Alkyltriazine Compounds

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

[Technical Field]

[0001] The present disclosure relates to an alkyltriazine compound, and further relates to a material for an organic electroluminescent device, an electron transport material for an organic electroluminescent device, and an organic electroluminescent device, each containing the alkyltriazine compound. [Background technology]

[0002] Organic electroluminescent devices have begun to be put to practical use, primarily for small mobile applications. However, further expansion of their applications requires improved performance, and materials with low-voltage driving characteristics, high luminous efficiency, and long life characteristics are required. Patent Document 1 discloses triazine compounds that are materials for organic electroluminescent devices with long life and excellent luminescent properties. Patent Document 2 also discloses that materials incorporating alkylpyrimidyl groups are effective in improving the properties of organic electroluminescent devices. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-314503 [Patent Document 2] Japanese Patent Application Laid-Open No. 2015-027986 Summary of the Invention [Problem to be solved by the invention]

[0004] The triazine compounds disclosed in Patent Documents 1 and 2 do not fully satisfy the three properties of driving voltage, luminous efficiency, and lifespan characteristics required for expanding the range of applications, depending on the application, and there is a demand for materials that achieve the above three properties at an even higher level. In particular, there is a demand for materials for organic electroluminescent devices that have superior properties, luminous efficiency and driving voltage, compared to known materials.

[0005] Therefore, one aspect of the present invention is directed to providing a triazine compound having a partial structure that contributes to the formation of an organic electroluminescent device that is excellent in two properties, namely, driving voltage and luminous efficiency. Another aspect of the present invention is directed to providing an organic electroluminescent device that exhibits high luminous efficiency and long life. [Means for solving the problem]

[0006] As a result of extensive research aimed at solving the above problems, the present inventors have found that introducing a triazyl group substituted with an alkyl group into a triazine derivative used in an electron transport layer is effective in improving device efficiency and reducing driving voltage, and have thus completed the present invention. That is, the present invention relates to the following (A) to (F).

[0007] (a) An alkyltriazine compound represented by formula (1).

[0008] [ka]

[0009] During the ceremony, R 1 , R 2 , R 3 and R 4 At least one of R is an alkyl group having 1 to 18 carbon atoms; 1 , R 2 , R 3 and R 4 and the remainder of each represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; or a heteroaromatic group having 4 to 17 carbon atoms which consists solely of a 6-membered ring which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group: L represents a divalent aromatic hydrocarbon group consisting of only six-membered rings or a divalent nitrogen-containing aromatic group consisting of only six-membered rings: p represents 0, 1 or 2: q represents 0, 1 or 2: When p is 2, L may be the same or different from each other: R 5 represents a hydrogen atom; an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group or a cyano group; a heteroaromatic group having 4 to 17 carbon atoms which consists of a 6-membered ring which may be substituted with an alkyl group having 1 to 18 carbon atoms, 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.

[0010] (b) R 1 , R 2 , R 3 , and R 4 Among these, R other than alkyl groups having 1 to 18 carbon atoms 1 , R 2 , R 3 , and R 4 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, a phenyl group, a pyridyl group or a cyano group.

[0011] (c) The alkyltriazine compound according to (a) or (b), wherein L is a divalent aromatic hydrocarbon group consisting of only 6-membered rings.

[0012] (iv) The alkyltriazine compound according to any one of (a) to (c), wherein p is 0 or 1.

[0013] (e) The alkyltriazine compound according to any one of (a) to (d), wherein p is 0.

[0014] (F)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 which is composed only of a 6-membered ring which may be substituted with a cyano group; or a silyl group represented by Si(Ar)3.

[0015] (G)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 11 carbon atoms which is composed only of a 6-membered ring which may be substituted with a cyano group; or a triphenylsilyl group.

[0016] (H) The alkyltriazine compound according to any one of (A) to (G), wherein q is 0 or 1.

[0017] (R)R 1 , R 2 , R 3 and R 4 At least one of the R 1 , R 2 , R 3 and R 4 and each represent an aromatic hydrocarbon group having 6 to 18 carbon atoms.

[0018] (Nu)R 1 , R 2 , R 3 and R 4 At least one of the R 1 , R 2 , R 3 and R 4 and each represent an aromatic hydrocarbon group having 6 to 12 carbon atoms.

[0019] (k) The alkyltriazine compound according to (a), which is represented by any one of the following formulae A-1 to A-8.

[0020] [ka]

[0021] (l) A material for an organic electroluminescent device, comprising the alkyltriazine compound according to any one of (a) to (k).

[0022] (10) An electron transport material for an organic electroluminescent device, comprising the alkyltriazine compound according to any one of (1) to (11).

[0023] (f) An organic electroluminescent device containing the alkyltriazine compound according to any one of (i) to (k). [Effects of the Invention]

[0024] According to one aspect of the present invention, an alkyltriazine compound is provided that contributes to the formation of an organic electroluminescent device that exhibits high-level low-voltage driving characteristics and luminous efficiency characteristics. According to another aspect of the present invention, a material for an organic electroluminescent device that includes the alkyltriazine compound is provided. According to yet another aspect of the present invention, an organic electroluminescent device that exhibits high luminous efficiency and long life characteristics is provided. [Brief explanation of the drawings]

[0025] [Figure 1] 1 is a schematic cross-sectional view of a first preferred embodiment of an organic electroluminescent device containing an alkyltriazine compound, which is one aspect of the present invention. [Figure 2] FIG. 1 is a schematic cross-sectional view of a second preferred embodiment of an organic electroluminescent device containing an alkyltriazine compound, which is an aspect of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0026] Hereinafter, an alkyltriazine compound according to one embodiment of the present invention (hereinafter, sometimes referred to as alkyltriazine compound (1)) will be described in detail.

[0027] <Alkyltriazine compound (1)> The alkyltriazine compound (1) according to one embodiment of the present invention is a triazine compound represented by formula (1):

[0028] [ka]

[0029] [R 1 , R 2 , R 3 and R 4 About R 1 , R 2 , R 3 and R 4 each independently represents an alkyl group having 1 to 18 carbon atoms; an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group, or a cyano group; or a heteroaromatic group having 4 to 17 carbon atoms which consists solely of a 6-membered ring which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group, or a cyano group, provided that R 1 , R 2 , R 3 and R 4 At least one of the groups is an alkyl group having 1 to 18 carbon atoms.

[0030] In the embodiments of the present invention, the term "aromatic hydrocarbon group" refers to a group composed of one or more aromatic rings. The aromatic hydrocarbon group may be a group of one aromatic ring, a group composed of multiple aromatic rings linked together by carbon bonds, or a fused polycyclic aromatic group.

[0031] Furthermore, the "heteroaromatic group" may be composed of only six-membered rings, and may be a group of one heteroaromatic ring, a group composed of multiple aromatic ring groups including a heteroaromatic ring linked by carbon bonds, or a fused polycyclic heteroaromatic group having a structure in which multiple aromatic ring groups including a heteroaromatic ring are fused.

[0032] R 1 , R 2 , R 3 and R 4Examples of the alkyl group include a methyl group, a cyclohexylmethyl group, an ethyl group, a 2-cyclopentylethyl group, a propyl group, a 2-methylpropyl group, a 2,2-dimethylpropyl group, a 3-cyclopropylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-methylpropyl group, a 1,2-dimethylpropyl group, a 1,1-dimethylethyl group, a cyclobutyl group, a pentyl group, a 2-methylpentyl group, a 3-ethylpentyl group, a 2,4-dimethylpentyl group, a 2-pentyl group, a 2-methylpentyl group, a hexyl, 2-methylhexyl, 3,3-dimethylhexyl, 4-ethylhexyl, 2-hexyl, 2-methylhexan-2-yl, 5,5-dimethylhexan-2-yl, 3-hexyl, 2,4-dimethylhexan-3-yl, cyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl silyl, 4,4-dimethylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, 4-heptyl, bicyclo[2.2.1]heptyl, octyl, 2-octyl, 3-octyl, 4-octyl, cyclooctyl, bicyclo[2.2.2]octyl, nonyl, 5-nonyl, decyl, 2-decyl, 5-decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, phenyl, 1-naphthyl, 2-naphthyl, 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-cyanophenyl 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-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-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.

[0033] The alkyltriazine compound (1) has excellent properties as a material for an organic electroluminescent device, and therefore R 1 , R 2 , R 3 and R 4 are each independently preferably an alkyl group having 1 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, a phenyl group, a pyridyl group, or a cyano group, and more preferably an alkyl group having 1 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cyano group. 1 , R 2 , R 3 and R 4 are each independently an alkyl group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms. In terms of ease of synthesis of the alkyltriazine compound (1), R 1 , R 2 , R 3 and R 4 are each independently a methyl group or an aromatic hydrocarbon group having 6 to 12 carbon atoms.

[0034] [About L] L represents a divalent aromatic hydrocarbon group consisting of only 6-membered rings or a divalent nitrogen-containing aromatic group consisting of only 6-membered rings. p represents 0, 1, or 2. When p is 2, L may be the same or different.

[0035] Examples of L include an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a 2,3-pyridylene group, a 2,4-pyridylene group, a 2,5-pyridylene group, a 2,6-pyridylene group, a 3,4-pyridylene group, a 3,5-pyridylene group, a 3,5-pyridylene group, a 3,5-pyridylene group, a 2,3-pyrazylene group, a 2,5-pyrazylene group, a 2,6-pyrazylene group, a 2,4-pyrimidylene group, a 2,4-pyrimidylene group, a 2,5-pyrimidylene group, a 4,5-pyrimidylene group, a 4,6-pyrimidylene group, and a 2,4-triazylene group.

[0036] In view of the good properties of the alkyltriazine compound (1) as a material for an organic electroluminescent device, L is preferably a phenylene group or a pyridylene group, and in view of the ease of synthesis of the alkyltriazine compound (1), L is more preferably a divalent aromatic hydrocarbon group consisting of only six-membered rings, such as a phenylene group.

[0037] p is 0, 1 or 2, and is preferably 0 or 1, more preferably 0, in that the alkyltriazine compound (1) has an appropriate glass transition temperature.

[0038] [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 temperature.

[0039] [R 5 About R 5 represents a hydrogen atom; an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 18 carbon atoms, a phenyl group, a pyridyl group, or a cyano group; a heteroaromatic group having 4 to 17 carbon atoms which consists solely of a 6-membered ring which may be substituted with an alkyl group having 1 to 18 carbon atoms, 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 a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, an anthranyl group, a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, and a chrysenyl group.

[0040] R 5Examples of the alkyl group include a hydrogen atom, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9-anthranyl group, a 9-phenanthrenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a (3'-cyano)biphenyl-2-yl group, a (3'-cyano)biphenyl-3-yl group, a (3'-cyano)biphenyl-4-yl group, a (3'-cyano)biphenyl-2-yl group, a (4'-cyano)biphenyl-3-yl group, a (4'-cyano)biphenyl-4-yl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a ... phenyl 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-pyrimidyl group pyridyl group, 3,5-dimethyl-2-pyridazyl 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,Examples of the silyl group include a 5-dimethylpyridin-3-yl group, a 2-cyanopyridin-2-yl group, a 3-cyanopyridin-2-yl group, a 4-cyanopyridin-2-yl group, a 5-cyanopyridin-2-yl group, a 2-cyanopyridin-3-yl group, a 4-cyanopyridin-3-yl group, a 5-cyanopyridin-3-yl group, a 6-cyanopyridin-3-yl group, a 2-cyanopyridin-4-yl group, a 3-cyanopyridin-4-yl group, a 2-quinolinyl group, a 4-quinolinyl group, an 8-quinolinyl group, a 2-quinoxalinyl group, a 9-phenanthrolinyl group, a triphenylsilyl group, a tris(1-naphthyl)silyl group, and a tris(2-naphthyl)silyl group.

[0041] The alkyltriazine compound (1) has good properties as a material for organic electroluminescent devices, and therefore R 5 is preferably 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 which is composed only of a 6-membered ring which may be substituted with a cyano group, or a silyl group represented by Si(Ar)3, and more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a cyano group, a heteroaromatic group having 4 to 11 carbon atoms which is composed only of a 6-membered ring which may be substituted with a cyano group, or a triphenylsilyl group. 5 is more preferably a phenyl group, a biphenylyl group, a phenanthrenyl group, a pyridyl group, or a triphenylsilyl group.

[0042] [Specific examples of alkyltriazine compound (1)] Specific examples of the alkyltriazine compound (1) include the following (A-1) to (A-8) and (B-1) to (B-165), but the present invention is not limited to these.

[0043] [ka]

[0044] [ka]

[0045]

change

[0046]

change

[0047]

change

[0048]

change

[0049]

change

[0050]

change

[0051]

change

[0052]

change

[0053]

change

[0054]

change

[0055] As the alkyltriazine compound (1), the compounds represented by (A-1), (A-3) or (A-8) are preferred because they have good performance as an electron transport material in an organic electroluminescent device.

[0056] <Synthesis of alkyltriazine compound (1)> Next, a method for producing the alkyltriazine compound (1) will be described.

[0057] The alkyltriazine compound (1) can be produced by the method shown in the following synthetic route 1 or synthetic route 2. The compound (1a) included in the alkyltriazine compound (1) (hereinafter, sometimes referred to as alkyltriazine compound (1a)) can be produced by the method shown in synthetic route 3.

[0058] [ka]

[0059] In formulas (1a), (3), (3b), (4), and (5), R 1 , R 2 , R 3 , R 4 , R 5 , L, p, and q are defined as R in Eq. (1), respectively. 1 , R 2 , R 3 , R 4 , R 5 ,L, is the same as the definition of p and q; Y 1 and Y 2 each independently represents a halogen atom or a trifluoromethanesulfonyloxy group; R 6 , R 7 and R 8 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; Two ORs bonded to one boron atom 6 Group, OR 7 group or OR 8The groups may be the same or different; Two ORs bonded to one boron atom 6 Group, OR 7 group or OR 8 The group and the boron atom to which it is bonded may together form a ring.

[0060] Y 1 and Y 2 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. A chlorine atom or a bromine atom is preferred in terms of the yield of the alkyltriazine compound (1) or (1a).

[0061] OR bonded to boron atom 6 Group, OR 7 group or OR 8 Examples of the group include OH, OMe, and O i Examples include Pr, OBu, and OPh. Me represents a methyl group. i Pr represents an isopropyl group, Bu represents a butyl group, and Ph represents a phenyl group.

[0062] Two OR 6 Group, OR 7 group or OR 8 When the group and the boron atom to which it is bonded together form a ring, B(OR 6 )2, B(OR 7 )2, or B(OR 8 Examples of 2 include the following groups (I) to (VIII), with the group (II) being preferred in terms of good yield.

[0063] [ka]

[0064] The coupling reaction in synthetic routes 1 to 3 is a method of reacting a triazine compound represented by formula (2) or (4) with a boron compound represented by formula (3), (3b) or (5) in the presence of a palladium catalyst and a base, and the method disclosed in JP 2011-063584 A or general reaction conditions for the Suzuki-Miyaura reaction can be applied.

[0065] The boron compound (3), (3b) or (5) can be produced, for example, according to the method disclosed in JP 2011-063584 A, JP 2017-141216 A, WO 2015114102 A or The Journal of Organic Chemistry, Vol. 60, p. 7508, 1995.

[0066] The triazine compound (2) or (4) can be produced according to the reference examples or prior art documents, for example, JP 2018-030792 A, Synthesis, Vol. 10, paragraph 841, 1980, or The Journal of Organic Chemistry, Vol. 30, page 702, 1965. Commercially available products may also be used. The triazine compound is preferably used in an amount of 0.5 to 3.0 molar equivalents relative to the boron compound, as this provides a good reaction yield.

[0067] 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. Other examples include complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, and dichlorobis(benzonitrile)palladium; and palladium complexes having tertiary phosphines as ligands, such as dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, and dichlorobis(tricyclohexylphosphine)palladium. These catalysts can also be prepared in situ by adding a tertiary phosphine to a palladium salt or complex compound.

[0068] 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(diphenylphosphine), 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.

[0069] Among these, palladium complexes having a tertiary phosphine as a ligand are preferred in terms of good yield, and palladium complexes having triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, or tricyclohexylphosphine as a ligand are more preferred.

[0070] The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:2 to 3:1 in terms of good yield. There is no limitation on the amount of palladium catalyst used in the coupling reaction in Synthetic Routes 1 to 3, but in terms of good yield, the molar equivalent of the palladium catalyst is preferably in the range of 0.005 to 0.5 molar equivalents relative to the boron compound.

[0071] Examples of bases used in the coupling reactions in Synthetic Routes 1 to 3 include metal hydroxide salts such as sodium hydroxide, potassium hydroxide, and calcium hydroxide; metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate; 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 metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, and potassium tert-butoxide. Among these, metal carbonates or metal phosphates are preferred in terms of high reaction yield, with potassium carbonate or sodium carbonate being more preferred. There are no particular limitations on the amount of base used. In terms of high 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.

[0072] The coupling reactions in Synthetic Routes 1 to 3 can be carried out in a solvent. Examples of the solvent include water; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ- Examples of suitable solvents include esters such as lactones; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); dimethyl sulfoxide (DMSO); and alcohols such as methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol. These may be used alone or in any combination. There are no particular limitations on the amount of solvent used. Among these, water, ethers, amides, alcohols, or mixed solvents thereof are preferred due to their high reaction yield, and a mixed solvent of THF and water is even more preferred.

[0073] The coupling reactions in synthetic routes 1 to 3 can be carried out at a temperature appropriately selected from 0°C to 200°C, and are preferably carried out at a temperature appropriately selected from 60°C to 160°C in terms of good reaction yield.

[0074] After completion of the coupling reactions in synthetic routes 1 to 3, alkyltriazine compounds (1) and (1a) can be obtained by appropriately combining general purification treatments such as recrystallization, column chromatography, sublimation purification, and preparative HPLC as needed.

[0075] <Materials for organic electroluminescent devices> A material for organic electroluminescent devices according to one embodiment of the present disclosure contains the aforementioned alkyltriazine compound (1). The material for organic electroluminescent devices may consist solely of the aforementioned alkyltriazine compound (1), or may further contain other components such as a dopant in addition to the alkyltriazine compound (1), as long as the desired properties and performance are exhibited.

[0076] <Electron transport material for organic electroluminescent devices> The electron transport material for organic electroluminescent devices according to one embodiment of the present disclosure contains the aforementioned alkyltriazine compound (1). The electron transport material for organic electroluminescent devices may consist solely of the aforementioned alkyltriazine compound (1), or may further contain other components such as a dopant in addition to the alkyltriazine compound (1), as long as the desired properties and performance are exhibited.

[0077] <Organic electroluminescent device> An organic electroluminescent device according to one embodiment of the present disclosure (hereinafter, sometimes simply referred to as an organic electroluminescent device) containing an alkyltriazine compound (1) will be described below.

[0078] An organic electroluminescent device according to one aspect of the present disclosure contains an alkyltriazine compound (1). In the organic electroluminescent device according to an embodiment of the present invention, the alkyltriazine compound (1) is contained in the organic electroluminescent device in a state where the above-described material for organic electroluminescent devices or the electron transport material for organic electroluminescent devices is applied.

[0079] The configuration of the organic electroluminescent device is not particularly limited, but examples thereof include the following configurations (i) to (v). (i): Anode / Emitting layer / Cathode (ii): Anode / hole transport layer / light-emitting layer / cathode (iii): Anode / 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

[0080] The alkyltriazine compound (1) may be contained in any of the above layers, but is preferably contained in one or more layers selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode, in order to provide excellent light-emitting properties to the organic electroluminescent device. Therefore, in the case of the structures (i) to (v) above, the alkyltriazine compound (1) is preferably 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.

[0081] Hereinafter, an organic electroluminescent device according to one embodiment of the present disclosure will be described in more detail with reference to FIG. 1, taking the above configuration (v) as an example.

[0082] 1 has a so-called bottom-emission type element configuration, the organic electroluminescent element according to one embodiment of the present disclosure is not limited to a bottom-emission type element configuration. That is, the organic electroluminescent element according to one embodiment of the present disclosure may have another known element configuration, such as a top-emission type.

[0083] Fig. 1 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescent device containing an alkyltriazine compound (1) according to one embodiment of the present disclosure. Fig. 2 is a schematic cross-sectional view showing another example of a layer structure of an organic electroluminescent device containing an alkyltriazine compound (1) according to one embodiment of the present disclosure.

[0084] The organic electroluminescent device 100 comprises, in this order, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8. However, some of these layers may be omitted, or other layers may be added. For example, as shown in FIG. 2, a hole blocking layer 9 may be provided between the emitting layer 5 and the electron transport layer 6. Alternatively, the hole injection layer 3 may be omitted, and the hole transport layer 4 may be provided directly on the anode 2. Furthermore, a single layer having the functions of multiple layers, such as an electron injection / transport layer that combines the functions of both the electron injection layer and the electron transport layer, may be provided instead of the multiple layers. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be composed of multiple 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 may be provided overlapping in this order from the hole injection layer 3 side.

[0085] [Layer containing alkyltriazine compound (1)] 1, the organic electroluminescent device 100 contains an 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 7. In particular, it is preferable that the electron transport layer 6 contains the alkyltriazine compound (1). The alkyltriazine compound (1) may be contained in multiple layers of the organic electroluminescent device.

[0086] In the following, an organic electroluminescent device 100 in which the electron transport layer 6 contains the alkyltriazine compound (1) will be described.

[0087] [Board 1] The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate.

[0088] 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 light-transmitting plastic film are preferred.

[0089] Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), etc.

[0090] In the case of a configuration in which light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[0091] [Anode 2] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).

[0092] Examples of anode materials include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (e.g., 4 eV or more). Specific examples of anode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO.

[0093] In the case of an organic electroluminescent device configured so that light is extracted through the anode, the anode is formed from a conductive transparent material that is transparent or substantially transparent to the light emitted.

[0094] [Hole injection layer 3, hole transport layer 4] Between the anode 2 and the light-emitting layer 5 described below, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side.

[0095] The hole injection layer and the hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer. By interposing these hole injection layer and hole transport layer between the anode and the light-emitting layer, a large number of holes can be injected into the light-emitting layer with a lower electric field.

[0096] The hole injection layer and the hole transport layer also function as electron barrier 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 prevented from leaking to the hole injection layer and / or the hole transport layer due to the electron barrier present at the interface between the light-emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons accumulate at the interface within the light-emitting layer, resulting in effects such as improved light-emitting efficiency, and an organic electroluminescent device with excellent light-emitting performance can be obtained.

[0097] The material for the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property, and may be either organic or inorganic.

[0098] Specific examples of materials 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 chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, etc. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, in terms of good performance of organic electroluminescent devices.

[0099] Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'-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).

[0100] Furthermore, inorganic compounds such as p-type Si and p-type SiC can also be given as examples of materials for the hole injection layer and the hole transport layer.

[0101] The hole injection layer and the hole transport layer may have a single structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0102] [Emitting layer 5] The light-emitting layer 5 is provided between the hole transport layer 4 and the electron transport layer 6 described below.

[0103] Materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

[0104] The light-emitting layer may consist of a single small molecule or polymer material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from the dopant and can be of any color.

[0105] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group. More specific examples include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole], and 9,10-bis(biphenyl)anthracene.

[0106] Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, and carbostyril compounds. The fluorescent dopant may be a combination of two or more selected from these.

[0107] Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0108] 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](acetylacetonate)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

[0109] Furthermore, the light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole transport layer 4 or electron transport layer 6). This can further increase the current efficiency of the organic electroluminescent device.

[0110] The light-emitting layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0111] [Electron transport layer 6] An electron transport layer 6 is provided between the light emitting layer 5 and the electron injection layer 7 described below.

[0112] The electron transport layer has a function of transporting electrons injected from the cathode to the light-emitting layer. By interposing the electron transport layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0113] As described above, the electron transport layer preferably contains the alkyltriazine compound (1). In addition to the alkyltriazine compound (1), the electron transport layer may further contain one or more types selected from conventionally known electron transport materials.

[0114] When the triazine compound (1) is not contained in the electron transport layer but is contained in another layer, one or more electron transport materials selected from conventionally known electron transport materials can be used as the electron transport material constituting the electron transport layer.

[0115] Conventionally known electron transporting materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include 8-hydroxyquinolinatolithium (Liq), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, and tris(8-hydroxyquinolinato)gallium. bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)-1-naphtholatoaluminum, and bis(2-methyl-8-quinolinato)-2-naphtholatogallium.

[0116] The electron transport layer may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0117] In the organic electroluminescent device according to this embodiment, an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, luminous efficiency, low driving voltage, or high durability).

[0118] [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.

[0119] The electron injection layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0120] Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, and anthrone, as well as inorganic compounds such as various oxides, nitrides, and oxynitrides, including SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C.

[0121] [Cathode 8] A cathode 8 is provided on the electron injection layer 7 .

[0122] In the case of an organic electroluminescent element having a configuration in which only light emitted through the anode is extracted, the cathode can be formed from any conductive material.

[0123] Examples of materials for the cathode include metals with a low work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, a metal with a low work function is, for example, a metal with a work function of 4 eV or less.

[0124] 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 (Al2O3) mixtures, indium, lithium / aluminum mixtures, and rare earth metals.

[0125] Among these, from the viewpoints of electron injection properties and durability against oxidation, etc., a mixture of an electron-injecting metal and a second metal that has a larger and more stable work function than the electron-injecting metal, such as a magnesium / silver mixture, a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al2O3) mixture, or a lithium / aluminum mixture, is preferred.

[0126] [Hole-blocking layer 9] As described above, a hole-blocking layer 9 may be provided between the light-emitting layer 5 and the electron-transporting layer 6. The hole-blocking layer has the function of preventing holes or excitons from penetrating from the light-emitting layer into the electron-transporting layer. Examples of materials for the hole-blocking layer include the triazine compound represented by formula (1) in JP 2021-145126 A and the triazine compound described in JP 2018-507174 A.

[0127] [How each layer is formed] Each layer except for the electrodes (anode and cathode) described above can be formed into a thin film by a known method such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method. The material for each layer may be used alone or, if necessary, together with a binder resin or other material or a solvent.

[0128] There are no particular limitations on the thickness of each layer thus formed, and it can be selected appropriately depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0129] The anode and cathode can be formed by thinning the electrode material by methods such as vapor deposition, sputtering, etc. 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, etc.

[0130] The thickness of the anode and cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0131] The layer containing the triazine compound (1) may be used in combination with the above-mentioned conventionally known electron transporting material. For example, the alkyltriazine compound (1) and the conventionally known electron transporting material may be co-deposited, or a layer of the conventionally known electron transporting material may be laminated on the layer of the alkyltriazine compound (1).

[0132] Organic electroluminescent elements may be used as a type of lamp for illumination or exposure light sources, or as a projection device that projects images onto a screen or the like, or as a display device (display) that directly recognizes still images or moving images. When organic electroluminescent elements are used as a display device for playing moving images, the driving method may be a simple matrix (passive matrix) method or an active matrix method. Furthermore, by using two or more types of organic electroluminescent elements having different emission colors, it is possible to produce a full-color display device.

[0133] When used as an electron transport layer, alkyltriazine compound (1) can provide organic electroluminescent devices with significantly superior luminous efficiency and long life characteristics compared to conventionally known triazine compounds. Furthermore, alkyltriazine compound (1) has high electron mobility and excellent carrier transport properties due to its planar skeleton. Therefore, it can reduce the driving voltage of organic electroluminescent devices, improve luminous efficiency, and extend the device life.

[0134] The alkyltriazine compound (1) can be used as an electron transport layer in an organic electroluminescent device to provide a triazine compound that can achieve a high level of low driving voltage, high efficiency, and long life of the device. Furthermore, an organic electroluminescent device that can achieve a low driving voltage, high efficiency, and long life using the alkyltriazine compound (1) can be provided.

[0135] This configuration makes it possible to provide an organic electroluminescent device that exhibits even higher luminous efficiency and longer life characteristics. This is expected to contribute to the development of image display technology with even higher resolution and longer life. Therefore, the embodiments of the present invention are expected to contribute to improving work motivation, industrial development, and achieving the Sustainable Development Goals (SDGs) related to environmental conservation, from the perspectives of improving the accuracy of information transmission and reducing the environmental burden caused by waste.

[0136] The present invention is not limited to the above-described embodiments, and various modifications are possible within the scope of the claims. Embodiments obtained by appropriately combining the technical means disclosed in different embodiments are also included in the technical scope of the present invention. [Example]

[0137] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0138] [ 1 H-NMR measurement] 1 For the H-NMR measurement, a Bruker ASCEND HD (400 MHz; manufactured by BRUKER) was used. 1 H-NMR was measured using deuterated chloroform (CDCl3) as the measurement solvent and tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0139] [Emission characteristics measurement] The light emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the device prepared in each example (described later) in a 25° C. environment using a luminance meter BM-9 (manufactured by Topcon Technohouse Corporation).

[0140] [Compound synthesis] Synthesis Example 1 4,6-diphenyl-2-[3-(9-phenanthrenyl)-5-[(4,6-dimethyl)-1,3,5-triazin-2-yl]phenyl-1,3,5-triazine

[0141] [ka]

[0142] 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), and tetrakis(triphenylphosphine)palladium (1.40 g, 1.21 mmol) were suspended in THF (240 mL). To this suspension was added 2.0 M aqueous potassium carbonate (37.0 mL), and the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The resulting solid was collected by filtration, purified by silica gel column chromatography (chloroform) and washed with toluene to obtain 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) (3.47 g, 5.85 mmol, 29%). 1 H-NMR(CDCl3)δ(ppm):2.76(s,6H),7.54-7.64(m,7H),7.67(ddd,J=7.9,6.9,1.1 Hz,1H),7.73(dddd,J=8.2,7.1,3.1,1.3Hz,1H),7.88(s,1H),7.94(dd,J=8.2,0.8 Hz,1H).7.98(dd,J=7.7,1.2Hz,1H),8.78-8.82(m,5H),8.85(d,J=8.2Hz,1H),8. 94(dd,J=1.7,1.7Hz,2H),9.11(dd,J=1.7,1.7Hz,1H)9.94(dd,J=1.7,1.6Hz,1H).

[0143] 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

[0144] [ka]

[0145] Under an argon atmosphere, 4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(9-phenanthrenyl)-phenyl]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), and tetrakis(triphenylphosphine)palladium (400 mg, 0.344 mmol) were suspended in THF (80 mL). 2M aqueous sodium carbonate solution (10.0 mL) was added, and the mixture was heated to 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 from toluene to obtain the desired 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) (1.46 g, 2.24 mmol, 35%). 1 H-NMR(CDCl3)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=1.7Hz,1H).

[0146] Synthesis 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

[0147] [ka]

[0148] Under an argon atmosphere, 4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-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), and tetrakis(triphenylphosphine)palladium (500 mg, 0.43 mmol) were suspended in THF (80 mL). To this suspension was added 2 M aqueous sodium carbonate solution (13.0 mL), and the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and recrystallized from toluene to obtain the desired 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) (3.89 g, 6.22 mmol, 72%). 1 H-NMR(CDCl3)δ(ppm):2.83(s,3H),7.11(tt,J=6.6,1.2Hz,1H),7.23(tt,J=8.0,1.5Hz,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).

[0149] Synthesis Example 4 6,6'-{5-(triphenylsilyl)phenyl-1,3-yl)-bis(2-methyl-4-phenyl-1,3,5-triazine)

[0150] [ka]

[0151] Under an argon atmosphere, 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 (1.70 g, 8.09 mmol), dichlorobis(triphenylphosphino)palladium (78 mg, 0.11 mmol), 2 M aqueous potassium carbonate (12.0 mL, 24 mmol), and THF (18 mL) were added and heated to reflux for 22 hours. After cooling, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and recrystallized from toluene to give 2,2'-(5-triphenylsilyl-1,3-phenylene)bis(4-methyl-6-phenyl-1,3,5-triazine) (A-4) (yield 1.21 g, 49%). 1 H-NMR(CDCl3)δ(ppm):2.81(s,6H),7.60(brt,J=7.3Hz,2H),7.44-7.55(m,1 3H),7.72(m,6H),8.55(m,4H),9.14(d,J=1.7Hz,2H),9.82(t,J=1.7Hz,1H).

[0152] Synthesis Example 5 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

[0153] [ka]

[0154] Under an argon atmosphere, 4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-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), and tetrakis(triphenylphosphine)palladium (60 mg, 0.05 mmol) were suspended in THF (10 mL). 2M aqueous sodium carbonate solution (1.5 mL) was added to the suspension, and the mixture was heated to 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 obtain 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) (309 mg, 0.43 mmol, 43%). 1 H-NMR(CDCl3)δ(ppm):2.85(s,3H),7.13(tt,J=7.2,1.3Hz,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=1.7,1.6Hz,1H).

[0155] Synthesis 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

[0156] [ka]

[0157] 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). 2M aqueous potassium carbonate (10 mL, 20 mmol) was added to the suspension, and the mixture was stirred at 80 °C for 22 h. After cooling to room temperature, water, methanol, and hexane were added, and the precipitate was collected by filtration. The precipitate was suspended in xylene (400 mL), heated to 140°C, added with activated carbon, 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) (2.64 g, yield 69%). 1 H-NMR(CDCl3)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=6.6Hz,2H),8.83(brd,J=7.1Hz,6H),9.03(dd,J=1.6,1.6Hz,1H),9.07(dd,J=1.1.6,1.6Hz,1H).

[0158] Synthesis 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

[0159] [ka]

[0160] Under an argon atmosphere, 2,4-diphenyl-6-[3-(pyridin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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). 2M aqueous potassium carbonate (0.5 mL, 1.0 mmol) was added to the suspension, and the mixture was stirred at 80°C for 23 hours. After cooling to room temperature, water, methanol, and hexane were added, and the precipitate was collected by filtration. The residue was suspended in toluene (30 mL), heated to 110°C, activated carbon was added, and the mixture was stirred and then filtered through Celite. Low boiling points were removed by distillation, and the precipitate was collected by filtration and recrystallized from toluene (20 mL) to give 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 (A-7) (32 mg, yield 21%). 1 H-NMR(CDCl3)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).

[0161] Synthesis 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

[0162] [ka]

[0163] Under an argon atmosphere, 4,6-diphenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-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) were suspended in THF (70 mL). To this suspension was added 2 M aqueous sodium carbonate (11 mL), and the mixture was heated to 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 obtain 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) (3.66 g, 5.71 mmol, 80%). 1 H-NMR(CDCl3)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=1.7,1.6Hz,1H).

[0164] Reference example-1 2-chloro-4-methyl-6-(4-biphenylyl)-1,3,5-triazine

[0165] [ka]

[0166] 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 in THF (0.5 mL) was added over 3 minutes, followed by stirring at room temperature for 6 hours. 500 μL of 1M hydrochloric acid was added to the reaction mixture, which was then stirred at room temperature for 30 minutes. The reaction mixture was dried over sodium sulfate and then filtered to remove solid components. The solvent was removed from the filtrate by distillation under reduced pressure, followed by washing with methanol to obtain the desired 2,4-dichloro-6-(4-biphenylyl)-1,3,5-triazine (85% purity). (v) (261 mg). 1 H-NMR(CDCl3)δ2.73(s,3H),7.35(tt,J=7.6,1.2Hz,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=7.6,1.6,1.3Hz,2H).

[0167] [Example of organic electroluminescent device] Element Example 1 (see Figure 2) (Prepare substrate 1 and anode 2) A glass substrate with an indium tin oxide (ITO) transparent electrode, on which a 2 mm wide striped pattern of an ITO film (thickness: 110 nm), was prepared as a substrate 1 having an anode 2 on its surface. Next, this substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning.

[0168] (Preparation for vacuum deposition) After cleaning, each layer was deposited on the surface-treated substrate by vacuum deposition using a vacuum deposition method, and each layer was laminated.

[0169] First, the glass substrate was placed in a vacuum deposition chamber. -4 The pressure was reduced to 100 Pa. Then, each layer was formed in the following order according to the film formation conditions. Each organic material was formed by resistance heating.

[0170] (Fabrication of Hole Injection Layer 3) Sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a mass ratio of 99:1 to form a 10 nm film, forming a hole injection layer 3. The film formation rate was 0.1 nm / sec.

[0171] (Fabrication of First Hole Transport Layer 41) Sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was deposited at a rate of 0.2 nm / sec to form a 85 nm film, thereby forming a first hole transport layer 41.

[0172] (Fabrication of the 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 film of 5 nm, thereby forming second hole transport layer 42 .

[0173] (Fabrication of Light-Emitting Layer 5) Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene were mixed in a mass ratio of 95:5 to form a 20 nm film, thereby producing the light-emitting layer 5. The film formation rate was 0.1 nm / sec.

[0174] (Fabrication of Hole Blocking Layer 9) Sublimation-purified 2-{3'-(9,9-dimethylfluoren-2-yl)-biphenylyl-3-yl}-4,6-diphenyl-1,3,5-triazine was deposited at a rate of 0.05 nm / sec to form a 6 nm thick film as a hole blocking layer 9 .

[0175] (Fabrication 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 mixed in a mass ratio of 50:50 to form a 25 nm film, thereby producing an electron transport layer 6. The film formation rate was 0.15 nm / sec.

[0176] (Fabrication of Electron Injection Layer 7) Liq was deposited at a rate of 0.02 nm / sec to a thickness of 1 nm to form an electron injection layer 7 .

[0177] (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 had a two-layer structure, with silver / magnesium (mass ratio 1 / 10) and silver deposited in that order to thicknesses of 80 nm and 20 nm, respectively. The silver / magnesium deposition rate was 0.5 nm / sec, and the silver deposition rate was 0.2 nm / sec.

[0178] As a result, the light-emitting area of ​​4mm as shown in Figure 2 2 An organic electroluminescent device 100 was produced. The thickness of each film was measured using a stylus film thickness measuring instrument (DEKTAK, manufactured by Bruker).

[0179] The device was then sealed in a nitrogen atmosphere glove box with an oxygen and moisture concentration of 1 ppm or less by sealing the glass sealing cap and the film-formed substrate (device) with bisphenol F epoxy resin (manufactured by Nagase ChemteX Corporation).

[0180] Element Example 2 An organic electroluminescent device was prepared in the same manner as in Element Example 1, except that in Element Example 1, a 25 nm film (film formation rate: 0.15 nm / sec) of sublimation-purified 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 were formed in a mass ratio of 50:50 in place of compound (A-1) in the electron transport layer 6.

[0181] Element Example 3 An organic electroluminescent device was prepared in the same manner as in Device Example 1, except that in Device Example 1, a 25 nm film (film formation rate: 0.15 nm / sec) of sublimation-purified 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) and Liq were formed in a 50:50 (mass ratio) ratio in the electron transport layer 6 instead of compound (A-1).

[0182] Element Example 4 An organic electroluminescent device was produced in the same manner as in Device Example 1, except that in Device Example 1, a 25 nm film (film formation rate: 0.15 nm / sec) of sublimation-purified 2-[5'-(4,6-diphenyl-1,3,5-triazin-2-yl)-(1,1':3',1''-terphenyl)-4-yl]-4-methyl-6-phenylyl-1,3,5-triazine (A-6) and Liq were formed in a mass ratio of 50:50 in place of compound (A-1) in the electron transport layer 6.

[0183] Element reference example 1 An organic electroluminescent device was fabricated in the same manner as in Element Example 1, except that a 25 nm film (film formation rate: 0.15 nm / sec) of 2-[3-{2-(4,6-dimethylpyrimidyl)}-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (ETL-1) and Liq were formed in a 50:50 (mass ratio) ratio in the electron transport layer 6 instead of compound (A-1). ETL-1 was synthesized by the method described in Synthesis Example 27 of JP 2015-027986 A.

[0184] A direct current was applied to the produced organic electroluminescent device, and the light-emitting characteristics were evaluated according to the method described above for measuring light-emitting characteristics.

[0185] The light-emitting characteristics are as follows: current density 10mA / cm 2 The voltage (V) and power efficiency (lm / A) were measured when current was applied, and the device lifespan during continuous lighting was measured. The device lifespan was measured when the initial luminance was 1000 cd / m 2 The luminance decay time was measured during continuous lighting when driven at 1000 Hz, and the luminance (cd / m 2 The time (hr) required for the electrical conductivity to decrease by 5% was measured. The voltage (V), power efficiency (lm / A) and lifespan values ​​were expressed as relative values ​​with the value of Reference Example Element-1 taken as 100. The results are shown in Table 1.

[0186] [Table 1]

[0187] From Table 1, it was found that the organic electroluminescent device using the triazine compound (1) can achieve higher levels of voltage, luminous efficiency, and device life, compared to the reference example. [Industrial Applicability]

[0188] The present invention can be used for organic electroluminescent devices that exhibit high luminous efficiency and long life characteristics. In addition to organic electroluminescent devices, the present invention can also be suitably used as an electron transport material in organic transistors. [Explanation of symbols]

[0189] 1. Substrate 2.Anode 3. Hole injection layer 4. Hole transport layer 41.First hole transport layer 42.Second hole transport layer 5. Emitting layer 6.Electron transport layer 7.Electron injection layer 8.Cathode 9. Hole-blocking layer 100. Organic electroluminescent device

Claims

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

2. R １ , R ２ , R ３ , and R ４ Among these, R other than alkyl groups having 1 to 18 carbon atoms １ , R ２ , R ３ , and R ４ 2. The alkyltriazine compound according to claim 1, wherein is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, a phenyl group, a pyridyl group, or a cyano group.

3. 3. The alkyltriazine compound according to claim 1, wherein L is a divalent aromatic hydrocarbon group consisting of only six-membered rings.

4. The alkyltriazine compound according to any one of claims 1 to 3, wherein p is 0 or 1.

5. The alkyltriazine compound according to any one of claims 1 to 4, wherein p is 0.

6. R ５ 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 which consists solely of a 6-membered ring which may be substituted with a cyano group; or Si(Ar) ３ The alkyltriazine compound according to any one of claims 1 to 5, wherein the silyl group is represented by the formula:

7. 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 11 carbon atoms which consists of only one or more 6-membered rings which may be substituted with a cyano group; or a triphenylsilyl group.

8. 8. The alkyltriazine compound according to claim 1, wherein q is 1.

9. R １ , R ２ , R ３ and R ４ At least one of R is an alkyl group having 1 to 6 carbon atoms, and the remaining R １ , R ２ , R ３ and R ４ and each represent an aromatic hydrocarbon group having 6 to 18 carbon atoms.

10. R １ , R ２ , R ３ and R ４ At least one of the R １ , R ２ , R ３ and R ４ and each represent an aromatic hydrocarbon group having 6 to 12 carbon atoms.

11. The alkyltriazine compound according to claim 1, represented by any one of the following formulas A-6 to A-8. 【Chemistry 2】

12. A material for an organic electroluminescent device, comprising the alkyltriazine compound according to claim 1 .

13. An electron transport material for an organic electroluminescent device, comprising the alkyltriazine compound according to claim 1 .

14. An organic electroluminescent device comprising the alkyltriazine compound according to claim 1 .

Images