Triazine compounds having a xanthenyl group

Abstract

To provide a triazine compound that contributes to making an organic electroluminescent device that can exhibit an excellent service life, a material for organic electroluminescent devices and a method for producing the triazine compound.SOLUTION: The present invention discloses a triazine compound having a specific structure represented by formula (1).SELECTED DRAWING: Figure 2

Description

[Technical field]

[0001] The present disclosure relates to a triazine compound, a method for producing the same, and a material for an organic electroluminescent device. [Background technology]

[0002] Organic electroluminescent devices have started to be put to practical use, mainly for small mobile devices. Although recent organic electroluminescent devices have been gradually improved, further performance improvements are required. In particular, there is a strong demand for longer life from the viewpoint of expanding the range of applications of organic electroluminescent devices. Moreover, organic electroluminescent devices are beginning to be put to practical use in applications other than small mobile applications, for example, as in-vehicle display devices.

[0003] Here, Patent Document 1 discloses a triazine compound having a specific structure as an electron transport material. According to Patent Document 1, the triazine compound can provide an organic electroluminescent device excellent in life, voltage, or luminous efficiency. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent No. 6464944 Summary of the Invention [Problem to be solved by the invention]

[0005] However, there is a very strong demand from the market for an expansion of applications, and the triazine compound of Patent Document 1 does not sufficiently meet these demands in terms of extending the device life, so further improvement is required.

[0006] Therefore, one aspect of the present invention is directed to providing a triazine compound and a material for an organic electroluminescent element that contribute to the production of an organic electroluminescent element that can exhibit an excellent element life, as well as a method for producing the triazine compound. Another aspect of the present invention is directed to providing an organic electroluminescent device that can exhibit an excellent device life. [Means for solving the problem]

[0007] The triazine compound according to one embodiment of the present disclosure is represented by formula (1):

[0008] [ka]

[0009] During the ceremony, Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar 1 and Ar 2 each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R 2 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; The Two R's 2 may together with the carbon atom to which it is attached form a 5- or 6-membered ring; R 3are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Two adjacent R 3 may be taken together with the carbon atom to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; When p is 2, the two L's may be different from each other.

[0010] A method for producing a triazine compound represented by formula (1) according to another embodiment of the present disclosure includes coupling a compound represented by formula (2) with a compound represented by formula (3):

[0011] [ka]

[0012] During the ceremony, Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar 1 and Ar 2 each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R2 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; The Two R's 2 may together with the carbon atom to which it is attached form a 5- or 6-membered ring; R 3 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Two adjacent R 3 may be taken together with the carbon atoms to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; M 1 ZnY 1 , MgY 2 , Sn(Y 3 ) 3 , or B(OY 4 ) 2 Represents; Y 1 and Y 2 each independently represents a chlorine atom, a bromine atom, or an iodine atom; Y 3 each independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group; Y 4 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; Two (OY 4 ) groups may together form a ring with the boron atom; X1 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom.

[0013] A method for producing a triazine compound represented by formula (1) according to another embodiment of the present disclosure includes coupling a compound represented by formula (4) with a compound represented by formula (5):

[0014] [ka]

[0015] During the ceremony, Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar 1 and Ar 2 each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R 2 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Also, two R 2 may together with the carbon atom to which it is attached form a 5- or 6-membered ring; R 3 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Two adjacent R 3 may be taken together with the carbon atoms to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; X 2 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom; M 2 ZnY 1 , MgY 2 , Sn(Y 3 ) 3 , or B(OY 4 ) 2 Represents; Y 1 and Y 2 each independently represents a chlorine atom, a bromine atom, or an iodine atom; Y 3 each independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group; Y 4 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; Two (OY 4 ) groups may be joined together to form a ring with the boron atom.

[0016] A material for organic electroluminescent devices according to another embodiment of the present disclosure contains the above-mentioned triazine compound. An organic electroluminescent device according to another embodiment of the present disclosure contains the above-mentioned triazine compound. Effect of the Invention

[0017] According to one aspect of the present disclosure, it is possible to provide a triazine compound and a material for an organic electroluminescent element that contribute to the production of an organic electroluminescent element that achieves an excellent element life, as well as a method for producing the triazine compound. According to another aspect of the present disclosure, it is possible to provide an organic electroluminescent device that achieves an excellent device life. [Brief description of the drawings]

[0018] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescence element according to one embodiment of the present disclosure. [Diagram 2] FIG. 2 is a schematic cross-sectional view showing another example of a laminate structure (structure of Element Example 1) of an organic electroluminescence element according to one embodiment of the present disclosure. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] The triazine compound according to one embodiment of the present disclosure will be described in detail below. The triazine compound according to one embodiment of the present disclosure is represented by formula (1):

[0020] [ka]

[0021] During the ceremony, Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar 1 and Ar 2 each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R 2 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; The Two R's 2 may together with the carbon atom to which it is attached form a 5- or 6-membered ring; R 3 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Two adjacent R 3 may be taken together with the carbon atom to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; When p is 2, the two L's may be different from each other.

[0022] The inventors speculate that the above-mentioned problems can be solved by introducing a xanthenyl group into an appropriate position in the molecule of a triazine compound having a structure as shown in formula (1), thereby improving durability against holes.

[0023] Hereinafter, the triazine compound according to one embodiment of the present disclosure (hereinafter, also simply referred to as triazine compound (1)) will be described in more detail. The triazine compound (1) is represented by any one of formulas (1a), (1b), (1c), or (1d).

[0024] [ka]

[0025] In formulas (1a) to (1d), Ar 1 , Ar 2 , R 1 , R 2 , R 3 The definitions of L, Z and p are the same as those in formula (1).

[0026] In terms of ease of synthesis of the triazine compound (1), the compound represented by formula (1a) is preferred. Ar in triazine compound (1) 1 , Ar 2 , R 1 , R 2 , R 3 , L, Z and p are defined as follows.

[0027] [Ar 1 , Ar 2 About Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group. 1 and Ar 2 may each independently be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group. The triazine compound (1) has excellent electron transport properties, and therefore Ar 1 and Ar 2 are each preferably independently a phenyl group or a biphenylyl group. In addition, the triazine compound (1) is easy to synthesize, and Ar 1 and Ar 2 are preferably the same group.

[0028] [R 1 About R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or It represents a nitrogen-containing heterocyclic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. R 1 but, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or It is preferably a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.

[0029] Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, and a fluoranthenyl group. 1 is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms, more preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthrenyl group, and particularly preferably a phenyl group or a biphenylyl group.

[0030] Nitrogen-containing heterocyclic group Examples of the nitrogen-containing heterocycle include a pyridyl group, a piperidyl group, a benzo[b]quinolyl group, a phenylpyridyl group, and a carbazolyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In that the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance, R 1 is preferably a pyridyl group, a dimethylpyridyl group, or a phenylpyridyl group.

[0031] [R 2 About R 2are the same or different, Hydrogen atom an alkyl group having 1 to 6 carbon atoms, or It represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. R 2 At least one of these is preferably an alkyl group having 1 to 6 carbon atoms.

[0032] Alkyl group The alkyl group having 1 to 6 carbon atoms may be, for example, a linear, branched, or cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, and a cyclobutyl group. 2 is preferably a methyl group.

[0033] Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, and a fluorenyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In terms of easiness in the synthesis of the triazine compound (1), R 2 is preferably an unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms substituted with a methyl group, and a phenyl group is particularly preferred.

[0034] Also, two R 2may form a 5- or 6-membered ring together with the carbon atom to which it is bonded. Examples of the 5- or 6-membered ring include cyclopentane, cyclopentene, cyclopentadiene, cyclohexyl, cyclohexene, and 1,4-cyclohexadiene. In terms of ease of synthesis of the triazine compound (1), it is preferable that the 5- or 6-membered ring is cyclopentane or cyclohexane.

[0035] [R 3 About R 3 are the same or different, Hydrogen atom an alkyl group having 1 to 6 carbon atoms, or It represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. R 3 are the same or different, A hydrogen atom, or An alkyl group having 1 to 6 carbon atoms is preferred.

[0036] Alkyl group The alkyl group having 1 to 6 carbon atoms may be, for example, a linear, branched, or cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, and a cyclobutyl group. 3 is preferably a methyl group.

[0037] Aromatic Hydrocarbon Group Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, an anthryl group, and a fluorenyl group. These groups may be substituted with an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be any of a linear, branched, and cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a 2-methylpropyl group, an isopropyl group, a cyclopropyl group, a butyl group, a 2-butyl group, and a tert-butyl group. In terms of easiness in the synthesis of the triazine compound (1), R 3 is preferably a phenyl group.

[0038] Also, two R 3 may form a 5- or 6-membered ring together with the carbon atom to which it is bonded. Examples of the 5- or 6-membered ring include cyclopentane, cyclopentene, cyclopentadiene, cyclohexyl, cyclohexene, cyclohexadiene, and benzene. In terms of ease of synthesis of triazine compound (1), it is preferable that the 5- or 6-membered ring is cyclopentane or benzene.

[0039] [About Z] Z represents an oxygen atom or a sulfur atom. Z is preferably an oxygen atom in that the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance.

[0040] [About L] L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms. Examples of the phenylene group include an ortho-phenylene group, a meta-phenylene group, and a para-phenylene group. In order to contribute to the formation of a high-performance organic electroluminescent device from the triazine compound (1), it is preferable that L is a meta-phenylene group or a para-phenylene group which may be substituted with a phenyl group, a naphthyl group, or an alkyl group having 1 to 4 carbon atoms.

[0041] [About p] p represents 0, 1 or 2; When p is 2, the two L's may be different from each other. p is preferably 0 or 1, since the triazine compound (1) contributes to the formation of an organic electroluminescent device with higher performance.

[0042] [Specific examples of triazine compound (1)] Specific examples of the triazine compound (1) are not particularly limited, but include compounds having structures represented by the following formulas (1-1) to (1-165).

[0043] [ka]

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] Next, a method for producing a triazine compound according to another embodiment of the present disclosure (hereinafter, referred to as a method for producing a triazine compound (1)) will be described. The triazine compound (1) can be produced by step 1 or 2 shown in the following reaction scheme. That is, the method for producing the triazine compound (1) is as follows: or comprising subjecting a compound represented by formula (2) and a compound represented by formula (3) to a coupling reaction. The method includes subjecting a compound represented by formula (4) and a compound represented by formula (5) to a coupling reaction.

[0055] [ka]

[0056] [ka]

[0057] During the ceremony, Ar 1 and Ar 2 each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar 1 and Ar 2each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R 1 teeth, Hydrogen atoms, A monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms, or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R 2 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Also, two R 2 may together with the carbon atom to which it is attached form a 5- or 6-membered ring; R 3 are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; Two adjacent R 3 may be taken together with the carbon atoms to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; When p is 2, the two L's may be different from each other. M 1 ZnY 1 , MgY 2 , Sn(Y 3 ) 3 , or B(OY 4 ) 2 Represents; M 2 ZnY 1 , MgY 2 , Sn(Y 3 ) 3 , or B(OY 4 ) 2 Represents; Y 1 and Y 2 each independently represents a chlorine atom, a bromine atom, or an iodine atom; Y 3 each independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group; Y 4 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; X 1 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom; X 2 represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom; Two (OY 4 ) groups may be taken together to form a ring with the boron atom. M 1 or M 2 But B(OY 4 ) 2 It is preferable that:

[0058] Step 1 is a step of producing triazine compound (1) by coupling reaction of triazine compound (2) with compound (3) in the presence of a catalyst as necessary. In step 1, the target product can be obtained in good yield by applying reaction conditions for general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc. When the reaction conditions for Suzuki-Miyaura reaction are applied to step 1, it is preferable to carry out the reaction in the presence of a base. In addition, a palladium catalyst is preferable as the catalyst.

[0059] The compound represented by formula (2) used in step 1 can be synthesized, for example, by the method disclosed in Japanese Patent No. 5312824, or by a reaction for synthesizing a general organometallic compound from a compound represented by formula (4) (see, for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363). Examples of the compound represented by formula (2) include compounds having structures shown in the following formulas (2-1) to (2-95), but the present invention is not limited thereto. In formulas (2-1) to (2-95), M 1 has the same definition as in equation (2).

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] M 1 The group represented by the formula (I) is not particularly limited, but may be, for example, ZnY 1 , MgY 2 , Sn(Y 3 ) 3 Or, two (OY 4 ) groups may be taken together to form a ring with the boron atom; 4 ) 2 Among these, B(OY 4 ) 2 is preferred.

[0069] ZnY 1 , MgY 2 Although there is no particular limitation to the above, examples of the oxide include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI. Sn(Y 3 ) 3 is not particularly limited, but for example, Sn(Me) 3 , Sn(Bu) 3 Examples include: B(OY 4 ) 2 is not particularly limited, but may be, for example, B(OH) 2 , B(OMe) 2 , B(O i Pr) 2 , B(OBu) 2 , B(OPh) 2 Me is a methyl group, i Pr is an isopropyl group, Bu is a butyl group, and Ph is a phenyl group. 4 ) groups together with the boron atom form a ring, 4 ) 2 Examples of the group are not particularly limited, but include the following groups represented by (I) to (VI), with the group represented by (II) being preferred in terms of good yield.

[0070] [ka]

[0071] The compound (3) used in step 1 can be produced, for example, according to the method of Japanese Patent No. 6023635. Alternatively, a commercially available product may be used. Examples of the compound (3) include the following formulas (3-1) to (3-12), but the present invention is not limited thereto. In the formulas (3-1) to (3-12), X 1 has the same definition as equation (3).

[0072] [ka]

[0073] X 1 The leaving group represented by is not particularly limited, but examples thereof include a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, and an iodine atom, and a chlorine atom or a bromine atom is preferred in terms of a good yield of the triazine compound (1). However, in terms of the availability of raw materials, it may be preferable to use a trifluoromethanesulfonyloxy group.

[0074] The palladium catalyst that can be used in step 1 is not particularly limited, but specifically includes Palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate; Complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, and dichlorobis(benzonitrile)palladium; and Palladium complexes having a tertiary phosphine as a ligand, such as dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, and dichlorobis(tricyclohexylphosphine)palladium; Examples include:

[0075] Palladium complexes having a tertiary phosphine as a ligand can also be prepared in the reaction system by adding a tertiary phosphine to a palladium salt or complex compound. Examples of tertiary phosphines that can be used in this case include triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, bis(diphenylphosphine), and tertiary phosphino. Examples of the 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine include 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine, and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl phosphine.

[0076] Among these, palladium complexes having a tertiary phosphine as a ligand are preferred in terms of good yield, and palladium complexes having 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or triphenylphosphine as a ligand are more preferred.

[0077] 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 the palladium catalyst used in step 1, 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 equivalent to the boron compound.

[0078] The base used in step 1 is not particularly limited, but examples thereof include metal hydroxide salts such as sodium hydroxide, potassium hydroxide, and calcium hydroxide; metal carbonate salts such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate; metal acetate salts such as potassium acetate and sodium acetate; metal phosphate salts 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 and metal phosphates are preferred in terms of good reaction yield, and potassium carbonate or potassium phosphate is more preferred. There is no particular limit to the amount of base, but in terms of good reaction yield, the molar ratio of the base to the boron compound is preferably in the range of 1:2 to 10:1, and more preferably in the range of 1:1 to 4:1.

[0079] Step 1 can be carried out in a solvent, and examples of the solvent include water; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone. Examples of the solvent include esters such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU), N,N'-dimethylpropyleneurea (DMPU); and alcohols such as dimethylsulfoxide (DMSO), methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and the like, which may be mixed in any ratio. There is no particular limit to the amount of the solvent used. Among these, water, ether, amide, alcohol, or a mixed solvent thereof is preferred in terms of good reaction yield, and a mixed solvent of THF and water is more preferred.

[0080] Step 1 can be carried out at a temperature appropriately selected from 0° C. to 200° C., and is preferably carried out at a temperature appropriately selected from 40° C. to 150° C. in terms of good reaction yield. The product of step 1 can be obtained by carrying out a normal treatment after completion of the reaction. If necessary, it may be purified by recrystallization, column chromatography, sublimation, preparative HPLC, or the like.

[0081] Next, step 2 will be described. Step 2 is a step of producing triazine compound (1) by coupling reaction of compound (4) and compound (5) represented by formula (5) in the presence of a catalyst as necessary. In step 2, the target product can be obtained in good yield by applying reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc. When reaction conditions of Suzuki-Miyaura reaction are applied to step 2, it is preferable to carry out the reaction in the presence of a base. In addition, a palladium catalyst is preferable as the catalyst.

[0082] The triazine compound represented by formula (4) used in step 2 can be produced, for example, according to the method disclosed in JP 2018 / 115151 A. The triazine compound represented by formula (4) is a specific example of the compound represented by formula (2), which is represented by M 1 , X 2 Here, compounds in which X is replaced with 2 is synonymous with equation (4).

[0083] X 2 The leaving group represented by the formula (I) is not particularly limited, but examples thereof include a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, and an iodine atom. From the viewpoint of a good yield of the triazine compound (1), a chlorine atom or a bromine atom is preferred.

[0084] The compound represented by formula (5) used in step 2 can be produced, for example, according to U.S. Patent Publication No. 2014 / 0239279. Alternatively, it can be synthesized from the compound represented by formula (3) using a general reaction for synthesizing an organometallic compound (for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363), or a commercially available product may be used.

[0085] The compound represented by formula (5) is X in the compounds represented by formulas (3-1) to (3-12). 1 M 2 An example of a skeleton in which M is replaced with 2has the same definition as equation (5).

[0086] The palladium catalyst, base, solvent, reaction temperature, and post-treatment (purification) that can be used in step 2 are the same as those exemplified in step 1, and the preferred configurations thereof are also the same.

[0087] The triazine compound (1) can be used for, for example, organic electronic devices such as organic electroluminescent devices and photoelectric devices, etc. Among these, the triazine compound (1) is preferably used as a material for organic electroluminescent devices.

[0088] <Materials for organic electroluminescence devices> The material for organic electroluminescent devices according to one embodiment of the present disclosure contains the above-mentioned triazine compound (1). The triazine compound (1) can be used, for example, as an electron transport material for organic electroluminescence devices. The material for organic electroluminescence devices containing the triazine compound (1) contributes to the production of organic electroluminescence devices that can achieve high levels of luminous efficiency and life span.

[0089] <Organic electroluminescent device> The material for organic electroluminescent devices according to one embodiment of the present disclosure contains the above-mentioned triazine compound (1).

[0090] <Organic electroluminescent device> An organic electroluminescent device containing a triazine compound (1) (hereinafter, may be simply referred to as an organic electroluminescent device) will be described below. The organic electroluminescent device according to one embodiment of the present disclosure contains a triazine compound (1). The configuration of the organic electroluminescent device is not particularly limited, but examples thereof include the following configurations (i) to (v). (i): Anode / 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

[0091] The triazine 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 terms of excellent light-emitting properties of the organic electroluminescent device. Therefore, in the case of the structures shown in (i) to (v) above, the triazine compound (1) is preferably contained in one or more layers selected from the group consisting of the light-emitting layer, the electron transport layer, and the electron injection layer.

[0092] Hereinafter, an organic electroluminescent device according to one embodiment of the present disclosure will be described in more detail with reference to FIG. 1, taking the above configuration (v) as an example. 1 has a so-called bottom-emission type element configuration, the organic 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.

[0093] FIG. 1 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device including a triazine compound according to one embodiment of the present disclosure.

[0094] The organic electroluminescent device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 in this order. However, some of these layers may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the light emitting layer 5 and the electron transport layer 6, or the hole injection layer 3 may be omitted and the hole transport layer 4 may be provided directly on the anode 2. Alternatively, a single layer having the functions of the multiple layers, such as an electron injection / transport layer having the functions of both the electron injection layer and the electron transport layer in a single layer, may be provided instead of the multiple layers. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be made up of multiple layers.

[0095] <<Layer Containing Triazine Compound (1)>> 1, the organic electroluminescent device 100 contains a triazine compound (1) in one or more layers selected from the group consisting of a light-emitting layer 5, an electron transport layer 6, and an electron injection layer 7. In particular, it is preferable that the electron transport layer 6 contains the triazine compound (1). The triazine compound (1) may be contained in multiple layers of the organic electroluminescent device. In the following, an organic electroluminescent device 100 in which the electron transport layer 6 contains the triazine compound (1) will be described.

[0096] [Substrate 1] The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate. Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, a plastic film, etc. Among these, a glass plate, a quartz plate, and a light-transmitting plastic film are preferable. Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), etc. 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.

[0097] [Anode 2] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side). Examples of the anode material include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (e.g., 4 eV or more). Specific examples of the anode material include metals such as Au; CuI, indium tin oxide (ITO), SnO 2 , ZnO and other conductive transparent materials. In the case of an organic electroluminescent device in which light is extracted through the anode, the anode is formed of a conductive transparent material that is transparent or substantially transparent to the emitted light.

[0098] [Hole injection layer 3, hole transport layer 4] Between the anode 2 and a light-emitting layer 5 described below, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side.

[0099] 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 this 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.

[0100] The hole injection layer and the hole transport layer also function as electron barrier layers. That is, the electrons injected from the cathode and transported to the light emitting layer from the electron injection layer and / or the electron transport layer are prevented from leaking to the hole injection layer and / or the hole transport layer due to the barrier of electrons present at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons are accumulated at the interface in the light emitting layer, which brings about effects such as improved light emitting efficiency, and an organic electroluminescent device with excellent light emitting performance is obtained.

[0101] The material for the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property. The material for the hole injection layer and the hole transport layer may be either an organic material or an inorganic material.

[0102] 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-based 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 in terms of the good performance of the organic electroluminescent device, and aromatic tertiary amine compounds are particularly preferred.

[0103] Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Examples of such compounds include di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA).

[0104] 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.

[0105] 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.

[0106] [Light-emitting layer 5] The light-emitting layer 5 is provided between the hole transport layer 4 and the electron transport layer 6 described below. Examples of materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs are recombined, resulting in light emission.

[0107] The light-emitting layer may consist of a single small molecule or single polymeric material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from the dopant and can be of any color.

[0108] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, examples of the compound include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like.

[0109] Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium, thiapyrylium compound, fluorene derivative, periflanthene derivative, indenoperylene derivative, bis(azinyl)amine boron compound, bis(azinyl)methane compound, carbostyril compound, etc. The fluorescent dopant may be a combination of two or more selected from these.

[0110] Phosphorescent dopants include, for example, organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0111] 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))).

[0112] In addition, 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.

[0113] 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 composition or different compositions.

[0114] [Electron transport layer 6] An electron transport layer 6 is provided between the light emitting layer 5 and an electron injection layer 7 described below. The electron transport layer has a function of transporting electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

[0115] As described above, the electron transport layer preferably contains the triazine compound (1). In addition to the triazine compound (1), the electron transport layer may further contain one or more types selected from conventionally known electron transport materials. When the triazine compound (1) is not contained in the electron transport layer but is contained in another layer, one or more types selected from conventionally known electron transport materials can be used as the electron transport material constituting the electron transport layer.

[0116] Examples of 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-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, and tris(8-hydroxyquinolinato). Examples of such compounds include gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolate)gallium, bis(2-methyl-8-quinolinato)-1-naphtholate aluminum, and bis(2-methyl-8-quinolinato)-2-naphtholate gallium.

[0117] The electron transport layer may have a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions.

[0118] In the organic electroluminescent device according to this embodiment, an electron injection layer may be provided for the purpose of improving the electron injection property and improving the device characteristics (for example, luminous efficiency, constant voltage driving, or high durability).

[0119] [Electron injection layer 7] Between the electron transport layer 6 and a cathode 8 described below, an electron injection layer 7 is provided. The electron injection layer has a function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[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, fluorenylidene methane, anthraquinodimethane, and anthrone. Examples of materials for the electron injection layer include SiO 2 Also included are inorganic compounds such as various oxides, nitrides, and oxynitrides, such as 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 . In the case of an organic electroluminescence element having a configuration in which only light emitted through the anode is extracted, the cathode can be formed from any conductive material. Examples of materials for the cathode include metals with a small work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, the metals with a small work function are, for example, metals with a work function of 4 eV or less. Specific examples of cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, and aluminum / aluminum oxide (Al 2 O 3 ) mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc. Among these, from the viewpoints of electron injection property and durability against oxidation, etc., mixtures of an electron injection metal and a second metal which is a metal having a larger and more stable work function than the electron injection metal, such as magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, and aluminum / aluminum oxide (Al 2 O 3 ) mixture, lithium / aluminum mixture, etc. are preferred.

[0122] [How each layer is formed] Each layer except for the electrodes (anode, cathode) described above can be formed into a thin film by a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. The material of each layer may be used alone or, if necessary, together with a material such as a binder resin or a solvent. There are no particular limitations on the film thickness of each layer thus formed, and it can be appropriately selected depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0123] The anode and cathode can be formed by forming a thin film of an electrode material by a method such as vapor deposition, sputtering, etc. A pattern may be formed through a mask having a desired shape during vapor deposition or sputtering, or a pattern having a desired shape may be formed by photolithography after forming a thin film by vapor deposition, sputtering, etc.

[0124] The film thickness of the anode and cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0125] In addition, when forming a layer containing the triazine compound (1), it may be used in combination with the above-mentioned conventionally known electron transporting material. Thus, for example, the triazine 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 triazine compound (1).

[0126] The organic electroluminescent element may be used as a kind of lamp for illumination or exposure light source, or as a projection device for projecting an image onto a screen or the like, or as a display device for directly viewing still images or moving images. When using an organic electroluminescent element as a display device for playing moving images, the driving method may be a simple matrix (passive matrix) method or an active matrix method. In addition, a full-color display device can be produced by using two or more kinds of organic electroluminescent elements having different emission colors.

[0127] When used as an electron transport layer, triazine compound (1) can provide an organic electroluminescent device having significantly superior luminous efficiency and long life characteristics compared to conventionally known triazine compounds. Furthermore, triazine compound (1) has high amorphousness and high film quality stability due to its steric hindrance skeleton. This provides effects such as improved driving stability and improved luminous efficiency of organic electroluminescent devices. Furthermore, triazine compound (1) has high chemical stability due to its characteristic skeleton, and can contribute to the long life of organic electroluminescent devices.

[0128] The triazine compound (1) can be used as an electron transport layer of an organic electroluminescent device to provide a triazine compound capable of achieving low-voltage driving, high efficiency, and long life of the device at a high level. Furthermore, an organic electroluminescent device using the triazine compound (1) can be provided that can achieve low-voltage driving, high efficiency, and long life. EXAMPLES

[0129] 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.

[0130] [ 1 H-NMR measurement] 1 For H-NMR measurements, a Bruker ASCEND 400 (400 MHz; manufactured by BRUKER) was used. 1H-NMR was performed using deuterated chloroform (CDCl 3 ) was used as the measurement solvent, and tetramethylsilane (TMS) was used as the internal standard.

[0131] [Luminescence property measurement] The light-emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the device prepared in each Example (described later) in a 25° C. environment using a luminance meter BM-9 (product name, manufactured by Topcon Technohouse Corporation). The reagents used were commercially available.

[0132] Synthesis Example 1 [ka]

[0133] Under an argon atmosphere, 2-{3-(2-biphenylyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-4,6-diphenyl-1,3,5-triazine (7.24 g), 3-bromo-9,9-dimethylxanthene (2.54 g), palladium acetate (59 mg), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (252 mg) were suspended in THF (90 mL). 2.0 M potassium carbonate aqueous solution (13 mL) was added to this suspension, and the mixture was heated to reflux for 24 hours. After cooling, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (toluene) to obtain the desired 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine (compound 1-2) (4.31 g, 73%).

[0134] 1 HNMR(CDCl 3)δ1.66(s,6H),7.06-7.13(m,3H),7.20-7.24(m,2H),7.27-7.37(m,6H),7.44-7.46(m,2H),7.50 -7.65(m,9H),7.69-7.72(m,1H),8.73(t,J=1.6Hz,1H),8.76-8.80(m,4H),8.81(t,J=1.6Hz,1H).

[0135] Synthesis Example 2 [ka]

[0136] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (4.00 g, 7.8 mmol), tris(dibenzylideneacetone)dipalladium (108 mg, 0.12 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (200 mg, 0.47 mmol), and 2M-tripotassium phosphate (12 mL, 24 mmol) were suspended in THF (68 mL). Further, a mixture of 3-bromo-9,9-dimethyl-9H-xanthene and 9,9-dimethyl-9H-xanthene (5.30 g, 3-bromo-9,9-dimethyl-9H-xanthene:9,9-dimethyl-9H-xanthene=55:45) dissolved in THF (10 mL) was added dropwise. Then, this reaction mixture was stirred at 80°C for 16 hours. After cooling to room temperature, chloroform (150 mL) was added to the reaction mixture to extract the organic layer, which was then washed with water and then with saturated saline. Sodium sulfate and activated carbon were added to the extract and stirred at room temperature for a while, followed by filtration through Celite, and low boiling points were distilled off from the filtrate under reduced pressure. The obtained solid was recrystallized from toluene (115°C, 5 mL) to obtain the desired 2-[3-(9,9-dimethyl-9H-xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-14) as a white solid (yield 2.9 g, 62%).

[0137] 1H-NMR (CDCl 3 )δ(ppm):9.05(t,J=1.6Hz,1H),8.79-8.82(m,5H),7.89-7.92(m,2H),7.67-7.73(m,3H),7.52-7.66(m,9H),7 .45(dd,J=7.7,1.6Hz,1H),7.22(dd,J=7.9,1.7Hz,1H),7.12(d,J=8.4Hz,1H),7.08-7.13(m,2H),1.73(s,6H).

[0138] Synthesis Example 3 [ka]

[0139] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-terphenyl-3-yl]-1,3,5-triazine (3.90 g, 6.6 mmol), 3-bromo-9,9-dimethyl-9H-thioxanthene (2.43 g, 8.0 mmol), palladium acetate (75 mg, 0.33 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (316 mg, 0.66 mmol) were suspended in THF (66 mL). 2M potassium phosphate aqueous solution (10 mL, 20 mmol) was added to this suspension, and the mixture was heated to reflux for 18 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 110°C for a while, then filtered through Celite, and low boiling points were distilled off from the filtrate under reduced pressure. The obtained solid was purified by recrystallization (toluene) to obtain the desired 2-[5-(9,9-dimethyl-9H-thioxanthen-3-yl)-1,1':2',1''-terphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-77) (yield: 2.81 g, 62%).

[0140] 1 H-NMR (CDCl 3)δ(ppm):8.81(t,J=1.6Hz,1H),8.73-8.78(m,4H),8.71(t,J=1.6Hz,1H) ,7.64-7.70(m,1H),7.44-7.70(m,14H),7.18-7.34(m,8H),1.71(s,6H).

[0141] Synthesis Example 4 [ka]

[0142] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (64.6 mg, 0.13 mmol), 3-bromo-9-methyl-9-phenyl-9H-xanthene (42.6 mg, 0.14 mmol), palladium acetate (1.6 mg, 6.9 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (6.6 mg, 14 μmol) were suspended in THF (1.4 mL). 2M potassium phosphate aqueous solution (0.2 mL, 0.44 mmol) was added to this suspension, and the mixture was heated to reflux for 18 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 110°C for a while, then filtered through Celite, and low boiling points were distilled off from the filtrate under reduced pressure. The obtained solid was purified by column chromatography (hexane / chloroform), and then washed with hexane to obtain the desired 2-[3-(9-methyl-9-phenyl-9H-xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-152) (yield: 58.6 mg, 71%).

[0143] 1 H-NMR (CDCl 3)δ(ppm):8.96(s,1H),8.76-8.82(m,5H),7.81(d,J=7.7Hz,1H),7.73(s,1H),7.56-7.69(m,8H),7.48-7.54(m,2H),7.43(d,J=7.7Hz,1H), 7.37(d,J=7.4Hz,2H),7.28(d,J=7.4Hz,2H),7.12-7.24(m,5H),6.96(td,J=7.4Hz,1.1Hz,1H),6.89(dd,J=7.8Hz,1.5Hz,1H),2.02(s,3H).

[0144] Synthesis Example 5 [ka]

[0145] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1':2',1''-terphenyl-3-yl]-1,3,5-triazine (32 mg, 54 μmol), 2'-chloro-spiro[cyclohexane-1,9'-[9H]thioxanthene] (17 mg, 57 μmol), palladium acetate (0.4 mg, 1.6 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.5 mg, 3.2 μmol) were suspended in THF (0.54 mL). 2M potassium phosphate aqueous solution (0.32 mL, 0.16 mmol) was added to this suspension, and the mixture was heated to reflux for 22 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (hexane:ethyl acetate=98:2) and preparative thin layer chromatography (hexane:ethyl acetate=9:1) to obtain the desired 2-[5-spiro[cyclohexane-1,9'-[9H]thioxanthen]-3-yl)-1,1':2',1''-terphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-160) (yield 4.2 mg, 10%).

[0146] 1 H-NMR (CDCl3 )δ(ppm):8.86(dd,J=1.7,1.6Hz,1H),8.75-8.77(m,4H),8.70(dd,J=1.6,1.6Hz,1H),7.67-7.69(m ,1H),7.47-7.66(m,14H),7.15-7.32(m,8H),2.29-2.41(m,4H),1.72(brs,4H),0.83-0.90(m,2H).

[0147] Synthesis Example 6 [ka]

[0148] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3'-yl]-1,3,5-triazine (100 mg, 0.20 mmol), 3-chloro-7H-benzo[c]xanthene (57.3 mg, 0.22 mmol), palladium acetate (2.2 mg, 9.8 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (9.3 mg, 20 μmol) were suspended in THF (2.0 mL). 2M potassium phosphate aqueous solution (0.3 mL, 0.59 mmol) was added to this suspension, and the mixture was heated to reflux for 16 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform and filtered through a silica gel pad (hexane:chloroform = 1:1). The low boiling points were removed from the filtrate by distillation under reduced pressure to obtain the desired 2-[3-(7H-benzo[c]xanthen-3-yl)biphenyl-3'-yl]-4,6-diphenyl-1,3,5-triazine (compound 1-158) (yield: 43.0 mg, 35%).

[0149] 1 H-NMR (CDCl 3)δ(ppm):9.05(dd,J=1.7Hz,2.0Hz,1H),8.76-8.82(m,5H),8.42(d,J=8.2Hz,1H),7.94(dd,J=1.7Hz,2.0Hz,1H), 7.90(m,1H),7.82(d,J=8.1Hz,1H)7.46-7.75(m,15H),7.34(d,J=8.3Hz,1H),7.28(d,J=8.3Hz,1H),4.31(s,2H).

[0150] Reference example-1 [ka]

[0151] Under a nitrogen atmosphere, 2-[3-chloro-5-(phenanthren-9-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (1.00 g, 1.9 mmol), phenylboronic acid (282 mg, 2.3 mmol), palladium acetate (13.0 mg, 0.06 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 55.0 mg, 0.12 mmol), 1,4-dioxane (50 mL) and 2M-tripotassium phosphate aqueous solution (2.9 mL, 5.8 mmol) were added to a 300 mL four-neck flask and stirred at 95 ° C for 6 hours. After the obtained reaction solution was cooled to room temperature, water (100 mL) was added to the reaction mixture, and the precipitate was collected by filtration and washed with water, methanol, and then hexane to obtain a gray powder. The resulting gray powder was purified by recrystallization from toluene to obtain the target product, 4,6-diphenyl-2-[5-(phenanthren-9-yl)-biphenyl-3-yl]-1,3,5-triazine (compound ETL-1), as a gray powder (yield 700 mg, 65%).

[0152] 1 H-NMR (CDCl 3):δ9.12(t,J=1.7Hz,1H)8.93(t,J=1.7Hz,1H),8.85(d,J=8.3Hz,1H),8.77-8.80(m,5H),8.01-8.04(m,2H),7.98(dd,J=7.8Hz,1.4Hz,1H) ,7.88(s,1H),7.84(dd,J=8.1Hz,1.0Hz,2H),7.73(t,J=7.8Hz,1.3Hz,2H),7.67(t,J=7.2Hz,1H),7.52-7.63(m,9H),7.45(t,J=7.3Hz,1H).

[0153] Next, the obtained compound was used to carry out element evaluation. Element Example 1 (see Figure 2)

[0154] (Prepare 1 substrate and 2 anodes) A glass substrate with an indium tin oxide (ITO) transparent electrode, on which a 2 mm wide ITO film (thickness: 110 nm) was patterned in stripes, was prepared as the substrate 1 having an anode 2 on its surface. The substrate was then washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet cleaning.

[0155] (Preparation for vacuum deposition) After cleaning and surface treatment, each layer was deposited by vacuum deposition on the substrate by vacuum deposition, so that each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber and 1.0×10 -4 The pressure was reduced to 100 Pa. Then, each layer was formed according to the film formation conditions in the following order. Each organic material was formed by resistance heating.

[0156] (Fabrication of Hole Injection Layer 3) Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a ratio of 99:1 (mass ratio) to form a 10 nm film, to prepare a hole injection layer 3. The film formation rate was 0.1 nm / sec.

[0157] (Preparation of First Hole Transport Layer 41) Sublimation purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film of 85 nm at a rate of 0.2 nm / sec to prepare a first hole transport layer 41 .

[0158] (Preparation of second hole transport layer 42) Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1′-biphenyl-4-yl)amine was formed into a film of 5 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer 42 .

[0159] (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 ratio of 95:5 (mass ratio) to form a 20 nm film, thereby producing the light-emitting layer 5. The film formation rate was 0.1 nm / sec.

[0160] (Preparation of Hole Blocking Layer 9) The 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine synthesized in Synthesis Example 1 was deposited to a thickness of 6 nm at a rate of 0.05 nm / sec to form a hole blocking layer 9.

[0161] (Preparation of Electron Transport Layer 6) Sublimation-purified 4'-{4-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl]-1,1'-biphenylcarbonitrile and 8-hydroxyquinolinolatolithium (hereinafter, Liq) were mixed in a mass ratio of 50:50 to form a 25 nm film, thereby producing an electron transport layer 6. The film formation rate was 0.15 nm / sec.

[0162] (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 .

[0163] (Preparation of cathode 8) Finally, a metal mask was placed so as to be perpendicular to the ITO stripes (anode 2) on the substrate 1, and a cathode 8 was formed. The cathode had a two-layer structure in which silver / magnesium (mass ratio 1 / 10) and silver were formed in that order to thicknesses of 80 nm and 20 nm, respectively. The film formation rate of silver / magnesium was 0.5 nm / sec, and the film formation rate of silver was 0.2 nm / sec.

[0164] As a result, the light-emitting area of ​​4 mm2 shown in Figure 2 2 An organic electroluminescence device 100 was produced. The film thickness of each layer was measured using a stylus film thickness measuring instrument (DEKTAK, manufactured by Bruker). Furthermore, this element was sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less by sealing a glass sealing cap and the film-formed substrate (element) with bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation).

[0165] Element reference example 1 An organic electroluminescent device was produced in the same manner as in Element Example 1, except that in the hole blocking layer 9, instead of forming a 6 nm film of 2-{3-(2-biphenylyl)-5-(9,9-dimethylxanthen-3-yl)phenyl}-4,6-diphenyl-1,3,5-triazine at a rate of 0.05 nm / sec, a 6 nm film of ETL-1 was formed at a rate of 0.05 nm / sec.

[0166] A direct current was applied to the produced organic electroluminescent device, and the light-emitting characteristics were evaluated according to the method described in the above-mentioned measurement of light-emitting characteristics.

[0167] The light emission characteristics are as follows: current density 10mA / cm 2 The voltage (V) and current efficiency (cd / A) were measured when current was applied, and the device lifespan during continuous lighting was measured. The device lifespan is measured when the initial luminance is 1000 cd / m 2 The luminance decay time was measured when the device was continuously lit when driven at 1000 Hz, and the luminance (cd / m2 The time required for the capacitance to decrease by 2% was measured. The voltage (V), current efficiency (cd / 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.

[0168] [Table 1]

[0169] From Table 1, it was found that the organic electroluminescent device using the triazine compound (1) was extremely superior in device life as compared with the reference example. [Explanation of symbols]

[0170] 1. Substrate 2.Anode 3. Hole injection layer 4. Hole transport layer 5.Emitting layer 6.Electron transport layer 7.Electron injection layer 8.Cathode 9. Hole blocking layer 41.First hole transport layer 42.Second hole transport layer 100. Organic electroluminescent device

Claims

1. Triazine compound represented by formula (1): 【Chemistry 1】 During the ceremony, Ar １ and Ar ２ each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar １ and Ar ２ each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R １ teeth, Hydrogen atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R ２ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two R's ２ At least one of represents an alkyl group having 1 to 6 carbon atoms, or Two R's ２ together with the carbon atoms to which they are attached form a cyclopentane or cyclohexane ring; R ３ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two adjacent R ３ may be taken together with the carbon atom to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; When p is 2, two L's may be different from each other.

2. The triazine compound according to claim 1, which is a compound represented by formula (1a): 【Chemistry 2】 In the formula, Ar １ , Ar ２ , R １ , R ２ , R ３ , Z, L and p are the same as defined in formula (1).

3. Ar １ and Ar ２ The triazine compound according to claim 1 or 2, wherein each of the is independently a phenyl group or a biphenylyl group.

4. Ar １ and Ar ２ The triazine compound according to any one of claims 1 to 3, wherein

5. R １ but, an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or 5. The triazine compound according to claim 1, which is a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.

6. R １ The triazine compound according to any one of claims 1 to 5, wherein is a phenyl group, a biphenyl group, a naphthyl group, or a phenanthrenyl group.

7. R ３ are the same or different, A hydrogen atom, or The triazine compound according to any one of claims 1 to 6, wherein the alkyl group has 1 to 6 carbon atoms.

8. The triazine compound according to any one of claims 1 to 7, wherein Z is an oxygen atom.

9. 9. The triazine compound according to claim 1, wherein L is a metaphenylene group or a paraphenylene group which may be substituted with a phenyl group, a naphthyl group, or an alkyl group having 1 to 4 carbon atoms.

10. 10. The triazine compound according to claim 1, wherein p is 0 or 1.

11. A method for producing a triazine compound represented by formula (1), comprising subjecting a compound represented by formula (2) and a compound represented by formula (3) to a coupling reaction: 【Chemistry 3】 During the ceremony, Ar １ and Ar ２ each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar １ and Ar ２ each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R １ teeth, Hydrogen atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R ２ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two R's ２ At least one of represents an alkyl group having 1 to 6 carbon atoms, or Two R's ２ together with the carbon atoms to which they are attached form a cyclopentane or cyclohexane ring; R ３ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two adjacent R ３ may be joined together with the carbon atom to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; M １ ZnY １ , MgY ２ , Sn(Y ３ ) ３ , or B(OY ４ ) ２ Represents; Y １ and Y ２ each independently represents a chlorine atom, a bromine atom, or an iodine atom; Y ３ each independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group; Y ４ each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; Two (OY ４ ) groups may be taken together to form a ring with the boron atom; X １ represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom.

12. A method for producing a triazine compound represented by formula (1), comprising subjecting a compound represented by formula (4) and a compound represented by formula (5) to a coupling reaction: 【Chemistry 4】 During the ceremony, Ar １ and Ar ２ each independently represents a phenyl group, a biphenylyl group, or a naphthyl group; Ar １ and Ar ２ each independently may be substituted with one or more groups selected from the group consisting of a fluorine atom, an alkyl group having 1 to 4 carbon atoms, and a phenyl group; R １ teeth, Hydrogen atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring; or represents a nitrogen-containing aromatic group having 4 to 14 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms; R ２ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two R's ２ At least one of represents an alkyl group having 1 to 6 carbon atoms, or Two R's ２ together with the carbon atoms to which they are attached form a cyclopentane or cyclohexane ring; R ３ are the same or different, Hydrogen atoms, an alkyl group having 1 to 6 carbon atoms, or represents a monocyclic, linked, or fused ring aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms; Two adjacent R ３ may be joined together with the carbon atom to which they are attached to form a 5- or 6-membered ring; Z represents an oxygen atom or a sulfur atom; L represents a phenyl group, a naphthyl group, or a phenylene group or naphthylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms; p represents 0, 1 or 2; X ２ represents a chlorine atom, a bromine atom, a trifluoromethanesulfonyloxy group, or an iodine atom; M ２ ZnY １ , MgY ２ , Sn(Y ３ ) ３ , or B(OY ４ ) ２ Represents; Y １ and Y ２ each independently represents a chlorine atom, a bromine atom, or an iodine atom; Y ３ each independently represents an alkyl group having 1 to 4 carbon atoms or a phenyl group; Y ４ each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group; Two (OY ４ ) groups may be joined together to form a ring with the boron atom.

13. M １ Or M ２ But B(OY ４ ) ２ The method for producing a triazine compound according to claim 11 or 12, 14. The method according to claim 11, wherein the coupling reaction is carried out in the presence of a palladium catalyst, the palladium catalyst having a tertiary phosphine as a ligand.

15. The method according to claim 11, wherein the coupling reaction is carried out in the presence of a palladium catalyst, and the palladium catalyst has triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl as a ligand.

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

17. An organic electroluminescent device comprising the triazine material according to any one of claims 1 to 10.

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