylhexyl group, 2-hexyl group, 2-methylhexan-2-yl group, 5,5-dimethylhexan-2-yl group, 3-hexyl group, 2,4-dimethylhexan-3-yl group, cyclohexyl group, 4-ethylcyclohexyl group, 4-propylcyclohexyl group, 4,4-dimethylcyclohexyl group, heptyl group, 2-heptyl group, 3-heptyl group, 4-heptyl group, bicyclo[2.2.1]heptyl group , octyl group, 2-octyl group, 3-octyl group, 4-octyl group, cyclooctyl group, bicyclo [2.2.2] octyl group, nonyl group, 5-nonyl group, decyl group, 2-decyl group, 5-decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, biphenyl-2-yl group, biphenyl -3-yl group, biphenyl-4-yl group, 3-[1:1′,4′:1″]terphenyl group, 4-[1:1′,4′:1″]terphenyl group , (3′-cyano) biphenyl-2-yl group, (3′-cyano) biphenyl-3-yl group, (3′-cyano) biphenyl-4-yl group, (3′-cyano) biphenyl-2- yl group, (4'-cyano)biphenyl-3-yl group, (4'-cyano)biphenyl-4-yl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3,5 -dimethylphenyl group, 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3-(2- naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,5-dicyanophenyl group, 2-cyanophenyl group, 3-cyano Phenyl group, 4-cyanophenyl group, 3,5-dicyanophenyl group, 2-(2-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 2-(4-pyridyl)phenyl group, 3-( 3-pyridyl)phenyl group, 4-(2-pyridyl)phenyl group, 3,5-bis(2-pyridyl)phenyl group, (3'-cyano)biphenyl-2-yl group, (3'-cyano)biphenyl -3-yl group, (3'-cyano) biphenyl-4-yl group, (3'-cyano) biphenyl-2-yl group, (4'-cyano) biphenylyl-3-yl group, (4'-cyano ) biphenyl-4-yl group, 2-(4-pyridyl)biphenyl-4-yl group, 3′-(3-pyridyl)biphenyl-4-yl group, 4′-(4-pyridyl)biphenyl-4-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyrazyl group, 2-methylpyridin-2-yl group, 3-methyl pyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 2-methylpyridin-3-yl group, 4-methylpyridin-3-yl group, 5-methyl pyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 3-methylpyridin-4-yl group, 2,6-dimethylpyridin-3-yl group, 2 , 4-dimethylpyridin-3-yl group, 2,5-dimethylpyridin-3-yl group, 2-phenylpyridin-2-yl group, 3-phenylpyridin-2-yl group, 4-phenylpyridin-2- yl group, 5-phenylpyridin-2-yl group, 2-phenylpyridin-3-yl group, 4-phenylpyridin-3-yl group, 5-phenylpyridin-3-yl group, 6-phenylpyridin-3- yl group, 2-phenylpyridin-4-yl group, and 3-phenylpyridin-4-yl group, and the like.

R ¹ , R ² , R ³ and R ⁴ each independently represent an alkyl group having 1 to 18 carbon atoms, or 1 It is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted with an alkyl group having 6 to 6, a phenyl group, a pyridyl group or a cyano group, an alkyl group having 1 to 18 carbon atoms, or It is more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group of 1 to 6 or a cyano group. R ¹ , R ² , R ³ and R ⁴ are each independently an alkyl group having 1 to 6 carbon atoms or a C 6 to 18 and R ¹ , R ² , R ³ and R ⁴ are each independently a methyl group or a C 6 More preferably, it is an aromatic hydrocarbon group of .about.12.

[About L]
L represents a divalent aromatic hydrocarbon group consisting only of 6-membered rings or a divalent nitrogen-containing aromatic group consisting only of 6-membered rings. p represents 0, 1, or 2; When p is 2, L may be the same or different.

Examples of L include orthophenylene, metaphenylene, paraphenylene, 2,3-pyridylene, 2,4-pyridylene, 2,5-pyridylene, 2,6-pyridylene, 3,4- pyridylene group, 3,5-pyridylene group, 3,5-pyridylene group, 3,5-pyridylene group, 2,3-pyrazylene group, 2,5-pyrazylene group, 2,6-pyrazylene group, 2,4-pyrimidylene 2,4-pyrimidylene, 2,5-pyrimidylene, 4,5-pyrimidylene, 4,6-pyrimidylene and 2,4-triazylene radicals.

L is preferably a phenylene group or a pyridylene group because the alkyltriazine compound (1) has good properties as a material for an organic electroluminescence device. More preferably, it is a divalent aromatic hydrocarbon group composed only of 6-membered rings, such as a phenylene group.

p is 0, 1 or 2, preferably 0 or 1, more preferably 0, in that the alkyltriazine compound (1) has an appropriate glass transition temperature.

[About q]
q represents the number of phenylene groups and is 0, 1 or 2; q is preferably 0 or 1 in that the alkyltriazine compound (1) has an appropriate glass transition point.

[About ^R5 ]
R ⁵ is a hydrogen atom; an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted by an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; an alkyl group having 1 to 18 carbon atoms; a heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring optionally substituted with a group, a phenyl group, a pyridyl group or a cyano group; or a silyl group represented by Si(Ar) ₃ ; . Each Ar independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms. Examples of Ar include phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthranyl, fluoranthenyl, pyrenyl, triphenylenyl, and chrysenyl groups.

Examples of R ⁵ include hydrogen atom, phenyl group, 1-naphthyl group, 2-naphthyl group, 9-anthranyl group, 9-phenanthrenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4 -yl group, (3'-cyano)biphenyl-2-yl group, (3'-cyano)biphenyl-3-yl group, (3'-cyano)biphenyl-4-yl group, (3'-cyano)biphenyl -2-yl group, (4′-cyano)biphenyl-3-yl group, (4′-cyano)biphenyl-4-yl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3,5-dimethylphenyl group, 2-(1-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 4-(1-naphthyl)phenyl group, 2-(2-naphthyl)phenyl group, 3- (2-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,5-dicyanophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,5-dicyanophenyl group, (3'-cyano) biphenyl-2-yl group, (3'-cyano) biphenyl-3-yl group, (3'- Cyano)biphenyl-4-yl group, (3′-cyano)biphenyl-2-yl group, (4′-cyano)biphenyl-3-yl group, (4′-cyano)biphenyl-4-yl group, (10 -methyl)-9-phenanthrenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 5-methyl-2-pyrimidyl group, 5- cyano-2-pyrimidyl group, (4,6-dimethyl)-2-pyrimidyl group, (4,6-dicyano)-2-pyrimidyl group, 2-pyrazyl group, 3,5-dimethyl-2-pyrazyl group, 3 - pyridazyl group, 4-pyridazyl group, 2-methylpyridin-2-yl group, 3-methylpyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 2 -methylpyridin-3-yl group, 4-methylpyridin-3-yl group, 5-methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 3 -methylpyridin-4-yl group, 2,6-dimethylpyridin-3-yl group, 2,4-dimethylpyridin-3-yl group, 2,5-dimethylpyridin-3-yl group, 2-cyanopyridine- 2-yl group, 3-cyanopyridin-2-yl group, 4-cyanopyridin-2-yl group, 5-cyanopyridin-2-yl group, 2-cyanopyridin-3-yl group, 4-cyanopyridin- 3-yl group, 5-cyanopyridin-3-yl group, 6-cyanopyridin-3-yl group, 2-cyanopyridin-4-yl group, 3-cyanopyridin-4-yl group, 2-quinolinyl group, to mention 4-quinolinyl, 8-quinolinyl, 2-quinoxalinyl, 9-phenanthrolinyl, triphenylsilyl, tris(1-naphthyl)silyl, and tris(2-naphthyl)silyl; can be done.

Since the alkyltriazine compound (1) has good characteristics as a material for an organic electroluminescent device, R ⁵ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group, and is substituted with a cyano group. It is preferably a heteroaromatic group having 4 to 17 carbon atoms composed only of a 6-membered ring which may be optionally substituted, or a silyl group represented by Si(Ar) ₃ , which may be substituted with a cyano group more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 11 carbon atoms consisting only of a 6-membered ring optionally substituted with a cyano group, or a triphenylsilyl group; preferable. ^R5 is more preferably a phenyl group, a biphenylyl group, a phenanthrenyl group, a pyridyl group, or a triphenylsilyl group in terms of ease of synthesis of the alkyltriazine compound (1).

[Specific examples of alkyltriazine compound (1)]
Specific examples of the alkyltriazine compound (1) include (A-1) to (A-8) and (B-1) to (B-165) below, but the present invention is not limited thereto. not something.

A compound represented by (A-1), (A-3) or (A-8) is preferable as the alkyltriazine compound (1) in terms of good performance as an electron transport material in an organic electroluminescent device.

<Synthesis of alkyltriazine compound (1)>
Next, a method for producing the alkyltriazine compound (1) will be described.

Alkyltriazine compound (1) can be produced by the method shown in Synthetic Route 1 or Synthetic Route 2 below. Compound (1a) contained in alkyltriazine compound (1) (hereinafter sometimes referred to as alkyltriazine compound (1a)) can be produced by the method shown in Synthetic Route 3.

In formulas (1a), (3), (3b), (4), and (5),
The definitions of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L, p and q are respectively R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L, p and is the same as the definition of q;
Y ¹ and Y ² each independently represent a halogen atom or a trifluoromethanesulfonyloxy group;
R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group;
two OR ⁶ groups, OR ⁷ groups or OR ⁸ groups that are bonded to one boron atom may be the same or different;
Two OR ⁶ groups, OR ⁷ groups, or OR ⁸ groups bonded to one boron atom and the bonded boron atom may be combined to form a ring.

The halogen atoms represented by Y ¹ and Y ² can be exemplified by fluorine, chlorine, bromine and iodine atoms. A chlorine or bromine atom is preferred.

Examples of the OR ⁶ group, OR ⁷ group, or OR ⁸ group that bonds to the boron atom include OH, OMe, O ⁱ Pr, OBu, and OPh. Me is a methyl group, ⁱ Pr is an isopropyl group, Bu is a butyl group, and Ph is a phenyl group.

B ⁽ OR ⁶ ) _{2 , B(OR 7 ) 2} ^{, or} _B ⁽ OR ⁸ ) As examples of ₂ , the following groups (I) to (VIII) can be exemplified, and the group (II) is preferable from the viewpoint of good yield.

Coupling reactions in synthetic pathways 1 to 3 are performed by combining a triazine compound represented by formula (2) or (4) and a boron compound represented by formula (3), (3b) or (5) with a palladium catalyst and It is a method of reacting in the presence of a base, and the method disclosed in JP-A-2011-063584 or general Suzuki-Miyaura reaction conditions can be applied.

Boron compound (3), (3b) or (5) is, for example, JP-A-2011-063584, JP-A-2017-141216, WO2015114102 or The Journal of Organic Chemistry, 60, 7508, 1995 It can be produced according to the method disclosed in 2003.

Triazine compound (2) or (4) is described in reference examples or prior art documents, for example, JP-A-2018-030792, Synthesis, Vol. 10, 841, 1980 or The Journal of Organic Chemistry, Vol. 30, p. , 1965. Moreover, you may use a commercial item. The triazine compound is preferably used in an amount of 0.5 to 3.0 molar equivalents relative to the boron compound in terms of good reaction yield.

Palladium catalysts used in the coupling reactions in Synthetic Routes 1 to 3 include, for example, palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. Additionally, complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonato, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, and dichlorobis(benzonitrile)palladium; , dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine) ) palladium and palladium complexes having tertiary phosphines as ligands, such as dichlorobis(tricyclohexylphosphine)palladium. These can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or 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, and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl.

Among them, a palladium complex having a tertiary phosphine as a ligand is preferable in that the yield is good, and triphenylphosphine, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, or tricyclohexyl A palladium complex having phosphine as a ligand is more preferred.

The molar ratio of the tertiary phosphine and the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, more preferably in the range of 1:2 to 3:1 in terms of good yield. preferable. The amount of the palladium catalyst used in the coupling reaction in Synthetic Routes 1 to 3 is not limited, but the molar equivalent of the palladium catalyst is in the range of 0.005 to 0.5 molar equivalents relative to the boron compound in terms of good yield. preferably in

Examples of the base used in the coupling reaction in Synthetic Routes 1 to 3 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. carbonates; metal acetates such as potassium acetate and sodium acetate; metal phosphates such as potassium phosphate and sodium phosphate; metal fluoride salts such as sodium fluoride, potassium fluoride and cesium fluoride; and sodium methoxy metal alkoxides such as potassium methoxide, sodium ethoxide, potassium isopropyl oxide, and potassium tert-butoxide; Among them, metal carbonates or metal phosphates are preferable, and potassium carbonate or sodium carbonate is more preferable, because of good reaction yield. There are no particular restrictions on the amount of base used. The molar ratio of the base to the boron compound is preferably in the range of 1:2 to 10:1, more preferably in the range of 1:1 to 4:1, in terms of good reaction yield.

The coupling reactions in synthetic routes 1-3 can be carried out in a solvent. Solvents include water; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; benzene, toluene, xylene, mesitylene, and aromatic hydrocarbons such as tetralin; carbonate esters 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, esters such as methyl butyrate, and γ-lactone; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); N,N,N',N'-tetra ureas such as methyl urea (TMU) and N,N'-dimethylpropylene urea (DMPU); dimethyl sulfoxide (DMSO); and methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, alcohols such as diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; These may be used alone, or may be used by mixing at any ratio. There are no particular restrictions on the amount of solvent used. Among these, water, ether, amide, alcohol, or a mixed solvent thereof is preferred in that the reaction yield is good, and a mixed solvent of THF and water is more preferred.

The coupling reaction in Synthetic Routes 1 to 3 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. preferably implemented.

Alkyltriazine compound (1) and ( 1a) can be obtained.

<Materials for Organic Electroluminescent Devices>
A material for an organic electroluminescence device according to one aspect of the present disclosure contains the alkyltriazine compound (1) described above. The material for an organic electroluminescence device may be composed of only the alkyltriazine compound (1) described above, or may contain a dopant in addition to the alkyltriazine compound (1), as long as the desired characteristics and performance are exhibited. may further contain other components.

<Electron transport material for organic electroluminescence device>
An electron-transporting material for an organic electroluminescent device according to one aspect of the present disclosure contains the alkyltriazine compound (1) described above. The electron-transporting material for an organic electroluminescence device may be composed only of the alkyltriazine compound (1) described above, or may contain a dopant in addition to the alkyltriazine compound (1), as long as desired properties and performance are exhibited It may further contain other ingredients such as

<Organic electroluminescent element>
An organic electroluminescent device (hereinafter sometimes simply referred to as an organic electroluminescent device) according to one aspect of the present disclosure, including the alkyltriazine compound (1), will be described below.

An organic electroluminescent device according to one aspect of the present disclosure contains an alkyltriazine compound (1). In the organic electroluminescent device according to the embodiment of the present invention, the alkyltriazine compound (1) is contained in the organic electroluminescent device in a state in which the above-described organic electroluminescent device material or organic electroluminescent device electron-transporting material is applied. be.

The configuration of the organic electroluminescent device is not particularly limited, but includes, for example, configurations (i) to (v) shown below.
(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 alkyltriazine compound (1) may be contained in any of the above layers, but from the viewpoint of excellent luminescent properties of the organic electroluminescent device, the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode. It is preferably contained in one or more selected layers. Therefore, in the case of the structures shown in (i) to (v) above, the alkyltriazine compound (1) may be contained in one or more layers selected from the group consisting of the light-emitting layer, the electron-transporting layer and the electron-injecting layer. preferable.

Hereinafter, the organic electroluminescence device according to one aspect of the present disclosure will be described in more detail with reference to FIG. 1, taking the configuration (v) above as an example.

The organic electroluminescent device shown in FIG. 1 has a so-called bottom emission type device configuration, but the organic electroluminescent device according to one aspect of the present disclosure is not limited to the bottom emission type device configuration. do not have. That is, the organic electroluminescent device according to one aspect of the present disclosure may have other known device configurations such as top emission type.

FIG. 1 is a schematic cross-sectional view showing an example of a laminate structure of an organic electroluminescence device containing an alkyltriazine compound (1) according to one aspect of the present disclosure. FIG. 2 is a schematic cross-sectional view showing another example of a laminated structure of an organic electroluminescence device containing the alkyltriazine compound (1) according to one aspect 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 conversely, other layers may be added. For example, a hole-blocking layer 9 may be provided between the light-emitting layer 5 and the electron-transporting layer 6, as shown in FIG. Alternatively, hole injection layer 3 may be omitted and hole transport layer 4 may be provided directly on anode 2 . Further, a single layer having the functions of a plurality of layers, such as an electron injection/transport layer having both the function of an electron injection layer and the function of an electron transport layer in a single layer. It may be a configuration provided instead of. Further, for example, each of the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may be composed of a plurality of layers. For example, as shown in FIG. 2, instead of the single-layer hole transport layer 4, a first hole transport layer 41 and a second hole transport layer 42 are stacked in this order from the hole injection layer 3 side. It may be provided as follows.

[Layer containing alkyltriazine compound (1)]
In the structural example shown in FIG. 1, the organic electroluminescence device 100 contains the alkyltriazine 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 . In particular, the electron transport layer 6 preferably contains the alkyltriazine compound (1). In addition, the alkyltriazine compound (1) may be contained in a plurality of layers included in the organic electroluminescent device.

In addition, the organic electroluminescence device 100 in which the electron transport layer 6 contains the alkyltriazine compound (1) will be described below.

[Substrate 1]
The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, a plastic plate and the like.

Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, and a plastic film. Among these, a glass plate, a quartz plate, and a transparent plastic film are preferable.

Examples of light-transmitting plastic films include 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 addition, in the case of the configuration in which light emission 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 hole injection layer 3 side).

Materials for 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 materials for the anode include metals such as Au; conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ and ZnO.

For organic electroluminescent devices in which emitted light is extracted through the anode, the anode is formed of a conductive transparent material that passes or substantially passes the emitted light.

[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 to be described later.

The hole-injecting layer and the hole-transporting layer have a function of transferring holes injected from the anode to the light-emitting layer, and the hole-injecting layer and the hole-transporting layer are interposed between the anode and the light-emitting layer. causes more holes to be injected into the light-emitting layer at lower electric fields.

Moreover, the hole injection layer and the hole transport layer also function as electron blocking layers. That is, 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 present at the interface between the light-emitting layer and the hole injection layer and/or the hole transport layer. , 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 an effect such as an improvement in light-emitting efficiency, and an organic electroluminescence device having excellent light-emitting performance can be obtained.

Materials for the hole injection layer and the hole transport layer have at least one of hole injection properties, hole transport properties, and electron blocking properties. Materials 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, and amino-substituted chalcone. derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styryl Examples include amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, from the viewpoint of good performance of the organic electroluminescent device.

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-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), and 4,4′,4″-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA).

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

The hole injection layer and the hole transport layer may have a single structure composed of one or more materials, or may have a laminated structure composed of multiple layers having the same composition or different compositions.

[Light emitting layer 5]
A light-emitting layer 5 is provided between the hole-transporting layer 4 and an electron-transporting layer 6, which will be described later.

Materials for the light-emitting layer include phosphorescent light-emitting materials, fluorescent light-emitting materials, and thermally activated delayed fluorescent light-emitting materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

The emissive 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 dopants and can have any color.

Host materials include, for example, compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or 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.

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, and indenoperylenes. 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 dopants 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](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.

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

The light-emitting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of multiple 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 which will be described later.

The electron transport layer has a function of transmitting electrons injected from the cathode to the light emitting layer. By interposing an electron-transporting 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 alkyltriazine compound (1). The electron transport layer may further contain one or more selected from conventionally known electron transport materials in addition to the alkyltriazine compound (1).

When the triazine compound (1) is not contained in the electron-transporting layer but is contained in another layer, one or more selected from conventionally known electron-transporting materials may be used as the electron-transporting material constituting the electron-transporting layer. can be done.

Conventionally known electron-transporting materials include alkali metal complexes, alkaline earth metal complexes, earth metal complexes, and the like. Alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinatolithium (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]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinate)(o -cresolato)gallium, bis(2-methyl-8-quinolinato)-1-naphtholatoaluminum, and bis(2-methyl-8-quinolinato)-2-naphtholatogallium.

The electron-transporting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of multiple layers having the same composition or different compositions.

In the organic electroluminescent device according to this aspect, an electron injection layer may be provided for the purpose of improving electron injection properties and device characteristics (e.g., luminous efficiency, low driving voltage, 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 an electron injection layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

Materials for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, and anthrone. organic compounds. Materials for the electron injection layer include SiO ₂ , AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C. Inorganic compounds such as oxynitrides are also included.

[Cathode 8]
A cathode 8 is provided on the electron injection layer 7 .

In the case of an organic electroluminescence device configured so that only light emitted through the anode is taken out, the cathode can be made of any conductive material.

Materials for the cathode include, for example, metals with a small work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, a metal with a small work function is, for example, a metal 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, and rare earth metals.

Among them, from the viewpoint of electron injection properties and durability against oxidation, etc., a mixture of an electron injection metal and a second metal that has a higher work function and is more stable, such as a magnesium/silver mixture, magnesium /aluminum mixtures, magnesium/ _indium mixtures, aluminum/aluminum oxide ( _Al2O3 ) mixtures, or lithium/aluminum mixtures are preferred.

[Hole blocking layer 9]
As mentioned above, a hole blocking layer 9 may be provided between the light emitting layer 5 and the electron transport layer 6 . The hole-blocking layer has the function of preventing holes or excitons from entering the electron-transporting layer from the light-emitting layer. Materials for the hole-blocking layer include triazine compounds represented by formula (1) in JP-A-2021-145126 and triazine compounds described in JP-A-2018-507174.

[Method of Forming Each Layer]
Each layer except for the electrodes (anode, cathode) described above is formed by thinning by a known method such as vacuum deposition, spin coating, casting, and LB (Langmuir-Blodgett method). can do. The material for each layer may be used alone, or if necessary, it may be used together with a material such as a binder resin and a solvent.

The thickness of each layer thus formed is not particularly limited and can be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 μm.

The anode and cathode can be formed by thinning the electrode material by methods such as vapor deposition and sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or a pattern of 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 cathode is preferably 1 μm or less, more preferably 10 nm or more and 200 nm or less.

Incidentally, the layer containing the triazine compound (1) may be formed in combination with the conventionally known electron-transporting material. Therefore, for example, the alkyltriazine 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 the layer of the alkyltriazine compound (1). good.

The organic electroluminescence element may be used as a kind of lamp for illumination or as a light source for exposure, a type of projection device for projecting an image onto a screen or the like, or a type of display for directly viewing still images or moving images. You may use it as a device (display). When the organic electroluminescence element is used as a display device for reproducing moving images, the drive system may be a simple matrix (passive matrix) system or an active matrix system. Further, by using two or more kinds of organic electroluminescent elements having different emission colors, it is possible to produce a full-color display device.

Alkyltriazine compound (1) can provide an organic electroluminescence device which, when used as an electron-transporting layer, exhibits remarkably superior luminous efficiency and long-life characteristics compared to conventionally known triazine compounds. Furthermore, the alkyltriazine compound (1) has high electron mobility and high carrier transport properties due to its planar skeleton. Therefore, it is possible to obtain effects such as a decrease in driving voltage of the organic electroluminescence device, an improvement in luminous efficiency, and a longer life of the device.

Alkyltriazine compound (1) can be used as an electron transport layer of an organic electroluminescent device to provide a triazine compound that can achieve all of low drive voltage, high efficiency and long life of the device at a high level. can. Further, it is possible to provide an organic electroluminescence device using the alkyltriazine compound (1) that can exhibit low driving voltage, high efficiency and long life.

With such a configuration, it is possible to provide an organic electroluminescence device that further exhibits high luminous efficiency and long life characteristics. This is expected to contribute to the development of image display technology with even higher definition and longer life. Therefore, according to the embodiment of the present invention, from the viewpoint of improving the accuracy of information transmission and reducing the burden on the environment due to waste, etc., it is possible to improve motivation to work, develop industry, and sustainably contribute to environmental conservation. It is expected to contribute to the achievement of development goals (SDGs).

The present invention is not limited to the above-described embodiments, but can be modified in various ways within the scope of the claims, and can be obtained by appropriately combining technical means disclosed in different embodiments. is also included in the technical scope of the present invention.

EXAMPLES The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited by these examples.

[ ¹ H-NMR measurement]
Bruker ASCEND HD (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. Commercially available reagents were used.

[Emission characteristic measurement]
The luminous properties of the organic electroluminescent device were evaluated using a brightness meter BM-9 (manufactured by Topcon Technohouse Co., Ltd.) by applying a direct current to the device prepared in each example (described later) in an environment of 25°C.

[Synthesis of compound]
Synthetic Example-1
4,6-diphenyl-2-[3-(9-phenanthrenyl)-5-[(4,6-dimethyl)-1,3,5-triazin-2-yl]phenyl-1,3,5-triazine

Under an argon atmosphere, 4,6-diphenyl-2-[3-(9-phenanthrenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- 1,3,5-triazine (15.3 g, 24.3 mmol), 2-chloro-4,6-dimethyl-1,3,5-triazine (3.00 g, 20.1 mmol), tetrakis(triphenylphosphine) Palladium (1.40 g, 1.21 mmol), was suspended in THF (240 mL). After adding 2.0 M aqueous potassium carbonate solution (37.0 mL) to this suspension, the mixture was heated under reflux for 24 hours. After allowing to cool, water and methanol were added to the reaction mixture. The resulting solid was collected by filtration and washed with silica gel column chromatography (chloroform) and toluene to give the desired 4,6-diphenyl-2-[3-(9-phenanthrenyl)-5-[(4,6- Dimethyl)-1,3,5-triazin-2-yl]-phenyl-1,3,5-triazine (A-1) was obtained (3.47 g, 5.85 mmol, 29%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.76 (s, 6H), 7.54-7.64 (m, 7H), 7.67 (ddd, J = 7.9, 6.9 , 1.1 Hz, 1 H), 7.73 (dddd, J = 8.2, 7.1, 3.1, 1.3 Hz, 1 H), 7.88 (s, 1 H), 7.94 (dd, J = 8.2, 0.8Hz, 1H).7.98 (dd, J = 7.7, 1.2Hz, 1H), 8.78-8.82 (m, 5H), 8.85 (d , J = 8.2 Hz, 1H), 8.94 (dd, J = 1.7, 1.7 Hz, 2H), 9.11 (dd, J = 1.7, 1.7 Hz, 1H) 9.94 (dd, J=1.7, 1.6Hz, 1H).

Synthesis example-2
2,4-diphenyl-6-[3-(6-methyl-4-phenyl-1,3,5-triazin-2-yl)-5-(9-phenanthrenyl)-phenyl]-1,3,5- Triazine

4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(9-phenanthrenyl)-phenyl] under argon atmosphere 1,3,5-triazine (4.00 g, 6.50 mmol), 2-chloro-6-methyl-4-phenyl-1,3,5-triazine (2.10 g, 7.80 mmol), tetrakis(triphenyl Phosphine)palladium (400 mg, 0.344 mmol) was suspended in THF (80 mL). A 2M aqueous sodium carbonate solution (10.0 mL) was added thereto, and the mixture was heated under reflux at 80° C. for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and recrystallized with toluene to give the target 2,4-diphenyl-6-[3-(6-methyl-4-phenyl-1,3,5-triazin-2-yl) -5-(9-phenanthrenyl)-phenyl]-1,3,5-triazine (A-2) was obtained (1.46 g, 2.24 mmol, 35%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.86 (s, 3H), 7.52-7.73 (m, 13H), 7.91 (s, 1H), 7.96 (dd, J = 8.2, 0.9Hz, 1H), 8.00 (dd, J = 8.2, 0.9Hz, 1H) 8.73 (ddd, J = 7.1, 1.6, 1.3Hz , 2H), 8.79-8.88 (m, 6H), 9.04 (t, J = 1.7Hz, 1H), 9.13 (t, J = 1.7Hz, 1H), 10.16 (t, J=1.7 Hz, 1 H).

Synthetic Example-3
2,4-diphenyl-6-[5-(6-methyl-4-phenyl-1,3,5-triazin-2-yl)-1,1′:2′,1″-terphenyl-3- yl]-1,3,5-triazine

4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′:2′,1′ under argon atmosphere '-terphenyl-5-yl]-1,3,5-triazine (5.00 g, 8.52 mmol), 2-chloro-6-methyl-4-phenyl-1,3,5-triazine (2.47 g , 9.46 mmol), tetrakis(triphenylphosphine)palladium (500 mg, 0.43 mmol) was suspended in THF (80 mL). After adding 2M aqueous sodium carbonate solution (13.0 mL) to this suspension, the mixture was heated under reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and recrystallized with toluene to give the target 2,4-diphenyl-6-[5-(6-methyl-4-phenyl-1,3,5-triazin-2-yl) -1,1′:2′,1″-terphenyl-3-yl]-1,3,5-triazine (A-3) was obtained. (3.89g, 6.22mmol, 72%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.83 (s, 3H), 7.11 (tt, J = 6.6, 1.2 Hz, 1H), 7.23 (tt, J = 8 .0, 1.5 Hz, 2H), 7.30-7.35 (m, 2H), 7.51-7.67 (m, 12H), 7.71 (dd, J = 2.4, 1. 8Hz, 1H), 8.67 (dd, J = 6.7, 1.7Hz, 2H), 8.73-8.79 (m, 6H), 9.85 (dd, J = 1.8, 1 .6Hz, 1H).

Synthetic Example-4
6,6′-{5-(triphenylsilyl)phenyl-1,3-yl)-bis(2-methyl-4-phenyl-1,3,5-triazine)

2-chloro-4-phenyl-6-methyl-1,3,5-triazine (2.20 g, 3.74 mmol), (5-triphenylsilyl-1,3-phenylene) diboronic acid pinacol ester under argon atmosphere (1.70 g, 8.09 mmol), dichlorobistriphenylphosphino)palladium (78 mg, 0.11 mmol), 2M potassium carbonate aqueous solution (12.0 mL, 24 mmol) and THF (18 mL) were added, and the mixture was heated under reflux for 22 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid is collected by filtration and recrystallized with toluene to give 2,2′-(5-triphenylsilyl-1,3-phenylene)bis(4-methyl-6-phenyl-1,3,5- triazine) (A-4) was obtained (yield 1.21 g, yield 49%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.81 (s, 6H), 7.60 (brt, J=7.3Hz, 2H), 7.44-7.55 (m, 13H), 7.72 (m, 6H), 8.55 (m, 4H), 9.14 (d, J=1.7Hz, 2H), 9.82 (t, J=1.7Hz, 1H).

Synthetic Example-5
2,4-diphenyl-6-{5-[6-methyl-4-(4-biphenylyl)-1,3,5-triazin-2-yl]-1,1′:2′,1″-tel Phenyl-3-yl}-1,3,5-triazine

4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′:2′,1′ under argon atmosphere '-Terphenyl-5-yl]-1,3,5-triazine (760 mg, 1.14 mmol), 2-chloro-6-methyl-4-(4-biphenylyl)-1,3,5-triazine (260 mg , 0.96 mmol), tetrakis(triphenylphosphine)palladium (60 mg, 0.05 mmol) was suspended in THF (10 mL). After adding 2M aqueous sodium carbonate solution (1.5 mL) to this suspension, the mixture was heated under reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and purified by silica gel column chromatography (hexane/chloroform) to give the desired 2,4-diphenyl-6-{5-[6-methyl-4-(4-biphenylyl)-1 ,3,5-triazin-2-yl]-1,1′:2′,1″-terphenyl-3-yl}-1,3,5-triazine (A-5). (309mg, 0.43mmol, 43%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.85 (s, 3H), 7.13 (tt, J = 7.2, 1.3 Hz, 1H), 7.23-7.27 (m , 3H), 7.34 (ddd, J = 7.8, 1.5, 0.9Hz, 2H), 7.43 (td, J = 6.9, 1.1Hz, 1H), 7.48- 7.66 (m, 9H), 7.72 (m, 4H), 7.80 (dd, J=8.2, 1.5Hz, 2H), 8.73-8.79 (m, 8H), 9.84 (dd, J=1.7, 1.6 Hz, 1 H).

Synthetic Example-6
2-[5′-(4,6-diphenyl-1,3,5-triazin-2-yl)-(1,1′:3′,1″-terphenyl)-4-yl]-4- Methyl-6-phenyl-1,3,5-triazine

Under an argon atmosphere, 2,4-diphenyl-6-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-(1,1′-biphenylyl)-3 -yl]-1,3,5-triazine (3.10 g, 6.05 mmol), 2-(4-chlorophenyl)-4-methyl-6-phenyl-1,3,5-triazine (1.88 g, 6 .68 mmol), palladium acetate (68 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (291 mg, 0.61 mmol) were suspended in THF (60 mL). . A 2M potassium carbonate aqueous solution (10 mL, 20 mmol) was added to this suspension, and the mixture was stirred at 80° C. for 22 hours. After allowing to cool to room temperature, water, methanol and hexane were added, and the precipitate was collected by filtration. The filtered product was suspended in xylene (400 mL), heated to 140° C., added with activated charcoal, stirred, and then filtered through celite. After cooling to room temperature, the precipitate was collected by filtration and recrystallized from xylene (300 mL) to give 2-[5′-(4,6-diphenyl-1,3,5-triazin-2-yl )-(1,1′:3′,1″-terphenyl)-4-yl]-4-methyl-6-phenyl-1,3,5-triazine (A-6) was obtained (2. 64 g, 69% yield).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.83 (s, 3H), 7.50-7.45 (m, 1H), 7.67-7.55 (m, 11H), 7. 84 (brd, J=7.0Hz, 2H), 7.99 (brd, J=8.5Hz, 2H), 8.13 (dd, J=1.8, 1.7Hz, 1H), 8.69 (brd, J = 6.6 Hz, 2H), 8.83 (brd, J = 7.1 Hz, 6H), 9.03 (dd, J = 1.6, 1.6 Hz, 1H), 9.07 ( dd, J=1.1.6, 1.6 Hz, 1H).

Synthetic Example-7
2-[3′-(4,6-diphenyl-1,3,5-triazin-2-yl)-5′-(pyridin-3-yl)-[1,1′-biphenylyl]-4-yl] -4-methyl-6-phenylyl-1,3,5-triazine

2,4-diphenyl-6-[3-(pyridin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) under argon atmosphere -phenyl]-1,3,5-triazine (123 mg, 0.24 mmol), 2-(4-chlorophenyl)-4-methyl-6-phenyl-1,3,5-triazine (74 mg, 0.26 mmol), Palladium acetate (3.3 mg, 15 μmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (13 mg, 27 μmol) were suspended in THF (2.5 mL). A 2M potassium carbonate aqueous solution (0.5 mL, 1.0 mmol) was added to this suspension, and the mixture was stirred at 80° C. for 23 hours. After allowing to cool to room temperature, water, methanol and hexane were added, and the precipitate was collected by filtration. The filtered product was suspended in toluene (30 mL), heated to 110° C., added with activated charcoal, stirred, and then filtered through celite. Low-boiling components were distilled off, the precipitate was collected by filtration, and then recrystallized from toluene (20 mL) to give 2-[3'-(4,6-diphenyl-1,3,5-triazine-2- yl)-5′-(pyridin-3-yl)-[1,1′-biphenylyl]-4-yl]-4-methyl-6-phenylyl-1,3,5-triazine (A-7) (32 mg, 21% yield).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.84 (s, 3H), 7.68-7.49 (m, 10H), 9.13 (dd, J = 1.6, 1.4Hz , 1H), 9.11 (d, J = 2.0Hz, 1H), 7.99 (d, J = 8.4Hz, 2H), 8.14-8.11 (m, 2H), 8.69 (brd, J = 8.4Hz, 2H), 8.72 (dd, J = 4.8, 1.5Hz, 1H), 8.85-8.81 (m, 6H), 9.04 (dd, J=1.5, 1.4Hz, 1H).

Synthetic Example-8
2,4-diphenyl-6-{4-(4,6-dimethyl-1,3,5-triazin-2-yl)-1,1′:3′,1″:2″,1″ '-quaterphenyl-5'-yl}-1,3,5-triazine

4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′:2′,1′ under argon atmosphere '-terphenyl-5-yl]-1,3,5-triazine (4.10 g, 7.12 mmol), 4,6-dimethyl-2-(4-chlorophenyl)-1,3,5-triazine (1 .62 g, 7.46 mmol), palladium acetate (80 mg, 0.35 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (251 mg, 7.0 mmol) in THF (70 mL). Suspended. After adding 2M aqueous sodium carbonate solution (11 mL) to this suspension, the mixture was heated under reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and purified by silica gel column chromatography (hexane/chloroform) to give the desired 2,4-diphenyl-6-{4-(4,6-dimethyl-1,3,5-triazyl -2-yl)-1,1′:3′,1″:2″,1′″-quaterphenyl-5′-yl}-1,3,5-triazine (A-8) Obtained. (3.66 g, 5.71 mmol, 80%).
¹ H-NMR (CDCl ₃ ) δ (ppm): 2.72 (s, 6H), 7.23-7.32 (m, 5H), 7.50-7.66 (m, 12H), 7. 71 (dd, J = 7.8, 1.8Hz, 1H), 8.56 (ddd, J = 8.5, 1.8, 1.7Hz, 2H), 8.73-8.79 (m, 5H), 8.89 (dd, J=1.7, 1.6 Hz, 1H).

Reference example-1
2-chloro-4-methyl-6-(4-biphenylyl)-1,3,5-triazine

Under an argon atmosphere, 2,4-dichloro-6-(4-biphenylyl)-1,3,5-triazine (300 mg, 1 mmol) was suspended in toluene (2 mL) and cooled to 0°C. To this suspension, 3M-methylmagnesium chloride THF solution (0.5 mL) was added over 3 minutes, and the mixture was stirred at room temperature for 6 hours. 500 μL of 1 M-hydrochloric acid was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. After sodium sulfate was added to the reaction mixture to dry it, the solid component was removed by filtration. After the solvent was distilled off from the filtrate under reduced pressure, the residue was washed with methanol to obtain the target 2,4-dichloro-6-(4-biphenylyl)-1,3,5-triazine (purity 85%). v (261 mg).
¹ H-NMR (CDCl ₃ ) δ 2.73 (s, 3H), 7.35 (tt, J = 7.6, 1.2 Hz, 1H), 7.41 (ddd, J = 7.6, 7. 4, 1.2Hz, 2H), 7.61 (J = 7.6, 1.4, 1.2Hz, 2H), 7.68 (dd, J = 7.4, 1.3Hz, 2H), 8 .51 (ddd, J=7.6, 1.6, 1.3 Hz, 2H).

[Organic electroluminescence device examples]
Device example-1 (see Fig. 2)
(Preparation of substrate 1 and anode 2)
As a substrate 1 having an anode 2 on its surface, a glass substrate with an ITO transparent electrode, in which an indium-tin oxide (ITO) film (thickness: 110 nm) with a width of 2 mm was patterned in stripes, was prepared. Then, after washing the substrate with isopropyl alcohol, the surface was treated by ozone ultraviolet washing.

(Preparation for vacuum deposition)
Each layer was vacuum-deposited on the surface-treated substrate after cleaning by a vacuum deposition method to laminate each layer.

First, the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa. Then, each layer was produced 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 deposited at a ratio of 99:1 (mass ratio) to form a 10 nm film, A hole injection layer 3 was produced. The deposition 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 deposited at a rate of 0.2 nm/sec to a thickness of 85 nm 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 deposited at a rate of 0.15 nm/sec to form a 5 nm film. , a second hole transport layer 42 was produced.

(Preparation of light-emitting layer 5)
3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9′-spirofluorene purified by sublimation and were deposited at a ratio of 95:5 (mass ratio) to a thickness of 20 nm to prepare a light-emitting layer 5 . The deposition rate was 0.1 nm/sec.

(Preparation of hole blocking layer 9)
Sublimation of purified 2-{3′-(9,9-dimethylfluoren-2-yl)-biphenylyl-3-yl}-4,6-diphenyl-1,3,5-triazine at a rate of 0.05 nm/s A hole blocking layer 9 was formed by forming a film with a thickness of 6 nm.

(Preparation of electron transport layer 6)
Sublimation purified 4,6-diphenyl-2-[3-(9-phenanthrenyl)-5-[(4,6-dimethyl)-1,3,5-triazin-2-yl]-phenyl-1,3, 5-triazine (A-1) and 8-hydroxyquinolinolatolithium (hereinafter referred to as Liq) were deposited at a ratio of 50:50 (mass ratio) to a thickness of 25 nm to prepare an electron transport layer 6 . The deposition rate was 0.15 nm/sec.

(Preparation of electron injection layer 7)
An electron injection layer 7 was produced by depositing Liq to a thickness of 1 nm at a rate of 0.02 nm/sec.

(Preparation of cathode 8)
Finally, a metal mask was placed perpendicular to the ITO stripes (anode 2) on the substrate 1, and a cathode 8 was formed. The cathode was formed by depositing silver/magnesium (mass ratio 1/10) and silver in this order to 80 nm and 20 nm, respectively, to form a two-layer structure. The deposition rate of silver/magnesium was 0.5 nm/second, and the deposition rate of silver was 0.2 nm/second.

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

Furthermore, this device was sealed in a nitrogen atmosphere glove box with an oxygen and water concentration of 1 ppm or less. Sealing was performed by using a bisphenol F-type epoxy resin (manufactured by Nagase ChemteX Corporation) between the glass sealing cap and the film formation substrate (element).

Device example-2
In Device Example-1, sublimation-refined 2,4-diphenyl-6-[5-(6-methyl-4-phenyl-1,3,5 -triazin-2-yl)-1,1′:2′,1″-terphenyl-3-yl]-1,3,5-triazine (A-3) and Liq at 50:50 (mass ratio) An organic electroluminescence device was produced in the same manner as in Device Example-1, except that a film of 25 nm was formed at a rate of 0.15 nm/sec.

Device Example-3
Sublimation-refined 2,4-diphenyl-6-{4-(4,6-dimethyl-1,3,5-triazyl) was used in the electron-transporting layer 6 in Device Example-1 instead of the compound (A-1). -2-yl)-1,1′:3′,1″:2″,1′″-quaterphenyl-5′-yl}-1,3,5-triazine (A-8) and An organic electroluminescence device was produced in the same manner as in Device Example-1, except that Liq was deposited at a ratio of 50:50 (mass ratio) to a thickness of 25 nm (deposition rate: 0.15 nm/sec).

Device Example-4
In Device Example-1, sublimation-refined 2-[5′-(4,6-diphenyl-1,3,5-triazin-2-yl) was used in the electron-transporting layer 6 instead of the compound (A-1). -(1,1′:3′,1″-terphenyl)-4-yl]-4-methyl-6-phenylyl-1,3,5-triazine (A-6) and Liq 50:50 ( An organic electroluminescence device was produced in the same manner as in Device Example-1, except that a film of 25 nm was formed at a rate of 0.15 nm/sec (film formation rate: 0.15 nm/sec).

Element reference example-1
In Device Example-1, 2-[3-{2-(4,6-dimethylpyrimidyl)}-5-(9-phenanthryl)phenyl was used in the electron-transporting layer 6 instead of the compound (A-1). ]-4,6-diphenyl-1,3,5-triazine (ETL-1) and Liq were deposited at a ratio of 50:50 (mass ratio) to a thickness of 25 nm (deposition rate: 0.15 nm/sec). An organic electroluminescence device was produced in the same manner as in Device Example-1. ETL-1 was synthesized by the method described in Synthesis Example-27 of JP-A-2015-027986.

A direct current was applied to the produced organic electroluminescence device, and the luminous properties were evaluated according to the method described in the measurement of luminous properties.

As light emission characteristics, the voltage (V) and power efficiency (lm/A) when a current density of 10 mA/cm ² was applied were measured, and the life of the element during continuous lighting was measured. The device life was measured by measuring the luminance decay time during continuous lighting when the device was driven at an initial luminance of 1000 cd/m ² , and measuring the time (hr) required for the luminance (cd/m ² ) to decrease by 5%. The values of voltage (V), power efficiency (lm/A), and life are expressed as relative values when the element reference example-1 is set to 100. Table 1 shows the results.

From Table 1, it was found that the organic electroluminescence device using the triazine compound (1) can achieve these in terms of voltage, luminous efficiency, and device life at a higher level than the reference example. .

INDUSTRIAL APPLICABILITY The present invention can be used for organic electroluminescence devices exhibiting high luminous efficiency and long life characteristics. Moreover, the present invention can be suitably used as an electron transport material in an organic transistor in addition to the organic electroluminescence device.

1. Substrate 2 . Anode 3 . hole injection layer 4 . hole transport layer 41 . First hole transport layer 42 . Second hole transport layer 5 . Light-emitting layer 6 . electron transport layer 7 . electron injection layer 8 . Cathode 9 . hole blocking layer 100 . organic electroluminescent element

Claims (14)

Alkyltriazine compound represented by formula (1):

During the ceremony,
At least one of R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 18 carbon atoms, and the remainder of R ¹ , R ² , R ³ and R ⁴ each have an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted by an alkyl group, phenyl group, pyridyl group or cyano group having 1 to 18 carbon atoms; or an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or A heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring optionally substituted with a cyano group; represents:
L represents a divalent aromatic hydrocarbon group consisting only of a 6-membered ring or a divalent nitrogen-containing aromatic group consisting only of a 6-membered ring:
p represents 0, 1 or 2:
q represents 0, 1 or 2:
When p is 2, L may be the same or different:
R ⁵ is a hydrogen atom; an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; an alkyl group having 1 to 18 carbon atoms a heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring optionally substituted by a group, a phenyl group, a pyridyl group or a cyano group; or a silyl group represented by Si(Ar) ₃ ; :
Each Ar independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms. Among R ¹ , R ² , R ³ and R ⁴ , R ¹ , R ² , R ³ and R ⁴ other than alkyl groups having 1 to 18 carbon atoms are alkyl groups having 1 to 6 carbon atoms and phenyl groups 2. The alkyltriazine compound according to claim 1, which is an aromatic hydrocarbon group having 6 to 18 carbon atoms optionally substituted with a pyridyl group or a cyano group. 3. The alkyltriazine compound according to claim 1, wherein L is a divalent aromatic hydrocarbon group composed only of 6-membered rings. 4. The alkyltriazine compound of any one of claims 1-3, wherein p is 0 or 1. 5. The alkyltriazine compound of any one of claims 1-4, wherein p is zero. R ⁵ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group; a heteroaromatic group having 4 to 17 carbon atoms consisting only of a 6-membered ring which may be substituted with a cyano group; or a silyl group represented by Si(Ar) ₃ ; R ⁵ is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group; 4 to 11 carbon atoms consisting of only one or more 6-membered rings which may be substituted with a cyano group; or a triphenylsilyl group; the alkyltriazine compound according to any one of claims 1 to 6. 8. The alkyltriazine compound of any one of claims 1-7, wherein q is 0 or 1. At least one of R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 6 carbon atoms, and the remaining R ¹ , R ² , R ³ and R ⁴ each have 6 to 18 carbon atoms. 9. The alkyltriazine compound according to any one of claims 1 to 8, which is an aromatic hydrocarbon group. at least one of R ¹ , R ² , R ³ and R ⁴ is a methyl group, and the remaining R ¹ , R ² , R ³ and R ⁴ are each an aromatic hydrocarbon group having 6 to 12 carbon atoms; 10. The alkyltriazine compound of any one of claims 1-9, wherein The alkyltriazine compound according to claim 1, represented by any one of the following formulas A-1 to A-8.

A material for an organic electroluminescence device, comprising the alkyltriazine compound according to any one of claims 1 to 11. An electron-transporting material for an organic electroluminescence device, comprising the alkyltriazine compound according to any one of claims 1 to 11. An organic electroluminescent device containing the alkyltriazine compound according to any one of claims 1 to 11.

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