Indenoacridine compounds and their uses

Abstract

To provide: a novel indenoacridine compound better in stability against redox and in hole transportability than known conventional compounds; and an organic EL element based on the indenoacridine compound.SOLUTION: An indenoacridine compound represented by general formula (1) or (2) is used.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel indenoacridine compound and an organic EL device using the same. [Background technology]

[0002] Organic electroluminescent devices (OLEDs) are surface-emitting devices that sandwich an organic thin film between a pair of electrodes. They are characterized by their thinness, light weight, wide viewing angle, and fast response, and are used in a variety of display applications. OLEDs utilize light emitted when holes injected from the anode and electrons injected from the cathode recombine in the emissive layer. Their structure is characterized by a multilayer stack consisting of a hole transport layer, an emissive layer, and an electron transport layer. While charge transport layers, such as the hole transport layer and electron transport layer, do not emit light themselves, they facilitate charge injection into the emissive layer and trap the energy of the charges injected into the emissive layer and the excitons generated in the emissive layer. In particular, the use of phosphorescent materials and delayed fluorescent materials that undergo back-exchange crossover from triplet excited states has been increasing in emissive layers, creating a demand for charge transport materials with a higher triplet level than the emissive material.

[0003] Arylamine compounds with hole transport capabilities are used as hole transport materials, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) is widely recognized as a standard material for such amine compounds (e.g., Non-Patent Document 1). However, NPD has an insufficient triplet level in organic EL devices using phosphorescent or delayed fluorescent materials. On the other hand, carbazole compounds are known as the skeleton of hole transport materials with high triplet levels (e.g., Non-Patent Documents 2 and 3). However, these compounds have the problem of low redox stability. Furthermore, N-phenylindenoacridine has been disclosed (Non-Patent Document 4), but its molecular planarity is so high that vapor-deposited films crystallize, making it unusable in organic EL devices. [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Journal of Applied Physics, 2004, Volume 95, Page 7798 [Non-patent document 2] Advanced Materials, 2016, Vol. 28, pp. 7620 [Non-patent document 3] Advanced Functional Materials, 2012, Vol. 22, pp. 2327 [Non-patent document 4] Organic Letters, 2016, Volume 18, Page 2379 Summary of the Invention [Problem to be solved by the invention]

[0005] Conventional hole transport materials such as arylamine compounds and carbazole compounds have room for improvement in triplet energy level or redox stability. An object of the present invention is to provide a novel indenoacridine compound that is superior in triplet energy level and redox stability to those known hole transport materials, and an organic EL device using the indenoacridine compound. [Means for solving the problem]

[0006] As a result of extensive investigations, the present inventors have found that an indenoacridine compound represented by the following general formula (1) or (2) can solve the above problems, and have thus completed the present invention.

[0007] [ka]

[0008] [In general formula (1) and general formula (2), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R8 , and R 9 are each independently It represents any group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, and a biphenylyl group. In general formula (1), L 1 teeth; a monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, and a phenyl group; or Represents a single bond. In general formula (1), Ar 1 teeth; a phenyl group having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the following general formula (1a), and an indenoacridinyl group represented by the following general formula (1b); a monocyclic, linked, or fused aromatic hydrocarbon group having 7 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the following general formula (1a), and an indenoacridinyl group represented by the following general formula (1b); or It represents a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0009] [ka]

[0010] {In general formula (1a), Ar 2 and Ar 3 are each independently; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or represents a monocyclic, linked, or fused ring heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.}

[0011] [ka]

[0012] {In general formula (1b), R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are each independently represents any group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, and a biphenylyl group. In general formula (1), X 1 , X 2 , and X 3 are each independently; a hydrogen atom; a methyl group; an ethyl group; a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms; a methoxy group; an ethoxy group; a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms; a cyano group; a deuterium atom; a triphenylsilyl group; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the following general formula (1c): a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and It represents any group selected from the group consisting of amino groups represented by the following general formula (1c): In general formula (2), Y 1 , Y 2 , and Y 3 is a group in which two of the atoms are hydrogen atoms and the rest are; Methyl group; ethyl group; linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms; methoxy group; ethoxy group; linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms; cyano group; deuterium atom; triphenylsilyl group; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the following general formula (1c): a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and It represents any group selected from the group consisting of amino groups represented by the following general formula (1c):

[0013] [ka]

[0014] {In general formula (1c), Ar 5 and Ar 6 are each independently; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or and represents a monocyclic, linked, or fused heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group. [Effects of the Invention]

[0015] The indenoacridine compound of the present invention has excellent stability against oxidation and reduction due to its structural characteristics, and therefore has the effect of providing a hole transport material having high durability and hole transport property, i.e., an organic EL device having excellent durability and power consumption compared to conventionally known materials. DETAILED DESCRIPTION OF THE INVENTION

[0016] The present invention will be described in detail below.

[0017] In general formula (1) and general formula (2), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 each independently represents any group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, and a biphenylyl group.

[0018] The linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms is not particularly limited, but examples thereof include a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a cyclopropyl group, and a cyclohexyl group.

[0019] The linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms is not particularly limited, but examples thereof include a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, and a stearyloxy group.

[0020] R 1 , R 2 , R 3, R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 Regarding the groups, in terms of excellent hole transport properties, it is preferable that they each independently represent a hydrogen atom, a deuterium atom, a methyl group, a methoxy group, a cyano group, a phenyl group, or a biphenylyl group, it is preferable that they each independently represent a hydrogen atom, a deuterium atom, a methyl group, a methoxy group, a cyano group, a phenyl group, or a biphenylyl group, and it is more preferable that they each independently represent a hydrogen atom, a deuterium atom, a methyl group, or a phenyl group.

[0021] In general formula (1), L 1 represents a monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, and a phenyl group; or a single bond.

[0022] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0023] The monocyclic, linked, or fused-ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms is not particularly limited, and examples thereof include a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a phenanthrene-diyl group, a triphenylene-diyl group, a pyrene-diyl group, an anthracene-diyl group, etc. As described above, these groups may each independently have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, and a phenyl group, and the number of substituents is not particularly limited.

[0024] L 1Specific examples of the alkylene group include, but are not limited to, a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 4,4'-biphenylene group, a 4,3'-biphenylene group, a 4,2'-biphenylene group, a 3,3'-biphenylene group, a 3,2'-biphenylene group, a 2,2'-biphenylene group, a 4,4''-p-terphenylene group, a 4,3''-p-terphenylene group, a 4,2''-p-terphenylene group, a 3,3''-p-terphenylene group, a 3,2''-p-terphenylene group, a 2,2''-p-terphenylene group, a 4,2'-p-terphenylene group, a a 4,3'-p-terphenylene group, a 3,2'-p-terphenylene group, a 3,3'-p-terphenylene group, a 2,3'-p-terphenylene group, a 2,2'-p-terphenylene group, a 4,4''-m-terphenylene group, a 4,3''-m-terphenylene group, a 4,2''-m-terphenylene group, a 3,3''-m-terphenylene group, a 3,2''-m-terphenylene group, a 2,2''-m-terphenylene group, a 4,2'-m-terphenylene group, a 4,4'-m-terphenylene group, a 4,5'-m-terphenylene group, a 4,6'-m-terphenylene group, ,2'-m-terphenylene group, 3,4'-m-terphenylene group, 3,5'-m-terphenylene group, 3,6'-m-terphenylene group, 2,2'-m-terphenylene group, 2,4'-m-terphenylene group, 2,5'-m-terphenylene group, 2,6'-m-terphenylene group, 4,4''-o-terphenylene group, 4,3''-o-terphenylene group, 4,2''-o-terphenylene group, 3,3''-o-terphenylene group, 3,2''-o-terphenylene group, 2,2''-o-terphenylene group, 4,3'-o-terphenylene group, 4,4'- o-terphenylene group, 4,5'-o-terphenylene group, 4,6'-o-terphenylene group, 3,3'-o-terphenylene group, 3,4'-o-terphenylene group, 3,5'-o-terphenylene group, 3,6'-o-terphenylene group, 2,3'-o-terphenylene group, 2,4'-o-terphenylene group, 2,5'-o-terphenylene group, 2,6'-o-terphenylene group, 1,2-naphthylene group, 1,3-naphthylene group, 1,4-naphthylene group, 1,5-naphthylene group, 1,6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group, 2,4-naphthylene group, 2,5-naphthylene group, 2,6-naphthylene group, 2,7-naphthylene group, 2,8-naphthylene group, 9,9-dimethyl-fluorene-2,7-diyl group, 9,9-dimethyl-fluorene-2,8-diyl group, 9,9-dimethyl-fluorene-2,4-diyl group, 9,9-dimethyl-fluorene-2,5-diyl group, 9,9-dimethyl-fluorene-2,6-diyl group, 9,9-dimethyl-fluorene-3,6-diyl group, 9,9-diphenyl-fluorene-2,7-diyl group, 9,9-diphenyl-fluorene- 2,8-diyl group, 9,9-diphenyl-fluorene-2,4-diyl group, 9,9-diphenyl-fluorene-2,5-diyl group, 9,9-diphenyl-fluorene-2,6-diyl group, 9,9-diphenyl-fluorene-3,6-diyl group, spirobifluorene-2,7-diyl group, spirobifluorene-2,8-diyl group, spirobifluorene-2,4-diyl group, spirobifluorene-2,5-diyl group, spirobifluorene-2,6-diyl group, spirobifluorene-3,6-diyl group, phenanthrene-9,10-diyl group, phenanthrene-2 ,9-diyl group, phenanthrene-2,10-diyl group, phenanthrene-2,8-diyl group, phenanthrene-2,7-diyl group, phenanthrene-2,6-diyl group, phenanthrene-2,5-diyl group, phenanthrene-2,14-diyl group, phenanthrene-2,3-diyl group, phenanthrene-9,10-diyl group, phenanthrene-3,10-diyl group, phenanthrene-3,9-diyl group, phenanthrene-3,8-diyl group, phenanthrene-3,7-diyl group, phenanthrene-3,6-diyl group, phenanthrene-3,5-diyl group , phenanthrene-4,10-diyl group, phenanthrene-4,9-diyl group, phenanthrene-4,8-diyl group, phenanthrene-4,7-diyl group, phenanthrene-4,6-diyl group, triphenylene-1,3-diyl group, triphenylene-1,4-diyl group, triphenylene-1,5-diyl group, triphenylene-1,6-diyl group, triphenylene-1,7-diyl group, triphenylene-1,8-diyl group, triphenylene-2,3-diyl group, triphenylene-2,4-diyl group, triphenylene-2,5-diyl group, triphenylene-2,Examples of the anthracene include a 6-diyl group, a triphenylene-2,7-diyl group, a triphenylene-3,5-diyl group, a triphenylene-3,6-diyl group, a triphenylene-4,6-diyl group, a pyrene-1,3-diyl group, a pyrene-1,6-diyl group, a pyrene-1,8-diyl group, a pyrene-2,7-diyl group, an anthracene-2,6-diyl group, an anthracene-9,10-diyl group, and a 9,10-diphenylanthracenediyl group.

[0025] L 1 With regard to (a), in view of excellent hole transport properties, (b) is preferably a group selected from the group consisting of a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, and a fluorenylene group (these groups may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, and a phenyl group); or (c) is preferably a single bond, more preferably a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, a 9,9-dimethylfluorenylene group, a 9,9-diphenylfluorenylene group, or a single bond, and more preferably each independently a phenylene group, a biphenylylene group, a terphenylylene group, or a single bond.

[0026] In the general formula (1), Ar 1a phenyl group having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the above general formula (1a), and an indenoacridinyl group represented by the above general formula (1b); a monocyclic, linked or fused ring aromatic hydrocarbon group having 7 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the above general formula (1a), and an indenoacridinyl group represented by the above general formula (1b); or a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0027] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0028] The monocyclic, linked, or fused ring aromatic hydrocarbon group having 7 to 30 carbon atoms is not particularly limited, but examples thereof include a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, and an anthryl group. As described above, these groups may each independently have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the above general formula (1a), and an indenoacridinyl group represented by the above general formula (1b), and the number of substituents is not particularly limited.

[0029] The monocyclic, linked, or fused ring heteroaromatic group having 5 to 20 carbon atoms is not particularly limited, and examples thereof include a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazyl group, an indolyl group, a benzothienyl group, a benzofuranyl group, a benzimidazolyl group, an indazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a 2,1,3-benzothiadiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a 2,1,3-benzoxadiazolyl group, a quinolyl group, an isoquinolyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, a phenoxazinyl group, a phenothiazinyl group, a phenazinyl group, and a thianthrenyl group. As described above, these groups may each independently have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, and the number of substituents is not particularly limited.

[0030] In the general formula (1a), Ar 2 and Ar 3each independently represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or It represents a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0031] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0032] The monocyclic, linked, or fused-ring aromatic hydrocarbon group having 6 to 30 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthryl group, etc. As described above, these groups may each independently have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, and the number of substituents is not particularly limited.

[0033] Regarding the above-mentioned monocyclic, linked, or fused heteroaromatic groups having 5 to 20 carbon atoms, Ar 1 This has the same meaning as the monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms shown by the formula (I).

[0034] In the general formula (1a), Ar 2 and Ar 3In terms of excellent hole transport properties, each of the groups independently represents a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group (each of these groups independently represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, and each independently represents one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0033] It is more preferable that the aryl group is a methyl group, a methoxy group, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group (each of these groups may independently have one or more substituents selected from the group consisting of a methyl group, a methoxy group, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a dibenzothienylphenyl group, a dibenzofuranylphenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0035] In general formula (1b), R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R18 , R 19 , R 20 , and R 21 each independently represents any group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, and a biphenylyl group.

[0036] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0037] In general formula (1b), R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 In terms of excellent hole transport properties, each of the groups is preferably a hydrogen atom, a deuterium atom, a methyl group, a methoxy group, a cyano group, a phenyl group, or a biphenylyl group.

[0038] Ar 1Specific examples of the aryl group include, but are not limited to, a 4-methylphenyl group, a 3-methylphenyl group, a 2-methylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,3,5-trimethylphenyl group, a 2,3,6-trimethylphenyl group, a 3,4,5-trimethylphenyl group, a 4-biphenyl group, a 3-biphenyl group, a 2-biphenyl group, a 2-methyl-1,1'-biphenyl-4-yl group, a 3-methyl-1,1'-biphenyl-4-yl group, a 2'-methyl-1,1'-biphenyl-4-yl group, a 3' -methyl-1,1'-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'-biphenyl-4-yl group, 2',3'-dimethyl-1,1'-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2',5'-dimethyl-1,1'-biphenyl-4-yl group, 2',6'-dimethyl-1,1'-biphenyl-4-yl group, p-terphenyl-2-yl group, p-terphenyl-3-yl group, p-terphenyl-4-yl group, p-terphenyl-2'-yl group, m-terphenyl-2-yl group, m-terphenyl-3-yl group, m-terphenyl-4-yl group, m-terphenyl-2'-yl group, m-terphenyl-4'-yl group, m-terphenyl-5'-yl group, o-terphenyl-2-yl group, o-terphenyl-3-yl group, o-terphenyl-4-yl group, o-terphenyl-3'-yl group, o-terphenyl-4'-yl group, 1- Naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 6-methylnaphthalen-2-yl group, 4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 3-methyl-4-(1-naphthyl)phenyl group, 3-methyl-4-(2-naphthyl)phenyl group, 4-(1-naphthyl)biphenyl group, 4-(2-naphthyl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(2-naphthyl)biphenyl group, 4-(2-methyl (naphthalen-1-yl)phenyl group, 3-(2-methylnaphthalen-1-yl)phenyl group, 4-phenylnaphthalen-1-yl group, 4-(2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 4-(2-methylphenyl)naphthalen-2-yl group, 4-(3-methylphenyl)naphthalen-2-yl group, 4-(4-methylphenyl)naphthalen-2-yl group, tetraphenylsilan-4-yl group, tetraphenylsilan-4-yl group, phenylsilan-3-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4-fluorenyl group, 9,9'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-4-yl group, 4-(9,9'-spirobifluoren-4-yl)phenyl group, 3-(9,9'-spirobifluoren-4-yl)phenyl group, 4-(9,9'-spirobifluoren-4-yl)biphenyl group, 3-(9,9'-spirobifluoren-4-yl)biphenyl group, 4-(9,9'-diphenylfluoren-4-yl)phenyl group, 3-(9,9'-diphenylfluoren-4-yl)phenyl group, 4-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 9-phenanthryl group, 2-phenanthryl group, 4-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)biphenyl group, 3-(1-naphthyl)biphenyl group nyl group, 3-(9-phenanthryl)biphenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-triphenylenyl group, 4-triphenylenyl group, 4-(1-triphenylenyl)phenyl group, 3-(1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 11,11'-dimethylbenzo[a]fluoren-9-yl group, 11,11'-dimethylbenzo[a]fluoren-3-yl group , 11,11'-dimethylbenzo[b]fluoren-9-yl group, 11,11'-dimethylbenzo[b]fluoren-3-yl group, 11,11'-dimethylbenzo[c]fluoren-9-yl group, 11,11'-dimethylbenzo[c]fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2-(2-naphthyl)-3,4 -dimethyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dimethyl-2-imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-diviphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3-methyl methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group, 2,2'-bipyridin-5-yl group, 2,3'-bipyridin-3-yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, pyrazyl group, 1,3,5-triazin group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl-2-benzimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1-methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl-2- Phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzisothiazolyl group, 4-benzisothiazolyl group, 5-benzisothiazolyl group, 6-benzisothiazolyl group, 7-benzisothiazolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzoisoxazolyl group, 4-benzoisoxazolyl group, 5-benzoisoxazolyl group, 6-benzoisoxazolyl group, 7-benzoisoxazolyl group, 2,1,3-benzoxadiazolyl-4-yl group, 2,1,3-benzoxadiazolyl-5-yl group, 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, carbazol-9-yl group, 9-methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol 2-(9-carbazolyl)phenyl group, 3-(9-carbazolyl)phenyl group, 4-(9-carbazolyl)phenyl group, 2-(9-carbazolyl)biphenyl group, 3-(9-carbazolyl)biphenyl group, 4-(9-carbazolyl)biphenyl group, 2-(9-carbazolyl)biphenyl group, 3-(9-carbazolyl)biphenyl group, 4-(9-carbazolyl)biphenyl group, 2 -(9-phenylcarbazol-3-yl)phenyl group, 3-(9-phenylcarbazol-3-yl)phenyl group, 4-(9-phenylcarbazol-3-yl)phenyl group, 2-thianthryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 1-methylindole -2-yl group, 1-phenylindol-2-yl group, 4-(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(2-phenylimidazol-1-yl)phenyl group, 4-(1-phenylimidazol-2-yl)phenyl group, 4-(2,3,4-triphenylimidazol-1-yl)phenyl group, 4-(1-methyl-4,5-diphenylimidazol-2-yl)phenyl group, 4-(2-methylbenzimidazol-1-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 4-(1-methylbenzimidazol-2-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(2-methylbenzimidazol-1-yl)phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(1-methylbenzimidazol-2-yl)phenyl group phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 4-(3,5-diphenyltriazin-1-yl)phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophen-2-yl group, 5-phenylfuran-2-yl group, 4-(5-phenylthiophen-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5-phenylthiophen-2-yl)phenyl group, 3-(5-phenylfuran-2-yl)furan, phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 3-(3-benzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(2-dibenzofuranyl)phenyl group, 4-(4-dibenzofuranyl)phenyl group, 3-(2-dibenzofuranyl)phenyl group, 3-(4-dibenzofuranyl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group Examples include an aryl group, a 3-(2-benzothienyl)biphenyl group, a 3-(3-benzothienyl)biphenyl group, a 4-(2-dibenzothienyl)biphenyl group, a 4-(4-dibenzothienyl)biphenyl group, a 3-(2-dibenzothienyl)biphenyl group, a 3-(4-dibenzothienyl)biphenyl group, a 4-(2-dibenzofuranyl)biphenyl group, a 4-(4-dibenzofuranyl)biphenyl group, a 3-(2-dibenzofuranyl)biphenyl group, a 3-(4-dibenzofuranyl)biphenyl group, a 5-phenylpyridin-2-yl group, a 4-phenylpyridin-2-yl group, and a 5-phenylpyridin-3-yl group.

[0039] Ar 1 Regarding the above, in terms of excellent hole transport properties; a phenyl group having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the general formula (1a) above, and an indenoacridinyl group represented by the general formula (1b) above; a group selected from the group consisting of a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the general formula (1a), and an indenoacridinyl group represented by the general formula (1b)); or a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group), a phenyl group having one or more substituents selected from the group consisting of a methyl group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the general formula (1a) above, and an indenoacridinyl group represented by the general formula (1b) above; a group selected from the group consisting of a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups may independently have one or more substituents selected from the group consisting of a methyl group, a deuterium atom, a phenyl group, a biphenylyl group, and a naphthyl group); or more preferably a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a dibenzothienyl group, and a dibenzofuranyl group); More preferably, the alkyl group is a group selected from the group consisting of a methylphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a triphenylenylphenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a phenylcarbazolylphenyl group, a dibenzothienylphenyl group, a dibenzofuranylphenyl group, a phenyl group substituted with an amino group represented by the general formula (1a), a 12b-methyl-indenoacridinylphenyl group, a biphenylyl group, a carbazolylbiphenyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group.

[0040] In general formula (1), X 1 , X 2 , and X 3 are each independently; a hydrogen atom; a methyl group; an ethyl group; a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms; a methoxy group; an ethoxy group; a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms; a cyano group; a deuterium atom; a triphenylsilyl group; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the above general formula (1c); a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and represents any group selected from the group consisting of amino groups represented by the above general formula (1c).

[0041] In general formula (2), Y 1 , Y 2 , and Y 3 is a group in which two of the atoms are hydrogen atoms and the rest are; Methyl group; ethyl group; linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms; methoxy group; ethoxy group; linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms; cyano group; deuterium atom; triphenylsilyl group; a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the above general formula (1c); a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and represents any group selected from the group consisting of amino groups represented by the above general formula (1c).

[0042] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0043] The above-mentioned monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms are represented by Ar 2 and Ar 3 This has the same meaning as the monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms shown by the formula (I).

[0044] Regarding the above-mentioned monocyclic, linked, or fused heteroaromatic groups having 5 to 20 carbon atoms, Ar 1 This has the same meaning as the monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms shown by the formula (I).

[0045] In the general formula (1c), Ar 5 and Ar 6each independently represents a monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, optionally having one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or It represents a monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0046] For the above-mentioned linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, R 1 These groups have the same meaning as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms and the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, as shown by the symbols ##STR1##

[0047] The above-mentioned monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms are represented by Ar 2 and Ar 3 This has the same meaning as the monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms shown by the formula (I).

[0048] Regarding the above-mentioned monocyclic, linked, or fused heteroaromatic groups having 5 to 20 carbon atoms, Ar 1 This has the same meaning as the monocyclic, linked or fused ring heteroaromatic group having 5 to 20 carbon atoms shown by the formula (I).

[0049] In the general formula (1c), Ar 5 and Ar 6In terms of excellent hole transport properties, each of the groups independently represents a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group (each of these groups independently represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, , naphthyl group, phenanthryl group, triphenylenyl group, triphenylsilyl group, carbazolyl group, dibenzothienyl group, and dibenzofuranyl group), each independently being a phenyl group, biphenyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group, More preferably, each of these groups independently represents a phenyl group, a methylphenyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, and even more preferably each of these groups independently represents a phenyl group, a methylphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a triphenylenylphenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a dibenzothienylphenyl group, a dibenzofuranylphenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0050] In general formula (1), X 1 , X 2 , and X 3 Regarding the above, in terms of excellent hole transport properties, each of the following is independently Hydrogen atom; Deuterium atom; Methyl group; Triphenylsilyl group; a group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the general formula (1c)); a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group); and Preferably, the amino group is a group selected from the group consisting of amino groups represented by the general formula (1c), and in terms of excellent hole transport properties, each independently represents: It is more preferably a group selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a triphenylsilyl group, a phenyl group, a methylphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a triphenylenylphenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a dibenzothienylphenyl group, a dibenzofuranylphenyl group, a phenyl group substituted with an amino group represented by the general formula (1c), a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, and an amino group represented by the general formula (1c).

[0051] In general formula (2), Y 1 , Y 2 , and Y3 Regarding the compound having excellent hole transport properties, two of the atoms are hydrogen atoms and the remaining atoms are: Deuterium atom; Methyl group; Triphenylsilyl group; a group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the general formula (1c)); a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group); or It is preferably an amino group represented by the general formula (1c), In terms of excellent hole transport properties, any two of the atoms are hydrogen atoms and the remaining one is It is more preferably a group selected from the group consisting of a deuterium atom, a methyl group, a triphenylsilyl group, a phenyl group, a methylphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a triphenylenylphenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a dibenzothienylphenyl group, a dibenzofuranylphenyl group, a phenyl group substituted with an amino group represented by the general formula (1c), a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbasolyl group, a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, and an amino group represented by the general formula (1c).

[0052] Examples of indenoacridine compounds represented by general formula (1) or general formula (2) include compounds (A1) to (A178), but the present invention is not limited to these compounds.

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] Among the compounds represented by (A-1) to (A-178), the indenoacridine compounds of the present invention include (A1), (A7), (A15), (A17), (A18), (A19), (A21), (A22), (A25), (A28), (A30), (A31), (A32), (A36), (A39), (A43), (A47), (A48), (A49), and (A50). ), (A51), (A52), (A55), (A56), (A57), (A58), (A59), (A60), (A61), (A62), (A64), (A71), (A75), (A82), (A83), (A115), (A130), (A166), (A168), (A169), (A172) or (A176) are preferred in terms of ease of synthesis.

[0063] Next, a method for producing the indenoacridine compound represented by formula (1) or (2) of the present invention will be described.

[0064] The indenoacridine compounds represented by the general formula (1) or (2) can be synthesized by a known method (aryl amination) using, for example, an indenoacridine compound having a hydrogen atom as a substituent on the nitrogen atom as a starting material. For example, the indenoacridine compound represented by the general formula (1) can be obtained by reacting an indenoacridine compound represented by the following general formula (3) having a hydrogen atom as a substituent on the nitrogen atom with a halogen compound represented by the general formula (4) in the presence of a base using a transition metal catalyst. Furthermore, the indenoacridine compound represented by the general formula (2) can be obtained by reacting an indenoacridine compound represented by the general formula (5) having a hydrogen atom as a substituent on the nitrogen atom with a halogen compound represented by the general formula (6) in the presence of a base using a transition metal catalyst.

[0065] [ka]

[0066] {where, R 1 ~R 9 , Ar 1 , L 1 , X 1 ~X 3 , and Y 1 ~Y 3 represents the same definition as in the general formula (1) or (2). Each Z independently represents a halogen atom (iodine, bromine, chlorine, or fluorine) or a triflate group. In addition, the indenoacridine compounds represented by the general formulas (3) and (5) can be synthesized by a known method (Organic Letters, 2016, Vol. 18, p. 2379).

[0067] The indenoacridine compound of the present invention represented by the general formula (1) or (2) can be used as a material for an organic EL device. That is, an organic EL device containing the indenoacridine compound of the present invention represented by the general formula (1) or (2) can be produced. More specifically, it can be used as the light-emitting layer, hole-transport layer, or hole-injection layer of an organic EL device. That is, the indenoacridine compound of the present invention represented by the general formula (1) or (2) can be used as a hole-transport material for an organic EL light-emitting device. Note that, in terms of hole-transport properties and device life, the indenoacridine compound represented by the general formula (1) or (2) is preferably highly pure. Specifically, it is preferable that the amount of impurities such as halogen atoms and transition metal elements, and impurities such as manufacturing raw materials and by-products, be minimized.

[0068] When the indenoacridine compound represented by the general formula (1) or (2) is used as a hole injection layer or a hole transport layer of an organic EL device, a conventionally used known fluorescent or phosphorescent material or a thermally activated delayed fluorescent material can be used for the light-emitting layer. The light-emitting layer may be formed of only one type of light-emitting material, or may be formed by doping one or more types of light-emitting materials into a host material.

[0069] When forming a hole injection layer and / or a hole transport layer containing the indenoacridine compound represented by the general formula (1) or (2), two or more materials may be contained or laminated as necessary. For example, a known electron-accepting material such as an oxide such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, or hexacyanohexaazatriphenylene may be contained or laminated.

[0070] The indenoacridine compound of the present invention represented by the general formula (1) or (2) can also be used as the light-emitting layer of an organic EL device. When the indenoacridine compound of the general formula (1) or (2) is used as the light-emitting layer of an organic EL device, the indenoacridine compound can be used alone, or can be doped into a known light-emitting host material, or can be doped with a known light-emitting dopant.

[0071] As a method for forming a hole injection layer, a hole transport layer, or a light-emitting layer containing an indenoacridine compound represented by the general formula (1) or (2), known methods such as vacuum deposition, spin coating, and casting can be used.

[0072] The basic structure of an organic EL device that can achieve the effects of the present invention preferably includes a substrate, an anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and a cathode, and some layers may be omitted or added.

[0073] The anode and cathode of the organic EL element are connected to a power source via electrical conductors. By applying a potential between the anode and cathode, the organic EL element is activated and emits light.

[0074] Holes are injected into the organic EL element from the anode, and electrons are injected into the organic EL element at the cathode.

[0075] The organic EL device is typically placed on a substrate, and the anode or cathode can be in contact with the substrate. The electrode in contact with the substrate is conveniently called the lower electrode. Generally, the lower electrode is an anode, but the organic EL device of the present invention is not limited to such a form.

[0076] The substrate may be light-transmitting or opaque, depending on the intended direction of light emission. Light-transmitting properties can be confirmed by electroluminescence emission through the substrate. Transparent glass or plastic is typically employed as the substrate in such cases. The substrate may also be a composite structure comprising multiple layers of materials.

[0077] When electroluminescent light emission is viewed through the anode, the anode is made transparent or substantially transparent to the light emission.

[0078] Typical transparent anode materials for use in the present invention include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), or tin oxide. Other metal oxides, such as aluminum- or indium-doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide, can also be used. In addition to these oxides, metal nitrides, such as gallium nitride, metal selenides, such as zinc selenide, or metal sulfides, such as zinc sulfide, can also be used as anodes.

[0079] The anode can be modified with plasma-deposited fluorocarbon. If electroluminescence is seen only through the cathode, the transmissive characteristics of the anode are not important, and any conductive material can be used, transparent, opaque, or reflective. Examples of conductors for this application include gold, iridium, molybdenum, palladium, platinum, etc.

[0080] A plurality of hole-transporting layers, such as a hole injection layer and a hole transport layer, can be provided between the anode and the light-emitting layer. The hole injection layer and the hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer, and by interposing these layers between the anode and the light-emitting layer, a large number of holes can be injected into the light-emitting layer with a lower electric field.

[0081] In the organic EL device of the present invention, the hole transport layer and / or the hole injection layer contains the indenoacridine compound represented by the general formula (1) or (2) above.

[0082] The hole transport layer and / or hole injection layer may be formed by combining the indenoacridine compound represented by the general formula (1) or (2) with any known hole transport material and / or hole injection material.

[0083] Known hole injection materials and hole transport materials include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers. Although the above-mentioned materials can be used as hole injection materials and hole transport materials, it is preferable to use porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds.

[0084] Representative examples of the aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N' -di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and the like.

[0085] Inorganic compounds such as p-type Si and p-type SiC can also be used as hole injection and transport materials. The hole injection and transport layers may have a single layer structure made of one or more of the above materials, or may have a multilayer structure made of multiple layers of the same or different compositions.

[0086] The light-emitting layer of an organic EL device contains phosphorescent or fluorescent materials, and light is emitted as a result of the recombination of electron-hole pairs in this region.

[0087] The light-emitting layer may consist of a single material, including both small molecules and polymers, but more commonly consists of a host material doped with a guest compound, where emission comes primarily from the dopant and can be of any color.

[0088] Examples of host materials for the light-emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group, such as DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl), TBADN (2-tert-butyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), and 9,10-bis(biphenyl)anthracene.

[0089] The host materials in the light-emitting layer can be an electron-transporting material, as defined below, a hole-transporting material, as defined above, another material that supports hole-electron recombination, or a combination of these materials.

[0090] Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, and carbostyril compounds.

[0091] Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0092] Examples of dopants include Alq3 (tris(8-hydroxyquinoline)aluminum)), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, Ir(PPy)3 (tris(2-phenylpyridine)iridium(III), or FlrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III)).

[0093] Examples of electron transporting materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include 8-hydroxyquinolinatolithium (Liq), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, and tris(8-hydroxyquinolinato) ) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato)-1-naphtholate aluminum, bis(2-methyl-8-quinolinato)-2-naphtholate gallium, and the like.

[0094] A hole-blocking layer may be provided between the light-emitting layer and the electron-transporting layer to improve carrier balance. Desirable compounds for the hole-blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), and bis(10-hydroxybenzo[h]quinolinato)beryllium).

[0095] In the organic EL device of the present invention, an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, luminous efficiency, constant voltage driving, or high durability).

[0096] Desirable compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. In addition, inorganic compounds such as the above-mentioned metal complexes, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, and various oxides, nitrides, and oxynitrides of SiO, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C can also be used.

[0097] When light emission is observed only through the anode, the cathode used in the present invention can be formed from any conductive material. Suitable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al2O3) mixture, indium, lithium / aluminum mixture, rare earth metals, etc. [Example]

[0098] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0099] The analytical instruments used in this example are listed below.

[0100] [NMR measurement] Measurement equipment: Bruker ASCEND 400 [FDMS measurement] Measuring device: Hitachi M-80B [Triplet level measurement] Measurement equipment: JASCO FP-6500 [Redox stability evaluation] Measuring device: Hokuto Denko HSV-110 [Evaluation of hole transport properties] Measurement equipment: ADC SourceMeter 6241A

[0101] [ka]

[0102] Synthesis Example 1 Synthesis of Compound (7) Methyltriphenylphosphonium bromide (15.0 g, 32.3 mmol) was dissolved in THF (30 mL) under an argon atmosphere and then cooled to 0 °C. Potassium tert-butoxide (4.72 g, 42.0 mmol) was added to this solution and stirred at room temperature for 30 minutes. This mixture was again cooled to 0 °C, and a solution of 2-aminobenzophenone (6.37 g, 32.3 mmol) dissolved in THF (70 mL) was added. This suspension was stirred at room temperature for 18 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture to separate the organic layer. Sodium sulfate was added to the organic layer and allowed to stand. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain 5.74 g (29.4 mmol) of the desired compound (7) as a yellow solid (5.74 g, 29.4 mmol, 91% yield).

[0103] Compound identification 1 This was measured by H-NMR.

[0104] 1H-NMR(CDCl3)δ7.35-7.40(m,2H),7.28-7.35(m,3H),7.14(td,J=7.8,1.6Hz,1H),7.11(dd,J=7.5,1.5Hz,1H ),6.79,(t,J=7.4Hz,1H)6.70(d,J=8.1Hz,1H),5.80(d,J=1.1Hz,1H),5.36(d,J=1.1Hz,1H),3.56(brs,2H). Synthesis Example 2: Synthesis of Compound (8) Under an argon atmosphere, compound (7) (5.73 g, 29.4 mmol) obtained in Synthesis Example 1, 1-iodo-2-bromobenzene (8.30 g, 29.4 mmol), tris(dibenzylideneacetone)bispalladium (672 mg, 0.73 mmol), 1,1'-bis(diphenylphosphino)ferrocene (1.63 g, 2.94 mmol), and sodium tert-butoxide (5.64 g, 58.7 mmol) were suspended in toluene (105 mL) and stirred at 110 °C for 17 hours. After completion of the reaction, the reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain the target compound (8) as a white solid (6.96 g, 19.9 mmol, 68% yield).

[0105] Compound identification 1 This was measured by H-NMR.

[0106] 1 H-NMR(CDCl3)δ7.37(dd,J=8.0,1.5Hz,1H),7.26-7.35(m,8H),7.17(dd,J=8.5,1.5Hz,1H),7.04-7.1 1(m,2H),6.65(ddd,7.5,1.5,1.5Hz,1H),5.91(brs,1H),5.80(d,J=1.2Hz,1H),5.38(d,J=1.2Hz,1H). Synthesis Example 3: Synthesis of Compound (9) Under an argon atmosphere, compound (8) (6.96 g, 19.9 mmol) obtained in Synthesis Example 2, palladium acetate (223 mg, 0.99 mmol), 1,1'-bis(diphenylphosphino)ferrocene (1.10 g, 1.99 mmol), potassium carbonate (5.49 g, 39.7 mmol), and pivalic acid (4.06 g, 39.7 mmol) were suspended in dimethylacetamide (125 mL) and stirred at 120 °C for 14 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and then subjected to silica gel column chromatography (hexane / ethyl acetate). Subsequently, 1 M aqueous sodium hydroxide solution and chloroform were added, and the organic layer was separated. Sodium sulfate was added to the organic layer and allowed to stand. The desiccant was then filtered off, and the filtrate was concentrated under reduced pressure to obtain the target compound (9) as a pale yellow solid (3.35 g, 12.4 mmol, 63% yield).

[0107] Compound identification 1 This was measured by H-NMR.

[0108] 1 H-NMR(CDCl3)δ7.94-8.00(m,1H),7.79-7.82(m,1H),7.77(dd,J=7.7,1.3Hz,1H),7.40-7.43(m,2H),7.38(dd,7.5,0.6Hz,1H),7.28(t,J=7.7H) z,1H),7.16(td,J=7.5,1.3Hz,1H),7.03(td,J=7.3,1.2Hz,1H),6.95(dd,J=7.9,1.2Hz,1H),6.83(d,J=7.7Hz,1H),6.29(brs,1H),1.38(s,3H).

[0109] [ka]

[0110] Synthesis Example 4 Synthesis of Compound (10) Under an argon atmosphere, methyltriphenylphosphonium bromide (45.8 g, 128.1 mmol) was dissolved in THF (100 mL) and cooled to 0 °C. Potassium tert-butoxide (14.4 g, 128.1 mmol) was added to this solution and stirred at room temperature for 30 minutes. This mixture was again cooled to 0 °C, and a solution of 2-amino-4'-chlorobenzophenone (7.4 g, 32.3 mmol) dissolved in THF (170 mL) was added. This suspension was stirred at room temperature for 18 hours. After the reaction was completed, water and ethyl acetate were added to separate the organic layer. Sodium sulfate was added to the organic layer and allowed to stand. The desiccant was then filtered off, and the filtrate was concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain the desired compound (10) as a yellow solid (6.6 g, 29.0 mmol, 90% yield).

[0111] Compound identification 1 This was measured by H-NMR. 1 H-NMR(CDCl3)δ7.27-7.32(m,4H),7.15-7.19(m,1H),7.08(dd,J=7.5,1.5Hz,1H),6.79 (td,J=7.5,1.1Hz,1H),6.70(dd,J=8.0,1.1Hz,1H),5.58(d,J=1.2Hz,2H),3.55(s,2H). Synthesis Example 5 Synthesis of Compound (11) Under an argon atmosphere, compound (10) (18.9 g, 82.3 mmol) obtained in Synthesis Example 4, tris(dibenzylideneacetone)bispalladium (1.89 g, 2.06 mmol), 1-bromo-2-iodobenzene (24.4 g, 86.4 mmol), 1,1'-bis(diphenylphosphino)ferrocene (4.56 g, 8.23 ​​mmol), and sodium tert-butoxide (15.8 g, 164.6 mmol) were suspended in toluene (330 mL) and stirred at 110 °C for 18 hours. After completion of the reaction, the reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain the target compound (11) as a white solid (24.8 g, 64.5 mmol, 78% yield).

[0112] Compound identification 1 This was measured by H-NMR. 1 H-NMR(CDCl3)δ7.39(dd,J=7.9,1.3Hz,1H),7.30-7.34(m,3H),7.21-7.26(m, 4H),7.06-7.15(m,3H),6.65-6.69(m,1H),5.86(s,1H),5.59(d,J=1.1Hz,2H). Synthesis Example 6 Synthesis of Compound (12) Under an argon atmosphere, compound (11) (19.7 g, 51.3 mmol) obtained in Synthesis Example 5, palladium acetate (580 mg, 2.57 mmol), 1,1'-bis(diphenylphosphino)ferrocene (2.84 g, 5.13 mmol), calcium carbonate (14.2 g, 102.6 mmol), and pivalic acid (10.5 g, 102.6 mmol) were suspended in dimethylacetamide (250 mL) and stirred at 120 °C for 14 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and then subjected to silica gel column chromatography (hexane / ethyl acetate). Subsequently, 1 M aqueous sodium hydroxide solution and chloroform were added, and the organic layer was separated. Sodium sulfate was added to the organic layer and allowed to stand. The desiccant was then filtered off, and the filtrate was concentrated under reduced pressure to obtain the target compound (12) as a pale yellow solid (11.8 g, 38.8 mmol, 76% yield).

[0113] Compound identification 1 This was measured by H-NMR. 1 H-NMR(CDCl3)δ7.87(d,J=8.1Hz,1H),7.75(d,J=2.0Hz,1H),7.68(dd,J=7.6, 1.2Hz,1H),7.40(dd,J=8.1,2.0Hz,1H),7.34(dd,J=7.5,0.8Hz,1H),7.29(t, J=7.6Hz,1H),7.17(td,J=7.8,1.4Hz,1H),7.03(td,J=7.5,1.2Hz,1H),6.95( dd,J=8.0,1.1Hz,1H),6.85(dd,J=7.6,0.8Hz,1H),6.31(s,1H),1.36(s,3H). Synthesis Example 7 Synthesis of Compound (13) Under an argon atmosphere, compound (12) (200 mg, 0.66 mmol) obtained in Synthesis Example 6, iodobenzene (202 mg, 0.99 mmol), tris(dibenzylideneacetone)bispalladium (30 mg, 33 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (38 mg, 66 μmol), and sodium tert-butoxide (95 g, 0.99 mmol) were suspended in toluene (3 mL) and stirred at 110°C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to give compound (13) as a white powder (129 mg, 0.34 mmol, 52% yield).

[0114] Compound identification 1 This was measured by H-NMR. 1 H-NMR(CDCl3)δ7.92(d,J=8.0Hz,1H),7.79(d,J=2.0Hz,1H),7.73-7.76(m,1H)7.65(t,J=7.3Hz,2H),7.54(tt,J=7.4,1.2Hz,1H),7.43(dd,J=8. 0,1.5Hz,3H),7.36(t,J=7.3Hz,1H),7.19(t,J=7.8,1H),7.01-7.08(m, 2H),6.52-6.56(m,1H),6.44(d,J=8.0Hz,1H),6.31(s,1H),1.48(s,3H). Example 1 (Synthesis of Compound (A1))

[0115] [ka]

[0116] Under an argon atmosphere, compound (9) (2.60 g, 9.66 mmol) obtained in Synthesis Example 3, 5'-bromo-m-terphenyl (3.58 g, 11.6 mmol), tris(dibenzylideneacetone)bispalladium (221 mg, 0.24 mmol), tri-tert-butylphosphonium tetrafluoroborate (308 mg, 1.06 mmol), and sodium tert-butoxide (1.58 g, 16.4 mmol) were suspended in toluene (39 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A1) as a white powder (3.66 g, 7.35 mmol, 76% yield).

[0117] Compound identification 1 This was measured by H-NMR.

[0118] 1 H-NMR(CDCl3)δ8.02-8.04(m,2H),8.01(t,J=1.7Hz,1H),7.84-7.88(m,2H),7.72(dt,J=7.0,1.7Hz,4H), 7.67(d,J=1.7Hz,2H),7.46-7.52(m,6H),7.38-7.44(m,3H),7.22(t,J=7.8Hz,1H), 7.07(dt,J=9.7,1.9Hz,1H),6.72-6.75(m,1H),6.60(t,J=7.8Hz,1H),1.55(s,3H). Example 2 (Synthesis of compound (A18))

[0119] [ka]

[0120] Under an argon atmosphere, compound (9) (1.95 g, 7.24 mmol) obtained in Synthesis Example 3, 9,9-diphenyl-2-bromofluorene (3.16 g, 7.96 mmol), tris(dibenzylideneacetone)bispalladium (165 mg, 0.18 mmol), tri-tert-butylphosphonium tetrafluoroborate (231 mg, 0.79 mmol), and sodium tert-butoxide (1.18 g, 12.3 mmol) were suspended in toluene (30 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the desired compound (A18) as a white powder (2.96 g, 5.06 mmol, 70% yield).

[0121] The compounds were identified by FDMS measurement.

[0122] FDMS:585 Example 3 (Synthesis of compound (A28))

[0123] [ka]

[0124] Under an argon atmosphere, compound (9) (3.90 g, 14.49 mmol) obtained in Synthesis Example 3, 4-triphenylsilylchlorobenzene (5.91 g, 15.93 mmol), tris(dibenzylideneacetone)bispalladium (331 mg, 0.36 mmol), tri-tert-butylphosphonium tetrafluoroborate (462 mg, 1.59 mmol), and sodium tert-butoxide (2.37 g, 24.6 mmol) were suspended in toluene (50 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the desired compound (A28) as a white powder (5.68 g, 9.41 mmol, 65% yield).

[0125] The compounds were identified by FDMS measurement.

[0126] FDMS:603 Example 4 (Synthesis of compound (A30))

[0127] [ka]

[0128] Under an argon atmosphere, compound (9) (2.50 g, 9.29 mmol) obtained in Synthesis Example 3, 3-bromo-9-phenylcarbazole (3.44 g, 10.68 mmol), tris(dibenzylideneacetone)bispalladium (170 mg, 0.19 mmol), tri-tert-butylphosphonium tetrafluoroborate (242 mg, 0.84 mmol), and sodium tert-butoxide (1.52 g, 15.78 mmol) were suspended in toluene (37 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A30) as a white powder (4.00 g, 7.83 mmol, 84% yield).

[0129] Compound identification 1 This was measured by H-NMR.

[0130] 1H-NMR(CDCl3)8.20(d,J=1.7Hz,1H),8.12(d,J=7.8Hz,1H),8.03-8.06(m,1H),7.83-7.88(m,2H),7.68(s,2H), 7.67(d,J=1.0Hz,2H),7.64(d,J=8.7Hz,1H),7.40-7.56(m,5H),7.32(d,J=6.8Hz,2H),7.28(sep,J=7.9 Hz,1H),7.18(t,J=7.6Hz,1H),7.01-7.06(m,2H),6.61-6.66(m,1H),6.48(d,J=7.9Hz,1H),1.57(s,3H). Example 5 (Synthesis of compound (A36))

[0131] [ka]

[0132] Under an argon atmosphere, compound (9) (2.50 g, 9.29 mmol) obtained in Synthesis Example 3, 9-(4-bromophenyl)carbazole (3.44 g, 10.7 mmol), tris(dibenzylideneacetone)bispalladium (170 mg, 0.19 mmol), tri-tert-butylphosphonium tetrafluoroborate (242 mg, 0.84 mmol), and sodium tert-butoxide (1.52 g, 15.8 mmol) were suspended in toluene (37 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A36) as a white powder (4.27 g, 8.36 mmol, 90% yield).

[0133] Compound identification 1 This was measured by H-NMR.

[0134] 1H-NMR(CDCl3)δ8.20(d,J=7.5Hz,2H),8.02-8.07(m,1H),7.85-7.90(m,2H),7.70(dt,J=8.2,2.0Hz,4H), 7.61(d,J=8.2Hz,2H),7.44-7.53(m,5H),7.36(td,J=6.9,1.0Hz,2H),7.28(t,J=8.0Hz,1H),7.1 2(tdd,J=21.9,7.4,1.5Hz,2H),6.72(dd,J=8.0,1.3Hz,1H),6.59(d,J=7.8Hz,1H),1.55(s,3H). Example 6 (Synthesis of compound (A39))

[0135] [ka]

[0136] Under an argon atmosphere, compound (9) (2.50 g, 9.29 mmol) obtained in Synthesis Example 3, 3-(4-bromophenyl)-9-phenylcarbazole (4.07 g, 10.21 mmol), tris(dibenzylideneacetone)bispalladium (43 mg, 0.05 mmol), tri-tert-butylphosphonium tetrafluoroborate (54 mg, 0.19 mmol), and sodium tert-butoxide (1.52 g, 15.78 mmol) were suspended in toluene (37 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A39) as a white powder (5.33 g, 9.08 mmol, 90% yield).

[0137] Compound identification 1 This was measured by H-NMR.

[0138] 1H-NMR(CDCl3)8.49(d,J=1.4Hz,1H),8.24(d,J=7.7Hz,1H),8.01-8.06(m,1H),7.99(d,J=8.4Hz,2H),7.83-7.88(m,2H), 7.78(dd,J=8.4,1.8Hz,Hz,1H),7.61-7.68(m,4H),7.54(d,J=8.6Hz,3H),7.44-7.52(m,5H),7.40(d,J=7.1Hz,1H),7.33-7.37(m ,1H),7.23(t,J=7.1Hz,1H),7.08(tdd,J=22.0,7.4,1.9Hz,2H),6.70(dd,J=7.8,1.6Hz,1H),6.57(d,J=7.8Hz,1H),1.54(s,3H). Example 7 (Synthesis of compound (A43))

[0139] [ka]

[0140] Under an argon atmosphere, compound (9) (1.95 g, 7.24 mmol) obtained in Synthesis Example 3, 4-bromo-4'-(9-carbazolyl)biphenyl (3.17 g, 7.96 mmol), tris(dibenzylideneacetone)bispalladium (82 mg, 0.09 mmol), tri-tert-butylphosphonium tetrafluoroborate (115 mg, 0.39 mmol), and sodium tert-butoxide (0.59 g, 6.1 mmol) were suspended in toluene (15 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A43) as a white powder (3.14 g, 5.35 mmol, 74% yield).

[0141] The compounds were identified by FDMS measurement.

[0142] FDMS:586 Example 8 (Synthesis of compound (A51))

[0143] [ka]

[0144] Under an argon atmosphere, compound (9) (2.50 g, 9.29 mmol) obtained in Synthesis Example 3, 4-(4-bromophenyl)dibenzofuran (3.30 g, 10.21 mmol), tris(dibenzylideneacetone)bispalladium (43 mg, 0.05 mmol), tri-tert-butylphosphonium tetrafluoroborate (54 mg, 0.19 mmol), and sodium tert-butoxide (1.52 g, 15.78 mmol) were suspended in toluene (31 mL) and stirred at 110 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A51) as a white powder (4.39 g, 8.58 mmol, 93% yield).

[0145] Compound identification 1 This was measured by H-NMR.

[0146] 1 H-NMR(CDCl3)8.22(d,J=8.5Hz,2H),8.00-8.06(m,2H),7.86-7.88(m,1H),7.85(d,J=2.0Hz,2H), 7.75(dd,J=7.6,1.2Hz,1H),7.68(d,J=8.2Hz,1H),7.61(d,J=8.6Hz,2H),7.45-7.54(m,4H),7.36(td,J=6.9,1.0Hz,2H), 7.23(t,J=7.5Hz,1H),7.09(tdd,J=23.4,7.4,1.9Hz,2H),6.73(dd,J=7.7,1.3Hz,1H),6.60(d,J=7.7Hz,1H),1.54(s,3H). Example 9 (Synthesis of compound (A64))

[0147] [ka]

[0148] Under an argon atmosphere, compound (9) (2.00 g, 7.43 mmol) obtained in Synthesis Example 3, 3-bromotriphenylamine (2.53 g, 7.80 mmol), tris(dibenzylideneacetone)bispalladium (140 mg, 0.15 mmol), tri-tert-butylphosphonium tetrafluoroborate (190 mg, 0.67 mmol), and sodium tert-butoxide (1.21 g, 12.6 mmol) were suspended in toluene (25 mL) and stirred at 110 °C for 18 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A64) as a white powder (2.87 g, 5.60 mmol, 75% yield).

[0149] Compound identification 1 This was measured by H-NMR.

[0150] 1 H-NMR(CDCl3): δ7.97-7.99(m,1H),7.78-7.83(m,2H),7.37-7.49(m,4H),7.17-7,29(m, 10H),7.00-7.13(m,6H),6.66(dd,J=8.1,1.2Hz,1H),6.50(d,J=7.9Hz,1H),1.43(s,3H). Example 10 (Synthesis of compound (A75))

[0151] [ka]

[0152] Under an argon atmosphere, compound (9) (2.00 g, 7.43 mmol) obtained in Synthesis Example 3, 3-(N-phenyl-N-(dibenzofuran-4-yl)amino)-chlorobenzene (2.88 g, 7.80 mmol), tris(dibenzylideneacetone)bispalladium (140 mg, 0.15 mmol), tri-tert-butylphosphonium tetrafluoroborate (190 mg, 0.67 mmol), and sodium tert-butoxide (1.21 g, 12.6 mmol) were suspended in toluene (25 mL) and stirred at 110 °C for 18 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A75) as a white powder (2.54 g, 4.23 mmol, yield 57%).

[0153] The compounds were identified by FDMS measurement.

[0154] FDMS:602 Example 11 (Synthesis of compound (A115))

[0155] [ka]

[0156] Under an argon atmosphere, compound (13) (2.81 g, 7.43 mmol) obtained in Synthesis Example 7, carbazole (1.30 g, 7.80 mmol), tris(dibenzylideneacetone)bispalladium (140 mg, 0.15 mmol), tri-tert-butylphosphonium tetrafluoroborate (190 mg, 0.67 mmol), and potassium carbonate (1.73 g, 12.6 mmol) were suspended in ortho-xylene (25 mL) and stirred at 140 °C for 24 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A115) as a white powder (0.79 g, 1.56 mmol, 21% yield).

[0157] The compounds were identified by FDMS measurement.

[0158] FDMS:510 Example 12 (Synthesis of compound (A130))

[0159] [ka]

[0160] Under an argon atmosphere, compound (13) (2.81 g, 7.43 mmol) obtained in Synthesis Example 7, 9-phenylcarbazole-3-boronic acid (2.23 g, 7.80 mmol), tetrakis(triphenylphosphine)palladium (0.25 g, 0.22 mmol), 10 mL of tetrahydrofuran, and 10 g of 20 wt% aqueous sodium carbonate solution (18.6 mmol as sodium carbonate) were added and heated to reflux for 10 hours. After cooling to room temperature, the aqueous and organic layers were separated, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A130) as a white powder (3.39 g, 5.79 mmol, 78% yield).

[0161] The compounds were identified by FDMS measurement.

[0162] FDMS:586 Example 13 (Synthesis of compound (A166))

[0163] [ka]

[0164] Under an argon atmosphere, compound (13) (2.81 g, 7.43 mmol) obtained in Synthesis Example 7, diphenylamine (1.31 g, 7.80 mmol), tris(dibenzylideneacetone)bispalladium (140 mg, 0.15 mmol), tri-tert-butylphosphonium tetrafluoroborate (190 mg, 0.67 mmol), and potassium carbonate (1.73 g, 12.6 mmol) were suspended in ortho-xylene (25 mL) and stirred at 140 °C for 12 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A166) as a white powder (2.62 g, 5.12 mmol, yield 69%).

[0165] The compounds were identified by FDMS measurement.

[0166] FDMS:512 Example 14 (Synthesis of compound (A168))

[0167] [ka]

[0168] Under an argon atmosphere, compound (9) (4.08 g, 15.1 mmol) obtained in Synthesis Example 3, 1,3-dibromobenzene (1.68 g, 7.12 mmol), tris(dibenzylideneacetone)dipalladium (280 mg, 0.30 mmol), tri-tert-butylphosphonium tetrafluoroborate (400 mg, 1.36 mmol), and sodium tert-butoxide (2.47 g, 25.7 mmol) were suspended in toluene (61 mL) and stirred at 110 °C for 18 hours. After cooling to room temperature, toluene was added to the reaction mixture, which was then filtered through Celite. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A168) as a white powder (3.24 g, 5.29 mmol, 74% yield).

[0169] Compound identification 1 This was measured by H-NMR.

[0170] 1 H-NMR(CDCl3): δ7.98-8.02(m,2H),7.93(t,J=7.9Hz,1H),7.82-7.87(m,4H),7.65(dd,J=7.9,2.0Hz,2H),7.59(s,1H),7.41-7.48( m,4H),7.23-7.29(m,2H),7.11-7.20(m,4H),7.07(t,J=7.4Hz,2H),6.73(d,J=8.2Hz,2H),6.59(d,J=8.0,2.2Hz,2H),1.49(s,6H). Example 15 (Synthesis of compound (A172))

[0171] [ka]

[0172] Under an argon atmosphere, compound (13) (2.81 g, 7.43 mmol) obtained in Synthesis Example 7, dibenzofuran-4-boronic acid (1.65 g, 7.80 mmol), tetrakis(triphenylphosphine)palladium (0.25 g, 0.22 mmol), 10 mL of tetrahydrofuran, and 10 g of 20 wt% aqueous sodium carbonate solution (18.6 mmol as sodium carbonate) were added and heated to reflux for 10 hours. After cooling to room temperature, the aqueous and organic layers were separated, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (hexane / chloroform) to obtain the target compound (A172) as a white powder (2.80 g, 5.49 mmol, 74% yield).

[0173] The compounds were identified by FDMS measurement.

[0174] FDMS:511 Example 16 (Evaluation of the triplet level of compound (A1)) A solution of compound (A1) in 2-methyltetrahydrofuran at a concentration of 0.0001 mol / L was prepared, and the phosphorescence spectrum was measured under liquid nitrogen cooling. The peak on the short wavelength side of the phosphorescence spectrum was 421 nm. The triplet level estimated from the peak on the short wavelength side of the phosphorescence spectrum is shown in Table 1.

[0175] Examples 17 to 30 (Evaluation of triplet levels of compounds (A18), (A28), (A30), (A36), (A39), (A43), (A51), (A64), (A75), (A115), (A130), (A166), (A168), and (A172)) The phosphorescence spectra of compounds (A18), (A28), (A30), (A36), (A39), (A43), (A51), (A64), (A75), (A115), (A130), (A166), (A168), and (A172) were measured in the same manner as in Example 16. The triplet levels estimated from the rise of the phosphorescence spectra on the short wavelength side are shown in Table 1.

[0176] Comparative Example 1 (Evaluation of Triplet Level of NPD) The phosphorescence spectrum of NPD (N,N'-di-1-naphthyl-N,N'-diphenylbenzidine) was measured in the same manner as in Example 16. The peak at the short wavelength side of the phosphorescence spectrum was 494 nm. The triplet level estimated from the peak at the short wavelength side of the phosphorescence spectrum is shown in Table 1.

[0177] The indenoacridine compounds of the present invention have a higher triplet level than NPD.

[0178] [Table 1]

[0179] Example 31 (Evaluation of redox stability of compound (A168)) The redox stability of compound (A168) was evaluated by cyclic voltammetry. Compound (A168) was dissolved at a concentration of 0.001 mol / L in anhydrous dichloromethane solution containing 0.1 mol / L of tetrabutylammonium perchlorate. A cyclic voltammogram of compound (A168) was obtained using a glassy carbon working electrode, a platinum wire counter electrode, and a silver wire immersed in an acetonitrile solution of AgNO3 as the reference electrode (Figure 1). Compound (A168) exhibited a reversible redox wave and was stable to redox.

[0180] Comparative Example 2 (Evaluation of redox stability of mCBP)

[0181] [ka]

[0182] The redox stability of mCBP was evaluated using the same method as in Example 31. The redox wave of mCBP was irreversible (Figure 2), and it was unstable against redox.

[0183] Example 32 (Evaluation of the hole transport property of compound (A1)) A glass substrate with a 200 nm thick ITO transparent electrode (anode) was cleaned by boiling with isopropyl alcohol. It was then cleaned with ultraviolet ozone and placed in a vacuum deposition apparatus. -4The chamber was evacuated with a vacuum pump until the pressure reached or below Pa. First, a 10-nm hole-injection layer was formed on the ITO transparent electrode by depositing N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane in a mass ratio of 99:1. Subsequently, N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine was deposited at a rate of 0.2 nm / sec to form an 85 nm film, followed by compound (A1) at a rate of 0.2 nm / sec to form a 5 nm film. Furthermore, a 10 nm film of 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene was deposited at a mass ratio of 95:5. Finally, a 50 nm film of silver was deposited at a rate of 0.2 nm / sec to form a cathode. A sealing glass plate was attached with UV-curable resin under a nitrogen atmosphere to form a device for evaluating hole transport properties. A current of 50 mA / cm was applied to the device thus fabricated. 2 A current of 100 kJ / s was applied and the voltage was measured. The results are shown in Table 2.

[0184] Examples 33 to 46 (Evaluation of hole transport properties of compounds (A18), (A28), (A30), (A36), (A39), (A43), (A51), (A64), (A75), (A115), (A130), (A166), (A168), and (A172)) A device for evaluating hole transport properties was prepared in the same manner as in Example 32, except that compound (A1) was replaced with compound (A18), (A28), (A30), (A36), (A39), (A43), (A51), (A64), (A75), (A115), (A130), (A166), (A168), or (A172). 2 Table 2 shows the voltage when a current of this magnitude was applied.

[0185] Comparative Example 3 (Evaluation of the hole transport properties of mCBP) A device for evaluating hole transport properties was prepared in the same manner as in Example 32, except that compound (A1) was changed to mCBP. 2 Table 2 shows the voltage when a current of this magnitude was applied.

[0186] Comparative Example 4 (Evaluation of Hole Transport Properties of N-Phenylindenoacridine)

[0187] [ka]

[0188] A device for evaluating hole transport properties was prepared in the same manner as in Example 32, except that compound (A1) was replaced with N-phenylindenoacridine. N-phenylindenoacridine has high crystallinity, and the thin film crystallized immediately after the device was prepared. 2 When a current of 100 kJ / s was applied, the element shorted out.

[0189] The indenoacridine compounds of the present invention had a lower voltage and superior hole transporting properties compared to mCBP.

[0190] [Table 2] [Brief explanation of the drawings]

[0191] [Figure 1] 1 is a cyclic voltammogram of compound (A168) (see Example 31). [Figure 2] 1 shows a cyclic voltammogram of mCBP (see Comparative Example 2). [Industrial Applicability]

[0192] The indenoacridine compound of the present invention can be used as a material for an organic EL device, for example, as a hole injection material, a hole transport material, or a host material for an emitting layer, and has excellent redox stability and hole transport properties compared to conventionally known materials. Furthermore, the compound can be applied not only as a hole injection material, a hole transport material, or a emitting material for an organic EL device or an electrophotographic photoreceptor, but also in the field of organic photoconductive materials for photoelectric conversion devices, solar cells, image sensors, etc.

Claims

1. The following general formula (1) or general formula (2): 【Chemistry 1】 [In general formula (1) and general formula (2), R １ represents a methyl group, R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , and R ９ represents a hydrogen atom. In general formula (1), L １ teeth; a phenylene group, biphenylylene group, terphenylene group, naphthylene group, fluorenylene group, phenanthrene-diyl group, triphenylene-diyl group, pyrene-diyl group, anthracene-diyl group, each of which may have one or more substituents selected from the group consisting of a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a deuterium atom, and a phenyl group; or Represents a single bond. In general formula (1), Ar １ teeth; a phenyl group having one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the following general formula (1a), and an indenoacridinyl group represented by the following general formula (1b); a monocyclic, linked, or fused-ring aromatic hydrocarbon group having 7 to 30 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the following general formula (1a), and an indenoacridinyl group represented by the following general formula (1b); or It represents a monocyclic, linked, or fused ring heteroaromatic group having 12 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group. 【Chemistry 2】 {In general formula (1a), Ar ２ and Ar ３ are each independently: a monocyclic, linked, or fused-ring aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or represents a monocyclic, linked, or fused ring heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.} 【Transformation 3】 {In general formula (1b), R １０ represents a methyl group, R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , and R ２１ represents a hydrogen atom, R １８ , R １９ , and R ２０ are each independently represents any group selected from the group consisting of a hydrogen atom, a phenyl group, and a biphenylyl group. In general formula (1), X １ , and X ３ is a hydrogen atom, X2 is; a hydrogen atom; a triphenylsilyl group; a monocyclic, linked, or fused-ring aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the following general formula (1c): a monocyclic, linked, or fused ring heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and represents any group selected from the group consisting of amino groups represented by the following general formula (1c): In general formula (2), Y １ , and Y ３ is a hydrogen atom, Y2 is; triphenylsilyl group; a monocyclic, linked, or fused-ring aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the following general formula (1c): a monocyclic, linked, or fused ring heteroaromatic group having 12 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; and represents any group selected from the group consisting of amino groups represented by the following general formula (1c): 【Chemistry 4】 {In general formula (1c), Ar ５ and Ar ６ are each independently: a monocyclic, linked, or fused-ring aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; or represents a monocyclic, linked, or fused-ring heteroaromatic group having 5 to 20 carbon atoms, which may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.}] An indenoacridine compound represented by the formula:

2. L １ but; a group selected from the group consisting of a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, and a fluorenylene group; or The indenoacridine compound of claim 1 , wherein R is a single bond.

3. Ar ２ and Ar ３ and each independently represent a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.

4. Ar １ but; a phenyl group having one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a triphenylsilyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the general formula (1a) above, and an indenoacridinyl group represented by the general formula (1b) above; a group selected from the group consisting of a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, an amino group represented by the general formula (1a), and an indenoacridinyl group represented by the general formula (1b)); or The indenoacridine compound according to any one of claims 1 to 3, which is a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group).

5. X ２ ,but; A hydrogen atom; a triphenylsilyl group; a group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, and a triphenylenyl group (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the general formula (1c)); a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group); or The indenoacridine compound according to any one of claims 1 to 4, wherein the amino group is represented by the general formula (1c):

6. Y ２ but; Triphenylsilyl group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, and triphenylenyl group groups (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, and an amino group represented by the general formula (1c)); a group selected from the group consisting of a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group (each of these groups independently may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group); or The indenoacridine compound according to any one of claims 1 to 5, wherein the amino group is represented by the general formula (1c):

7. Ar ５ and Ar ６ are each independently a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group (each of these groups may independently have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group).

8. The indenoacridine compound according to claim 1, represented by the following formula (A1), (A18), (A28), (A30), (A36), (A39), (A43), (A51), (A64), (A75), (A115), (A130), (A166), (A168) or (A172). 【Transformation 5】 【Transformation 6】

9. A material for an organic EL device, comprising the indenoacridine compound according to any one of claims 1 to 8.

10. A hole transport material for an organic EL device, comprising the indenoacridine compound according to any one of claims 1 to 8.

11. An organic EL device comprising the indenoacridine compound according to any one of claims 1 to 8.

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