Triazine compound, and organic electroluminescent element, electronic device, and electronic element using said compound

Abstract

The purpose of the present invention is to provide: a compound having a high refractive index and a low extinction coefficient at 450-750 nm in order to improve the light extraction efficiency of an organic electroluminescent (EL) element; and an organic EL element using said compound in a capping layer.　The present invention relates to: a compound represented by general formula (I), and an organic electroluminescent element having at least an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode, and a capping layer in this order, wherein the capping layer contains the compound represented by general formula (I). (For the definition of symbols, refer to the specification.)

Description

Triazine compounds, and organic electroluminescent elements, electronic devices, and electronic components using the same.

[0001] The present invention relates to a triazine compound suitable for self-emissive electronic elements suitable for various display devices, particularly for organic electroluminescent elements (hereinafter abbreviated as organic EL elements), and to organic EL elements, electronic devices, and electronic elements using the compound.

[0002] Organic EL elements have been the subject of active research because they are brighter, more visible, and capable of sharper displays compared to liquid crystal elements.

[0003] In 1987, C. W. Tang et al. at Eastman Kodak made organic EL elements (OLEDs) practical by developing a multilayer structure in which various roles are assigned to each material. To date, many improvements have been made to make organic EL elements practical, and by further subdividing the roles of each layer in the multilayer structure and sequentially arranging the anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and cathode on the substrate, high efficiency and durability have been achieved by designing a bottom-emission light-emitting element that emits light from the bottom (see Non-Patent Literature 1).

[0004] In recent years, light-emitting devices with a top-emission structure, which use a metal with a high work function as the anode and emit light from the top, have come into use. In bottom-emission light-emitting devices, which extract light from the bottom where the pixel circuit is located, the area of ​​the light-emitting part is limited. In contrast, top-emission light-emitting devices have the advantage that the pixel circuit is not obstructed because light is extracted from the top, allowing for a wider light-emitting part. On the other hand, in top-emission light-emitting devices, if the light emitted from the light-emitting layer is incident on another film at an angle greater than a certain angle, it is totally reflected at the interface between the light-emitting layer and the other film, and only a portion of the emitted light can be used. Therefore, in order to improve the light extraction efficiency, light-emitting devices have been proposed in which a capping layer with a high refractive index is provided on the outside of a semi-transparent electrode (cathode) with a low refractive index such as LiF / Al / Ag, Ca / Mg, or LiF / MgAg (see Non-Patent Documents 2 and 3).

[0005] International Publication No. 2014 / 009310 US2015 / 0287920 A1

[0006] Proceedings of the 9th Seminar of the Japan Society of Applied Physics, 2001, p. 55-61Appl. Phys. Lett. , (USA), 2001, Volume 78, No. 4, p. 544-546Appl. Phys. Lett. , (USA), 2003, Volume 82, No. 3, p. 466-468 Tetrahedron, (Netherlands), 2002, Volume 58, p. 9633-9695Appl. Phys. Lett. , (USA), 2011, Volume 98, No. 8, p. 083302

[0007] Conventionally, highly detailed metal masks have been used to form the capping layer. However, when used under high-temperature conditions, heat can cause distortion in the metal mask, leading to a decrease in alignment accuracy. Therefore, ZnSe (melting point: 1100°C or higher), which is used in the capping layer in Non-Patent Document 3, may not be able to be deposited in the correct position depending on the highly detailed metal mask, potentially adversely affecting the light-emitting element. Furthermore, even film deposition by sputtering can adversely affect the light-emitting element, making inorganic materials unsuitable as constituent materials for the capping layer.

[0008] Furthermore, Non-Patent Document 2 describes tris(8-hydroxyquinoline)aluminum (Alq) as a constituent material for the capping layer used to adjust the refractive index. ３ It has been proposed to use ). However, Alq ３ Alq is a common material used as a green light-emitting material or electron transport material, and it exhibits weak absorption around 450 nm, which is close to the emission wavelength of blue light-emitting materials. Therefore, Alq ３ When used in a blue light-emitting device, there was a problem of reduced color purity and light extraction efficiency.

[0009] As described above, in order to improve the device characteristics of organic EL elements and to improve the light extraction efficiency, there is a need for a material that can be used as a capping layer, which has a high refractive index, a low extinction coefficient, and excellent thin-film stability, deposition properties, and durability.

[0010] An object of the present invention is to provide a compound having a high refractive index and a low attenuation coefficient in a wavelength range of 450 nm to 750 nm, which is suitable as a material used for a capping layer of an organic EL element. Another object of the present invention is to provide an organic EL element having an improved light extraction efficiency as compared with the prior art.

[0011] Therefore, in order to achieve the above object, the present inventors focused on the fact that the triazine compound is excellent in the stability and durability of the thin film, and intensively optimized the molecular design. As a result, the present invention has been completed by developing a material having a high refractive index and a low attenuation coefficient in a wavelength range of 450 nm to 750 nm.

[0012] That is, the present invention is a triazine compound represented by the following general formula (I).

[0013] (In the formula, Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and Ar ３ represents a substituted or unsubstituted group selected from the group consisting of a pyrimidinyl group, a quinolyl group, a quinoxalinyl group, a benzofuranyl group, a benzothienyl group, a phenanthrolinyl group, a dibenzothienyl group, an oxazolopyridyl group and a benzothiazolyl group, and L １ , L ２ and L ３ each independently represents a single bond or a substituted or unsubstituted arylene group.)

[0014] Further, the present invention is an organic EL element having at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein the capping layer contains the triazine compound represented by the general formula (I).

[0015] The triazine compound of the present invention has a high refractive index in the wavelength range of 450 nm to 750 nm, a low extinction coefficient, is suitable for deposition, maintains a stable thin film state, and has high heat resistance. Therefore, by providing a capping layer containing this compound on the outside of the electrodes of an organic EL element, the light extraction efficiency can be improved compared to conventional methods.

[0016] This figure shows an example of the configuration of the organic EL element of the present invention.

[0017] The contents of the present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Furthermore, the isotopes of hydrogen atoms present in the molecule of the compound used in the present invention are not particularly limited, for example, all hydrogen atoms in the molecule １ H is fine, or part or all of it ２ It may also be H (deuterium D). In this specification, the term "substituted or unsubstituted" means that the group to which the term is attached may be an unsubstituted group (a group in which hydrogen atoms are not substituted with substituents), or at least one hydrogen atom of the group may be substituted with substituents. The term "deuterium-substituted or unsubstituted" means that the group to which the term is attached may be an unsubstituted group (a group in which hydrogen atoms are not substituted with substituents), or at least one hydrogen atom of the group may be a deuterium atom ( ２ This means that it may be H). However, as described above, the hydrogen atoms present in the molecule of the compound used in this invention are １ Even if it's H ２It may also be H (deuterium D). Therefore, the "deuterium substitution" in "deuterium substitution or unsubstituted" is a cautionary statement that the description "unsubstituted" does not exclude the form in which the hydrogen atom is a "deuterium atom". In this specification, "organic layer" means a layer containing 70% by weight or more of an organic compound, and "organic compound" means a compound containing one or more carbon atoms. For example, the organic compound may consist only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms. In this specification, "transparent" means that the transmittance of visible light is 50% or more, for example 80% or more, for example 90% or more, for example 99% or more. The transmittance of visible light can be measured by an ultraviolet-visible spectrophotometer.

[0018] The triazine compound of the present invention is a compound represented by the following general formula (I).

[0019] (In the formula, Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Ar ３ L represents a group selected from the group consisting of substituted or unsubstituted pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, and benzothiazolyl groups. １ , L ２ and L ３ Each of these independently represents a single bond, or a substituted or unsubstituted arylene group.

[0020] In general formula (I), Ar １ and Ar ２The aromatic ring constituting the "aryl group" in the "substituted or unsubstituted aryl group" represented by Ar may be a monoring, a fused ring formed by the fusion of two or more rings, a linked ring formed by the single bond between two or more rings, or a spiroring formed by the spiro bond between two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example 2 to 4. In the case of a linked ring, the number of linked rings is preferably 2 to 6, for example 2 to 4. The number of carbon atoms in the aromatic ring is, for example 6 to 30, for example 6 to 22, for example 6 to 18, for example 6 to 14, for example 6 to 10. １ and Ar ２ Specifically, the following groups can be cited as "aryl groups" in this context: aryl groups consisting of 6 to 30 carbon atoms, such as phenyl, biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, indenyl, pyrenyl, perilenyl, fluoranthenyl, triphenylenyl, fluorenyl, and spirobifluorenyl.

[0021] In general formula (I), Ar １ and Ar ２ The aromatic heterocycle constituting the "heteroaryl group" in the "substituted or unsubstituted heteroaryl group" represented by can be a monocycle or a fused ring formed by the fusion of two or more rings. If it is a fused ring, the number of fused rings is preferably 2 to 6, for example, 2 to 4. Examples of heteroatoms constituting the aromatic heterocycle include nitrogen, oxygen, and sulfur atoms. The number of carbon atoms in the aromatic heterocycle is, for example, 2 to 40, for example, 2 to 30, for example, 2 to 18, for example, 2 to 12. １ and Ar ２Specifically, the following groups can be cited as "heteroaryl groups" in this context: heteroaryl groups having 2 to 20 carbon atoms, such as pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, pyrazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolyl group, naphthilidinyl group, benzofuranyl group, benzothienyl group, indolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, imidazopyridyl group, oxazolopyridyl group, oxazolopyradinyl group, dibenzofuranyl group, dibenzothienyl group, phenanthrolinyl group, acridinyl group, carbazolyl group, and carbolinyl group. The oxazolopyridyl group may be any of the following: oxazolo[4,5-b]pyridyl group, oxazolo[5,4-b]pyridyl group, oxazolo[4,5-c]pyridyl group, or oxazolo[5,4-c]pyridyl group. The phenanthrolinyl group may be any of the following: [4,7]phenanthrolinyl group, [3,8]phenanthrolinyl group, [2,9]phenanthrolinyl group, or [1,10]phenanthrolinyl group.

[0022] In general formula (I), Ar ３ The above Ar １ and Ar ２ This represents a specific group selected from the "substituted or unsubstituted heteroaryl groups" represented by . Specifically, it is a group selected from the group consisting of substituted or unsubstituted pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, and benzothiazolyl groups.

[0023] In general formula (I), L １ ~L ３ The "arylene group" in "substituted or unsubstituted arylene group" represented by Ar １ ~Ar ３A possible example is a group obtained by removing one hydrogen atom from the group shown as an "aryl group" represented by . The aromatic ring constituting the "arylene group" may be a monoring, a fused ring formed by the fusion of two or more rings, a linked ring formed by the single bond between two or more rings, or a spiroring formed by the spiro bond between two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example 2 to 4. In the case of a linked ring, the number of linked rings is preferably 2 to 6, for example 2 to 4. The number of carbon atoms in the aromatic ring is, for example 6 to 30, for example 6 to 22, for example 6 to 18, for example 6 to 14, for example 6 to 10. L １ ~L ３ Specifically, the following groups can be cited as "arylene groups" in this context: arylene groups consisting of 6 to 30 carbon atoms, such as phenylene group, biphenylene group, terphenylene group, naphthylene group, anthrylene group, phenanthrylene group, indenylene group, pyrenylene group, perillenylene group, fluorantheylene group, triphenylenylene group, fluorenylene group, and spirobifluorenylene group.

[0024] In general formula (I), Ar １ ~Ar ３ and L １ ~L ３The following atoms or groups can be specifically listed as "substituents" in the group represented by: deuterium atoms; cyano groups; nitro groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; silyl groups such as trimethylsilyl and triphenylsilyl groups; linear or branched alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, and propyl groups; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, and propoxy groups; alkenyl groups such as vinyl and allyl groups; aryl groups having 6 to 30 carbon atoms such as phenyl, biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, perilenyl, fluoranthenyl, and triphenylenyl groups; Heteroaryl groups having 2 to 20 carbon atoms, such as pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, imidazopyridyl, oxazolopyridyl, oxazolopyradinyl, quinoxalinyl, quinazolyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthilidinyl, acridinyl, carbonyl, and phenanthrolinyl groups; aryloxy groups such as phenyloxy, tolyloxy, biphenylyloxy, and naphthyloxy; and aralkyloxy groups such as benzyloxy and phenethyloxy. The hydrogen atoms of these substituents may be further substituted with the substituents exemplified herein. Preferred substituents include deuterium atoms, linear or branched alkyl groups having 1 to 6 carbon atoms, and monovalent aromatic hydrocarbon groups having 6 to 20 constituent atoms in the ring skeleton. In addition, substituents that are substituted by other substituents are sometimes referred to as "first substituents" if they are directly substituted on the parent skeleton (aromatic hydrocarbon group, aromatic heterocyclic group), and "second substituents" if they are substituted on the first substituent. Here, if the first substituent includes an aromatic ring, that aromatic ring may be bonded to the parent skeleton to form a cyclic structure.Furthermore, if two or more substituents are substituted on the aromatic ring of the first substituent, adjacent substituents may bond to each other to form a cyclic structure. Here, the bond between the aromatic ring in the first substituent and the mother skeleton, and the bond between the second substituents, may be a single bond or a bond via a linking group. Examples of linking groups include substituted or unsubstituted methylene groups, oxygen atoms, or sulfur atoms.

[0025] In general formula (I), Ar １ and Ar ２ The substituted or unsubstituted aryl groups represented by are preferably independently selected from the group consisting of substituted or unsubstituted phenyl groups, naphthyl groups, and phenanthryl groups, and more preferably selected from the group consisting of unsubstituted phenyl groups, naphthyl groups, and phenanthryl groups.

[0026] In substituted or unsubstituted naphthyl groups, the naphthyl group is preferably a 2-naphthyl group. In substituted or unsubstituted phenanthryl groups, the phenanthryl group is preferably a 9-phenanthryl group. In substituted or unsubstituted pyrimidinyl groups, the pyrimidinyl group is preferably a 2-pyrimidinyl group or a 4-pyrimidinyl group. In substituted or unsubstituted quinolyl groups, the quinolyl group is preferably a 2-quinolyl group or a 3-quinolyl group. In substituted or unsubstituted quinoxalinyl groups, the quinoxalinyl group is preferably a 2-quinoxalinyl group. In substituted or unsubstituted benzofuranyl groups, the benzofuranyl group is preferably a 2-benzofuranyl group. In substituted or unsubstituted benzothienyl groups, the benzothienyl group is preferably a 2-benzothienyl group. In substituted or unsubstituted benzoxazolyl groups, the benzoxazolyl group is preferably a 2-benzoxazolyl group. In substituted or unsubstituted benzothiazolyl groups, the benzothiazolyl group is preferably a 2-benzothiazolyl group. In substituted or unsubstituted oxazolopyridyl groups, the oxazolopyridyl group is preferably an oxazolo[5,4-b]pyridyl group, and more preferably a 2-oxazolo[5,4-b]pyridyl group. In substituted or unsubstituted phenanthrolinyl groups, the phenanthrolinyl group is preferably a [1,10]phenanthrolinyl group, and more preferably a 2-[1,10]phenanthrolinyl group.

[0027] In this invention, Ar １ However, it is a substituted or unsubstituted aryl group, Ar ２ However, it is preferable that the group is selected from substituted or unsubstituted naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, benzothiazolyl, and pyridyl groups.

[0028] Also Ar ３It is particularly preferable that the group is selected from substituted 5-pyridyl groups, substituted 5-pyrimidinyl groups, and substituted 6-quinoxalinyl groups, having an unsubstituted 3-quinolyl group, 2-quinoxalinyl group, 2-benzofuranyl group, 2-benzothienyl group, 2-[1,10]phenanthrolinyl group, 2-dibenzothienyl group, 2-oxazolo[5,4-b]pyridyl group, 2-benzothiazolyl group, phenyl group, or naphthyl group as substituents.

[0029] In general formula (I), L １ ~L ３ The substituted or unsubstituted arylene groups represented by are preferably independently selected from the group consisting of substituted or unsubstituted phenylene groups, biphenylylene groups, and naphthylene groups, more preferably being unsubstituted phenylene groups, and even more preferably being 1,4-phenylene groups.

[0030] In the present invention, when Ar1 is a substituted or unsubstituted aryl group and L2 and L3 are 1,4-phenylene groups, it is preferable that Ar2 is a group selected from a substituted or unsubstituted naphthyl group, pyrimidinyl group, quinolyl group, quinoxalinyl group, benzofuranyl group, benzothienyl group, phenanthrolinyl group, dibenzothienyl group, oxazolopyridyl group, benzothiazolyl group and pyridyl group, and that Ar3 is a group selected from a substituted or unsubstituted pyrimidinyl group, quinolyl group, quinoxalinyl group, benzofuranyl group, benzothienyl group, phenanthrolinyl group, dibenzothienyl group, oxazolopyridyl group and benzothiazolyl group. It is more preferable that Ar2 is an unsubstituted group selected from naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, benzothiazolyl, and pyridyl groups, and that Ar3 is an unsubstituted group selected from unsubstituted 3-quinolyl, 2-quinoxalinyl, 2-benzofuranyl, 2-benzothienyl, 2-[1,10]phenanthrolinyl, 2-dibenzothienyl, 2-oxazolo[5,4-b]pyridyl, and 2-benzothiazolyl groups, as well as a substituted 5-pyridyl, substituted 5-pyrimidinyl, and substituted 6-quinoxalinyl groups having a phenyl or naphthyl group as a substituent. It is even more preferable that Ar2 is an unsubstituted group selected from naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, and oxazolopyridyl groups, and that Ar3 is an unsubstituted group selected from 3-quinolyl, 2-quinoxalinyl, 2-benzofuranyl, 2-benzothienyl, 2-[1,10]phenanthrolinyl, 2-oxazolo[5,4-b]pyridyl, and 2-benzothiazolyl groups.

[0031] In the present invention, when Ar1 is a substituted or unsubstituted aryl group, L2 is a 1,4-phenylene group, and L3 is a single bond, it is preferable that Ar2 is a group selected from substituted or unsubstituted naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, benzothiazolyl, and pyridyl groups, and that Ar3 is a group selected from substituted or unsubstituted pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, and benzothiazolyl groups. It is more preferable that Ar2 is an unsubstituted group selected from naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, benzothiazolyl, and pyridyl groups, and that Ar3 is an unsubstituted group selected from unsubstituted 3-quinolyl, 2-quinoxalinyl, 2-benzofuranyl, 2-benzothienyl, 2-[1,10]phenanthrolinyl, 2-dibenzothienyl, 2-oxazolo[5,4-b]pyridyl, and 2-benzothiazolyl groups, as well as a substituted 5-pyridyl, substituted 5-pyrimidinyl, and substituted 6-quinoxalinyl groups having a phenyl or naphthyl group as a substituent. It is even more preferable that Ar2 is an unsubstituted group selected from naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, benzothiazolyl, and oxazolopyridyl groups, and that Ar3 is a substituted group selected from substituted 5-pyrimidinyl and substituted 6-quinoxalinyl groups having a phenyl or naphthyl group as a substituent.

[0032] In the present invention, when Ar1 is a substituted or unsubstituted aryl group and L2 and L3 are single bonds, it is preferable that Ar2 is a group selected from a substituted or unsubstituted naphthyl group, pyrimidinyl group, quinolyl group, quinoxalinyl group, benzofuranyl group, benzothienyl group, phenanthrolinyl group, dibenzothienyl group, oxazolopyridyl group, benzothiazolyl group and pyridyl group, and that Ar3 is a group selected from a substituted or unsubstituted pyrimidinyl group, quinolyl group, quinoxalinyl group, benzofuranyl group, benzothienyl group, phenanthrolinyl group, dibenzothienyl group, oxazolopyridyl group and benzothiazolyl group. It is more preferable that Ar2 is a group selected from substituted naphthyl, pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, benzothiazolyl, and pyridyl groups, and that Ar3 is a group selected from unsubstituted 3-quinolyl, 2-quinoxalinyl, 2-benzofuranyl, 2-benzothienyl, 2-[1,10]phenanthrolinyl, 2-dibenzothienyl, 2-oxazolo[5,4-b]pyridyl, and 2-benzothiazolyl groups, as well as substituted 5-pyridyl, substituted 5-pyrimidinyl, and substituted 6-quinoxalinyl groups having a phenyl or naphthyl group as a substituent. It is even more preferable that Ar2 is an unsubstituted group selected from a pyrimidinyl group, a quinolyl group, and a quinoxalinyl group, and that Ar3 is a substituted group selected from a substituted 5-pyrimidinyl group and a substituted 6-quinoxalinyl group having a phenyl group or a naphthyl group as a substituent.

[0033] Specific examples of triazine compounds represented by general formula (I) are shown below. However, the triazine compounds of the present invention should not be interpreted as being limited by these specific examples. Also, in the chemical structural formulas below, the hydrogen atom ( １ The notation H) is omitted.

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] The triazine compound represented by the general formula (I) can be synthesized, for example, by known coupling reactions using a palladium catalyst (see, for example, Non-Patent Document 4).

[0046] The method for purifying the triazine compound is not particularly limited, and it can be purified by known methods used for purifying organic compounds, such as purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization purification with a solvent, or sublimation purification. The compound can be identified, for example, by NMR analysis or liquid chromatography-mass spectrometry (LC-MS).

[0047] It is preferable to measure the melting point, glass transition temperature (Tg), sublimation temperature, refractive index, and extinction coefficient as physical properties of the triazine compound. The melting point and sublimation temperature serve as indicators of vapor deposition properties, and the glass transition temperature (Tg) serves as an indicator of the stability of the thin film state. Furthermore, the refractive index and extinction coefficient serve as indicators related to improving the light extraction efficiency.

[0048] The melting point and glass transition temperature (Tg) of the powder can be measured using a high-sensitivity differential scanning calorimeter (e.g., Bruker AXS, product name: DSC3100SA).

[0049] The refractive index and extinction coefficient can be measured for an 80 nm thin film fabricated on a silicon substrate using a spectroscopic measuring device (e.g., Filmetrics, product name: F10-RT-UV).

[0050] In the present invention, when the triazine compound represented by the general formula (I) is deposited on a silicon substrate to a thickness of 80 nm by vacuum deposition, the refractive index of the formed film, measured at room temperature (25 ± 2°C), is preferably 1.70 or higher, more preferably 1.85 or higher, and particularly preferably 1.90 or higher in the wavelength range of 450 nm to 700 nm. A high refractive index significantly improves the light extraction efficiency when used as a capping layer for an organic EL element.

[0051] <Organic EL element> The organic EL element of the present invention has at least an anode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode, and a capping layer in this order.

[0052] As for the structure of an organic EL element, for example, in the case of a top-emission light-emitting element, as shown in Figure 1, an anode 2, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, a cathode 8, and a capping layer 9 are sequentially stacked on a glass substrate 1. Other examples include those having a hole injection layer 3 between the anode and the hole transport layer, those having an electron blocking layer between the hole transport layer and the light-emitting layer, those having a hole blocking layer between the light-emitting layer and the electron transport layer, and those having an electron injection layer 7 between the electron transport layer and the cathode. In these multilayer structures, one organic layer can serve multiple roles. For example, a configuration can be used in which the hole injection layer and hole transport layer are combined, a configuration can be used in which the hole transport layer and electron blocking layer are combined, a configuration can be used in which the hole blocking layer and electron transport layer are combined, and / or a configuration can be used in which the electron transport layer and electron injection layer are combined. Furthermore, a configuration can be used in which two or more organic layers having the same function are stacked. Specifically, these include configurations with two stacked hole transport layers, two stacked light-emitting layers, two stacked electron transport layers, and / or two stacked capping layers. The following describes each layer that constitutes the organic EL element.

[0053] [Capping layer] In the organic EL element of the present invention, the capping layer contains at least a triazine compound represented by the general formula (I).

[0054] In the present invention, the capping layer contains a triazine compound represented by the general formula (I). The capping layer may also be a laminated or mixed layer containing two or more compounds, including the triazine compound represented by the general formula (I). Examples of compounds other than the triazine compound represented by the general formula (I) include phthalic acid derivatives (see Patent Document 2). Of course, it may also contain two or more types of triazine compounds represented by the general formula (I). These may be deposited individually, or used as a single layer deposited by mixing with other materials. Alternatively, a laminated structure may be formed of layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing. These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet printing.

[0055] [Other layers] For the anode, electrode materials with a large work function, such as ITO or gold, are used.

[0056] As materials for the hole injection layer, arylamine compounds having a structure in which two or more triphenylamine structures in the molecule are linked by single bonds or divalent groups that do not contain heteroatoms, such as starburst-type triphenylamine derivatives and various triphenylamine tetramers; porphyrin compounds represented by copper phthalocyanine; and acceptor-type heterocyclic compounds such as hexacyanoazatriphenylene, as well as coating-type polymer materials can be used. These may be deposited individually or used as monolayers deposited by mixing with other materials. Alternatively, they may be used in a laminated structure of layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing. These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet.

[0057] As the material for the hole transport layer, benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine, and N,N,N',N'-tetrabiphenylylbenzidine, as well as 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane can be used. In particular, it is preferable to use an arylamine compound having a structure in which two triphenylamine structures are linked in the molecule by single bonds or by divalent groups that do not contain heteroatoms, such as N,N,N',N'-tetrabiphenylylbenzidine. It is also preferable to use an arylamine compound having a structure in which three or more triphenylamine structures are linked in the molecule by single bonds or by divalent groups that do not contain heteroatoms, such as various triphenylamine trimers and tetramers. These may be deposited as films alone, or they may be used as monolayers deposited by mixing them with other materials. Alternatively, a laminated structure may be formed by layering layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing. Furthermore, a coating-type polymer material such as poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonate) can be used as the material for the hole injection layer and hole transport layer. These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet.

[0058] Furthermore, as materials for the hole injection layer and hole transport layer, materials that are normally used for these layers can be P-doped with dopants such as trisbromophenylamine hexachloroantimony and radialene derivatives (see Patent Document 1), as well as polymer compounds having a benzidine derivative structure such as TPD as a substructure.

[0059] The organic EL element of the present invention may have an electron blocking layer. As the material for the electron blocking layer, carbazole derivatives such as 4,4',4''-tri(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazole-9-yl)phenyl]fluorene, 1,3-bis(carbazole-9-yl)benzene (mCP), and 2,2-bis(4-carbazole-9-yl-phenyl)adamantane, as well as compounds having an electron blocking effect, such as compounds having a triphenylsilyl group and a triarylamine structure, represented by 9-[4-(carbazole-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can be used. These may be deposited as films on their own, or as monolayers deposited by mixing them with other materials. Alternatively, a laminated structure may be formed with layers deposited individually, layers deposited by mixing them, or layers deposited individually and layers deposited by mixing them. These materials can be deposited into films by known methods such as vapor deposition, spin coating, and inkjet printing.

[0060] As for the material of the light-emitting layer, Alq ３Metal complexes of quinolinol derivatives such as quinolinol derivatives, various metal complexes, anthracene derivatives, bis-styrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and poly(p-phenylenevinylene) derivatives can be used. The light-emitting layer may also consist of a host material and a dopant material. Anthracene derivatives are preferably used as the host material. Other materials that can be used as the host material include the material for the light-emitting layer, heterocyclic compounds having an indole ring as a substructure of the fused ring, heterocyclic compounds having a carbazole ring as a substructure of the fused ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives. As dopant materials, quinacridone, coumarin, rubrene, perylene, pyrene and their derivatives, benzopyran derivatives, rhodamine derivatives, and aminostyryl derivatives can be used. It is preferable to use a green light-emitting material as the dopant material. These materials may be deposited individually, or they may be used as single layers deposited by mixing them with other materials. They may also be used in laminated structures consisting of layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing.

[0061] Furthermore, phosphorescent materials can also be used as dopant materials. Metal complexes such as iridium and platinum can be used as phosphorescent materials. Specifically, Ir(ppy) ３ Green phosphorescent materials such as Firpic and Fir6, blue phosphorescent materials such as Btp ２ Examples of red phosphorescent materials include Ir(acac). Among these, it is preferable to use a green phosphorescent material. As host materials, hole-injecting and hole-transporting host materials such as 4,4'-di(N-carbazolyl)biphenyl, TCTA, and carbazole derivatives such as mCP, and electron-transporting host materials such as p-bis(triphenylsilyl)benzene and 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) can be used.

[0062] To avoid concentration quenching, the doping of the phosphorescent material into the host material is preferably in the range of 1 to 30% by mass relative to the entire light-emitting layer and is carried out by co-deposition.

[0063] Furthermore, materials that emit delayed fluorescence, such as PIC-TRZ, CC2TA, PXZ-TRZ, and CDCB derivatives like 4CzIPN, can also be used as dopant materials (see Non-Patent Literature 5). These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet.

[0064] The organic EL element of the present invention may have a hole-blocking layer. As the material for the hole-blocking layer, compounds having hole-blocking properties such as phenanthroline derivatives such as bathocuproine, metal complexes of quinolinol derivatives such as aluminum(III)bis(2-methyl-8-quinolinate)-4-phenylphenolate (BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, and benzoazole derivatives can be used. These materials may also be used as materials for the electron transport layer. These may be deposited individually, or used as monolayers deposited by mixing with other materials. Alternatively, they may be used in a laminated structure of layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing. These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet.

[0065] As for the electron transport layer material, Alq ３In addition, metal complexes of quinolinol derivatives such as BAlq, various metal complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, benzoazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, and silole derivatives can be used. These may be deposited as films on their own, or as monolayers deposited by mixing them with other materials. Alternatively, they may be used in a laminated structure of layers deposited individually, layers deposited by mixing, or layers deposited individually and layers deposited by mixing. These materials can be deposited by known methods such as vapor deposition, spin coating, and inkjet printing.

[0066] As materials for the electron injection layer, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. The electron injection layer can be omitted depending on the preferred selection of the electron transport layer and cathode.

[0067] Furthermore, as materials for the electron transport layer and electron injection layer, materials that are N-doped with metals such as cesium can be used in addition to the materials normally used for these layers.

[0068] Materials used for the cathode include metals with low work functions such as aluminum, alloys with even lower work functions such as magnesium-silver alloys, magnesium-calcium alloys, magnesium-indium alloys, and aluminum-magnesium alloys, as well as ITO and IZO.

[0069] The total thickness of each layer of the organic EL element is preferably 200 nm to 750 nm, and more preferably 350 nm to 600 nm. The thickness of the capping layer is preferably, for example, 30 nm to 120 nm, and more preferably 40 nm to 80 nm. When the capping layer thickness is within the above range, better light extraction efficiency can be obtained. The thickness of the capping layer can be appropriately changed depending on the type of light-emitting material used in the light-emitting element and the thickness of each layer other than the capping layer.

[0070] Although the above describes an organic EL element with a top emission structure, the present invention is not limited thereto and can be similarly applied to organic EL elements with a bottom emission structure and organic EL elements with a dual emission structure that emit light from both the top and bottom. In any case, the electrodes in the direction from which light is extracted from the light-emitting element are preferably transparent or semi-transparent.

[0071] The physical properties of compounds suitable for the capping layer of organic EL elements include (1) a high refractive index, (2) a low extinction coefficient, (3) the ability to be deposited, (4) a stable thin film state, and (5) a high glass transition temperature. The physical properties of organic EL elements include (1) high light extraction efficiency, (2) no decrease in color purity, (3) light transmission without change over time, and (4) a long lifespan. The triazine compound of the present invention, represented by general formula (I) or (II), has the properties of a high refractive index, a low extinction coefficient, the ability to be deposited, a stable thin film state, and a high glass transition temperature. Therefore, by using such a triazine compound as the capping layer, it is possible to provide an organic EL element that has high light extraction efficiency, suppresses the decrease in color purity, transmits light without change over time, and has a long lifespan.

[0072] <Electronic Devices and Electronic Elements> The electronic device of the present invention comprises a pair of electrodes and at least one organic layer, wherein the organic layer contains an electronic element comprising a triazine compound represented by the general formula (I) described above. Preferably, at least one layer of the organic layer of the electronic element is provided on the outside of one of the electrodes, and more preferably, the organic layer provided on the outside of the electrodes contains a triazine compound represented by the general formula (I) described above.

[0073] The embodiments of the present invention will be described in detail below with reference to examples, but the present invention is not limited to the following embodiments unless it exceeds the gist of the invention.

[0074] The reagents used in the synthesis examples were manufactured by Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich, Alfa Aesar, etc. Furthermore, all reactions in the synthesis examples were carried out using reaction vessels equipped with condensers, stirrers, and thermometers. The identification of the compounds in the following synthesis examples was performed by: １ 1H-NMR analysis (Bruker nuclear magnetic resonance spectrometer, model: Ascend) ＴＭ The analysis was performed using 400 MHz or LC-MS mass spectrometry (using a SCIEXX mass spectrometer (model: API3200)).

[0075] [Synthesis Example 1] <Synthesis of Compound (39)> 12.5 g of 2-chloro-4,6-bis(4-(naphthalene-2-yl)phenyl)-1,3,5-triazine, 8.5 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)oxazolopyridine, 5.0 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium (0), 110 ml of tetrahydrofuran, and 40 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated monochlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered at 90°C using Celite filtration. The solvent was removed by distillation under reduced pressure, and the resulting mixture was purified by crystallization with monochlorobenzene to obtain Compound (39): 12.5 g (yield: 77%).

[0076] The structure of the obtained white powder was identified using NMR. １ H-NMR (CDCl ３ The following 29 hydrogen signals were detected: δ (ppm) = 8.99 (2H), 8.91 (4H), 8.51 (2H), 8.39 (1H), 8.18 (2H), 8.12 (1H), 7.98-7.84 (12H), 7.57-7.50 (4H), 7.38 (1H).

[0077]

[0078] [Synthesis Example 2] <Synthesis of Compound (41)> 8.0 g of 2,4-dichloro-6-(4-(naphthalene-2-yl)phenyl)-1,3,5-triazine, 16.0 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)benzofuran, 4.7 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium(0), 70 ml of tetrahydrofuran, and 20 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated monochlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered at 90°C using Celite filtration. The solvent was removed by distillation under reduced pressure, and the resulting mixture was purified by crystallization with monochlorobenzene to obtain Compound (41): 8.5 g (yield: 56%).

[0079] The structure of the obtained white powder was identified using NMR. １ H-NMR (DMSO-d ６ The following 29 hydrogen signals were detected: δ (ppm) = 8.92 (6H), 8.44 (1H), 8.25 (4H), 8.18 (2H), 8.10 (2H), 8.02 (2H), 7.77-7.72 (6H), 7.61 (2H), 7.42 (2H), 7.34 (2H).

[0080]

[0081] [Synthesis Example 3] <Synthesis of Compound (42)> 8.0 g of 2,4-dichloro-6-(4-(naphthalene-2-yl)phenyl)-1,3,5-triazine, 16.8 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)benzothiophene, 7.9 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium(0), 70 ml of tetrahydrofuran, and 20 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated monochlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered at 90°C using Celite filtration. The solvent was removed by distillation under reduced pressure, and the resulting mixture was purified by crystallization with monochlorobenzene to obtain compound (42): 7.5 g (yield: 47%).

[0082] The structure of the obtained white powder was identified using NMR. １ H-NMR (CDCl ３ The following 29 hydrogen signals were detected: δ (ppm) = 8.90–8.83 (6H), 8.16 (1H), 8.05 (4H), 7.94–7.82 (6H), 7.62–7.51 (6H), 7.36–7.18 (6H).

[0083]

[0084] [Synthesis Example 4] <Synthesis of Compound (55)> 10.0 g of 2-chloro-4-(4-(naphthalene-2-yl)phenyl)-6-(phenanthrene-9-yl)-1,3,5-triazine, 8.5 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)-1,10-phenanthroline, 4.2 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium(0), 90 ml of tetrahydrofuran, and 30 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated dichlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered at 90°C using Celite filtration. The mixture obtained by removing the solvent under reduced pressure was purified by crystallization with dichlorobenzene to obtain compound (55): 8.3 g (yield: 57%).

[0085] The structure of the obtained white powder was identified using NMR. １ H-NMR (CDCl ３ The following 31 hydrogen signals were detected: δ (ppm) = 9.29 (1H), 9.16 (1H), 9.01 (2H), 8.95 (2H), 8.87–8.78 (3H), 8.60 (2H), 8.38 (1H), 8.30–8.13 (4H), 7.97–7.67 (13H), 7.56–7.52 (2H).

[0086]

[0087] [Synthesis Example 5] <Synthesis of Compound (7)> ​​In a reaction vessel, 3.2 g of 2,4-dichloro-6-phenyl-1,3,5-triazine, 10.0 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]oxazolo[5,4-b]pyridine, 25.8 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 115 ml of tetrahydrofuran, and 13 ml of water were added and the mixture was stirred overnight at 60°C. After confirming that the reaction was complete, methanol was added and the resulting precipitate was filtered off to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour and then filtered. The filtrate was cooled to room temperature and the resulting precipitate was filtered off and washed with acetone to obtain Compound (7): 3.8 g (yield: 50%).

[0088] The structure of the obtained white solid was identified using NMR. １ H-NMR (CDCl ３ The following 19 hydrogen signals were detected: δ (ppm) = 8.97 (4H), 8.82 (2H), 8.52 (4H), 8.42 (2H), 8.14 (2H), 7.64 (3H), 7.41 (2H).

[0089]

[0090] [Synthesis Example 6] <Synthesis of Compound (16)> In a reaction vessel, 4.8 g of 2-chloro-4-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-6-phenyl-1,3,5-triazine, 4.5 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]quinoxaline, 2.8 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 90 ml of tetrahydrofuran, and 10 ml of water were added, and the mixture was stirred at 60°C for 8 hours. After confirming the completion of the reaction, methanol was added, and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was filtered and washed with acetone to obtain Compound (16): 2.5 g (yield: 36%).

[0091] The structure of the obtained pale white solid was identified using NMR. １ H-NMR (CDCl ３ The following 21 hydrogen signals were detected: δ (ppm) = 9.46 (1H), 8.98 (4H), 8.83 (2H), 8.52 (2H), 8.45 (2H), 8.42 (1H), 8.24 (1H), 8.16 (2H), 7.83 (2H), 7.65 (3H), 7.41 (1H).

[0092]

[0093] [Synthesis Example 7] <Synthesis of Compound (33)> In a reaction vessel, 3.6 g of 2,4-dichloro-6-(naphthalene-2-yl)-1,3,5-triazine, 9.2 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]oxazolo[5,4-b]pyridine, 5.4 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 110 ml of tetrahydrofuran, and 10 ml of water were added, and the mixture was stirred at 60°C for 8 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the precipitate was filtered and washed with acetone to obtain Compound (33): 3.8 g (yield: 48%).

[0094] The structure of the obtained pale white solid was identified using NMR. １ H-NMR (CDCl ３ The following 21 hydrogen signals were detected: δ (ppm) = 9.39 (1H), 9.04 (4H), 8.86 (1H), 8.56 (4H), 8.43 (2H), 8.16 (3H), 8.07 (1H), 7.96 (1H), 7.63 (2H), 7.42 (2H).

[0095]

[0096] [Synthesis Example 8] <Synthesis of Compound (36)> 10.3 g of 2-chloro-4,6-bis(4-(naphthalene-2-yl)phenyl)-1,3,5-triazine, 8.3 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)-1,10-phenanthroline, 4.1 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium(0), 93 ml of tetrahydrofuran, and 30 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated monochlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered by Celite. The solvent was removed by distillation under reduced pressure and the resulting mixture was purified by crystallization with monochlorobenzene to obtain compound (36): 7.8 g (yield: 53%).

[0097] The structure of the obtained white powder was identified using NMR. １ H-NMR (CDCl ３ The following 31 hydrogen signals were detected: δ (ppm) = 8.97 (6H), 8.18 (2H), 8.08 (2H), 7.99–7.84 (12H), 7.64–7.51 (6H), 7.36–7.21 (3H).

[0098]

[0099] [Synthesis Example 9] <Synthesis of Compound (37)> 8.0 g of 2-(4-(benzofuran-2-yl)phenyl)-4,6-dichloro-1,3,5-triazine, 12.8 g of (4-(naphthalene-2-yl)phenyl)boronic acid, 8.1 g of potassium carbonate, 0.1 g of tetrakis(triphenylphosphine)palladium(0), 70 ml of tetrahydrofuran, and 20 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated monochlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered by Celite. The solvent was removed by distillation under reduced pressure and the resulting mixture was purified by crystallization with monochlorobenzene to obtain compound (37): 11.7 g (yield: 74%).

[0100] The structure of the obtained white powder was identified using NMR. １ H-NMR (CDCl ３ The following 31 hydrogen signals were detected: δ (ppm) = 8.97 (6H), 8.18 (2H), 8.08 (2H), 7.99–7.84 (12H), 7.64–7.51 (6H), 7.36–7.21 (3H).

[0101]

[0102] [Synthesis Example 10] <Synthesis of Compound (75)> In a reaction vessel, 3.6 g of 2,4-dichloro-6-(naphthalene-1-yl)-1,3,5-triazine, 9.2 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]oxazolo[5,4-b]pyridine, 5.4 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 110 ml of tetrahydrofuran, and 10 ml of water were added, and the mixture was stirred at 50°C for two nights. After confirming that the reaction was complete, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the precipitate was filtered and washed with acetone to obtain Compound (75): 3.8 g (yield: 49%).

[0103] The structure of the obtained white solid was identified using NMR. １ H-NMR (CDCl ３ The following 21 hydrogen signals were detected: δ (ppm) = 9.16 (1H), 9.00 (4H), 8.60 (1H), 8.54 (4H), 8.43 (2H), 8.14 (3H), 8.02 (1H), 7.72 (2H), 7.63 (1H), 7.42 (2H).

[0104]

[0105] [Synthesis Example 11] <Synthesis of Compound (82)> In a reaction vessel, 4.8 g of 2-chloro-4-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-6-phenyl-1,3,5-triazine, 4.3 g of 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)pyrimidyl]naphthalene, 2.7 g of potassium carbonate, 288 mg of tetrakis(triphenylphosphine)palladium(0), 90 ml of tetrahydrofuran, and 10 ml of water were added, and the mixture was stirred at 60°C for 8 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (82): 4.6 g (yield: 75%).

[0106] The structure of the obtained pale white solid was identified using NMR. １ H-NMR (CDCl ３ The following 21 hydrogen signals were detected: δ (ppm) = 10.08 (2H), 9.18 (1H), 8.97 (2H), 8.81 (2H), 8.69 (1H), 8.53 (2H), 8.43 (1H), 8.15 (1H), 8.07 (1H), 8.02 (1H), 7.92 (1H), 7.63 (5H), 7.42 (1H).

[0107]

[0108] [Synthesis Example 12] <Synthesis of Compound (89)> In a reaction vessel, 3.4 g of 2-chloro-4-(naphthalene-2-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.7 g of 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)pyrimidine-2-yl]naphthalene, 1.7 g of potassium carbonate, 0.2 g of tetrakis(triphenylphosphine)palladium(0), 60 ml of tetrahydrofuran, and 6 ml of water were added, and the mixture was stirred at 60°C for 4 hours. After confirming that the reaction was complete, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (89): 4.6 g (yield: 97%).

[0109] The structure of the obtained pale yellow solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 10.12 (2H), 9.36 (1H), 9.18 (1H), 9.00 (2H), 8.82 (1H), 8.70 (1H), 8.54 (2H), 8.43 (1H), 8.14 (2H), 8.06 (2H), 8.01 (1H), 7.94 (2H), 7.60 (4H), 7.42 (1H).

[0110]

[0111] [Synthesis Example 13] <Synthesis of Compound (101)> In a reaction vessel, 3.2 g of 2-chloro-4-(naphthalene-1-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.6 g of 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)pyrimidyl]naphthalene, 1.6 g of potassium carbonate, 120 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 60 ml of tetrahydrofuran, and 6 ml of water were added, and the mixture was stirred at 60°C for 4 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (101): 3.7 g (yield: 83%).

[0112] The structure of the obtained pale white solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 10.09 (2H), 9.20 (2H), 8.97 (2H), 8.69 (1H), 8.63 (1H), 8.53 (2H), 8.42 (1H), 8.14 (2H), 8.06 (1H), 8.01 (2H), 7.91 (1H), 7.71 (2H), 7.60 (3H), 7.41 (1H).

[0113]

[0114] [Synthesis Example 14] <Synthesis of Compound (104)> In a reaction vessel, 3.2 g of 2-chloro-4-(naphthalene-1-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.6 g of 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)pyrimidyl]naphthalene, 1.6 g of potassium carbonate, 120 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 60 ml of tetrahydrofuran, and 6 ml of water were added, and the mixture was stirred at 60°C for 3 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, the mixture was stirred for 1 hour, and then filtered. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (104): 3.7 g (yield: 82%).

[0115] The structure of the obtained pale yellow solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 10.20 (2H), 9.23 (1H), 9.00 (2H), 8.92 (1H), 8.67 (1H), 8.56 (2H), 8.43 (1H), 8.34 (1H), 8.16 (2H), 8.04 (2H), 7.97 (1H), 7.67 (6H), 7.42 (1H).

[0116]

[0117] [Synthesis Example 15] <Synthesis of Compound (105)> In a reaction vessel, 3.5 g of 2-chloro-4-(naphthalene-1-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.8 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]quinoxaline, 1.7 g of potassium carbonate, 0.1 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 60 ml of tetrahydrofuran, and 6 ml of water were added and stirred overnight. After confirming the completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and after stirring for 1 hour, the mixture was filtered. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (105): 4.1 g (yield: 85%).

[0118] The structure of the obtained pale yellow solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 9.47 (1H), 9.19 (1H), 9.01 (4H), 8.61 (1H), 8.54 (2H), 8.47 (2H), 8.42 (1H), 8.24 (1H), 8.16 (3H), 8.02 (1H), 7.83 (2H), 7.71 (2H), 7.64 (1H), 7.42 (1H).

[0119]

[0120] [Synthesis Example 16] <Synthesis of Compound (106)> In a reaction vessel, 14.9 g of 2-chloro-4-(naphthalen-2-yl)-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine, 11.2 g of 2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)quinoxaline, 9.3 g of potassium carbonate, 0.8 g of tetrakis(triphenylphosphine)palladium(0), 75 ml of toluene, 40 ml of ethanol, and 30 ml of water were added, and the mixture was stirred overnight under heating reflux. After confirming the completion of the reaction, methanol was added, and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated dichlorobenzene, silica gel was added, and the mixture was stirred for 30 minutes, followed by Celite filtration. The solvent was removed by vacuum distillation, and the resulting mixture was purified by crystallization with gyrolobenzene to obtain compound (106): 12.8 g (yield: 62%).

[0121] The same molecular weight was detected in the obtained white powder using LC-MS. MS[M+H] ＋ = 614

[0122]

[0123] [Synthesis Example 17] <Synthesis of Compound (108)> In a reaction vessel, 4.8 g of 2-chloro-4-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-6-phenyl-1,3,5-triazine, 4.3 g of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]quinoline, 2.7 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 90 ml of tetrahydrofuran, and 10 ml of water were added, and the mixture was stirred at 60°C for 8 hours. After confirming the completion of the reaction, methanol was added, and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and after stirring for 1 hour, the mixture was filtered. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (108): 5.0 g (yield: 73%).

[0124] The structure of the obtained pale white solid was identified using NMR. １H-NMR (CDCl ３ 3) detected signals of the following 22 hydrogens. δ (ppm) = 9.30 (1H), 8.97 (4H), 8.83 (2H), 8.52 (2H), 8.43 (2H), 8.19 (1H), 8.14 (1H), 7.96 (3H), 7.78 (1H), 7.64 (4H), 7.41 (1H).

[0125]

[0126] [Synthesis Example 18] <Synthesis of Compound (110)> 4.0 g of 2-chloro-4-[4-(oxazolo[5,4-b]pyridin-2-yl)phenyl]-6-phenyl-1,3,5-triazine, 3.6 g of 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline, 2.3 g of potassium carbonate, 0.2 g of tetrakis(triphenylphosphine)palladium(0), 50 ml of tetrahydrofuran, and 5 ml of water were added to a reaction vessel and stirred at 60 °C for 3 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature and the resulting precipitate was collected by filtration to obtain a crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and after stirring for 1 hour, filtration was performed. The filtrate was cooled to room temperature and the resulting precipitate was collected by filtration and washed with acetone to obtain 5.9 g (yield: 99%) of Compound (110).

[0127] The structure of the obtained pale white solid was identified using NMR.[[ID= (12]] １ H-NMR (CDCl ３ 3) detected signals of the following 21 hydrogens. δ (ppm) = 9.57 (1H), 9.44 (1H), 9.13 (1H), 8.98 (2H), 8.83 (2H), 8.49 (2H), 8.41 (1H), 8.32 (1H), 8.27 (2H), 8.13 (1H), 7.61 (6H), 7.40 (1H).

[0128]

[0129] [Synthesis Example 19] <Synthesis of Compound (111)> In a reaction vessel, 4.0 g of 2-chloro-4-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-6-phenyl-1,3,5-triazine, 4,4,5,5-tetramethyl-2-[2-(naphthalene-2-yl)quinoxaline-6-yl]-1,3,2-dioxaborane, 2.3 g of potassium carbonate, 0.2 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 50 ml of tetrahydrofuran, and 5 ml of water were added, and the mixture was stirred under reflux for 3 hours. After confirming the completion of the reaction, water was added, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 30 minutes, followed by hot filtration. By filtering the precipitate obtained from the filtrate, compound (111): 5.6 g (yield: 89%) was obtained.

[0130] The structure of the obtained yellow powder was identified using NMR. １ The following 23 hydrogen signals were detected by 1H-NMR (CDCl3): δ (ppm) = 9.63–9.65 (2H), 9.20 (1H), 9.04 (2H), 8.88 (2H), 8.77 (1H), 8.54 (2H), 8.39–8.47 (3H), 8.15 (1H), 8.07 (2H), 7.94 (1H), 7.60–7.69 (5H), 7.42 (1H).

[0131]

[0132] [Synthesis Example 20] <Synthesis of Compound (113)> In a reaction vessel, 3.4 g of 2-chloro-4-(naphthalene-2-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.7 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]quinoxaline, 1.7 g of potassium carbonate, 0.2 g of tetrakis(triphenylphosphine)palladium (0), 60 ml of tetrahydrofuran, and 6 ml of water were added, and the mixture was stirred at 50°C for 23 hours. After confirming that the reaction was complete, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (113): 4.0 g (yield: 84%).

[0133] The structure of the obtained white solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 9.47 (1H), 9.38 (1H), 9.03 (4H), 8.86 (1H), 8.54 (2H), 8.47 (2H), 8.42 (1H), 8.24 (1H), 8.16 (3H), 8.06 (1H), 7.95 (1H), 7.83 (2H), 7.61 (2H), 7.41 (1H).

[0134]

[0135] [Synthesis Example 21] <Synthesis of Compound (114)> In a reaction vessel, 2.7 g of 2-chloro-4-(naphthalene-2-yl)-6-[4-(oxazolo[5,4-b]pyridine-2-yl)phenyl]-1,3,5-triazine, 2.4 g of 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)quinoxaline, 1.5 g of potassium carbonate, 156 mg of tetrakis(triphenylphosphine)palladium (0), 50 ml of tetrahydrofuran, and 5 ml of water were added, and the mixture was stirred at 60°C for 16 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 1 hour, followed by filtration. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain compound (114): 2.4 g (yield: 59%).

[0136] The structure of the obtained white solid was identified using NMR. １ H-NMR (CDCl ３ The following 23 hydrogen signals were detected: δ (ppm) = 9.62 (1H), 9.45 (1H), 9.39 (1H), 9.20 (1H), 9.03 (2H), 8.87 (1H), 8.52 (2H), 8.42 (1H), 8.36 (1H), 8.28 (2H), 8.15 (2H), 8.04 (1H), 7.93 (1H), 7.60 (5H), 7.41 (1H).

[0137]

[0138] [Synthesis Example 22] <Synthesis of Compound (115)> In a reaction vessel, 2-chloro-4-(naphthalen-2-yl)-6-[4-(oxazolo[5,4-b]pyridin-2-yl)phenyl]-1,3,5-triazine: 2.7 g, 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]naphthalene: 2.1 g, potassium carbonate: 1.3 g, tetrakis(triphenylphosphine)palladium(0): 0.1 g, tetrahydrofuran: 45 ml, and water: 5 ml were added, and the mixture was stirred at 60 °C for 4 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting precipitate was collected by filtration to obtain a crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and after stirring for 1 hour, filtration was performed. The filtrate was cooled to room temperature, and the resulting precipitate was collected by filtration and washed with acetone to obtain 2.0 g (yield: 55%) of Compound (115).

[0139] The structure of the obtained white solid was identified using NMR. １ H-NMR (CDCl ３ ) detected the following 23 hydrogen signals. δ (ppm) = 10.20 (2H), 9.37 (1H), 9.01 (2H), 8.94 (1H), 8.83 (1H), 8.55 (2H), 8.43 (1H), 8.34 (1H), 8.14 (2H), 8.06 (2H), 7.96 (2H), 7.63 (5H), 7.42 (1H).

[0140]

[0141] [Synthesis Example 23] <Synthesis of Compound (116)> In a reaction vessel, 1.3 g of 2,4-dichloro-6-phenyl-1,3,5-triazine, 4,4,5,5-tetramethyl-2-[2-(naphthalene-2-yl)pyrimidine-5-yl]-1,3,2-dioxaborane, 4.0 g of potassium carbonate, 4.6 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 15 ml of tetrahydrofuran, and 2 ml of water were added and the mixture was stirred under reflux for 3 hours. After confirming the completion of the reaction, the precipitate was filtered off to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added and the mixture was stirred for 30 minutes, followed by hot filtration. By filtering off the precipitate obtained from the filtrate, 2.2 g of Compound (116) (yield: 71%) was obtained.

[0142] The structure of the obtained pale yellow powder was identified using NMR. １ The following 23 hydrogen signals were detected by 1H-NMR (CDCl3): δ (ppm) = 10.07 (4H), 9.20 (2H), 8.80 (2H), 8.70 (2H), 8.08 (2H), 8.02 (2H), 7.93 (2H), 7.57–7.67 (7H).

[0143]

[0144] [Synthesis Example 24] <Synthesis of Compound (117)> In a reaction vessel, 3.0 g of 2,4-di(naphthalene-2-yl)-6-chloro-1,3,5-triazine, 3.3 g of 4,4,5,5-tetramethyl-2-[2-(naphthalene-2-yl)-pyrimidine-5-yl]-1,3,2-dioxaborane, 1.7 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 50 ml of toluene, 5 ml of ethanol, and 10 ml of water were added, and the mixture was stirred under reflux for 2 hours. After confirming the completion of the reaction, the precipitate was filtered off to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 30 minutes, followed by hot filtration. By filtering off the precipitate obtained from the filtrate, 4.2 g of Compound (117) (yield: 96%) was obtained.

[0145] The structure of the obtained pale yellow powder was identified using NMR. １ The following 23 hydrogen signals were detected by 1H-NMR (CDCl3): δ (ppm) = 10.12 (2H), 9.36 (2H), 9.17 (1H), 8.83 (2H), 8.69 (1H), 8.00–8.13 (6H), 7.91–7.96 (3H), 7.56–7.64 (6H).

[0146]

[0147] [Synthesis Example 25] <Synthesis of Compound (118)> In a reaction vessel, 1.5 g of 2,4-dichloro-6-(naphthalene-2-yl)-1,3,5-triazine, 4,4,5,5-tetramethyl-2-[2-(naphthalene-2-yl)pyrimidine-5-yl]-1,3,2-dioxaborane, 4.0 g of potassium carbonate, 4.6 g of tetrakis(triphenylphosphine)palladium(0), 30 ml of tetrahydrofuran, and 4 ml of water were added and the mixture was stirred under reflux for 3 hours. After confirming the completion of the reaction, the precipitate was filtered off to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added and the mixture was stirred for 30 minutes, followed by hot filtration. By filtering off the precipitate obtained from the filtrate, 2.3 g of Compound (118) (yield: 68%) was obtained.

[0148] The structure of the obtained pale yellow powder was identified using NMR. １ The following 25 hydrogen signals were detected by 1H-NMR (CDCl3): δ (ppm) = 10.06 (4H), 9.32 (2H), 9.18 (4H), 8.75 (2H), 8.12 (2H), 8.07 (2H), 7.98 (5H), 7.66 (4H).

[0149]

[0150] [Synthesis Example 26] <Synthesis of Compound (119)> In a reaction vessel, 3.0 g of 2,4-di(naphthalene-2-yl)-6-chloro-1,3,5-triazine, 3.3 g of 4,4,5,5-tetramethyl-2-(2-phenyl-quinoxaline-6-yl)-1,3,2-dioxaborane, 1.7 g of potassium carbonate, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 50 ml of toluene, 5 ml of ethanol, and 10 ml of water were added, and the mixture was stirred under reflux for 2 hours. After confirming the completion of the reaction, the precipitate was filtered off to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, activated clay was added, and the mixture was stirred for 30 minutes, followed by hot filtration. By filtering off the precipitate obtained from the filtrate, 4.1 g of Compound (119) (yield: 94%) was obtained.

[0151] The structure of the obtained pale yellow powder was identified using NMR. １ H-NMR (DMSO-D ６ The following 23 hydrogen signals were detected: δ (ppm) = 9.68 (1H), 9.45 (3H), 9.25 (1H), 8.92 (2H), 8.38 (1H), 8.30 (2H), 8.16–8.18 (2H), 8.06 (2H), 7.95–7.97 (2H), 7.59–7.65 (7H).

[0152]

[0153] [Synthesis Example 27] <Synthesis of Compound (122)> 16.0 g of 2-(4-chloro-6-(naphthalene-2-yl)-1,3,5-triazine-2-yl)-6-phenylquinoxaline, 13.3 g of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl)benzothiazole, 9.9 g of potassium carbonate, 0.8 g of tetrakis(triphenylphosphine)palladium(0), 110 ml of tetrahydrofuran, and 50 ml of water were added to a reaction vessel and stirred overnight under reflux. After confirming the completion of the reaction, methanol was added and the resulting precipitate was filtered to obtain the crude product. The obtained crude product was dissolved in heated 1,2-dichlorobenzene, silica gel was added, and after stirring for 30 minutes, it was filtered by Celite. The mixture obtained by removing the solvent under reduced pressure was purified by crystallization with dylolobenzene to obtain compound (122): 12.5 g (yield: 56%).

[0154] The same molecular weight was detected in the obtained white powder using LC-MS. MS [M] ＋ = 620

[0155]

[0156] [Example 1] (Measurement of melting point and glass transition temperature) The melting point and glass transition temperature (Tg) of compound (39) obtained in Synthesis Example 1 were measured using a high-sensitivity differential scanning calorimeter (Bruker AXS, model: DSC3100SA). The measurement results are shown in Table 1.

[0157] (Measurement of refractive index and extinction coefficient) For the compound (39) obtained in Synthesis Example 1, a vapor-deposited film with a thickness of 80 nm was prepared on a silicon substrate, and the refractive index n and extinction coefficient k were measured at room temperature (25 ± 2°C) at wavelengths of 450 nm and 750 nm using a spectroscopic measuring device (Filmetrics, Model: F10-RT-UV). The measurement results, along with the deposition temperature, are shown in Table 2.

[0158] (Measurement of luminescence characteristics and device life of organic EL elements) As an example, the organic EL element of the present invention is constructed as shown in Figure 1, in which a reflective ITO electrode is pre-formed as a transparent anode 2 on a glass substrate 1, and then an organic EL element is fabricated by depositing 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, a cathode 8, and a capping layer 9 in that order.

[0159] Specifically, a glass substrate 1, on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were sequentially deposited, was ultrasonically cleaned in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250°C for 10 minutes. After that, UV ozone treatment was performed for 2 minutes, and then this ITO-coated glass substrate was placed in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, a hole injection layer 3 was formed covering the transparent anode 2 by binary deposition of an electron acceptor (Acceptor-1) with the following structural formula and a compound (HTM-1) with the following structural formula, at a deposition rate ratio of Acceptor-1:compound (HTM-1) = 3:97, to a thickness of 10 nm.

[0160] On the hole injection layer 3 described above, a hole transport layer 4 was formed using a compound with the following structural formula (HTM-1) to a thickness of 140 nm. On this hole transport layer 4, a light-emitting layer 5 was formed using a binary deposition method with a deposition rate ratio of (EMD-1):(EMH-1) = 5:95, by compound EMD-1 and compound EMH-1, to a thickness of 20 nm. On this light-emitting layer 5, an electron transport layer 6 was formed using a binary deposition method with a deposition rate ratio of (ETM-1):(ETM-2) = 50:50, by compound ETM-1 and compound ETM-2, to a thickness of 30 nm. On this electron transport layer 6, a lithium fluoride layer was formed as an electron injection layer 7 to a thickness of 1 nm. On this electron injection layer 7, a magnesium-silver alloy layer was formed as a cathode 8 to a thickness of 12 nm. Finally, the compound (88) from Synthesis Example 1 was formed as a capping layer 9 to a thickness of 60 nm.

[0161]

[0162] The luminescence characteristics of the fabricated organic EL elements were measured by applying a DC voltage in air at room temperature (current density: 10 mA / cm²). ２ ). Furthermore, the device lifetime was measured using the fabricated organic EL element. In this invention, the device lifetime is defined as a current density of 10 mA / cm². ２ The time taken for the brightness to decay to 95% of the initial brightness (100%) when driven with a constant current was defined as the time it took for the brightness to decrease. The measurement results are summarized in Table 3.

[0163] [Examples 2-44] (Measurement of Melting Point and Glass Transition Temperature) In Example 1, the melting point and glass transition temperature (Tg) were measured in the same manner as in Example 1, except that the compounds obtained in Synthesis Examples 2-27 were used instead of compound (39) from Synthesis Example 1, as shown in Table 1. The measurement results are summarized in Table 1.

[0164] (Measurement of refractive index and extinction coefficient) In Example 1, the refractive index n and extinction coefficient k at wavelengths of 450 nm and 750 nm were measured using the same method as in Example 1, except that the compounds obtained in Synthesis Examples 2 to 27 were used instead of compound (39) in Synthesis Example 1, as shown in Table 2. The measurement results, along with the deposition temperature, are summarized in Table 2.

[0165] (Measurement of Luminous Emission Characteristics and Device Lifetime of Organic EL Devices) In Example 1, organic EL devices were fabricated under the same conditions as in Example 1, except that the compounds obtained in Synthesis Examples 2 to 27 were used as the capping layer 9, as shown in Table 3, instead of the compound (39) from Synthesis Example 1. The luminous emission characteristics and device lifetime of the fabricated organic EL devices were measured using the same method as in Example 1. The measurement results are summarized in Table 3.

[0166] [Comparative Example 1] (Measurement of refractive index and extinction coefficient) For comparison, in Example 1, instead of compound (39) of Synthesis Example 1, Alq was used as shown in Table 2. ３ Except for the use of [specific material], the refractive index n and extinction coefficient k at wavelengths of 450 nm and 750 nm were measured using the same method. The measurement results, along with the deposition temperature, are summarized in Table 2.

[0167] (Measurement of luminescence characteristics and device lifetime of organic EL elements) For comparison, in Example 1, instead of the compound (88) of Synthesis Example 1 as the capping layer 9, Alq was used as shown in Table 3. ３ Except for the use of [specific material], organic EL elements were fabricated using the same method. The luminescence characteristics and element lifetime of the fabricated organic EL elements were measured using the same method as in Example 1. The measurement results are summarized in Table 3.

[0168]

[0169] The results shown in Table 1 indicate that the compounds obtained in Synthesis Examples 1 to 27 have high melting points and either lack a glass transition temperature or have a glass transition temperature of 100°C or higher. This indicates that the thin film state is stable and has excellent durability.

[0170]

[0171] As shown in Table 2, in the wavelength range of 450 nm to 750 nm, the triazine compound of the present invention is Alq ３ The extinction coefficient and refractive index of the present invention are equal to or greater than those of the present invention, and by using the triazine compound of the present invention as a constituent material of the capping layer, the light extraction efficiency in organic EL elements can be improved.

[0172]

[0173] As shown in Table 3, the current density is 10 mA / cm². ２ While the driving voltage was almost the same for the organic EL element of Comparative Example 1 and the organic EL elements of Examples 1 to 27, the brightness, luminous efficiency, and power efficiency showed significant improvements in all examples' organic EL elements compared to the comparative example's organic EL element. This indicates that the triazine compound of the present invention is a suitable material for use in the capping layer, and that increasing the refractive index of the capping layer can significantly improve the light extraction efficiency of the organic EL element.

[0174] The triazine compound of the present invention has a high refractive index, significantly improves light extraction efficiency, and maintains a stable thin film state, making it an excellent compound for use in organic EL elements. Furthermore, organic EL elements fabricated using the triazine compound of the present invention can achieve high efficiency. Moreover, using the compound of the present invention, which does not absorb in the blue, green, and red wavelength regions, is particularly suitable when displaying images with high color purity, clarity, and brightness. For example, it is expected to be used in applications such as home appliances and lighting.

[0175] 1. Glass substrate 2. Transparent anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6. Electron transport layer 7. Electron injection layer 8. Cathode 9. Capping layer

Claims

1. A triazine compound represented by the following general formula (I). (In the formula, Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Ar ３ L represents a group selected from the group consisting of substituted or unsubstituted pyrimidinyl, quinolyl, quinoxalinyl, benzofuranyl, benzothienyl, phenanthrolinyl, dibenzothienyl, oxazolopyridyl, and benzothiazolyl groups. １ , L ２ and L ３ Each of these independently represents a single bond, or a substituted or unsubstituted arylene group.

2. Ar １ However, it is a substituted or unsubstituted aryl group, Ar ２ The triazine compound according to claim 1, wherein the group is selected from a substituted or unsubstituted naphthyl group, pyrimidinyl group, quinolyl group, quinoxalinyl group, benzofuranyl group, benzothienyl group, phenanthrolinyl group, dibenzothienyl group, oxazolopyridyl group, benzothiazolyl group, and pyridyl group.

3. Ar ３ is a group selected from a substituted 5-pyridyl group, a substituted 5-pyrimidinyl group, and a substituted 6-quinoxalinyl group, which has an unsubstituted 3-quinolyl group, 2-quinoxalinyl group, 2-benzofuranyl group, 2-benzothienyl group, 2-[1,10]phenanthrolinyl group, 2-dibenzothienyl group, 2-oxazolo[5,4-b]pyridyl group, 2-benzothiazolyl group, phenyl group or naphthyl group as a substituent, the triazine compound according to claim 1.

4. The triazine compound according to any one of claims 1 to 3, wherein the deposited film, vacuum deposited on a silicon substrate to a thickness of 80 nm, has a refractive index of 1.70 or higher in the wavelength range of 450 nm to 750 nm, measured at room temperature (25 ± 2°C).

5. An organic electroluminescent element having at least an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode, and a capping layer in this order, wherein the capping layer contains the triazine compound described in claim 4.

6. An electronic element having a pair of electrodes and at least one organic layer, wherein the organic layer contains the triazine compound described in any one of claims 1 to 3.

7. An electronic device comprising the electronic element described in claim 6.

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