Organic electroluminescent element and electronic device

Abstract

The present invention relates to an organic EL element having a light-emitting layer, a first layer in contact therewith on the anode side, and a second layer in contact therewith on the cathode side. The light-emitting layer contains first, second, and third compounds. The first layer contains a compound of formula (A), and the second layer contains a compound of formula (B). The first compound is a fluorescent compound of formula (1), the second compound is a delayed fluorescence compound of formula (2), and the third compound is a compound of formula (3). Their singlet energies S1 satisfy S1(M3) > S1(M2) > S1(M1). In formula (A), Ra1 to Ra5, etc. are each independently a substituent, etc. In formula (B), X1 to X3 are each independently an N atom, etc., Ar1 and Ar2 are each independently a group of formula (1B), etc., A is a group of formula (1B). In formula (1B), HAr is represented by formula (2B), a is 1 to 5, L1 is a linking group, etc. In formula (2B), X 11 ~X 18 are each independently an N atom, etc., and Y1 is O, S, or an N atom, etc. #imgabs0#

Description

Technical Field

[0001] The present invention relates to an organic electroluminescent element and an electronic device. Background Art

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

[0003] Fluorescent organic EL elements using light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency of 25% is called the limit. Therefore, research is being conducted to improve the performance of organic EL elements.

[0004] In addition, it is expected to utilize triplet excitons in addition to singlet excitons, so that the organic EL element emits light more efficiently. Against this background, highly efficient fluorescent organic EL elements utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and studied.

[0005] For example, the TADF (Thermally Activated Delayed Fluorescence) mechanism is studied. This TADF mechanism is a mechanism that utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under the action of heat in the case of using a material having a small energy difference (ΔST) between singlet energy levels and triplet energy levels. Regarding thermally activated delayed fluorescence, it is described, for example, in "Chinami Adachi, 'Device Physics of Organic Semiconductors', Kodansha, published on April 1, 2012, pages 261 to 268".

[0006] Patent Documents 1 and 2 disclose an organic EL element 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 contains an amine compound. In addition, the electron transport layer described in Patent Documents 1 and 2 contains a compound in which a heteroaryl group is bonded directly or via a linking group to an azine ring having an aryl group.

[0007] Prior Art 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] Technical Problem to be Solved by the Invention

[0012] In an organic EL element utilizing the TADF mechanism, further improvement in performance is required.

[0013] An object of the present invention is to provide a high-performance organic electroluminescent element and an electronic device.

[0014] Solution for Solving the Above Technical Problem

[0015] According to one aspect of the present invention, there is provided an organic electroluminescent element having:

[0016] an anode;

[0017] a cathode;

[0018] a light-emitting layer disposed between the anode and the cathode;

[0019] a first layer disposed between the anode and the light-emitting layer and adjacent to the light-emitting layer;

[0020] a second layer disposed between the cathode and the light-emitting layer and adjacent to the light-emitting layer,

[0021] the light-emitting layer contains a first compound, a second compound, and a third compound,

[0022] the first layer contains a compound represented by the following general formula (A),

[0023] the second layer contains a compound represented by the following general formula (B),

[0024] the first compound is a fluorescent compound represented by the following general formula (1),

[0025] the second compound is a delayed fluorescence compound represented by the following general formula (2),

[0026] the third compound is represented by the following general formula (3),

[0027] The singlet energy S1(M1) of the first compound, the singlet energy S1(M2) of the second compound, and the singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 1).

[0028] S1(M3)>S1(M2)>S1(M1)…(Equation 1)

[0029] [Chemical Formula 1]

[0030]

[0031] In the general formula (A),

[0032] Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 are each independently a hydrogen atom or a substituent, and Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 as substituents are each independently,

[0033] a halogen atom,

[0034] a cyano group,

[0035] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0036] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0037] Rc1 is a hydrogen atom or a substituent, or the group of Rc1 and Rc2 are bonded to each other to form a ring, and Rc1 as a substituent is,

[0038] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,

[0039] Rc2 is a hydrogen atom or a substituent, or the group of Rc1 and Rc2 are bonded to each other to form a ring. When the group of Rc1 and Rc2 are bonded to each other to form a ring, the ring contains at least a five-membered ring, and the five-membered ring contains at least any one of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms. Among them, Rc1 and Rc2 are not simultaneously hydrogen atoms,

[0040] Rc2 as a substituent is,

[0041] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0042] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0043] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0044] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, or

[0045] a substituted or unsubstituted amino group.

[0046] [Chemical Formula 2]

[0047]

[0048] In the general formula (B),

[0049] X1 to X3 are each independently a nitrogen atom or CR1, and at least any one of X1 to X3 is a nitrogen atom,

[0050] R1 is a hydrogen atom or a substituent,

[0051] As a substituent, R1 is independently,

[0052] a halogen atom,

[0053] a cyano group,

[0054] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0055] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0056] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0057] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0058] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0059] a substituted or unsubstituted silyl group,

[0060] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0061] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or

[0062] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0063] Ar1 and Ar2 are each independently,

[0064] represented by the following general formula (1B), or is

[0065] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0066] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0067] A is represented by the following general formula (1B).

[0068] [Chemical formula 3]

[0069]

[0070] In the general formula (1B),

[0071] HAr is represented by the following general formula (2B),

[0072] a is 1, 2, 3, 4 or 5,

[0073] When a is 1, L1 is a single bond or a divalent linking group,

[0074] When a is 2, 3, 4 or 5, L1 is a linking group with a valence of 3 or more and 6 or less,

[0075] Multiple HArs are the same as or different from each other,

[0076] The linking group is,

[0077] A group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0078] A group derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0079] A group derived from a group obtained by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms to each other, or

[0080] A group derived from a group obtained by bonding three groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms to each other,

[0081] In addition, the groups obtained by bonding to each other are the same as or different from each other.

[0082] [Chemical formula 4]

[0083]

[0084] In the general formula (2B),

[0085] X 11 ~X 18 Are each independently a nitrogen atom, CR 13 Or a carbon atom bonded to L1,

[0086] Multiple Rs 13 Are the same as or different from each other,

[0087] Y1 is an oxygen atom, a sulfur atom, NR 18 、SiR 11 R 12 、CR 14 R 15 、A nitrogen atom bonded to L1, a silicon atom bonded to R 16 And L1 respectively, or a carbon atom bonded to R 17 And L1 respectively,

[0088] Among them, those bonded to L1 are X 11 ~X 18 、R 11 ~R 12 And R 14 ~R15 any one of the carbon atoms in, and the nitrogen, silicon, and carbon atoms in Y1

[0089] R 11 and R 12 are the same as or different from each other, R 14 and R 15 are the same as or different from each other,

[0090] R 11 ~R 18 are each independently a hydrogen atom or a substituent, or adjacent R 13 groups, R 11 and R 12 groups, and also R 14 and R 15 any one or more groups among the groups bond to each other to form a ring,

[0091] As substituents, R 11 ~R 18 are each independently,

[0092] a halogen atom,

[0093] a cyano group,

[0094] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0095] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0096] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0097] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0098] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0099] a substituted or unsubstituted silyl group,

[0100] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0101] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or

[0102] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[0103] [Chemical Formula 5]

[0104]

[0105] In the general formula (1),

[0106] X is a nitrogen atom or a carbon atom bonded to Y,

[0107] Y is a hydrogen atom or a substituent,

[0108] R 21 ~R 26 are each independently a hydrogen atom or a substituent, or R 21 and R 22 of the group, R 22 and R 23 of the group, R 24 and R 25 of the group, and also R 25 and R 26 of the group, any one or more of the groups bond to each other to form a ring,

[0109] Y and R as substituents 21 ~R 26 each independently from

[0110] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0111] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0112] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0113] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0114] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0115] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms,

[0116] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0117] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0118] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0119] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0120] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0121] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0122] a halogen atom,

[0123] a carboxyl group,

[0124] a substituted or unsubstituted ester group,

[0125] A substituted or unsubstituted carbamoyl group,

[0126] A substituted or unsubstituted amino group,

[0127] A nitro group,

[0128] A cyano group,

[0129] A substituted or unsubstituted silyl group, and

[0130] is selected from the group consisting of a substituted or unsubstituted siloxanyl group,

[0131] Z 21 and Z 22 are each independently a substituent, or Z 21 and Z 22 bond to each other to form a ring,

[0132] Z as a substituent 21 and Z 22 each independently is selected from

[0133] a halogen atom,

[0134] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0135] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0136] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0137] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0138] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and

[0139] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[0140] [Chemical formula 6]

[0141]

[0142] In the general formula (2), D1 is a group represented by the following general formula (2-1), D2 is a group represented by the following general formula (2-2), and a plurality of D2s are the same groups as each other.

[0143] [Chemical formula 7]

[0144]

[0145] In the general formula (2-1), X4 is an oxygen atom or a sulfur atom, and R 131 ~R 140 are each independently a hydrogen atom or a substituent,

[0146] R as a substituent 131 ~R 140 are each independently

[0147] an aryl group having 6 to 14 ring carbon atoms, which may be substituted or unsubstituted,

[0148] a heterocyclic group having 5 to 14 ring atoms, which may be substituted or unsubstituted,

[0149] an alkyl group having 1 to 6 carbon atoms, which may be substituted or unsubstituted,

[0150] an alkylsilyl group having 3 to 6 carbon atoms, which may be substituted or unsubstituted,

[0151] an alkoxy group having 1 to 6 carbon atoms, which may be substituted or unsubstituted,

[0152] an aryloxy group having 6 to 14 ring carbon atoms, which may be substituted or unsubstituted,

[0153] an alkylamino group having 2 to 12 carbon atoms, which may be substituted or unsubstituted,

[0154] an alkylthio group having 1 to 6 carbon atoms, which may be substituted or unsubstituted, or

[0155] an arylthio group having 6 to 14 ring carbon atoms, which may be substituted or unsubstituted.

[0156] * indicates the position bonded to the benzene ring in the general formula (2).

[0157] [Chemical formula 8]

[0158]

[0159] In the general formula (2-2), R 161 ~R 168 are each independently a hydrogen atom or a substituent,

[0160] R as a substituent 161 ~R 168 are each independently

[0161] a halogen atom,

[0162] an aryl group having 6 to 14 ring carbon atoms, which may be substituted or unsubstituted,

[0163] a heterocyclic group having 5 to 14 ring atoms, which may be substituted or unsubstituted,

[0164] an alkyl group having 1 to 6 carbon atoms, which may be substituted or unsubstituted,

[0165] a haloalkyl group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0166] A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms,

[0167] A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms,

[0168] A substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms,

[0169] A substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms,

[0170] A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or

[0171] A substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0172] * Each independently represents a position bonded to the benzene ring in the general formula (2).

[0173] [Chemical formula 9]

[0174]

[0175] In the general formula (3), A 31 is a group represented by the following general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e), or general formula (31f),

[0176] R 31 ~R 38 are each independently a hydrogen atom or a substituent, R 401 ~R 404 and R 409 ~R 412 are each independently a hydrogen atom or a substituent,

[0177] As substituents, R 31 ~R 38 and as substituents, R 401 ~R 404 and R 409 ~R 412 are each independently

[0178] a halogen atom,

[0179] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0180] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0181] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0182] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0183] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0184] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0185] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0186] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0187] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0188] a hydroxyl group,

[0189] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0190] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0191] an amino group,

[0192] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0193] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0194] a mercapto group,

[0195] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0196] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms.

[0197] [Chemical formula 10]

[0198]

[0199] [Chemical formula 11]

[0200]

[0201] [Chemical formula 12]

[0202]

[0203] In the general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e), and general formula (31f),

[0204] R 310 ~R 319 are each independently a hydrogen atom or a substituent,

[0205] R 320 ~R 329Each is independently a hydrogen atom or a substituent,

[0206] R 330 ~R 339 Each is independently a hydrogen atom or a substituent,

[0207] R 340 ~R 349 Each is independently a hydrogen atom or a substituent,

[0208] R 350 ~R 359 Each is independently a hydrogen atom or a substituent,

[0209] R 360 ~R 369 Each is independently a hydrogen atom or a substituent,

[0210] R as a substituent 310 ~R 319 、R 320 ~R 329 、R 330 ~R 339 、R 340 ~R 349 、R 350 ~R 359 and R 360 ~R 369 Each is independently synonymous with R as a substituent in the general formula (3) 31 ~R 38 and R as a substituent 401 ~R 404 and R 409 ~R 412 * Each independently represents the position bonded to the benzene ring having R 401 ~R 404 in the general formula (3).)

[0211] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element of one aspect of the present invention described above.

[0212] According to one aspect of the present invention, it is possible to provide a high-performance organic EL element and an electronic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0213] Figure 1 It is a diagram showing a schematic configuration of an example of the organic EL element of the first embodiment.

[0214] Figure 2 It is a schematic diagram of a device for measuring transient PL.

[0215] Figure 3 It is a diagram showing an example of the decay curve of transient PL.

[0216] Figure 4 It is a diagram showing the relationship between the energy levels and energy transfer of a first compound, a second compound, and a third compound in a light-emitting layer, which is an example of an organic EL element of the first embodiment. Detailed implementation manners

[0217] 〔First embodiment〕

[0218] The configuration of the organic EL element of the first embodiment of the present invention will be described.

[0219] The organic EL element has an organic layer between two electrodes, an anode and a cathode. This organic layer is usually formed by laminating a plurality of layers composed of organic compounds. The organic layer may also contain an inorganic compound. At least one layer of the organic layer is a light-emitting layer.

[0220] In the present embodiment, the organic layer has a light-emitting layer between the anode and the cathode, a first layer adjacent to the light-emitting layer and included between the anode and the light-emitting layer, and a second layer adjacent to the light-emitting layer and included between the cathode and the light-emitting layer.

[0221] The light-emitting layer contains a first compound represented by the general formula (1), a second compound represented by the general formula (2), and a third compound represented by the general formula (3). The first compound is a fluorescent compound, and the second compound is a delayed fluorescent compound.

[0222] The first layer contains a compound represented by the general formula (A). The first layer is not particularly limited. For example, at least any one layer selected from the group consisting of a hole injection layer, a hole transport layer, and an electron blocking layer can be cited. The first layer is preferably an electron blocking layer.

[0223] The second layer contains a compound represented by the general formula (B). The second layer is not particularly limited. For example, at least any one layer selected from the group consisting of an electron injection layer, an electron transport layer, and a hole blocking layer can be cited. The second layer is preferably a hole blocking layer.

[0224] That is, the organic layer of the organic EL element of the present embodiment preferably has the following layer structure.

[0225] · Electron blocking layer / Light-emitting layer / Hole blocking layer

[0226] · Hole injection layer / Electron blocking layer / Light-emitting layer / Hole blocking layer

[0227] · Hole transport layer / Electron blocking layer / Light-emitting layer / Hole blocking layer

[0228] · Hole injection layer / Hole transport layer / Electron blocking layer / Light-emitting layer / Hole blocking layer

[0229] · Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer

[0230] · Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer

[0231] · Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer

[0232] · Hole injection layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer

[0233] · Hole injection layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer

[0234] · Hole injection layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer

[0235] · Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer

[0236] · Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer

[0237] · Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer

[0238] · Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer

[0239] · Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer

[0240] · Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer

[0241] Figure 1 The schematic configuration of an example of the organic EL element in the present embodiment is shown.

[0242] The organic EL element 1 includes a transmissive 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 laminated in this order 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.

[0243] The light emitting layer 5 may also contain a metal complex.

[0244] The light emitting layer 5 preferably does not contain a phosphorescent material (dopant material).

[0245] The light-emitting layer 5 preferably does not contain heavy metal complexes and phosphorescent rare-earth metal complexes. Here, examples of the heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0246] In addition, the light-emitting layer 5 preferably does not contain metal complexes.

[0247] The first compound is preferably a dopant material (sometimes also referred to as a guest material, emitter, or light-emitting material).

[0248] The second compound is preferably a host material (sometimes also referred to as a matrix material).

[0249] The third compound is preferably a host material. Sometimes, one of the second compound and the third compound is referred to as the first host material, and the other is referred to as the second host material. The third compound may be a compound with delayed fluorescence or a compound without delayed fluorescence.

[0250] Conventionally, an organic EL element having a light-emitting layer containing three compounds, namely, a fluorescent compound, a TADF compound, and a third compound, has been known. In order to achieve a high-performance organic EL element that emits light at a low voltage or with high efficiency and has a long element life compared to conventional organic EL elements, it is necessary to improve the hole injection property into the light-emitting layer. In addition, it is necessary to keep the holes injected into the light-emitting layer in the light-emitting layer for a longer time and efficiently generate excitons. However, in the combinations of the light-emitting layer and its peripheral layers (such as an electron blocking layer and a hole blocking layer) known so far, the improvement of the hole injection property into the light-emitting layer and the efficient generation of excitons in the light-emitting layer are insufficient.

[0251] The inventors of the present invention have found that by making the first layer containing the compound represented by the general formula (A) adjacent to the light-emitting layer on the anode side, making the second layer containing the compound represented by the general formula (B) adjacent to the light-emitting layer on the cathode side, and further including a fluorescent first compound (compound represented by the general formula (1)), a delayed fluorescence second compound (compound represented by the general formula (2)), and a third compound (compound represented by the general formula (3)) in the light-emitting layer, a high-performance organic EL element can be achieved.

[0252] Hereinafter, the configuration of the organic EL element of the present embodiment will be described in detail.

[0253] <First layer>

[0254] The first layer 6 contains a compound represented by the following general formula (A).

[0255] [Chemical formula 13]

[0256]

[0257] In the general formula (A), Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 are each independently a hydrogen atom or a substituent. As substituents, Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 are each independently,

[0258] a halogen atom,

[0259] a cyano group,

[0260] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0261] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0262] Rc1 is a hydrogen atom or a substituent, or bonds to Rc2 to form a ring. As a substituent, Rc1 is

[0263] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,

[0264] Rc2 is a hydrogen atom or a substituent, or the group of Rc1 and Rc2 bonds to each other to form a ring. When the group of Rc1 and Rc2 bonds to each other to form a ring, the ring contains at least a five-membered ring, and the five-membered ring contains at least any one of a carbon atom, an oxygen atom, a sulfur atom, and a nitrogen atom. Among them, Rc1 and Rc2 are not hydrogen atoms at the same time.

[0265] As a substituent, Rc2 is,

[0266] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0267] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0268] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0269] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, or

[0270] a substituted or unsubstituted amino group.

[0271] In the general formula (A), preferably, when one or more of Ra1 to Ra5 are unsubstituted dibenzofuranyl groups, none of Rb1 to Rb5 and Rc2 to Rc5 is an unsubstituted dibenzofuranyl group; when one or more of Rb1 to Rb5 are unsubstituted dibenzofuranyl groups, none of Ra1 to Ra5 and Rc2 to Rc5 is an unsubstituted dibenzofuranyl group; when one or more of Rc2 to Rc5 are unsubstituted dibenzofuranyl groups, none of Ra1 to Ra5 and Rb1 to Rb5 is an unsubstituted dibenzofuranyl group.

[0272] In the general formula (A), more preferably, when one or more of Ra1 to Ra5 are a substituted or unsubstituted dibenzofuranyl group, none of Rb1 to Rb5 and Rc2 to Rc5 is a substituted or unsubstituted dibenzofuranyl group; when one or more of Rb1 to Rb5 are a substituted or unsubstituted dibenzofuranyl group, none of Ra1 to Ra5 and Rc2 to Rc5 is a substituted or unsubstituted dibenzofuranyl group; when one or more of Rc2 to Rc5 are a substituted or unsubstituted dibenzofuranyl group, none of Ra1 to Ra5 and Rb1 to Rb5 is a substituted or unsubstituted dibenzofuranyl group.

[0273] In the general formula (A), it is preferred that the groups of Rc1 and Rc2 are bonded to each other to form a ring.

[0274] In the general formula (A), it is further preferred that Rc1 is a hydrogen atom or a substituent, and Rc2 is a hydrogen atom or a substituent. Herein, Rc1 and Rc2 are not simultaneously hydrogen atoms.

[0275] Herein, the following general formula (1A) is used to illustrate the meaning that the groups of Rc1 and Rc2 are bonded to each other to form a ring, and at least one of Rc1 and Rc2 is a specific substituent.

[0276] The following general formula (1A) is a partial structure of the compound represented by the general formula (A).

[0277] [Chemical formula 14]

[0278]

[0279] In the general formula (1A), Rc1 has the same meaning as Rc1 in the general formula (A), Rc2 has the same meaning as Rc2 in the general formula (A), Rc3 to Rc5 are each independently the same as Rc3 to Rc5 in the general formula (A), and * represents the bonding site to the nitrogen atom in the compound represented by the general formula (A).

[0280] In the general formula (1A), the groups of Rc1 and Rc2 being bonded to each other to form a ring means that Rc1 and Rc2 form a ring Z represented by, for example, the following general formula (11A) 11A .

[0281] [Chemical formula 15]

[0282]

[0283] On the other hand, in the general formula (1A), when Rc2 and Rc3 form a ring Z represented by the following general formula (11B) 11Bthe case where, and Rc3 and Rc4 form a ring Z represented by the following general formula (11C) 11C in the case where, neither of the following general formulas (11B) and (11C) satisfies the general formula (1A).

[0284] [Chemical formula 16]

[0285]

[0286] In the general formula (A), Rc1 and Rc2 near the nitrogen atom are bonded to each other to have the ring Z 11A , or at least one of Rc1 and Rc2 has a specific substituent. Therefore, for example, Rc2 and Rc3 are bonded to each other to have the ring Z 11B the compound, Rc3 and Rc4 are bonded to each other to have the ring Z 11C the compound, and the compound in which Rc3 has a substituent, the compound represented by the general formula (A) has a structure with a larger volume around the nitrogen atom. Thus, it is considered that the orbital of the HOMO (highest occupied molecular orbital) of the compound represented by the general formula (A) becomes narrower and the ionization potential Ip becomes deeper (the absolute value becomes larger).

[0287] Therefore, it is considered that, according to the organic EL element 1 of the present embodiment, by making the first layer adjacent to the light-emitting layer 5 on the anode 3 side contain the compound represented by the general formula (A), the hole injection property into the light-emitting layer 5 and the generation efficiency of excitons in the light-emitting layer are improved. As a result, the performance of the organic EL element is improved.

[0288] In the general formula (A), the part represented by the general formula (1A) is preferably a group represented by any one of the following general formulas (1A-1) to (1A-10).

[0289] [Chemical formula 17]

[0290]

[0291] [Chemical formula 18]

[0292]

[0293] In the general formulas (1A-1) to (1A-10), R A is a hydrogen atom or a substituent, and R A as a substituent are each independently

[0294] a halogen atom,

[0295] a cyano group,

[0296] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0297] a heteroaryl group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted,

[0298] an alkyl group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0299] an alkenyl group having 2 to 30 carbon atoms, which may be substituted or unsubstituted,

[0300] an alkynyl group having 2 to 30 carbon atoms, which may be substituted or unsubstituted,

[0301] a silyl group, which may be substituted or unsubstituted,

[0302] an alkoxy group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0303] an aralkyl group having 7 to 30 carbon atoms, which may be substituted or unsubstituted, or

[0304] an aryloxy group having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted. In the case where there are a plurality of Rs A Rs A are the same as or different from each other, and * represents the site bonded to the nitrogen atom in the compound represented by the general formula (A).

[0305] 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).

[0306] The group represented by the general formula (1A) is also 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).

[0307] 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).

[0308] In the general formulas (1A-1) to (1A-10), R A is preferably a hydrogen atom.

[0309] In the general formula (A), it is preferred that Ra1 to Ra5 and Rb1 to Rb5 are each independently a hydrogen atom, or an aryl group having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted.

[0310] In the general formula (A), it is also preferred that Ra1 to Ra5 are each independently a hydrogen atom, or an aryl group having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted, and Rb1 to Rb5 are each independently a hydrogen atom, or a heteroaryl group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[0311] In the general formula (A), it is also preferable that Ra1 to Ra5 are each independently a hydrogen atom or an aryl group having 6 to 30 carbon atoms in the ring, which is substituted with a heteroaryl group having 5 to 30 ring atoms, and Rb1 to Rb5 are each independently a hydrogen atom or a heteroaryl group having 5 to 30 ring atoms, which may or may not be substituted.

[0312] In the general formula (A), it is also preferable that Ra1 to Ra5 and Rb1 to Rb5 are each independently a hydrogen atom or a heteroaryl group having 5 to 30 ring atoms, which may or may not be substituted.

[0313] In the general formula (A), it is preferable that one of Ra1 to Ra5 is a substituent, Ra1 to Ra5 other than this substituent are hydrogen atoms, one of Rb1 to Rb5 is a substituent, Rb1 to Rb5 other than this substituent are hydrogen atoms, and Rc3 to Rc5 are hydrogen atoms.

[0314] In the general formula (A), it is preferable that Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 as substituents are each independently a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 carbon atoms in the ring, or an unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0315] In the general formula (A), it is preferable that one of Ra1 to Ra5 is a substituent, Ra1 to Ra5 other than this substituent are hydrogen atoms, one of Rb1 to Rb5 is a substituent, Rb1 to Rb5 other than this substituent are hydrogen atoms, Rc3 to Rc5 are hydrogen atoms, and Ra1 to Ra5 and Rb1 to Rb5 as substituents are each independently a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 carbon atoms in the ring, or an unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0316] In the general formula (A), it is preferable 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).

[0317] [Chemical formula 19]

[0318]

[0319] [Chemical formula 20]

[0320]

[0321] In the general formulas (1B-1) to (1B-10), R B is a hydrogen atom or a substituent, and R as a substituent BEach independently is,

[0322] a halogen atom,

[0323] a cyano group,

[0324] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0325] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0326] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0327] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0328] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0329] a substituted or unsubstituted silyl group,

[0330] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0331] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or

[0332] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms. In the case where there are a plurality of Rs B , the Rs B are the same as or different from each other. * represents the bonding site to the benzene ring bonded to Ra1 to Ra5 and Rb1 to Rb5 in the compound represented by the general formula (A).

[0333] In the general formulas (1B-1) to (1B-10), R B is preferably a hydrogen atom.

[0334] The compound represented by the general formula (A) is preferably a compound represented by the following general formula (1X), the following general formula (1Y) or the following general formula (1Z), and more preferably a compound represented by the following general formula (1X).

[0335] [Chemical formula 21]

[0336]

[0337] [Chemical formula 22]

[0338]

[0339] In the general formulas (1X), the general formula (1Y) and the general formula (1Z), Ra1 to Ra5 and Rb1 to Rb5 are respectively synonymous with Ra1 to Ra5 and Rb1 to Rb5 in the general formula (A), and R Ais synonymous with R in the general formulas (1A-1) to (1A-10). A synonymous

[0340] In the general formula (1X), the general formula (1Y), and the general formula (1Z), at least one of Ra1 to Ra5 is preferably 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 preferably independently a group represented by any one of the general formulas (1B-1) to (1B-10).

[0341] In the general formula (1X), the general formula (1Y), and the general formula (1Z), more 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).

[0342] In the general formula (1X), the general formula (1Y), and the general formula (1Z), R A is preferably a hydrogen atom.

[0343] In the general formulas (1B-1) to (1B-10), R B is preferably a hydrogen atom.

[0344] From the viewpoints of improving the hole injection property into the light-emitting layer and efficiently generating excitons in the light-emitting layer, the ionization potential Ip of the compound represented by the general formula (A) is preferably 5.78 eV or more, more preferably 5.80 eV or more, and further preferably 5.85 eV or more.

[0345] The method for measuring the ionization potential Ip of the compound represented by the general formula (A) is as described in the examples below.

[0346] · Manufacturing method of the compound represented by the general formula (A)

[0347] The compound represented by the general formula (A) can be manufactured by a known method.

[0348] Specific examples of the compound represented by the general formula (A) are shown below. In addition, the compound represented by the general formula (A) in the present invention is not limited to these specific examples.

[0349] [Chemical formula 23]

[0350]

[0351] [Chemical formula 24]

[0352]

[0353] [Chemical formula 25]

[0354]

[0355] [Chemical formula 26]

[0356]

[0357] [Chemical formula 27]

[0358]

[0359] [Chemical formula 28]

[0360]

[0361] <The second layer>

[0362] The second layer 7 contains a compound represented by the following general formula (B).

[0363] [Chemical formula 29]

[0364]

[0365] In the general formula (B),

[0366] X1 to X3 are each independently a nitrogen atom or CR1, and at least any one of X1 to X3 is a nitrogen atom,

[0367] R1 is a hydrogen atom or a substituent,

[0368] R1 as a substituent is each independently,

[0369] a halogen atom,

[0370] a cyano group,

[0371] an aryl group having 6 to 30 ring carbon atoms which is substituted or unsubstituted,

[0372] a heteroaryl group having 5 to 30 ring atoms which is substituted or unsubstituted,

[0373] an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted,

[0374] an alkenyl group having 2 to 30 carbon atoms which is substituted or unsubstituted,

[0375] an alkynyl group having 2 to 30 carbon atoms which is substituted or unsubstituted,

[0376] a silyl group which is substituted or unsubstituted,

[0377] an alkoxy group having 1 to 30 carbon atoms which is substituted or unsubstituted,

[0378] A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or

[0379] A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms,

[0380] Ar1 and Ar2 are each independently,

[0381] represented by the following general formula (1B), or is

[0382] A substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or

[0383] A substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms.

[0384] A is represented by the following general formula (1B). )

[0385] [Chemical formula 30]

[0386]

[0387] In the general formula (1B),

[0388] HAr is represented by the following general formula (2B),

[0389] a is 1, 2, 3, 4 or 5,

[0390] When a is 1, L1 is a single bond or a divalent linking group,

[0391] When a is 2, 3, 4 or 5, L1 is a trivalent or higher and hexavalent or lower linking group,

[0392] Multiple HArs are the same as or different from each other,

[0393] The linking group is,

[0394] A group derived from a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,

[0395] A group derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms,

[0396] A group derived from a group obtained by bonding to each other two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, or

[0397] A group derived from a group obtained by bonding to each other three groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms,

[0398] In addition, the groups obtained by bonding to each other are the same as or different from each other.

[0399] [Chemical formula 31]

[0400]

[0401] In the general formula (2B),

[0402] X 11 ~X 18 are each independently a nitrogen atom, CR 13 or a carbon atom bonded to L1,

[0403] Multiple Rs 13 are the same as or different from each other,

[0404] Y1 is an oxygen atom, a sulfur atom, NR 18 , SiR 11 R 12 , CR 14 R 15 , a nitrogen atom bonded to L1, a silicon atom bonded to R 16 and L1 respectively, or a carbon atom bonded to R 17 and L1 respectively,

[0405] wherein, the one bonded to L1 is one of X 11 ~X 18 , R 11 ~R 12 and R 14 ~R 15 among the carbon atoms, and any one of the nitrogen atom, silicon atom and carbon atom in Y1,

[0406] R 11 and R 12 are the same as or different from each other, R 14 and R 15 are the same as or different from each other,

[0407] R 11 ~R 18 are each independently a hydrogen atom or a substituent, or any one or more groups among the groups of adjacent Rs 13 , the group of R 11 and R 12 , and the group of R 14 and R 15 are bonded to each other to form a ring,

[0408] Rs as substituents 11 ~R 18 are each independently,

[0409] a halogen atom,

[0410] a cyano group,

[0411] Aryl groups having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted,

[0412] Heteroaryl groups having 5 to 30 ring atoms, which may be substituted or unsubstituted,

[0413] Alkyl groups having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0414] Alkenyl groups having 2 to 30 carbon atoms, which may be substituted or unsubstituted,

[0415] Alkynyl groups having 2 to 30 carbon atoms, which may be substituted or unsubstituted,

[0416] Silyl groups, which may be substituted or unsubstituted,

[0417] Alkoxy groups having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0418] Aryalkyl groups having 7 to 30 carbon atoms, which may be substituted or unsubstituted, or

[0419] Aryloxy groups having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted.

[0420] When Y1 is a silicon atom bonded to R 16 and L1 respectively, the general formula (2B) is represented by the following general formula (2B-1). In the general formula (2B-1), X 11 to X 18 are respectively synonymous with X 11 to X 18 in the general formula (2B).

[0421] When Y1 is a carbon atom bonded to R 17 and L1 respectively, the general formula (2B) is represented by the following general formula (2B-2). In the general formula (2B-2), X 11 to X 18 are respectively synonymous with X 11 to X 18 in the general formula (2B).

[0422] [Chemical formula 32]

[0423]

[0424] In the general formula (1B), L1 as a linking group is further preferably a residue having a valence of two or more and six or less derived from an aryl group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted.

[0425] In the general formula (1B), L1 as a linking group is further preferably a residue having a valence of three or more and six or less derived from an aryl group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted.

[0426] In the general formula (1B), a is preferably 1, 2 or 3, more preferably 1 or 2.

[0427] When a is 1, L1 is a divalent linking group, and the general formula (1B) is represented by the following general formula (11B-1).

[0428] When a is 2, 3, 4 or 5, L1 is a linking group having a valence of 3 or more and 6 or less. When a is 2, L1 is a trivalent linking group, and the general formula (1B) is represented by the following general formula (11B-2). At this time, HArs are the same or different.

[0429] [Chemical formula 33]

[0430] (HAr)-L1- (11B-1)

[0431]

[0432] In the general formulas (11B-1) and (11B-2), L1 is a divalent or trivalent linking group, and the linking group is a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a group derived from a group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms to each other, or a group derived from a group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms to each other.

[0433] In L1 of the general formulas (1B), (11B-1) and (11B-2), the group formed by bonding two or three of these groups means a group formed by bonding two or three divalent or trivalent residues derived from the aryl group having 6 to 30 ring carbon atoms and the heteroaryl group having 5 to 30 ring atoms to each other by single bonds. In this linking group, the groups bonded to each other are the same or different.

[0434] Preferably, in the general formulas (1B), (11B-1) and (11B-2), L1 as the linking group is a divalent or trivalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent or trivalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0435] More preferably, in the general formulas (1B), (11B-1) and (11B-2), L1 as the linking group is a divalent or trivalent residue derived from any one of benzene, biphenyl, terphenyl, naphthalene and phenanthrene.

[0436] Also preferably, in the general formula (1B), a is 1 or 2, and L1 is a divalent or trivalent linking group.

[0437] Also preferably, in the general formula (1B), a is 1, L1 is a linking group, and L1 as the linking group is a divalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a divalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0438] Also preferably, in the general formula (1B), a is 2, L1 is a linking group, and L1 as the linking group is a trivalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a trivalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0439] In the general formula (1B), L1 is also preferably a single bond.

[0440] In the general formula (2B), it is also preferred that X 13 or X 16 is a carbon atom bonded to L1.

[0441] In the general formula (2B), Y1 is preferably NR 18 , an oxygen atom, a sulfur atom, CR 14 R 15 , or a nitrogen atom bonded to L1.

[0442] In the general formula (2B), Y1 is also preferably CR 14 R 15 .

[0443] When Y1 is CR 14 R 15 , it is preferred that any one of X 11 ~X 18 is a carbon atom bonded to L1, and the other X 11 ~X 18 are nitrogen atoms or CR 13 .

[0444] In the general formula (2B), Y1 is also preferably NR 18 or a nitrogen atom bonded to L1. When Y1 is NR 18 , it is preferred that any one of X 11 ~X 18 is a carbon atom bonded to L1, and the other X 11 ~X 18 are nitrogen atoms or CR 13 . When Y1 is a nitrogen atom bonded to L1, it is preferred that X 11~X 18 are each independently a nitrogen atom or CR 13 .

[0445] In addition, in the general formula (2B), Y1 is also preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0446] It is also preferred that in the general formula (2B), Y1 is an oxygen atom or a sulfur atom,

[0447] X 11 ~X 18 one of which is a carbon atom bonded to L1, and the rest are CR 13 .

[0448] Even more preferably, in the general formula (2B), Y1 is an oxygen atom, X 11 and X 18 are CR 13 , X 12 ~X 17 one of which is a carbon atom bonded to L1, and the rest are CR 13 .

[0449] Preferably, in the general formula (B), any two or three of X1 to X3 are nitrogen atoms.

[0450] When two of X1 to X3 are nitrogen atoms, it is preferred that X1 and X2 are nitrogen atoms and X3 is CR1.

[0451] More preferably, in the general formula (B), 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).

[0452] [Chemical formula 34]

[0453]

[0454] In the general formula (21), A, Ar1, and Ar2 are respectively synonymous with A, Ar1, and Ar2 in the general formula (B).

[0455] · Manufacturing method of the compound represented by the general formula (B)

[0456] The compound represented by the general formula (B) can be produced by a known method.

[0457] Specific examples of the compound represented by the general formula (B) are shown below. In addition, the compound represented by the general formula (B) in the present invention is not limited to these specific examples.

[0458] [Chemical formula 35]

[0459]

[0460] [Chemical Formula 36]

[0461]

[0462] [Chemical Formula 37]

[0463]

[0464] [Chemical Formula 38]

[0465]

[0466] [Chemical Formula 39]

[0467]

[0468] [Chemical Formula 40]

[0469]

[0470] [Chemical Formula 41]

[0471]

[0472] [Chemical Formula 42]

[0473]

[0474] [Chemical Formula 43]

[0475]

[0476] [Chemical Formula 44]

[0477]

[0478] [Chemical Formula 45]

[0479]

[0480] <Light-emitting layer>

[0481] The light-emitting layer 5 contains a first compound, a second compound, and a third compound.

[0482] (The first compound)

[0483] The first compound is a fluorescent compound. The first compound can also be a delayed fluorescence compound, or a compound that does not exhibit delayed fluorescence.

[0484] In this embodiment, the first compound is a compound represented by the following general formula (1).

[0485] · The compound represented by the general formula (1)

[0486] [Chemical 46]

[0487]

[0488] In the general formula (1),

[0489] X is a nitrogen atom or a carbon atom bonded to Y,

[0490] Y is a hydrogen atom or a substituent,

[0491] R 21 ~R 26 are each independently a hydrogen atom or a substituent, or a group of R 21 and R 22 forms a ring by bonding to each other, a group of R 22 and R 23 forms a ring by bonding to each other, a group of R 24 and R 25 forms a ring by bonding to each other, and any one or more groups of R 25 and R 26 form a ring by bonding to each other.

[0492] Y and R as substituents 21 ~R 26 are each independently selected from

[0493] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0494] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0495] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0496] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0497] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0498] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms,

[0499] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0500] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0501] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0502] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0503] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0504] A heteroaryl group having 5 to 30 ring-forming atoms, which may or may not be substituted,

[0505] a halogen atom,

[0506] a carboxyl group,

[0507] an ester group which may or may not be substituted,

[0508] a carbamoyl group which may or may not be substituted,

[0509] an amino group which may or may not be substituted,

[0510] a nitro group,

[0511] a cyano group,

[0512] a silyl group which may or may not be substituted, and

[0513] a siloxanyl group which may or may not be substituted are selected from the group consisting of,

[0514] Z 21 and Z 22 are each independently a substituent, or Z 21 and Z 22 are bonded to each other to form a ring, and Z as a substituent 21 and Z 22 are each independently selected from

[0515] a halogen atom,

[0516] an alkyl group having 1 to 30 carbon atoms which may or may not be substituted,

[0517] a haloalkyl group having 1 to 30 carbon atoms which may or may not be substituted,

[0518] an aryl group having 6 to 30 ring-forming carbon atoms which may or may not be substituted,

[0519] an alkoxy group having 1 to 30 carbon atoms which may or may not be substituted,

[0520] a haloalkoxy group having 1 to 30 carbon atoms which may or may not be substituted, and

[0521] an aryloxy group having 6 to 30 ring-forming carbon atoms which may or may not be substituted are selected from the group consisting of.

[0522] In the general formula (1), for example, when the groups of R 25 and R 26 are bonded to each other to form a ring, the first compound is represented by the following general formula (11).

[0523] [Chemical formula 47]

[0524]

[0525] In the general formula (11), X, Y, R 21 ~R 24 , Z 21 and Z 22 respectively with X, Y, R in the general formula (1) 21 ~R 24 , Z 21 and Z 22 Synonymous, R 27 ~R 30 are independently a hydrogen atom or a substituent, and R 27 ~R 30 In the case of a substituent, the substituent is 21 ~R 24 The exemplified substituents have the same meanings.

[0526] In the general formula (1), Z 21 and Z 22 When the two ions are bonded to each other to form a ring, the first compound is represented by, for example, the following general formula (10A) or the following general formula (10B). However, the first compound is not limited to the following structure.

[0527] [Chemistry 48]

[0528]

[0529] In the general formula (10A), X, Y and R 21 ~R 26 respectively with X, Y and R in the general formula (1) 21 ~R 26 Synonymous, R 1A are independently a hydrogen atom or a substituent, and R 1A In the case of a substituent, the substituent is 21 ~R 26 The exemplified substituents have the same meanings, and n3 is 4.

[0530] In the general formula (10B), X, Y and R 21 ~R 26 respectively with X, Y and R in the general formula (1) 21 ~R 26 Synonymous, R 1B are independently a hydrogen atom or a substituent, and R 1B In the case of a substituent, the substituent is 21 ~R 26 The exemplified substituents have the same meanings, and n4 is 4.

[0531] Preferably Z 21 and Z 22 At least one of (preferably Z21 and Z 22 ) is a group selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[0532] More preferably Z 21 and Z 22 At least one of them is a group selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms substituted with a fluorine atom, an aryloxy group having 6 to 30 ring carbon atoms substituted with a fluorine atom, and an aryloxy group having 6 to 30 ring carbon atoms substituted with a fluoroalkyl group having 1 to 30 carbon atoms.

[0533] Even more preferably Z 21 and Z 22 At least one of them is an alkoxy group having 1 to 30 carbon atoms substituted with a fluorine atom, and even more preferably Z 21 and Z 22 is an alkoxy group having 1 to 30 carbon atoms substituted with a fluorine atom.

[0534] Also preferably Z 21 and Z 22 are the same group.

[0535] On the other hand, it is also preferred that at least one of the said Z 21 and the said Z 22 is a fluorine atom, and even more preferably the said Z 21 and the said Z 22 is a fluorine atom.

[0536] Also preferably at least one of the said Z 21 and the said Z 22 is a group represented by the following general formula (10a).

[0537] [Chemical formula 49]

[0538]

[0539] In the general formula (10a), A is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, L2 is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, m is 0, 1, 2, 3, 4, 5, 6 or 7, and when m is 2, 3, 4, 5, 6 or 7, the plurality of L2s are the same as or different from each other. m is preferably 0, 1 or 2. When m is 0, A is directly bonded to O (oxygen atom).

[0540] In the general formula (1), Z 21 and Z 22 When it is a group represented by the general formula (10a), the first compound is a compound represented by the following general formula (12).

[0541] The first compound is also preferably a compound represented by the following general formula (12).

[0542] [Chemical formula 50]

[0543]

[0544] In the general formula (12), X, Y when X is a carbon atom bonded to Y, R 21 ~R 26 are respectively synonymous with X, Y, R 21 ~R 26 in the general formula (1). A 21 and A 22 are synonymous with A in the general formula (10a), and may be the same as or different from each other. L 21 and L 22 are synonymous with L2 in the general formula (10a), and may be the same as or different from each other. m1 and m2 are each 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, the plurality of Ls 21 are the same as or different from each other, and when m2 is 2, 3, 4, 5, 6 or 7, the plurality of Ls 22 are the same as or different from each other. When m1 is 0, A 21 is directly bonded to O (oxygen atom), and when m2 is 0, A 22 is directly bonded to O (oxygen atom).

[0545] At least one of A and L2 in the general formula (10a) is preferably substituted with a halogen atom, more preferably substituted with a fluorine atom.

[0546] A in the general formula (10a) is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms or a perfluoroaryl group having 6 to 12 ring carbon atoms, and further preferably a perfluoroalkyl group having 1 to 6 carbon atoms.

[0547] L2 in the general formula (10a) is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms or a perfluoroarylene group having 6 to 12 ring carbon atoms, and further preferably a perfluoroalkylene group having 1 to 6 carbon atoms.

[0548] That is, the first compound is also preferably a compound represented by the following general formula (12a).

[0549] [Chemical Formula 51]

[0550]

[0551] In the general formula (12a),

[0552] X is synonymous with X in the general formula (1). When X is a carbon atom bonded to Y, Y is synonymous with Y in the general formula (1).

[0553] R 21 ~R 26 are each independently synonymous with R 21 ~R 26 in the general formula (1),

[0554] m3 is 0 or more and 4 or less.

[0555] m4 is 0 or more and 4 or less.

[0556] m3 and m4 may be the same or different from each other.

[0557] In the general formulas (1), (11), (12), and (12a),

[0558] X is a carbon atom bonded to Y.

[0559] Y is a hydrogen atom or a substituent.

[0560] Y as the substituent is preferably a substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0561] In the general formulas (1), (11), (12), and (12a),

[0562] As a more preferred embodiment, the following embodiments can be exemplified:

[0563] X is a carbon atom bonded to Y.

[0564] Y is a hydrogen atom or a substituent,

[0565] When Y is a substituent, it is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0566] When Y as a substituent is a substituted aryl group having 6 to 30 ring carbon atoms, the substituent is,

[0567] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0568] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0569] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0570] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, or

[0571] an aryl group having 6 to 30 ring carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms.

[0572] In the first compound, the Z 21 and the Z 22 may bond to each other to form a ring, but preferably the Z 21 and the Z 22 do not bond to each other to form a ring.

[0573] In the general formulas (1), (12), and (12a), preferably at least one of R 21 , R 23 , R 24 , and R 26 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.

[0574] In the general formulas (1), (12), and (12a), more preferably R 21 , R 23 , R 24 , and R 26 are 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, preferably R 22 and R 25 are hydrogen atoms.

[0575] In the general formulas (1), (12), and (12a), preferably R 21 , R 23 , R 24 , and R 26At least any one of them is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0576] In the general formulas (1), (12), and (12a), it is more preferable that R 21 , R 23 , R 24 , and R 26 are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms. In this case, it is preferable that R 22 and R 25 are hydrogen atoms.

[0577] In the general formulas (1), (12), and (12a),

[0578] As a more preferable embodiment, the following embodiments can be cited:

[0579] R 21 , R 23 , R 24 , and R 26 are each independently

[0580] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[0581] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[0582] an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) substituted with an alkyl group having 1 to 30 carbon atoms,

[0583] R 22 and R 25 are hydrogen atoms.

[0584] In the general formula (11), it is preferable that at least any one of R 21 , R 23 , and R 24 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.

[0585] In the general formula (11), it is more preferable that R 21 , R 23 , and R 24 are 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, it is preferable that R 22 is a hydrogen atom.

[0586] In the general formula (11), it is preferable that R 21 , R 23 , and R 24At least any one of them is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0587] In the general formula (11), it is more preferable that R 21 , R 23 and R 24 are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms. In this case, it is preferable that R 22 is a hydrogen atom.

[0588] In the general formula (11),

[0589] As a more preferable embodiment, the following embodiments can be exemplified:

[0590] R 21 , R 23 and R 24 are each independently

[0591] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[0592] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[0593] an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) substituted with an alkyl group having 1 to 30 carbon atoms,

[0594] R 22 is a hydrogen atom.

[0595] In one embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (n).

[0596] [Chemical formula 52]

[0597]

[0598] (In the general formula (n),

[0599] Ar 1001 and Ar 1002 are each independently selected from the group consisting of

[0600] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and

[0601] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0602] R 1001 to R 1005 are each independently a hydrogen atom or a substituent, or the group of R 1001 and R 1002 , R 1002and Ar 1001 group of, Ar 1002 and R 1003 group of, and also R 1003 and R 1004 any one or more groups among the groups of are bonded to each other to form a ring,

[0603] R as a substituent 1001 ~R 1005 each independently from

[0604] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0605] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0606] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0607] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0608] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0609] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms,

[0610] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0611] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0612] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0613] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0614] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0615] a halogen atom,

[0616] a carboxyl group,

[0617] a substituted or unsubstituted ester group,

[0618] a substituted or unsubstituted carbamoyl group,

[0619] a substituted or unsubstituted amino group,

[0620] a nitro group,

[0621] a cyano group,

[0622] a substituted or unsubstituted silyl group, and

[0623] are selected from the group consisting of a substituted or unsubstituted siloxanyl group,

[0624] Z 1001 and Z 1002 each independently from

[0625] a halogen atom,

[0626] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0627] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0628] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0629] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0630] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0631] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and

[0632] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms. )

[0633] In the general formula (n), preferably Ar 1001 and Ar 1002 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. Ar 1001 and Ar 1002 are each independently a monocyclic or fused ring. As Ar 1001 and Ar 1002 , for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, etc. can be exemplified.

[0634] In the general formula (n), preferably at least one of R 1001 and R 1004 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and more preferably R 1001 and R 1004 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0635] In the general formula (n), R 1002 and R 1003Preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0636] In the general formula (n), R 1005 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. As R 1005 , for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, and a substituted or unsubstituted dibenzofuranyl group, etc. can be cited.

[0637] In the general formula (n), preferably Z 1001 and Z 1002 are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms.

[0638] In the general formula (n), when any one or more groups in the group of R 1002 and Ar 1001 and the group of Ar 1002 and R 1003 are bonded to each other to form a ring, the first compound is preferably a compound represented by the following general formula (n + 1A) or general formula (n + 1B).

[0639] [Chemical formula 53]

[0640]

[0641] (In the general formula (n + 1A), R 1001 , R 1002 , R 1004 , R 1005 , Ar 1001 , Z 1001 and Z 1002 are each independently synonymous with R 1001 , R 1002 , R 1004 , R 1005 , Ar 1001 , Z 1001 and Z 1002 in the general formula (n),

[0642] In the general formula (n + 1B), R1001 , R 1004 , R 1005 , Z 1001 and Z 1002 are each independently synonymous with R, R, R, Z, and Z in the general formula (n), 1001 , R 1004 , R 1005 , Z 1001 and Z 1002 , and

[0643] Ar 1003 and Ar 1004 are each independently selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms which may be substituted or unsubstituted, and an aromatic heterocyclic ring having 5 to 30 ring atoms which may be substituted or unsubstituted, B

[0644] is a crosslinked structure obtained by bonding three or more atoms in series, and the atoms are selected from the group consisting of a substituted or unsubstituted carbon atom,

[0645] a substituted or unsubstituted silicon atom, 1 a substituted or unsubstituted nitrogen atom,

[0646] a substituted or unsubstituted phosphorus atom,

[0647] an oxygen atom, and

[0648] a sulfur atom,

[0649]

[0650]

[0651]

[0652] and C

[0653] is a crosslinked structure obtained by bonding one or more atoms in series, and the atoms are selected from the group consisting of a substituted or unsubstituted carbon atom, 1 a substituted or unsubstituted silicon atom,

[0653] a substituted or unsubstituted nitrogen atom,

[0654] a substituted or unsubstituted phosphorus atom,

[0655] a substituted or unsubstituted nitrogen atom,

[0656] a substituted or unsubstituted phosphorus atom,

[0657] an oxygen atom, and

[0658] a sulfur atom,

[0659] wherein, when B is trimethylene, R is not a hydrogen atom or a halogen atom.) 1 is 1004 not

[0660] Here, in General Formula (n + 1A) and General Formula (n + 1B), the double bond shown as part of Ar 1003 represents a part of an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and represents a carbon atom directly bonded to the pyrromethylene skeleton and a carbon atom adjacent to the carbon atom bonded to the crosslinked structure B 1

[0661] Similarly, in General Formula (n + 1A) and General Formula (n + 1B), the double bond shown as part of Ar 1004 represents a part of an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and represents a carbon atom directly bonded to the pyrromethylene skeleton and a carbon atom adjacent to the carbon atom bonded to the crosslinked structure C 1

[0662] R 1002 and Ar 1001 When the groups of form a ring by bonding to each other, the number of ring-forming atoms, and also Ar 1002 and R 1003 When the groups of form a ring by bonding to each other, the number of ring-forming atoms is preferably 30 or less.

[0663] Specifically, in the said General Formula (n + 1A) and General Formula (n + 1B), the number of atoms (number of serially bonded atoms) in the crosslinked structure B 1 , the number of ring-forming atoms in Ar 1003 , and the total with the carbon atoms (2) constituting the pyrromethylene skeleton are preferably 30 or less.

[0664] In the said General Formula (n + 1B), the number of atoms (number of serially bonded atoms) in the crosslinked structure C 1 , the number of ring-forming atoms in Ar 1004 , and the total with the carbon atoms (2) constituting the pyrromethylene skeleton are preferably 30 or less.

[0665] In the said General Formula (n + 1A) and General Formula (n + 1B), B 1 is preferably a crosslinked structure represented by the following General Formula (n + 2A) or General Formula (n + 2B).

[0666] [Chemical Formula 54]

[0667]

[0668] (In the said General Formula (n + 2A), R 1011 to R 1016 are each independently a hydrogen atom or a substituent, or one or more groups formed by two or more adjacent ones among R 1011 to R 1016 bond to each other to form a ring,

[0669] ​​In the general formula (n + 2B), R 1011 ~R 1014 are each independently a hydrogen atom or a substituent, or one or more groups formed by bonding together two or more adjacent ones of R 1011 ~R 1014 bond to each other to form a ring,

[0670] As the substituent, R 1011 ~R 1016 are each independently,

[0671] an alkyl group having 1 to 30 carbon atoms which may or may not be substituted,

[0672] a halogenated alkyl group having 1 to 30 carbon atoms which may or may not be substituted,

[0673] a cycloalkyl group having 3 to 30 ring-constituting carbon atoms which may or may not be substituted,

[0674] an aryl group having 6 to 30 ring-constituting carbon atoms which may or may not be substituted,

[0675] a heteroaryl group having 5 to 30 ring-constituting atoms which may or may not be substituted,

[0676] an alkoxy group having 1 to 30 carbon atoms which may or may not be substituted,

[0677] a halogenated alkoxy group having 1 to 30 carbon atoms which may or may not be substituted,

[0678] an alkylthio group having 1 to 30 carbon atoms which may or may not be substituted,

[0679] an aryloxy group having 6 to 30 ring-constituting carbon atoms which may or may not be substituted,

[0680] an arylthio group having 6 to 30 ring-constituting carbon atoms which may or may not be substituted,

[0681] an alkenyl group having 2 to 30 carbon atoms which may or may not be substituted,

[0682] an alkynyl group having 2 to 30 carbon atoms which may or may not be substituted,

[0683] a halogen atom,

[0684] a carboxyl group,

[0685] an amino group which may or may not be substituted,

[0686] a nitro group,

[0687] a cyano group,

[0688] a silyl group which may or may not be substituted,

[0689] a hydroxyl group,

[0690] an ester group,

[0691] a siloxanyl group, or

[0692] a carbamoyl group,

[0693] * represents the connecting portion to the pyrrole ring in the general formula (n + 1A) and the general formula (n + 1B), and ** represents the connecting portion to Ar 1003 .)

[0694] In addition, * representing the connecting portion to the pyrrole ring corresponds to 2* in the general formula (n + 1A) and the general formula (n + 1B), and ** representing the connecting portion to Ar 1003 corresponds to 1* in the general formula (n + 1A) and the general formula (n + 1B).

[0695] In the general formula (n + 2A) and the general formula (n + 2B), preferably, R 1011 ~R 1016 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0696] ·B 1 (a crosslinked structure obtained by connecting three or more atoms in series)

[0697] In the general formula (n + 1A) and the general formula (n + 1B), B 1 is preferably a crosslinked structure obtained by connecting three or more atoms in series.

[0698] ·C 1 (a crosslinked structure obtained by connecting one or more atoms in series)

[0699] In the general formula (n + 1B), C 1 is preferably a crosslinked structure obtained by connecting one to three atoms in series.

[0700] The atoms constituting C 1 are preferably selected from substituted or unsubstituted carbon atoms, oxygen atoms, and sulfur atoms, and more preferably substituted or unsubstituted carbon atoms.

[0701] In the general formula (n), R 1005 is preferably a group represented by the following general formula (n + 3).

[0702] [Chemical formula 55]

[0703]

[0704] (In the general formula (n + 3),

[0705] R 1021 and R 1022 are each independently selected from

[0706] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0707] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0708] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0709] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and

[0710] is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0711] R 1023 ~R 1025 are each independently a hydrogen atom or a substituent, or R 1023 and R 1024 in the group of, and R 1024 and R 1025 any one or more groups in the group bond to each other to form a ring,

[0712] R as a substituent 1023 ~R 1025 are each independently,

[0713] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0714] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0715] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0716] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0717] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0718] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0719] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms,

[0720] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0721] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0722] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0723] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0724] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0725] A substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms,

[0726] A substituted or unsubstituted arylcarbonyl group having 6 to 30 ring-constituting carbon atoms,

[0727] A substituted or unsubstituted acyl group having 1 to 30 carbon atoms,

[0728] A halogen atom,

[0729] A carboxyl group,

[0730] A substituted or unsubstituted amino group,

[0731] A nitro group,

[0732] A cyano group,

[0733] A substituted or unsubstituted silyl group,

[0734] A hydroxyl group,

[0735] An ester group,

[0736] A siloxanyl group, or

[0737] A carbamoyl group,

[0738] In the general formula (n + 3), *** represents the position where it is bonded to the carbon atom to which R in the general formula (n) is bonded. ) 1005

[0739] In the general formula (n + 3), preferably, R 1021 and R 1022 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-constituting carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-constituting atoms. When R 1021 and R 1022 are alkyl groups, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms is more preferred, and methyl is further preferred. When R 1021 and R 1022 are aryl groups, a substituted or unsubstituted phenyl group is more preferred. When R 1021 and R 1022 are heteroaryl groups, a substituted or unsubstituted monocyclic heteroaryl group having 5 to 6 ring-constituting atoms is more preferred.

[0740] In the general formula (n + 3), more preferably, R 1023 to R 1025 ​Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a halogen atom, a substituted or unsubstituted amino group, or a cyano group.

[0741] In the general formula (n), the general formula (n + 1A), the general formula (n + 1B), and the general formula (n + 3), the substituent in the case of "substituted or unsubstituted" is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted acyl group having 1 to 30 carbon atoms, a halogen atom, a carboxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted phosphoryl group, a hydroxyl group, a substituted phosphino group, an ester group, a siloxanyl group, or a carbamoyl group.

[0742] In the general formula (n), the general formula (n + 1A), the general formula (n + 1B), and the general formula (n + 3), the substituent in the case of "substituted or unsubstituted" is more preferably an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted haloalkyl group having 1 to 30 carbon atoms, an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heteroaryl group having 5 to 30 ring atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted haloalkoxy group having 1 to 30 carbon atoms, an unsubstituted alkylthio group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an unsubstituted arylthio group having 6 to 30 ring carbon atoms, an unsubstituted alkenyl group having 2 to 30 carbon atoms, an unsubstituted alkynyl group having 2 to 30 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, an unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms, an unsubstituted acyl group having 1 to 30 carbon atoms, a halogen atom, a carboxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted phosphoryl group, a hydroxyl group, a substituted phosphino group, an ester group, a siloxanyl group, or a carbamoyl group.

[0743] In the first compound, examples of the alkoxy group substituted with a fluorine atom 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-undecafluorohexyloxy, 2,3-bis(trifluoromethyl)-2,3-butanedioxy, 1,1,2,2-tetra(btrifluoromethyl)ethenyloxy, 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-tridecafluorononane-1,2-dioxy.

[0744] In the first compound, examples of the aryloxy group substituted with a fluorine atom or the aryloxy group substituted with a fluoroalkyl group include pentafluorophenoxy, 3,4,5-trifluorophenoxy, 4-trifluoromethylphenoxy, 3,5-bis(trifluoromethyl)phenoxy, 3-fluoro-4-trifluoromethylphenoxy, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy, 4-fluorocatecholyl, 4-trifluoromethylcatecholyl, and 3,5-bis(trifluoromethyl)catecholyl.

[0745] When the first compound is a fluorescent compound, the first compound preferably emits light with a main peak wavelength of 400 nm or more and 700 nm or less.

[0746] In this specification, the main peak wavelength refers to the peak wavelength of the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 -6 mol / L or more and 10 -5 mol / L or less, and the emission intensity in the fluorescence spectrum reaches the maximum. The measuring device uses a spectrofluorometer (manufactured by Hitachi High-Technologies Corporation, F-7000).

[0747] The first compound preferably emits red light or green light.

[0748] In this specification, red light emission means light emission with a main peak wavelength of the fluorescence spectrum in the range of 600 nm or more and 660 nm or less.

[0749] 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 further preferably 610 nm or more and 630 nm or less.

[0750] In this specification, green light emission means light emission with a main peak wavelength of the fluorescence spectrum in the range of 500 nm or more and 560 nm or less.

[0751] 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 further preferably 510 nm or more and 530 nm or less.

[0752] In this specification, blue light emission means light emission with a main peak wavelength of the fluorescence spectrum in the range of 430 nm or more and 480 nm or less.

[0753] 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.

[0754] · Method for manufacturing the first compound

[0755] The first compound can be manufactured by a known method.

[0756] The following shows specific examples of the first compound (the compound represented by the general formula (1)) of the present embodiment. In addition, the first compound in the present invention is not limited to these specific examples.

[0757] In addition, the coordination bond between the boron atom and the nitrogen atom in the pyrromethane skeleton can be marked in various ways such as solid lines, dashed lines, arrows, or omission. In this specification, it is represented by a solid line, or a dashed line, or omitted from the description. Me represents a methyl group.

[0758] [Chemical formula 56]

[0759]

[0760] [Chemical formula 57]

[0761]

[0762] [Chemical formula 58]

[0763]

[0764] [Chemical formula 59]

[0765]

[0766] [Chemical formula 60]

[0767]

[0768] [Chemical formula 61]

[0769]

[0770] [Chemical formula 62]

[0771]

[0772] [Chemical formula 63]

[0773]

[0774] [Chemical formula 64]

[0775]

[0776] [Chemical formula 65]

[0777]

[0778] [Chemical formula 66]

[0779]

[0780] [Chemical formula 67]

[0781]

[0782] [Chemical formula 68]

[0783]

[0784] [Chemical Formula 69]

[0785]

[0786] [Chemical Formula 70]

[0787]

[0788] [Chemical Formula 71]

[0789]

[0790] [Chemical Formula 72]

[0791]

[0792] [Chemical Formula 73]

[0793]

[0794] [Chemical Formula 74]

[0795]

[0796] [Chemical Formula 75]

[0797]

[0798] [Chemical Formula 76]

[0799]

[0800] [Chemical Formula 77]

[0801]

[0802] [Chemical Formula 78]

[0803]

[0804] [Chemical Formula 79]

[0805]

[0806] [Chemical Formula 80]

[0807]

[0808] [Chemical Formula 81]

[0809]

[0810] [Chemical Formula 82]

[0811]

[0812] [Chemical Formula 83]

[0813]

[0814] [Chemical Formula 84]

[0815]

[0816] [Chemical Formula 85]

[0817]

[0818] [Chemical Formula 86]

[0819]

[0820] [Chemical Formula 87]

[0821]

[0822] [Chemical Formula 88]

[0823]

[0824] [Chemical Formula 89]

[0825]

[0826] [Chemical Formula 90]

[0827]

[0828] [Chemical Formula 91]

[0829]

[0830] [Chemical Formula 92]

[0831]

[0832] [Chemical Formula 93]

[0833]

[0834] [Chemical Formula 94]

[0835]

[0836] [Chemical Formula 95]

[0837]

[0838] [Chemical Formula 96]

[0839]

[0840] [Chemical Formula 97]

[0841]

[0842] [Chemical Formula 98]

[0843]

[0844] [Chemical Formula 99]

[0845]

[0846] [Chemical Formula 100]

[0847]

[0848] [Chemical Formula 101]

[0849]

[0850] [Chemical Formula 102]

[0851]

[0852] [Chemical Formula 103]

[0853]

[0854] [Chemical Formula 104]

[0855]

[0856] [Chemical Formula 105]

[0857]

[0858] [Chemical Formula 106]

[0859]

[0860] [Chemical Formula 107]

[0861]

[0862] [Chemical Formula 108]

[0863]

[0864] [Chemical Formula 109]

[0865]

[0866] [Chemical Formula 110]

[0867]

[0868] [Chemical Formula 111]

[0869]

[0870] [Chemical Formula 112]

[0871]

[0872] [Chemical Formula 113]

[0873]

[0874] [Chemical Formula 114]

[0875]

[0876] [Chemical Formula 115]

[0877]

[0878] (Second Compound)

[0879] The second compound is a compound with delayed fluorescence properties.

[0880] In the present embodiment, the second compound is a compound represented by the following general formula (2).

[0881] ·Compound represented by general formula (2)

[0882] [Chemical Formula 116]

[0883]

[0884] In the general formula (2), D1 is a group represented by the following general formula (2-1), D2 is a group represented by the following general formula (2-2), and multiple D2s are groups that are identical to each other.

[0885] "Multiple D2s are groups that are identical to each other" means that the variables represented by the same symbol within the general formula (2-2) are all identical to each other.

[0886] "The variables within the general formula (2-2)" refer to R 161 ~R 168 . Specifically, in the group represented by the general formula (2-2) that represents D2 in the general formula (2), R 161 are identical to each other, R 162 are identical to each other, R 163 are identical to each other, R 164 are identical to each other, R 165 are identical to each other, R 166 are identical to each other, R 167 are identical to each other, R 168 are identical to each other. That is, the three D2s in the general formula (2) are groups that are identical to each other including substituents.

[0887] [Chemical formula 117]

[0888]

[0889] In the general formula (2-1), X4 is an oxygen atom or a sulfur atom, and R 131 ~R 140 are each independently a hydrogen atom or a substituent,

[0890] As the substituents, R 131 ~R 140 are each independently,

[0891] an aryl group having 6 to 14 ring carbon atoms, which may or may not be substituted,

[0892] a heterocyclic group having 5 to 14 ring atoms, which may or may not be substituted,

[0893] an alkyl group having 1 to 6 carbon atoms, which may or may not be substituted,

[0894] an alkylsilyl group having 3 to 6 carbon atoms, which may or may not be substituted,

[0895] an alkoxy group having 1 to 6 carbon atoms, which may or may not be substituted,

[0896] an aryloxy group having 6 to 14 ring carbon atoms, which may or may not be substituted,

[0897] an alkylamino group having 2 to 12 carbon atoms, which may or may not be substituted,

[0898] an alkylthio group having 1 to 6 carbon atoms, which may or may not be substituted, or

[0899] an arylthio group having 6 to 14 ring carbon atoms, which may or may not be substituted.

[0900] * indicates the position bonded to the benzene ring in the general formula (2).

[0901] [Chemical formula 118]

[0902]

[0903] In the general formula (2-2), R 161 ~R 168 are each independently a hydrogen atom or a substituent,

[0904] As the substituents, R 161 ~R 168 are each independently,

[0905] a halogen atom,

[0906] an aryl group having 6 to 14 ring carbon atoms, which may or may not be substituted,

[0907] A heterocyclic group having 5 to 14 ring-forming atoms, which may or may not be substituted,

[0908] An alkyl group having 1 to 6 carbon atoms, which may or may not be substituted,

[0909] A haloalkyl group having 1 to 30 carbon atoms, which may or may not be substituted,

[0910] An alkylsilyl group having 3 to 6 carbon atoms, which may or may not be substituted,

[0911] An alkoxy group having 1 to 6 carbon atoms, which may or may not be substituted,

[0912] An aryloxy group having 6 to 14 ring-forming carbon atoms, which may or may not be substituted,

[0913] An alkylamino group having 2 to 12 carbon atoms, which may or may not be substituted,

[0914] An alkylthio group having 1 to 6 carbon atoms, which may or may not be substituted, or

[0915] An arylthio group having 6 to 14 ring-forming carbon atoms, which may or may not be substituted.

[0916] * Each independently represents the position bonded to the benzene ring in the general formula (2).

[0917] In the general formula (2-1), X4 is preferably a sulfur atom.

[0918] In the general formula (2-1), X4 is also preferably an oxygen atom.

[0919] In the second compound, the group represented by the general formula (2-2) is preferably any one of the groups represented by the following general formulas (2-20) to (2-26).

[0920] [Chemical formula 119]

[0921]

[0922] In the general formulas (2-20) to (2-26), * each independently represents the position bonded to the benzene ring in the general formula (2).

[0923] In the general formula (2-2), it is preferred that R 161 ~R 168 are each independently a hydrogen atom, an aryl group having 6 to 14 ring-forming carbon atoms which may or may not be substituted, or an alkyl group having 1 to 6 carbon atoms which may or may not be substituted, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may or may not be substituted.

[0924] In the general formula (2-2), it is also preferred that R 161 , R 163 , R 166 and R168 At least any one of them has a substituent, which is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 162 , R 164 , R 165 and R 167 is a hydrogen atom.

[0925] In the general formulas (2-1) and (2-2), preferably, as substituents, R 131 to R 140 and R 161 to R 168 are independently a halogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted haloalkyl group having 1 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0926] In the general formulas (2-1) and (2-2), preferably, R 131 to R 140 and R 161 to R 168 are independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. More preferably, they are a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Further preferably, they are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0927] In the general formulas (2-1) and (2-2), more preferably, as substituents, R 131 to R 140 and R 161 to R 168 are independently an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0928] In the general formula (2-1), it is further preferred that R 137 is a substituent, and as the substituent, R 137 is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 131 to R 136 and R 138~R 140 is a hydrogen atom.

[0929] In the general formulas (2-1) and (2-2), it is also preferable that R 131 ~R 140 and R 161 ~R 168 are hydrogen atoms.

[0930] · Method for manufacturing the second compound

[0931] The second compound can be manufactured, for example, by the method described in the following examples. The second compound of the present embodiment can be manufactured by imitating the reaction described in the following examples and using known alternative reactions and raw materials that match the target product.

[0932] Specific examples of the second compound (compound represented by the general formula (2)) of the present embodiment are shown below. In addition, the second compound in the present invention is not limited to these specific examples. Me represents methyl.

[0933] [Chemical formula 120]

[0934]

[0935] [Chemical formula 121]

[0936]

[0937] [Chemical formula 122]

[0938]

[0939] [Chemical formula 123]

[0940]

[0941] [Chemical formula 124]

[0942]

[0943] · Delayed fluorescence

[0944] Regarding delayed fluorescence, it is explained on pages 261 to 268 of "Device Physical Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). In this document, it is explained that if the energy difference △E between the excited singlet state and the excited triplet state of the fluorescent material can be reduced 13, the reverse energy transfer from the triplet excited state with a low transfer probability to the singlet excited state usually occurs efficiently, generating thermally activated delayed fluorescence (TADF). Further, the mechanism of delayed fluorescence generation is illustrated by FIG. 10.38 in this document. The second compound in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0945] Generally, the luminescence of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0946] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurement. Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it and measuring the decay behavior (transient characteristics) of the PL luminescence after the irradiation is stopped. The PL luminescence in a TADF material is divided into a luminescence component from singlet excitons generated by the initial PL excitation and a luminescence component from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the luminescence from these singlet excitons rapidly decays after the pulsed laser is irradiated.

[0947] On the other hand, delayed fluorescence is the luminescence from singlet excitons generated via triplet excitons with a long lifetime, so it decays slowly. Thus, there is a large time difference between the luminescence from singlet excitons generated by the initial PL excitation and the luminescence from singlet excitons generated via triplet excitons. Therefore, the luminescence intensity derived from delayed fluorescence can be obtained.

[0948] Figure 2 FIG. shows a schematic diagram of an example device for measuring transient PL. An example of the measurement method of transient PL using Figure 2 and the analysis of the behavior of delayed fluorescence will be described.

[0949] Figure 2 The transient PL measurement device 100 of Figure 2 includes: a pulsed laser unit 101 that can irradiate light with a specified wavelength; a sample chamber 102 that houses the measurement sample; a spectroscope 103 that spectroscopes the light emitted from the measurement sample; a streak camera 104 that is used to image a two-dimensional image; and a personal computer 105 that reads and analyzes the two-dimensional image. In addition, the measurement of transient PL is not limited to the device described in

[0950] The sample housed in the sample chamber 102 can be obtained by forming a film of a thin film doped with a doping material at a concentration of 12% by mass with respect to a matrix material on a quartz substrate.

[0951] For the thin-film sample stored in the sample chamber 102, pulsed laser is irradiated from the pulsed laser unit 101 to excite the doping material. Luminescence is extracted in a direction 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is spectroscopically analyzed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to the luminescence intensity. If this two-dimensional image is cut out on a specified time axis, a luminescence spectrum with the vertical axis being the luminescence intensity and the horizontal axis being the wavelength can be obtained. In addition, if this two-dimensional image is cut out along the wavelength axis, a decay curve (transient PL) with the vertical axis being the logarithm of the luminescence intensity and the horizontal axis being the time can be obtained.

[0952] For example, the following reference compound H1 was used as the matrix material, and the following reference compound D1 was used as the doping material. The thin-film sample A was fabricated as described above, and transient PL measurement was performed.

[0953] [Chemical formula 125]

[0954]

[0955] Here, the decay curve was analyzed using the above-mentioned thin-film sample A and thin-film sample B. For the thin-film sample B, the following reference compound H2 was used as the matrix material, and the above-mentioned reference compound D1 was used as the doping material. The thin-film sample was fabricated as described above.

[0956] Figure 3 The decay curves obtained from the transient PL measurements of the thin-film sample A and thin-film sample B are shown.

[0957] [Chemical formula 126]

[0958]

[0959] As described above, through transient PL measurement, a luminescence decay curve with the luminescence intensity on the vertical axis and the time on the horizontal axis can be obtained. Based on this luminescence decay curve, the fluorescence intensity ratio of the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In a material with delayed fluorescence properties, the proportion of the intensity of the slowly decaying delayed fluorescence is relatively large compared to the intensity of the rapidly decaying fluorescence.

[0960] Specifically, as the luminescence from the material with delayed fluorescence, there is Prompt luminescence (instantaneous luminescence) and Delay luminescence (delayed luminescence). Prompt luminescence (instantaneous luminescence) refers to the luminescence immediately observed from the excited state after being excited by pulsed light (light irradiated by pulsed laser) with a wavelength absorbed by the material with delayed fluorescence. Delay luminescence (delayed luminescence) refers to the luminescence that cannot be immediately observed after being excited by the pulsed light but is observed thereafter.

[0961] The amounts of Prompt luminescence and Delay luminescence and the ratio between the two can be obtained by the same method as the method described in "Nature 492, 234 - 238, 2012" (Reference 1). In addition, the device for calculating the amounts of Prompt luminescence and Delay luminescence is not limited to the device described in the above Reference 1 or Figure 2 the device described therein.

[0962] In addition, in this specification, a sample prepared by the method shown below is used in the measurement of the delayed fluorescence of the second compound. For example, the second compound is dissolved in toluene, and in order to eliminate the influence of self - absorption, a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared. In addition, in order to prevent quenching caused by oxygen, after the sample solution is frozen and degassed, it is sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen - free sample solution saturated with argon.

[0963] The fluorescence spectrum of the above - mentioned sample solution is measured using a spectrofluorometer FP - 8600 (manufactured by JASCO Corporation), and in addition, the fluorescence spectrum of an ethanol solution of 9,10 - diphenylanthracene is measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield is calculated according to Equation (1) in Morris et al., "J. Phys. Chem.", 80 (1976) 969.

[0964] In this embodiment, when the amount of Prompt luminescence (instantaneous luminescence) of the compound to be measured (the second compound) is denoted as X P and the amount of Delay luminescence (delayed luminescence) is denoted as X D , X D / X P is preferably 0.05 or more.

[0965] The measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio between the two for compounds other than the second compound in this specification is the same as the measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio between the two for the second compound.

[0966] (Third compound)

[0967] The third compound may be a compound with thermally activated delayed fluorescence property or a compound without thermally activated delayed fluorescence property, and preferably a compound without thermally activated delayed fluorescence property.

[0968] In this embodiment, the third compound is a compound represented by the following general formula (3).

[0969] · The compound represented by the general formula (3)

[0970] [Chemical formula 127]

[0971]

[0972] In the general formula (3), A 31 is a group represented by the following general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e) or general formula (31f),

[0973] R 31 ~R 38 are each independently a hydrogen atom or a substituent, and R 401 ~R 404 and R 409 ~R 412 are each independently a hydrogen atom or a substituent,

[0974] As the substituent, R 31 ~R 38 and as the substituent, R 401 ~R 404 and R 409 ~R 412 are each independently

[0975] a halogen atom,

[0976] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0977] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0978] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0979] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0980] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0981] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0982] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0983] A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0984] A substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0985] A hydroxyl group,

[0986] A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0987] A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0988] An amino group,

[0989] A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0990] A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0991] A mercapto group,

[0992] A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0993] A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms.

[0994] [Chemical formula 128]

[0995]

[0996] [Chemical formula 129]

[0997]

[0998] [Chemical formula 130]

[0999]

[1000] In the general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e), and general formula (31f),

[1001] R 310 ~R 319 Are each independently a hydrogen atom or a substituent,

[1002] R 320 ~R 329 Are each independently a hydrogen atom or a substituent,

[1003] R 330 ~R 339 Are each independently a hydrogen atom or a substituent,

[1004] R 340 ~R 349are each independently a hydrogen atom or a substituent,

[1005] R 350 ~R 359 are each independently a hydrogen atom or a substituent,

[1006] R 360 ~R 369 are each independently a hydrogen atom or a substituent,

[1007] R as a substituent 310 ~R 319 、R 320 ~R 329 、R 330 ~R 339 、R 340 ~R 349 、R 350 ~R 359 and R 360 ~R 369 are each independently synonymous with R as a substituent in the general formula (3). *Each independently represents the position bonded to the benzene ring having R 31 ~R 38 and R as a substituent 401 ~R 404 and R 409 ~R 412 in the general formula (3). 401 ~R 404 in the general formula (3).

[1008] ·Method for manufacturing the third compound

[1009] The third compound (the compound represented by the general formula (3)) can be manufactured, for example, by the method described in the examples below. The third compound of the present embodiment can be manufactured by imitating the reaction described in the examples below and using known alternative reactions and raw materials that match the target product.

[1010] ·Specific examples of the third compound

[1011] Specific examples of the third compound (the compound represented by the general formula (3)) of the present embodiment are shown below. In addition, the third compound in the present invention is not limited to these specific examples.

[1012] [Chemical formula 131]

[1013]

[1014] <Relationship among the first compound, the second compound, and the third compound in the light-emitting layer>

[1015] In the organic EL element 1 of the present embodiment, the singlet energy S1(M1) of the first compound, the singlet energy S1(M2) of the second compound, and the singlet energy S1(M3) of the third compound in the light-emitting layer 5 satisfy the relationship of the following mathematical formula (Equation 1).

[1016] S1(M3)>S1(M2)>S1(M1)…(Equation 1)

[1017] The energy gap T 77K (M1) of the first compound at 77 [K] in the light-emitting layer 5 and the energy gap T 77K (M2) of the second compound at 77 [K] and the energy gap T 77K (M3) of the third compound at 77 [K] preferably satisfy the relationship of the following mathematical formula (Equation 2).

[1018] T 77K (M3)>T 77K (M2)>T 77K (M1)…(Equation 2)

[1019] In the present embodiment, the difference △ST(M2) between the singlet energy S1(M2) of the second compound and the energy gap T 77K (M2) of the second compound at 77 [K] preferably satisfies any one of the relationships of the following mathematical formulas (Equation 1A) to (Equation 1D).

[1020] △ST(M2)=S1(M2)-T 77K (M2)<0.3eV (Equation 1A)

[1021] △ST(M2)=S1(M2)-T 77K (M2)<0.2eV (Equation 1B)

[1022] △ST(M2)=S1(M2)-T 77K (M2)<0.1eV (Equation 1C)

[1023] △ST(M2)=S1(M2)-T 77K (M2)<0.01eV (Equation 1D)

[1024] In the present embodiment, the difference △ST(M1) between the singlet energy S1(M1) of the first compound and the energy gap T 77K (M1) of the first compound at 77 [K] preferably satisfies the relationship of the following mathematical formula (Equation 1E).

[1025] △ST(M1)=S1(M1)-T 77K (M1)>0.3 [eV]…(Equation 1E)

[1026] In the present embodiment, the singlet energy S1(M3) of the third compound and the energy gap T 77K (M3) of the third compound at 77 [K] preferably satisfy the relationship of the following mathematical formula (Formula 1F).

[1027] △ST(M3) = S1(M3) - T 77K (M3) > 0.3 [eV] … (Formula 1F)

[1028] In the present embodiment, the energy gap T 77K (M3) of the third compound at 77 [K] is preferably 2.9 eV or more. It is considered that by making the third compound have such an energy gap T 77K (M3), in the light-emitting layer, the triplet energy of the second compound (delayed fluorescence compound) can be effectively confined in the light-emitting layer.

[1029] · TADF mechanism

[1030] In the organic EL element 1 of the present embodiment, a compound having a small △ST(M2) is preferably used as the second compound, and reverse intersystem crossing from the triplet energy level of the second compound to the singlet energy level of the second compound easily occurs by the heat energy given from the outside. The energy state transformation mechanism in which the excited triplet state of the exciton obtained by electrical excitation inside the organic EL element is spin-exchanged to the excited singlet state by reverse intersystem crossing is called the TADF mechanism.

[1031] Figure 4 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-emitting layer 5. Figure 4 In the figure, 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 dotted arrow from S1(M2) to S1(M1) in the figure represents Förster-type energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound.

[1032] As Figure 4As shown, if a compound with a smaller ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing from the thermal energy to the lowest excited singlet state S1(M2). And, Förster-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 considered that by utilizing the delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1033] · Relationship between triplet energy and energy gap at 77 [K]

[1034] Here, the relationship between the triplet energy and the energy gap at 77 [K] will be described. In this embodiment, there are differences between the energy gap at 77 [K] and the triplet energy defined commonly.

[1035] The measurement of the triplet energy is carried out as follows. First, the compound to be measured is dissolved in an appropriate solvent, and the resulting solution is sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis: phosphorescence emission intensity, the horizontal axis: wavelength) is measured at a low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of the phosphorescence spectrum, and based on the wavelength value at the intersection of this tangent and the horizontal axis, the triplet energy is calculated according to a specified conversion formula.

[1036] Here, among the compounds of this embodiment, the compound with thermally activated delayed fluorescence property is preferably a compound with a smaller ΔST. If ΔST is smaller, even in the low temperature (77 [K]) state, intersystem crossing and reverse intersystem crossing are likely to occur, 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 the luminescence from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the luminescence comes from, but basically the value of the triplet energy is dominant.

[1037] Therefore, in this embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to strictly distinguish the differences, the value measured as follows is called the energy gap T 77K . The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is added to a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis: phosphorescence emission intensity, the horizontal axis: wavelength) is measured at a low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of the phosphorescence spectrum, and based on the wavelength value λ of the intersection of this tangent and the horizontal axis edge[nm], the energy calculated according to the following conversion formula (F1) is taken as the energy gap T at 77 [K] 77K .

[1038] Conversion formula (F1): T 77K [eV]=1239.85 / λ edge

[1039] The tangent line to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows. Consider that this tangent line is the tangent line at each point on the curve toward the long wavelength side when moving from the short wavelength side of the phosphorescence spectrum to the maximum value of the spectrum on the shortest wavelength side of the spectrum maximum. The slope of this tangent line increases as the curve rises (i.e., as the value on the vertical axis increases). The tangent line drawn at the point where the value of this slope takes the maximum value (i.e., the tangent line at the inflection point) is taken as the tangent line to the rising edge on the short wavelength side of this phosphorescence spectrum.

[1040] In addition, the maximum points with peak intensities below 15% of the maximum peak intensity of the spectrum are not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent line drawn at the point closest to the maximum value on the shortest wavelength side and where the value of the slope takes the maximum value is taken as the tangent line to the rising edge on the short wavelength side of this phosphorescence spectrum.

[1041] The measurement of phosphorescence can use the main body of the F-4500 type spectrofluorometer manufactured by Hitachi High-Technologies Corporation. In addition, the measuring device is not limited to this, and the measurement can be carried out by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[1042] · Singlet energy S1

[1043] As a measurement method (sometimes called the solution method) of the singlet energy S1 using a solution, the following method can be cited.

[1044] Prepare a 10 μmol / L toluene solution of the compound to be measured and add it to a quartz cell, and measure the absorption spectrum of this sample at room temperature (300 K) (assuming the vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy.

[1045] Conversion formula (F2): S1 [eV]=1239.85 / λedge

[1046] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi (device name: U3310) can be cited, but it is not limited to this.

[1047] A tangent line to the descending edge on the long-wavelength side of the absorption spectrum is drawn as follows. Consider this tangent line to be the tangent line at each point on the spectral curve when moving along the long-wavelength direction from the maximum value on the longest-wavelength side of the maximum value of the absorption spectrum. This tangent line repeats the situation where the slope decreases and then increases as the curve descends (i.e., as the value on the vertical axis decreases). The tangent line drawn at the point where the value of the slope takes a minimum value on the longest-wavelength side (where the absorbance reaching 0.1 or less is not included) is taken as the tangent line to the descending edge on the long-wavelength side of this absorption spectrum.

[1048] In addition, the maximum points with an absorbance value of 0.2 or less are not included in the maximum values on the above-mentioned longest-wavelength side.

[1049] In the present embodiment, the singlet energy S1 and the energy gap T at 77 [K] 77K The difference (S1 - T 77K ) is defined as ΔST.

[1050] Preferably, when the organic EL element 1 of the present embodiment emits light, in the light-emitting layer 5, mainly a fluorescent light-emitting compound emits light.

[1051] Preferably, the organic EL element 1 of the present embodiment emits red light or green light.

[1052] When the organic EL element 1 of the present 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.

[1053] When the organic EL element 1 of the present 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.

[1054] When the organic EL element 1 of the present 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.

[1055] The measurement of the main peak wavelength of the light emitted from the organic EL element 1 is performed as follows.

[1056] Using a spectro-emission luminance meter CS-2000 (manufactured by Konica Minolta), measure the spectro-emission luminance spectrum when a voltage is applied to the organic EL element 1 so that the current density reaches 10 mA / cm 2 .

[1057] In the obtained spectro-emission luminance spectrum, measure the peak wavelength of the emission spectrum with the maximum emission intensity, and take it as the main peak wavelength (unit: nm).

[1058] · Thickness of the light-emitting layer

[1059] In the organic EL element 1 of the present embodiment, the film thickness of the light-emitting layer 5 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, formation of the light-emitting layer and adjustment of chromaticity become easy, and if it is 50 nm or less, an increase in driving voltage is easily suppressed.

[1060] · Content ratio of the compound in the light-emitting layer

[1061] In the organic EL element 1 of the present embodiment, in the light-emitting layer 5, the content ratio of the first compound 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 further preferably 0.01% by mass or more and 1% by mass or less.

[1062] The content ratio 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 further preferably 20% by mass or more and 60% by mass or less.

[1063] The content ratio of the third compound is preferably 10% by mass or more and 80% by mass or less.

[1064] The upper limit of the total content ratio of the first compound, the second compound, and the third compound in the light-emitting layer 5 is 100% by mass. In addition, it is not excluded that materials other than the first compound, the second compound, and the third compound are included in the light-emitting layer 5 of the present embodiment.

[1065] The light-emitting layer 5 may contain only one kind of the first compound, or may contain two or more kinds of the first compound. The light-emitting layer 5 may contain only one kind of the second compound, or may contain two or more kinds of the second compound. The light-emitting layer 5 may contain only one kind of the third compound, or may contain two or more kinds of the third compound.

[1066] According to the first embodiment, a high-performance organic EL element 1 can be realized. The organic EL element 1 of the first embodiment can be used in electronic devices such as a display device and a light-emitting device.

[1067] The configuration of the organic EL element 1 will be further described. Hereinafter, the description of reference numerals may sometimes be omitted.

[1068] (Substrate)

[1069] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a substrate that can be bent (flexible), such as a plastic substrate. As the material for forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. can be cited. In addition, an inorganic vapor deposition film can also be used.

[1070] (Anode)

[1071] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, and their mixture, etc. with a relatively large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium containing tungsten oxide and zinc oxide, graphene, etc. can be cited. In addition to these, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (such as titanium nitride) can also be cited.

[1072] These materials are usually formed into a film by sputtering. For example, for indium zinc oxide, it can be formed by sputtering using a target containing 1 mass% or more and 10 mass% or less of zinc oxide relative to indium oxide. In addition, for example, for indium containing tungsten oxide and zinc oxide, it can be formed by sputtering using a target containing 0.5 mass% or more and 5 mass% or less of tungsten oxide and 0.1 mass% or more and 1 mass% or less of zinc oxide relative to indium oxide. In addition to this, it can also be fabricated by vacuum evaporation, coating, inkjet, spin coating, etc.

[1073] In the EL layer formed on the anode, the hole injection layer formed in contact with the anode is formed of a composite material that easily injects holes (voids) regardless of the work function of the anode. Therefore, materials that can be used as electrode materials (for example, metals, alloys, conductive compounds, and their mixtures, and also include elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1074] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table, such as lithium (Li) and cesium (Cs), which are materials with a small work function, alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing them (such as MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. In addition, when forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using silver paste or the like, a coating method or an inkjet method can be used.

[1075] (Cathode)

[1076] The cathode is preferably made of a metal, an alloy, a conductive compound, or a mixture thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as lithium (Li) and cesium (Cs), which are alkali metals, alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing them (such as MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[1077] In addition, when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste or the like, a coating method or an inkjet method can be used.

[1078] In addition, by providing an electron injection layer, it is possible to form a cathode using various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide, regardless of the work function. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[1079] (Hole injection layer)

[1080] The hole injection layer is a layer containing a substance with high hole injection properties. As a substance with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1081] In addition, as substances with high hole injection properties, aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc., and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) can also be cited as low-molecular organic compounds.

[1082] In addition, high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used as substances with high hole injection properties. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. can be cited. In addition, acid-added high molecular compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[1083] (Hole transport layer)

[1084] The hole transport layer is a layer containing a substance with high hole transport properties. The hole transport layer can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds can be used. The substances mentioned here mainly have a hole mobility of 10 -6 cm 2 / (V·s) or more.

[1085] The hole transport layer can use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[1086] However, as long as the substance has higher hole transport properties than electrons, other substances can also be used. In addition, the layer containing a substance with high hole transport properties can be not only a single layer, but also a layer obtained by laminating two or more layers formed of the above substances.

[1087] When two or more hole transport layers are arranged, it is preferable to arrange a material with a larger band gap on the side closer to the light-emitting layer. As such a material, HT-2 used in the following examples can be cited.

[1088] (Electron transport layer)

[1089] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. Specifically, as low-molecular-weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, a benzimidazole compound can be preferably used. The substances mentioned here mainly have an electron mobility of 10 -6 cm 2 / (V·s) or more. In addition, as long as the substance has higher electron transport properties than hole transport properties, other substances than those described above can also be used as the electron transport layer. In addition, the electron transport layer can be composed of a single layer or can be composed of two or more layers stacked with the above substances.

[1090] In addition, polymer compounds can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.

[1091] (Electron injection layer)

[1092] The electron injection layer is a layer containing a substance with high electron injection property. In the electron injection layer, 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), lithium oxide (LiOx), etc. can be used. In addition, a substance obtained by containing an alkali metal, an alkaline earth metal or their compounds in a substance having electron transport property can also be used, specifically, a substance obtained by containing magnesium (Mg) in Alq, etc. In addition, in this case, electron injection from the cathode can be performed more efficiently.

[1093] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) can also be used in the electron injection layer. Such a composite material generates electrons in the organic compound through the electron donor, and thus has excellent electron injection property and electron transport property. In this case, as the organic compound, a material with excellent electron transport of the generated electrons is preferably used, and specifically, a substance (such as a metal complex or a heteroaromatic compound) constituting the above-mentioned electron transport layer can be used. As the electron donor, any substance that shows electron-donating property to the organic compound can be used. Specifically, alkali metals, alkaline earth metals or rare earth metals are preferably used, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides or alkaline earth metal oxides are preferably used, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[1094] (Layer formation method)

[1095] As the formation method of each layer of the organic EL element of the present embodiment, there is no limitation other than those specifically mentioned above, and known methods such as dry film formation methods such as vacuum evaporation method, sputtering method, plasma method, ion plating method, etc. or wet film formation methods such as spin coating method, dipping method, flow coating method, inkjet method, etc. can be adopted.

[1096] (Film thickness)

[1097] The film thickness of each organic layer of the organic EL element of the present embodiment is not limited other than those specifically mentioned above, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a higher applied voltage is required and the efficiency deteriorates. Therefore, a range of several nm to 1 μm is generally preferred.

[1098] [Second Embodiment]

[1099] [Electronic device]

[1100] The electronic device of the present embodiment is equipped with the organic EL element of the above-described embodiment. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include a display component (such as an organic EL panel module), a television, a mobile phone, a tablet computer, and a personal computer. Examples of the light-emitting device include lighting and vehicle lamps.

[1101] 〔Modifications of the Embodiment〕

[1102] In addition, the present invention is not limited to the above-described embodiment, and changes, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

[1103] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one light-emitting layer satisfies the conditions described in the above embodiment. For example, other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission caused by the direct electron transfer from the triplet excited state to the ground state.

[1104] In addition, when the organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or may be a so-called tandem organic EL element in which multiple light-emitting units are stacked with an intermediate layer therebetween.

[1105] In addition, it is preferable that a blocking layer is disposed adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least any one of holes, electrons, and excitons.

[1106] Specifically, in the present embodiment, on the anode side of the light-emitting layer, as the first layer, an electron blocking layer is disposed adjacent to the light-emitting layer. It can be considered that since the first layer contains a compound represented by the general formula (A), 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.

[1107] In addition, on the cathode side of the light-emitting layer, in the present embodiment, as the second layer, a hole blocking layer is disposed adjacent to the light-emitting layer. It can be considered that since the second layer contains a compound represented by the general formula (B), 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.

[1108] It is preferable that the light-emitting layer is joined to the electron blocking layer. It is preferable that the light-emitting layer is joined to the hole blocking layer.

[1109] In addition, specific structures, shapes, etc. in the implementation of the present invention may adopt other structures, etc. within the scope that can achieve the object of the present invention.

[1110] In this specification, the numerical range represented by "~" means the range that includes the numerical value described before "~" as the lower limit value and the numerical value described after "~" as the upper limit value.

[1111] In this specification, when Rx and Ry are bonded to each other to form a ring, it means that, for example, Rx and Ry contain a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a silicon atom, and the atoms (carbon atom, nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, or silicon atom) contained in Rx are bonded to the atoms (carbon atom, nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, or silicon atom) contained in Ry via a single bond, a double bond, a triple bond, or a divalent linking group to form a ring having 5 or more ring-forming atoms (specifically, for example, a heterocyclic ring or an aromatic hydrocarbon ring). x is a number, a letter, or a combination of a number and a letter. y is a number, a letter, or a combination of a number and a letter.

[1112] There is no particular limitation on the divalent linking group. For example, -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa-, and a group obtained by combining two or more of these linking groups can be exemplified.

[1113] In this specification, unless otherwise specified, as a specific example of the heterocyclic ring, a ring structure (heterocyclic ring) obtained by removing a chemical bond from "heteroaryl Sub2" exemplified in the "description of each substituent in the general formula" described later can be exemplified. These heterocyclic rings may have substituents.

[1114] In this specification, unless otherwise specified, as a specific example of the aromatic hydrocarbon ring, a ring structure (aromatic hydrocarbon ring) obtained by removing a chemical bond from "aryl Sub1" exemplified in the "description of each substituent in the general formula" described later can be exemplified. These aromatic hydrocarbon rings may have substituents.

[1115] As Ra, for example, a substituted or unsubstituted alkyl Sub3 having 1 to 30 carbon atoms, a substituted or unsubstituted aryl Sub1 having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl Sub2 having 5 to 30 ring-forming atoms, etc., exemplified in the "description of each substituent in the general formula" described later can be exemplified.

[1116] For example, the formation of a ring by the bonding of Rx and Ry to each other 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 the general formula (E2); in the molecular structure represented by the general formula (F1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring F represented by the general formula (F2); in the molecular structure represented by the general formula (G1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring G represented by the general formula (G2); in the molecular structure represented by the general formula (H1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring H represented by the general formula (H2); in the molecular structure represented by the general formula (I1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring I represented by the general formula (I2).

[1117] In the general formulas (E1) to (I1), * each independently represents the position of bonding to other atoms in one molecule. The two * in the general formula (E1) respectively correspond to the two * in the general formula (E2), the two * in the general formula (F1) respectively correspond to the two * in the general formula (F2), the two * in the general formula (G1) respectively correspond to the two * in the general formula (G2), the two * in the general formula (H1) respectively correspond to the two * in the general formula (H2), and the two * in the general formula (I1) respectively correspond to the two * in the general formula (I2).

[1118] [Chemical formula 132]

[1119]

[1120] [Chemical formula 133]

[1121]

[1122] In the molecular structures represented by the general formulas (E2) to (I2), E to I respectively represent ring structures (rings having 5 or more ring-forming atoms). In the general formulas (E2) to (I2), * each independently represents the position of bonding to other atoms in one molecule. The two * in the general formula (E2) respectively correspond to the two * in the general formula (E1). The two * in the general formulas (F2) to (I2) also respectively correspond to the two * in the general formulas (F1) to (I1).

[1123] For example, in the general formula (E1), when Rx1 and Ry1 bond to each other to form the ring E in the general formula (E2) and the ring E is an unsubstituted benzene ring, the molecular structure represented by the general formula (E1) becomes the molecular structure represented by the following general formula (E3). Here, the two * in the general formula (E3) respectively independently correspond to the two * in the general formula (E2) and the general formula (E1).

[1124] For example, in general formula (E1), when Rx1 and Ry1 are bonded to each other 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 general formula (E4) below. Here, the two * in general formula (E4) respectively and independently correspond to the two * in general formula (E2) and general formula (E1). In general formulas (E3) and (E4), * respectively and independently represents the position of bonding to other atoms in one molecule.

[1125] [Chemical Formula 134]

[1126]

[1127] In this specification, the number of ring-forming carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (for example, monocyclic compound, polycyclic compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below, unless otherwise specified. For example, the number of ring-forming carbon atoms of a benzene ring is 6, the number of ring-forming carbon atoms of a naphthalene ring is 10, the number of ring-forming carbon atoms of a pyridyl group is 5, and the number of ring-forming carbon atoms of a furyl group is 4. In addition, when, for example, an alkyl group is substituted as a substituent on a benzene ring or a naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms. In addition, when, for example, a fluorene ring (including a spirofluorene ring) is bonded as a substituent to a fluorene ring, the number of carbon atoms of the fluorene ring as the substituent is not included in the number of ring-forming carbon atoms.

[1128] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (for example, monocyclic, polycyclic, fused ring) (for example, monocyclic compound, polycyclic compound, crosslinked compound, carbocyclic compound, heterocyclic compound). Atoms that do not form a ring and atoms contained in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below, unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. Hydrogen atoms bonded to the carbon atoms of the pyridine ring or the quinazoline ring and atoms constituting the substituent are not included in the number of ring-forming atoms. In addition, when, for example, a fluorene ring (including a spirofluorene ring) is bonded as a substituent to a fluorene ring, the number of atoms of the fluorene ring as the substituent is not included in the number of ring-forming atoms.

[1129] · Explanation of each substituent in the general formula in this specification (Explanation of each substituent)

[1130] The aryl group (sometimes referred to as an aromatic hydrocarbon group) in the present specification is, for example, aryl Sub1, which is at least any one group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, pyrenyl, -yl, fluoranthenyl, benz[a]anthracenyl, benz[c]phenanthryl, triphenylene, benz[k]fluoranthenyl, benz[g] -yl, benz[b]triphenylene, picenyl, and perylenyl.

[1131] As aryl Sub1 in the present specification, the number of ring carbon atoms is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 14, and even more preferably 6 to 12. Among the above 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 the 9-position is preferably substituted or unsubstituted alkyl Sub3 or substituted or unsubstituted aryl Sub1 described in the present specification hereinafter.

[1132] The heteroaryl group (sometimes referred to as a heterocyclic group, heteroaromatic ring group, or aromatic heterocyclic group) in the present specification is, for example, heterocyclic group Sub2. Heterocyclic group Sub2 is a group containing at least any one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium, and germanium atoms as a heteroatom. Heterocyclic group Sub2 is preferably a group containing at least any one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom.

[1133] The heterocyclic group Sub2 in the present specification is, for example, at least any one group selected from the group consisting of pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuryl, benzothienyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzofuryl, dibenzothienyl, piperidinyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, and phenoxazinyl.

[1134] As the heterocyclic group Sub2 in this specification, the number of ring-forming atoms is preferably 5 to 30, more preferably 5 to 20, and still more preferably 5 to 14. Among the above-mentioned heterocyclic groups Sub2, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, and 9-carbazolyl are still more preferred. For 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, and 4-carbazolyl, it is preferred that the nitrogen atom at the 9-position is substituted by the substituted or unsubstituted aryl group Sub1 or the substituted or unsubstituted heterocyclic group Sub2 in this specification.

[1135] In addition, in this specification, the heterocyclic group Sub2 may also be, for example, a group derived from the partial structure represented by the following general formulas (XY-1) to (XY-18).

[1136] [Chemical formula 135]

[1137]

[1138] [Chemical formula 136]

[1139]

[1140] [Chemical formula 137]

[1141]

[1142] In the general formulas (XY-1) to (XY-18), X A and Y A are each independently a heteroatom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. The partial structure represented by the general formulas (XY-1) to (XY-18) forms a heterocyclic group with a chemical bond at any position, and the heterocyclic group may have a substituent.

[1143] In addition, in this specification, the heterocyclic group Sub2 may also be, for example, a group represented by the following general formulas (XY-19) to (XY-22). In addition, the position of the chemical bond may also be appropriately changed.

[1144] [Chemical formula 138]

[1145]

[1146] The alkyl group in this specification may be any of a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group.

[1147] The alkyl group in this specification is, for example, alkyl group Sub3.

[1148] The linear alkyl group in this specification is, for example, linear alkyl Sub 31 .

[1149] The branched alkyl group in this specification is, for example, branched alkyl Sub 32 .

[1150] The cyclic alkyl group in this specification is, for example, cyclic alkyl Sub 33 .

[1151] Alkyl Sub3 is, for example, at least any one group selected from the group consisting of linear alkyl Sub 31 , branched alkyl Sub 32 , and cyclic alkyl Sub 33 .

[1152] Linear alkyl Sub 31 or branched alkyl Sub 32 is, for example, at least any 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-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl.

[1153] The linear alkyl Sub 31 or branched alkyl Sub 32 in this specification preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms. As the above linear alkyl Sub 31 or branched alkyl Sub 32 , it is still more preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, pentyl, isopentyl, and neopentyl.

[1154] The cyclic alkyl Sub 33 in this specification is, for example, cycloalkyl Sub 331 .

[1155] The cycloalkyl Sub 331 in this specification is, for example, at least any one group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, and norbornyl. The number of carbon atoms forming the ring of cycloalkyl Sub 331 preferably is 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and still more preferably 5 to 8. In cycloalkyl Sub 331Among them, a cyclopentyl group or a cyclohexyl group is more preferably used.

[1156] The haloalkyl group in this specification is, for example, haloalkyl Sub4, and haloalkyl Sub4 is an alkyl group obtained by substituting one or more halogen atoms, preferably fluorine atoms, for alkyl Sub3.

[1157] The haloalkyl Sub4 in this specification is, for example, at least any one group selected from the group consisting of fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethylmethyl, trifluoroethyl, and pentafluoroethyl.

[1158] The substituted silyl group in this specification is, for example, substituted silyl Sub5, and substituted silyl Sub5 is, for example, at least any one group selected from the group consisting of alkylsilyl Sub 51 and arylsilyl Sub 52 constituting the group.

[1159] The alkylsilyl Sub 51 in this specification is, for example, a trialkylsilyl Sub 511 having the above alkyl Sub3.

[1160] The trialkylsilyl Sub 511 is, for example, at least any 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-t-butylsilyl, diethylisopropylsilyl, vinyldimethylsilyl, propyldimethylsilyl, and triisopropylsilyl. The three alkyl Sub3 in the trialkylsilyl Sub 511 can be the same as or different from each other.

[1161] The arylsilyl Sub 52 in this specification is, for example, at least any one group selected from the group consisting of dialkylarylsilyl Sub 521 , alkyldiarylsilyl Sub 522 and triarylsilyl Sub 523 constituting the group.

[1162] The dialkylarylsilyl Sub 521 is, for example, a dialkylarylsilyl having two of the above alkyl Sub3 and one of the above aryl Sub1. The carbon number of the dialkylarylsilyl Sub 521 is preferably 8 to 30.

[1163] The alkyldiarylsilyl Sub 522For example, it is an alkyldiarylsilyl group having 1 of the above alkyl Sub3 and 2 of the above aryl Sub1. The alkyldiarylsilyl Sub 522 preferably has 13 to 30 carbon atoms.

[1164] Triarylsilyl Sub 523 For example, it is a triarylsilyl group having 3 of the above aryl Sub1. The triarylsilyl Sub 523 preferably has 18 to 30 carbon atoms.

[1165] The substituted or unsubstituted alkylsulfonyl group in this specification is, for example, alkylsulfonyl Sub6, and alkylsulfonyl Sub6 is represented by -SO2R w . -SO2R w The R in w represents the above substituted or unsubstituted alkyl Sub3.

[1166] The aralkyl group (sometimes referred to as arylalkyl) in this specification is, for example, aralkyl Sub7. The aryl in aralkyl Sub7 includes, for example, at least one of the above aryl Sub1 and the above heteroaryl Sub2.

[1167] The aralkyl Sub7 in this specification is preferably a group having aryl Sub1 and is represented as -Z3-Z4. This Z3 is, for example, an alkylene group corresponding to the above alkyl Sub3, etc. This Z4 is, for example, the above aryl Sub1. In this aralkyl Sub7, preferably, the aryl part has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl part has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, further preferably 1 to 6). The aralkyl Sub7 is, for example, at least any one group selected from the group consisting of benzyl, 2-phenylpropan-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.

[1168] The alkoxy group in this specification is, for example, alkoxy Sub8, and alkoxy Sub8 is represented by -OZ1. This Z1 is, for example, the above alkyl Sub3. The alkoxy Sub8 is, for example, at least any one group selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy. The alkoxy Sub8 preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms.

[1169] The haloalkoxy group in this specification is, for example, haloalkoxy Sub9, and haloalkoxy Sub9 is, for example, an alkoxy group obtained by substituting one or more halogen atoms, preferably fluorine atoms, for the above-mentioned alkoxy Sub8.

[1170] The aryloxy group (sometimes referred to as arylalkoxy group) in this specification is, for example, arylalkoxy Sub 10 . The aryl in arylalkoxy Sub 10 includes at least one of aryl Sub1 and heteroaryl Sub2.

[1171] The arylalkoxy Sub 10 is represented as -OZ2. This Z2 is, for example, aryl Sub1 or heteroaryl Sub2. The ring-forming carbon number of arylalkoxy Sub 10 is preferably 6 to 30, more preferably 6 to 20. As this arylalkoxy Sub 10 , phenoxy group can be cited as an example.

[1172] The substituted amino group in this specification is, for example, substituted amino Sub 11 , and substituted amino Sub 11 is, for example, at least any one group selected from the group consisting of arylamino Sub 111 and alkylamino Sub 112 .

[1173] Arylamino Sub 111 is represented as -NHR V1 or -N(R V1 )2. This R V1 is, for example, aryl Sub1. The two Rs in -N(R V1 )2 V1 are the same or different.

[1174] Alkylamino Sub 112 is represented as -NHR V2 or -N(R V2 )2. This R V2 is, for example, alkyl Sub3. The two Rs in -N(R V2 )2 V2 are the same or different.

[1175] The alkenyl group in this specification is, for example, alkenyl Sub 12 , and alkenyl Sub 12 is either straight-chain or branched-chain, and is, for example, at least any one group selected from the group consisting of vinyl, propenyl, butenyl, oleyl, eicosapentaenyl, docosahexaenyl, styryl, 2,2-diphenylethylene, 1,2,2-triphenylethylene, and 2-phenyl-2-propenyl.

[1176] The alkynyl group in this specification is, for example, alkynyl Sub 13 , alkynyl Sub 13 can be either linear or branched, and is, for example, at least any one group selected from the group consisting of ethynyl, propynyl, and 2-phenylethynyl.

[1177] The alkylthio group in this specification is, for example, alkylthio Sub 14 .

[1178] Alkylthio Sub 14 is represented as -SR V3 . This R V3 is, for example, alkyl Sub3. The carbon number of alkylthio Sub 14 is preferably 1 to 30, more preferably 1 to 20.

[1179] The arylthio group in this specification is, for example, arylthio Sub 15 .

[1180] Arylthio Sub 15 is represented as -SR V4 . This R V4 is, for example, aryl Sub1. The ring-forming carbon number of arylthio Sub 15 is preferably 6 to 30, more preferably 6 to 20.

[1181] Examples of the halogen atom in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, etc., and a fluorine atom is preferred.

[1182] The substituted phosphino group in this specification is, for example, substituted phosphino Sub 16 , substituted phosphino Sub 16 is, for example, phenylphosphino.

[1183] The arylcarbonyl group in this specification is, for example, arylcarbonyl Sub 17 , arylcarbonyl Sub 17 is represented as -COY’. This Y’ is, for example, aryl Sub1. The arylcarbonyl Sub in this specification 17 is, for example, at least any one group selected from the group consisting of phenylcarbonyl, diphenylcarbonyl, naphthylcarbonyl, and triphenylcarbonyl.

[1184] The acyl group in this specification is, for example, acyl Sub 18 , acyl Sub 18 is represented as -COR’. This R’ is, for example, alkyl Sub3. The acyl Sub in this specification 18 is, for example, at least any one group selected from the group consisting of acetyl and propionyl.

[1185] The substituted phosphoryl groups in this specification are, for example, substituted phosphoryl groups such as arylphosphoryl groups and alkylphosphoryl groups Sub 19 , the substituted phosphoryl group Sub 19 is represented by the following general formula (P).

[1186] [Chemical formula 139]

[1187]

[1188] In the general formula (P), Ar P1 and Ar P2 are each any substituent selected from the group consisting of the above alkyl Sub3 and the above aryl Sub1.

[1189] The ester groups in this specification are, for example, ester group Sub 20 , the ester group Sub 20 is, for example, at least any one group selected from the group consisting of alkyl ester groups and aryl ester groups.

[1190] The alkyl ester groups in this specification are, for example, alkyl ester group Sub 201 , the alkyl ester group Sub 201 is represented as -C(=O)OR E . R E is, for example, the above substituted or unsubstituted alkyl Sub3.

[1191] The aryl ester groups in this specification are, for example, aryl ester group Sub 202 , the aryl ester group Sub 202 is represented as -C(=O)OR Ar . R Ar is, for example, the above substituted or unsubstituted aryl Sub1.

[1192] The siloxanyl groups in this specification are, for example, siloxanyl group Sub 21 , the siloxanyl group Sub 21 is a silicon compound group obtained via an ether bond. The siloxanyl group Sub 21 is, for example, trimethylsiloxanyl.

[1193] The carbamoyl group in this specification is represented as -CONH2.

[1194] The substituted carbamoyl groups in this specification are, for example, carbamoyl group Sub 22 , the carbamoyl group Sub 22 is represented as -CONH-Ar C or -CONH-R C . Ar CFor example, it is at least any one group selected from the group consisting of the above-mentioned substituted or unsubstituted aryl Sub1 (preferably having 6 to 10 ring carbon atoms) and the above-mentioned heteroaryl Sub2 (preferably having 5 to 14 ring atoms). Ar C It may be a group obtained by bonding aryl Sub1 and heteroaryl Sub2.

[1195] R C For example, it is the above-mentioned substituted or unsubstituted alkyl Sub3 (preferably having 1 to 6 carbon atoms).

[1196] In this specification, "ring carbon" refers to a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. "Ring atom" refers to a carbon atom and a heteroatom constituting a heterocycle (including a saturated ring, an unsaturated ring, and an aromatic ring).

[1197] In addition, in this specification, a hydrogen atom includes isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[1198] Hereinafter, alkyl Sub3 refers to a straight-chain alkyl Sub described in "Description of Each Substituent" 31 , a branched-chain alkyl Sub 32 and a cyclic alkyl Sub 33 any one or more groups among them.

[1199] Similarly, substituted silyl Sub5 refers to any one or more groups among alkylsilyl Sub 51 and arylsilyl Sub 52 among them.

[1200] Similarly, substituted amino Sub 11 refers to any one or more groups among arylamino Sub 111 and alkylamino Sub 112 among them.

[1201] In this specification, as a substituent in the case of "substituted or unsubstituted", for example, it is substituent R F1 , substituent R F1 is selected 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 Sub 11 , alkenyl Sub 12 , alkynyl Sub 13 , alkylthio Sub 14 , arylthio Sub 15 , substituted phosphino Sub16 , arylcarbonyl Sub 17 , acyl Sub 18 , substituted phosphoryl Sub 19 , ester group Sub 20 , siloxanyl 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.

[1202] In this specification, in the case of "substituted or unsubstituted", the substituent R F1 may also be diarylboron group (Ar B1 Ar B2 B-). As examples of this Ar B1 and Ar B2 , the above-mentioned aryl Sub1 can be cited. Ar B1 Ar B2 In Ar B1 Ar B2 B-, Ar

[1203] As specific examples and preferred groups of the substituent R F1 , those similar to the specific examples and preferred groups of the substituents (for example, aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, aryloxyalkyl Sub 10 , substituted amino Sub 11 , alkenyl Sub 12 , alkynyl Sub 13 , alkylthio Sub 14 , arylthio Sub 15 , substituted phosphino Sub 16 , arylcarbonyl Sub 17 , acyl Sub 18 , substituted phosphoryl Sub 19 , ester group Sub 20 , siloxanyl Sub 21 and carbamoyl Sub 22 ) can be cited.

[1204] In the case of "substituted or unsubstituted", the substituent R F1It can be selected from the group consisting of aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 , substituted amino Sub 11 , alkenyl Sub 12 , alkynyl Sub 13 , alkylthio Sub 14 , arylthio Sub 15 , substituted phosphino Sub 16 , arylcarbonyl Sub 17 , acyl Sub 18 , substituted phosphoryl Sub 19 , ester group Sub 20 , siloxanyl Sub 21 , carbamoyl Sub 22 , at least one group selected from the group consisting of unsubstituted amino, unsubstituted silyl, halogen atom, cyano group, hydroxyl group, nitro group, and carboxyl group (hereinafter also referred to as substituent R F2 ). Further substituted. In addition, these multiple substituents R F2 can also bond to each other to form a ring.

[1205] In the case of "substituted or unsubstituted", "unsubstituted" means not being substituted by the substituent R F1 and having a hydrogen atom bonded thereto.

[1206] In addition, in this specification, in the expression of "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "having XX to YY carbon atoms" means the number of carbon atoms of the ZZ group in the case of being unsubstituted, excluding the carbon atoms of the substituent R F1 in the case of substitution.

[1207] In this specification, in the expression of "substituted or unsubstituted ZZ group having XX to YY atoms", "having XX to YY atoms" means the number of atoms of the ZZ group in the case of being unsubstituted, excluding the atoms of the substituent R F1 in the case of substitution.

[1208] In the compounds or their partial structures described in this specification, for the case of "substituted or unsubstituted", it is the same as described above.

[1209] 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.

[1210] In this specification, as the aromatic hydrocarbon group in the linking group, for example, a divalent or higher-valent group obtained by removing one or more atoms from the above-mentioned monovalent aryl group Sub1 can be exemplified.

[1211] In this specification, as the heterocyclic group in the linking group, for example, a divalent or higher-valent group obtained by removing one or more atoms from the above-mentioned monovalent heteroaryl group Sub2 can be exemplified.

[1212] [Examples]

[1213] Hereinafter, examples of the present invention will be described. The present invention is not limited by any of these examples.

[1214] [Compound]

[1215] Compounds represented by the general formula (A) and compounds represented by the general formula (B) for manufacturing the organic EL element used in the examples are as follows.

[1216] [Chemical formula 140]

[1217]

[1218] Compounds represented by the general formula (1) and compounds represented by the general formula (2) for manufacturing the organic EL element used in Example 1 are as follows.

[1219] [Chemical formula 141]

[1220]

[1221] Compounds represented by the general formula (3) for manufacturing the organic EL element used in the examples are as follows.

[1222] [Chemical formula 142]

[1223]

[1224] The structures of other compounds for manufacturing the organic EL element used in the examples are as follows.

[1225] [Chemical formula 143]

[1226]

[1227] [Chemical formula 144]

[1228]

[1229] [Fabrication of Organic EL Element]

[1230] An organic EL element was fabricated and evaluated as described below.

[1231] [Example 1]

[1232] [Manufacture of Bottom Emission Type Organic EL Element]

[1233] A glass substrate (manufactured by GioMa Technology Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 1 minute. The film thickness of ITO was set to 130 nm.

[1234] The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus, and compounds HT and HA were co-evaporated in such a manner as to cover the transparent electrode on the surface on the side where the transparent electrode lines were formed, thereby forming a hole injection layer with a film 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.

[1235] Next, compound HT was evaporated on the hole injection layer to form a hole transport layer with a film thickness of 200 nm.

[1236] Next, compound EBL-1 was evaporated on the hole transport layer to form an electron blocking layer with a film thickness of 10 nm as the first layer.

[1237] Next, a fluorescent light-emitting compound RD-1 as the first compound, a thermally activated delayed fluorescence compound TADF-1 as the second compound, and a compound D-1 as the third compound were co-evaporated on the electron blocking layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of compound RD-1 in the light-emitting layer was set to 1% by mass, the concentration of compound TADF-1 was set to 25% by mass, and the concentration of compound D-1 was set to 74% by mass.

[1238] Next, compound HBL-1 was evaporated on the light-emitting layer to form a hole blocking layer with a film thickness of 10 nm as the second layer.

[1239] Next, compound ET was evaporated on the hole blocking layer to form an electron transport layer with a film thickness of 30 nm.

[1240] Next, lithium fluoride (LiF) was evaporated on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1241] Then, metallic aluminum (Al) was evaporated on the electron injection electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1242] If the element configuration of the organic EL element of Example 1 is schematically shown, it is as follows.

[1243] ITO(130) / HT:HA(10, 97%:3%) / HT(200) / EBL-1(10) / D-1:TADF-1:RD-1(25, 74%:25%:1%) / HBL-1(10) / ET(30) / LiF(1) / Al(80)

[1244] In addition, the numbers in parentheses represent the film thickness (unit: nm).

[1245] Within the same parentheses, the numbers represented by the percentages (97%:3%) show the ratio (mass%) of compound HT and compound HA in the hole injection layer, and the numbers represented by the percentages (74%:25%:1%) show the ratio (mass%) of the third compound, the second compound, and the first compound in the light-emitting layer. The following markings are made in the same way.

[1246] The structures of the electron blocking layer, the light-emitting layer, and the hole blocking layer of the organic EL element fabricated in Example 1 are shown in Table 1.

[1247] [Table 1]

[1248]

[1249] <Evaluation>

[1250] The organic EL element fabricated in Example 1 was driven. As a result, the organic EL element of Example 1 emitted red light.

[1251] <Evaluation of Compounds>

[1252] The physical property values of the compounds described in Table 1 and Table 2 were measured by the following method.

[1253] <Ionization Potential Ip>

[1254] The ionization potential Ip of compound EBL-1 was measured by the following method.

[1255] The ionization potential Ip was measured using a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd., "AC-3") under atmospheric conditions. Specifically, the material to be measured was irradiated with light, and the amount of electrons generated due to charge separation at this time was measured, thereby measuring the ionization potential Ip.

[1256] · Delayed Fluorescence Property of Compound TADF-1

[1257] The delayed fluorescence property was measured by using Figure 2The device shown measures the transient PL for confirmation. The compound TADF-1 is dissolved in toluene. To eliminate the influence of self-absorption, a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared. In addition, to prevent quenching caused by oxygen, the sample solution is frozen, degassed, and then sealed in a capped cell under an argon atmosphere, thereby producing an oxygen-free sample solution saturated with argon.

[1258] The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation). In addition, the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. Using the fluorescence area intensity 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.

[1259] After excitation with pulsed light (light irradiated from a pulsed laser) at a wavelength absorbed by the compound TADF-1, there is Prompt luminescence (instantaneous luminescence) that can be observed immediately from this excited state and Delay luminescence (delayed luminescence) that cannot be observed immediately after this excitation but is observed later. The delayed fluorescence luminescence in this example refers to the amount of Delay luminescence (delayed luminescence) being 5% or more relative to the amount of Prompt luminescence (instantaneous luminescence). Specifically, it means that when the amount of Prompt luminescence (instantaneous luminescence) is denoted as X P and the amount of Delay luminescence (delayed luminescence) is denoted as X D , X D / X P has a value of 0.05 or more.

[1260] The amounts of Prompt luminescence and Delay luminescence and their ratio can be obtained by the same method as the method described in "Nature" 492, 234 - 238, 2012 (Reference 1). In addition, the device used to calculate the amounts of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or Figure 2 the device described therein.

[1261] For the compound TADF-1, it was confirmed that the amount of Delay luminescence (delayed luminescence) is 5% or more relative to the amount of Prompt luminescence (instantaneous luminescence).

[1262] Specifically, for the compound TADF-1, X D / X P has a value of 0.05 or more.

[1263] · Singlet energy S1

[1264] The singlet energy S1 of compound RD-1, compound TADF-1, and compound D-1 was measured by the solution method described above.

[1265] · Energy gap T at 77 [K] 77K

[1266] Measure the energy gap T of compound TADF-1 at 77 [K]. 77K , and confirm △ST based on this result and the value of the singlet energy S1 described above. Use the energy gap T described in the "Relationship between triplet energy and energy gap at 77 [K]" above 77K to measure the energy gap T of compound TADF-1. 77K .

[1267] · Main peak wavelength λ of the compound

[1268] The main peak wavelength λ of compound RD-1 was measured by the following method.

[1269] Prepare a 5 μmol / L toluene solution of the compound to be measured and add it to a quartz cell, and measure the emission spectrum of this sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). In this example, the emission spectrum was measured using a spectrophotometer manufactured by Hitachi, Ltd. (device name: F-7000). In addition, the emission spectrum measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is used as the main peak wavelength λ.

[1270] [Table 2]

[1271]

[1272] · Explanation of Table 2

[1273] "-" indicates not measured.

[1274] "<0.01" indicates that △ST is less than 0.01 eV.

[1275] [Example 2]

[1276] [Manufacture of bottom-emitting organic EL element]

[1277] An organic EL element of Example 2 was fabricated in the same manner as in Example 1, except that compound RD-1 in the light-emitting layer was changed to the following compound RD-2.

[1278] [Chemical formula 145]

[1279]

[1280] If the element configuration of the organic EL element of Example 2 is shown schematically, it is as follows.

[1281] ITO(130) / HT: HA(10, 97%: 3%) / HT(200) / EBL-1(10) / D-1: TADF-1: RD-2(25, 74%: 25%: 1%) / HBL-1(10) / ET(30) / LiF(1) / Al(80)

[1282] [Example 3]

[1283] [Manufacture of Bottom-Emitting Organic EL Element]

[1284] An organic EL element of Example 3 was fabricated in the same manner as in Example 1, except that the compound RD-1 in the light-emitting layer was changed to the following compound RD-3.

[1285] [Chemical Formula 146]

[1286]

[1287] If the element structure of the organic EL element of Example 3 is schematically shown, it is as follows.

[1288] ITO(130) / HT: HA(10, 97%: 3%) / HT(200) / EBL-1(10) / D-1: TADF-1: RD-3(25, 74%: 25%: 1%) / HBL-1(10) / ET(30) / LiF(1) / Al(80)

[1289] [Evaluation of Organic EL Element]

[1290] The following evaluations were performed on the organic EL elements of Examples 2 and 3. The measurement results are shown in Table 3.

[1291] · Driving Voltage

[1292] The voltage (unit: V) was measured when an electric current was passed between the anode and the cathode to achieve a current density of 10 mA / cm 2 .

[1293] · External Quantum Efficiency EQE

[1294] The spectral emission luminance spectrum was measured using a spectro-emission luminance meter CS-2000 (manufactured by Konica Minolta Inc.) when a voltage was applied to the element to achieve a current density of 10 mA / cm 2 . Based on the obtained spectral emission luminance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming Lambertian emission.

[1295] · Peak Wavelength λp and Full Width at Half Maximum FWHM during Element Driving

[1296] Using a spectro-emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.), measure the spectro-emission luminance spectrum when a voltage is applied to the element to make the current density of the organic EL element reach 10 mA / cm 2 . From the obtained spectro-emission luminance spectrum, determine the peak wavelength λp (unit: nm) and the full width at half maximum of luminescence FWHM (unit: nm).

[1297] · CIE1931 chromaticity

[1298] Using a spectro-emission luminance meter CS-1000 (manufactured by Konica Minolta Co., Ltd.), measure the CIE1931 chromaticity coordinates (x, y) when a voltage is applied to the element to make the current density reach 10 mA / cm 2 .

[1299] · Lifetime LT95

[1300] Apply a voltage to the obtained organic EL element to make the current density reach 50 mA / cm 2 , and thereby measure the time until the luminance reaches 95% of the initial luminance (LT95 (unit: time)).

[1301] [Table 3]

[1302]

[1303] [Example 4]

[1304] [Manufacture of a top-emission type organic EL element]

[1305] On a glass substrate, sequentially form an APC (Ag-Pd-Cu) layer (reflective layer) (film thickness: 100 nm) made of a silver alloy and an indium zinc oxide (IZO) layer (film thickness: 10 nm) by sputtering.

[1306] Next, using a conventional photolithography technique, pattern the conductive material layer by etching using a resist pattern as a mask to form an anode. After subjecting the substrate with the lower electrode formed thereon to ultrasonic cleaning in isopropyl alcohol for 5 minutes, perform UV ozone cleaning for 30 minutes.

[1307] Thereafter, co-evaporate compounds HT and HA by vacuum evaporation to form a hole injection layer with a film thickness of 10 nm. Set the concentration of compound HT in the hole injection layer to 97 mass% and the concentration of HA to 3 mass%.

[1308] Next, evaporate compound HT on the hole injection layer to form a hole transport layer (HT) with a film thickness of 180 nm.

[1309] Next, compound EBL-1 was vapor-deposited on the hole transport layer to form an electron blocking layer with a film thickness of 10 nm as the first layer.

[1310] Next, a co-evaporation of a fluorescent light-emitting compound RD-2 as the first compound, a thermally activated delayed fluorescence (TADF) compound TADF-1 as the second compound, and a compound D-1 as the third compound was performed on the electron blocking layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of compound RD-2 in the light-emitting layer was set to 1% by mass, the concentration of compound TADF-1 was set to 25% by mass, and the concentration of compound D-1 was set to 74% by mass.

[1311] Next, compound HBL-1 was vapor-deposited on the light-emitting layer to form a hole blocking layer with a film thickness of 15 nm as the second layer.

[1312] Next, compound ET was vapor-deposited on the hole blocking layer to form an electron transport layer with a film thickness of 45 nm.

[1313] Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron-injecting electrode (cathode) with a film thickness of 1 nm.

[1314] Then, on the electron-injecting electrode, Mg and Ag were vapor-deposited at a film thickness ratio of 15:85 to form a cathode composed of a semi-transmissive MgAg alloy with a film thickness of 15 nm. Cap was formed on the cathode by vacuum vapor deposition to form a cover layer with a film thickness of 65 nm.

[1315] If the element structure of the organic EL element of Example 4 is schematically shown, it is as follows.

[1316] APC(100) / IZO(10) / HT:HA(10, 97%:3%) / HT(180) / EBL-1(10) / D-1:TADF-1:RD-2(25, 74%:25%:1%) / HBL-1(15) / ET(45) / LiF(1) / MgAg(15) / Cap(65)

[1317] 〔Examples 5 to 8〕

[1318] [Manufacture of top-emission organic EL element]

[1319] Organic EL elements of Examples 5 to 8 were fabricated in the same manner as in Example 4, except that the film thickness of the hole transport layer (HT) was changed to the film thickness shown in Table 4 and compound RD-2 in the light-emitting layer was changed to compound RD-3.

[1320] <Evaluation of organic EL element>

[1321] The driving voltage, the main peak wavelength λp and the emission half width FWHM when the element is driven, the CIE1931 chromaticity and the life LT95 of the organic EL elements of Examples 5 to 8 were evaluated in the same manner as in Examples 2 and 3. In addition, the luminance-current efficiency (L / J) was measured by the following method.

[1322] Brightness-current efficiency (L / J)

[1323] A voltage was applied to the organic EL device so that the current density reached 10 mA / cm 2 The brightness L (unit: cd / m 2 ).

[1324] The luminance-current efficiency (unit: cd / A) was calculated with respect to the obtained luminance.

[1325] The measurement results are shown in Table 4.

[1326] [Table 4]

[1327]

[1328] [Synthesis Example 1: Synthesis of Compound D-1]

[1329] (1-1) Synthesis of Compound D-1

[1330] The synthesis scheme of compound D-1 is shown below.

[1331] [Chemistry 147]

[1332]

[1333] Under nitrogen atmosphere, xylene (675 mL) was added to a mixture of 12H-benzofuran[2,3-a]carbazole (26.6 g, 103 mmol), 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole (41.2 g, 103 mmol), tri(dibenzylideneacetone)dipalladium (1.90 g, 2.07 mmol), tri-tert-butylphosphine tetrafluoroborate (1.20 g, 4.14 mmol) and sodium tert-butoxide (11.9 g, 124 mmol), and stirred at 130°C for 8 hours. After the reaction was completed, the solid was filtered out. The filtered solid was recrystallized using toluene to obtain compound D-1 (51.5 g, yield 87%). It was identified as compound D-1 by LC-MS (Liquid chromatography massspectrometry) analysis.

[1334] [Synthesis Example 2: Synthesis of Compound TADF-1]

[1335] (2-1) Synthesis of Intermediate A1 and Intermediate A2

[1336] [Chemical Formula 148]

[1337]

[1338] Under a nitrogen atmosphere, in a 2000 mL three-necked flask, add tetrafluoroterephthalonitrile (25 g, 125 mmol), 625 mL of 1,4-dioxane, and 400 mL of water.

[1339] Then add 13 mL of 30 mass% ammonia water, heat and stir at 80 °C for 10 hours, and then return to room temperature (25 °C). Use an evaporator to distill off the solvent, and purify the obtained solid by silica gel column chromatography. 24 g of a white solid was obtained. It was identified as Intermediate A1 by GS-MS (Gas Chromatograph Mass Spectrometry) (yield 98%).

[1340] Under a nitrogen atmosphere, in a 2000 mL three-necked flask, add Intermediate A1 (24 g, 122 mmol), p-toluenesulfonic acid (p-TsOH) (25 g, 146 mmol), benzyltrimethylammonium chloride (BTAC) (45.3 g, 244 mmol), copper(II) chloride (0.16 g, 1.22 mmol), and 400 mL of acetonitrile. Then add tert-butyl nitrite (t-BuONO) (15 g, 146 mmol), and stir at 25 °C for 6 hours. Use an evaporator to distill off the solvent, and purify the obtained solid by silica gel column chromatography. 17 g of a white solid was obtained. It was identified as Intermediate A2 by GC-MS (yield 65%).

[1341] (2-2) Synthesis of Intermediate A3

[1342] [Chemical Formula 149]

[1343]

[1344] Under nitrogen atmosphere, in a 1000mL three-necked flask, intermediate A2 (10g, 46mmol), carbazole (23g, 138mmol), potassium carbonate (19g, 138mmol) and 450mL of DMF were added and stirred at 0°C for 24 hours. 300mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 26g of yellow solid. It was identified as intermediate A3 (yield 85%) by ASAP-MS (Atmospheric Pressure Solid Analysis Probe Mass Spectrometry).

[1345] (2-3) Synthesis of Intermediate C2 and Intermediate D2

[1346] [Chemistry 150]

[1347]

[1348] Under nitrogen atmosphere, 4-bromodibenzothiophene (26.0 g, 100 mmol), 2-chloro-4-methylaniline (17 g, 120 mmol), tri(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.9 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (P(t-Bu)3HBF4) (2.3 g, 8 mmol), sodium tert-butoxide (NaOtBu) (11.5 g, 120 mmol) and 350 mL of toluene were added to a 1 L three-necked flask, and heated and stirred at 60° C. for 7 hours and then cooled to room temperature (25° C.). The reaction solution was purified by silica gel column chromatography to obtain 26 g of a white solid. It was identified as intermediate C2 (yield 80%) by GC-MS analysis.

[1349] Under nitrogen atmosphere, in a 1L three-necked flask, intermediate C2 (26.0g, 80mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (1.4g, 3.2mmol), palladium(II) acetate (Pd(OAc)2) (0.36g, 1.6mmol), potassium carbonate (22.0g, 160mmol) and 400mL of N,N-dimethylacetamide (DMAc) were added, and stirred at 130°C for 7 hours and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 21g of a white solid. It was identified as intermediate D2 (yield 91%) by GC-MS analysis.

[1350] (2-4) Synthesis of Compound TADF-1

[1351] [Chemistry 151]

[1352]

[1353] Under a nitrogen atmosphere, in a 100 mL three-necked flask, intermediate A3 (2 g, 3.0 mmol), intermediate D2 (1.0 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol), and 30 mL of DMF were added, and the mixture was stirred at 70 °C for 8 hours. 50 ml of saturated ammonium chloride aqueous solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.8 g of a red solid. By ASAP-MS analysis, it was identified as TADF-1 (yield 66%).

[1354] [Synthesis Example 3: Synthesis of Compound RD-2]

[1355] 2.5 g of pyrrole compound (2-1) and 0.73 g of 4-methoxy-2,3,6-trimethylbenzaldehyde were dissolved in 50 ml of dichloromethane, 10 drops of trifluoroacetic acid were added thereto, and the mixture was stirred at 25 °C for 24 hours under a nitrogen stream. After adding water, the organic layer was separated, washed with 50 ml of saturated brine, and then magnesium sulfate was added for filtration. The solvent was removed from the filtrate by an evaporator to obtain the pyrrolomethane compound (2-2) as a residue.

[1356] The obtained pyrrolomethane compound (2-2) was dissolved in 50 mL of 1,2-dichloroethane, 0.9 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was added, and the mixture was stirred at room temperature (25 °C) for 2 hours under a nitrogen stream. After confirming the formation of compound (2-3) by LC-MS analysis, 5.4 mL of diisopropylethylamine and 3.9 mL of boron trifluoride diethyl ether complex were then added, and the mixture was stirred at 80 °C for 1 hour. After cooling the reaction solution to room temperature, 50 mL of water was injected and the mixture was extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of water, and then magnesium sulfate was added for filtration. The solvent was removed from the filtrate by an evaporator, and then the residue was purified by silica gel column chromatography (n-heptane / toluene = 1 / 2, volume ratio). Further, 50 mL of methanol was added to the concentrated purified product, and the mixture was heated and stirred at 60 °C for 10 minutes and then cooled. The precipitated solid was filtered and vacuum dried to obtain 1.7 g of a purple-red powder. By LC-MS analysis of the obtained powder, it was confirmed that the purple-red powder was a pyrromethene metal complex, i.e., compound RD-2.

[1357] Compound RD-2: MS (m / z) molecular weight; 817

[1358] For compound RD-2, using an oil diffusion pump at 1×10 -3Sublimation purification was carried out at 270 °C under a pressure of Pa. The solid adhering to the glass tube wall was recovered, and a purity of 99% was confirmed by LC-MS analysis.

[1359] The luminescence properties in a solution of compound RD-2 are shown below.

[1360] The singlet energy S1 of compound RD-2 was measured by the solution method described above. The main peak wavelength λ of compound RD-2 was measured by the same method as the main peak wavelength λ of compound RD-1 described above.

[1361] Main peak wavelength λ of compound RD-2: 622 nm

[1362] Singlet energy S1 of compound RD-2: 1.99 eV

[1363] [Chemical Formula 152]

[1364]

[1365] [Synthesis Example 4: Synthesis of Compound RD-3]

[1366] A mixed solution of 2.0 g of pyrrole compound (3-1), 1.2 g of 1-naphthoyl chloride, and 60 mL of o-xylene was heated and stirred at 130 °C for 5 hours under a nitrogen stream. After cooling to room temperature (25 °C), methanol was added, the precipitated solid was filtered, and vacuum drying was performed to obtain 2.5 g of compound (3-2).

[1367] Next, a mixed solution of 2.5 g of compound (3-2), 1.7 g of pyrrole compound (3-1), 2.9 g of trifluoromethanesulfonic anhydride, and 100 mL of toluene was heated and stirred at 110 °C for 6 hours under a nitrogen stream. After cooling to room temperature, 100 mL of water was poured in and extraction was performed with 100 mL of ethyl acetate. After washing the organic layer with 50 mL of water, magnesium sulfate was added and filtration was carried out. The solvent was removed from the filtrate by an evaporator to obtain the pyrromethene body (3-3) as a residue.

[1368] Next, 5.4 mL of diisopropylethylamine and 3.9 mL of boron trifluoride diethyl ether complex were added to a mixed solution of the obtained pyrromethylidene body (3-3) and 100 mL of toluene under a nitrogen stream, and the mixture was stirred at 80 °C for 1 hour. Then, 100 mL of water was injected and extraction was carried out with 100 mL of ethyl acetate. After washing the organic layer with 50 mL of water, magnesium sulfate was added and filtration was performed. The solvent was removed from the filtrate using an evaporator, and then the residue was purified by silica gel column chromatography (heptane / toluene = 1 / 2, volume ratio). Further, 100 mL of methanol was added to the concentrated purified product, and the mixture was heated and stirred at 60 °C for 10 minutes and then cooled. The precipitated solid was filtered and dried under vacuum to obtain 2.1 g of a purple-red powder. The obtained powder was analyzed by LC-MS, and it was confirmed that the purple-red powder was a pyrromethylidene metal complex, that is, compound RD-3.

[1369] Compound RD-3: MS (m / z) 842 [M+H] +

[1370] Compound RD-3 was sublimation-purified at 290 °C under a pressure of 1×10 -3 Pa using an oil diffusion pump. The solid adhering to the glass tube wall was recovered, and it was confirmed by LC-MS analysis that the purity was 99%.

[1371] The following shows the luminescence characteristics of compound RD-3 in solution.

[1372] The singlet energy S1 of compound RD-3 was measured by the solution method described above. The main peak wavelength λ of compound RD-3 was measured by the same method as the main peak wavelength λ of compound RD-1 described above.

[1373] Main peak wavelength λ of compound RD-3: 613 nm

[1374] Singlet energy S1 of compound RD-3: 2.01 eV

[1375] [Chemical 153]

[1376]

[1377] Explanation of reference numerals

[1378] 1 Organic EL element

[1379] 2 Substrate

[1380] 3 Anode

[1381] 4 Cathode

[1382] 5 Light-emitting layer

[1383] 6 First layer

[1384] 7 The second layer

[1385] 10 The organic layer.

Claims

1. An organic electroluminescent element, characterized in that, comprising: an anode; a cathode; a light-emitting layer, disposed between the anode and the cathode; a first layer, disposed between the anode and the light-emitting layer and adjacent to the light-emitting layer; a second layer, disposed between the cathode and the light-emitting layer and adjacent to the light-emitting layer, the light-emitting layer comprising a first compound, a second compound, and a third compound, the first layer comprising a compound represented by the following general formula (A), the second layer comprising a compound represented by the following general formula (B), the first compound being a fluorescent compound represented by the following general formula (1), the second compound being a delayed fluorescence compound represented by the following general formula (2), the third compound being represented by the following general formula (3), the singlet energy S1(M1) of the first compound, the singlet energy S1(M2) of the second compound, and the singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 1): S1(M3) > S1(M2) > S1(M1) … (Equation 1), in the general formula (A), Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 are each independently a hydrogen atom or a substituent, and Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 as substituents are each independently, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, Rc1 is a hydrogen atom or a substituent, or the group of Rc1 and Rc2 are bonded to each other to form a ring, and Rc1 as a substituent is, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, Rc2 is a hydrogen atom or a substituent, or the group of Rc1 and Rc2 are bonded to each other to form a ring. When the group of Rc1 and Rc2 are bonded to each other to form a ring, the ring contains at least a five-membered ring, and the five-membered ring contains at least one of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms. Herein, Rc1 and Rc2 are not simultaneously hydrogen atoms, Rc2 as a substituent is, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted amino group, in the general formula (B), X1 to X3 are each independently a nitrogen atom or CR1, wherein at least one of X1 to X3 is a nitrogen atom, R1 is a hydrogen atom or a substituent, R1 as a substituent is each independently, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or Aryloxy groups with 6 to 30 ring carbon atoms, which may or may not be substituted, Ar1 and Ar2 are each independently, represented by the following general formula (1B), or are aryl groups with 6 to 30 ring carbon atoms, which may or may not be substituted, or heteroaryl groups with 5 to 30 ring atoms, which may or may not be substituted, A is represented by the following general formula (1B), In the general formula (1B), HAr is represented by the following general formula (2B), a is 1, 2, 3, 4 or 5, When a is 1, L1 is a single bond or a divalent linking group, When a is 2, 3, 4 or 5, L1 is a trivalent or higher up to hexavalent linking group, Multiple HArs are the same as or different from each other, The linking group is a group derived from an aryl group with 6 to 30 ring carbon atoms, which may or may not be substituted, a group derived from a heteroaryl group with 5 to 30 ring atoms, which may or may not be substituted, a group derived from a group formed by bonding two groups selected from the group consisting of an aryl group with 6 to 30 ring carbon atoms, which may or may not be substituted, and a heteroaryl group with 5 to 30 ring atoms, which may or may not be substituted, to each other, or a group derived from a group formed by bonding three groups selected from the group consisting of an aryl group with 6 to 30 ring carbon atoms, which may or may not be substituted, and a heteroaryl group with 5 to 30 ring atoms, which may or may not be substituted, to each other, In addition, the groups formed by bonding to each other are the same as or different from each other, In the general formula (2B), X 11 ~X 18 are each independently a nitrogen atom, CR 13 or a carbon atom bonded to L1, Multiple Rs 13 identical to or different from each other, Y1 is an oxygen atom, a sulfur atom, NR 18 , SiR 11 R 12 , CR 14 R 15 , a nitrogen atom bonded to L1, a silicon atom respectively bonded to R 16 and L1, or a carbon atom respectively bonded to R 17 and L1. Among them, X is bonded to L1 11 ~X 18 , R 11 ~R 12 and R 14 ~R 15 in the carbon atoms, and any one of the nitrogen atom, silicon atom and carbon atom in Y1 R 11 and R 12 are the same as or different from each other, R 14 and R 15 are the same as or different from each other, R 11 to R 18 are each independently a hydrogen atom or a substituent, or adjacent R 13 groups, R 11 and R 12 groups, and also R 14 and R 15 any one or more groups among the groups bond to each other to form a ring, R as a substituent 11 ~R 18 are each independently a halogen atom, a cyano group, an aryl group with 6 to 30 ring carbon atoms, which may or may not be substituted, a heteroaryl group with 5 to 30 ring atoms, which may or may not be substituted, an alkyl group with 1 to 30 carbon atoms, which may or may not be substituted, an alkenyl group with 2 to 30 carbon atoms, which may or may not be substituted, an alkynyl group with 2 to 30 carbon atoms, which may or may not be substituted, a silyl group, which may or may not be substituted, an alkoxy group with 1 to 30 carbon atoms, which may or may not be substituted, an aralkyl group with 7 to 30 carbon atoms, which may or may not be substituted, or aryloxy groups with 6 to 30 ring carbon atoms, which may or may not be substituted, In the general formula (1), X is a nitrogen atom or a carbon atom bonded to Y, Y is a hydrogen atom or a substituent, R 21 ~R 26 are each independently a hydrogen atom or a substituent, or R 21 and R 22 of the group, R 22 and R 23 of the group, R 24 and R 25 of the group, and also R 25 and R 26 any one or more of the groups of form a ring by bonding to each other Y and R as substituents 21 ~R 26 Each independently from an alkyl group with 1 to 30 carbon atoms, which may or may not be substituted, a haloalkyl group with 1 to 30 carbon atoms, which may or may not be substituted, a cycloalkyl group with 3 to 30 ring carbon atoms, which may or may not be substituted, an aryl group with 6 to 30 ring carbon atoms, which may or may not be substituted, an alkoxy group with 1 to 30 carbon atoms, which may or may not be substituted, a haloalkoxy group with 1 to 30 carbon atoms, which may or may not be substituted, an alkylthio group with 1 to 30 carbon atoms, which may or may not be substituted, aryloxy groups with 6 to 30 ring carbon atoms, which may or may not be substituted, arylthio groups with 6 to 30 ring carbon atoms, which may or may not be substituted, an alkenyl group with 2 to 30 carbon atoms, which may or may not be substituted, an aralkyl group with 7 to 30 carbon atoms, which may or may not be substituted, a heteroaryl group with 5 to 30 ring atoms, which may or may not be substituted, a halogen atom, a carboxyl group, an ester group, which may or may not be substituted, a carbamoyl group, which may or may not be substituted, an amino group, which may or may not be substituted, a nitro group, a cyano group, a silyl group, which may or may not be substituted, and a siloxy group, which may or may not be substituted, are selected from the group consisting of, Z 21 and Z 22 are each independently a substituent, or Z 21 and Z 22 are bonded to each other to form a ring, and Z as a substituent 21 and Z 22 are each independently from a halogen atom, an alkyl group with 1 to 30 carbon atoms, which may or may not be substituted, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, In the general formula (2), D1 is a group represented by the following general formula (2-1), D2 is a group represented by the following general formula (2-2), and a plurality of D2 are the same groups as each other, In the general formula (2-1), X4 is an oxygen atom or a sulfur atom, and R 131 ~R 140 are each independently a hydrogen atom or a substituent, R as a substituent 131 ~R 140 are each independently A substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms, * represents the position bonded to the benzene ring in the general formula (2), In the general formula (2-2), R 161 ~R 168 are each independently a hydrogen atom or a substituent, R as a substituent 161 ~R 168 are each independently A halogen atom, A substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms, * each independently represents the position bonded to the benzene ring in the general formula (2), In the general formula (3), A 31 is a group represented by the following general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e) or general formula (31f), R 31 ~R 38 are each independently a hydrogen atom or a substituent, R 401 ~R 404 and R 409 ~R 412 are each independently a hydrogen atom or a substituent, R as a substituent 31 ~R 38 There is also R as a substituent 401 ~R 404 And R 409 ~R 412 Each independently is A halogen atom, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, A hydroxyl group, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, An amino group, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A mercapto group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, In the general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e) and general formula (31f), R 310 ~R 319 are each independently a hydrogen atom or a substituent, R 320 ~R 329 are each independently a hydrogen atom or a substituent, R 330 ~R 339 Each independently represents a hydrogen atom or a substituent, R 340 ~R 349 Each independently represents a hydrogen atom or a substituent, R 350 ~R 359 Each independently represents a hydrogen atom or a substituent, R 360 ~R 369 are each independently a hydrogen atom or a substituent, R as a substituent 310 ~R 319 、R 320 ~R 329 、R 330 ~R 339 、R 340 ~R 349 、R 350 ~R 359 and R 360 ~R 369 are each independently the same as R as a substituent in the general formula (3), and * each independently represents the position bonded to the benzene ring having R 31 ~R 38 There is also R as a substituent 401 ~R 404 and R 409 ~R 412 in the general formula (3), and * each independently represents the position bonded to the benzene ring having R 401 ~R 404 in the general formula (3).

2. The organic electroluminescent element according to claim 1, wherein Rc1 is a hydrogen atom or a substituent, Rc2 is a hydrogen atom or a substituent.

3. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (A) is a compound represented by the following general formula (1X), the following general formula (1Y) or the following general formula (1Z), in the general formula (1X), the general formula (1Y) and the general formula (1Z), Ra1 to Ra5 and Rb1 to Rb5 are respectively synonymous with Ra1 to Ra5 and Rb1 to Rb5 in the general formula (A), R A is a hydrogen atom or a substituent, R as a substituent A Each is independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, in the case where there are a plurality of Rs A Rs A are the same as or different from each other.

4. The organic electroluminescent element according to claim 3, characterized in that, In the general formula (1X), the general formula (1Y), and the general formula (1Z), R A is a hydrogen atom.

5. The organic electroluminescent element according to claim 3, wherein, the compound represented by the general formula (A) is a compound represented by the general formula (1X).

6. The organic electroluminescent element according to claim 1, wherein Ra1 to Ra5 and Rb1 to Rb5 are each independently a hydrogen atom or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

7. The organic electroluminescent element according to claim 1, wherein one of Ra1 to Ra5 is a substituent, and Ra1 to Ra5 other than this substituent are hydrogen atoms, one of Rb1 to Rb5 is a substituent, and Rb1 to Rb5 other than this substituent are hydrogen atoms, Rc3 to Rc5 are hydrogen atoms.

8. The organic electroluminescent element according to claim 1, wherein the following general formula (1A) is a partial structure of the compound represented by the general formula (A), the part represented by the general formula (1A) is a group represented by any one of the following general formulas (1A-1) to (1A-10), in the general formula (1A), Rc1 is synonymous with Rc1 in the general formula (A), Rc2 is synonymous with Rc2 in the general formula (A), Rc3 to Rc5 are each independently synonymous with Rc3 to Rc5 in the general formula (A), and * represents the bonding site to the nitrogen atom in the compound represented by the general formula (A), In the general formulas (1A-1) to (1A-10), R A is a hydrogen atom or a substituent, and R as a substituent A are each independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, In the case where there are multiple Rs A Rs A are the same as or different from each other, and * represents the site bonded to the nitrogen atom in the compound represented by the general formula (A).

9. The organic electroluminescent element according to claim 8, wherein, In the general formulas (1A-1) to (1A-10), R A is a hydrogen atom.

10. The organic electroluminescent element according to any one of claims 1 to 5, wherein In the general formula (A), 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 is a hydrogen atom or a substituent, and R as a substituent B are each independently A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted silyl group, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, In the case where there are multiple Rs B , the Rs B are the same as or different from each other, and * indicates the bonding sites to the benzene rings respectively bonded to Ra1 to Ra5 and Rb1 to Rb5 in the compound represented by the general formula (A).

11. The organic electroluminescent element according to claim 10, wherein In the general formulas (1B-1) to (1B-10), R B is a hydrogen atom.

12. The organic electroluminescent element according to claim 1, wherein The ionization potential Ip of the compound represented by the general formula (A) is 5.78 eV or more.

13. The organic electroluminescent element according to claim 1, wherein The ionization potential Ip of the compound represented by the general formula (A) is 5.80 eV or more.

14. The organic electroluminescent element according to claim 1, characterized in that, The ionization potential Ip of the compound represented by the general formula (A) is 5.85 eV or more.

15. The organic electroluminescent element according to any one of claims 12 to 14, characterized in that, The ionization potential Ip is a value obtained by irradiating a material to be measured with light using a photoelectron spectroscopy apparatus under atmospheric pressure and measuring the amount of electrons generated due to charge separation at this time.

16. The organic electroluminescent element according to claim 1, wherein The compound represented by the general formula (A) is any one of the following compounds, 17. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (B), two or three of X1 to X3 are nitrogen atoms.

18. The organic electroluminescent element according to claim 1, wherein When two of X1 to X3 are nitrogen atoms, X1 and X2 are nitrogen atoms, and X3 is CR1.

19. The organic electroluminescent element according to claim 1, wherein The compound represented by the general formula (B) is represented by the following general formula (21), In the general formula (21), A, Ar1, and Ar2 are synonymous with A, Ar1, and Ar2 in the general formula (B), respectively.

20. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (1B), L1 is a single bond.

21. The organic electroluminescent element according to claim 1, wherein L1 as a linking group is a residue having a valence of three or more and six or less derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

22. The organic electroluminescent element according to claim 1, wherein L1 as a linking group is a divalent or trivalent residue derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a divalent or trivalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

23. The organic electroluminescent element according to claim 22, wherein L1 as a linking group is a divalent or trivalent residue derived from any one of benzene, biphenyl, terphenyl, naphthalene, and phenanthrene.

24. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (1B), 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 ring carbon atoms or a divalent residue derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

25. The organic electroluminescent element according to claim 1, wherein In the general formula (1B), a is 2, and L1 is a linking group. L1 as a linking group is a trivalent residue derived from an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted, or a trivalent residue derived from a heteroaryl group having 5 to 30 ring atoms which may be substituted or unsubstituted.

26. The organic electroluminescent element according to claim 1, wherein when a is 1, L1 is a divalent linking group, and the general formula (1B) is represented by the following general formula (11B-1); when a is 2, L1 is a trivalent linking group, and the general formula (1B) is represented by the following general formula (11B-2), and HArs are the same or different. (HAr)-L1- (11B-1) In the general formulas (11B-1) and (11B-2), L1 is a divalent or trivalent linking group, and the linking group is a group derived from an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted, a group derived from a heteroaryl group having 5 to 30 ring atoms which may be substituted or unsubstituted, a group derived from a group formed by bonding two groups selected from the group consisting of an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted and a heteroaryl group having 5 to 30 ring atoms which may be substituted or unsubstituted to each other, or a group derived from a group formed by bonding three groups selected from the group consisting of an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted and a heteroaryl group having 5 to 30 ring atoms which may be substituted or unsubstituted to each other.

27. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (2B), Y1 is NR 18 , an oxygen atom, a sulfur atom, CR 14 R 15 , or a nitrogen atom bonded to L1.

28. The organic electroluminescent element according to claim 1, wherein In the general formula (2B), Y1 is CR 14 R 15 .

29. The organic electroluminescent element according to claim 28, wherein In the general formula (2B), when Y1 is CR 14 R 15 , any one of X 11 ~X 18 is a carbon atom bonded to L1, and the other X 11 ~X 18 are nitrogen atoms or CR 13 .

30. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (2B), Y1 is NR 18 or a nitrogen atom bonded to L1.

31. The organic electroluminescent element according to claim 30, characterized in that, In the general formula (2B), when Y1 is NR 18 , one of X 11 to X 18 is a carbon atom bonded to L1, and the other X 11 to X 18 are nitrogen atoms or CR 13 .

32. The organic electroluminescent element according to claim 30, wherein, In the general formula (2B), when Y1 is a nitrogen atom bonded to L1, X 11 ~X 18 are each independently a nitrogen atom or CR 13 .

33. The organic electroluminescent element according to claim 1, wherein In the general formula (2B), Y1 is an oxygen atom or a sulfur atom.

34. The organic electroluminescent element according to claim 1, wherein 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 rest are CR 13 .

35. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (2B), X 13 or X 16 is a carbon atom bonded to L1.

36. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (B) is any one of the following compounds.

37. The organic electroluminescent element according to claim 1, wherein In the general formulas (2-1) and (2-2), R 131 ~R 140 and R 161 ~R 168 are each independently a hydrogen atom, an aryl group having 6 to 14 ring carbon atoms which may be substituted or unsubstituted, a heterocyclic group having 5 to 14 ring atoms which may be substituted or unsubstituted, or an alkyl group having 1 to 6 carbon atoms which may be substituted or unsubstituted.

38. The organic electroluminescent element according to claim 1, wherein In the general formulas (2-1) and (2-2), R 131 ~R 140 and R 161 ~R 168 are each independently a hydrogen atom, an aryl group having 6 to 14 ring carbon atoms which may be substituted or unsubstituted, or an alkyl group having 1 to 6 carbon atoms which may be substituted or unsubstituted.

39. The organic electroluminescent element according to claim 37 or 38, wherein In the general formulas (2-1) and (2-2), R 131 ~R 140 and R 161 ~R 168 are each independently a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms which may be substituted or unsubstituted.

40. The organic electroluminescent element according to claim 37 or 38, characterized in that, In the general formula (2-2), R 161 , R 163 , R 166 , and R 168 has a substituent, which is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R 162 , R 164 , R 165 , and R 167 are hydrogen atoms.

41. The organic electroluminescent element according to claim 37, wherein In the general formula (2-1), R 137 is a substituent, and R as the substituent 137 is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R 131 to R 136 and R 138 to R 140 are hydrogen atoms.

42. The organic electroluminescent element according to claim 37 or 38, characterized in that, In the general formulas (2-1) and (2-2), R 131 ~R 140 and R 161 ~R 168 are hydrogen atoms.

43. The organic electroluminescent element according to claim 1, wherein, In the general formula (2-1), X4 is a sulfur atom.

44. The organic electroluminescent element according to claim 1, characterized in that, In the general formula (2-1), X4 is an oxygen atom.

45. The organic electroluminescent element according to claim 1, wherein in the second compound, the group represented by the general formula (2-2) is any one of the groups represented by the following general formulas (2-20) to (2-26). In the general formulas (2-20) to (2-26), * each independently represents a bonding position to the benzene ring in the general formula (2).

46. The organic electroluminescent element according to claim 1, wherein the second compound is any one of the following compounds.

47. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (n), in the general formula (n), Ar 1001 and Ar 1002 each independently from selected from the group consisting of an aryl group having 6 to 30 ring carbon atoms which may or may not be substituted, and a heteroaryl group having 5 to 30 ring atoms which may or may not be substituted, R 1001 ~R 1005 are each independently a hydrogen atom or a substituent, or R 1001 and R 1002 in the group of, R 1002 and Ar 1001 in the group of, Ar 1002 and R 1003 in the group of, and also R 1003 and R 1004 in the group of, any one or more groups of which are bonded to each other to form a ring, R as a substituent 1001 ~R 1005 are each independently selected from an alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a halogenated alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a cycloalkyl group having 3 to 30 ring carbon atoms which may or may not be substituted, an aryl group having 6 to 30 ring carbon atoms which may or may not be substituted, an alkoxy group having 1 to 30 carbon atoms which may or may not be substituted, a halogenated alkoxy group having 1 to 30 carbon atoms which may or may not be substituted, an alkylthio group having 1 to 30 carbon atoms which may or may not be substituted, an aryloxy group having 6 to 30 ring carbon atoms which may or may not be substituted, an arylthio group having 6 to 30 ring carbon atoms which may or may not be substituted, an alkenyl group having 2 to 30 carbon atoms which may or may not be substituted, a heteroaryl group having 5 to 30 ring atoms which may or may not be substituted, a halogen atom, a carboxyl group, an ester group which may or may not be substituted, a carbamoyl group which may or may not be substituted, an amino group which may or may not be substituted, a nitro group, a cyano group, a silyl group which may or may not be substituted, and a siloxanyl group which may or may not be substituted, Z 1001 and Z 1002 respectively and independently from a halogen atom, an alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a halogenated alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a cycloalkyl group having 3 to 30 ring carbon atoms which may or may not be substituted, an aryl group having 6 to 30 ring carbon atoms which may or may not be substituted, an alkoxy group having 1 to 30 carbon atoms which may or may not be substituted, a halogenated alkoxy group having 1 to 30 carbon atoms which may or may not be substituted, and selected from the group consisting of an aryloxy group having 6 to 30 ring carbon atoms which may or may not be substituted.

48. The organic electroluminescent element according to claim 47, wherein, In the general formula (n), Ar 1001 and Ar 1002 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

49. The organic electroluminescent element according to claim 47, characterized in that, In the general formula (n), Ar 1001 and Ar 1002 are each independently a monocyclic or fused ring.

50. The organic electroluminescent element according to any one of claims 47 to 49, characterized in that, In the general formula (n), Ar 1001 and Ar 1002 are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

51. The organic electroluminescent element according to claim 47, wherein In the general formula (n), R 1001 and R 1004 at least one of which is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

52. The organic electroluminescent element according to claim 51, characterized in that, In the general formula (n), R 1001 and R 1004 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

53. The organic electroluminescent element according to claim 47, characterized in that, In the general formula (n), R 1002 and R 1003 are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

54. The organic electroluminescent element according to claim 53, wherein In the general formula (n), R 1002 and R 1003 are a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

55. The organic electroluminescent element according to claim 47, wherein, In the general formula (n), R 1005 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

56. The organic electroluminescent element according to claim 55, characterized in that, In the general formula (n), R 1005 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted dibenzofuranyl group.

57. The organic electroluminescent element according to claim 47, wherein In the general formula (n), Z 1001 and Z 1002 are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms.

58. The organic electroluminescent element according to claim 47, wherein the compound represented by the general formula (n) is a compound represented by the following general formula (n + 1A) or general formula (n + 1B), In the general formula (n + 1A), R 1001 , R 1002 , R 1004 , R 1005 , Ar 1001 , Z 1001 and Z 1002 are each independently synonymous with R 1001 , R 1002 , R 1004 , R 1005 , Ar 1001 , Z 1001 and Z 1002 in the general formula (n), In the general formula (n + 1B), R 1001 , R 1004 , R 1005 , Z 1001 and Z 1002 are respectively independently synonymous with R 1001 , R 1004 , R 1005 , Z 1001 and Z 1002 in the general formula (n), Ar 1003 and Ar 1004 independently from selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms which may or may not be substituted, and an aromatic heterocyclic ring having 5 to 30 ring atoms which may or may not be substituted, B 1 is a crosslinked structure obtained by connecting and bonding more than 3 atoms in series, and the atoms are selected from a carbon atom which may or may not be substituted, a silicon atom which may or may not be substituted, a nitrogen atom which may or may not be substituted, a phosphorus atom which may or may not be substituted, an oxygen atom, and a sulfur atom, C 1 is a crosslinked structure obtained by connecting and bonding more than 1 atom in series, and the atoms are selected from a carbon atom which may or may not be substituted, a silicon atom which may or may not be substituted, a nitrogen atom which may or may not be substituted, a phosphorus atom which may or may not be substituted, an oxygen atom, and a sulfur atom, Among them, in B 1 When it is trimethylene, R 1004 is not a hydrogen atom or a halogen atom.

59. The organic electroluminescent element according to claim 58, wherein In the general formula (n + 1A) and the general formula (n + 1B), the number of atoms in the crosslinked structure B 1 i.e., the number of atoms in the tandem bond, the number of atoms forming a ring in Ar 1003 and the total of two carbon atoms constituting the pyrromethylene skeleton are 30 or less. In the general formula (n + 1B), the number of atoms in the crosslinked structure C 1 i.e., the number of atoms bonded in series, the number of atoms forming a ring in Ar 1004 and the total number of two carbon atoms constituting the pyrromethylene skeleton are 30 or less.

60. The organic electroluminescent element according to claim 58 or 59, wherein B 1 A crosslinked structure represented by the following general formula (n + 2A) or general formula (n + 2B): In the general formula (n + 2A), R 1011 ~R 1016 are each independently a hydrogen atom or a substituent, or one or more of the groups formed by bonding together two or more adjacent ones of R 1011 ~R 1016 bond to each other to form a ring, In the general formula (n + 2B), R 1011 ~R 1014 are each independently a hydrogen atom or a substituent, or one or more of the groups formed by bonding together two or more adjacent ones of R 1011 ~R 1014 bond to each other to form a ring R as a substituent 1011 ~R 1016 are each independently an alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a halogenated alkyl group having 1 to 30 carbon atoms which may or may not be substituted, a cycloalkyl group having 3 to 30 ring carbon atoms which may or may not be substituted, an aryl group having 6 to 30 ring carbon atoms which may or may not be substituted, a heteroaryl group having 5 to 30 ring atoms which may or may not be substituted, an alkoxy group having 1 to 30 carbon atoms which may or may not be substituted, A substituted or unsubstituted haloalkyloxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A halogen atom, A carboxyl group, A substituted or unsubstituted amino group, A nitro group, A cyano group, A substituted or unsubstituted silyl group, A hydroxyl group, An ester group, A siloxanyl group, or A carbamoyl group, * indicates the connecting part to the pyrrole ring in the general formula (n + 1A) and the general formula (n + 1B), and ** indicates the connecting part to Ar 1003 The connecting part of 61. The organic electroluminescent element according to claim 60, wherein, In the general formula (n + 2A) and the general formula (n + 2B), R 1011 ~R 1016 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

62. The organic electroluminescent element according to claim 58, wherein, In the general formula (n + 1A) and the general formula (n + 1B), B 1 is a crosslinked structure obtained by bonding three atoms in series.

63. The organic electroluminescent element according to claim 58, wherein In the general formula (n + 1B), C 1 is a crosslinked structure obtained by connecting one or more and three or fewer atoms in series The atoms constituting said C 1 are selected from substituted or unsubstituted carbon atoms, oxygen atoms, and sulfur atoms.

64. The organic electroluminescent element according to claim 58, wherein R 1005 a group represented by the following general formula (n + 3), In the general formula (n + 3), R 1021 and R 1022 each independently from A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and Selected from the group consisting of a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, R 1023 ~R 1025 are each independently a hydrogen atom or a substituent, or R 1023 and R 1024 in the group of, and also R 1024 and R 1025 in the group of, any one or more groups of which are bonded to each other to form a ring R as a substituent 1023 ~R 1025 are each independently A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkyloxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, A substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted acyl group having 1 to 30 carbon atoms, A halogen atom, A carboxyl group, A substituted or unsubstituted amino group, A nitro group, A cyano group, A substituted or unsubstituted silyl group, A hydroxyl group, An ester group, A siloxanyl group, or A carbamoyl group, In the general formula (n + 3), *** represents the position bonded to the carbon atom bonded to R in the general formula (n). 1005 The position bonded to the carbon atom bonded to the bond.

65. The organic electroluminescent element according to claim 64, wherein In the general formula (n + 3), R 1021 and R 1022 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

66. The organic electroluminescent element according to claim 64 or 65, characterized in that, In the general formula (n + 3), when R 1021 and R 1022 is an alkyl group, it is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. When R 1021 and R 1022 is an aryl group, it is a substituted or unsubstituted phenyl group. When R 1021 and R 1022 is a heteroaryl group, it is a substituted or unsubstituted monocyclic heteroaryl group having 5 to 6 ring-forming atoms.

67. The organic electroluminescent element according to claim 64 or 65, characterized in that, In the general formula (n + 3), R 1023 ~R 1025 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a halogen atom, a substituted or unsubstituted amino group, or a cyano group.

68. The organic electroluminescent element according to claim 1, characterized in that, The first compound exhibits red luminescence or green luminescence.

69. The organic electroluminescent element according to claim 68, wherein When the first compound is a red fluorescent compound, the main peak wavelength of the first compound is 600 nm or more and 660 nm or less, When the first compound is a green fluorescent compound, the main peak wavelength of the first compound is 500 nm or more and 560 nm or less.

70. The organic electroluminescent element according to claim 68, wherein When the first compound is a red fluorescent compound, the main peak wavelength of the first compound is 600 nm or more and 640 nm or less, When the first compound is a green fluorescent compound, the main peak wavelength of the first compound is 500 nm or more and 540 nm or less.

71. The organic electroluminescent element according to claim 68, wherein when the first compound is a red fluorescent compound, the main peak wavelength of the first compound is 610 nm or more and 630 nm or less, when the first compound is a green fluorescent compound, the main peak wavelength of the first compound is 510 nm or more and 530 nm or less.

72. The organic electroluminescent element according to any one of claims 69 to 71, characterized in that, The main peak wavelength is a value obtained by preparing a 5 μmol / L toluene solution of the compound to be measured, adding it to a quartz cell to make a sample, and measuring the emission spectrum of the sample at room temperature, i.e., 300 K, using a spectrophotometer. In the emission spectrum, the vertical axis is the emission intensity and the horizontal axis is the wavelength.

73. The organic electroluminescent element according to claim 1, wherein the first compound is any one of the following compounds, 74. The organic electroluminescent element according to claim 1, characterized in that, the third compound is a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence.

75. The organic electroluminescent element according to claim 1, wherein The energy gap T at 77 [K] of the first compound 77K (M1) and the energy gap T at 77 [K] of the second compound 77K (M2) and the energy gap T at 77 [K] of the third compound 77K (M3) satisfy the relationship of the following mathematical formula (Formula 2), T 77K (M3) > T 77K (M2) > T 77K (M1)…(Number 2).

76. The organic electroluminescent element according to claim 1, wherein The singlet energy S1(M2) of the second compound and the energy gap T at 77 [K] of the second compound 77K (M2) The difference △ST(M2) satisfies any one of the following mathematical formulas (Formula 1A) to (Formula 1D), △ST(M2) = S1(M2) - T 77K (M2) < 0.3 eV (Equation 1A) △ST(M2) = S1(M2) - T 77K (M2) < 0.2 eV (Equation 1B) △ST(M2) = S1(M2) - T 77K (M2) < 0.1 eV (Equation 1C) △ST(M2) = S1(M2) - T 77K (M2) < 0.01 eV (Equation 1D).

77. The organic electroluminescent element according to claim 1, wherein The singlet energy S1(M1) of the first compound and the energy gap T 77K (M1) at 77 [K] of the first compound, the difference △ST(M1) satisfies the relationship of the following mathematical formula (Formula 1E), △ST(M1) = S1(M1) - T 77K (M1) > 0.3 [eV] … (Equation 1E).

78. The organic electroluminescent element according to claim 1, wherein The singlet energy S1(M3) of the third compound and the energy gap T at 77 [K] of the third compound 77K (M3) The difference △ST(M3) satisfies the relationship of the following mathematical formula (Formula 1F), △ST(M3) = S1(M3) - T 77K (M3) > 0.3 [eV] … (Equation 1F).

79. The organic electroluminescent element according to claim 1, characterized in that, The energy gap T at 77 [K] of the third compound 77K (M3) is 2.9 eV or more.

80. The organic electroluminescent element according to any one of claims 75 to 79, wherein Dissolve the compound to be measured in EPA at a concentration of 10 μmol / L. The volume ratio of the EPA is diethyl ether:iso-pentane:ethanol = 5:5:

2. Add this solution to a quartz cell as a measurement sample. For this measurement sample, measure the phosphorescence spectrum at 77 [K]. The vertical axis of this phosphorescence spectrum is the phosphorescence emission intensity, and the horizontal axis is the wavelength. Draw a tangent to the rising edge on the short wavelength side of this phosphorescence spectrum. Based on the wavelength value λ edge [nm] of the intersection point of this tangent and the horizontal axis, use the energy calculated according to the following conversion formula (F1) as the energy gap T at 77 [K] 77K , Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge .

81. The organic electroluminescent element according to claim 1 and any one of claims 76 to 78, wherein a 10 μmol / L toluene solution of the compound to be measured is prepared, added to a quartz cell to make a sample, and the absorption spectrum of the sample is measured at 300 K. The vertical axis of the absorption spectrum is the absorption intensity and the horizontal axis is the wavelength. A tangent is drawn to the descending edge on the long wavelength side of the absorption spectrum, and the wavelength value λedge [nm] of the intersection of the tangent and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy S1, Conversion formula (F2): S1 [eV] = 1239.85 / λedge.

82. The organic electroluminescent element according to claim 1, wherein in the light-emitting layer, the content of the first compound is 0.01% by mass or more and 10% by mass or less, the content of the second compound is 10% by mass or more and 80% by mass or less, the content of the third compound is 10% by mass or more and 80% by mass or less.

83. The organic electroluminescent element according to claim 1, wherein in the light-emitting layer, the content of the first compound is 0.01% by mass or more and 5% by mass or less, the content of the second compound is 10% by mass or more and 60% by mass or less, the content of the third compound is 10% by mass or more and 80% by mass or less.

84. The organic electroluminescent element according to claim 1, wherein in the light-emitting layer, the content of the first compound is 0.01% by mass or more and 1% by mass or less, the content of the second compound is 20% by mass or more and 60% by mass or less, The content rate of the third compound is 10% by mass or more and 80% by mass or less.

85. The organic electroluminescent element according to claim 1, characterized in that In the case of "substituted or unsubstituted", the substituents are A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, A substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted acyl group having 1 to 30 carbon atoms, A halogen atom, A carboxyl group, A substituted or unsubstituted amino group, A nitro group, A cyano group, A substituted or unsubstituted silyl group, A substituted phosphoryl group, A hydroxyl group, A substituted phosphino group, An ester group, A siloxanyl group, or A carbamoyl group.

86. The organic electroluminescent element according to claim 1, wherein, The light-emitting layer does not contain a phosphorescent material.

87. The organic electroluminescent element according to claim 1, wherein The light-emitting layer does not contain a metal complex.

88. The organic electroluminescent element according to claim 1, wherein The main peak wavelength of the light emitted from the organic electroluminescent element is 500 nm or more and 560 nm or less.

89. The organic electroluminescent element according to claim 1, characterized in that, The main peak wavelength of the light emitted from the organic electroluminescent element is 600 nm or more and 660 nm or less.

90. The organic electroluminescent element according to claim 88 or 89, characterized in that, Measure the spectral emission luminance spectrum when a voltage is applied to the organic electroluminescent element such that the current density reaches 10 mA / cm 2 In the obtained spectral emission luminance spectrum, measure the peak wavelength of the emission spectrum at which the emission intensity is maximum, and use the value thus obtained as the main peak wavelength of the light emitted from the organic electroluminescent element.

91. An electronic device, characterized in that, An organic electroluminescent element according to any one of claims 1 to 90 is mounted.

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