Compound, organic electroluminescent element, and electronic device

Abstract

The compound represented by the following general formula has excellent hole transport capability and electron blocking capability. A, R1, and R2 represent a monovalent aromatic hydrocarbon group or the like, B and C represent a naphthylene group, and L1 to L3 represent a single bond or a divalent aromatic hydrocarbon group or the like. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound useful as an electron blocking material or a hole transporting material, and an organic electroluminescent device and an electronic device using the compound. Background Art

[0002] Organic electroluminescent elements (organic EL elements) are self-luminous elements and are therefore brighter and more visually pleasing than liquid crystal elements, and are capable of clear display. Therefore, active research is being conducted.

[0003] In 1987, CWTang of Eastman Kodak Company developed a layered structure element that assigned various functions to each material as a practical organic EL element. Specifically, they stacked a phosphor that can transport electrons and an organic substance that can transport holes, injected the two charges into the phosphor layer and made it emit light, thereby obtaining 1000cd / m at a voltage of less than 10V. 2 The above high brightness (for example, refer to Patent Document 1 and Patent Document 2).

[0004] So far, many improvements have been made for the practical application of organic EL elements, and the various functions of the stacked structure have been further subdivided. High efficiency and durability have been achieved by arranging a stacked structure of an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode in sequence on a substrate (for example, refer to non-patent document 1).

[0005] In addition, in order to further improve the luminous efficiency, attempts are being made to utilize triplet excitons, and the use of phosphorescent compounds is being studied (for example, see Non-Patent Document 2). In addition, a device that utilizes luminescence based on thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Andada et al. of Kyushu University achieved an external quantum efficiency of 5.3% by using a device using a thermally activated delayed fluorescence material (for example, see Non-Patent Document 3).

[0006] The light-emitting layer of these organic EL elements is usually made by doping a fluorescent compound or a phosphorescent compound or a material emitting delayed fluorescence in a charge transporting compound called a host material. In addition, as described in the above-mentioned non-patent documents, various organic layers are provided in the organic EL element, and the selection of the organic material has a great influence on the efficiency and durability of the element (for example, refer to non-patent document 2).

[0007] That is, in an organic EL element, the charges injected from the two electrodes are rebonded in the light-emitting layer to obtain light emission, so how to efficiently deliver the two charges of holes and electrons to the light-emitting layer is very important, and it is necessary to make an element with excellent carrier balance. For example, by using a material with hole injection properties that supply holes injected from the anode to the light-emitting layer or electron blocking properties that block electrons injected from the cathode, the probability of holes and electrons rebonding in the light-emitting layer is increased, and the excitons generated in the light-emitting layer are locked, thereby obtaining high luminous efficiency. Therefore, it is required that the mobility of holes in the hole transport material is large, the electron blocking property is high, and the durability to electrons is high.

[0008] In addition, regarding the life of the element, the heat resistance and amorphousness of the material are also important. In materials with low heat resistance, thermal decomposition occurs even at relatively low temperatures due to the heat generated when the element is driven, resulting in material degradation. In materials with low amorphousness, thin film crystallization occurs even in a relatively short period of time, resulting in element degradation. Therefore, the materials used are required to have high heat resistance and good amorphousness.

[0009] Until now, hole transport materials used in organic EL devices include N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) or various aromatic amine derivatives (for example, see Patent Documents 1 and 2). However, although NPD has good hole transport capability, its glass transition point (Tg), which is an indicator of heat resistance, is as low as 96°C, and crystallization under high temperature conditions may cause a decrease in device characteristics (for example, see Non-Patent Document 4).

[0010] Among the above aromatic amine derivatives, there is a compound having a hole mobility of 10 -3 cm 2 / Vs or more excellent mobility compounds (for example, reference patent document 1 and patent document 2), but due to insufficient electron blocking property, a part of the electrons will pass through the light-emitting layer, so that it is impossible to expect an increase in luminous efficiency. Therefore, in order to achieve further high efficiency, a material with higher electron blocking property, more stable film and higher heat resistance is required. In addition, although there are reports of aromatic amine derivatives with high durability (for example, reference patent document 3), they are used as charge transport materials for electronic photographic photoreceptors, and there is no example of use as organic EL elements.

[0011] In order to solve this problem, substituted carbazole structures or aromatic amine compounds have been proposed as compounds with improved properties such as heat resistance and hole injection properties (for example, refer to Patent Documents 4 and 5). However, in elements using these compounds in hole injection layers or hole transport layers, although improvements have been made in element life and luminous efficiency, these improvements are not sufficient, and further lowering of driving voltage or higher luminous efficiency and longer element life are required. Previous technical literature Patent Literature

[0012] Patent Document 1: U.S. Patent No. 5792557 Patent Document 2: U.S. Patent No. 5,639,914 Patent Document 3: U.S. Patent No. 7759030 Patent Document 4: Japanese Patent Application Publication No. 2009-076817 Patent Document 5: Patent No. 6674892 Patent Document 6: European Patent No. 2684932 Patent document 7: KR1020200131929A Patent Document 8: WO2017 / 073594A1 Non-patent literature

[0013] Non-patent document 1: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 55-61 (2001) Non-patent document 2: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 23-31 (2001) Non-patent document 3: Appl. Phys. Let., 98, 083302 (2011) Non-patent document 4: Preliminary documents of the third regular meeting of the Organic EL Symposium, pp. 13-14 (2006) Summary of the invention Technical issues to be solved by the invention

[0014] As described above, aromatic amine compounds having various functions have been proposed as materials for organic EL devices. However, in reality, a compound having excellent hole transporting ability and electron blocking ability and high thermal stability has not yet been realized. The present invention aims to provide a material for an organic EL element having excellent hole transporting ability and electron blocking ability and high thermal stability in a thin film state, and also to provide an organic EL element having low driving voltage, high luminous efficiency and power efficiency and long element life. Means for solving technical problems

[0015] The inventors of the present invention have conducted in-depth research to achieve the above-mentioned purpose, and as a result, found that an amine compound having at least two naphthylene groups bonded with an aromatic hydrocarbon group or an aromatic heterocyclic group has excellent hole transport ability and electron blocking ability, and high thermal stability in a thin film state. Then, it was found that by using the amine compound, an organic EL element with a low driving voltage, high luminous efficiency and power efficiency, and a long life was achieved. The present invention is proposed based on these insights, and specifically has the following structure.

[0016] 1) A compound represented by the following general formula (I).

[0017] [Chemical formula 1]

[0018] In the formula, A represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group, B and C represent the same or different deuterium-substituted or unsubstituted naphthylene, R1 and R2 may be the same or different from each other. a deuterium-substituted or unsubstituted monovalent aromatic hydrocarbon group, or a deuterium-substituted or unsubstituted monovalent aromatic heterocyclic group, L1, L2 and L3 may be the same or different from each other. single bond, A deuterium-substituted or unsubstituted divalent aromatic hydrocarbon group, or a deuterium-substituted or unsubstituted divalent aromatic heterocyclic group, A-L3 is not an unsubstituted aromatic heterocyclic group.

[0019] 2) Furthermore, the present invention is the compound described in 1) above, wherein B and C in the general formula (I) may be the same or different from each other. Deuterium-substituted or unsubstituted 1,2-naphthylene, Deuterium-substituted or unsubstituted 1,3-naphthylene, Deuterium-substituted or unsubstituted 1,4-naphthylene, Deuterium-substituted or unsubstituted 2,4-naphthylene, Deuterium-substituted or unsubstituted 2,5-naphthylene, Deuterium-substituted or unsubstituted 2,6-naphthylene, or It represents deuterium-substituted or unsubstituted 2,8-naphthylene.

[0020] 3) Furthermore, the present invention is a compound as described in 1) or 2) above, wherein L1 and L2 in the general formula (I) are Deuterium-substituted or unsubstituted phenylene, or Deuterium-substituted or unsubstituted biphenylene is represented.

[0021] 4) Furthermore, the present invention is a compound described in any one of 1) to 3) above, wherein R1 and R2 in the general formula (I) are the same or different, Deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, Deuterium-substituted or unsubstituted dibenzofuranyl, Deuterium-substituted or unsubstituted phenanthrenyl, or Deuterium-substituted or unsubstituted biphenyl is represented.

[0022] 5) Furthermore, the present invention is a compound described in any one of 1) to 4) above, wherein A in the general formula (I) is Substituted or unsubstituted phenyl, Substituted or unsubstituted naphthyl, Substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted dibenzothienyl, Substituted or unsubstituted phenoxy, or A substituted or unsubstituted biphenyl group is represented.

[0023] 6) Furthermore, the present invention is a compound described in any one of 1) to 5) above, wherein B and C in the general formula (I) are The same groups are represented.

[0024] 7) Furthermore, the present invention is the compound described in 6) above, wherein R1 and R2 in the general formula (I) are The same groups are represented.

[0025] 8) Furthermore, the present invention is the compound described in 6) above, wherein R1 and R2 in the general formula (I) are Different groups are indicated.

[0026] 9) Furthermore, the present invention is a compound described in any one of 1) to 5) above, wherein B and C in the general formula (I) are Different groups are indicated.

[0027] 10) Furthermore, the present invention is the compound described in 9) above, wherein R1 and R2 in the general formula (I) are The same groups are represented.

[0028] 11) Furthermore, the present invention is the compound described in 9) above, wherein R1 and R2 in the general formula (I) are Different groups are indicated.

[0029] 12) The compound according to any one of 1) to 11) above, wherein A thin film with a thickness of 100 nm was prepared by vacuum evaporation of the compound represented by the general formula (I) on a substrate with indium tin oxide (ITO). The absolute value of the HOMO energy level of the compound represented by the general formula (I) measured under vacuum using an ionization potential measuring device was greater than 5.60 eV and less than 5.80 eV.

[0030] 13) An electron blocking material comprising the compound described in any one of 1) to 12) above.

[0031] 14) An organic EL element comprising: a pair of electrodes; and an organic layer disposed between the pair of electrodes and including at least a light-emitting layer, wherein at least one layer of the organic layer contains the compound described in any one of 1) to 12).

[0032] 15) The organic EL device according to 14) above, wherein At least one of the organic layers is an electron blocking layer, and the electron blocking layer contains the compound.

[0033] 16) The organic EL device according to 15) above, wherein At least one of the organic layers is a hole transport layer, and the hole transport layer contains a compound represented by the following general formula (II). [Chemical formula 2] (In the formula, Ar1 to Ar5 may be the same as or different from each other and represent a substituted or unsubstituted monovalent aromatic hydrocarbon group. Ar6 to Ar8 may be the same as or different from each other and represent a hydrogen atom or a substituted or unsubstituted monovalent aromatic hydrocarbon group, and at least two of Ar6 to Ar8 are hydrogen atoms. n1 represents 0, 1 or 2. Ar3 and Ar4 may be bonded to each other via a single bond to form a ring, The groups may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring. Ar3 or Ar4 may be bonded to a benzene ring to which the -N(Ar3)(Ar4) group is bonded via a single bond to form a ring, or may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

[0034] 17) The organic EL element according to 16) above, wherein A thin film with a thickness of 100 nm was prepared by vacuum evaporation of the compound represented by the general formula (II) on a substrate with ITO, and the absolute value of the HOMO energy level of the compound represented by the general formula (II) measured under vacuum using an ionization potential measuring device was greater than or equal to 5.50 eV and less than or equal to 5.65 eV.

[0035] 18) The organic EL device according to 16) or 17) above, wherein The absolute value of the difference in HOMO energy level between the compound represented by the general formula (I) and the compound represented by the general formula (II) is 0.05 eV or more and 0.35 eV or less.

[0036] 19) An electronic device comprising: a pair of electrodes; and at least one organic layer disposed between the pair of electrodes, wherein at least one of the organic layers contains the compound described in any one of 1) to 12). Effects of the Invention

[0037] The compound of the present invention has excellent hole transport ability and electron blocking ability, and has high thermal stability in a thin film state, so it is useful as an electron blocking material or a hole transport material. An organic EL element using the compound of the present invention as a material for an organic layer can achieve low driving voltage, high luminous efficiency, and long element life. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 It is a schematic cross-sectional view showing the layer structure of the organic EL elements produced in Examples 23 to 120 and Comparative Examples 1 to 5. DETAILED DESCRIPTION

[0039] Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below is sometimes carried out according to representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this specification, the numerical range represented by "to" refers to a range including the numerical values ​​recorded before and after "to" as the lower limit and the upper limit. Furthermore, there is no particular limitation on the isotope types of hydrogen atoms present in the molecules of the compounds used in the present invention. For example, the hydrogen atoms in the molecules may all be 1 H, or part or all of it 2H (deuterium D). In this specification, the description "substituted or unsubstituted" means that the group marked with the term may be an unsubstituted group (a group in which hydrogen atoms are not replaced by substituents), and at least one hydrogen atom of the group may be substituted by a substituent. The description "deuterium substituted or unsubstituted" means that the group marked with the term may be an unsubstituted group (a group in which hydrogen atoms are not replaced by substituents), and at least one hydrogen atom of the group may be a deuterium atom ( 2 H). However, as described above, the hydrogen atoms present in the molecules of the compounds used in the present invention may be 1 H can also be 2 H (deuterium D). Therefore, in the "deuterium substituted" of "deuterium substituted or unsubstituted", the description of "unsubstituted" emphasizes that the hydrogen atom is not excluded as a "deuterium atom". In addition, unless otherwise specified, the "number of carbon atoms" refers to the number of carbon atoms including the number of substituents. In this specification, an "organic layer" refers to a layer containing 70% by weight or more of an organic compound, and an "organic compound" refers to a compound containing one or more carbon atoms. Among the organic compounds, for example, a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms can be used. 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.

[0040] <Compounds represented by general formula (I)> The compound of the present invention is a compound represented by the above-mentioned general formula (I). The aromatic ring constituting the "monovalent aromatic hydrocarbon group" of the "substituted or unsubstituted monovalent aromatic hydrocarbon group" represented by A in the general formula (I), and the aromatic ring constituting the "monovalent aromatic hydrocarbon group" of the "deuterium-substituted or unsubstituted monovalent aromatic hydrocarbon group" represented by R1 and R2 may be a monocyclic ring, a condensed ring formed by condensing two or more rings, a linked ring formed by linking two or more rings via a single bond, or a spiro ring formed by linking two or more rings via a spiro ring. In the case of a condensed ring, the number of condensed 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, more preferably 2 to 4, for example, 2, for example, 3. The number of carbon atoms constituting the ring skeleton of the aromatic hydrocarbon group 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. Specific examples of the "monovalent aromatic hydrocarbon group" in A, R1 and R2 include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylene, fluorenyl and spirobifluorenyl.

[0041] The aromatic heterocycle constituting the "monovalent aromatic heterocycle" of the "substituted or unsubstituted monovalent aromatic heterocycle" represented by A, and the aromatic heterocycle constituting the "monovalent aromatic heterocycle" of the "deuterium-substituted or unsubstituted monovalent aromatic heterocycle" represented by R1 and R2 may be a monocyclic ring or a condensed ring formed by condensing two or more rings. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, for example, 2 to 4. Furthermore, in the case of a condensed ring, only two or more aromatic heterocycles may be condensed, or one or more aromatic heterocycles and one or more aromatic hydrocarbon rings may be condensed. Examples of heteroatoms constituting the aromatic heterocycle include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of atoms constituting the ring skeleton of the aromatic heterocycle is, for example, 4 to 40, for example, 5 to 30, for example, 5 to 20. Specific examples of the "monovalent aromatic heterocyclic group" in A, R1 and R2 include pyridyl, pyrimidinyl, triazine, furanyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, azafluorenyl, diazafluorenyl, azaspirobifluorenyl, diazaspirobifluorenyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl and carbolyl.

[0042] Regarding the “substituted or unsubstituted condensed polycyclic aromatic group”, reference can be made to the description and specific examples of the case of a condensed ring formed by condensing two or more rings in the description of the above-mentioned “substituted or unsubstituted aromatic hydrocarbon group” and “substituted or unsubstituted aromatic heterocyclic group”.

[0043] The "substituted or unsubstituted monovalent aromatic hydrocarbon group" and "substituted or unsubstituted monovalent aromatic heterocyclic group" represented by A in the general formula (I) are "substituents" when they are substituted aromatic hydrocarbon groups and substituted aromatic heterocyclic groups, respectively. Specifically, there can be mentioned deuterium atoms, cyano groups, nitro groups; halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, iodine atoms; silyl groups such as trimethylsilyl groups and triphenylsilyl groups; linear or branched alkyl groups having 1 to 6 carbon atoms such as methyl groups, ethyl groups and propyl groups; linear or branched alkoxy groups having 1 to 6 carbon atoms such as methoxy groups, ethoxy groups and propoxy groups; alkenyl groups such as vinyl groups and allyl groups; aryloxy groups such as phenoxy groups and tolyloxy groups ; aryl alkoxy groups such as benzyloxy and phenethoxy; monovalent aromatic hydrocarbon groups whose ring skeletons have 6 to 20 atoms such as phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl and triphenylene; monovalent aromatic heterocyclic groups whose ring skeletons have 5 to 20 atoms such as pyridyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbolyl; the hydrogen atoms of these substituents may be substituted by the substituents exemplified herein. Among the preferred substituents, there are deuterium atoms, linear or branched alkyl groups with 1 to 6 carbon atoms, and univalent aromatic hydrocarbon groups with 6 to 20 atoms in the ring skeleton. In addition, regarding the substituents substituted by the substituents, the substituents directly substituted on the parent skeleton (aromatic hydrocarbon group, aromatic heterocyclic group) are sometimes referred to as "the first substituent", and the substituents substituted on the first substituent are referred to as "the second substituent". Here, when the first substituent includes a benzene ring, the benzene ring can be bonded to the parent skeleton to form a cyclic structure. And, when the benzene ring of the first substituent is substituted with more than two substituents, adjacent substituents can be bonded to each other to form a cyclic structure. Here, the bonding between the benzene ring and the parent skeleton in the first substituent and the bonding between the second substituents can be a single bond or a bonding via a connecting group. As examples of connecting groups, substituted or unsubstituted methylene, oxygen atoms or sulfur atoms can be cited.

[0044] In the general formula (I), for the description of the aromatic ring constituting the "divalent aromatic hydrocarbon group" of the "deuterium-substituted or unsubstituted divalent aromatic hydrocarbon group" and the aromatic heterocycle constituting the "divalent aromatic heterocyclic group" of the "deuterium-substituted or unsubstituted divalent aromatic heterocyclic group", reference can be made to the description of the aromatic ring constituting the "monovalent aromatic hydrocarbon group" and the aromatic heterocycle constituting the "monovalent aromatic heterocyclic group" in A, R1 and R2. Specific examples of the "divalent aromatic hydrocarbon group" include divalent groups obtained by removing one hydrogen atom from the specific examples of the "monovalent aromatic hydrocarbon group" described above, and specific examples of the "divalent aromatic heterocyclic group" include divalent groups obtained by removing one hydrogen atom from the specific examples of the "monovalent aromatic heterocyclic group" described above.

[0045] There is no particular limitation on the position of the bond of the "naphthylene" in the "deuterium-substituted or unsubstituted naphthylene" represented by B and C. Examples of the naphthylene include 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 2,4-naphthylene, 2,5-naphthylene, 2,6-naphthylene, and 2,8-naphthylene.

[0046] As L1 and L2 in the general formula (I), a deuterium-substituted or unsubstituted divalent aromatic hydrocarbon group is preferred, a deuterium-substituted or unsubstituted biphenylene group or a deuterium-substituted or unsubstituted phenylene group is more preferred, a phenylene group is further preferred, and a 1,4-phenylene group is further preferred. As L3 in the general formula (I), a single bond or a substituted or unsubstituted phenylene group is more preferred, for example, a single bond, for example, a phenylene group (preferably a 1,3-phenylene group, a 1,4-phenylene group, and more preferably a 1,4-phenylene group) is more preferred. When A-L3 is a group having a structure in which two or more aromatic rings are linked, L3 is a substituted or unsubstituted phenylene group.

[0047] A in the general formula (I) is preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted biphenyl group, and further preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted 9-phenanthryl group.

[0048] As B and C in the general formula (I), 1,2-naphthylene, 1,3-naphthylene, 2,4-naphthylene or 2,8-naphthylene is more preferable.

[0049] As R1 and R2 in the general formula (I), deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted dibenzofuranyl, deuterium-substituted or unsubstituted phenanthryl or deuterium-substituted or unsubstituted biphenyl, more preferably phenyl or naphthyl.

[0050] As a preferred compound group represented by the general formula (I), it can be shown that R1-B-L1 and R2-C-L2 are different groups. Compound Group 1 includes Compound Group 1a in which L3 is a single bond and A is a substituted or unsubstituted aromatic hydrocarbon group, Compound Group 1b in which L3 is a deuterium-substituted or unsubstituted aromatic hydrocarbon group (e.g., a deuterium-substituted or unsubstituted phenylene group) and A is a substituted or unsubstituted aromatic hydrocarbon group, and Compound Group 1c in which L3 is a deuterium-substituted or unsubstituted aromatic hydrocarbon group (e.g., a deuterium-substituted or unsubstituted phenylene group) and A is a substituted or unsubstituted aromatic heterocyclic group. Compound Groups 1a to 1c may each have R1 and R2 that are the same, L1 and L2 that are the same, and B and C that are different. Compound Groups 1a to 1c may each have B and C that are the same, L1 and L2 that are the same, and R1 and R2 that are different. Compound groups 1a to 1c may have L1 and L2 that are the same, R1 and R2 that are different, and B and C that are different. A in compound groups 1a and 1b may be a phenyl group that may be substituted with one or more groups selected from the group consisting of phenyl, naphthyl, and phenanthryl. A in compound group 1c may be a dibenzofuranyl group or a dibenzothienyl group. Compound groups 1a to 1c may each further satisfy at least one of the following additional conditions. One of the additional conditions is that L1 and L2 are deuterium-substituted or unsubstituted divalent aromatic hydrocarbon groups, for example, phenylene. One of the additional conditions is that B and C are deuterium-substituted or unsubstituted 1,2-naphthylene, deuterium-substituted or unsubstituted 1,3-naphthylene, or deuterium-substituted or unsubstituted 1,4-naphthylene. One of the additional conditions is that B and C are deuterium-substituted or unsubstituted 2,4-naphthylene, deuterium-substituted or unsubstituted 2,5-naphthylene, deuterium-substituted or unsubstituted 2,6-naphthylene, or deuterium-substituted or unsubstituted 2,8-naphthylene. One of the additional conditions is that R1 and R2 are deuterium-substituted or unsubstituted monovalent aromatic hydrocarbon groups, for example, phenyl which may be substituted with one or more groups selected from the group consisting of phenyl, naphthyl, and phenanthryl. One of the additional conditions is that R1 and R2 are deuterium-substituted or unsubstituted monovalent aromatic heterocyclic groups, for example, dibenzofuranyl or dibenzothiophenyl.

[0051] As a preferred compound group represented by the general formula (I), it can be shown that R1-B-L1 and R2-C-L2 are the same group. Compound Group 2 includes Compound Group 2a in which L3 is a single bond and A is a substituted or unsubstituted aromatic hydrocarbon group, Compound Group 2b in which L3 is a deuterium-substituted or unsubstituted aromatic hydrocarbon group (e.g., a deuterium-substituted or unsubstituted phenylene group) and A is a substituted or unsubstituted aromatic hydrocarbon group, and Compound Group 2c in which L3 is a deuterium-substituted or unsubstituted aromatic hydrocarbon group (e.g., a deuterium-substituted or unsubstituted phenylene group) and A is a substituted or unsubstituted aromatic heterocyclic group. A of Compound Groups 2a and 2b may be a phenyl group which may be substituted with one or more groups selected from the group consisting of phenyl, naphthyl and phenanthryl. A of Compound Group 2c may be a dibenzofuranyl group or a dibenzothiophenyl group. Compound Groups 2a to 2c may each further satisfy at least one of the additional conditions described in Compound Group 1.

[0052] The molecular weight of the compound represented by general formula (I) is preferably 2000 or less, more preferably 1500 or less, for example, 1000 or less. The lower limit of the molecular weight of the compound represented by general formula (I) is the molecular weight of the smallest molecule that general formula (I) can adopt.

[0053] Specific examples of compounds represented by general formula (I) are shown below. The compounds represented by general formula (I) that can be used in the present invention should not be construed in a limiting sense by these specific examples. In addition, in the following chemical structural formula, hydrogen atoms ( 1 H) display, deuterium atoms ( 2 H) is displayed as "D".

[0054] [Chemical formula 3]

[0055] [Usefulness of the compound represented by general formula (I)] The compound represented by the general formula (I) of the present invention has excellent hole transport ability and electron blocking ability, and has high thermal stability in a thin film state, so it is useful as a material for the organic layer of an organic EL element. The compound represented by the general formula (I) can be used as a constituent material of an electron blocking layer or hole transport layer or a light-emitting layer of an organic EL element, for example, and is particularly useful as a constituent material of an electron blocking layer and a hole transport layer. An organic EL element in which the compound represented by the general formula (I) is included in an organic layer (e.g., at least one of an electron blocking layer, a hole transport layer, and a light-emitting layer) can achieve low driving voltage, high luminous efficiency, and long element life.

[0056] [Synthesis method of the compound represented by general formula (I) and evaluation method of properties] The compound represented by the general formula (I) is a novel compound. The compound represented by the general formula (I) can be synthesized by applying a known coupling reaction and appropriately selecting known reaction conditions. For details of the reaction, reference can be made to the synthesis examples described below. The compound represented by general formula (I) can be purified by known methods such as purification by column chromatography, adsorption purification by silica gel, activated carbon, activated clay, etc., recrystallization or crystallization from a solvent, and sublimation purification. The compound can be identified by NMR analysis.

[0057] As physical property values ​​that are indicators of the usefulness of the compound represented by general formula (I), melting point, glass transition point (Tg), and HOMO energy level can be cited. The melting point is an indicator of vapor deposition properties, the glass transition point (Tg) is an indicator of the stability of the thin film state, and the HOMO energy level is an indicator of hole injection or hole transport properties, or electron blocking properties.

[0058] The melting point and the glass transition point (Tg) can be measured, for example, using a powder of the compound to be measured with a high-sensitivity differential scanning calorimeter (DSC3100SA manufactured by Bruker AXS).

[0059] The energy level of HOMO can be determined by, for example, forming a thin film of the compound to be measured with a thickness of 100 nm on an ITO-coated substrate and using an ionization potential measuring apparatus (PYS-202 manufactured by Sumitomo Heavy Industries, Ltd.).

[0060] <Organic electroluminescent element> The organic electroluminescent element (organic EL element) of the present invention comprises: a pair of electrodes; and an organic layer disposed between the pair of electrodes and including at least a light-emitting layer, wherein at least one layer of the organic layer contains a compound represented by the general formula (I). Here, the pair of electrodes is an anode and a cathode. For the description of the compound represented by the general formula (I), reference can be made to the description in the above-mentioned column <Compound represented by the general formula (I)>. The compound represented by the general formula (I) has excellent hole transport ability and electron blocking ability, and has high thermal stability in a thin film state. Therefore, by using it as a material for the organic layer, it is possible to display a low driving voltage and a high luminous efficiency, thereby realizing an organic EL element with a long element life. The organic layer possessed by the organic EL element of the present invention includes at least a light-emitting layer, which may be composed of only a light-emitting layer, or may have more than one organic layer in addition to the light-emitting layer. Here, the compound represented by the general formula (I) may be contained in the light-emitting layer, or in the organic layer other than the light-emitting layer, but is preferably contained in the organic layer disposed between the light-emitting layer and the anode. As a specific example of the organic layer disposed between the light-emitting layer and the anode, a hole injection layer, a hole transport layer, an electron blocking layer, etc. may be cited, and the compound represented by the general formula (I) is preferably contained in the hole transport layer or the electron blocking layer, and is more preferably contained in the electron blocking layer. On the other hand, as a specific example of the organic layer disposed between the light-emitting layer and the cathode, a hole blocking layer, an electron transport layer, an electron injection layer, etc. may be cited. The materials of these organic layers can be appropriately selected and used from known materials.

[0061] In one embodiment of the present invention, the organic EL element has a laminated structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode are sequentially laminated on a substrate, and at least a compound represented by the general formula (I) is contained in the electron blocking layer. Here, a hole blocking layer may be provided between the light-emitting layer and the electron transport layer. In addition, the organic EL element may have two or more functions in one organic layer. As such an organic layer, a hole injection transport layer having both a hole injection layer and a hole transport layer, or an electron injection transport layer having both an electron injection layer and an electron transport layer may be cited. In addition, the organic EL element may also be provided as a structure in which more than two layers of organic layers having the same function are laminated. For example, a structure in which two layers of hole transport layers are laminated, or a structure in which two layers of light-emitting layers are laminated, or a structure in which two layers of electron transport layers are laminated, etc. may be cited. Hereinafter, each member and each layer of the organic EL element will be described in detail.

[0062] [anode] The anode in the organic EL element of the present invention can be made of an electrode material having a large work function, such as ITO or gold.

[0063] [Hole injection layer, hole transport layer] The hole injection layer is provided between the anode and the light-emitting layer or between the anode and the hole transport layer, etc., and is provided to reduce the injection barrier of holes supplied from the anode, thereby reducing the driving voltage and improving the light emission brightness. The hole transport layer is a layer having a function of transporting holes. The hole transport layer may also be a hole injection transport layer having the function of a hole injection layer. The material of the hole transport layer or the hole injection transport layer can use a compound represented by the general formula (I) or the general formula (II). By using the compound represented by the general formula (I) or the general formula (II) as the material of the hole transport layer, it is possible to display a low driving voltage and a high luminous efficiency, thereby realizing an organic EL element with a long element life. The compound represented by the general formula (I) or the general formula (II) used for the hole transport layer and the hole injection transport layer can be one of the compound groups represented by the general formula (I) or the general formula (II), or it can be two or more. In addition, the compound represented by the general formula (I) or the general formula (II) and other hole transport materials or hole injection materials can also be used in combination. For the details and preferred range of the compound represented by the general formula (II), reference can be made to

[0052] to

[0059] of Patent Document 8. Furthermore, as specific examples of the compound represented by the general formula (II), compounds (1-1) to (1-43) described in

[0108] to

[0150] of Patent Document 8 cited as part of this specification can be cited. In the organic EL element of the present invention, as a layer adjacent to the layer containing the compound represented by the general formula (II), it is preferred to form a layer containing the compound represented by the general formula (I), and as a layer adjacent to the hole transport layer containing the compound represented by the general formula (II), it is more preferred to form an electron blocking layer containing the compound represented by the general formula (I). Furthermore, in the present invention, the hole transport layer can use a compound represented by the general formula (II), and the hole injection layer adjacent to it can also preferably use a compound represented by the general formula (II). At this time, the compound of the general formula (II) used for the hole injection layer can be a compound different from the compound of the general formula (II) used for the hole transport layer, or it can be the same compound. When the same compound is used, it is preferred to use the compound of the general formula (II) and other hole injection materials as a mixture in the hole injection layer.

[0064] As materials for the hole injection layer, porphyrin compounds represented by copper phthalocyanine, starburst-type triphenylamine derivatives, aromatic amine compounds having two or more triphenylamine structures or carbazole structures in the molecule and each having a structure formed by connecting a single bond or a divalent group not containing a heteroatom, acceptor heterocyclic compounds such as hexacyanotriphenylene, and coating-type polymer materials can be used.

[0065] As materials for the hole injection layer or hole transport layer, or hole injection transport layer, in addition to the compound represented by general formula (I), N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (TPD) or N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (NPD), benzidine derivatives such as N,N,N',N'-tetraphenylbenzidine, 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC), and arylamine compounds having two or more triphenylamine structures or carbazole structures in the molecule and each having a structure formed by connecting by a single bond or a divalent group not containing a hetero atom, etc. can also be used. In addition, coating-type polymer materials such as poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonic acid) (PSS), and polymer compounds having the structure of benzidine derivatives such as TPD in their partial structures, etc. can also be used.

[0066] These materials can be formed as a single film composed of one type, or as a mixed film composed of multiple types. Furthermore, the hole transport layer can be a single-layer structure of a single film or a mixed film, or a stacked structure of multiple single films, a stacked structure of multiple mixed films, or a stacked structure of more than one single film and more than one mixed film. Furthermore, a hole injection layer or a hole transport layer may be formed by adding a P-type dopant such as tribromoaniline hexachloroantimony or a radialene derivative described in European Patent No. 2684932 to these hole injection materials or hole transport materials.

[0067] The absolute value of the energy level of HOMO possessed by the hole transport material is preferably a value greater than the absolute value (5.4eV) of the HOMO level possessed by general hole transport materials such as NPD and TPD (i.e., having a deeper HOMO level), and is preferably a value smaller than the absolute value of the energy level of HOMO possessed by the electron blocking material described later. By having a deeper HOMO level, there is a better hole transport ability. On the other hand, if the absolute value of the energy level of the HOMO of the hole transport material is smaller than the absolute value of the HOMO level possessed by the electron blocking material, the transmission of holes to the light-emitting layer is hindered. Specifically, the absolute value of the energy level of the HOMO of the hole transport material is preferably 5.45eV or more and 5.80eV or less, more preferably 5.50eV or more and 5.65eV or less.

[0068] [Electron blocking layer] The electron blocking layer is, for example, a layer disposed between the light-emitting layer and the hole transport layer, and has the function of inhibiting the diffusion of electrons present in the light-emitting layer to the outside (hole transport layer side) of the light-emitting layer. Thus, the probability of rebonding of electrons and holes in the light-emitting layer can be increased. The electron blocking layer generally also has the function of transporting holes. Furthermore, the electron blocking layer may also have the function of an exciton blocking layer that inhibits the diffusion of excitons from the light-emitting layer. The compound represented by the general formula (I) can be used in the material of the electron blocking layer. The compound represented by the general formula (I) has excellent electron blocking ability, high electron tolerance and is also stable in a thin film state, and also has the characteristic of locking the excitons generated in the light-emitting layer. Thus, the organic EL element using the compound represented by the general formula (I) as an electron blocking material has an increased probability of rebonding of holes and electrons, and thermal deactivation is suppressed, so that it has high luminous efficiency, and the current tolerance is improved by reducing the driving voltage, thereby improving the maximum luminous brightness. The compound represented by the general formula (I) used for the electron blocking layer can be one of the compound groups represented by the general formula (I), or it can be more than two. In addition, the compound represented by the general formula (I) and other electron blocking materials can also be used in combination.

[0069] As materials for the electron blocking layer, in addition to the compounds represented by the general formula (I), compounds having an electron blocking effect such as 4,4',4"-tri(N-carbazyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz), and compounds having a triphenylsilyl and triarylamine structure represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene can also be used. These electron blocking materials can be formed as a single film composed of one type, or as a mixed film composed of multiple types. Furthermore, the electron blocking layer can be a single-layer structure of a single film or a mixed film, or a stacked structure of multiple single films, a stacked structure of multiple mixed films, or a stacked structure of more than one single film and more than one mixed film.

[0070] The absolute value of the energy level of the HOMO of the electron blocking material is preferably a value greater than the absolute value of the energy level of the HOMO of the hole transport material (i.e., having a deeper HOMO level). Specifically, the absolute value of the energy level of the HOMO of the electron blocking material is preferably 5.55 eV or more and 5.90 eV or less, more preferably 5.60 eV or more and 5.80 eV or less. Furthermore, the absolute value of the energy level of the HOMO of the electron blocking material is preferably greater than 0.05 eV and less than 0.45 eV of the absolute value of the energy level of the HOMO of the hole transport material, more preferably greater than 0.05 eV and less than 0.35 eV, and further preferably greater than 0.10 eV and less than 0.35 eV.

[0071] [Luminous layer] The light-emitting layer is a layer that emits light by re-bonding holes and electrons injected from the anode and cathode, respectively, to generate excitons. A light-emitting material alone may be used for the light-emitting layer, but preferably the light-emitting layer contains a light-emitting material and a host material. The compound represented by the general formula (I) can be used in the host material. The compound represented by the general formula (I) has excellent hole transport properties and a wide energy band gap. Thus, the organic EL element using the compound represented by the general formula (I) as the host material of the light-emitting layer has a reduced driving voltage and improved luminous efficiency. The compound represented by the general formula (I) used for the host material can be one of the compound group represented by the general formula (I), or two or more. Furthermore, the compound represented by the general formula (I) and other host materials can also be used in combination.

[0072] As the main material, it is also possible to use anthracene derivatives, heterocyclic compounds having an indole ring as a partial structure of the condensed ring, heterocyclic compounds having a carbazole ring as a partial structure of the condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives and polydialkylfluorene derivatives, etc. In addition, as the main material with hole injection / transport properties, carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP can be cited, and as the main material with electron transport properties, p-bis(triphenylsilyl)benzene (UGH2) or 2,2',2"-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI) can be cited.

[0073] The light-emitting material may be any one of a fluorescent light-emitting material, a phosphorescent light-emitting material, and a delayed fluorescent material. As luminescent materials, metal complexes of quinolinol derivatives headed by tri(8-hydroxyquinoline)aluminum (Alq3), various metal complexes, anthracene derivatives, distyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, poly(p-phenylene vinylene) derivatives, etc., in addition, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives and aminostyryl derivatives, etc. can also be mentioned.

[0074] As the phosphorescent material, a metal complex with iridium or platinum as the central metal can be used. For example, green phosphorescent materials such as Ir(ppy)3, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp2Ir(acac) can be cited. In order to avoid concentration quenching, the doping amount in the host material of the phosphorescent material is preferably set in the range of 1 to 30 weight % relative to the total amount of the light-emitting layer.

[0075] Examples of the delayed fluorescent material include carbazolyl dicyanobenzene (CDCB) derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN. For specific examples of the delayed fluorescent material, refer to Appl. Phys. Let., 98, 083302 (2011). [Chemical formula 4]

[0076] In the light-emitting layer, a compound represented by the following general formula (III-1) or (III-2) can be preferably used as a light-emitting material. [Chemical formula 5]

[0077] In the formula, Q1 to Q3 may be the same as or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms. Y1 to Y3 may be the same as or different from each other, and represent N-R3, CR4R5, O, S, Se, or SiR6R7. R3 to R7 may be the same as or different from each other, and represent a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monovalent hydrocarbon group having 6 to 50 carbon atoms. An aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms. R3 to R7 may be bonded to any one of Q1 to Q3 via a single bond, N, O, P or S, or may be condensed to form a ring, and R4 and R5, R6 and R7 may be bonded to each other to form a ring. When Y2 or Y3 is N-R3, at least one of R3 represents a group represented by the following general formula (IV-A) or a group represented by the following general formula (IV-B). [Chemical formula 6]

[0078] In the general formula (IV-A), X represents O or S. R8 to R 15The alkyl radicals may be the same as or different from each other and represent a single bond, a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted R8~R 15 Any one of R8 to R 15 The group may be bonded to adjacent groups via a single bond, N, O or S, or may be condensed to form a ring.

[0079] In the general formula (IV-B), R 16 R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms. 17 R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms. 18 ~R 20They may be the same as or different from each other and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 30 carbon atoms. The wavy line portion represents a bonding portion to N. R 16 ~R 20 The group may be bonded to adjacent groups via a single bond, N, O or S, or may be condensed to form a ring.

[0080] Q1 to Q3 of the general formula (III-1) and (III-2) are preferably benzene rings. The benzene rings of Q1 and Q2 preferably adopt a benzofuran condensed ring structure or a benzothiophene condensed ring structure. As substituents for the benzene rings of Q1 to Q3, deuterium atoms, alkyl groups having 1 to 30 carbon atoms, aromatic hydrocarbon groups having 6 to 50 carbon atoms, diarylamino groups having 12 to 30 carbon atoms, and groups formed by combining two or more of these are preferred. Q2 of the general formula (III-1) and (III-2) is also preferably a furan ring (i.e., a benzofuran structure) formed by the condensation of a benzene ring or a thiol ring (i.e., a benzothiophene structure) formed by the condensation of a benzene ring. Y1 of the general formula (III-1) and (III-2) is preferably O or S. Y2 and Y3 are preferably N-R3, respectively and independently. R3 is preferably a substituted or unsubstituted phenyl group (a ring may be condensed in the phenyl group). As a substituent, a deuterium atom, an alkyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, a dibenzofuranyl group, a dibenzothiophene group, and a group composed of two or more of these are preferred. The benzene ring constituting the phenyl group may adopt a benzofuran condensed ring structure or a benzothiophene condensed ring structure. Y3 is also preferably O.

[0081] Preferred compounds include compounds represented by the following general formula (III-1) and (III-2), compounds represented by the following general formula (III-3), compounds represented by the following general formula (III-4), compounds represented by the following general formula (III-5), and compounds represented by the following general formula (III-6). [Chemical formula 7]

[0082] In general formulae (III-3) to (III-6), Y1 to Y3, R3 to R7 have the same meanings as in general formulae (III-1) and (III-2). Y4 represents N-R3, C-R4R5, O, S, Se or Si-R6R7. Z may be the same or different and may represent N or CR 21 . R 21 R represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms. 21 , respectively, can be bonded to adjacent groups via a single bond, N, O or S, or can be condensed to form a ring. In addition, the definitions and details of terms such as groups in the description of general formulae (III-1) to (III-5) are the same as the definitions and details of terms such as groups described in general formula (I).

[0083] The compound represented by the general formula (I) can exhibit more excellent effects by being used in combination with the compound represented by the general formula (III-1) or (III-2). Therefore, it is possible to provide: an electron-blocking material composed of a compound represented by the general formula (I) for use in combination with a compound represented by the general formula (III-1) or (III-2); a stack (preferably a light-emitting stack) comprising a layer of a compound represented by the general formula (III-1) or (III-2) and a layer comprising a compound represented by the general formula (I); an organic EL element comprising a compound represented by the general formula (III-1) or (III-2) and a compound represented by the general formula (I); an organic EL element having a layer comprising a compound represented by the general formula (I) and a layer comprising a compound represented by the general formula (III-1) or (III-2) (the two layers are preferably adjacent); and an organic EL element having an electron-blocking layer comprising a compound represented by the general formula (I) and a light-emitting layer comprising a compound represented by the general formula (III-1) or (III-2) (the two layers are preferably adjacent).

[0084] In addition, by using it in combination with a compound represented by the general formula (II), an excellent effect can be exerted. Therefore, it is possible to provide: an electron blocking material composed of a compound represented by the general formula (I) for use in combination with a compound represented by the general formula (II) and a compound represented by the general formula (III-1) or (III-2); a laminate (preferably a light-emitting laminate) comprising a layer of a compound represented by the general formula (II), a layer of a compound represented by the general formula (III-1) or (III-2), and a layer of a compound represented by the general formula (I); a layer comprising a compound represented by the general formula (II), a compound represented by the general formula (III-1) or (III-2), a compound represented by the general formula (I); An organic EL element comprising a compound represented by the general formula (II); an organic EL element comprising a layer comprising a compound represented by the general formula (I), and a layer comprising a compound represented by the general formula (III-1) or (III-2) (these three layers are preferably stacked in sequential contact); and an organic EL element comprising a hole transport layer comprising a compound represented by the general formula (II), an electron blocking layer comprising a compound represented by the general formula (I), and a light-emitting layer comprising a compound represented by the general formula (III-1) or (III-2) (these three layers are preferably stacked in sequential contact).

[0085] Specific examples of the compound represented by (III-1) or (III-2) are shown below. However, the compound represented by the general formula (III-1) or (III-2) that can be used in the present invention should not be construed as being limited to these specific examples. [Chemical formula 8]

[0086] [Hole blocking layer] The hole blocking layer is, for example, a layer disposed between the light-emitting layer and the electron transport layer, and has the function of inhibiting the diffusion of holes present in the light-emitting layer to the outside (electron transport layer side) of the light-emitting layer, thereby increasing the probability of re-bonding of electrons and holes in the light-emitting layer. The hole blocking layer generally also has the function of transporting electrons. Furthermore, the hole blocking layer may also have the function of an exciton blocking layer that inhibits the diffusion of excitons from the light-emitting layer. As the material of the hole blocking layer, a compound having a hole blocking effect can be used, such as a phenanthroline derivative such as bathocuproine (BCP), a metal complex of a quinolol derivative such as bis(2-methyl-8-quinolinate)-4-(phenylphenol)aluminum (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives and triazine derivatives. These materials can also function as an electron transport material. These materials can be formed as a single film composed of one type, or as a mixed film composed of multiple types. Furthermore, the hole blocking layer can be a single-layer structure of a single film or a mixed film, or a stacked structure of a plurality of single films, a stacked structure of a plurality of mixed films, or a stacked structure of more than one single film and more than one mixed film.

[0087] [Electron transport layer, electron injection layer] The electron injection layer is provided between the cathode and the light-emitting layer, or between the cathode and the electron transport layer, etc., and is provided to reduce the injection barrier of electrons supplied from the cathode, thereby reducing the driving voltage and improving the light emission brightness. The electron transport layer is a layer having a function of transporting electrons. The electron transport layer may also be an electron injection transport layer having a function of an electron injection layer.

[0088] As the material of the electron injection layer, it is possible to use alkali metal salts such as lithium fluoride, cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinol derivatives such as lithium quinol, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr) and cesium (Cs). By the preferred selection of the electron transport layer and the cathode, the electron injection layer can be omitted.

[0089] As materials for the electron transport layer, metal complexes of quinolinol derivatives headed by Alq3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives and silole derivatives can be used. These materials can be formed as a single film composed of one type, or as a mixed film composed of multiple types. Furthermore, the electron transport layer can be a single-layer structure of a single film or a mixed film, or a stacked structure of multiple single films, a stacked structure of multiple mixed films, or a stacked structure of more than one single film and more than one mixed film. Furthermore, an electron injection layer or a hole transport layer may be formed by adding a metal (N-type dopant) such as cesium to these electron injection materials or electron transport materials.

[0090] [cathode] As the cathode, a material using a metal having a low work function such as aluminum, or an alloy having an even lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy as an electrode material can be used.

[0091] Each layer constituting the above-described organic EL element can be formed by a known method such as a vapor deposition method, a spin coating method, and an inkjet method.

[0092] <Electronic equipment> The electronic device of the present invention comprises: a pair of electrodes; and at least one organic layer disposed between the pair of electrodes, wherein at least one of the organic layers comprises a compound represented by general formula (I). For the description of the compound represented by general formula (I), reference can be made to the description in the above-mentioned <Compound represented by general formula (I)> column. As electronic devices, display devices or light-emitting devices having organic EL elements can be cited, and in addition, electronic photosensitive bodies, image sensors, photoelectric conversion elements, solar cells, etc. can be cited. As display devices, for example, display parts such as organic EL panel modules, televisions, mobile phones, tablet computers, or personal computers can be cited. As light-emitting devices, for example, lighting or vehicle lamps can be cited. Example

[0093] Below, enumerate synthesis example and embodiment, feature of the present invention is further specifically described.About material shown below, processing content, processing sequence etc., as long as do not depart from the gist of the present invention, then can suitably change.Therefore, the scope of the present invention is not limited to following embodiment.

[0094] [Example 1] <Synthesis of Compound (89)> Into a nitrogen-purged reaction vessel, 10.0 g of N-phenyl-4-(phenylnaphthalen-3-yl)aniline, 9.3 g of 3-(4-chlorophenyl)-1-phenylnaphthalene, 5.2 g of sodium tert-butoxide, 0.3 g of bis(tri(tert-butylphosphine)]palladium(0), and 100 ml of toluene were added, and the mixture was stirred overnight under heating and reflux. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 14.4 g of compound (89) (yield: 82.3%).

[0095] [Chemical formula 9]

[0096] The structure of the obtained white powder was identified using NMR. use 1 By H-NMR (CDCl3), the following 35 hydrogen signals were detected. δ(ppm)=8.05(2H), 7.95(2H), 7.90(2H), 7.71(2H), 7.67(4H), 7.65-7.49(10H), 7.47-7.40(4H), 7.31(2H), 7.26-7.21(6H), 7.08(1H).

[0097] [Example 2] <Synthesis of Compound (13)> In a nitrogen-substituted reaction container, 8.0 g of N-phenyl-4-(4-phenylnaphthalen-1-yl)aniline, 8.5 g of 1-(4-bromophenyl)-4-phenylnaphthalene, 0.2 g of tri(dibenzylideneacetone)palladium(0), 0.2 g of tri-tert-butylphosphine, 3.1 g of tert-butoxysodium, and 80 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by crystallization using a toluene / acetone mixed solvent to obtain 4.3 g of compound (13) (yield: 31.0%).

[0098] [Chemical formula 10]

[0099] The structure of the obtained white powder was identified using NMR. use 1 By H-NMR (CDCl3), the following 35 hydrogen signals were detected. δ(ppm)=8.15(2H), 8.00(2H), 7.59-7.46(22H), 7.43-7.35(8H), 7.15(1H).

[0100] [Example 3] <Synthesis of Compound (23)> In a nitrogen-purged reaction container, 1.8 g of aniline, 12.2 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.7 g of tris(dibenzylideneacetone)palladium(0), 0.3 g of tri-tert-butylphosphine, 7.4 g of tert-butoxysodium and 180 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using ethanol solvent to obtain 4.0 g of compound (23) (yield: 31.8%).

[0101] [Chemical formula 11]

[0102] The structure of the obtained light yellow powder was identified using NMR. use 1 By H-NMR (CDCl3), the following 35 hydrogen signals were detected. δ(ppm)=8.12(2H), 7.99(2H), 7.90(2H), 7.78(2H), 7.59-7.51(14H), 7.48-7.44(4H), 7.30(2H), 7.20-7.16(6H), 7.08(1H).

[0103] [Example 4] <Synthesis of Compound (106)> In a nitrogen-substituted reaction container, 13.3 g of N-{4-(4-phenylnaphthalen-2-yl)phenyl}-[1,1'biphenyl]-4-amine, 10.3 g of 3-(4-chlorophenyl)-1-phenylnaphthalene, 5.7 g of sodium tert-butoxide, 0.3 g of bis[tri(tert-butylphosphine)]palladium(0), and 130 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using n-heptane solvent to obtain 18.4 g of compound (106) (yield: 85.5%).

[0104] [Chemical formula 12]

[0105] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 39 hydrogen signals. δ(ppm)=8.09(2H), 7.99(2H), 7.93(2H), 7.75-7.71(6H), 7.64-7.43(21H), 7.36-7.29(6H).

[0106] [Example 5] <Synthesis of Compound (115)> In a nitrogen-substituted reaction container, 10.0 g of bis{4-(4-phenylnaphthalen-2-yl)phenyl}amine, 3.4 g of 1-bromobenzene-2,3,4,5,6-d6, 0.3 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, 3.4 g of tert-butoxysodium, and 100 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization from a tetrahydrofuran / ethyl acetate mixed solvent to obtain 7.2 g of compound (115) (yield: 63.1%).

[0107] [Chemical formula 13]

[0108] The structure of the obtained white powder was identified using NMR. use 1 The following 30 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=8.88(2H), 7.97(2H), 7.92(2H), 7.74(2H), 7.70(4H), 7.60-7.52(10H), 7.50-7.42(4H), 7.27(4H).

[0109] [Example 6] <Synthesis of Compound (116)> In a nitrogen-purged reaction vessel, 15.0 g of bis[4-{4-(phenyl-d5)naphthyl-2-yl}phenyl]amine, 4.8 g of bromobenzene, Palladium (II) acetate: 0.1 g, tri-tert-butylphosphine: 0.5 g, tert-butoxysodium: 3.7 g, toluene: 150 ml, and the mixture was stirred under heating and reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 11.7 g of compound (116) (yield: 69.3%).

[0110] [Chemical formula 14]

[0111] The structure of the obtained white powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 25 hydrogen signals. δ(ppm)=8.07(2H), 7.99-7.91(4H), 7.74-7.69(6H), 7.54(2H), 7.44(2H), 7.36-7.10(9H).

[0112] [Example 7] <Synthesis of Compound (117)> In a nitrogen-substituted reaction container, 2.5 g of aniline, 21.5 g of 3-(4-bromophenyl-2,3,5,6-d4)-1-phenylnaphthalene, 1.0 g of tri(dibenzylideneacetone)palladium(0), 0.4 g of tri-tert-butylphosphine, 6.5 g of tert-butoxysodium and 150 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by recrystallization using acetone solvent to obtain 11.2 g of compound (117) (yield: 63.4%).

[0113] [Chemical formula 15]

[0114] The structure of the obtained white powder was identified using NMR. use 1 The following 27 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=8.08(2H), 7.98(2H), 7.92(2H), 7.74(2H), 7.60-7.52(10H), 7.50-7.42(4H), 7.34(2H), 7.26(2H), 7.11(1H).

[0115] [Example 8] <Synthesis of Compound (118)> In a nitrogen-substituted reaction container, 15.0 g of bis[4-{4-(phenyl-d5)naphthalen-2-yl}phenyl]amine, 5.0 g of 1-bromobenzene-2,3,4,5,6-d6, 0.1 g of palladium(II) acetate, 0.5 g of tri-tert-butylphosphine, 3.7 g of tert-butoxysodium, and 150 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 12.8 g of compound (118) (yield: 75.1%).

[0116] [Chemical formula 16]

[0117] The structure of the obtained white powder was identified using NMR. use 1 The following 20 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=8.07(2H), 7.99-7.91(4H), 7.74-7.69(6H), 7.53(2H), 7.44(2H), 7.28-7.10(4H).

[0118] [Example 9] <Synthesis of Compound (171)> In a nitrogen-substituted reaction container, 4-{1-(dibenzofuran-4-yl)naphthalene-2-yl}-N-phenylaniline: 9.0 g, 7-(4-chlorophenyl)-1-phenylnaphthalene: 6.8 g, tri(dibenzylideneacetone)palladium(0): 0.2 g, tri-tert-butylphosphine: 0.2 g, tert-butoxysodium: 2.8 g, and toluene: 100 ml were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by crystallization using a dichloromethane / methanol mixed solvent to obtain compound (171): 11.5 g (yield: 80.0%).

[0119] [Chemical formula 17]

[0120] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (DMSO-d6) detected the following 37 hydrogen signals. δ(ppm)=8.17-8.07(5H), 7.99-7.94(2H), 7.80-7.72(2H), 7.62-7.27(17H), 7.17(2H), 7.04-6.97(3H), 6.72(2H), 6.64(2H), 6.53(2H).

[0121] [Example 10] <Synthesis of Compound (174)> In a nitrogen-substituted reaction container, 4-{1-(dibenzofuran-4-yl)naphthalene-2-yl}-N-phenylaniline: 10.0 g, 4-{2-(4-chlorophenyl)naphthalene-1-yl}dibenzofuran: 9.6 g, tri(dibenzylideneacetone)palladium(0): 0.2 g, tri-tert-butylphosphine: 0.2 g, tert-butoxysodium: 3.1 g, and toluene: 100 ml were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using chlorobenzene solvent to obtain 10.0 g of compound (174) (yield: 55.5%).

[0122] [Chemical formula 18]

[0123] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (DMSO-d6) detected the following 39 hydrogen signals. δ(ppm)=8.17-8.06(8H), 7.69(2H), 7.58-7.56(4H), 7.49-7.31(12H), 7.06-7.00(2H), 6.91-6.84(5H), 6.35(2H), 6.24-6.18(4H).

[0124] [Example 11] <Synthesis of Compound (177)> In a nitrogen-substituted reaction container, 7.9 g of N-{4-(4-phenylnaphthalen-1-yl)phenyl}-[1,1'-biphenyl]-4-amine, 7.0 g of 1-(4-bromophenyl)-4-phenylnaphthalene, 0.2 g of tri(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, 2.5 g of tert-butoxysodium, and 80 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by recrystallization from a toluene solvent to obtain 10.0 g of Compound (177) (yield: 78.0%).

[0125] [Chemical formula 19]

[0126] The structure of the obtained light yellow powder was identified using NMR. use 1H-NMR (CDCl3) detected the following 39 hydrogen signals. δ(ppm)=8.17(2H), 8.02(2H), 7.68-7.63(4H), 7.60-7.47(24H), 7.42(6H), 7.37(1H).

[0127] [Example 12] <Synthesis of Compound (183)> In a nitrogen-substituted reaction container, 4-([1,1'-binaphthyl]-3-yl)-N-phenylaniline: 10.0 g, 3-(4-chlorophenyl)-1-phenylnaphthalene: 7.8 g, tri(dibenzylideneacetone)palladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, tert-butoxysodium: 3.4 g, and xylene: 100 ml were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using n-heptane solvent to obtain 12.6 g of compound (183) (yield: 75.9%).

[0128] [Chemical formula 20]

[0129] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 37 hydrogen signals. δ(ppm)=8.18(1H), 8.07(1H), 8.07-7.96(4H), 7.93(1H), 7.83(1H), 7. 74-7.68(5H), 7.64(1H), 7.51-7.41(12H), 7.36-7.23(10H), 7.10(1H).

[0130] [Example 13] <Synthesis of Compound (184)> In a nitrogen-substituted reaction container, 4-([1,2'-binaphthyl]-3-yl)-N-phenylaniline: 15.6 g, 3-(4-chlorophenyl)-1-phenylnaphthalene: 11.7 g, tri(dibenzylideneacetone)palladium(0): 0.7 g, tri-tert-butylphosphine: 0.3 g, tert-butoxysodium: 7.1 g, and xylene: 160 ml were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization from a toluene / ethyl acetate mixed solvent to obtain 20.0 g of compound (184) (yield: 74.1%).

[0131] [Chemical formula 21]

[0132] The structure of the obtained white powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 37 hydrogen signals. δ(ppm)=8.12(1H), 8.07(2H), 8.01(2H), 7.99-7.92(5H), 7.84(1H), 7.74-7.6 9(6H), 7.60-7.52(8H), 7.50-7.43(3H), 7.34(2H), 7.30-7.24(6H), 7.11(1H).

[0133] [Example 14] <Synthesis of Compound (186)> In a nitrogen-substituted reaction container, 7.5 g of 4-([1,1'-binaphthyl]-3-yl)-N-phenylaniline, 6.2 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.2 g of bis(tri(tert-butylphosphine))palladium(0), 2.6 g of sodium tert-butoxide, and 70 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 10.0 g of compound (186) (yield: 80.0%).

[0134] [Chemical formula 22]

[0135] The structure of the obtained white powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 37 hydrogen signals. δ(ppm)=8.16(1H), 8.11(1H), 8.01-7.97(4H), 7.89(1H), 7.81-7.76(2H), 7.09 (2H), 7.63(1H), 7.58-7.41(15H), 7.34-7.27(3H), 7.24-7.18(6H), 7.08(1H).

[0136] [Example 15] <Synthesis of Compound (190)> In a nitrogen-purged reaction container, 7.0 g of N-phenyl-4-(4-phenylnaphthalen-2-yl)-aniline, 7.6 g of 3-(3-chlorophenyl)-1,1'-binaphthyl, 0.2 g of bis[tri(tert-butylphosphine)]palladium(0), 2.7 g of tert-butoxysodium, and 70 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by recrystallization using n-heptane solvent to obtain 11.9 g of compound (190) (yield: 90.2%).

[0137] [Chemical formula 23]

[0138] The structure of the obtained white powder was identified using NMR. use 1 H-NMR (CDCl3) detected the following 37 hydrogen signals. δ(ppm)=8.10(1H), 8.06(1H), 8.00-7.95(4H), 7.92(1H), 7.76(1H), 7.72 (1H), 7.68(2H), 7.63-7.38(16H), 7.34-7.23(8H), 7.17(1H), 7.08(1H).

[0139] [Example 16] <Synthesis of Compound (191)> In a nitrogen-substituted reaction container, 10.0 g of N-phenyl-4-(4-phenylnaphthalen-2-yl)-aniline, 11.4 g of 4-{2-(4-chlorophenyl)naphthalen-1-yl}dibenzofuran, 0.5 g of tri(dibenzylideneacetone)palladium(0), 0.2 g of tri-tert-butylphosphine, 3.1 g of tert-butoxysodium, and 100 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 14.7 g of compound (191) (yield: 73.8%).

[0140] [Chemical formula 24]

[0141] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (DMSO-d6) detected the following 37 hydrogen signals. δ(ppm)=8.21-8.16(4H), 8.09(2H), 7.80(1H), 7.75(1H), 7.67-7.56(10H), 7.53-7.37(8H), 7.19(2H), 7.06(2H), 7.00(1H), 6.74-6.69(6H).

[0142] [Example 17] <Synthesis of Compound (192)> In a nitrogen-substituted reaction container, 8.0 g of N-phenyl-4-(4-phenylnaphthalen-2-yl)-aniline, 7.5 g of 6-(4-chlorophenyl)-1-phenylnaphthalene, 0.2 g of bis(tri(tert-butylphosphine))palladium(0), 3.1 g of sodium tert-butoxide and 100 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 10.3 g of compound (192) (yield: 73.6%).

[0143] [Chemical formula 25]

[0144] The structure of the obtained white powder was identified using NMR. use 1 By H-NMR (CDCl3), the following 35 hydrogen signals were detected. δ(ppm)=8.13(1H), 8.07(1H), 7.99(2H), 7.92(2H), 7.79(1H), 7.73(1H), 7.69(2H), 7.60-7.43(16H), 7.33(2H), 7.26-7.20(6H), 7.10(1H).

[0145] [Example 18] <Synthesis of Compound (195)> In a nitrogen-substituted reaction vessel, 7.0 g of N-phenyl-4-{4-(phenyl-d5)naphthalen-2-yl}-aniline, 6.4 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.2 g of bis(tri(tert-butylphosphine))palladium(0), 2.7 g of sodium tert-butoxide and 70 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 8.1 g of compound (195) (yield: 66.5%).

[0146] [Chemical formula 26]

[0147] The structure of the obtained white powder was identified using NMR. use 1 The following 30 hydrogen signals were detected by H-NMR (CDCl3). δ(ppm)=8.14(1H), 8.07(1H), 7.99(2H), 7.94-7.89(2H), 7.79(1H), 7.74(1H), 7 .69(2H), 7.60-7.52(8H), 7.48-7.43(3H), 7.33(2H), 7.26-7.20(6H), 7.10(1H).

[0148] [Example 19] <Synthesis of Compound (198)> In a nitrogen-substituted reaction container, 10.0 g of N-phenyl-4-(8-phenylnaphthalen-2-yl)aniline, 8.5 g of 2-(4-chlorophenyl)-6-phenylnaphthalene, 0.5 g of tris(dibenzylideneacetone)palladium(0), 0.2 g of tri-tert-butylphosphine, 3.1 g of sodium tert-butoxide, and 100 ml of xylene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by recrystallization from a toluene solvent to obtain 10.9 g of Compound (198) (yield: 62.3%).

[0149] [Chemical formula 27]

[0150] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (DMSO-d6) detected the following 35 hydrogen signals. δ(ppm)=8.24(2H), 8.11-8.05(3H), 8.01-7.98(2H), 7.98-7.79(7H), 7.61-7.35(14H), 7.17-7.13(7H).

[0151] [Example 20] <Synthesis of Compound (199)> In a nitrogen-substituted reaction container, 7.0 g of N-phenyl-4'-(8-phenylnaphthalen-2-yl)-[1,1'-biphenyl]-4-amine, 5.2 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.1 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, 2.3 g of tert-butoxysodium, and 100 ml of toluene were added, and the mixture was stirred under heating reflux overnight. After confirming the completion of the reaction, the filtrate was concentrated to obtain a crude product. The crude product was isolated by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) and purified by crystallization using a toluene / ethanol mixed solvent to obtain 8.6 g of compound (199) (yield: 76.0%).

[0152] [Chemical formula 28]

[0153] The structure of the obtained light yellow powder was identified using NMR. use 1 H-NMR (DMSO-d6) detected the following 39 hydrogen signals. δ(ppm)=8.15-8.07(3H), 8.00(3H), 7.93(1H), 7.86(1H), 7.76-7.45(22H), 7.36(2H), 7.13-7.09(7H).

[0154] [Synthesis example 1] <Synthesis of Q-1> In a 100 mL reaction container purged with nitrogen, 1-bromobenzene (D-substituted): 16 mmol, 4-tert-butylaniline: 16 mmol, palladium (II) acetate: 0.1 g (1 mmol), sodium tert-butyloxy: 3.0 g (32 mmol), bis (diphenylphosphine) -1,1'-binaphthyl: 0.2 g (1 mmol), toluene: 45 mL were added, and stirred for 24 hours under heating reflux. After the reaction solution was cooled to room temperature, it was filtered under reduced pressure. The filtrate was concentrated and purified by column chromatography to obtain compound <Q-1>: 32.7 g (yield: 78.2%). [Chemical formula 29]

[0155] <Synthesis of Q-2> In a 250 mL reaction container purged with nitrogen, <P-5>: 98 mmol, <Q-1>: 98 mmol, palladium (II) acetate: 0.5 g (2 mmol), sodium tert-butyloxy: 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol), toluene: 200 mL were added, and stirred for 5 hours under heating reflux. After the reaction solution was cooled to room temperature, it was filtered under reduced pressure. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain compound <Q-2>: 34.2 g (yield: 84.1%). [Chemical formula 30]

[0156] <Synthesis of Compound (III-1)> In a nitrogen-purged reaction vessel, 23 mmol of <Q-2> and 120 mL of tert-butylbenzene were added, and after cooling to -78°C, 42.5 mL (68 mmol) of a 1.6 M n-butyllithium hexane solution was added dropwise. The reaction solution was heated to 60°C and stirred for 3 hours, and then nitrogen was purged to distill off the hexane. The reaction solution was cooled to -78°C, and 11.3 g (45 mmol) of boron tribromide was added dropwise. The mixture was stirred at room temperature for 1 hour, and 5.9 g (45 mmol) of N,N-diisopropylethylamine was added dropwise at 0°C, and then stirred at 120°C for 2 hours. The reaction solution was naturally cooled to room temperature, and an aqueous sodium acetate solution was added and stirred for 1 hour, and then ethyl acetate was added to separate the organic layer. The organic layer was concentrated under reduced pressure and purified by column chromatography to obtain 2.7 g of compound (III-1) (yield: 11.4%). [Chemical formula 31]

[0157] [Synthesis Examples 2 to 27] By the same reaction as in Synthesis Example 1, (III-27) was synthesized from compound (III-2).

[0158] [Example 21] The melting point and glass transition point of each compound synthesized in Examples 1 to 20 were measured using a high-sensitivity differential scanning calorimeter (DSC3100SA manufactured by Bruker AXS).

[0159] [Table 1] Melting point(℃) Glass transition point(℃) Compound (89) 216 110 Compound (13) - 110 Compound (23) - 110 Compound (106) - 121 Compound (115) - 109 Compound (116) - 110 Compound (117) - 110 Compound (118) - 110 Compound (171) - 130 Compound (174) 295 151 Compound (177) 240 123 Compound (183) - 129 Compound (184) - 121 Compound (186) - 131 Compound (190) - 121 Compound (191) - 130 Compound (192) - 110 Compound (195) - 110 Compound (198) 216 105 Compound (199) - 121

[0160] As shown in Table 1, each of the compounds synthesized in Examples 1 to 20 had a glass transition point of 100° C. or higher. This confirmed that the thin film state of the compound represented by the general formula (I) was stable.

[0161] [Example 22] On a substrate with ITO, each compound synthesized in Examples 1 to 20 and a compound (HTM-1) described later (for example, Patent Document 8) were deposited with a film thickness of 100 nm by vacuum deposition to prepare a thin film. For each of the produced thin films, the energy level of HOMO (HOMO level) was measured by an ionization potential measuring device (Sumitomo Heavy Industries, Ltd., PYS-202). The absolute value of the measured HOMO level is shown in Table 2.

[0162] [Table 2]

[0163] As shown in Table 2, the absolute value of the HOMO energy level of each compound synthesized in Examples 1 to 20 is larger than the absolute value of the HOMO energy level (5.4 eV) of a general hole transport material such as NPD and TPD or the compound (HTM-1), and has a deeper HOMO energy level. This confirms that the compound represented by the general formula (I) has a good hole transport ability.

[0164] From the above results, it was confirmed that the compound represented by the general formula (I) of the present invention is useful as a host material for a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device.

[0165] [Example 23] The layer structure of the organic EL element produced in this example is shown in FIG. Figure 1 In this embodiment, after a reflective ITO electrode is pre-formed on a glass substrate 1 as a transparent anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a covering layer 10 are sequentially deposited thereon to produce an organic EL element.

[0166] Specifically, a glass substrate 1 having an ITO film with a thickness of 50 nm, a silver alloy reflective film with a thickness of 100 nm, and an ITO film with a thickness of 5 nm was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250° C. for 10 minutes. After that, the glass substrate with a transparent anode was placed in a vacuum deposition machine and decompressed to below 0.001 Pa after being subjected to UV ozone treatment for 2 minutes. Next, the compound (Acceptor-1) and the compound (HTM-1) were binary deposited to cover the transparent anode 2 to form a hole injection layer 3 with a thickness of 10 nm. At this time, the deposition rate ratio was set to Acceptor-1:HTM-1=3:97. On the hole injection layer 3, the compound (HTM-1) was deposited to have a film thickness of 140 nm to form a hole transport layer 4. On the hole transport layer 4, the compound (89) was deposited to have a film thickness of 5 nm to form an electron blocking layer 5. On the electron blocking layer 5, the compound (III-1, blue light-emitting material) and the compound (EMH-1) were binary deposited to form a light-emitting layer with a thickness of 20 nm. At this time, the deposition rate ratio was set to III-1:EMH-1=5:95. On the light-emitting layer 6, the compound (ETM-1) and the compound (ETM-2) were binary deposited to form an electron transport layer 7 with a thickness of 30 nm. At this time, the evaporation rate ratio was set to ETM-1:ETM-2=50:50. On the electron transport layer 7, lithium fluoride was evaporated in a manner to have a film thickness of 1 nm to form an electron injection layer 8. On the electron injection layer 8, magnesium silver alloy was evaporated in a manner to have a film thickness of 12 nm to form a cathode 9. Finally, the compound (CPL-1) was evaporated in a manner to have a film thickness of 60 nm to form a capping layer 10. The organic EL element was produced through the above steps.

[0167] [Chemical formula 32]

[0168] [Chemical formula 33]

[0169] [Chemical formula 34]

[0170] [Examples 24 to 42] In Example 23, an organic EL device was produced under the same conditions except that the compounds shown in the following Table 3 were used instead of the compound (89) as the material of the electron blocking layer 5.

[0171] [Comparative Example 1] For comparison, an organic EL device was produced under the same conditions as in Example 23 except that the following compound (HTM-2) was used instead of the compound (89) as the material of the electron blocking layer 5 .

[0172] [Chemical formula 35] Compounds described in Patent Document 7

[0173] [Comparative Example 2] For comparison, an organic EL device was produced under the same conditions as in Example 23 except that the following compound (HTM-3) was used instead of the compound (89) as the material of the electron blocking layer 5 .

[0174] [Chemical formula 36] Compounds described in Patent Document 7

[0175] [Evaluation of organic EL elements] For the organic EL elements prepared in Examples 23 to 42 and Comparative Examples 1 to 2, a DC voltage was applied in the atmosphere at room temperature, and the element characteristics and element life were measured. The results are summarized in Table 3. The luminous brightness at the start of luminescence (initial brightness) was set to 2000 cd / m 2 When the constant current is driven, the luminous brightness decays to 1900cd / m 2 The device life was measured by the time (corresponding to 95%:95% decay when the initial brightness was 100%).

[0177] As shown in Table 3, the flowing current density is 10 mA / cm 2 The luminous efficiency at a current of 8.24 to 8.26 cd / A in the organic EL elements of Comparative Examples 1 to 2 is high, and is 8.81 to 9.52 cd / A. In addition, the power efficiency is high, and is 8.01 to 8.66 lm / W in the organic EL elements of Examples 23 to 42, which is 7.19 to 7.28 lm / W. In addition, it can be seen that the element life (95% attenuation) is long, and is 450 to 488 hours in the organic EL elements of Examples 23 to 42, which is 349 to 364 hours in the organic EL elements of Comparative Examples 1 to 2.

[0178] [Examples 43 to 120, Comparative Examples 3 to 5] In Example 23, an organic EL element was produced under the same conditions except that the compound shown in Table 4 below was used instead of compound (89) as the material of the electron blocking layer 5, and the compound shown in Table 4 below was used instead of (III-1) as the material of the light-emitting layer 6. The results of evaluating each of the produced organic EL elements in the same order as in the above-mentioned [Evaluation of Organic EL Elements] are shown in Table 4 below. The data in Table 4 are expressed as relative values ​​based on the results of the element of Comparative Example 3. The voltage is expressed as the difference from the value of the element of Comparative Example 3, and the brightness, luminous efficiency, power efficiency and element life are expressed as the relative ratio (multiplier) to the value of the element of Comparative Example 3. [Chemical formula 37]

[0179] As shown in Tables 3 and 4, the compounds represented by the general formula (I) of the present invention have good hole transport properties and excellent electron blocking ability compared to conventional hole transport materials having an arylamine structure. Therefore, it is known that by using the compounds represented by the general formula (I), organic EL elements with high luminous efficiency and long life can be achieved compared to conventional organic EL elements. It is also known that this effect is particularly evident in combination with an organic boron compound represented by the general formula (III-1) or (III-2). Industrial Applicability

[0180] The compound of the present invention has excellent electron blocking ability and hole transport ability, and has high thermal stability in a thin film state. Therefore, the organic EL element using the compound of the present invention can achieve low driving voltage and high luminous efficiency, long element life, for example, can be effectively used for display devices or lighting of household electrical appliances. In addition, the compound of the present invention can also be applied to the electronic device fields such as electronic photoreceptors, image sensors, photoelectric conversion elements, solar cells, etc. Therefore, the industrial availability of the present invention is high. Explanation of symbols

[0181] 1-glass substrate, 2-transparent anode, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-light-emitting layer, 7-electron transport layer, 8-electron injection layer, 9-cathode, 10-covering layer.

Claims

1. A compound represented by the following general formula (I): [Chemical formula 1] In the formula, A represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group, B and C represent which may be the same or different, deuterium-substituted or unsubstituted naphthylene, R1 and R2 may be the same or different from each other. a deuterium-substituted or unsubstituted monovalent aromatic hydrocarbon group, or a deuterium-substituted or unsubstituted monovalent aromatic heterocyclic group, L1, L2 and L3 represent a single bond, which may be the same or different from each other, A-L3 is a deuterium-substituted or unsubstituted divalent aromatic hydrocarbon group, or a deuterium-substituted or unsubstituted divalent aromatic heterocyclic group, and A-L3 is not an unsubstituted aromatic heterocyclic group.

2. The compound according to claim 1, wherein B and C in the general formula (I) may be the same or different from each other. Deuterium-substituted or unsubstituted 1,2-naphthylene, Deuterium-substituted or unsubstituted 1,3-naphthylene, Deuterium-substituted or unsubstituted 1,4-naphthylene, It represents deuterium-substituted or unsubstituted 2,4-naphthylene, deuterium-substituted or unsubstituted 2,5-naphthylene, deuterium-substituted or unsubstituted 2,6-naphthylene, or deuterium-substituted or unsubstituted 2,8-naphthylene.

3. The compound according to claim 2, wherein In the general formula (I), L1 and L2 are Deuterium-substituted or unsubstituted phenylene, or Deuterium-substituted or unsubstituted biphenylene is represented.

4. The compound according to claim 3, wherein In the general formula (I), R1 and R2 are phenyl groups which may be the same or different, deuterium-substituted or unsubstituted, deuterium-substituted or unsubstituted naphthyl, It represents a deuterium-substituted or unsubstituted dibenzofuranyl group, a deuterium-substituted or unsubstituted phenanthryl group, or a deuterium-substituted or unsubstituted biphenyl group.

5. The compound according to claim 4, wherein A in the general formula (I) is Substituted or unsubstituted phenyl, Substituted or unsubstituted naphthyl, The radicals include a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted biphenyl group.

6. The compound according to claim 5, wherein B and C in the general formula (I) are The same groups are represented.

7. The compound according to claim 6, wherein R1 and R2 in the general formula (I) are The same groups are represented.

8. The compound according to claim 6, wherein R1 and R2 in the general formula (I) are Different groups are indicated.

9. The compound according to claim 5, wherein B and C in the general formula (I) are Different groups are indicated.

10. The compound according to claim 9, wherein R1 and R2 in the general formula (I) are The same groups are represented.

11. The compound according to claim 9, wherein R1 and R2 in the general formula (I) are Different groups are indicated.

12. The compound according to claim 1, wherein A thin film with a thickness of 100 nm was prepared by vacuum evaporation of the compound represented by the general formula (I) on a substrate with indium tin oxide. The absolute value of the HOMO energy level of the compound represented by the general formula (I) measured under vacuum using an ionization potential measuring device was greater than 5.60 eV and less than 5.80 eV. 13 . An electron blocking material, comprising the compound according to claim 1 .

14. An organic electroluminescent element comprising: a pair of electrodes; and an organic layer disposed between the pair of electrodes and comprising at least a light-emitting layer, wherein: The compound according to any one of claims 1 to 12 is contained in at least one of the organic layers.

15. The organic electroluminescent element according to claim 14, wherein At least one of the organic layers is an electron blocking layer, and the electron blocking layer contains the compound.

16. The organic electroluminescent element according to claim 15, wherein At least one of the organic layers is a hole transport layer, and the hole transport layer contains a compound represented by the following general formula (II): [Chemical formula 2] In the formula, Ar1 to Ar5 may be the same as or different from each other and represent a substituted or unsubstituted monovalent aromatic hydrocarbon group. Ar6 to Ar8 may be the same as or different from each other and represent a hydrogen atom or a substituted or unsubstituted monovalent aromatic hydrocarbon group, and at least two of Ar6 to Ar8 are hydrogen atoms. n1 represents 0, 1 or 2, Ar3 and Ar4 may be bonded to each other via a single bond to form a ring, They may also be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring. Ar3 or Ar4 may be bonded to a benzene ring to which the -N(Ar3)(Ar4) group is bonded via a single bond to form a ring, or may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

17. The organic electroluminescent element according to claim 16, wherein: A thin film with a thickness of 100 nm was prepared by vacuum evaporation of the compound represented by the general formula (II) on a substrate with indium tin oxide. The absolute value of the HOMO energy level of the compound represented by the general formula (II) measured under vacuum using an ionization potential measuring device was greater than 5.50 eV and less than 5.65 eV.

18. The organic electroluminescent element according to claim 17, wherein The absolute value of the difference in HOMO energy level between the compound represented by the general formula (I) and the compound represented by the general formula (II) is 0.05 eV or more and 0.35 eV or less. 19 . An electronic device comprising: a pair of electrodes; and at least one organic layer disposed between the pair of electrodes, wherein at least one of the organic layers comprises the compound according to claim 1 .

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