Compounds and organic electroluminescent elements using the same

Abstract

The present invention provides a high-performance organic EL element and a compound capable of realizing said organic EL element. [Solution] A compound represented by the following formula (1). TIFF2026104050000023.tif67170

Description

[Technical Field]

[0001] This invention relates to a novel compound and an organic electroluminescent device using the same. [Background technology]

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter also called an organic EL element), holes are injected from the anode and electrons from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Conventional organic EL elements still lacked sufficient performance. While improvements to the materials used in organic EL elements are gradually being made to enhance performance (Patent Document 1), further performance improvements are required. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2022 / 264827 [Overview of the project] [Problems that the invention aims to solve]

[0005] The object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing said organic EL element. [Means for solving the problem]

[0006] According to the present invention, the following compounds and the like are provided. 1. A compound represented by the following formula (1). [ka] (In formula (1), L1 and L2 are each independently groups represented by one of the following formulas (a1) to (a13). [Chemical formula] In formulas (a1) to (a13), One of the two * represents a benzene anthracene skeleton in formula (1) or a single bond connecting to L1, and the other of the two * represents a triazine skeleton in formula (1) or a single bond connecting to L2. R a1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 10 ring-forming carbon atoms. Multiple Rs a1 may be the same as or different from each other. R 11 and R 12 One of them represents a single bond connecting to L1. Rs that do not represent the single bond 11 and R 12 , as well as R1 to R 10 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms. R 21 ~R 30 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 10 ring-forming carbon atoms.) 2. A cathode, an anode, one or more organic layers disposed between the cathode and the anode, having at least one of the organic layers contains the compound described in 1 above, an organic electroluminescence device.

Advantages of the Invention

[0007] According to the present invention, a high-performance organic EL element and a compound capable of realizing the organic EL element can be provided. [Brief explanation of the drawing]

[0008] [Figure 1] This figure shows a schematic configuration of an organic EL element according to one aspect of the present invention. [Modes for carrying out the invention]

[0009] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium and deuterium.

[0010] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated are assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms and deuterium atoms.

[0011] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0012] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0013] [Novel compounds] A compound according to one aspect of the present invention is a compound represented by formula (1), which will be described later.

[0014] A compound according to one aspect of the present invention can improve the performance of an organic EL element when used in such an element.

[0015] [Compound represented by formula (1)] A compound according to one aspect of the present invention is represented by the following formula (1). [ka] (In formula (1), L1 and L2 are each independently groups represented by one of the following formulas (a1) to (a13). [ka] In formulas (a1) to (a13), One of the two asterisks represents a single bond that connects to the benzanthracene skeleton or L1 in formula (1), and the other of the two asterisks represents a single bond that connects to the triazine skeleton or L2 in formula (1). R a1 teeth, hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, These are substituted or unsubstituted cycloalkyl groups with 5 to 10 carbon atoms forming a ring. Multiple R a1 They may be the same or different from each other. R 11 and R 12 One of these represents a single bond connecting with L1. R that does not represent the single bond 11 and R 12 , and R1~R 10 Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms. R 21 ~R 30 Each of them operates independently. hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, (It is a substituted or unsubstituted cycloalkyl group with 5 to 10 carbon atoms forming a ring.)

[0016] In the groups represented by formulas (a1) to (a13), either of the two *s represents a single bond attached to the benzanthracene skeleton or L1, while the * that does not attach to the benzanthracene skeleton or L1 represents a single bond attached to the triazine skeleton or L2. That is, for example, if L1 is the group represented by formula (a1) and L2 is the group represented by formula (a4), the compound represented by formula (1) will have one of the structures of the compounds represented by the following formulas (E1) to (E4). [ka]

[0017] Multiple R a1 Of these, one or more pairs of adjacent elements do not bond to each other and do not form substituted or unsubstituted monorings or fused rings. R1~R 10 Of these, one or more pairs of adjacent elements do not bond to each other and do not form substituted or unsubstituted monorings or fused rings. R 21 ~R 30 Of these, one or more pairs of adjacent elements do not bond to each other and do not form substituted or unsubstituted monorings or fused rings.

[0018] In one embodiment, L1 is A base represented by formula (a1), or It is a base represented by formula (a6).

[0019] In one embodiment, L2 is A base represented by formula (a1), or It is a base represented by formula (a3).

[0020] In one embodiment, R a1 This is a hydrogen atom.

[0021] In one embodiment, R 11 This represents a single bond connecting with L1. In one embodiment, R 12 This represents a single bond connecting with L1.

[0022] In one embodiment, R does not represent a single bond. 11 and R 12 , and R1~R 10 This is a hydrogen atom. In one embodiment, R does not represent a single bond. 11 and R 12 is an unsubstituted phenyl group, and R1~R 10 This is a hydrogen atom.

[0023] In one embodiment, R 21 ~R 30 This is a hydrogen atom.

[0024] In one embodiment, the compound represented by formula (1) is represented by the following formula (1-1). [ka] (In formula (1-1), L1, L2, R1~R 11 , and R 21 ~R 30 This is as defined in equation (1) above.

[0025] In one embodiment, the compound represented by formula (1) can be represented by any of the following formulas (1-11) to (1-13). [ka] (In formulas (1-11) to (1-13), R1 to R 12 , R 21 ~R 30 , and R a1 This is as defined in equation (1) above.

[0026] In one embodiment, the C1-C6 alkyl group in formula (1) is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, or an n-hexyl group.

[0027] In one embodiment, the ring-forming cycloalkyl group having 5 to 10 carbon atoms in formula (1) is a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a norbornyl group, or an adamantyl group.

[0028] In one embodiment, the ring-forming aryl group having 6 to 14 carbon atoms in formula (1) is a phenyl group, a naphthyl group, a biphenylyl group, a fluorenyl group, or a phenantrenyl group.

[0029] In one embodiment, the substituted ring-forming aryl group having 6 to 14 carbon atoms in formula (1) is a terphenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a naphthylphenyl group, or a phenylnaphthyl group.

[0030] In one embodiment, the substituent in the phrase "substituted or unsubstituted" in formula (1) is: C1-C6 alkyl group (preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, or tert-butyl group) A C1-C6 haloalkyl group (preferably trifluoromethyl, 2,2,2-tolufluoroethyl, pentafluoroethyl, or 1,1,1,3,3,3-hexafluoroisopropyl), Alkenyl groups having 2 to 6 carbon atoms (preferably vinyl groups or propenyl groups), A cycloalkyl group having 5 to 10 carbon atoms that forms a ring (preferably a cyclopentyl group, cyclohexyl group, cycloheptyl group, norbornyl group, or adamantyl group), Halogen atoms (preferably fluorine atoms, chlorine atoms, or bromine atoms), Cyano group, and A ring-forming aryl group having 6 to 14 carbon atoms (preferably 6 to 13, more preferably 6 to 12, and even more preferably 6 to 10) (preferably a phenyl group, naphthyl group, biphenylyl group, or phenantrenyl group) It is selected from the group consisting of the following.

[0031] The compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions or starting materials suited to the target product.

[0032] The following are specific examples of compounds according to one aspect of the present invention, but these are merely illustrative examples, and the compounds according to one aspect of the present invention are not limited to the following examples.

[0033] [ka] [ka] [ka] [ka]

[0034] [Materials for organic electroluminescent devices] A compound according to one aspect of the present invention is useful as a material for organic EL devices, and for example, is useful as a material used in the electron transport band of an organic EL device.

[0035] [Organic EL element] An organic EL element according to one aspect of the present invention will be described. An organic EL element according to one aspect of the present invention comprises a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound according to one aspect of the present invention.

[0036] An organic EL element according to one aspect of the present invention can improve performance by having the above configuration.

[0037] A schematic configuration of an organic EL element according to one aspect of the present invention will be described with reference to Figure 1. In one embodiment, an organic EL element 1 according to one aspect of the present invention comprises a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. Organic layer 4 and organic layer 6 may each be a single layer or consist of multiple layers. In one embodiment, an organic EL element according to one aspect of the present invention includes an anode, a light-emitting layer, an electron transport band, and a cathode in this order, wherein at least one layer in the electron transport band contains a compound according to one aspect of the present invention.

[0038] (Electron transport band) The electron transport band is a collective term for one or more layers placed between the light-emitting layer and the cathode. The electron transport band may consist of, for example, layers called a hole blocking layer, an electron transport layer, and an electron injection layer, starting from the light-emitting layer side, and may be a laminated structure including all of these layers, or a layer configuration including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers; for example, two electron transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or it may be formed using two or more types of materials in combination.

[0039] In one embodiment, the electron transport band has at least a first layer (also called a "hole blocking layer" or "first electron transport layer") and a second layer (also called an "electron transport layer" or "second electron transport layer") in this order from the side of the light-emitting layer. The second layer comprises a compound according to one aspect of the present invention.

[0040] In one embodiment, the second layer consists substantially of only the compound according to one aspect of the present invention. "Substantially consisting only of compounds according to one aspect of the present invention" means that the second layer contains no other components at all, or contains other components in trace amounts that do not impair the effects of the present invention. For example, this state applies when other components are present as unavoidable impurities.

[0041] (Other configurations of organic EL elements) An organic EL element according to one aspect of the present invention comprises a cathode, an anode, and one or more organic layers disposed between the cathode and the anode. As long as at least one of the organic layers contains a compound according to one aspect of the present invention, conventionally known materials and element configurations can be applied without impairing the effects of the present invention.

[0042] A typical device configuration for this organic EL element is one in which the following structures are stacked on a substrate. (1) Anode / Emitting layer / Electron transport band / Cathode (2) Anode / Hole transport band / Emitting layer / Electron transport band / Cathode (The " / " indicates that each layer is stacked adjacent to another.)

[0043] (Hole transport band) The hole transport band is a collective term for one or more layers placed between the anode and the light-emitting layer. The hole transport band is composed of, for example, layers called an electron blocking layer, a hole transport layer, and a hole injection layer, which will be described later, starting from the light-emitting layer side. It may be a laminated structure including all of these layers, or it may be a layer configuration of only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers; for example, two types of hole transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or it may be formed using two or more types of materials in combination.

[0044] The following describes the element configuration and materials constituting each layer of an organic EL element according to one aspect of the present invention.

[0045] (substrate) The substrate is used as a support for the light-emitting element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.

[0046] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium zinc oxide, indium tin oxide containing silicon or silicon oxide, indium oxide containing zinc oxide, tungsten oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[0047] (Hole injection layer) The hole injection layer is a layer containing a material with high hole injection properties. Suitable materials with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, electron-withdrawing (acceptor) compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.).

[0048] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other substances may be used as long as they have higher hole transport properties than electron transport properties. Furthermore, the layer containing the substance with high hole transport properties may be a single layer, or it may be a layer of two or more layers made of the above substances stacked together.

[0049] (Guest material for the luminescent layer) The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as highly luminescent substances, fluorescent compounds that emit fluorescence and phosphorescent compounds that emit phosphorescence can be used. Fluorescent compounds are compounds that can emit light from a singlet excited state, and phosphorescent compounds are compounds that can emit light from a triplet excited state. As blue fluorescent materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. As green fluorescent materials that can be used in the light-emitting layer, aromatic amine derivatives, etc., can be used. As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc., can be used. Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Iridium complexes and the like are used as green phosphorescent materials that can be used in the light-emitting layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer.

[0050] (Host material for the light-emitting layer) The light-emitting layer may be configured by dispersing the highly luminescent substance (guest material) described above in another substance (host material). Various materials can be used to disperse the highly luminescent substance, but it is preferable to use a material that has a lower least unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the highly luminescent substance. The following materials are used as host materials for dispersing highly luminescent substances: 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0051] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. In addition to the compound represented by formula (1) above, the electron transport layer can also contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds.

[0052] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer may contain compounds usable in the electron transport layer as described above, as well as metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinolinolatolithium (Liq), and lithium oxide (LiO2). x Alkali metals, alkaline earth metals, or compounds thereof can be used.

[0053] (cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0054] (Electron blocking layer, hole blocking layer, exciton blocking layer) An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc., may be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer. A hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer is a layer that prevents excitons generated in the light-emitting layer from diffusing to adjacent layers, thereby confining the excitons within the light-emitting layer.

[0055] In one embodiment of the organic EL element of the present invention, the method for forming each layer is not particularly limited. Conventional known formation methods such as vacuum deposition and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or coating methods such as dipping with a solution dissolved in a solvent, spin coating, casting, bar coating, and roll coating.

[0056] In one embodiment of the organic EL element of the present invention, the thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency, a range of several nm to 1 μm is usually preferred.

[0057] One embodiment of the electronic device of the present invention comprises the above-described organic electroluminescent element. Specific examples of the electronic device include display components such as organic EL panel modules; display devices such as televisions, mobile phones, smartphones, and personal computers; and light-emitting devices for lighting and vehicle lighting. [Examples]

[0058] <Compound> The compound represented by formula (1) used in the manufacture of the organic EL element in the example is shown below. [ka]

[0059] The compounds used in the manufacture of the comparative organic EL element are shown below. [ka]

[0060] Example 1 An organic electroluminescent (EL) element was constructed by providing a hole transport band, an emissive layer, a first electron transport layer, a second electron transport layer, and a cathode on a glass substrate with an ITO transparent electrode (anode). Compound ET-1 was used in the second electron transport layer.

[0061] Examples 2-4 Organic EL elements were fabricated and evaluated using the same method as in Example 1, except that the compounds listed in Table 1 were used instead of compound ET-1.

[0062] Comparative Example 1 Organic EL elements were fabricated and evaluated using the same method as in Example 1, except that the compounds listed in Table 1 were used instead of compound ET-1.

[0063] [Table 1]

[0064] The organic EL elements of Examples 1 to 4 were found to have superior element performance compared to the organic EL element of Comparative Example 1.

[0065] <Synthesis of Compounds> (Synthesis Example 1) Synthesis of ET-1 ET-1 was synthesized using the following synthesis route. [ka] 2-(3′-bromo-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (8.8g), 4,4,5,5-tetramethyl-2-(tetraphen-7-yl)-1,3,2-dioxaborolane (7.1g), and Pd(PPh3)4 (0.55g) were placed in a flask. After replacing the atmosphere in the flask with argon gas, 1,4-dioxane (400mL) and potassium phosphate aqueous solution (2M, 24mL) were added, and the mixture was heated and stirred under reflux conditions for 16 hours. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain ET-1 as a white solid (6.4g, yield 55%). Mass spectral analysis revealed a molecular weight of 611.75 and a m / e ratio of 612, identifying it as the target substance.

[0066] (Synthesis Example 2) Synthesis of ET-2 ET-2 was synthesized using the following synthesis route. [ka] 2-(4-(4-bromonaphthalene-1-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (10.7g), 4,4,5,5-tetramethyl-2-(tetraphen-7-yl)-1,3,2-dioxaborolane (7.4g), Pd2(dba)3 (0.19g), and S-Phos (0.34g) were placed in a flask. The atmosphere in the flask was replaced with argon gas, and then 1,4-dioxane (100mL) and sodium carbonate aqueous solution (2M, 21mL) were added. The mixture was heated and stirred under reflux conditions for 7 hours. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain ET-2 as a white solid (11.9g, yield 86%). Mass spectral analysis revealed a molecular weight of 661.81 and a m / e ratio of 662, identifying it as the target substance.

[0067] (Synthesis Example 3) Synthesis of ET-3 ET-3 was synthesized using the following synthesis route. [ka] Except for using 12-bromo-7-phenyltetrafen instead of 2-(4-(4-bromonaphthalene-1-yl)phenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and using 2,4-diphenyl-6-(3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-1,3,5-triazine instead of 4,4,5,5-tetramethyl-2-(tetraphen-7-yl)-1,3,2-dioxaborolan, the same procedure as in Synthesis Example 2 was followed to obtain ET-3 as a white solid (13.1 g, yield 91%). Mass spectral analysis revealed a molecular weight of 687.85 and a m / e ratio of 688, identifying it as the target substance.

[0068] (Synthesis Example 4) Synthesis of ET-4 ET-4 was synthesized using the following synthesis route. [ka] Except for using 2-(3′-bromo-[1,1′-biphenyl]-3-yl)-4,6-bis(phenyl-d5)-1,3,5-triazine instead of 2-(4-(4-bromonaphthalene-1-yl)phenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, the same procedure as in Synthesis Example 2 was followed to obtain ET-4 as a white solid (3.4 g, yield 78%). Mass spectral analysis revealed a molecular weight of 621.81 and a m / e ratio of 622, identifying it as the target substance.

Claims

1. A compound represented by the following formula (1). [Chemistry 18] (In formula (1), L １ and L ２ Each of these is an independent group represented by one of the following formulas (a1) to (a13). 【Chemistry 19】 In formulas (a1) to (a13), One of the two *s is the benzanthracene skeleton or L in formula (1). １ This represents a single bond that connects to the triazine skeleton or L in formula (1). ２ This represents a single bond that connects to something. R ａ１ teeth, hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, These are substituted or unsubstituted cycloalkyl groups with 5 to 10 carbon atoms forming a ring. Multiple R ａ１ They may be the same or different from each other. R １１ and R １２ One of them represents a single bond that binds to L １ and is represented by a single bond. R that does not represent the single bond １１ and R １２ , and R １ ~R １０ Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms. R ２１ ~R ３０ Each of them operates independently. hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, (These are substituted or unsubstituted cycloalkyl groups with 5 to 10 carbon atoms forming a ring.)

2. The compound according to claim 1, represented by the following formula (1-1). 【Chemistry 20】 (In formula (1-1), L １ , L ２ , R １ ~R １１ , and R ２１ ~R ３０ This is as defined in formula (1) above.

3. The compound according to claim 1, represented by any of the following formulas (1-11) to (1-13). 【Chemistry 21】 (In formulas (1-11) to (1-13), R １ ~R １２ , R ２１ ~R ３０ , and R ａ１ This is as defined in formula (1) above.

4. Cathode and, Anode and, One or more organic layers disposed between the cathode and the anode, It has, At least one of the organic layers contains the compound described in any one of claims 1 to 3. Organic electroluminescent element.

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