Organic electroluminescent elements and electronic devices

Abstract

This invention relates to an organic EL element having a light-emitting layer, a first layer connected to the light-emitting layer on the anode side, and a second layer connected to the light-emitting layer on the cathode side. The light-emitting layer contains a first, a second, and a third compound. The first layer contains a compound of formula (1), and the second layer contains a compound of formula (2). The first compound exhibits fluorescence, and the second compound exhibits delayed fluorescence. The singlet state energies S1 of the first, second, and third compounds satisfy S1(M3) > S1(M2) > S1(M1). In formula (1), Ra1-Ra5, Rb1-Rb5, and Rc1-Rc5 are each independently substituents, etc. In formula (2), X1-X3 are each independently N atoms, etc., and Ar1 and Ar2 are each independently groups of formula (2A) or aryl groups, etc. A is a group of formula (2A). In formula (2A), HAr is represented by formula (2B), a is 1-5, L1 is a linking group, etc. In formula (2B), X 11 ~X 18 Each can be an N atom, etc., and Y1 can be an O atom, S atom, or N atom, etc.

Description

Technical Field

[0001] This invention relates to organic electroluminescent elements and electronic devices. Background Technology

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, while electrons are injected from the cathode. Then, in the light-emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical theorem of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons at a rate of 75%.

[0003] Fluorescent organic EL devices, which emit light from singlet excitons, are being used in full-color displays for mobile phones and televisions, but an internal quantum efficiency of 25% is considered the limit. Therefore, research is underway to improve the performance of organic EL devices.

[0004] Furthermore, it is hoped that triplet excitons, in addition to singlet excitons, can be utilized to make organic EL devices emit light more efficiently. Against this background, a highly efficient fluorescent organic EL device utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") is proposed and investigated.

[0005] For example, the mechanism of Thermally Activated Delayed Fluorescence (TADF) has been studied. This TADF mechanism utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under thermal action, occurring when using materials with a small energy difference (ΔST) between singlet and triplet energy levels. For example, information on thermally activated delayed fluorescence is described in "Chiba Adachi, ed., *Device Properties of Organic Semiconductors*, Kodansha, April 1, 2012, pp. 261-268".

[0006] Patent documents 1 and 2 disclose organic EL elements having a hole transport layer, a light-emitting layer containing a TADF compound, and an electron transport layer. The hole transport layer described in patent documents 1 and 2 does not contain amine compounds. Furthermore, the electron transport layer described in patent documents 1 and 2 comprises compounds having heteroaryl groups directly or via linking groups bonded to an azazine ring having an aryl group.

[0007] Existing technical documents

[0008] Patent documents

[0009] Patent Document 1: International Publication No. 2019 / 013063

[0010] Patent Document 2: International Publication No. 2016 / 056559 Summary of the Invention

[0011] The technical problem that the invention aims to solve

[0012] In organic EL devices that utilize the TADF mechanism, further performance improvements require emission at lower voltages or higher efficiencies.

[0013] The purpose of this invention is to provide an organic electroluminescent element and an electronic device that emits light with low voltage or high efficiency, or with both low voltage and high efficiency.

[0014] Solution to the above technical problems

[0015] According to one aspect of the present invention, the organic electroluminescent element has:

[0016] anode;

[0017] cathode;

[0018] A light-emitting layer is contained between the anode and the cathode;

[0019] The first layer is contained between the anode and the light-emitting layer, and is adjacent to the light-emitting layer;

[0020] The second layer is contained between the cathode and the light-emitting layer, and is adjacent to the light-emitting layer.

[0021] The light-emitting layer comprises a first compound, a second compound, and a third compound.

[0022] The first layer comprises a compound represented by the following general formula (1).

[0023] The second layer comprises a compound represented by the following general formula (2),

[0024] The first compound is a fluorescent compound.

[0025] The second compound is a delayed fluorescence compound.

[0026] The singlet state energies S1(M1) of the first compound, S1(M2) of the second compound, and S1(M3) of the third compound satisfy the following mathematical expression (Form 1).

[0027] S1(M3)>S1(M2)>S1(M1)…(Number 1)

[0028] [Chemistry 1]

[0029]

[0030] In the general formula (1),

[0031] Ra1~Ra5, Rb1~Rb5, and Rc3~Rc5 are each independently hydrogen atoms or substituents, and the substituents Ra1~Ra5, Rb1~Rb5, and Rc3~Rc5 are each independently hydrogen atoms or substituents.

[0032] Halogen atoms,

[0033] cyano,

[0034] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or

[0035] Heteroaryl groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0036] Rc1 is a hydrogen atom or a substituent, or it may bond with Rc2 to form a ring. Rc1 as a substituent is...

[0037] Aryl groups, substituted or unsubstituted, with 6 to 12 carbon atoms in the cyclic group.

[0038] Rc2 is a hydrogen atom or a substituent, or a group of Rc1 and Rc2 bonded together to form a ring. In the case where the group of Rc1 and Rc2 bonded together to form a ring, the ring contains at least a 5-membered ring, which includes at least one of the following atoms: carbon, oxygen, sulfur, and nitrogen. Wherein, Rc1 and Rc2 are not simultaneously hydrogen atoms.

[0039] Rc2 as a substituent is,

[0040] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0041] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0042] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group,

[0043] Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms, or

[0044] Substituted or unsubstituted amino groups.

[0045] [Chemistry 2]

[0046]

[0047] In the general formula (2),

[0048] X1 to X3 are each independently either nitrogen atoms or CR1, wherein at least one of X1 to X3 is a nitrogen atom.

[0049] R1 is a hydrogen atom or a substituent.

[0050] R1, as a substituent, is independently,

[0051] Halogen atoms,

[0052] cyano,

[0053] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0054] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0055] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0056] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0057] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0058] Substituted or unsubstituted silyl groups

[0059] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0060] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0061] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in a cyclic formation.

[0062] Ar1 and Ar2 independently,

[0063] Represented by the following general formula (2A), or as

[0064] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or

[0065] A heteroaryl group with 5 to 30 cyclic atoms, either substituted or unsubstituted.

[0066] A is represented by the following general formula (2A).

[0067] [Chemistry 3]

[0068] (HAr) a -L1- (2A)

[0069] In the general formula (2A),

[0070] HAr is represented by the following general formula (2B),

[0071] a is 1, 2, 3, 4, or 5.

[0072] When a is 1, L1 is a single bond or a divalent linker.

[0073] When a is 2, 3, 4, or 5, L1 is a linking group with a valence of more than three valents but less than six valents.

[0074] Multiple HArs may be the same as or different from each other.

[0075] The linking group is,

[0076] Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0077] Groups derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted.

[0078] A group derived from the group consisting of two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms, or a group derived from the group consisting of two groups bonded together.

[0079] A group derived from the group consisting of three groups selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 cyclic atoms, bonded together.

[0080] In addition, the groups formed by mutual bonding may be the same or different from each other.

[0081] [Chemistry 4]

[0082]

[0083] In the general formula (2B),

[0084] X 11 ~X 18 Each is independently a nitrogen atom, CR 13 Or bonded to the carbon atom of L1,

[0085] Multiple R 13 Whether they are the same or different,

[0086] Y1 represents oxygen atoms, sulfur atoms, and NR. 18 SiR 11 R 12 CR 14 R 15 Nitrogen atoms bonded to L1, and nitrogen atoms bonded to R... 16 And the silicon atoms of L1, or respectively bonded to R 17 And the carbon atoms of L1,

[0087] Among them, X is bonded to L1. 11 ~X 18 R 11 ~R 12 and R 14 ~R 15The carbon atom in Y1, and any one of the nitrogen, silicon, and carbon atoms in Y1.

[0088] R 11 and R 12 Same or different, R 14 and R 15 Same or different,

[0089] R 18 and R 11 ~R 17 Each is independently a hydrogen atom or a substituent, or an adjacent R 13 group, R 11 and R 12 group, R 14 and R 15 A ring is formed by bonding one or more groups together.

[0090] R as a substituent 18 and R 11 ~R 17 Each independently,

[0091] Halogen atoms,

[0092] cyano,

[0093] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0094] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0095] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0096] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0097] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0098] Substituted or unsubstituted silyl groups

[0099] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0100] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0101] (Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group.)

[0102] According to one aspect of the present invention, an electronic device is provided, which is equipped with an organic electroluminescent element according to one aspect of the present invention described above.

[0103] Invention Effects

[0104] According to one aspect of the present invention, it is possible to provide an organic EL element and an electronic device that emits light at low voltage or high efficiency, or emits light at low voltage and high efficiency. Attached Figure Description

[0105] Figure 1 This is a diagram showing a schematic configuration of an example of an organic EL element according to the first embodiment.

[0106] Figure 2 This is a schematic diagram of a device for measuring transient pulse (PL).

[0107] Figure 3 This is a graph showing an example of the decay curve of the transition PL.

[0108] Figure 4 This is a diagram showing the relationship between the energy levels and energy transfer of the first, second, and third compounds in the light-emitting layer of an example of an organic EL element according to the first embodiment. Detailed Implementation

[0109] [First Implementation]

[0110] The structure of the organic EL element according to the first embodiment of the present invention will be described.

[0111] Organic EL devices have an organic layer between the two electrodes, the anode and the cathode. This organic layer is typically composed of multiple layers of organic compounds stacked together. The organic layer may also contain inorganic compounds. At least one layer in the organic layer is a light-emitting layer.

[0112] In this embodiment, the organic layer has a light-emitting layer contained between the anode and the cathode, a first layer contained between the anode and the light-emitting layer and adjacent to the light-emitting layer, and a second layer contained between the cathode and the light-emitting layer and adjacent to the light-emitting layer.

[0113] The luminescent layer comprises a first compound, a second compound, and a third compound. The first compound is a fluorescent compound, and the second compound is a delayed fluorescent compound.

[0114] The first layer comprises a compound represented by general formula (1). There is no particular limitation on the first layer; for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, and an electron blocking layer can be cited. An electron blocking layer is preferred as the first layer.

[0115] The second layer comprises a compound represented by general formula (2). There are no particular limitations on the second layer; for example, at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, and a hole blocking layer can be cited. A hole blocking layer is preferred as the second layer.

[0116] That is, the organic layer of the organic EL element in this embodiment is preferably composed of the following layers.

[0117] Electron blocking layer / light-emitting layer / hole blocking layer

[0118] Hole injection layer / electron blocking layer / light-emitting layer / hole blocking layer

[0119] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer

[0120] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer

[0121] Hole blocking layer / light-emitting layer / hole blocking layer / electron injection layer

[0122] Hole blocking layer / light-emitting layer / hole blocking layer / electron transport layer

[0123] Hole blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0124] Hole injection layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection layer

[0125] Hole injection layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer

[0126] Hole injection layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0127] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection layer

[0128] Hole transport layer / electron blocking layer / luminescent layer / hole blocking layer / electron transport layer

[0129] Hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer

[0130] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron injection layer

[0131] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron transport layer

[0132] Hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron transport layer / electron injection layer

[0133] Figure 1 The diagram shows a schematic configuration of an example of an organic EL element in this embodiment.

[0134] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is composed of a first layer 6, a light-emitting layer 5, and a second layer 7 stacked sequentially from the anode 3 side. The first layer 6 is adjacent to the light-emitting layer 5 on the anode 3 side, and the second layer 7 is adjacent to the light-emitting layer 5 on the cathode 4 side.

[0135] The luminescent layer 5 may also contain a metal complex.

[0136] The light-emitting layer 5 is preferably free of phosphorescent materials (dopants).

[0137] The light-emitting layer 5 is preferably a rare-earth metal complex that does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0138] Furthermore, the light-emitting layer 5 is preferably free of metal complexes.

[0139] The first compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[0140] The second compound is preferably the host material (sometimes also called the matrix material).

[0141] The third compound is preferably the host material. Sometimes, one of the second and third compounds is referred to as the first host material, and the other as the second host material. The third compound can be a delayed-fluorescence compound or a non-delayed-fluorescence compound.

[0142] Previously, organic EL devices were known to possess emissive layers comprising three compounds: a fluorescent compound, a TADF compound, and a third compound. To fabricate organic EL devices that emit light with lower voltage or higher efficiency compared to conventional organic EL devices, it is necessary to improve the hole injection capability into the emissive layer. Furthermore, it is also necessary to retain injected holes within the emissive layer for a longer period and to efficiently generate excitons. However, in the combinations of emissive layers and their surrounding layers (such as electron blocking layers and hole blocking layers) known to date, improvements in hole injection capability into the emissive layer and efficient exciton generation within the emissive layer are insufficient.

[0143] The inventors have discovered that in an organic EL element having a light-emitting layer comprising three compounds, by placing a first layer comprising a compound represented by general formula (1) adjacent to the light-emitting layer on the anode side and placing a second layer comprising a compound represented by general formula (2) adjacent to the light-emitting layer on the cathode side, an organic EL element that emits light with low voltage or high efficiency, or an organic EL element that emits light with low voltage and high efficiency, can be realized.

[0144] The structure of the organic EL element in this embodiment will be described in detail below.

[0145] <First Layer>

[0146] The first layer 6 contains compounds represented by the following general formula (1).

[0147] [Chemistry 5]

[0148]

[0149] In the general formula (1), Ra1~Ra5, Rb1~Rb5, and Rc3~Rc5 are each independently a hydrogen atom or a substituent, and Ra1~Ra5, Rb1~Rb5, and Rc3~Rc5, as substituents, are each independently,

[0150] Halogen atoms,

[0151] cyano,

[0152] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or

[0153] Heteroaryl groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0154] Rc1 is a hydrogen atom or a substituent, or it may bond with Rc2 to form a ring. Rc1 as a substituent is...

[0155] Aryl groups, substituted or unsubstituted, with 6 to 12 carbon atoms in the cyclic group.

[0156] Rc2 is a hydrogen atom or a substituent, or a group of Rc1 and Rc2 bonded together to form a ring. In the case where the group of Rc1 and Rc2 bonded together to form a ring, the ring contains at least a 5-membered ring, which includes at least one of the following atoms: carbon, oxygen, sulfur, and nitrogen. Wherein, Rc1 and Rc2 are not simultaneously hydrogen atoms.

[0157] Rc2 as a substituent is,

[0158] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0159] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0160] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group,

[0161] Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms, or

[0162] Substituted or unsubstituted amino groups.

[0163] In the general formula (1), preferably, when one or more of Ra1 to Ra5 ​​are unsubstituted dibenzofuran groups, none of Rb1 to Rb5 and Rc2 to Rc5 are unsubstituted dibenzofuran groups; when one or more of Rb1 to Rb5 are unsubstituted dibenzofuran groups, none of Ra1 to Ra5 ​​and Rc2 to Rc5 are unsubstituted dibenzofuran groups; when one or more of Rc2 to Rc5 are unsubstituted dibenzofuran groups, none of Ra1 to Ra5 ​​and Rb1 to Rb5 are unsubstituted dibenzofuran groups.

[0164] In the general formula (1), more preferably, when one or more of Ra1 to Ra5 ​​are substituted or unsubstituted dibenzofuran groups, none of Rb1 to Rb5 and Rc2 to Rc5 are substituted or unsubstituted dibenzofuran groups; when one or more of Rb1 to Rb5 are substituted or unsubstituted dibenzofuran groups, none of Ra1 to Ra5 ​​and Rc2 to Rc5 are substituted or unsubstituted dibenzofuran groups; when one or more of Rc2 to Rc5 are substituted or unsubstituted dibenzofuran groups, none of Ra1 to Ra5 ​​and Rb1 to Rb5 are substituted or unsubstituted dibenzofuran groups.

[0165] In the general formula (1), it is preferred that the group of Rc1 and Rc2 is bonded to each other to form a ring.

[0166] In the above general formula (1), it is also preferred that Rc1 is a hydrogen atom or a substituent and Rc2 is a hydrogen atom or a substituent. Wherein, Rc1 and Rc2 are not both hydrogen atoms.

[0167] Here, the following general formula (1A) is used to explain the meaning of the group of Rc1 and Rc2 being bonded to each other to form a ring, and the meaning of at least one of Rc1 and Rc2 being a specific substituent.

[0168] The following general formula (1A) is a local structure of a compound represented by the general formula (1).

[0169] [Chemistry 6]

[0170]

[0171] In the above general formula (1A), Rc1 is synonymous with Rc1 in general formula (1), Rc2 is synonymous with Rc2 in general formula (1), Rc3 to Rc5 are independently synonymous with Rc3 to Rc5 in general formula (1), and * indicates the bonding site of nitrogen atom in the compound represented by general formula (1).

[0172] In the general formula (1A), the group of Rc1 and Rc2 bonded together to form a ring means that Rc1 and Rc2 form a ring Z, for example, represented by the following general formula (11A). 11A .

[0173] [Chemistry 7]

[0174]

[0175] On the other hand, in the general formula (1A), a ring Z is formed between Rc2 and Rc3, represented by the following general formula (11B). 11B The situation where Rc3 and Rc4 form a ring Z represented by the following general formula (11C). 11C In the case of (11B) and (11C), the following general formulas (1A) do not satisfy the general formula (1A).

[0176] [Chemistry 8]

[0177]

[0178] In the compound represented by general formula (1), Rc1 and Rc2 located near the nitrogen atom are bonded together to form the ring Z. 11A Alternatively, at least one of Rc1 and Rc2 has a specific substituent, thus, for example, Rc2 and Rc3 are bonded together to form the ring Z. 11B The compound, Rc3 and Rc4 are bonded together to form the ring Z. 11C Compared to compounds with substituents in Rc3, the nitrogen atom is surrounded by a larger structure. Therefore, it can be considered that the HOMO (highest occupied orbital) orbitals of compounds represented by general formula (1) are narrower, and the ionization potential Ip is deeper (the absolute value is larger).

[0179] Therefore, it can be considered that the organic EL element 1 according to this embodiment improves the hole injection capability into the light-emitting layer and the exciton generation efficiency in the light-emitting layer by including a compound represented by general formula (1) in the first layer adjacent to the light-emitting layer 5 on the anode 3 side. As a result, at least one of driving under low voltage and luminescence under high efficiency is improved.

[0180] In the general formula (1), the part represented by the above general formula (1A) is preferably a group represented by any one of the following general formulas (1A-1) to (1A-10).

[0181] [Chemistry 9]

[0182]

[0183] [Chemistry 10]

[0184]

[0185] In the general formulas (1A-1) to (1A-10), R A R can be either a hydrogen atom or a substituent, and can be a substituent. A Each independently,

[0186] Halogen atoms,

[0187] cyano,

[0188] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0189] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0190] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0191] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0192] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0193] Substituted or unsubstituted silyl groups

[0194] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0195] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0196] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the ring, in the presence of multiple R A In the case of R A If they are the same or different, * indicates the bonding site with the nitrogen atom in the compound represented by general formula (1).

[0197] The group represented by the general formula (1A) is preferably a group represented by any one of the general formulas (1A-1) to (1A-5) and (1A-10), and more preferably a group represented by the general formula (1A-1) or (1A-4).

[0198] The group represented by the general formula (1A) is preferably a group represented by any one of the general formulas (1A-6) to (1A-9), and more preferably a group represented by the general formula (1A-9).

[0199] The group represented by the general formula (1A) is more preferably a group represented by the general formula (1A-1), (1A-4) or (1A-9).

[0200] In the general formulas (1A-1) to (1A-10), R A Hydrogen atoms are preferred.

[0201] In the general formula (1), Ra1 to Ra5 ​​and Rb1 to Rb5 are preferably hydrogen atoms or aryl groups with 6 to 30 cyclic carbons, either substituted or unsubstituted.

[0202] In the general formula (1), it is also preferred that Ra1 to Ra5 ​​are each independently hydrogen atoms, or aryl groups with 6 to 30 cyclic carbon atoms that are substituted or unsubstituted, and that Rb1 to Rb5 are each independently hydrogen atoms, or heteroaryl groups with 5 to 30 cyclic atoms that are substituted or unsubstituted.

[0203] In the general formula (1), it is also preferred that Ra1 to Ra5 ​​are each independently hydrogen atoms or aryl groups with 6 to 30 cyclic carbons obtained by being substituted with heteroaryl groups with 5 to 30 cyclic atoms, and that Rb1 to Rb5 are each independently hydrogen atoms or heteroaryl groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0204] In the general formula (1), it is also preferred that Ra1 to Ra5 ​​and Rb1 to Rb5 are each independently hydrogen atoms, or heteroaryl groups with 5 to 30 substituted or unsubstituted cyclic atoms.

[0205] In the general formula (1), preferably one of Ra1 to Ra5 ​​is a substituent, and Ra1 to Ra5 ​​that is not the substituent is a hydrogen atom, one of Rb1 to Rb5 is a substituent, and Rb1 to Rb5 that is not the substituent is a hydrogen atom, and Rc3 to Rc5 are hydrogen atoms.

[0206] In the general formula (1), Ra1 to Ra5, Rb1 to Rb5 and Rc3 to Rc5, which are substituents, are preferably halogen atoms, cyano groups, unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, respectively.

[0207] In the general formula (1), preferably one of Ra1 to Ra5 ​​is a substituent, and Ra1 to Ra5 ​​that is not the substituent is a hydrogen atom; one of Rb1 to Rb5 is a substituent, and Rb1 to Rb5 that is not the substituent is a hydrogen atom; Rc3 to Rc5 are hydrogen atoms; and Ra1 to Ra5 ​​and Rb1 to Rb5 that are substituents are independently halogen atoms, cyano groups, unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms.

[0208] In the general formula (1), preferably at least one of Ra1 to Ra5 ​​is a group represented by any one of the following general formulas (1B-1) to (1B-10), and at least one of Rb1 to Rb5 is a group represented by any one of the following general formulas (1B-1) to (1B-10).

[0209] [Chemistry 11]

[0210]

[0211] [Chemistry 12]

[0212]

[0213] In the general formulas (1B-1) to (1B-10), R B R is a hydrogen atom or a substituent. B Each independently,

[0214] Halogen atoms,

[0215] cyano,

[0216] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0217] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0218] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0219] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0220] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0221] Substituted or unsubstituted silyl groups

[0222] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0223] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0224] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the ring, in the presence of multiple R B In the case of R B They may be the same or different from each other. * indicates the bonding sites of the benzene rings that are bonded to Ra1-Ra5 and Rb1-Rb5 in the compound represented by general formula (1).

[0225] In the general formulas (1B-1) to (1B-10), R B Hydrogen atoms are preferred.

[0226] The compound represented by the general formula (1) is preferably a compound represented by the following general formula (1X), the following general formula (1Y) or the following general formula (1Z).

[0227] [Chemistry 13]

[0228]

[0229] [Chemistry 14]

[0230]

[0231] In the general formulas (1X), (1Y), and (1Z), at least one of Ra1 to Ra5 ​​is independently a group represented by any one of the general formulas (1B-1) to (1B-10), and at least one of Rb1 to Rb5 is independently a group represented by any one of the general formulas (1B-1) to (1B-10). A R in the general formulas (1A-1) to (1A-10) A Synonyms.

[0232] In the general formulas (1X), (1Y), and (1Z), preferably one of Ra1 to Ra5 ​​is a group represented by any one of the general formulas (1B-1) to (1B-10), and one of Rb1 to Rb5 is a group represented by any one of the general formulas (1B-1) to (1B-10).

[0233] In the general formulas (1X), (1Y), and (1Z), R A Hydrogen atoms are preferred.

[0234] In the general formulas (1X), (1Y), and (1Z), R B Hydrogen atoms are preferred.

[0235] From the viewpoint of improving hole injection into the light-emitting layer and efficiently generating excitons within the light-emitting layer, the ionization potential Ip of the compound represented by the general formula (1) is preferably 5.78 eV or more, more preferably 5.80 eV or more, and even more preferably 5.85 eV or more.

[0236] The method for measuring the ionization potential Ip of the compound represented by the general formula (1) is as described in the examples below.

[0237] Specific examples of compounds represented by general formula (1) are shown below. However, the compounds represented by general formula (1) in this invention are not limited to these specific examples.

[0238] [Chemistry 15]

[0239]

[0240] [Chemistry 16]

[0241]

[0242] [Chemistry 17]

[0243]

[0244] [Chemistry 18]

[0245]

[0246] [Chemistry 19]

[0247]

[0248] [Chemistry 20]

[0249]

[0250] • Method for manufacturing compounds represented by general formula (1)

[0251] Compounds represented by general formula (1) can be manufactured by known methods.

[0252] <Second Layer>

[0253] The second layer 7 contains compounds represented by the following general formula (2).

[0254] [Chemistry 21]

[0255]

[0256] In the general formula (2),

[0257] X1 to X3 are each independently either nitrogen atoms or CR1, wherein at least one of X1 to X3 is a nitrogen atom.

[0258] R1 is a hydrogen atom or a substituent.

[0259] R1, as a substituent, is independently,

[0260] Halogen atoms,

[0261] cyano,

[0262] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0263] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0264] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0265] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0266] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0267] Substituted or unsubstituted silyl groups

[0268] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0269] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0270] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in a cyclic formation.

[0271] Ar1 and Ar2 independently,

[0272] Represented by the following general formula (2A), or as

[0273] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or

[0274] A heteroaryl group with 5 to 30 cyclic atoms, either substituted or unsubstituted.

[0275] A is represented by the following general formula (2A).

[0276] [Chemistry 22]

[0277] (HAr) a -L1- (2A)

[0278] In the general formula (2A),

[0279] HAr is represented by the following general formula (2B),

[0280] a is 1, 2, 3, 4, or 5.

[0281] When a is 1, L1 is a single bond or a divalent linker.

[0282] When a is 2, 3, 4, or 5, L1 is a linking group with a valence of more than three valents but less than six valents.

[0283] Multiple HArs may be the same as or different from each other.

[0284] The linking group is,

[0285] Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0286] Groups derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted.

[0287] A group derived from the group consisting of two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms, or a group derived from the group consisting of two groups bonded together.

[0288] A group derived from the group consisting of three groups selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 cyclic atoms, bonded together.

[0289] In addition, the groups formed by mutual bonding may be the same or different from each other.

[0290] [Chemistry 23]

[0291]

[0292] In the general formula (2B),

[0293] X 11 ~X 18 Each is independently a nitrogen atom, CR 13 Or bonded to the carbon atom of L1,

[0294] Multiple R 13 Whether they are the same or different,

[0295] Y1 represents oxygen atoms, sulfur atoms, and NR. 18 SiR 11 R 12 CR 14 R 15 Nitrogen atoms bonded to L1, and nitrogen atoms bonded to R... 16 And the silicon atoms of L1, or respectively bonded to R 17 And the carbon atoms of L1,

[0296] Among them, X is bonded to L1. 11 ~X 18 R 11 ~R 12 and R 14 ~R 15 The carbon atom in Y1, and any one of the nitrogen, silicon, and carbon atoms in Y1.

[0297] R 11 and R 12 Same or different, R 14 and R 15 Same or different,

[0298] R 18 and R 11 ~R 17 Each is independently a hydrogen atom or a substituent, or an adjacent R 13 group, R 11 and R 12 group, R 14 and R 15 A ring is formed by bonding one or more groups together.

[0299] R as a substituent 18 and R 11 ~R 17 Each independently,

[0300] Halogen atoms,

[0301] cyano,

[0302] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0303] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0304] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0305] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0306] Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0307] Substituted or unsubstituted silyl groups

[0308] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0309] Substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, or

[0310] Aryloxy groups, substituted or unsubstituted, with 6 to 30 carbon atoms in the cyclic group.

[0311] Y1 is bonded to R respectively 16 In the case of silicon atoms of L1, general formula (2B) is represented by the following general formula (2B-1). In general formula (2B-1), X 11 ~X 18 respectively with X in general formula (2B) 11 ~X 18 Synonyms.

[0312] Y1 is bonded to R respectively 17 In the case of L1 carbon atoms, the general formula (2B) is represented by the following general formula (2B-2). In general formula (2B-2), X 11 ~X 18 respectively with X in general formula (2B) 11 ~X 18 Synonyms.

[0313] [Chemistry 24]

[0314]

[0315] In the general formula (2B), L1, which is the linking group, is preferably a residue with a valence of more than two or less than six valences derived from an aryl group with a substituted or unsubstituted cyclic carbon number of 6 to 30.

[0316] In the general formula (2A), a is preferably 1, 2 or 3, more preferably 1 or 2.

[0317] When a is 1, L1 is a divalent linking group, and the general formula (2A) is represented by the following general formula (2A-1).

[0318] When a is 2, 3, 4, or 5, L1 is a linking group with a valence of more than three valents but less than six valents. When a is 2, L1 is a trivalent linking group, and the general formula (2A) is represented by the following general formula (2A-2). In this case, HAr may be the same or different.

[0319] [Chemistry 25]

[0320] (HAr)-L1- (2A-1)

[0321]

[0322] In the general formulas (2A-1) and (2A-2), L1 is a divalent or trivalent linking group, and the linking group is...

[0323] Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0324] Groups derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted.

[0325] A group derived from the group consisting of two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms, or a group derived from the group consisting of two groups bonded together.

[0326] A group derived from the group consisting of three groups selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 cyclic atoms, bonded together.

[0327] In L1 of the general formulas (2A), (2A-1), and (2A-2), the groups formed by the bonding of two or three of these groups refer to groups derived from aryl groups with 6 to 30 carbon atoms and heteroaryl groups with 5 to 30 cyclic atoms, where divalent or trivalent residues are bonded to each other by two or three single bonds. In these linking groups, the bonded groups may be the same or different from each other.

[0328] Preferably, in the general formulas (2A), (2A-1), and (2A-2), L1, as the linking group, is an aryl group with 6 to 30 substituted or unsubstituted cyclic carbons or a heteroaryl group with 5 to 30 substituted or unsubstituted cyclic atoms.

[0329] Preferably, in the general formulas (2A), (2A-1), and (2A-2), L1, as a linking group, is a divalent or trivalent residue derived from any one of benzene, biphenyl, terphenyl, naphthalene, and phenanthrene.

[0330] Preferably, in the general formula (2A), a is 1 or 2, and L1 is a divalent or trivalent linking group.

[0331] Preferably, in the general formula (2A), a is 1, L1 is a linking group, and L1, as a linking group, is a divalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a divalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms.

[0332] Preferably, in the general formula (2A), a is 2, L1 is a linking group, and L1, as a linking group, is a trivalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a trivalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms.

[0333] In the general formula (2A), L1 is preferably a single bond.

[0334] In the general formula (2B), X 13 Or X 16 It is also preferred that the carbon atom is bonded to L1.

[0335] In the general formula (2B), Y1 is preferably NR. 18 Oxygen atom, sulfur atom, CR 14 R 15 Or a nitrogen atom bonded to L1.

[0336] In the general formula (2B), Y1 is preferably CR 14 R 15 .

[0337] Y1 is CR 14 R 15 In the case of X, X is preferred. 11 ~X 18 One of them is a carbon atom bonded to L1, and the other X 11 ~X 18 Nitrogen atom or CR 13 .

[0338] In the general formula (2B), Y1 is preferably NR. 18 Or it may be bonded to a nitrogen atom in L1. Y1 is NR. 18 In the case of X, it is preferable to have X 11 ~X 18 One of them is a carbon atom bonded to L1, and the other X 11 ~X 18 Nitrogen atom or CR 13 When Y1 is a nitrogen atom bonded to L1, X is preferred. 11 ~X 18 Each is independently a nitrogen atom or CR 13 .

[0339] Furthermore, in the general formula (2B), Y1 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0340] Preferably, in the general formula (2B), Y1 is an oxygen atom or a sulfur atom.

[0341] X 11 ~X 18 One of them is a carbon atom bonded to L1, and the others are CR. 13 .

[0342] More preferably, in the general formula (2B), Y1 is an oxygen atom, and X... 11 and X 18 For CR 13 X 12 ~X 17 One of them is a carbon atom bonded to L1, and the others are CR. 13 .

[0343] Preferably, any two or three of X1 to X3 in the general formula (2) are nitrogen atoms.

[0344] When two of X1 to X3 are nitrogen atoms, it is preferable that X1 and X2 are nitrogen atoms and X3 is CR1.

[0345] More preferably, in the general formula (2), X1 and X2 are nitrogen atoms, X3 is CR1, and R1 is a hydrogen atom. In this case, the third compound is represented by the following general formula (21).

[0346] [Chemistry 26]

[0347]

[0348] In the general formula (21), A, Ar1 and Ar2 are synonyms with A, Ar1 and Ar2 in the general formula (2), respectively.

[0349] Specific examples of compounds represented by general formula (2) are shown below. However, the compounds represented by general formula (2) in this invention are not limited to these specific examples.

[0350] [Chemistry 27]

[0351]

[0352] [Chemistry 28]

[0353]

[0354] [Chemistry 29]

[0355]

[0356] [Chemistry 30]

[0357]

[0358] [Chemistry 31]

[0359]

[0360] [Chemistry 32]

[0361]

[0362] [Chemistry 33]

[0363]

[0364] [Chemistry 34]

[0365]

[0366] [Chemistry 35]

[0367]

[0368] [Chemistry 36]

[0369]

[0370] [Chemistry 37]

[0371]

[0372] • Method for manufacturing compounds represented by general formula (2)

[0373] The compound represented by general formula (2) can be manufactured by known methods.

[0374] <Emitting Layer>

[0375] The luminescent layer 5 comprises a first compound, a second compound, and a third compound.

[0376] (First compound)

[0377] The first compound is a fluorescent compound. The first compound can also be a delayed fluorescent compound, or it can be a compound that does not exhibit delayed fluorescence.

[0378] As the first compound in this embodiment, a fluorescent material can be used. Specifically, examples of fluorescent materials include, for instance, diarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, diarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, diarylaminopyrene derivatives, aryl-substituted pyrene derivatives, and diarylamino... Derivatives, aryl substitution Derivatives, diarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indene-perylene derivatives, acenaphthene-fluoranthene derivatives, pyrrole methylene boron complexes, compounds with a pyrrole methylene skeleton, metal complexes of compounds with a pyrrole methylene skeleton, diketopyrrole-pyrrole derivatives, perylene derivatives, and tetraphenyl derivatives, etc.

[0379] The preferred first compound is a compound represented by general formula (20), general formula (30), general formula (40), general formula (50), general formula (I) and general formula (60) described below.

[0380] Compounds represented by general formula (20)

[0381] In this embodiment, the first compound is preferably a compound represented by the following general formula (20).

[0382] [Chemistry 38]

[0383]

[0384] In the general formula (20),

[0385] X is a nitrogen atom or a carbon atom bonded to Y.

[0386] Y is a hydrogen atom or a substituent.

[0387] R 21 ~R 26 Each is independently a hydrogen atom or a substituent, or R 21 and R 22 group, R 22 and R 23 group, R 24 and R 25 The group, and R 25 and R 26 A ring is formed by bonding one or more groups together.

[0388] Y and R as substituents 21 ~R 26 Independently from

[0389] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0390] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0391] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0392] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0393] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0394] Substituted or unsubstituted haloalkoxy groups with 1 to 30 carbon atoms

[0395] Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms

[0396] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group,

[0397] Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms,

[0398] Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted.

[0399] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[0400] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0401] Halogen atoms,

[0402] carboxyl,

[0403] Substituted or unsubstituted ester groups

[0404] Substituted or unsubstituted carbamoyl group,

[0405] Substituted or unsubstituted amino groups

[0406] Nitro,

[0407] cyano,

[0408] Substituted or unsubstituted silyl groups, and

[0409] Selected from the group consisting of substituted or unsubstituted siloxanes.

[0410] Z 21 and Z 22 Each is an independent substituent, or Z 21and Z 22 They bond together to form a ring, with Z acting as a substituent. 21 and Z 22 Independently from

[0411] Halogen atoms,

[0412] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0413] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0414] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0415] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0416] Substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, and

[0417] Selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms in a cyclic structure.

[0418] In the general formula (20), for example, in R 25 and R 26 When the groups bond together to form a ring, the first compound is represented by the following general formula (21).

[0419] [Chemistry 39]

[0420]

[0421] In the general formula (21), X, Y, R 21 ~R 24 Z 21 and Z 22 respectively with X, Y, R in the general formula (20) 21 ~R 24 Z 21 and Z 22 Synonyms, R 27 ~R 30 Each can be an independent hydrogen atom or a substituent, as R. 27 ~R 30 Substituents in the case of substituents, and the substituents of R 21 ~R 24 The listed substituents are synonyms.

[0422] In the general formula (20), in Z 21 and Z 22 When the compounds bond together to form a ring, the first compound is represented, for example, by the following general formula (20A) or the following general formula (20B). However, the first compound is not limited to the following structures.

[0423] [Chemistry 40]

[0424]

[0425] In the general formula (20A), X, Y, and R 21 ~R 26 respectively with X, Y and R in the general formula (20) 21 ~R 26 Synonyms, R 1A Each can be an independent hydrogen atom or a substituent, as R. 1A Substituents in the case of substituents, and the substituents of R 21 ~R 26 The example substituents are synonyms, and n3 is 4.

[0426] In the general formula (20B), X, Y, and R 21 ~R 26 respectively with X, Y and R in the general formula (20) 21 ~R 26 Synonyms, R 1B Each can be an independent hydrogen atom or a substituent, as R. 1B Substituents in the case of substituents, and the substituents of R 21 ~R 26 The example substituents are synonyms, and n4 is 4.

[0427] Z 21 and Z 22 At least one of them (preferably Z) 21 and Z 22 Preferably, the group is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted cyclic aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, and substituted or unsubstituted cyclic aryloxy groups having 6 to 30 carbon atoms.

[0428] Z 21 and Z 22 At least one of them is more preferably a group selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms obtained by substituted with a fluorine atom, an aryloxy group having 6 to 30 cyclic carbon atoms obtained by substituted with a fluorine atom, and an aryloxy group having 6 to 30 cyclic carbon atoms obtained by substituted with a fluoroalkyl group having 1 to 30 carbon atoms.

[0429] Z is further preferred. 21 and Z 22 At least one of them is an alkoxy group having 1 to 30 carbon atoms obtained by substitution with a fluorine atom, more preferably Z.21 and Z 22 An alkoxy group having 1 to 30 carbon atoms obtained by substitution with a fluorine atom.

[0430] Z is also preferred 21 and Z 22 They are the same group.

[0431] On the other hand, the Z is also preferred. 21 and the Z 22 At least one of them is a fluorine atom, and more preferably the Z atom. 21 and the Z 22 It is a fluorine atom.

[0432] Furthermore, the Z is preferred. 21 and the Z 22 At least one of them is a group represented by the following general formula (20a).

[0433] [Chemistry 41]

[0434]

[0435] In the general formula (20a), A is a substituted or unsubstituted alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic aryl group with 6 to 12 carbon atoms; L2 is a substituted or unsubstituted alkylene group with 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic arylene group with 6 to 12 carbon atoms; m is 0, 1, 2, 3, 4, 5, 6, or 7. When m is 2, 3, 4, 5, 6, or 7, the multiple L2s may be the same or different from each other. m is preferably 0, 1, or 2. When m is 0, A is directly bonded to O (oxygen atom).

[0436] In the general formula (20), Z 21 and Z 22 In the case where the group is represented by the general formula (20a), the first compound is represented by the following general formula (22).

[0437] The first compound is preferably a compound represented by the following general formula (22).

[0438] [Chemistry 42]

[0439]

[0440] In the general formula (22), X and X' are carbon atoms bonded to Y, and R' ..."""""'""""""""""""""" "" """ """ """ """ """ """ """ """" """" " 21 ~R 26 respectively with X, Y, R in the general formula (20) 21 ~R 26 Synonyms. A 21 And A22 The term L is synonymous with A in the general formula (20a) and can be the same as or different from each other. 21 and L 22 Synonymous with L2 in the general formula (20a), they may be the same as or different from each other. m1 and m2 are independently 0, 1, 2, 3, 4, 5, 6 or 7, preferably 0, 1 or 2. When m1 is 2, 3, 4, 5, 6 or 7, multiple L 21 Whether they are the same or different, multiple Ls are considered when m2 is 2, 3, 4, 5, 6, or 7. 22 They are the same or different. When m1 is 0, A 21 A is directly bonded to O (oxygen atom), and when m2 is 0, A 22 It bonds directly with O (oxygen atom).

[0441] In the general formula (20a), at least one of A and L2 is preferably substituted with a halogen atom, more preferably with a fluorine atom.

[0442] In the general formula (20a), A is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, or a perfluoroaryl group having 6 to 12 cyclic carbon atoms, and even more preferably a perfluoroalkyl group having 1 to 6 carbon atoms.

[0443] In the general formula (20a), L2 is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms, or a perfluoroaryl group having 6 to 12 cyclic carbon atoms, and even more preferably a perfluoroalkylene group having 1 to 6 carbon atoms.

[0444] That is, the first compound is preferably a compound represented by the following general formula (22a).

[0445] [Chemistry 43]

[0446]

[0447] In the general formula (22a),

[0448] X is synonymous with X in the general formula (20), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (20).

[0449] R 21 ~R 26 Independently related to R in the general formula (20) 21 ~R 26 Synonyms

[0450] m3 is between 0 and 4.

[0451] m4 is between 0 and 4.

[0452] m3 and m4 may be the same as or different from each other.

[0453] In the general formulas (20), (21), (22) and (22a),

[0454] X is a carbon atom bonded to Y.

[0455] Y is a hydrogen atom or a substituent.

[0456] Y, as a substituent, is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, and more preferably substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms.

[0457] In the general formulas (20), (21), (22) and (22a),

[0458] As a better option, the following options can be cited:

[0459] X is a carbon atom bonded to Y.

[0460] Y is a hydrogen atom or a substituent.

[0461] Y, as a substituent, is an aryl group with 6 to 30 cyclic carbons, either substituted or unsubstituted.

[0462] When Y, as a substituent, is an aryl group having 6 to 30 cyclic carbons, the substituent is:

[0463] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0464] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0465] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0466] Substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, or

[0467] Aryl groups with 6 to 30 carbon atoms obtained by substitution with alkyl groups having 1 to 30 carbon atoms.

[0468] In the first compound, it can be the Z 21 With the Z 22 They bond together to form a ring, but preferably the Z... 21 With the Z 22 They did not bond together to form a ring.

[0469] In the general formulas (20), (22) and (22a), R is preferred. 21 R 23 R 24 and R26 At least one of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl halogroup having 1 to 30 carbon atoms.

[0470] In the general formulas (20), (22), and (22a), R is more preferably preferred. 21 R 23 R 24 and R 26 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms. In this case, R is preferred. 22 and R 25 It is a hydrogen atom.

[0471] In the general formulas (20), (22) and (22a), R is preferred. 21 R 23 R 24 and R 26 At least one of them is a substituted or unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0472] In the general formulas (20), (22), and (22a), R is more preferably preferred. 21 R 23 R 24 and R 26 The aryl group is substituted or unsubstituted, with a cyclic carbon number of 6 to 30. In this case, R is preferred. 22 and R 25 It is a hydrogen atom.

[0473] In the general formulas (20), (22) and (22a),

[0474] As a better option, the following options can be cited:

[0475] R 21 R 23 R 24 and R 26 Each independently,

[0476] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[0477] Substituted or unsubstituted alkyl halogroups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[0478] Aryl groups obtained by substitution with alkyl groups having 1 to 30 carbon atoms, resulting in cyclic compounds having 6 to 30 carbon atoms (preferably 6 to 12 carbon atoms).

[0479] R 22 and R 25 It is a hydrogen atom.

[0480] In the general formula (21), R is preferred. 21 R 23 and R 24 At least one of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl halogroup having 1 to 30 carbon atoms.

[0481] In the general formula (21), R is more preferably used. 21 R 23 and R 24 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms. In this case, R is preferred. 22 It is a hydrogen atom.

[0482] In the general formula (21), R is preferred. 21 R 23 and R 24 At least one of them is a substituted or unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0483] In the general formula (21), R is more preferably used. 21 R 23 and R 24 The aryl group is substituted or unsubstituted, with a cyclic carbon number of 6 to 30. In this case, R is preferred. 22 It is a hydrogen atom.

[0484] In the general formula (21),

[0485] As a better option, the following options can be cited:

[0486] R 21 R 23 and R 24 Each independently,

[0487] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[0488] Substituted or unsubstituted alkyl halogroups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[0489] Aryl groups obtained by substitution with alkyl groups having 1 to 30 carbon atoms, resulting in cyclic compounds having 6 to 30 carbon atoms (preferably 6 to 12 carbon atoms).

[0490] R 22 It is a hydrogen atom.

[0491] In the first compound, examples of alkoxy groups obtained by substitution with fluorine atoms include: 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, 2,2,3,3,3-pentafluoro-1-propoxy, 2,2,3,3-tetrafluoro-1-propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 2,2,3,3,4,4,4-heptafluoro-1-butoxy, 2,2,3,3,4,4-hexafluoro-1-butoxy, nonafluorotert-butoxy, 2, 2,3,3,4,4,5,5,5-nonafluoropentoxy, 2,2,3,3,4,4,5,5,6,6,6-undecylfluorohexyloxy, 2,3-bis(trifluoromethyl)-2,3-butadioxy, 1,1,2,2-tetra(trifluoromethyl)ethoxy, 4,4,5,5,6,6,6-heptafluorohexane-1,2-dioxy, and 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecylfluorononane-1,2-dioxy, etc.

[0492] In the first compound, aryloxy groups obtained by substitution with fluorine atoms or by substitution with fluoroalkyl groups can be exemplified by pentafluorophenoxy, 3,4,5-trifluorophenoxy, 4-trifluoromethylphenoxy, 3,5-bistrifluoromethylphenoxy, 3-fluoro-4-trifluoromethylphenoxy, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy, 4-fluorocatechol, 4-trifluoromethylcatechol, and 3,5-bistrifluoromethylcatechol.

[0493] When the first compound is a fluorescent compound, the first compound is preferably one that emits light at a main peak wavelength of 400 nm or more and 700 nm or less.

[0494] In this specification, the main peak wavelength refers to the wavelength at which the measured compound is measured at 10 nm. -6 10 moles per liter or more -5 The fluorescence spectrum of a toluene solution dissolved at a concentration below mol / L was measured at the wavelength of the peak fluorescence spectrum where the luminescence intensity reached its maximum. The measuring apparatus used was a spectrophotometer (Hitachi High-Tech Co., Ltd., F-7000).

[0495] The first compound preferably exhibits red or green luminescence.

[0496] In this specification, red emission refers to emission with the main peak wavelength of the fluorescence spectrum in the range of 600 nm to 660 nm.

[0497] When the first compound is a red fluorescent compound, the main peak wavelength of the first compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less.

[0498] In this specification, green luminescence refers to luminescence with the main peak wavelength of the fluorescence spectrum in the range of 500 nm to 560 nm.

[0499] When the first compound is a green fluorescent compound, the main peak wavelength of the first compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 530 nm or less.

[0500] In this specification, blue emission refers to emission with the main peak wavelength of the fluorescence spectrum in the range of 430 nm to 480 nm.

[0501] When the first compound is a blue fluorescent compound, the main peak wavelength of the first compound is preferably 430 nm or more and 480 nm or less, more preferably 445 nm or more and 480 nm or less.

[0502] Specific examples of compounds represented by general formula (20) are shown below. However, the compounds represented by general formula (20) in this invention are not limited to these specific examples.

[0503] Furthermore, the coordination bonds between boron and nitrogen atoms in the pyrrole methylene skeleton can be marked using various methods, including solid lines, dashed lines, arrows, or omissions. In this specification, they are represented by solid lines, dashed lines, or omitted.

[0504] [Chemistry 44]

[0505]

[0506] [Chemistry 45]

[0507]

[0508] [Chemistry 46]

[0509]

[0510] [Chemistry 47]

[0511]

[0512] [Chemistry 48]

[0513]

[0514] [Chemistry 49]

[0515]

[0516] [Transformation 50]

[0517]

[0518] [Chemistry 51]

[0519]

[0520] [Chemistry 52]

[0521]

[0522] [Chemistry 53]

[0523]

[0524] [Chemistry 54]

[0525]

[0526] [Chemistry 55]

[0527]

[0528] [Chemistry 56]

[0529]

[0530] [Chemistry 57]

[0531]

[0532] [Chem.58]

[0533]

[0534] [Chemistry 59]

[0535]

[0536] [Transformation 60]

[0537]

[0538] [Chemistry 61]

[0539]

[0540] [Chemistry 62]

[0541]

[0542] [Chemistry 63]

[0543]

[0544] [Chemistry 64]

[0545]

[0546] [Chemistry 65]

[0547]

[0548] [Chemistry 66]

[0549]

[0550] Compounds represented by general formula (30)

[0551] In this embodiment, the first compound is preferably a compound (aromatic compound) represented by the following general formula (30).

[0552] [Chemistry 67]

[0553]

[0554] General formula (30) satisfies any one of the following (1) to (4).

[0555] (1)X1~X 20 At least four of them are independently straight-chain or branched alkoxy groups with 1 to 6 carbon atoms, and the rest are hydrogen atoms.

[0556] (2)X1~X 20 At least one of them is a straight-chain or branched alkyl group having 1 to 6 carbon atoms, at least one of them is a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, the total number of the alkyl group and the alkoxy group is 4 or more, and the remainder is hydrogen.

[0557] (3)X1~X 20 At least six of them are independently straight-chain or branched alkyl groups having 1 to 6 carbon atoms, and the rest are hydrogen atoms.

[0558] (4)X1~X 20 At least four of them are independently straight-chain or branched alkyl groups having 1 to 6 carbon atoms, two of which have 3 to 6 carbon atoms and the remainder are hydrogen atoms.

[0559] Specific examples of compounds represented by general formula (30) are shown below. However, the compounds represented by general formula (30) in this invention are not limited to these specific examples.

[0560] [Chemistry 68]

[0561]

[0562] [Chemistry 69]

[0563]

[0564] [Chemistry 70]

[0565]

[0566] [Chemistry 71]

[0567]

[0568] Compounds represented by general formula (40)

[0569] In this embodiment, the first compound is preferably a compound represented by the following general formula (40).

[0570] [Chemistry 72]

[0571]

[0572] In general formula (40), R1 to R4 are each independently a hydrogen atom or a substituent, and R1 to R4 as substituents are each independently derived from...

[0573] Halogen atoms,

[0574] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0575] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0576] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and

[0577] Choose from the group consisting of heteroaryl groups with 5 to 30 substituted or unsubstituted cyclic atoms.

[0578] Specific examples of compounds represented by general formula (40) are shown below. However, the compounds represented by general formula (40) in this invention are not limited to these specific examples.

[0579] [Chemistry 73]

[0580]

[0581] [Chemistry 74]

[0582]

[0583] Compounds represented by general formula (50)

[0584] In this embodiment, the first compound is preferably a compound (aromatic amine derivative) represented by the following general formula (50).

[0585] [Chemistry 75]

[0586]

[0587] In general formula (50), A 1~A 2 Each of the following groups independently represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group with 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group with 1 to 10 carbon atoms, or a halogen atom, where p and q are integers from 1 to 5, and s are integers from 1 to 9. When p and q are 2 or more, multiple A groups... 1 A 2 They can be the same or different, and they can connect to form saturated or unsaturated cycles. However, there is no A. 1 And A 2 The case where both are hydrogen atoms.

[0588] R 1 This indicates a substituted or unsubstituted alkyl group with 3 to 10 carbon atoms, representing a secondary or tertiary alkyl group, where t is an integer from 1 to 9. In cases where t is greater than 2, multiple R... 1 They can be the same or different. R 2 This represents a hydrogen atom, an alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 20 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an aromatic amino group with 6 to 50 substituted or unsubstituted carbon atoms, an alkylamino group with 1 to 10 substituted or unsubstituted carbon atoms, or a halogen atom, where u is an integer from 0 to 8. When u is 2 or higher, multiple R... 2 They can be the same or different.

[0589] s+t+u is an integer from 2 to 10.

[0590] The compound represented by the general formula (50) is more preferably represented by the general formula (51) below.

[0591] [Chemistry 76]

[0592]

[0593] In general formula (51), A 1 A 2 p, q, R 1 and R 2 Each independently of A in the general formula (50) 1 A 2 p, q, R 1 and R 2 Synonyms.

[0594] Specific examples of compounds represented by general formula (50) are shown below. However, the compounds represented by general formula (50) in this invention are not limited to these specific examples.

[0595] [Chemistry 77]

[0596]

[0597] [Chemistry 78]

[0598]

[0599] [Chemistry 79]

[0600]

[0601] Compounds represented by general formula (I)

[0602] In this embodiment, the first compound is preferably a compound represented by the following general formula (I) (an aromatic amine derivative).

[0603] [Chemistry 80]

[0604]

[0605] In general formula (I), R represents a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylamino group with 6 to 50 substituted or unsubstituted carbon atoms, an alkylamino group with 1 to 20 substituted or unsubstituted carbon atoms, a cyano group, or a halogen atom. k is an integer from 1 to 9. When k is 2 or higher, multiple Rs can be the same or different from each other.

[0606] A 1 And A 2 Each of the following groups independently represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group with 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group with 1 to 20 carbon atoms, a cyano group, or a halogen atom. m and n are integers from 0 to 5. When m is 2 or more, multiple A groups... 1 They can be identical or different from each other, and they can also be connected to form saturated or unsaturated cycles. When n is 2 or more, multiple A's...2 They can be the same or different from each other, or they can be connected to form saturated or unsaturated rings.

[0607] Among them, A 1 And A 2 At least one of them has any one of the following groups: substituted or unsubstituted alkyl with 2 or more carbon atoms, substituted or unsubstituted aralkyl with 7 or more carbon atoms, substituted or unsubstituted cycloalkyl with 3 or more carbon atoms, substituted or unsubstituted alkoxy with 2 or more carbon atoms, and substituted or unsubstituted alkylamino with 2 or more carbon atoms.

[0608] For any integer p between 1 and 9, when p is 2 or greater, multiple () p The groups within can be the same or different from each other. (k+p is an integer less than 10.)

[0609] The compound represented by the general formula (I) is more preferably a compound represented by the general formula (II) below.

[0610] [Chemistry 81]

[0611]

[0612] In general formula (II), R represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a cyano group, or a halogen atom. k is an integer from 1 to 9. When k is 2 or higher, multiple Rs can be the same or different from each other.

[0613] A 1 And A 2 Each of the following groups independently represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group with 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group with 1 to 20 carbon atoms, a cyano group, or a halogen atom. m and n are integers from 0 to 5. When m is 2 or more, multiple A groups... 1 They can be identical or different from each other, and they can also be connected to form saturated or unsaturated cycles. When n is 2 or more, multiple A's... 2They can be the same or different from each other, or they can be connected to form saturated or unsaturated rings.

[0614] Among them, A 1 And A 2 At least one of them has any one of the following groups: substituted or unsubstituted alkyl with 2 or more carbon atoms, substituted or unsubstituted aralkyl with 7 or more carbon atoms, substituted or unsubstituted cycloalkyl with 3 or more carbon atoms, substituted or unsubstituted alkoxy with 2 or more carbon atoms, and substituted or unsubstituted alkylamino with 2 or more carbon atoms.

[0615] Multiple groups within ()2 can be the same or different from each other.

[0616] Specific examples of compounds represented by general formula (I) are shown below. However, the compounds represented by general formula (I) in this invention are not limited to these specific examples.

[0617] [Chemistry 82]

[0618]

[0619] [Chemistry 83]

[0620]

[0621] Compounds represented by general formula (60)

[0622] In this embodiment, the first compound is preferably a compound represented by the following general formula (60).

[0623] [Chemistry 84]

[0624]

[0625] In the general formula (60),

[0626] The Za ring, Zb ring, and Zc ring are each independently derived from...

[0627] Substituted or unsubstituted aromatic rings with 6 to 30 carbon atoms, and

[0628] Heteroaromatic rings with 5 to 30 cyclic atoms, substituted or unsubstituted

[0629] The selected ring structure in the group.

[0630] X 21 and X 22 Each can be independently an oxygen atom, NRa (a nitrogen atom with the substituent Ra), or a sulfur atom.

[0631] In X 21In the case of NRa, Ra may bond with a Za ring or a Zb ring to form a ring, or it may not form a ring.

[0632] In X 22 In the case of NRa, Ra may bond with a Za ring or a Zc ring to form a ring, or may not form a ring.

[0633] Ra is independently derived from

[0634] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0635] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, and

[0636] Alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted

[0637] The groups selected from the group that constitute the composition,

[0638] Y 21 It is any one of boron atom, phosphorus atom, SiRb (silicon atom with substituent Rb), P=O, and P=S.

[0639] Rb is independently derived from

[0640] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0641] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, and

[0642] Alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted

[0643] The groups selected from the group that constitutes the composition.

[0644] Specific examples of compounds represented by general formula (60) are shown below. However, the compounds represented by general formula (60) in this invention are not limited to these specific examples.

[0645] [Chemistry 85]

[0646]

[0647] [Chemistry 86]

[0648]

[0649] Method for manufacturing the first compound

[0650] The first compound can be manufactured using known methods.

[0651] (Second compound)

[0652] The second compound is a delayed fluorescence compound.

[0653] The second compound is not a phosphorescent metal complex. Preferably, the second compound is not a metal complex.

[0654] Delayed fluorescence

[0655] Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). This literature states that if the energy difference ΔE between the excited singlet and excited triplet states of a fluorescent material can be reduced... 13 In this case, the reverse energy transfer from the excited triplet state with low migration probability to the excited singlet state usually occurs efficiently, producing thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is illustrated in Figure 10.38 of this document. The first compound in this embodiment is preferably a compound that demonstrates thermally activated delayed fluorescence generated by such a mechanism.

[0656] Typically, delayed fluorescence can be confirmed by transition PL (Photo Luminescence) measurements.

[0657] Furthermore, the behavior of delayed fluorescence can be analyzed based on the decay curve obtained from transition PL measurements. Transition PL measurement refers to the method of irradiating the sample with a pulsed laser to excite it, and measuring the decay behavior (transition characteristics) of PL emission after irradiation stops. PL emission in TADF materials consists of two components: the emission component from singlet excitons generated by the initial PL excitation and the emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after pulsed laser irradiation.

[0658] On the other hand, delayed fluorescence originates from the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays gradually. Consequently, there is a significant time difference between the emission of singlet excitons generated from the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[0659] Figure 2 The diagram shows a schematic of an example apparatus for measuring transient PL. Figure 2 The method for measuring transition PL and an example of analyzing the behavior of delayed fluorescence are explained.

[0660] Figure 2The transition PL measurement device 100 includes: a pulsed laser unit 101 for irradiating light of a specified wavelength; a sample chamber 102 for housing the measurement sample; a beam splitter 103 for splitting the light emitted from the measurement sample; a streak camera 104 for imaging a two-dimensional image; and a personal computer 105 for reading and analyzing the two-dimensional image. Furthermore, the measurement of transition PL is not limited to... Figure 2 The device described.

[0661] The sample housed in the sample chamber 102 can be obtained by forming a thin film on a quartz substrate by doping the matrix material with a dopant material at a concentration of 12% by mass.

[0662] For the thin film sample housed in the sample chamber 102, a pulsed laser is irradiated from the pulsed laser unit 101 to excite the doped material. The emitted light is extracted in a direction 90 degrees relative to the irradiation direction of the excitation light, and the extracted light is split by the beam splitter 103 to form a two-dimensional image in the streak camera 104. The result is a two-dimensional image with the vertical axis corresponding to time, the horizontal axis corresponding to wavelength, and the bright spots corresponding to emission intensity. If this two-dimensional image is cut along a specified time axis, an emission spectrum with emission intensity as the vertical axis and wavelength as the horizontal axis can be obtained. Furthermore, if this two-dimensional image is cut along the wavelength axis, a decay curve (transition pulse) with the logarithm of emission intensity as the vertical axis and time as the horizontal axis can be obtained.

[0663] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the dopant material, thin film sample A was prepared as described above, and transition PL measurements were performed.

[0664] [Chemistry 87]

[0665]

[0666] Here, the decay curves were analyzed using thin film sample A and thin film sample B. Thin film sample B was prepared using the reference compound H2 as the matrix material and the reference compound D1 as the dopant material, as described above.

[0667] Figure 3 The attenuation curves obtained from the transition PL measured on thin film sample A and thin film sample B are shown in the figure.

[0668] [Chemistry 88]

[0669]

[0670] As described above, by measuring the transition PL (luminescence intensity), a luminescence decay curve can be obtained with luminescence intensity as the vertical axis and time as the horizontal axis. Based on this luminescence decay curve, the fluorescence intensity ratio of fluorescence emitted from a singlet excited state generated by photoexcitation to delayed fluorescence emitted from a singlet excited state generated via reverse energy transfer from a triplet excited state can be calculated. In materials with delayed fluorescence, the proportion of slowly decaying delayed fluorescence intensity is relatively large compared to the intensity of rapidly decaying fluorescence.

[0671] Specifically, luminescence from delayed-fluorescence materials can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence observed immediately from the excited state after being excited by a pulse of light (light from a pulsed laser) of a wavelength absorbed by the delayed-fluorescence material. Delay luminescence refers to luminescence that is not immediately observed after the pulse of light excitation but is observed later.

[0672] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0673] Furthermore, in this specification, a sample prepared by the method described below is used for measuring the delayed fluorescence of the first compound. For example, the first compound is dissolved in toluene, and a dilute solution with an absorbance of less than 0.05 at the excitation wavelength is prepared to eliminate the effect of self-absorption. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[0674] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al., J. Phys. Chem., 80(1976)969.

[0675] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0676] In this embodiment, the amount of prompt emission (instantaneous emission) of the target compound (first compound) is denoted as X. P The amount of delayed emission is denoted as X. D At that time, X D / X P The value is preferably 0.05 or higher.

[0677] The measurement of the amount and ratio of Prompt luminescence and Delay luminescence of compounds other than the first compound in this specification is the same as the measurement of the amount and ratio of Prompt luminescence and Delay luminescence of the first compound.

[0678] In this embodiment, the second compound may be exemplified by a compound represented by the following general formula (2).

[0679] [Chemistry 89]

[0680]

[0681] In the general formula (2),

[0682] A is the acceptor (electron-accepting) site, a group having a local structure selected from the following general formulas (a-1) to (a-7). When multiple A's are present, they may be identical or different from each other, and A's can bond together to form saturated or unsaturated rings.

[0683] B is a donor (electron-donating) site, possessing a local structure selected from the following general formulas (b-1) to (b-6). When multiple Bs are present, they may be identical or different from each other, and Bs can bond together to form saturated or unsaturated rings.

[0684] a, b, and d can be independently 1, 2, 3, 4, or 5.

[0685] c can be 0, 1, 2, 3, 4, or 5.

[0686] When c is 0, A and B are bonded by single bonds or spiral bonds.

[0687] When c is 1, 2, 3, 4, or 5, L is from

[0688] Substituted or unsubstituted aromatic hydrocarbon groups with 6 to 30 carbon atoms, and

[0689] The linking group selected from the group consisting of substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, in the case of multiple L groups, the multiple L groups may be the same or different from each other, and the L groups may bond with each other to form saturated or unsaturated rings.

[0690] [Chemistry 90]

[0691]

[0692] [Chemistry 91]

[0693]

[0694] In the general formulas (b-1) to (b-6),

[0695] R can be either a hydrogen atom or a substituent, and when R is a substituent, the substituent can be...

[0696] Substituted or unsubstituted aromatic hydrocarbon groups with 6 to 30 carbon atoms in the ring;

[0697] Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, and

[0698] The group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, wherein, in the presence of multiple Rs, the multiple Rs are the same or different from each other, and the Rs can bond to each other to form saturated or unsaturated rings.

[0699] As an example of the bonding states of a compound represented by the general formula (2), the bonding states shown in Table 1 below can be cited as an example.

[0700] Table 1

[0701]

[0702] In this embodiment, the second compound preferably has a local structure represented by the following general formula (200) and a local structure represented by the following general formula (2Y) in one molecule.

[0703] [Chemistry 92]

[0704]

[0705] In the general formula (200), CN is a cyano group.

[0706] n is an integer greater than or equal to 1. Preferably, n is an integer greater than or equal to 1 and less than 5, and more preferably an integer greater than or equal to 2 and less than 4.

[0707] Z1 through Z6 are each independently a nitrogen atom, a carbon atom bonded to CN, or a carbon atom bonded to other atoms in the molecule of the second compound. For example, if Z1 is a carbon atom bonded to CN, at least one of the remaining five (Z2 through Z6) is a carbon atom bonded to other atoms in the molecule of the second compound. This other atom may be an atom constituting a local structure represented by the following general formula (2Y), or it may be an atom constituting a linking group or substituent between these local structures.

[0708] The second compound of this embodiment may have a 6-membered ring composed of Z1 to Z6 as a local structure, or it may have a fused ring formed by further fused rings on the 6-membered ring as a local structure.

[0709] [Chemistry 93]

[0710]

[0711] In the general formula (2Y), F and G independently represent the ring structure.

[0712] m can be 0 or 1.

[0713] When m is 1, Y 20 It represents a single bond, oxygen atom, sulfur atom, selenium atom, carbon atom, silicon atom, or germanium atom.

[0714] When m is 0 in the general formula (2Y), the general formula (2Y) is represented by the following general formula (20Y).

[0715] [Chemistry 94]

[0716]

[0717] The ring structure F and ring structure G in the general formula (20Y) are synonyms with the ring structure F and ring structure G in the general formula (2Y).

[0718] Furthermore, when m is 1 in the general formula (2Y), the general formula (2Y) is represented by any one of the following general formulas (22) to (28).

[0719] [Chem. 95]

[0720]

[0721] The ring structure F and ring structure G in general formulas (22) to (28) are synonyms with the ring structure F and ring structure G in general formula (2Y).

[0722] In this embodiment, the ring structure F and the ring structure G are preferably 5-membered rings or 6-membered rings, and the 5-membered rings or 6-membered rings are preferably unsaturated rings, more preferably unsaturated 6-membered rings.

[0723] The second compound in this embodiment is preferably a compound represented by the following general formula (20).

[0724] [Chemistry 96]

[0725]

[0726] In the general formula (20),

[0727] A is represented by the general formula (200), wherein, in the general formula (200), CN is a cyano group, n is an integer greater than or equal to 1, and Z1 to Z6 are independently a nitrogen atom, a carbon atom bonded to CN, a carbon atom bonded to R, a carbon atom bonded to L, or a carbon atom bonded to D, respectively, and among Z1 to Z6, at least one carbon atom is bonded to CN, and at least one carbon atom is bonded to L or D.

[0728] Each R is independently a hydrogen atom or a substituent, wherein the substituent in R is selected from the group consisting of: halogen atom, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 cyclic carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 cyclic carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 cyclic carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 cyclic carbon atoms, substituted or unsubstituted alkylamino group having 2 to 30 cyclic carbon atoms, substituted or unsubstituted arylamino group having 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 cyclic carbon atoms, and substituted or unsubstituted arylthio group having 6 to 30 cyclic carbon atoms.

[0729] In the general formula (20), D is represented by the general formula (2Y), wherein the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have substituents, and m is 0 or 1. When m is 1, Y 20 Represents single bonds, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, and CR. 21 R 22 SiR 23 R 24 Or GeR 25 R 26 R 21 ~R 26Synonymous with the group exemplified by R. Furthermore, when m is 1 in the general formula (2Y), the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the following general formulas (21Y) to (24Y).

[0730] [Chemistry 97]

[0731]

[0732] In the general formula (20),

[0733] (i) When L is between A and D

[0734] L is a single bond, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms in the ring, or a substituted or unsubstituted aromatic heterocyclic group with 5 to 14 cyclic atoms; CR 81 R 82 NR 83 O, S, SiR 84 R 85 CR 86 R 87 -CR 88 R 89 CR 90 =CR 91 Substituted or unsubstituted aliphatic hydrocarbon cyclic groups, or substituted or unsubstituted aliphatic heterocyclic groups,

[0735] The R 81 ~R 91 Each is independently synonymous with the aforementioned R.

[0736] In the general formula (20),

[0737] (ii) In the case that L is located at the end of the molecule of the second compound,

[0738] L is synonymous with R.

[0739] In the general formula (20),

[0740] f is an integer greater than or equal to 1.

[0741] e and g are each an independent integer greater than or equal to 0.

[0742] Multiple A's can be the same or different from each other.

[0743] Multiple Ds can be the same or different from each other.

[0744] Multiple L's can be the same or different from each other.

[0745] The general formula (20) is represented, for example, by the following general formulas (201) to (220).

[0746] Table 2

[0747]

[0748] Table 3

[0749]

[0750] Table 4

[0751]

[0752] Table 5

[0753]

[0754] Furthermore, in the general formula (20), in the repeating units within the brackets having a repetition number of f, D can be bonded to A via L, or A can be bonded to D via L. For example, the chain can also be split as in the following general formulas (221) to (228).

[0755] [Chem. 98]

[0756]

[0757] The second compound in this embodiment is not limited to compounds represented by the general formulas (201) to (228). In addition, when L is omitted in the general formulas (201) to (228), L represents a single bond between A and D, or L represents a hydrogen atom located at the end of the molecule of the second compound.

[0758] To keep the ΔST of a molecule small, L is preferably not a fused aromatic ring in the molecular design, but a fused aromatic ring can be used within the range where thermally active delayed fluorescence emission can be obtained. Furthermore, because the molecular design of A and D must be correctly arranged in a molecule, the second compound of this embodiment is preferably a low molecular weight material. Therefore, the second compound of this embodiment is preferably a molecular weight of 5000 or less, more preferably 3000 or less. The second compound of this embodiment preferably contains a partial structure of the general formula (200) and the general formula (2Y).

[0759] Organic EL elements containing the second compound emit light using a thermally active delayed fluorescence mechanism.

[0760] In this embodiment, the general formula (2Y) is preferably represented by at least one of the following general formulas (2a) and (2x).

[0761] [Chemistry 99]

[0762]

[0763] [Chemistry 100]

[0764]

[0765] In the general formula (2x), A and B independently represent either a ring structure represented by general formula (2c) or a ring structure represented by general formula (2d), where ring structure A and ring structure B are fused with adjacent ring structures at any position. px and py are each an integer between 0 and 4, representing the number of ring structures A and ring structures B, respectively. When px is an integer between 2 and 4, multiple ring structures A can be the same or different from each other. When py is an integer between 2 and 4, multiple ring structures B can be the same or different from each other. Therefore, for example, when px is 2, ring structure A can be two ring structures represented by general formula (2c), two ring structures represented by general formula (2d), or a combination of one ring structure represented by general formula (2c) and one ring structure represented by general formula (2d).

[0766] [Chemistry 101]

[0767]

[0768] [Chemistry 102]

[0769]

[0770] In the general formula (2d), Z7 represents a carbon atom, a nitrogen atom, a sulfur atom, or an oxygen atom.

[0771] In the general formula (2x), when px is 0 and py is c, it is represented by the following general formula (2b).

[0772] [Chemistry 103]

[0773]

[0774] In the general formula (2b), c is an integer between 1 and 4. When c is an integer between 2 and 4, the multiple ring structures E can be the same or different from each other. In the general formula (2b), E represents a ring structure represented by the general formula (2c) or a ring structure represented by the general formula (2d), and the ring structure E is fused with the adjacent ring structure at any position. Therefore, for example, when c is 2, the two ring structures E can be two ring structures represented by the general formula (2c), two ring structures represented by the general formula (2d), or a combination of one ring structure represented by the general formula (2c) and one ring structure represented by the general formula (2d).

[0775] By simultaneously retaining the local structures of the general formula (200) and the general formula (2Y) in a molecule, △ST can be effectively designed to be small.

[0776] The second compound of this embodiment is preferably a structure in its molecule represented by the following general formula (2e).

[0777] [Chemistry 104]

[0778]

[0779] In the general formula (2e), R1 to R9 are each independently a hydrogen atom, a substituent, or a single bond bonded to other atoms in the molecule of the second compound.

[0780] The substituents in R1 to R9 are selected from the group consisting of: halogen atoms, substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted aromatic heterocyclic groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted alkylamino groups with 2 to 30 cyclic carbon atoms, substituted or unsubstituted arylamino groups with 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 cyclic carbon atoms, and substituted or unsubstituted arylthio groups with 6 to 30 cyclic carbon atoms. In this compound, at least one of R1 to R9 is a single bond bonded to other atoms in the molecule of the second compound.

[0781] In the general formula (2e), at least one group of the combinations of substituents selected from R1 to R9 can bond to each other to form a ring structure. This ring structure formation means that, in the general formula (2e), the substituents selected from R1 to R8 (bonded to adjacent carbon atoms in a 6-membered ring) and R9 (bonded to the nitrogen atom in a 5-membered ring), respectively, can form a ring structure with each other. Specifically, in the general formula (2e), at least one group of the combinations of substituents consisting of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, and R9 and R1 can bond to each other to form a ring structure.

[0782] In this embodiment, the ring structure formed by the bonding of substituents to each other is preferably a fused ring. For example, the case of forming such a ring structure in the general formula (2e) is considered to be the case of forming a fused 6-membered ring structure.

[0783] Furthermore, the second compound of this embodiment is preferably a structure in its molecule represented by the following general formula (2y).

[0784] [Chemistry 105]

[0785]

[0786] R in the general formula (2y) 11 ~R 19 Each of these is independently synonymous with R1 to R9 in the general formula (2e). Wherein, R... 11 ~R 19 At least one of them is a single bond bonded to other atoms in the molecule of the second compound. In the general formula (2y), from R 11 ~R 19 At least one combination of the selected substituents can bond together to form a ring structure. In the general formula (2y), A and B independently represent a ring structure represented by the following general formula (2g) or a ring structure represented by the following general formula (2h), and ring structures A and B are fused with adjacent ring structures at any position. px is the number of ring structures A, which is an integer from 0 to 4. When px is an integer from 2 to 4, multiple ring structures A can be the same or different from each other. When py is an integer from 2 to 4, multiple ring structures B can be the same or different from each other. py is the number of ring structures B, which is an integer from 0 to 4. Therefore, for example, when px is 2, two ring structures A can be two ring structures represented by the following general formula (2g), two ring structures represented by the following general formula (2h), or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the following general formula (2h).

[0787] [Chemistry 106]

[0788]

[0789] [Chemistry 107]

[0790]

[0791] In the general formula (2g), R 201 and R 202 Each of these is independently synonymous with R1 to R9, R 201 and R 202 They can bond together to form a ring structure. R 201 and R 202 They are respectively bonded to the carbon atoms of the 6-membered ring forming the general formula (2g).

[0792] In the general formula (2h), Z8 represents CR203 R 204 NR 205 sulfur atoms or oxygen atoms, R 203 ~R 205 Each of the substituents in R1 to R9 is independently synonymous with the substituent in R9.

[0793] In the general formula (2y), from R 11 ~R 19 R 201 ~R 205 At least one of the selected substituents can bond with each other to form a ring structure.

[0794] In the general formula (2y), when px is 0 and py is c, it is represented by the following general formula (2f).

[0795] [Chemistry 108]

[0796]

[0797] R in the general formula (2f) 11 ~R 19 Each of these is independently synonymous with R1 to R9 in the general formula (2e). Wherein, R... 11 ~R 19 At least one of them is a single bond bonded to other atoms in the molecule of the second compound. In the general formula (2f), from R 11 ~R 19 At least one combination of the selected substituents can bond together to form a ring structure. In the general formula (2f), E represents a ring structure represented by the general formula (2g) or a ring structure represented by the general formula (2h), which is fused with adjacent ring structures at any position. c is the number of ring structures E, which is an integer from 1 to 4. When c is an integer from 2 to 4, the multiple ring structures E can be the same or different from each other. Therefore, for example, when c is 2, the two ring structures E can be two ring structures represented by the general formula (2g), two ring structures represented by the general formula (2h), or a combination of one ring structure represented by the general formula (2g) and one ring structure represented by the general formula (2h).

[0798] The second compound in this embodiment is preferably represented by the following general formula (2A).

[0799] [Chemistry 109]

[0800]

[0801] In the general formula (2A), n is an integer greater than or equal to 1, t is an integer greater than or equal to 1, and u is an integer greater than or equal to 0.A The ring is an aromatic hydrocarbon ring with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocycle with 6 to 30 cyclic atoms. CN is a cyano group. D1 and D2 are each independently represented by the general formula (2Y), wherein the ring structure F and ring structure G in the general formula (2Y) can be unsubstituted or have substituents, m is 0 or 1, and when m is 1, Y 20 Represents single bonds, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, and CR. 21 R 22 SiR 23 R 24 Or GeR 25 R 26 R 21 ~R 26 Synonymous with R. Furthermore, when m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the general formulas (21Y) to (24Y). D1 and D2 can be the same or different. When t is 2 or more, multiple D1s can be the same or different from each other. When u is 2 or more, multiple D2s can be the same or different from each other.

[0802] In this embodiment, the L A Preferably, it is an aromatic hydrocarbon ring with 6 to 14 carbon atoms, whether substituted or unsubstituted. Examples of aromatic hydrocarbon rings with 6 to 14 carbon atoms include benzene, naphthalene, fluorene, and phenanthrene. The L... A Further preferred are aromatic hydrocarbon rings with 6 to 10 carbon atoms.

[0803] Furthermore, as the L A Aromatic heterocycles with 6 to 30 cyclic atoms, such as pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthrene, benzofuran, and dibenzofuran.

[0804] In this embodiment, it is also possible that, in the general formula (2A), when forming L A The aromatic hydrocarbon ring represents a structure where D1 or D2 is bonded to the first carbon atom, and CN is bonded to the second carbon atom adjacent to the first carbon atom. For example, in the second compound of this embodiment, as shown in the partial structure represented by the following general formula (2B), D is bonded to the first carbon atom C1, and a cyano group is bonded to the second carbon atom C2 adjacent to the first carbon atom C1. In the following general formula (2B), D is synonymous with D1 or D2. In the following general formula (2B), the wavy line indicates the site of bonding with other structures or atoms.

[0805] [Chemical 110]

[0806]

[0807] By bonding D1 or D2 having a structure like that of general formula (2a) or general formula (2b) adjacent to a cyano group to the L group... A The aromatic hydrocarbon rings represented can reduce the ΔST value of the compound.

[0808] In this embodiment, t is preferably an integer of 2 or more. When L... A When there are two or more D1s bonded to the aromatic hydrocarbon ring, the multiple D1s can be of the same structure or different structures.

[0809] The second compound in this embodiment is preferably represented by the following general formula (21).

[0810] [Chemistry 111]

[0811]

[0812] In the general formula (21), A 21 And B 21 Each can be independently represented as a substituted or unsubstituted aromatic hydrocarbon group with 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 5 to 30 carbon atoms.

[0813] X 21 ~X 28 and Y 21 ~Y 28 Each independently represents a nitrogen atom, and R D Bonded carbon atoms or with L 23 Bonded carbon atoms. Among them, X 25 ~X 28 At least one of them is with L 23 Bonded carbon atoms, Y 21 ~Y 24 At least one of them is with L 23 Bonded carbon atoms.

[0814] R D Each R can be an independent hydrogen atom or a substituent. D The substituents are selected from the group consisting of: halogen atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 5 to 30 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted silyl groups.

[0815] L 21 and L 22 Each is an independent single bond or linking group, as L 21and L 22 The linking group is: an aromatic hydrocarbon group with 6 to 30 cyclic carbons that are substituted or unsubstituted; a heterocyclic group with 5 to 30 cyclic atoms that are substituted or unsubstituted; a multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group; a multiple linking group formed by bonding 2 to 4 groups selected from the heterocyclic group; or a multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group.

[0816] L 23 It indicates a monocyclic hydrocarbon group with 6 or fewer cyclic carbon atoms, whether substituted or unsubstituted, or a monocyclic heterocyclic group with 6 or fewer cyclic atoms, whether substituted or unsubstituted.

[0817] w represents an integer from 0 to 3. When w is 0, X 25 ~X 28 At least one of them is related to Y 21 ~Y 24 At least one of them is directly bonded.

[0818] In addition, monocyclic hydrocarbon groups are not fused rings, but groups derived from a single hydrocarbon ring (aliphatic cyclic hydrocarbons or aromatic hydrocarbons), while monocyclic heterocyclic groups are groups derived from a single heterocycle.

[0819] Furthermore, in the general formula (21), at least one of the following conditions (i) and (ii) must be satisfied.

[0820] (i)A 21 And B 21 At least one of them is an aromatic hydrocarbon group with 6 to 30 cyclic carbons obtained by substituted cyano, or an aromatic heterocyclic group with 6 to 30 cyclic atoms obtained by substituted cyano.

[0821] (ii)X 21 ~X 24 and Y 25 ~Y 28 At least one of them is related to R D The bonded carbon atom, the R D At least one of them is an aromatic hydrocarbon group with 6 to 30 cyclic carbons obtained by substituted cyano, or an aromatic heterocyclic group with 6 to 30 cyclic atoms obtained by substituted cyano.

[0822] Among them, there are multiple R D In the case of multiple R D They can be the same or different.

[0823] In the general formula (21), when A is used 21 And B 21When the aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 6 to 30 carbon atoms has a substituent, the substituent is preferably one or more groups selected from the group consisting of a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, and a heterocyclic group having 5 to 30 carbon atoms. In the case of A... 21 And B 21 When there are multiple substituents, the substituents can be the same or different from each other.

[0824] Preferably, in the general formula (21), the condition (i) is satisfied but the condition (ii) is not satisfied.

[0825] Alternatively, in the general formula (21), the condition of (ii) is satisfied but the condition of (i) is not satisfied.

[0826] Furthermore, it is preferable to satisfy the conditions in (i) and (ii).

[0827] In the general formula (21), A is preferred. 21 And B 21 At least one of them is,

[0828] Phenyl groups obtained by cyano substitution

[0829] Naphthyl groups obtained by cyano substitution

[0830] phenanthrene obtained by cyano substitution,

[0831] Dibenzofuranyl, obtained by cyano substitution

[0832] dibenzothiophene group obtained by cyano substitution,

[0833] Biphenyl obtained by cyano substitution,

[0834] Triphenyl groups obtained by cyano substitution

[0835] 9,9-diphenylfluorenyl, obtained by cyano substitution,

[0836] 9,9'-spirobis[9H-fluorene]-2-yl obtained by cyano substitution,

[0837] 9,9-dimethylfluorenyl obtained by substitution with cyano, or

[0838] Triphenylene oxide obtained by substituted cyano group.

[0839] In the general formula (21), preferably, X 21 ~X 24 and Y 25 ~Y 28 At least one of them is CR D X 21 ~X 24 and Y 25 ~Y 28 R in D At least one of them is,

[0840] Phenyl groups obtained by cyano substitution

[0841] Naphthyl groups obtained by cyano substitution

[0842] phenanthrene obtained by cyano substitution,

[0843] Dibenzofuranyl, obtained by cyano substitution

[0844] dibenzothiophene group obtained by cyano substitution,

[0845] Biphenyl obtained by cyano substitution,

[0846] Triphenyl groups obtained by cyano substitution

[0847] 9,9-diphenylfluorenyl, obtained by cyano substitution,

[0848] 9,9'-spirobis[9H-fluorene]-2-yl obtained by cyano substitution,

[0849] 9,9-dimethylfluorenyl obtained by substitution with cyano, or

[0850] Triphenylene oxide obtained by substituted cyano group.

[0851] In the general formula (21), X is preferred. 26 With Y 23 via L 23 Bonding or direct bonding.

[0852] Furthermore, in the general formula (21), X is preferred. 26 With Y 22 via L 23 Bonding or direct bonding.

[0853] Furthermore, in the general formula (21), X is preferred. 27 With Y 23 via L 23 Bonding or direct bonding.

[0854] In the general formula (21), w is preferably 0.

[0855] Furthermore, in the general formula (21), w is preferably 1.

[0856] In the general formula (21), L is preferred. 21 and L 22 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms that is either a single bond, substituted or unsubstituted.

[0857] Specific examples of the second compound are shown below. However, the second compound in this invention is not limited to these examples.

[0858] [Chemistry 112]

[0859]

[0860] [Chemistry 113]

[0861]

[0862] [Chemistry 114]

[0863]

[0864] [Chemistry 115]

[0865]

[0866] [Chemistry 116]

[0867]

[0868] [Chemistry 117]

[0869]

[0870] [Chemistry 118]

[0871]

[0872] [Chemistry 119]

[0873]

[0874] [Chemistry 120]

[0875]

[0876] Method for manufacturing the second compound

[0877] The second compound can be manufactured, for example, by the methods described in International Publication No. 2013 / 180241, International Publication No. 2014 / 092083 and International Publication No. 2014 / 104346.

[0878] (Third compound)

[0879] The third compound can be a compound that exhibits thermally activated delayed fluorescence or a compound that does not exhibit thermally activated delayed fluorescence.

[0880] While not particularly limited, the third compound is preferably a compound other than an amine compound. Furthermore, for example, a derivative selected from the group consisting of carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives can be used as the third compound, but it is not limited to these derivatives.

[0881] The third compound is also preferably a compound in which at least one of the following general formula (31), general formula (32), general formula (33A) and general formula (34A) is contained in one molecule.

[0882] [Chemistry 121]

[0883]

[0884] In the general formula (31),

[0885] Y 31 ~Y 36 Each carbon atom is either a nitrogen atom or bonded to other atoms in the molecule of the third compound.

[0886] Among them, Y 31 ~Y 36 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound.

[0887] In the general formula (32),

[0888] Y 41 ~Y 48 Each carbon atom is either a nitrogen atom or bonded to other atoms in the molecule of the third compound.

[0889] Among them, Y 41 ~Y 48 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound.

[0890] X 30 Nitrogen, oxygen, or sulfur atoms that are bonded to other atoms in the molecule of the third compound.

[0891] In the general formulas (33A) and (34A), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[0892] In the general formula (32), Y is also preferred.41 ~Y 48 At least two of them are carbon atoms bonded to other atoms in the molecule of the third compound, forming a ring structure containing the carbon atoms.

[0893] For example, the preferred local structure represented by the general formula (32) is any one of the local structures selected from the group consisting of local structures represented by the following general formulas (321), (322), (323), (324), (325) and (326).

[0894] [Chemistry 122]

[0895]

[0896] [Chemistry 123]

[0897]

[0898] [Chemistry 124]

[0899]

[0900] In the general formulas (321) to (326),

[0901] X 30 Each of the nitrogen, oxygen, or sulfur atoms is independently bonded to other atoms in the molecule of the third compound.

[0902] Y 41 ~Y 48 Each carbon atom is either a nitrogen atom or bonded to other atoms in the molecule of the third compound.

[0903] X 31 Each of the following is an independent nitrogen atom, oxygen atom, sulfur atom, or carbon atom bonded to other atoms in the molecule of the third compound.

[0904] Y 61 ~Y 64 Carbon atoms that are either nitrogen atoms or carbon atoms bonded independently to other atoms in the molecule of a third compound.

[0905] In this embodiment, the third compound preferably has a local structure represented by general formula (323) in general formulas (321) to (326).

[0906] The local structure represented by the general formula (31) is preferably included in the third compound as at least any one of the groups selected from the group represented by the general formula (33) and the group represented by the general formula (34).

[0907] The third compound is also preferably having at least one of the local structures represented by the following general formulas (33) and (34). As shown in the local structures represented by the following general formulas (33) and (34), the bonding sites are located at meta positions, thus enabling the third compound to achieve a band gap T at 77 [K]. 77K (M2) remained high.

[0908] [Chemistry 125]

[0909]

[0910] In the general formula (33), Y 31 Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[0911] In the general formula (34), Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[0912] In the general formulas (33) and (34),

[0913] R 31 Each can be an independent hydrogen atom or a substituent.

[0914] R as a substituent 31 Independently from

[0915] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0916] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0917] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0918] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[0919] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0920] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[0921] Substituted or unsubstituted silyl groups

[0922] Replacement of germanium-based

[0923] Substituted phosphine oxide group,

[0924] Halogen atoms,

[0925] cyano,

[0926] Nitro, and

[0927] Substituted or unsubstituted carboxyl groups

[0928] Choose from the groups that make up the group.

[0929] Wherein, the R 31 The aryl group in the substituted or unsubstituted cyclic group has a carbon number of 6 to 30, preferably a non-fused ring.

[0930] In the general formulas (33) and (34), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[0931] In the general formula (33), Y is preferred. 31 Y 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[0932] Furthermore, in the general formula (34), Y is preferred. 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[0933] The preferred substituted germanium-based form is -Ge(R) 301 )3 indicates. R 301 Each is an independent substituent. Substituent R 301 Preferably, it is an alkyl group with 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted. Multiple R 301 They are the same or different from each other.

[0934] The local structure represented by the general formula (32) is preferably included in the third compound as at least one group selected from the group composed of the groups represented by the following general formulas (35) to (39) and the following general formula (30a).

[0935] [Chemistry 126]

[0936]

[0937] [Chemistry 127]

[0938]

[0939] [Chemistry 128]

[0940]

[0941] In the general formula (35), Y 41 ~Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0942] In the general formulas (36) and (37), Y 41 ~Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0943] In the general formula (38), Y 41 Y 42 Y 44 Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0944] In the general formula (39), Y 42 ~Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0945] In the general formula (30a), Y 42 ~Y 47 Each independently consists of a nitrogen atom or CR 32 .

[0946] In the general formulas (35) to (39) and (30a),

[0947] R 32 Each can be an independent hydrogen atom or a substituent.

[0948] R as a substituent 32 from

[0949] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0950] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0951] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0952] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[0953] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0954] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[0955] Substituted or unsubstituted silyl groups

[0956] Replacement of germanium-based

[0957] Substituted phosphine oxide group,

[0958] Halogen atoms,

[0959] cyano,

[0960] Nitro, and

[0961] Substituted or unsubstituted carboxyl groups

[0962] Choose from the groups that make up the group.

[0963] Multiple R 32 They are the same or different from each other.

[0964] In the general formulas (37) to (39) and (30a),

[0965] X 30 For NR 33 oxygen or sulfur atoms

[0966] R 33 from

[0967] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0968] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0969] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0970] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[0971] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0972] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[0973] Substituted or unsubstituted silyl groups

[0974] Replacement of germanium-based

[0975] Substituted phosphine oxide group,

[0976] Fluorine atom,

[0977] cyano,

[0978] Nitro, and

[0979] Substituted or unsubstituted carboxyl groups

[0980] Choose from the groups that make up the group.

[0981] Multiple R 33 They are the same or different from each other.

[0982] Wherein, the R 33 The aryl group in the substituted or unsubstituted cyclic group has a carbon number of 6 to 30, preferably a non-fused ring.

[0983] In the general formulas (35) to (39) and general formula (30a), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[0984] In the general formula (35), Y is preferred. 41 ~Y 48 CR independently 32 In the general formulas (36) and (37), Y is preferred. 41 ~Y 45 Y 47 and Y 48 CR independently 32 In the general formula (38), Y is preferred. 41 Y 42 Y 44 Y 45 Y 47 and Y 48 CR independently 32 In the general formula (39), Y is preferred. 42 ~Y 48 CR independently 32 In the general formula (30a), Y is preferred. 42 ~Y 47 CR independently 32 Multiple R 32 They are the same or different from each other.

[0985] In the third compound, X 30 Preferably, it contains oxygen atoms or sulfur atoms, and more preferably oxygen atoms.

[0986] In the third compound, R is preferred. 31 and R 32 R can be either a hydrogen atom or a substituent, and can be a substituent. 31 and R as a substituent 32 Each group is independently selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms. More preferably, R. 31 and R32 It consists of a hydrogen atom, a cyano group, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 5 to 30 substituted or unsubstituted cyclic atoms. Specifically, R, as a substituent... 31 and R as a substituent 32 When the aryl group is a substituted or unsubstituted cyclic carbon group with a carbon number of 6 to 30, the aryl group is preferably a non-fused ring.

[0987] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound. Furthermore, the third compound preferably does not have a fused aromatic hydrocarbon ring in its molecule.

[0988] Method for manufacturing the third compound

[0989] The third compound can be manufactured by methods described, for example, in International Publication Nos. 2012 / 153780 and 2013 / 038650. Furthermore, the third compound can be manufactured, for example, by using known alternative reactions and starting materials that are compatible with the target compound.

[0990] Examples of substituents in the third compound are shown below, but the invention is not limited to these examples.

[0991] Specific examples of aryl (sometimes called aromatic hydrocarbon groups) include phenyl, tolyl, xylyl, naphthyl, phenanthrene, pyrene, etc. Benzyl, benzo[c]phenanthrene, benzo[g] Examples of suitable compounds include phenyl, benzo[a]anthrayl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, biphenyl, terphenyl, tetraphenyl, fluoranthyl, etc., with phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, triphenylene, and fluorenyl being preferred examples.

[0992] Examples of aryl groups with substituents include tolyl, xylyl, and 9,9-dimethylfluorenyl.

[0993] As illustrated in the specific example, aryl groups include both fused aryl groups and unfused aryl groups.

[0994] The preferred aryl group is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, triphenylene, or fluorene.

[0995] Specific examples of heteroaryl groups (sometimes called heterocyclic groups, heteroaromatic cyclic groups, or aromatic heterocyclic groups) include pyrroloyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, triazinyl, indoleyl, isoindoleyl, imidazoyl, benzimidazolyl, indoleyl, imidazo[1,2-a]pyridinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, azadibenzothiophenyl, quinyl Phinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, naphridinyl, carbazole, azacarbazole, phenanthridine, acridine, phenantholinyl, phenazinyl, phenothiazinyl, phenotoxazinyl, oxazolyl, oxadiazolyl, furo-coryl, benzoxazolyl, thiophene, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., preferably including dibenzofuranyl, dibenzothiophene, carbazole, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothiophene.

[0996] As a heteroaryl group, it is preferably dibenzofuranyl, dibenzothiophene, carbazoyl, pyridyl, pyrimidinyl, triazine, azidodibenzofuranyl or azidodibenzothiophene, and more preferably dibenzofuranyl, dibenzothiophene, azidodibenzofuranyl or azidodibenzothiophene.

[0997] In the third compound, the substituted silyl group is preferably selected from the group consisting of substituted or unsubstituted trialkylsilyl groups, substituted or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups.

[0998] Specific examples of substituted or unsubstituted trialkylsilyl compounds include trimethylsilyl and triethylsilyl.

[0999] Specific examples of substituted or unsubstituted arylalkylsilyl compounds include diphenylmethylsilyl, xylylmethylsilyl, and phenyldimethylsilyl.

[1000] Specific examples of substituted or unsubstituted triarylsilyl compounds include triphenylsilyl and trimethylsilyl.

[1001] In the third compound, the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group.

[1002] Specific examples of substituted or unsubstituted diarylphosphine oxides include diphenylphosphine oxide and xylylphosphine oxide.

[1003] In the third compound, a substituted carboxyl group can be, for example, benzoyloxy.

[1004] <The relationship between the first, second, and third compounds in the luminescent layer>

[1005] In the organic EL element 1 of this embodiment, the singlet state energy S1(M1) of the first compound, the singlet state energy S1(M2) of the second compound, and the singlet state energy S1(M3) of the third compound in the light-emitting layer 5 satisfy the following mathematical formula (number 1).

[1006] S1(M3)>S1(M2)>S1(M1)…(Number 1)

[1007] The band gap T of the first compound in the luminescent layer 5 at 77 [K] 77K The band gap T at 77 [K] for (M1) and the second compound 77K The band gap T of (M2) and the third compound at 77 [K] 77K (M3) is preferably a relation that satisfies the following mathematical expression (number 2).

[1008] T 77K (M3)>T 77K (M2)>T 77K (M1)…(Number 2)

[1009] In this embodiment, the singlet energy S1(M2) of the second compound and the band gap T at 77 [K] of the second compound are... 77K The difference ΔST(M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, and even more preferably less than 0.1 eV. That is, ΔST(M2) preferably satisfies the following mathematical expressions (Number 1A) to (Number 1C).

[1010] △ST(M2)=S1(M2)-T 77K (M2) < 0.3 eV (Number 1A)

[1011] △ST(M2)=S1(M2)-T 77K (M2) < 0.2 eV (Number 1B)

[1012] △ST(M2)=S1(M2)-T 77K (M2) < 0.1 eV (1C)

[1013] In this embodiment, the preferred singlet energy S1(M1) of the first compound is the same as the band gap T at 77 [K] of the first compound. 77K The difference △ST(M1) between (M1) satisfies the following mathematical expression (number 1D).

[1014] △ST(M1)=S1(M1)-T 77K (M1)>0.3[eV]…(Number 1D)

[1015] In this embodiment, the preferred singlet state energy S1(M3) of the third compound is the same as the band gap T at 77 [K] of the third compound. 77K The difference △ST(M3) between (M3) satisfies the following mathematical expression (E).

[1016] △ST(M3)=S1(M3)-T 77K (M3)>0.3[eV]…(number 1E)

[1017] In this embodiment, the band gap T is preferably at 77 [K] of the third compound. 77K (M3) is above 2.9 eV. It can be considered that by giving the third compound such a band gap T... 77K (M3), in the luminescent layer, can effectively confine the triplet energy of the second compound (the compound with delayed fluorescence) within the luminescent layer.

[1018] • TADF mechanism

[1019] In the organic EL element 1 of this embodiment, a compound with a small ΔST(M2) is preferably used as the second compound. With thermal energy supplied from the outside, reverse intersystem crossing from the triplet energy level to the singlet energy level of the second compound can easily occur. The energy state transformation mechanism in which the excited triplet state of the exciton obtained by electrical excitation inside the organic EL element exchanges spin with the excited singlet state through reverse intersystem crossing is called the TADF mechanism.

[1020] Figure 4 This is a diagram illustrating an example of the energy level relationship between the first, second, and third compounds in the luminescent layer 5. Figure 4 In this diagram, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. Figure 4 The dashed arrow from S1(M2) to S1(M1) represents the Foster-type energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound.

[1021] like Figure 4As shown, if a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo a reverse intersystem crossing to the lowest excited singlet state S1(M2) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1022] • Relationship between triplet energy and band gap at 77 K

[1023] Here, the relationship between the triplet energy and the band gap at 77 [K] is explained. In this embodiment, the band gap at 77 [K] differs from the normally defined triplet energy.

[1024] The triplet energy was measured as follows. First, the compound to be measured was dissolved in a suitable solvent, and the resulting solution was sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy was calculated based on the wavelength value of the intersection of the tangent and the horizontal axis according to the prescribed conversion formula.

[1025] In this embodiment, the compound with thermally activated delayed fluorescence is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state coexist. As a result, it can be considered that the spectrum measured in the same way as above contains emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the emission comes from, but the value of the triplet energy is basically dominant.

[1026] Therefore, in this embodiment, the measurement method is the same as that for the usual triplet energy T, but in order to distinguish it strictly, the measured value is referred to as the bandgap T. 77K The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge[nm], the energy calculated according to the following conversion formula (F1) is taken as the band gap T at 77[K]. 77K .

[1027] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[1028] The tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum is drawn as shown below. Consider this tangent as it moves along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the point on the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis value increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum.

[1029] Furthermore, the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point closest to the maximum value on the shortest wavelength side and where the slope value is the maximum value is taken as the tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum.

[1030] Phosphorescence can be measured using the main body of the Hitachi High Technology Co., Ltd. F-4500 spectrophotometer. However, the measuring device is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.

[1031] Singlet energy S1

[1032] The following methods can be cited as examples of methods for measuring the singlet energy S1 using a solution (sometimes called the solution method).

[1033] A 10 μmol / L toluene solution of the compound to be measured was placed in a quartz cell, and the absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). A tangent was drawn to the falling edge of the longer wavelength side of the absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy.

[1034] Conversion formula (F2): S1[eV]=1239.85 / λedge

[1035] As an absorption spectroscopy measuring device, an example of such a device is the Hitachi spectrophotometer (device name: U3310), but it is not limited to this.

[1036] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is plotted as shown below. Consider this tangent at various points on the spectral curve as the maximum value on the longest wavelength side of the absorption spectrum is moved along the longer wavelength direction. This tangent repeatedly shows a decreasing and then increasing slope as the curve descends (i.e., as the vertical axis value decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent to the falling edge of the longer wavelength side of the absorption spectrum.

[1037] In addition, the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[1038] In this embodiment, the singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as △ST.

[1039] Preferably, when the organic EL element 1 of this embodiment emits light, the light-emitting layer 5 mainly contains fluorescent compounds that emit light.

[1040] The organic EL element 1 of this embodiment preferably emits red or green light.

[1041] In the case where the organic EL element 1 of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 500 nm or more and 560 nm or less.

[1042] In the case where the organic EL element 1 of this embodiment emits red light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 600 nm or more and 660 nm or less.

[1043] In the case where the organic EL element 1 of this embodiment emits blue light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 430 nm or more and 480 nm or less.

[1044] The main peak wavelength of the light emitted from the organic EL element 1 is measured as described below.

[1045] The applied voltage to organic EL element 1 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta) to achieve a current density of 10 mA / cm². 2 The spectrophotometric emission brightness spectrum at that time.

[1046] In the obtained spectrophotometric emission brightness spectrum, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum is measured and taken as the main peak wavelength (unit: nm).

[1047] • Film thickness of the light-emitting layer

[1048] The thickness of the light-emitting layer 5 in the organic EL element 1 of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. If it is 5 nm or more, the formation of the light-emitting layer and the adjustment of the color become easier, and if it is 50 nm or less, it is easier to suppress the rise of the driving voltage.

[1049] • The content of compounds in the luminescent layer

[1050] In the organic EL element 1 of this embodiment, the content of the first compound in the light-emitting layer 5 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less.

[1051] The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[1052] The content of the third compound is preferably 10% by mass or more and 80% by mass or less.

[1053] The total content of the first compound, the second compound, and the third compound in the light-emitting layer 5 is capped at 100% by mass. Furthermore, it is not excluded that the light-emitting layer 5 in this embodiment may contain materials other than the first compound, the second compound, and the third compound.

[1054] The luminescent layer 5 may contain only one first compound or two or more first compounds. The luminescent layer 5 may contain only one second compound or two or more second compounds. The luminescent layer 5 may contain only one third compound or two or more third compounds.

[1055] The organic EL element 1 according to the first embodiment emits light at low voltage or high efficiency, or at low voltage and high efficiency. The organic EL element 1 of the first embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1056] The structure of the organic EL element 1 will be further described below. Reference numerals will sometimes be omitted from the descriptions in the accompanying drawings.

[1057] (Substrate)

[1058] The substrate is used as a support for organic EL (electro-optical) devices. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. Flexible substrates are (flexible) substrates that can be bent; examples include plastic substrates. Materials used to form plastic substrates include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.

[1059] (anode)

[1060] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), silicon- or silicon-oxide-containing indium tin oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include nitrides of gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or metallic materials (e.g., titanium nitride).

[1061] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. In addition, they can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, etc.

[1062] In the EL layer formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that is independent of the work function of the anode and is easy to inject holes (cavities). Therefore, materials that can be used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1063] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table that have low work functions, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr) and their alloys (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb) and their alloys. Furthermore, when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Moreover, when using silver paste, coating or inkjet methods can be used.

[1064] (cathode)

[1065] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them.

[1066] Furthermore, when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[1067] Furthermore, by incorporating an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[1068] (hole injection layer)

[1069] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[1070] In addition, examples of substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylamino)- ...]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N Aromatic amine compounds such as [phenyl]-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[1071] Furthermore, as substances with high hole injection capability, polymeric compounds (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymeric compounds with added acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[1072] (Hole transport layer)

[1073] The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, and anthracene derivatives can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N Aromatic amine compounds such as [-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-difluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) are mentioned here. The substances discussed here mainly possess 10... -6 cm 2 Substances with a hole mobility of / (V·s) or higher.

[1074] The hole transport layer can use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnt. Polymer compounds such as poly(N-vinylcarbazole) (PVK) or poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[1075] However, any other material may be used as long as it has a higher hole transport capacity than electrons. Furthermore, the layer containing the material with high hole transport capacity can be not only a single layer, but also a layer obtained by stacking two or more layers of the aforementioned material.

[1076] When configuring two or more hole transport layers, it is preferable to configure a material with a larger bandgap on the side closer to the light-emitting layer. HT-2, used in the embodiments described later, is an example of such a material.

[1077] (Electron transport layer)

[1078] The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can preferably be used. The substances mentioned herein mainly have a 10 -6 cm 2 Materials with an electron mobility of / (V·s) or higher. Furthermore, any material whose electron transport is higher than its hole transport can be used as the electron transport layer, except for those mentioned above. Moreover, the electron transport layer can be a single layer or composed of two or more layers of the aforementioned materials stacked together.

[1079] In addition, polymeric compounds can be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[1080] (Electron injection layer)

[1081] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. In addition, materials obtained by containing alkali metals, alkaline earth metals, or their compounds in a substance with electron transport properties can be used, specifically materials obtained by containing magnesium (Mg) in Alq. Furthermore, in this case, electron injection from the cathode can be performed more efficiently.

[1082] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material generates electrons in the organic compound through the electron donor, thus exhibiting good electron injection and electron transport properties. In this case, the organic compound is preferably a material with good electron transport properties, specifically, substances constituting the electron transport layer described above (metal complexes or heteroaromatic compounds, etc.) can be used. The electron donor is any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Furthermore, alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, barium oxides, etc. In addition, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1083] (Layer Formation Method)

[1084] The method for forming each layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. Known methods such as dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as spin coating, dip coating, flow coating, and inkjet coating can be used.

[1085] (film thickness)

[1086] The thickness of each organic layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. However, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a higher applied voltage is required and the efficiency will be reduced. Therefore, the preferred thickness is usually in the range of several nm to 1 μm.

[1087] [Second Implementation]

[1088] [Electronic Devices]

[1089] The electronic device of this embodiment is equipped with the organic EL element of the above embodiment. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[1090] [Variations on the implementation method]

[1091] Furthermore, the present invention is not limited to the above-described embodiments, and any modifications or improvements made within the scope of achieving the objectives of the present invention are included within the scope of the present invention.

[1092] For example, the light-emitting layer is not limited to a single layer; multiple light-emitting layers can be stacked. In the case of an organic EL device having multiple light-emitting layers, it is sufficient as long as at least one light-emitting layer meets the conditions described in the above embodiments. For example, the other light-emitting layers can be either fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize the emission caused by electron migration directly from the triplet excited state to the ground state.

[1093] Furthermore, in the case of an organic EL element having multiple light-emitting layers, these light-emitting layers can be arranged adjacent to each other, or they can be a so-called tandem organic EL element consisting of multiple light-emitting units stacked with an intermediate layer in between.

[1094] Furthermore, a blocking layer is preferably disposed adjacent to at least one of the anode and cathode sides of the light-emitting layer. The blocking layer is preferably disposed grounded with the light-emitting layer to block at least one of holes, electrons, and excitons.

[1095] Specifically, in this embodiment, an electron blocking layer is disposed adjacent to the light-emitting layer on the anode side of the light-emitting layer as the first layer. It can be considered that since the first layer contains a compound represented by general formula (1), if the first layer is an electron blocking layer, the ionization potential Ip becomes deeper (the absolute value becomes larger). As a result, electrons can be blocked efficiently.

[1096] Furthermore, on the cathode side of the light-emitting layer, in this embodiment, a hole-blocking layer is disposed adjacent to the light-emitting layer as a second layer. It can be considered that since the second layer contains a compound represented by general formula (2), if the second layer is a hole-blocking layer, the electron affinity level Af becomes shallower (the absolute value becomes smaller). As a result, holes can be blocked efficiently.

[1097] Preferably, the light-emitting layer is bonded to the electron blocking layer. Preferably, the light-emitting layer is bonded to the hole blocking layer.

[1098] In addition, the specific structure and shape in the implementation of the present invention may adopt other structures within the scope of achieving the purpose of the present invention.

[1099] In this specification, the numerical range indicated by “~” refers to the range included by taking the value before “~” as the lower limit and the value after “~” as the upper limit.

[1100] In this specification, the mutual bonding of Rx and Ry to form a ring means, for example, that Rx and Ry contain carbon, nitrogen, oxygen, sulfur, or silicon atoms, and that the atoms in Rx (carbon, nitrogen, oxygen, sulfur, or silicon) are bonded to the atoms in Ry (carbon, nitrogen, oxygen, sulfur, or silicon) via single, double, triple, or divalent connecting groups to form a ring with five or more ring atoms (specifically, a heterocycle or aromatic hydrocarbon ring). x is a number, a letter, or a combination of numbers and letters. y is a number, a letter, or a combination of numbers and letters.

[1101] There are no particular limitations on the divalent linking group, for example -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa-, and groups obtained by combining two or more of these linking groups.

[1102] In this specification, unless otherwise specified, specific examples of heterocycles may be given by removing chemical bonds from the "heteroaryl Sub2" illustrated in the "Explanation of Substituents in the General Formula" section described later. These heterocycles may have substituents.

[1103] In this specification, unless otherwise specified, specific examples of aromatic hydrocarbon rings may be given by removing chemical bonds from the "aryl Sub1" illustrated in the "Explanation of Substituents in the General Formula" section described later. These aromatic hydrocarbon rings may have substituents.

[1104] Examples of Ra include, for instance, alkyl Sub3 with 1 to 30 carbon atoms that are substituted or unsubstituted, aryl Sub1 with 6 to 30 carbon atoms that are substituted or unsubstituted, and heteroaryl Sub2 with 5 to 30 carbon atoms that are substituted or unsubstituted, as illustrated in the “Explanation of Substituents in the General Formula” described later.

[1105] For example, the formation of a ring by mutual bonding of Rx and Ry means that: in the molecular structure represented by the following general formula (E1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring (ring structure) E represented by general formula (E2); in the molecular structure represented by general formula (F1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring F represented by general formula (F2); in the molecular structure represented by general formula (G1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring G represented by general formula (G2); in the molecular structure represented by general formula (H1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring H represented by general formula (H2); and in the molecular structure represented by general formula (I1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring I represented by general formula (I2).

[1106] In general formulas (E1) to (I1), * independently represents the position of a bond with other atoms in a molecule. The two * in general formula (E1) correspond to the two * in general formula (E2), the two * in general formula (F1) correspond to the two * in general formula (F2), the two * in general formula (G1) correspond to the two * in general formula (G2), the two * in general formula (H1) correspond to the two * in general formula (H2), and the two * in general formula (I1) correspond to the two * in general formula (I2).

[1107] [Chemistry 129]

[1108]

[1109] [Chemistry 130]

[1110]

[1111] In the molecular structures represented by general formulas (E2) to (I2), E to I represent ring structures (rings with 5 or more ring atoms). In general formulas (E2) to (I2), * independently represents the position of bonding with other atoms in a molecule. The two * in general formula (E2) correspond to the two * in general formula (E1). Similarly, the two * in general formulas (F2) to (I2) also correspond to the two * in general formulas (F1) to (I1).

[1112] For example, in general formula (E1), where Rx1 and Ry1 are bonded together to form ring E in general formula (E2), and ring E is an unsubstituted benzene ring, the molecular structure represented by general formula (E1) becomes the molecular structure represented by the following general formula (E3). Here, the two asterisks in general formula (E3) correspond independently to the two asterisks in general formula (E2) and general formula (E1), respectively.

[1113] For example, in general formula (E1), if Rx1 and Ry1 are bonded together to form ring E in general formula (E2), and ring E is an unsubstituted pyrrole ring, the molecular structure represented by general formula (E1) becomes the molecular structure represented by the following general formula (E4). Here, the two asterisks in general formula (E4) correspond independently to the two asterisks in general formula (E2) and general formula (E1), respectively. In general formulas (E3) and (E4), asterisks independently represent the positions in a molecule that are bonded to other atoms.

[1114] [Chemistry 131]

[1115]

[1116] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the atoms constituting the ring itself in a compound with a cyclic structure formed by atomic bonds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming the ring" as used below is the same unless otherwise specified. For example, the number of carbon atoms forming the ring of a benzene ring is 6, the number of carbon atoms forming the ring of a naphthalene ring is 10, the number of carbon atoms forming the ring of a pyridyl group is 5, and the number of carbon atoms forming the ring of a furanyl group is 4. Furthermore, when an alkyl group, for example, is substituted on a benzene or naphthalene ring, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms forming the ring. Additionally, when a fluorene ring, for example, is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms in the fluorene ring as a substituent is not included in the number of carbon atoms forming the ring.

[1117] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, aggregated rings, carbocyclic compounds, heterocyclic compounds) that form a cyclic structure (e.g., monocyclic, fused-ring, aggregated rings) by atomic bonds. Atoms that do not constitute a ring, and atoms contained in substituents when the ring is substituted, are not included in the number of cyclic atoms. This also applies to the "number of cyclic atoms" described below unless otherwise specified. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. Hydrogen atoms bonded to the carbon atoms of the pyridine or quinazoline rings, and atoms constituting substituents, are not included in the number of cyclic atoms. Furthermore, in cases where a fluorene ring is bonded to a fluorene ring as a substituent (including spirofluorene rings), the number of fluorene ring atoms as substituents is not included in the number of cyclic atoms.

[1118] • Explanation of each substituent in the general formulas in this specification (Explanation of each substituent)

[1119] In this specification, aryl (sometimes referred to as aromatic hydrocarbon group) is, for example, arylSub1, derived from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluorenyl, pyrene, etc. Benzyl, fluoranthyl, benzo[a]anthrayl, benzo[c]phenanthryl, triphenylene, benzo[k]fluoranthyl, benzo[g] At least one group selected from the group consisting of alkyl, benzo[b]triphenylene, picenyl, and perylenyl.

[1120] The aryl Sub1 in this specification preferably has 6 to 30 carbon atoms in its ring, more preferably 6 to 20, even more preferably 6 to 14, and still more preferably 6 to 12. Among the above-mentioned aryl Sub1, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, and fluorenyl are preferred. For 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, and 4-fluorenyl, the carbon atom at position 9 is preferably substituted by a substituted or unsubstituted alkyl Sub3 or a substituted or unsubstituted aryl Sub1 as described later in this specification.

[1121] In this specification, the heteroaryl group (sometimes referred to as a heterocyclic group, heteroaromatic cyclic group, or aromatic heterocyclic group) is, for example, the heterocyclic group Sub2. The heterocyclic group Sub2 is a group containing at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium, and germanium atoms as a heteroatom. Preferably, the heterocyclic group Sub2 contains at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom.

[1122] The heterocyclic group Sub2 in this specification includes, for example, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthroxolinyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indoleyl, benzimidazolyl, indazolyl, imidazopyridyl, benzotriazolyl, carbazole, furanyl, thiophene, and oxazolyl. The group selected from the group consisting of , thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzoisoxazolyl, benzoisothiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothiaphenyl, piperidinyl, pyrrolyl, piperazine, morpholinyl, phenazinyl, phenothiazinyl, and phenothiazinyl.

[1123] The heterocyclic group Sub2 in this specification preferably has 5 to 30 cyclic atoms, more preferably 5 to 20, and even more preferably 5 to 14. Among the above-mentioned heterocyclic groups Sub2, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, and 9-carbazoleyl are even more preferred. Regarding 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, and 4-carbazoleyl, the nitrogen atom at the 9-position is preferably substituted by a substituted or unsubstituted aryl group Sub1 or a substituted or unsubstituted heterocyclic group Sub2 as described in this specification.

[1124] Furthermore, in this specification, the heterocyclic group Sub2 may, for example, be a group derived from a local structure represented by the following general formulas (XY-1) to (XY-18).

[1125] [Chemistry 132]

[1126]

[1127] [Chemistry 133]

[1128]

[1129] [Chemistry 134]

[1130]

[1131] In the general formulas (XY-1) to (XY-18), X A and Y A Each atom is an independent heteroatom, preferably an oxygen atom, sulfur atom, selenium atom, silicon atom, or germanium atom. The local structure represented by the general formula (XY-1) to (XY-18) has chemical bonds at any position to form a heterocyclic group, which may have substituents.

[1132] Furthermore, in this specification, the heterocyclic group Sub2 can also be represented by the following general formulas (XY-19) to (XY-22). Additionally, the positions of the chemical bonds can be appropriately changed.

[1133] [Chemistry 135]

[1134]

[1135] The alkyl group in this specification can be any of a straight-chain alkyl group, a branched alkyl group, or a cyclic alkyl group.

[1136] In this specification, alkyl groups are, for example, alkyl Sub3.

[1137] In this specification, straight-chain alkyl groups are, for example, straight-chain alkyl sub. 31 .

[1138] In this specification, branched alkyl groups are, for example, branched alkyl subs. 32 .

[1139] The cyclic alkyl group in this specification is, for example, a cyclic alkyl sub. 33 .

[1140] Alkyl Sub3, for example, is derived from straight-chain alkyl Sub 31 Branched alkyl Sub 32 and cyclic alkyl sub 33 At least one group selected from the group constitutes the composition.

[1141] Straight-chain alkyl sub 31 or branched alkyl sub 32 For example, at least one group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl.

[1142] The straight-chain alkyl sub in this specification 31 or branched alkyl sub 32 The number of carbon atoms is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and still more preferably 1 to 6. As the above-mentioned straight-chain alkyl Sub 31 or branched alkyl sub 32 More preferably, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, pentyl, isopentyl, and neopentyl.

[1143] The cyclic alkyl sub in this specification 33 For example, cycloalkyl Sub 331 .

[1144] The cycloalkyl sub in this specification 331 For example, at least one group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, and norbornyl. Cycloalkyl Sub 331 The preferred number of carbon atoms in the cyclic compound is 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and even more preferably 5 to 8. In the cycloalkyl sub 331More preferably, cyclopentyl or cyclohexyl.

[1145] In this specification, the alkyl halogroup is, for example, alkyl halogroup Sub4, which is, for example, alkyl Sub3 obtained by substituting one or more halogen atoms, preferably by substituting fluorine atoms.

[1146] The alkyl halogroup Sub4 in this specification is, for example, selected from at least one group selected from the group consisting of fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethylmethyl, trifluoroethyl and pentafluoroethyl.

[1147] In this specification, substituted silyl groups are, for example, substituted silyl Sub5, which is derived from alkyl silyl Sub... 51 and arylsilyl Sub 52 At least one group selected from the group constitutes the composition.

[1148] The alkylsilyl sub in this specification 51 For example, a trialkylsilyl sub-sub-containing alkyl Sub3 as described above. 511 .

[1149] Trialkylsilyl Sub 511 For example, at least one group selected from the group consisting of trimethylsilyl, triethylsilyl, tri-n-butylsilyl, tri-n-octylsilyl, triisobutylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-propylsilyl, dimethyl-n-butylsilyl, dimethyl-tert-butylsilyl, diethylisopropylsilyl, vinyldimethylsilyl, propyldimethylsilyl, and triisopropylsilyl. Trialkylsilyl Sub 511 The three alkyl groups Sub3 in the formula can be the same as or different from each other.

[1150] The arylsilyl sub in this specification 52 For example, from dialkylarylsilylsub 521 alkyl diarylsilyl Sub 522 and triarylsilyl Sub 523 At least one group selected from the group constitutes the composition.

[1151] Dialkylarylsilyl Sub 521 For example, a dialkylarylsilyl group having two of the above-mentioned alkyl groups Sub3 and one of the above-mentioned aryl groups Sub1. Dialkylarylsilyl Sub 521 The preferred number of carbon atoms is 8 to 30.

[1152] Alkyl diarylsilyl sub 522For example, an alkyl diarylsilyl group having one of the above-mentioned alkyl groups Sub3 and two of the above-mentioned aryl groups Sub1. Alkyl diarylsilyl Sub 522 The preferred number of carbon atoms is 13 to 30.

[1153] Triarylsilyl Sub 523 For example, a triarylsilyl group having three of the above-mentioned aryl groups Sub1. Triarylsilyl Sub 523 The preferred number of carbon atoms is 18 to 30.

[1154] The substituted or unsubstituted alkyl sulfonyl group in this specification is, for example, alkyl sulfonyl Sub6, alkyl sulfonyl Sub6 with -SO2R w express. -SO2R w R in w The above alkyl group Sub3 is indicated as substituted or unsubstituted.

[1155] In this specification, aralkyl (sometimes referred to as arylalkyl) is, for example, aralkyl Sub7. The aryl group in aralkyl Sub7 includes, for example, at least one of the aryl Sub1 and the heteroaryl Sub2 described above.

[1156] In this specification, the aralkyl Sub7 is preferably a group having an aryl Sub1, denoted as -Z3-Z4. Z3 is, for example, an alkylene group corresponding to the aforementioned alkyl Sub3. Z4 is, for example, the aforementioned aryl Sub1. Preferably, the aryl portion of the aralkyl Sub7 has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl portion has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6). The aralkyl group Sub7 is, for example, at least one group selected from the group consisting of benzyl, 2-phenylpropane-2-yl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[1157] In this specification, the alkoxy group is, for example, alkoxy Sub8, which is represented as -OZ1. Z1 is, for example, the aforementioned alkyl Sub3. Alkoxy Sub8 is, for example, at least one group selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. The number of carbon atoms in the alkoxy Sub8 is preferably 1 to 30, more preferably 1 to 20.

[1158] In this specification, the haloalkoxy group is, for example, haloalkoxy Sub9, which is, for example, an alkoxy group obtained by substituting the above-mentioned alkoxy Sub8 with one or more halogen atoms, preferably with fluorine atoms.

[1159] The aryloxy group (sometimes called arylalkoxy) in this specification is, for example, arylalkoxy Sub. 10 Arylalkoxy Sub 10 The aryl group in the aryl group includes at least one of aryl Sub1 and heteroaryl Sub2.

[1160] The arylalkoxy Sub in this specification 10 Represented as -OZ2. This Z2 is, for example, arylSub1 or heteroarylSub2. ArylalkoxySub 10 The preferred number of carbon atoms in the cyclic compound is 6 to 30, more preferably 6 to 20. As this arylalkoxy sub 10 For example, phenoxy groups can be cited.

[1161] The substituted amino group in this specification is, for example, a substituted amino group Sub. 11 Subsubstituted amino groups 11 For example, from arylamino Sub 111 and alkylamino Sub 112 At least one group selected from the group constitutes the composition.

[1162] Arylamino Sub 111 Represented as -NHR V1 、or -N(R V1 )2. The R V1 For example, arylSub1. -N(R) V1 The two R's in )2 V1 Same or different.

[1163] Alkylamino Sub 112 Represented as -NHR V2 、or -N(R V2 )2. The R V2 For example, alkyl Sub3-N(R) V2 The two R's in )2 V2 Same or different.

[1164] In this specification, the alkenyl group is, for example, an alkenyl sub. 12 alkenyl Sub 12 It is any one of straight-chain or branched chains, for example, at least one group selected from the group consisting of vinyl, propenyl, butenyl, oleenyl, eicosaptenyl, docosahexaenoyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl and 2-phenyl-2-propenyl.

[1165] In this specification, the alkynyl group is, for example, alkynyl group Sub. 13 , acetylenic Sub 13 It can be either straight-chain or branched, for example, at least one group selected from the group consisting of ethynyl, propynyl and 2-phenylethynyl.

[1166] In this specification, the alkylthio group is, for example, alkylthio group Sub. 14 .

[1167] Alkylthiosub 14 Represented as -SR V3 The R V3 For example, alkyl Sub3. Alkylthio Sub 14 The number of carbon atoms is preferably 1 to 30, more preferably 1 to 20.

[1168] In this specification, the aryl thio group is, for example, aryl thio group Sub. 15 .

[1169] Arylthiosub 15 Represented as -SR V4 The R V4 For example, aryl Sub1. Arylthio Sub 15 The number of cyclic carbons is preferably 6 to 30, more preferably 6 to 20.

[1170] Examples of halogen atoms in this specification include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms being preferred.

[1171] The substituted phosphine group in this specification is, for example, a substituted phosphine group Sub. 16 , substituted phosphine-based Sub 16 For example, phenylphosphine group.

[1172] In this specification, aryl carbonyl groups are, for example, aryl carbonyl groups (Sub). 17 aryl carbonyl Sub 17 It is represented as -COY'. The Y' is, for example, aryl Sub1. The aryl carbonyl Sub in this specification... 17 For example, at least one group selected from the group consisting of phenylcarbonyl, diphenylcarbonyl, naphthylcarbonyl and triphenylcarbonyl.

[1173] In this specification, the acyl group is, for example, an acyl group (Sub). 18 Acyl Sub 18 It is represented as -COR'. The R' is, for example, an alkyl Sub3. The acyl Sub in this specification... 18 For example, at least one group selected from the group consisting of acetyl and propionyl.

[1174] The substituted phosphoryl group in this specification is, for example, a substituted phosphoryl group Sub. 19 Subsubstituted phosphoryl group 19 It is represented by the following general formula (P).

[1175] [Chemistry 136]

[1176]

[1177] In the general formula (P), Ar P1 and Ar P2 It is any substituent selected from the group consisting of the above-mentioned alkyl Sub3 and the above-mentioned aryl Sub1.

[1178] In this specification, the ester group is, for example, the ester group Sub. 20 ester group Sub 20 For example, any group selected from the group consisting of alkyl esters and aryl esters.

[1179] In this specification, the alkyl ester group is, for example, an alkyl ester group Sub. 201 alkyl ester group Sub 201 Represented as -C(=O)OR E R E For example, the above-mentioned alkyl Sub3, whether substituted or unsubstituted.

[1180] In this specification, the aryl ester group is, for example, an aryl ester group Sub. 202 aryl ester group Sub 202 Represented as -C(=O)OR Ar R Ar For example, the above-mentioned aryl Sub1 may be substituted or unsubstituted.

[1181] In this specification, siloxane alkyl groups are, for example, siloxane sub-alkyl groups. 21 Siloxane Sub 21 It is a silicon compound group obtained via an ether bond. Siloxane Sub 21 For example, trimethylsiloxane.

[1182] In this specification, the carbamoyl group is represented as -CONH2.

[1183] The substituted carbamoyl group in this specification is, for example, carbamoyl Sub. 22 Carbamoyl Sub 22 Represented as -CONH-Ar C 、or -CONH-R C Ar CFor example, at least one group selected from the group consisting of substituted or unsubstituted aryl Sub1 (preferably with 6 to 10 cyclic carbon atoms) and heteroaryl Sub2 (preferably with 5 to 14 cyclic atoms). C It can be a group obtained by bonding aryl Sub1 and heteroaryl Sub2.

[1184] R C For example, the above-mentioned alkyl Sub3 (preferably with 1 to 6 carbon atoms) may be substituted or unsubstituted.

[1185] In this specification, "cyclic carbon" refers to the carbon atom that constitutes a saturated ring, unsaturated ring, or aromatic ring. "Cyclic atom" refers to the carbon atom and heteroatom that constitute a heterocycle (including saturated rings, unsaturated rings, and aromatic rings).

[1186] In addition, in this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[1187] Hereinafter, alkylSub3 refers to the straight-chain alkylSub as described in the "Explanation of Substituents" section. 31 Branched alkyl Sub 32 and cyclic alkyl sub 33 One or more of the following groups.

[1188] Similarly, substituted silyl Sub5 refers to alkylsilyl Sub 51 and arylsilyl Sub 52 One or more of the following groups.

[1189] Similarly, substituted amino Sub 11 It refers to arylamino Sub 111 and alkylamino Sub 112 One or more of the following groups.

[1190] In this specification, a substituent is referred to as "substituted or unsubstituted" in such cases, for example, substituent R. F1 , substituent R F1 From aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 Carbamoyl Sub 22 At least one group selected from the group consisting of an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxyl group, a nitro group, and a carboxyl group.

[1191] In this specification, the substituent R is used in cases of "substituted or unsubstituted". F1 It can also be diarylboryl (Ar) B1 Ar B2 B-). As the Ar B1 and Ar B2 Examples of this can be found in the aforementioned aryl Sub1. Ar B1 Ar B2 Ar in B- B1 And Ar B2 Same or different.

[1192] As a substituent R F1 Specific examples and preferred groups can be exemplified by the substituents listed in "Description of Substituents" (e.g., aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub9). 10 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 and carbamoyl Sub 22 ) Specific examples and preferred groups are the same groups.

[1193] Substituent R in cases of "substituted or unsubstituted" F1It can be derived from aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 Carbamoyl Sub 22 At least one group selected from the group consisting of unsubstituted amino, unsubstituted silyl, halogen atom, cyano, hydroxyl, nitro and carboxyl (hereinafter also referred to as substituent R) F2 Further substitution. In addition, these multiple substituents R F2 They can also bond together to form a ring.

[1194] In the case of "substituted or unsubstituted", "unsubstituted" means not substituted by the substituent R. F1 It is replaced by a hydrogen atom and bonded together.

[1195] Furthermore, in this specification, the phrase "a ZZ group with XX to YY carbons, whether substituted or unsubstituted" refers to the number of carbons when the ZZ group is unsubstituted, and the number of carbons when there is no substitution (R). F1 The number of carbon atoms.

[1196] In this specification, the phrase "ZZ group with XX to YY atoms, whether substituted or unsubstituted" refers to the number of atoms in the unsubstituted ZZ group, and the number of atoms in the unsubstituted ZZ group. F1 The number of atoms.

[1197] The same applies to the cases of "substituted or unsubstituted" in the compounds or their partial structures described in this specification.

[1198] In this specification, when substituents bond to each other to form a ring, the structure of the ring is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.

[1199] In this specification, the aromatic hydrocarbon group in the linking group can be, for example, a divalent or higher group obtained by removing one or more atoms from the monovalent aryl Sub1 described above.

[1200] In this specification, as a heterocyclic group in the linking group, examples include divalent or higher groups obtained by removing one or more atoms from the monovalent heteroaryl Sub2 described above.

[1201] Example

[1202] The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[1203] <Compound>

[1204] The compounds represented by general formula (1) used for the manufacture of organic EL elements in Examples 1 to 10 are shown below.

[1205] [Chemistry 137]

[1206]

[1207] [Chemistry 138]

[1208]

[1209] The compounds represented by general formula (2) used for the manufacture of organic EL elements in Examples 1 to 10 are shown below.

[1210] [Chemistry 139]

[1211]

[1212] The structures of the comparative compounds used in the manufacture of the organic EL elements of Comparative Examples 1-4 are shown below.

[1213] [Chemistry 140]

[1214]

[1215] The structures of other compounds used in the manufacture of the organic EL elements of Examples 1-10 and Comparative Examples 1-4 are shown below.

[1216] [Chemistry 141]

[1217]

[1218] [Chemistry 142]

[1219]

[1220] [Chemistry 143]

[1221]

[1222] [Chemistry 144]

[1223]

[1224] [Chemistry 145]

[1225]

[1226] <Fabrication of Organic EL Components 1>

[1227] Organic EL elements were fabricated and evaluated as described below.

[1228] [Example 1]

[1229] A glass substrate (manufactured by Geoma Technology Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130nm.

[1230] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compounds HT and HA were co-deposited onto the side with the transparent electrode lines, forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[1231] Next, compound HT is deposited on the hole injection layer to form a hole transport layer with a thickness of 200 nm.

[1232] Next, compound EBL-1 is deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm as the first layer.

[1233] Next, a light-emitting layer with a thickness of 25 nm was formed by co-depositing the first fluorescent compound RD, the second delayed fluorescent compound TADF-1, and the third compound CBP onto the electron blocking layer. The concentrations of compound RD, TADF-1, and CBP in the light-emitting layer were set to 1% by mass, 25% by mass, and 74% by mass.

[1234] Next, compound HBL-1 is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm as the second layer.

[1235] Next, the compound ET is deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm.

[1236] Next, lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1237] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1238] If the component configuration of the organic EL element of Example 1 is shown in a simplified manner, it is as follows.

[1239] ITO(130) / HT: HA(10, 97%: 3%) / HT (200) / EBL-1(10) / CBP: TADF-1: RD (25, 74%: 25%: 1%) / HBL-1(10) / ET(30) / LiF(1) / Al(80)

[1240] Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[1241] Within the same brackets, the percentages (97% : 3%) indicate the proportions (mass %) of compounds HT and HA in the hole injection layer, and the percentages (74% : 25% : 1%) indicate the proportions (mass %) of the third, second, and first compounds in the emissive layer. The same labeling applies below.

[1242] [Examples 2-4 and Comparative Example 1]

[1243] Except that the compound EBL-1 in Example 1 was replaced with the compound listed in the electron blocking layer column of Table 6, the organic EL elements of Examples 2 to 4 and Comparative Example 1 were prepared in the same manner as in Example 1.

[1244] [Examples 5-8 and Comparative Examples 2-3]

[1245] Except that compound EBL-1 in Example 1 was replaced with the compound listed in the electron blocking layer column of Table 6, and compound HBL-1 in Example 1 was replaced with the compound listed in the hole blocking layer column of Table 6, the organic EL elements of Examples 5 to 8 and Comparative Examples 2 to 3 were prepared in the same manner as in Example 1.

[1246] <Evaluation of Organic EL Components 1>

[1247] The fabricated organic EL elements were evaluated as follows. The measurement results are shown in Table 6.

[1248] • Drive voltage

[1249] The measurement involves applying an electric current between the anode and cathode to achieve a current density of 10 mA / cm². 2Voltage at that time (unit: V).

[1250] External quantum efficiency (EQE)

[1251] The applied voltage to the element was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation) to achieve a current density of 10 mA / cm². 2 The spectroscopic emission brightness spectrum at that time was obtained. Based on the obtained spectroscopic emission brightness spectrum, it was assumed that Lambertian emission occurred, and the external quantum efficiency EQE (in %) was calculated.

[1252] CIE1931 chromaticity

[1253] The voltage applied to the element was measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta) to achieve a current density of 10 mA / cm². 2 The CIE1931 chromaticity coordinates (x, y) at that time.

[1254] Table 6

[1255]

[1256] Compared with the organic EL device of Comparative Example 1, which has an electron blocking layer containing compound EBL-C1, the organic EL devices of Examples 1-4 have lower driving voltages and improved external quantum efficiency (EQE).

[1257] Compared with the organic EL device of Comparative Example 2, which has an electron blocking layer containing compound EBL-C1, the organic EL devices of Examples 5 and 6 have lower driving voltages and improved external quantum efficiency (EQE).

[1258] Compared with the organic EL device of Comparative Example 3, which has an electron blocking layer containing compound EBL-C1, the organic EL devices of Examples 7 and 8 have lower driving voltages and improved external quantum efficiency (EQE).

[1259] <Fabrication of Organic EL Components 2>

[1260] [Example 9]

[1261] A glass substrate (manufactured by Geoma Technology Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130nm.

[1262] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compounds HT and HA were co-deposited onto the side with the transparent electrode lines, forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[1263] Next, compound HT is deposited on the hole injection layer to form a hole transport layer with a thickness of 110 nm.

[1264] Next, compound EBL-1 is deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm as the first layer.

[1265] Next, a light-emitting layer with a thickness of 25 nm was formed by co-depositing the first fluorescent compound GD, the second delayed fluorescent compound TADF-2, and the third compound mCBP onto the electron blocking layer. The concentrations of compound GD, TADF-2, and mCBP in the light-emitting layer were set to 1% by mass, 25% by mass, and 74% by mass.

[1266] Next, compound HBL-1 is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 5 nm as the second layer.

[1267] Next, the compound ET is deposited on the hole blocking layer to form an electron transport layer with a thickness of 50 nm.

[1268] Next, lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1269] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1270] If the component configuration of the organic EL element of Example 9 is shown in a simplified manner, it is as follows.

[1271] ITO(130) / HT: HA(10, 97%: 3%) / HT (110) / EBL-1(10) / mCBP: TADF-2: GD (25, 74%: 25%: 1%) / HBL-1(5) / ET(50) / LiF(1) / Al(80)

[1272] Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[1273] [Example 10 and Comparative Example 4]

[1274] Except that the compound EBL-1 in Example 9 was replaced with the compound listed in the electron blocking layer column of Table 7, the organic EL elements of Example 10 and Comparative Example 4 were prepared in the same manner as in Example 9.

[1275] <Evaluation of Organic EL Components 2>

[1276] The fabricated organic EL element was evaluated in the same manner as in Example 1. The measurement results are shown in Table 7.

[1277] Table 7

[1278]

[1279] Compared with the organic EL device of Comparative Example 4, which has an electron blocking layer containing compound EBL-C2, the organic EL devices of Examples 9 and 10 have lower driving voltages and improved external quantum efficiency (EQE).

[1280] <Compound Evaluation>

[1281] The physical properties of the compounds listed in Tables 6 and 7 were measured using the following methods.

[1282] <ionization potential Ip>

[1283] The ionization potentials Ip of compounds EBL-1 to EBL-4 and compounds EBL-C1 to EBL-C2 were measured using the following method. The measurement results are shown in Tables 6 and 7.

[1284] The ionization potential Ip was measured under atmospheric conditions using a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd., "AC-3"). Specifically, light was irradiated onto the material to be measured, and the amount of electrons generated due to charge separation at that time was measured, thereby determining the ionization potential.

[1285] Delayed fluorescence of compound TADF-1

[1286] Delayed fluorescence by utilizing Figure 2 The apparatus shown is used to measure the transition PL for confirmation. The compound TADF-1 is dissolved in toluene, and to eliminate the effect of self-absorption, a dilute solution with an absorbance below 0.05 at the excitation wavelength is prepared. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[1287] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of the two spectra, according to equation (1) in Morris et al., J. Phys. Chem., 80(1976)969.

[1288] Upon excitation by pulsed light (light irradiated by a pulsed laser) at a wavelength absorbed by the compound TADF-1, there exists prompt emission (instantaneous emission) immediately observable from the excitation state and delayed emission (delayed emission) not immediately observable after excitation. In this embodiment, delayed fluorescence emission refers to the amount of delayed emission (delayed emission) being 5% or more relative to the amount of prompt emission (instantaneous emission). Specifically, the amount of prompt emission (instantaneous emission) is denoted as X. P The amount of delayed emission is denoted as X. D At that time, X D / X P The value is above 0.05.

[1289] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[1290] For compound TADF-1, it was confirmed that the amount of delayed luminescence was more than 5% relative to the amount of prompt luminescence.

[1291] Specifically, for compound TADF-1, X D / X P The value is above 0.05.

[1292] Delayed fluorescence of compound TADF-2

[1293] Except that compound TADF-2 was used instead of compound TADF-1, the delayed fluorescence of compound TADF-2 was confirmed in the same manner as described above.

[1294] For compound TADF-2, X D / X P The values ​​are all above 0.05.

[1295] Singlet energy S1

[1296] The singlet state energies S1 of compounds RD, GD, TADF-1, TADF-2, CBP, and mCBP were measured using the solution method described above. The results are shown in Table 8.

[1297] • Bandgap T at 77K 77K

[1298] The band gap T at 77 K was measured for compounds TADF-1 and TADF-2. 77K Based on this result and the value of the singlet energy S1 mentioned above, ΔST is confirmed. The band gap T, as described in the "Relationship between triplet energy and band gap at 77 [K]", is then used. 77K The measurement method was used to measure the T values ​​of compounds TADF-1 and TADF-2. 77K .

[1299] The measurement results are shown in Table 8.

[1300] • The main peak wavelength λ of the compound

[1301] The main peak wavelength λ of compounds RD and GD was measured using the following method.

[1302] The measurement results are shown in Table 8.

[1303] A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The emission spectrum of the sample was measured at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). In this embodiment, the emission spectrum was measured using a Hitachi spectrophotometer (device name: F-7000). However, the emission spectrum measurement apparatus is not limited to the apparatus used herein. In the emission spectrum, the wavelength of the peak where the emission intensity reaches its maximum is taken as the main peak wavelength λ.

[1304] Table 8

[1305]

[1306] • Explanation of Table 8

[1307] "-" indicates that no measurement was taken.

[1308] "<0.01" means that △ST is less than 0.01eV.

[1309] Explanation of reference numerals in the attached figures

[1310] 1 Organic EL element

[1311] 2 substrate

[1312] 3 Anode

[1313] 4 Cathode

[1314] 5. Light-emitting layer

[1315] 6 First layer

[1316] 7 Second layer

[1317] 10. Organic layer.

Claims

1. An organic electroluminescent element, characterized in that, have: anode; cathode; A light-emitting layer is contained between the anode and the cathode; The first layer is contained between the anode and the light-emitting layer, and is adjacent to the light-emitting layer; The second layer is contained between the cathode and the light-emitting layer, and is adjacent to the light-emitting layer. The light-emitting layer comprises a first compound, a second compound, and a third compound. The first layer comprises a compound represented by the following general formula (1). The second layer comprises a compound represented by the following general formula (2), The first compound is a fluorescent compound. The second compound is a delayed fluorescence compound. The singlet state energies S1(M1) of the first compound, S1(M2) of the second compound, and S1(M3) of the third compound satisfy the following mathematical expression (Form 1): S1(M3)>S1(M2)>S1(M1)…(Number 1) In the general formula (1), Ra1~Ra5 and Rb1~Rb5 are each independently hydrogen atoms or substituents, and Ra1~Ra5 and Rb1~Rb5 as substituents are each independently... Halogen atoms, cyano, Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or Heteroaryl groups with 5 to 30 cyclic atoms, substituted or unsubstituted. In the general formula (1), the part represented by the following general formula (1A) is a group represented by any one of the following general formulas (1A-1) to (1A-5), (1A-9) and (1A-10). In the general formula (1A), Rc1 to Rc5 are synonyms with Rc1 to Rc5 in the general formula (1), and * indicates the site where the nitrogen atom is bonded to in the compound represented by the general formula (1). In the general formulas (1A-1) to (1A-5), (1A-9), and (1A-10), R A It can be a hydrogen atom or a substituent. R as a substituent A Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5–30 cyclic atoms In the existence of multiple R A In the case of R A They are the same or different from each other, and * indicates the site where they are bonded to a nitrogen atom in a compound represented by the general formula (1). In the general formula (1), the substituent in the case of "substituted or unsubstituted" is an unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic structure, or an unsubstituted heteroaryl group with 5 to 30 cyclic atoms. In the general formula (2), X1 to X3 are each independently either nitrogen atoms or CR1, wherein two or three of X1 to X3 are nitrogen atoms. R1 is a hydrogen atom or a substituent. R1, as a substituent, is independently, Halogen atoms, cyano, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, or Unsubstituted alkyl groups having 1 to 30 carbon atoms, Ar1 and Ar2 independently, Represented by the following general formula (2A), or as Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or Heteroaryl groups with 5 to 30 cyclic atoms, substituted or unsubstituted. A is represented by the following general formula (2A), In the general formula (2A), HAr is represented by the following general formula (2B), a is 1 or 2. When a is 1, L1 is a single bond or a divalent linker. When a is 2, L1 is a trivalent linker. Multiple HArs may be the same as or different from each other. The linking group is, Derived from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or Groups derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted. Furthermore, the groups formed by mutual bonding may be the same or different from each other. In the general formula (2B), X 11 ~X 18 Each is independently a nitrogen atom, CR 13 Or bonded to the carbon atom of L1, Multiple R 13 Whether they are the same or different, Y1 represents oxygen atoms, sulfur atoms, and NR. 18 CR 14 R 15 Nitrogen atoms bonded to L1, or bonded to R respectively 17 And the carbon atoms of L1, Among them, X is bonded to L1. 11 ~X 18 and R 14 ~R 15 The carbon atom in Y1, the nitrogen atom in Y1, and any one of the carbon atoms, R 14 and R 15 Same or different, R 18 and R 13 ~R 15 R 17 Each is independently a hydrogen atom or a substituent, or R 14 and R 15 The groups bond together to form a ring. R as a substituent 18 and R 13 ~R 15 R 17 Each independently, Halogen atoms, cyano, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heteroaryl groups with 5–30 cyclic atoms Unsubstituted alkyl groups having 1 to 30 carbon atoms, or Unsubstituted alkoxy groups with 1 to 30 carbon atoms, In the general formula (2), the substituent in the case of "substituted or unsubstituted" is an unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic structure, or an unsubstituted heteroaryl group with 5 to 30 cyclic atoms. The ionization potential Ip of the compound represented by the general formula (1) is 5.78 eV or higher.

2. The organic electroluminescent element as described in claim 1, characterized in that, R A It is a hydrogen atom.

3. The organic electroluminescent element as described in claim 1, characterized in that, The group represented by the general formula (1A) is any one of the general formulas (1A-1) to (1A-5) and (1A-10).

4. The organic electroluminescent element as described in claim 1, characterized in that, The group represented by the general formula (1A) is the same group represented by the general formula (1A-1) or (1A-4).

5. The organic electroluminescent element as described in claim 1, characterized in that, The group represented by the general formula (1A) is the same group represented by the general formula (1A-9).

6. The organic electroluminescent element as described in claim 1, characterized in that, The group represented by the general formula (1A) is the same group represented by the general formula (1A-1), (1A-4) or (1A-9).

7. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, Ra1 to Ra5 ​​and Rb1 to Rb5 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms.

8. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, Ra1 to Ra5 ​​are each independently a hydrogen atom, or a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure. Rb1 to Rb5 are each independently a hydrogen atom, or a heteroaryl group consisting of 5 to 30 substituted or unsubstituted cyclic atoms.

9. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, Ra1 to Ra5 ​​are either independently hydrogen atoms or aryl groups with 6 to 30 carbon atoms obtained by substitution with heteroaryl groups having 5 to 30 cyclic atoms. Rb1 to Rb5 are each independently a hydrogen atom, or a heteroaryl group consisting of 5 to 30 substituted or unsubstituted cyclic atoms.

10. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, Ra1 to Ra5 ​​and Rb1 to Rb5 are each independently hydrogen atoms, or heteroaryl groups with 5 to 30 substituted or unsubstituted cyclic atoms.

11. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, One of Ra1 to Ra5 ​​is a substituent, and the remaining Ra1 to Ra5 ​​atoms are hydrogen atoms, not those with the substituent. One of Rb1 to Rb5 is a substituent, and the remaining Rb1 to Rb5 atoms are hydrogen atoms, not those with a substituent. Rc3 to Rc5 are hydrogen atoms.

12. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, The substituents Ra1 to Ra5 ​​and Rb1 to Rb5 are each independently, Halogen atoms, cyano, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5 to 30 cyclic atoms.

13. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, One of Ra1 to Ra5 ​​is a substituent, and the remaining Ra1 to Ra5 ​​atoms are hydrogen atoms, not those with the substituent. One of Rb1 to Rb5 is a substituent, and the remaining Rb1 to Rb5 atoms are hydrogen atoms, not those with a substituent. Rc3 to Rc5 are hydrogen atoms. The substituents Ra1 to Ra5 ​​and Rb1 to Rb5 are each independently, Halogen atoms, cyano, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5 to 30 cyclic atoms.

14. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, At least one of Ra1 to Ra5 ​​is independently a group represented by any one of the following general formulas (1B-1) to (1B-10), and at least one of Rb1 to Rb5 is independently a group represented by any one of the following general formulas (1B-1) to (1B-10). In the general formulas (1B-1) to (1B-10), R B It can be a hydrogen atom or a substituent. R as a substituent B Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5–30 cyclic atoms, in the presence of multiple R B In the case of R B If they are the same or different, * indicates the bonding site of the benzene rings that are bonded to Ra1~Ra5 and Rb1~Rb5 in the compound represented by general formula (1), respectively.

15. The organic electroluminescent element as described in claim 14, characterized in that, R B It is a hydrogen atom.

16. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, When one or more of Ra1 to Ra5 ​​are unsubstituted dibenzofuran groups, none of Rb1 to Rb5 and Rc3 to Rc5 are unsubstituted dibenzofuran groups.

17. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, In the case where one or more of Ra1 to Ra5 ​​are substituted or unsubstituted dibenzofuran groups, none of Rb1 to Rb5 are substituted or unsubstituted dibenzofuran groups, and none of Rc3 to Rc5 are unsubstituted dibenzofuran groups. In the case where one or more of Rb1 to Rb5 are substituted or unsubstituted dibenzofuran groups, none of Ra1 to Ra5 ​​are substituted or unsubstituted dibenzofuran groups, and none of Rc3 to Rc5 are unsubstituted dibenzofuran groups. In the case where one or more of Rc3 to Rc5 are unsubstituted dibenzofuran groups, neither Ra1 to Ra5 ​​nor Rb1 to Rb5 are substituted or unsubstituted dibenzofuran groups.

18. The organic electroluminescent element as claimed in claim 1, characterized in that, The compound represented by the general formula (1) is a compound represented by the following general formula (1X), the following general formula (1Y) or the following general formula (1Z). In the general formulas (1X), (1Y), and (1Z), at least one of Ra1 to Ra5 ​​is independently a group represented by any one of the following general formulas (1B-1) to (1B-10), and at least one of Rb1 to Rb5 is independently a group represented by any one of the following general formulas (1B-1) to (1B-10). A R is a hydrogen atom or a substituent. A Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5–30 cyclic atoms In the existence of multiple R A In the case of R A Whether they are the same or different, In the general formulas (1B-1) to (1B-10), R B R is a hydrogen atom or a substituent. B Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted heteroaryl groups with 5–30 cyclic atoms, in the presence of multiple R B In the case of R B They are the same or different from each other. * indicates the bonding site of the benzene rings that are bonded to Ra1 to Ra5 ​​and Rb1 to Rb5 in the compound represented by general formula (1X), general formula (1Y) or general formula (1Z).

19. The organic electroluminescent element as described in claim 18, characterized in that, In the general formulas (1X), (1Y), and (1Z), one of Ra1 to Ra5 ​​is a group represented by any one of the general formulas (1B-1) to (1B-10), and one of Rb1 to Rb5 is a group represented by any one of the general formulas (1B-1) to (1B-10).

20. The organic electroluminescent element as described in claim 18 or 19, characterized in that, R A It is a hydrogen atom.

21. The organic electroluminescent element as described in claim 18 or 19, characterized in that, R B It is a hydrogen atom.

22. The organic electroluminescent element as claimed in claim 1, characterized in that, The ionization potential Ip of the compound represented by the general formula (1) is 5.80 eV or higher.

23. The organic electroluminescent element as described in claim 1, characterized in that, The ionization potential Ip of the compound represented by the general formula (1) is 5.85 eV or higher.

24. The organic electroluminescent element according to any one of claims 1, 22, and 23, characterized in that, Using a photoelectron spectrometer in the atmosphere, light is irradiated onto the material to be measured, and the amount of electrons generated due to charge separation at this time is measured, thereby measuring the ionization potential Ip.

25. The organic electroluminescent element as described in claim 1, characterized in that, The compound represented by the general formula (1) is any one of the following compounds.

26. The organic electroluminescent element as described in claim 1, characterized in that, When two of X1 to X3 are nitrogen atoms, X1 and X2 are nitrogen atoms, and X3 is CR1.

27. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2), X1 and X2 are nitrogen atoms, X3 is CR1, and R1 is a hydrogen atom.

28. The organic electroluminescent element as claimed in claim 1, characterized in that, L1, as a linking group, is a divalent or trivalent residue derived from an aryl group with 6 to 30 cyclic carbons, whether substituted or unsubstituted.

29. The organic electroluminescent element as claimed in claim 1, characterized in that, L1, as a linking group, is a trivalent residue derived from an aryl group with 6 to 30 cyclic carbons, either substituted or unsubstituted.

30. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2A), when a is 1, L1 is a divalent linking group; when a is 2, L1 is a trivalent linking group.

31. The organic electroluminescent element as described in claim 30, characterized in that, When a is 1, L1 is a divalent linker, and the general formula (2A) is represented by the following general formula (2A-1). When a is 2, L1 is a trivalent linker, and the general formula (2A) is represented by the following general formula (2A-2). Whether HAr is the same or different... (HAr)-L1- (2A-1) In the general formulas (2A-1) and (2A-2), L1 is a divalent or trivalent linking group, and the linking group is... Derived from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or A group derived from a heteroaryl group, either substituted or unsubstituted, having 5 to 30 cyclic atoms.

32. The organic electroluminescent element as described in claim 30 or 31, characterized in that, L1 is a divalent or trivalent linking group derived from any one of benzene, biphenyl, terphenyl, naphthalene, and phenanthrene.

33. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2A), a is 1, and L1 is a linking group. L1, as a linking group, is... Divalent residues derived from substituted or unsubstituted aryl groups having 6 to 30 cyclic carbons, or Divalent residues derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted.

34. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2A), a is 2, and L1 is a linking group. L1, as a linking group, is... Trivalent residues derived from substituted or unsubstituted aryl groups with 6 to 30 cyclic carbons, or Trivalent residues derived from heteroaryl groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted.

35. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2A), L1 is a single bond.

36. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), Y1 represents an oxygen atom, a sulfur atom, or a CR atom. 14 R 15 NR 18 Or it may be a nitrogen atom bonded to L1.

37. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), Y1 is CR 14 R 15 .

38. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), Y1 is an oxygen atom or a sulfur atom.

39. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), Y1 is NR. 18 Or it may be a nitrogen atom bonded to L1.

40. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2B), Y1 is NR 18 In the case of X 11 ~X 18 One of them is a carbon atom bonded to L1, and the other X 11 ~X 18 Nitrogen atom or CR 13 .

41. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2B), when Y1 is a nitrogen atom bonded to L1, X 11 ~X 18 Each is independently a nitrogen atom or CR 13 .

42. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), Y1 is an oxygen atom or a sulfur atom. X 11 ~X 18 One of them is a carbon atom bonded to L1, and the others are CR. 13 .

43. The organic electroluminescent element as described in claim 1, characterized in that, In the general formula (2B), X 13 Or X 16 The carbon atom is bonded to L1.

44. The organic electroluminescent element as claimed in claim 1, characterized in that, In the general formula (2B), Y1 is an oxygen atom, X 11 and X 18 For CR 13 X 12 ~X 17 One of them is a carbon atom bonded to L1, and the others are CR. 13 .

45. The organic electroluminescent element as claimed in claim 1, characterized in that, The compound represented by the general formula (2) is any one of the following compounds, 46. ​​The organic electroluminescent element as described in claim 1, characterized in that, The first compound is either a compound with delayed fluorescence or a compound that does not exhibit delayed fluorescence.

47. The organic electroluminescent element as claimed in claim 1, characterized in that, The first compound is a fluorescent material, wherein the fluorescent material is a diarylaminonaphthalene derivative, an aryl-substituted naphthalene derivative, a diarylaminoanthracene derivative, an aryl-substituted anthracene derivative, a diarylaminopyrene derivative, an aryl-substituted pyrene derivative, or a diarylamino Derivatives, aryl substitution Derivatives, diarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indene-perylene derivatives, acenaphthene-fluoranthene derivatives, pyrrole methylene boron complexes, compounds with a pyrrole methylene skeleton, metal complexes of compounds with a pyrrole methylene skeleton, diketopyrrole-pyrrole derivatives, perylene derivatives, or tetraphenyl derivatives.

48. The organic electroluminescent element as described in claim 1, characterized in that, The first compound is a compound represented by the following general formula (30), the following general formula (40), the following general formula (50), the following general formula (I), or the following general formula (60). General formula (30) satisfies any one of the following (1) to (4): (1)X1~X 20 At least four of them are independently straight-chain or branched alkoxy groups with 1 to 6 carbon atoms, and the rest are hydrogen atoms; (2)X1~X 20 At least one of them is a straight-chain or branched alkyl group having 1 to 6 carbon atoms, at least one of them is a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, the total number of the alkyl group and the alkoxy group is 4 or more, and the remainder is hydrogen. (3)X1~X 20 At least six of them are independently straight-chain or branched alkyl groups having 1 to 6 carbon atoms, and the rest are hydrogen atoms; (4)X1~X 20 At least four of the molecules are independently straight-chain or branched alkyl groups having 1 to 6 carbon atoms, two of which have 3 to 6 carbon atoms, and the remainder are hydrogen atoms. In general formula (40), R1 to R4 are each independently a hydrogen atom or a substituent, and R1 to R4 as substituents are each independently derived from... Halogen atoms, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and Choose from the group consisting of substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms. In general formula (50), A 1 ~A 2 Each of the following groups independently represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group with 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group with 1 to 10 carbon atoms, or a halogen atom, where p and q are integers from 1 to 5, and s are integers from 1 to 9. When p and q are 2 or more, multiple A groups... 1 A 2 Each element, whether identical or different, can connect to form a saturated or unsaturated cycle, wherein there is no A. 1 And A 2 The case where both are hydrogen atoms, R 1 This indicates a substituted or unsubstituted alkyl group with 3 to 10 carbon atoms, representing a secondary or tertiary alkyl group, where t is an integer from 1 to 9. In cases where t is 2 or more, multiple R... 1 Same or different, R 2 This refers to a hydrogen atom, an alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 20 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an aromatic amino group with 6 to 50 substituted or unsubstituted carbon atoms, an alkylamino group with 1 to 10 substituted or unsubstituted carbon atoms, or a halogen atom, where u is an integer from 0 to 8. When u is 2 or higher, multiple R... 2 Whether they are the same or different, s+t+u are integers from 2 to 10. In general formula (I), R represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a cyano group, or a halogen atom, and k is an integer from 1 to 9. When k is 2 or more, multiple Rs may be the same or different from each other. A 1 And A 2 Each of the following groups independently represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 50 carbon atoms, a substituted or unsubstituted aroxy group with 6 to 50 carbon atoms, a substituted or unsubstituted arylamino group with 6 to 50 carbon atoms, a substituted or unsubstituted alkylamino group with 1 to 20 carbon atoms, a cyano group, or a halogen atom, where m and n are integers from 0 to 5. When m is 2 or more, multiple A groups... 1 Multiple A's, whether identical or different, can connect to form saturated or unsaturated loops when n is 2 or more. 2 They may be the same or different from each other, and can connect to form saturated or unsaturated rings. Among them, A 1 And A 2 At least one of them has any one of the following groups: substituted or unsubstituted alkyl group having 2 or more carbon atoms, substituted or unsubstituted aralkyl group having 7 or more carbon atoms, substituted or unsubstituted cycloalkyl group having 3 or more carbon atoms, substituted or unsubstituted alkoxy group having 2 or more carbon atoms, and substituted or unsubstituted alkylamino group having 2 or more carbon atoms. For any integer p between 1 and 9, when p is 2 or greater, multiple () p The groups within the group may be the same or different from each other, and k+p is an integer less than 10. In the general formula (60), The Za ring, Zb ring, and Zc ring are each independently derived from... Substituted or unsubstituted aromatic rings with 6 to 30 carbon atoms, and Heteroaromatic rings with 5 to 30 cyclic atoms, substituted or unsubstituted The selected ring structure in the group. X 21 and X 22 Each of the following can be independently an oxygen atom, NRa, or a sulfur atom, wherein NRa is a nitrogen atom with a substituent Ra. In X 21 In the case of NRa, Ra may bond with a Za ring or a Zb ring to form a ring, or it may not form a ring. In X 22 In the case of NRa, Ra may bond with a Za ring or a Zc ring to form a ring, or it may not form a ring. Ra is independently derived from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, and Alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted The groups selected from the group that constitute the composition, Y 21 It can be any one of boron atom, phosphorus atom, SiRb, P=O, and P=S, where SiRb is a silicon atom with the substituent Rb. Rb is independently derived from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms, and Alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted The groups selected from the group that constitutes the composition.

49. The organic electroluminescent element as described in claim 48, characterized in that, The compound represented by the general formula (30) is any one of the following compounds.

50. The organic electroluminescent element as described in claim 48, characterized in that, The compound represented by the general formula (40) is any one of the following compounds.

51. The organic electroluminescent element as described in claim 48, characterized in that, The compound represented by the general formula (50) is any one of the following compounds.

52. The organic electroluminescent element as described in claim 48, characterized in that, The compound represented by the general formula (I) is any one of the following compounds.

53. The organic electroluminescent element as described in claim 48, characterized in that, The compound represented by the general formula (60) is any one of the following compounds, 54. The organic electroluminescent element as described in claim 1, characterized in that, The second compound is not a phosphorescent metal complex.

55. The organic electroluminescent element as claimed in claim 1, characterized in that, The second compound is not a metal complex.

56. The organic electroluminescent element as described in claim 1, characterized in that, The second compound is a compound represented by the following general formula (2). In the general formula (2), A is the acceptor site, i.e., the electron-accepting site, which is a group with a local structure selected from the following general formulas (a-1) to (a-7). When multiple A's are present, the multiple A's may be the same or different from each other, and the A's can bond with each other to form saturated or unsaturated rings. B is a donor site, i.e., an electron-donating site, with a local structure selected from the following general formulas (b-1) to (b-6). When multiple Bs are present, they may be the same or different from each other, and they can bond together to form saturated or unsaturated rings. a, b, and d can be independently 1, 2, 3, 4, or 5. c can be 0, 1, 2, 3, 4, or 5. When c is 0, A and B are bonded by single bonds or spiral bonds. When c is 1, 2, 3, 4, or 5, L is from Substituted or unsubstituted aromatic hydrocarbon groups with 6 to 30 carbon atoms, and The linking group selected from the group consisting of substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, where multiple L groups are present, are identical or different from each other, and the L groups can bond together to form saturated or unsaturated rings. In the general formulas (b-1) to (b-6), R can be either a hydrogen atom or a substituent, where R is a substituent and the substituent is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted. Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, and It is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, wherein, in the presence of multiple Rs, the multiple Rs are the same or different from each other, and the Rs are able to bond with each other to form saturated or unsaturated rings.

57. The organic electroluminescent element as described in claim 56, characterized in that, The bonding states of compounds represented by the general formula (2) are those indicated by No. (1A), (1B), (1C), (1D), (1E), (1F), (1G), or (1H) below.

58. The organic electroluminescent element as claimed in claim 1, characterized in that, The second compound has a local structure represented by the following general formula (200) and a local structure represented by the following general formula (2Y) in one molecule. In the general formula (200), CN is a cyano group. n is an integer greater than or equal to 1. Z1 to Z6 are each independently a nitrogen atom, a carbon atom bonded to CN, or a carbon atom bonded to other atoms in the molecule of the second compound. In the case where Z1 is a carbon atom bonded to CN, at least one of the remaining five, namely Z2 to Z6, is a carbon atom bonded to other atoms in the molecule of the second compound. These other atoms are either atoms constituting a local structure represented by the following general formula (2Y), or atoms constituting a linking group or substituent between these local structures. In the general formula (2Y), F and G independently represent the ring structure. m is 0 or 1 When m is 1, Y 20 It represents a single bond, oxygen atom, sulfur atom, selenium atom, carbon atom, silicon atom, or germanium atom.

59. The organic electroluminescent element as described in claim 58, characterized in that, When m is 0 in the general formula (2Y), the general formula (2Y) is represented by the following general formula (20Y). When m is 1 in the general formula (2Y), the general formula (2Y) is represented by any one of the following general formulas (22) to (28). The ring structure F and ring structure G in the general formula (20Y) are synonyms with the ring structure F and ring structure G in the general formula (2Y). The ring structure F and ring structure G in general formulas (22) to (28) are synonyms with the ring structure F and ring structure G in general formula (2Y).

60. The organic electroluminescent element as described in claim 59, characterized in that, The ring structure F and the ring structure G are 5-membered rings or 6-membered rings, and the 5-membered rings or 6-membered rings are unsaturated rings.

61. The organic electroluminescent element as described in claim 58, characterized in that, The second compound is a compound represented by the following general formula (20). In the general formula (20), A is represented by the general formula (200), wherein, in the general formula (200), CN is a cyano group, n is an integer greater than or equal to 1, and Z1 to Z6 are independently a nitrogen atom, a carbon atom bonded to CN, a carbon atom bonded to R, a carbon atom bonded to L, or a carbon atom bonded to D, respectively, and among Z1 to Z6, at least one carbon atom is bonded to CN, and at least one carbon atom is bonded to L or D. Each R is independently a hydrogen atom or a substituent, wherein the substituent in R is selected from the group consisting of a halogen atom, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, an aromatic heterocyclic group with 5 to 30 substituted or unsubstituted alkyl group with 1 to 30 substituted or unsubstituted alkylsilyl group with 3 to 30 substituted or unsubstituted arylsilyl group with 6 to 60 substituted or unsubstituted alkoxy group with 1 to 30 substituted or unsubstituted aryloxy group with 6 to 30 substituted or unsubstituted alkylamino group with 2 to 30 substituted or unsubstituted arylamino group with 6 to 60 substituted or unsubstituted alkylthio group with 1 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted or unsubstituted arylthio group with 6 to 30 substituted. D is represented by the general formula (2Y), wherein the ring structure F and the ring structure G in the general formula (2Y) are unsubstituted or have substituents, and m is 0 or 1. When m is 1, Y 20 Represents single bonds, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, and CR. 21 R 22 SiR 23 R 24 Or GeR 25 R 26 R 21 ~R 26 Synonymous with the group exemplified by R, and furthermore, when m is 1 in the general formula (2Y), the general formula (2Y) is represented by any one of the following general formulas (22) to (25) and the following general formulas (21Y) to (24Y). The ring structure F and ring structure G in general formulas (22) to (25) and general formulas (21Y) to (24Y) are synonymous with the ring structure F and ring structure G in general formula (2Y).

62. The organic electroluminescent element as described in claim 61, characterized in that, In the general formula (20), (i) When L is between A and D L is a single bond, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms in the cyclic ring, or a substituted or unsubstituted aromatic heterocyclic group with 5 to 14 cyclic atoms; CR 81 R 82 NR 83 O, S, SiR 84 R 85 CR 86 R 87 -CR 88 R 89 CR 90 =CR 91 Substituted or unsubstituted aliphatic hydrocarbon cyclic groups, or substituted or unsubstituted aliphatic heterocyclic groups, The R 81 ~R 91 Each is independently synonymous with the aforementioned R. In the general formula (20), (ii) In the case that L is located at the end of the molecule of the second compound, L is synonymous with R. In the general formula (20), f is an integer greater than or equal to 1. e and g are each an independent integer greater than or equal to 0. Multiple A's may be the same or different from each other. Multiple Ds may be the same or different from each other. Multiple L's may be the same as or different from each other.

63. The organic electroluminescent element as described in claim 61 or 62, characterized in that, The general formula (20) is represented by any one of the following general formula numbers (201) to (220).

64. The organic electroluminescent element as described in claim 58, characterized in that, The general formula (2Y) is represented by at least one of the following general formulas (2a) and (2x). In the general formula (2x), A and B independently represent the ring structure represented by the general formula (2c) or the ring structure represented by the general formula (2d) below. Ring structure A and ring structure B are fused with adjacent ring structures at any position. px and py are independent integers of 0 to 4, representing the number of ring structures A and ring structures B respectively. When px is an integer of 2 to 4, multiple ring structures A are the same or different from each other. When py is an integer of 2 to 4, multiple ring structures B are the same or different from each other. In the general formula (2d), Z7 represents a carbon atom, a nitrogen atom, a sulfur atom, or an oxygen atom.

65. The organic electroluminescent element as described in claim 64, characterized in that, In the general formula (2x), when px is 0 and py is c, it is represented by the following general formula (2b). In the general formula (2b), c is an integer greater than or less than 1 and less than 4. When c is an integer greater than or less than 2 and less than 4, multiple ring structures E are the same or different from each other. In the general formula (2b), E represents a ring structure represented by the general formula (2c) or a ring structure represented by the general formula (2d). The ring structure E is fused with the adjacent ring structure at any position.

66. The organic electroluminescent element as described in claim 58, characterized in that, The second compound has a structure in its molecule represented by the following general formula (2e). In the general formula (2e), R1 to R9 are each independently a hydrogen atom, a substituent, or a single bond bonded to other atoms in the molecule of the second compound. The substituents in R1 to R9 are selected from the group consisting of halogen atoms, substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted aromatic heterocyclic groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted alkylamino groups with 2 to 30 cyclic carbon atoms, substituted or unsubstituted arylamino groups with 6 to 60 cyclic carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 30 cyclic carbon atoms, and substituted or unsubstituted arylthio groups with 6 to 30 cyclic carbon atoms, wherein at least one of R1 to R9 is a single bond bonded to other atoms in the molecule of the second compound. In the general formula (2e), at least one group of the substituents selected from R1 to R9 can bond with each other to form a ring structure. In the general formula (2e), at least one group of the combinations of substituents consisting of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, and R9 and R1 can bond with each other to form a ring structure.

67. The organic electroluminescent element as described in claim 58, characterized in that, The second compound has a structure in its molecule represented by the following general formula (2y). R in the general formula (2y) 11 ~R 19 Each of the following is a single bond that is independently a hydrogen atom, a substituent, or bonded to other atoms in the molecule of the second compound. The R 11 ~R 19 The substituents in the group are selected from the group consisting of a halogen atom, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, a substituted or unsubstituted aromatic heterocyclic group with 5 to 30 cyclic carbon atoms, a substituted or unsubstituted alkyl group with 1 to 30 cyclic carbon atoms, a substituted or unsubstituted alkylsilyl group with 3 to 30 cyclic carbon atoms, a substituted or unsubstituted arylsilyl group with 6 to 60 cyclic carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 30 cyclic carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 30 cyclic carbon atoms, a substituted or unsubstituted alkylamino group with 2 to 30 cyclic carbon atoms, a substituted or unsubstituted arylamino group with 6 to 60 cyclic carbon atoms, a substituted or unsubstituted alkylthio group with 1 to 30 cyclic carbon atoms, and a substituted or unsubstituted arylthio group with 6 to 30 cyclic carbon atoms. Wherein, R 11 ~R 19 At least one of them is a single bond bonded to other atoms in the molecule of the second compound, in the general formula (2y), from R 11 ~R 19 At least one combination of the selected substituents can bond to each other to form a ring structure. In the general formula (2y), A and B independently represent the ring structure represented by the following general formula (2g) or the ring structure represented by the following general formula (2h). Ring structures A and B are fused with adjacent ring structures at arbitrary positions. px is the number of ring structures A, which is an integer from 0 to 4. When px is an integer from 2 to 4, multiple ring structures A are the same or different from each other. When py is an integer from 2 to 4, multiple ring structures B are the same or different from each other. py is the number of ring structures B, which is an integer from 0 to 4. In the general formula (2g), R 201 and R 202 Independently with the R 11 ~R 19 Synonyms, R 201 and R 202 They can bond together to form a ring structure, R 201 and R 202 Each atom is bonded to a carbon atom forming a 6-membered ring of the general formula (2g). In the general formula (2h), Z8 represents CR 203 R 204 NR 205 sulfur atoms or oxygen atoms, R 203 ~R 205 Independently with the R 11 ~R 19 Synonyms In the general formula (2y), from R 11 ~R 19 R 201 ~R 205 At least one of the selected substituents can bond with each other to form a ring structure.

68. The organic electroluminescent element as described in claim 67, characterized in that, In the general formula (2y), when px is 0 and py is c, it is represented by the following general formula (2f). R in the general formula (2f) 11 ~R 19 Each of the following is a single bond that is independently a hydrogen atom, a substituent, or bonded to other atoms in the molecule of the second compound. The R 11 ~R 19 The substituents in the group are selected from the group consisting of a halogen atom, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, a substituted or unsubstituted aromatic heterocyclic group with 5 to 30 cyclic carbon atoms, a substituted or unsubstituted alkyl group with 1 to 30 cyclic carbon atoms, a substituted or unsubstituted alkylsilyl group with 3 to 30 cyclic carbon atoms, a substituted or unsubstituted arylsilyl group with 6 to 60 cyclic carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 30 cyclic carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 30 cyclic carbon atoms, a substituted or unsubstituted alkylamino group with 2 to 30 cyclic carbon atoms, a substituted or unsubstituted arylamino group with 6 to 60 cyclic carbon atoms, a substituted or unsubstituted alkylthio group with 1 to 30 cyclic carbon atoms, and a substituted or unsubstituted arylthio group with 6 to 30 cyclic carbon atoms. Wherein, R 11 ~R 19 At least one of them is a single bond bonded to other atoms in the molecule of the second compound, in the general formula (2f), from R 11 ~R 19 At least one combination of the selected substituents can bond to each other to form a ring structure. In the general formula (2f), E represents a ring structure represented by the following general formula (2g) or a ring structure represented by the following general formula (2h), wherein the ring structure E is fused with adjacent ring structures at any position, and c is the number of ring structures E, which is an integer of 1 to 4. When c is an integer of 2 to 4, the multiple ring structures E may be the same or different from each other. In the general formula (2g), R 201 and R 202 Independently with the R 11 ~R 19 Synonyms, R 201 and R 202 They can bond together to form a ring structure, R 201 and R 202 Each atom is bonded to a carbon atom forming a 6-membered ring of the general formula (2g). In the general formula (2h), Z8 represents CR 203 R 204 NR 205 sulfur atoms or oxygen atoms, R 203 ~R 205 Independently with the R 11 ~R 19 Synonyms In the general formula (2f), from R 11 ~R 19 R 201 ~R 205 At least one of the selected substituents can bond with each other to form a ring structure.

69. The organic electroluminescent element as described in claim 58, characterized in that, The second compound is represented by the following general formula (2A). In the general formula (2A), n is an integer greater than or equal to 1, t is an integer greater than or equal to 1, u is an integer greater than or equal to 0, and L A The ring is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 30 carbon atoms or an aromatic heterocycle with 6 to 30 cyclic atoms, CN is a cyano group, D1 and D2 are independently represented by the general formula (2Y), wherein the ring structure F and ring structure G in the general formula (2Y) are unsubstituted or have substituents, m is 0 or 1, and when m is 1, Y 20 Represents single bonds, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, and CR. 21 R 22 SiR 23 R 24 Or GeR 25 R 26 R 21 ~R 26 Each R is independently a hydrogen atom or a substituent. 21 ~R 26 The substituents in the group are halogen atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms in the ring, substituted or unsubstituted aromatic heterocyclic groups with 5 to 30 carbon atoms in the ring, substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms in the ring, substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms in the ring, substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms in the ring, substituted or unsubstituted alkoxy groups with 1 to 30 carbon atoms in the ring, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the ring, substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms in the ring, and substituted... The substituent selected from the group consisting of an unsubstituted arylamino group having 6 to 60 cyclic carbons, a substituted or unsubstituted alkylthio group having 1 to 30 cyclic carbons, and a substituted or unsubstituted arylthio group having 6 to 30 cyclic carbons, wherein when m is 1, the general formula (2Y) is represented by any one of the following general formulas (22) to (25) and the following general formulas (21Y) to (24Y), where D1 and D2 are the same or different, when t is 2 or more, multiple D1s are the same or different from each other, and when u is 2 or more, multiple D2s are the same or different from each other. The ring structure F and ring structure G in general formulas (22) to (25) and general formulas (21Y) to (24Y) are synonymous with the ring structure F and ring structure G in general formula (2Y).

70. The organic electroluminescent element as described in claim 69, characterized in that, The L A Aromatic hydrocarbon rings with 6 to 14 carbon atoms, either substituted or unsubstituted.

71. The organic electroluminescent element as described in claim 69 or 70, characterized in that, The L A It can be pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthrene, benzofuran, or dibenzofuran.

72. The organic electroluminescent element as claimed in claim 1, characterized in that, The second compound is represented by the following general formula (21), In the general formula (21), A 21 And B 21 Each can be independently represented as a substituted or unsubstituted aromatic hydrocarbon group with 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 5 to 30 carbon atoms. X 21 ~X 28 and Y 21 ~Y 28 Each independently represents a nitrogen atom, and R D Bonded carbon atoms or with L 23 Bonded carbon atoms, where X 25 ~X 28 At least one of them is with L 23 Bonded carbon atoms, Y 21 ~Y 24 At least one of them is with L 23 Bonded carbon atoms, R D Each R can be an independent hydrogen atom or a substituent. D The substituents are selected from the group consisting of halogen atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 5 to 30 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted silyl groups. L 21 and L 22 Each is an independent single bond or linking group, as L 21 and L 22 The linking group is: a substituted or unsubstituted aromatic hydrocarbon group with 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 cyclic atoms, a multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group, a multiple linking group formed by bonding 2 to 4 groups selected from the heterocyclic group, or a multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group. L 23 This indicates a monocyclic hydrocarbon group with 6 or fewer cyclic carbon atoms, whether substituted or unsubstituted, or a monocyclic heterocyclic group with 6 or fewer cyclic atoms. w represents an integer from 0 to 3. When w is 0, X 25 ~X 28 At least one of them is related to Y 21 ~Y 24 At least one of them is directly bonded. Monocyclic hydrocarbon groups are not fused rings, but groups derived from a single hydrocarbon ring, namely aliphatic cyclic hydrocarbons or aromatic hydrocarbons. Monocyclic heterocyclic groups are groups derived from a single heterocycle.

73. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), at least one of the following conditions (i) and (ii) must be satisfied: (i)A 21 And B 21 At least one of them is an aromatic hydrocarbon group with 6 to 30 cyclic carbons obtained by substituted cyano or an aromatic heterocyclic group with 6 to 30 cyclic atoms obtained by substituted cyano; (ii)X 21 ~X 24 and Y 25 ~Y 28 At least one of them is related to R D The bonded carbon atom, the R D At least one of them is an aromatic hydrocarbon group with 6 to 30 cyclic carbons obtained by substituted cyano group or an aromatic heterocyclic group with 6 to 30 cyclic atoms obtained by substituted cyano group. Among them, there are multiple R D In the case of multiple R D They are the same or different.

74. The organic electroluminescent element as described in claim 72 or 73, characterized in that, In the general formula (21), when A is used 21 And B 21 When the aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 6 to 30 carbon atoms has a substituent, the substituent is one or more groups selected from the group consisting of a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, and a heterocyclic group having 5 to 30 carbon atoms, as described in A. 21 And B 21 In the case of multiple substituents, the substituents may be the same or different from each other.

75. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), A 21 And B 21 At least one of them is, Phenyl groups obtained by cyano substitution Naphthyl groups obtained by cyano substitution phenanthrene obtained by cyano substitution, Dibenzofuranyl, obtained by cyano substitution dibenzothiophene group obtained by cyano substitution, Biphenyl obtained by cyano substitution, Triphenyl groups obtained by cyano substitution 9,9-diphenylfluorenyl, obtained by cyano substitution, 9,9'-spirobis[9H-fluorene]-2-yl obtained by cyano substitution, 9,9-dimethylfluorenyl obtained by substitution with cyano, or Triphenylene oxide obtained by substituted cyano group.

76. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), X 21 ~X 24 and Y 25 ~Y 28 At least one of them is CR D X 21 ~X 24 and Y 25 ~Y 28 R in D At least one of them is, Phenyl groups obtained by cyano substitution Naphthyl groups obtained by cyano substitution phenanthrene obtained by cyano substitution, Dibenzofuranyl, obtained by cyano substitution dibenzothiophene group obtained by cyano substitution, Biphenyl obtained by cyano substitution, Triphenyl groups obtained by cyano substitution 9,9-diphenylfluorenyl, obtained by cyano substitution, 9,9'-spirobis[9H-fluorene]-2-yl obtained by cyano substitution, 9,9-dimethylfluorenyl obtained by substitution with cyano, or Triphenylene oxide obtained by substituted cyano group.

77. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), X 26 With Y 23 via L 23 Bonding or direct bonding, X 26 With Y 22 via L 23 Bonding or direct bonding, X 27 With Y 23 via L 23 Bonding or direct bonding.

78. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), w is 0 or 1.

79. The organic electroluminescent element as described in claim 72, characterized in that, In the general formula (21), L 21 and L 22 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms that is either a single bond, substituted or unsubstituted.

80. The organic electroluminescent element as claimed in claim 1, characterized in that, The second compound is any one of the following compounds:

81. The organic electroluminescent element as claimed in claim 1, characterized in that, The third compound is either a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence.

82. The organic electroluminescent element as described in claim 81, characterized in that, The third compound is a derivative selected from the group consisting of carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives.

83. The organic electroluminescent element as described in claim 81, characterized in that, The third compound is a compound in which at least one of the following general formulas (31), (32), (33A), and (34A) is contained in one molecule. In the general formula (31), Y 31 ~Y 36 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. Among them, Y 31 ~Y 36 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound. In the general formula (32), Y 41 ~Y 48 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. Among them, Y 41 ~Y 48 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound. X 30 Nitrogen, oxygen, or sulfur atoms that are bonded to other atoms in the molecule of the third compound. In the general formulas (33A) and (34A), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

84. The organic electroluminescent element as described in claim 83, characterized in that, The local structure represented by the general formula (32) is any one of the local structures selected from the group consisting of the local structures represented by the following general formulas (321), (322), (323), (324), (325), and (326). In the general formulas (321) to (326), X 30 Each of the nitrogen, oxygen, or sulfur atoms is independently bonded to other atoms in the molecule of the third compound. Y 41 ~Y 48 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. X 31 Each of the following is an independent nitrogen atom, oxygen atom, sulfur atom, or carbon atom bonded to other atoms in the molecule of the third compound. Y 61 ~Y 64 Carbon atoms that are either nitrogen atoms or carbon atoms bonded independently to other atoms in the molecule of a third compound.

85. The organic electroluminescent element as described in claim 83, characterized in that, The local structure represented by the general formula (31) is included in the third compound as at least any group selected from the group represented by the general formula (33) and the group represented by the general formula (34). In the general formula (33), Y 31 Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 , In the general formula (34), Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 , In the general formulas (33) and (34), R 31 Each can be an independent hydrogen atom or a substituent. R as a substituent 31 Independently from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms Substituted or unsubstituted silyl groups Replacement of germanium-based Substituted phosphine oxide group, Halogen atoms, cyano, Nitro, and Substituted or unsubstituted carboxyl groups Choose from the groups that make up the group. Wherein, the R 31 The aryl groups in the ring, whether substituted or unsubstituted, with 6 to 30 carbon atoms, are non-fused rings. In the general formulas (33) and (34), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

86. The organic electroluminescent element as described in claim 85, characterized in that, In the general formula (33), Y 31 Y 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

87. The organic electroluminescent element as described in claim 85, characterized in that, In the general formula (34), Y 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

88. The organic electroluminescent element as described in claim 83, characterized in that, The local structure represented by the general formula (32) is included in the third compound as at least one group selected from the group composed of groups represented by the following general formulas (35) to (39) and the following general formula (30a). In the general formula (35), Y 41 ~Y 48 Each independently consists of a nitrogen atom or CR 32 , In the general formulas (36) and (37), Y 41 ~Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 , In the general formula (38), Y 41 Y 42 Y 44 Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 , In the general formula (39), Y 42 ~Y 48 Each independently consists of a nitrogen atom or CR 32 , In the general formula (30a), Y 42 ~Y 47 Each independently consists of a nitrogen atom or CR 32 In the general formulas (35) to (39) and (30a), R 32 Each can be an independent hydrogen atom or a substituent. R as a substituent 32 from Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted silyl groups, Replacement of germanium-based Substituted phosphine oxide group, Halogen atoms, cyano, Nitro, and Substituted or unsubstituted carboxyl groups Choose from the groups that make up the group. Multiple R 32 Whether they are the same or different, In the general formulas (37) to (39) and (30a), X 30 For NR 33 Oxygen or sulfur atoms, R 33 from Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted silyl groups, Replacement of germanium-based Substituted phosphine oxide group, Fluorine atom, cyano, Nitro, and Substituted or unsubstituted carboxyl groups Choose from the groups that make up the group. Multiple R 33 Whether they are the same or different, Wherein, the R 33 The aryl groups in the ring, whether substituted or unsubstituted, with 6 to 30 carbon atoms, are non-fused rings. In the general formulas (35) to (39) and (30a), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

89. The organic electroluminescent element as described in claim 88, characterized in that, In the general formula (35), Y 41 ~Y 48 CR independently 32 , In general formulas (36) and (37), Y 41 ~Y 45 Y 47 and Y 48 CR independently 32 , In the general formula (38), Y 41 Y 42 Y 44 Y 45 Y 47 and Y 48 CR independently 32 , In the general formula (39), Y 42 ~Y 48 CR independently 32 , In the general formula (30a), Y 42 ~Y 47 CR independently 32 , Multiple R 32 They are the same or different from each other.

90. The organic electroluminescent element according to any one of claims 83, 84, 88, and 89, characterized in that, X 30 It consists of oxygen or sulfur atoms.

91. The organic electroluminescent element as described in claim 85, characterized in that, R 31 R can be a hydrogen atom or a substituent, and can be a substituent. 31 Each of the following groups can be independently selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms.

92. The organic electroluminescent element as described in claim 88 or 89, characterized in that, R 32 R can be a hydrogen atom or a substituent, and can be a substituent. 32 Each of the following groups can be independently selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms.

93. The organic electroluminescent element as described in claim 1, characterized in that, The light-emitting layer does not contain metal complexes.

94. An electronic device, characterized in that, It is equipped with an organic electroluminescent element as described in any one of claims 1 to 93.

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