Organic electroluminescent element, compound, and electronic device

Abstract

The present invention provides an organic electroluminescent element (1) having an anode (3), a cathode (4), and a light-emitting layer (5) included between the anode (3) and the cathode (4). The light-emitting layer (5) contains a delayed fluorescence compound M2 and a compound M3 represented by the general formula (3). The singlet energy S1(M2) of the compound M2 and the singlet energy S1(M3) of the compound M3 satisfy the relationship of the following mathematical formula (Equation 1). In the general formula (3), A 30 is a group represented by the general formula (3a) or the like. S1(M3) > S1(M2) … (Equation 1). #imgabs0#

Description

Technical Field

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

[0002] After applying a voltage 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 applied to full-color displays such as mobile phones and televisions, and the internal quantum efficiency of 25% is called the limit. Therefore, research for improving the performance of organic EL elements is underway.

[0004] For example, it is expected to use triplet excitons in addition to singlet excitons to make the organic EL element emit light more efficiently. Against this background, highly efficient fluorescent organic EL elements using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and studied.

[0005] The TADF (Thermally Activated Delayed Fluorescence) 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] As a compound showing thermally activated delayed fluorescence property (hereinafter also referred to as TADF property compound), for example, a compound in which a donor site and an acceptor site are bonded within a molecule is known.

[0007] As documents related to organic EL elements, Patent Documents 1, 2, 3, and Non-Patent Document 1 can be cited.

[0008] Prior Art Documents

[0009] Patent Documents

[0010] Patent Document 1: Specification of Chinese Patent Application Publication No. 107793398

[0011] Patent Document 2: International Publication No. 2014 / 166585

[0012] Patent Document 3: Korean Patent Publication No. 2014-143618

[0013] Non-Patent Document

[0014] Non-Patent Document 1: *Nature Communications*, 2014, 5, 4016 Summary of the Invention

[0015] Technical Problem to be Solved by the Invention

[0016] In order to improve the performance of electronic devices such as displays, it is desired to further improve the performance of organic EL elements.

[0017] An object of the present invention is to provide a compound and an organic electroluminescent element that can achieve high performance, particularly improve luminous efficiency, and to provide an electronic device including the organic electroluminescent element.

[0018] Solution for Solving the Above Technical Problem

[0019] According to one aspect of the present invention, there is provided an organic electroluminescent element having an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer including a delayed fluorescence compound M2 and a compound M3 represented by the following general formula (3), and the singlet energy S1(M2) of the compound M2 and the singlet energy S1(M3) of the compound M3 satisfy the relationship of the following mathematical formula (Equation 1).

[0020] S1(M3) > S1(M2) … (Equation 1)

[0021]

Chemical Formula 1

[0022]

[0023] (In the general formula (3), A 30 is a group represented by the following general formula (3a), general formula (3b), general formula (3c), general formula (3d), general formula (3e), or general formula (3f).)

[0024]

Chemical Formula 2

[0025]

[0026]

Chemical Formula 3

[0027]

[0028]

Chemical Formula 4

[0029]

[0030] (In the general formulas (3a), (3b), (3c), (3d), (3e), and (3f),

[0031] X 31 、X 32 、X 33 、X 34 、X 35 and X 36 are each independently an oxygen atom, a sulfur atom, NR 371 or SiR 372 R 373 ,

[0032] R 371 、R 372 and R 373 are each independently a hydrogen atom or a substituent,

[0033] R 310 ~R 319 are each independently a hydrogen atom or a substituent, or a group of R 310 and R 311 , a group of R 311 and R 312 , a group of R 312 and R 313 , a group of R 314 and R 315 , a group of R 316 and R 317 , a group of R 317 and R 318 , and any one or more groups among the groups of R 318 and R 319 are bonded to each other to form a ring,

[0034] R 320 ~R 329 are each independently a hydrogen atom or a substituent, or a group of R 320 and R 321 , a group of R 321 and R 322 , a group of R 322 and R 323 , a group of R 324 and R 325 , a group of R 326 and R 327 , a group of R 327 and R 328 , and any one or more groups among the groups of R 328 and R 329 are bonded to each other to form a ring,

[0035] R330 ~R 339 are each independently a hydrogen atom or a substituent, or R 330 and R 331 of the group, R 331 and R 332 of the group, R 332 and R 333 of the group, R 335 and R 336 of the group, R 336 and R 337 of the group, and also R 337 and R 338 of the group, and any one or more of the groups bond to each other to form a ring,

[0036] R 340 ~R 349 are each independently a hydrogen atom or a substituent, or R 340 and R 341 of the group, R 341 and R 342 of the group, R 342 and R 343 of the group, R 345 and R 346 of the group, R 346 and R 347 of the group, and also R 347 and R 348 of the group, and any one or more of the groups bond to each other to form a ring,

[0037] R 350 ~R 359 are each independently a hydrogen atom or a substituent, or R 350 and R 351 of the group, R 351 and R 352 of the group, R 352 and R 353 of the group, R 354 and R 355 of the group, R 355 and R 356 of the group, R 356 and R 357 of the group, and also R 358 and R 359 of the group, and any one or more of the groups bond to each other to form a ring,

[0038] R 360 ~R 369 are each independently a hydrogen atom or a substituent, or R 360 and R 361 of the group, R 361 and R362 group of, R 362 and R 363 group of, R 364 and R 365 group of, R 365 and R 366 group of, R 366 and R 367 group of, and also R 368 and R 369 Any one or more of the groups in the group of, and R are bonded to each other to form a ring.

[0039] R as a substituent 371 , R 372 and R 373 , and also 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

[0040] a halogen atom

[0041] a cyano group

[0042] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms

[0043] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms

[0044] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms

[0045] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms

[0046] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms

[0047] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms

[0048] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms

[0049] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms

[0050] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms

[0051] a hydroxyl group

[0052] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0053] a substituted or unsubstituted aryloxy group having 6 to 30 ring-constituting carbon atoms,

[0054] an amino group,

[0055] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0056] a substituted or unsubstituted arylamino group having 6 to 60 ring-constituting carbon atoms,

[0057] a mercapto group,

[0058] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0059] a substituted or unsubstituted arylthio group having 6 to 30 ring-constituting carbon atoms,

[0060] * indicates the bonding position to L 30 .)

[0061] (In the general formula (3),

[0062] L 30 is

[0063] a substituted or unsubstituted arylene group having 6 to 22 ring-constituting carbon atoms,

[0064] a group formed by bonding two substituted or unsubstituted arylene groups having 6 to 22 ring-constituting carbon atoms, or

[0065] a group formed by bonding three substituted or unsubstituted arylene groups having 6 to 22 ring-constituting carbon atoms,

[0066] R 31 to R 38 are each independently a hydrogen atom or a substituent, or a group of R 31 and R 32 , a group of R 32 and R 33 , a group of R 33 and R 34 , a group of R 35 and R 36 , a group of R 36 and R 37 , and a group of R 37 and R 38 in any one or more of the groups bond to each other to form a ring,

[0067] L 30 when having a substituent, the substituent and R as a substituent 31 to R 38Each independently is,

[0068] a halogen atom,

[0069] a cyano group,

[0070] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0071] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0072] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0073] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0074] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0075] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0076] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0077] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0078] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0079] a hydroxyl group,

[0080] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0081] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0082] an amino group,

[0083] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0084] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0085] a mercapto group,

[0086] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0087] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms.)

[0088] According to one embodiment of the present invention, a compound represented by the following general formula (301) can be provided.

[0089]

Chemical 5

[0090]

[0091] (In the general formula (301), 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).)

[0092]

Chemical formula 6

[0093]

[0094]

Chemical formula 7

[0095]

[0096]

Chemical formula 8

[0097]

[0098] (In the general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e), and general formula (31f),

[0099] R 310 to R 319 are each independently a hydrogen atom or a substituent,

[0100] R 320 to R 329 are each independently a hydrogen atom or a substituent,

[0101] R 330 to R 339 are each independently a hydrogen atom or a substituent,

[0102] R 340 to R 349 are each independently a hydrogen atom or a substituent,

[0103] R 350 to R 359 are each independently a hydrogen atom or a substituent,

[0104] R 360 to R 369 are each independently a hydrogen atom or a substituent,

[0105] As substituents, R 310 to R 319 , R 320 to R 329 , R 330 to R 339 , R 340 to R 349 , R 350 to R 359 and R 360~R 369 Each independently is

[0106] a halogen atom,

[0107] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0108] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0109] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

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

[0111] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0112] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0113] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0114] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0115] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0116] a hydroxyl group,

[0117] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

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

[0119] an amino group,

[0120] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0121] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0122] a mercapto group,

[0123] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0124] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0125] * represents the bonding position of the benzene ring bonded to R 401 ~R 404 (The bonding position of the benzene ring bonded to R.)

[0126] (In the general formula (301),

[0127] R 31 ~R38 are each independently a hydrogen atom or a substituent,

[0128] R 401 ~R 412 are each independently a hydrogen atom or a substituent,

[0129] R as a substituent 31 ~R 38 and also R as a substituent 401 ~R 412 are each independently

[0130] a halogen atom,

[0131] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0132] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0133] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

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

[0135] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0136] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0137] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0138] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0139] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0140] a hydroxyl group,

[0141] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0142] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0143] an amino group,

[0144] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0145] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0146] a mercapto group,

[0147] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0148] A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0149] n is 0, 1, 2 or 3,

[0150] In the case where there are multiple Rs 405 the multiple Rs 405 are the same as or different from each other,

[0151] In the case where there are multiple Rs 406 the multiple Rs 406 are the same as or different from each other,

[0152] In the case where there are multiple Rs 407 the multiple Rs 407 are the same as or different from each other,

[0153] In the case where there are multiple Rs 408 the multiple Rs 408 are the same as or different from each other.)

[0154] According to one embodiment of the present invention, a compound represented by the following general formula (310) can be provided.

[0155]

Chemical Formula 9

[0156]

[0157] (In the general formula (310),

[0158] R 310 to R 319 are each independently a hydrogen atom or a substituent,

[0159] R 31 to R 38 are each independently a hydrogen atom or a substituent,

[0160] R 401 to R 412 are each independently a hydrogen atom or a substituent,

[0161] As substituents, R 310 to R 319 , as substituents, R 31 to R 38 and as substituents, R 401 to R 412 are each independently,

[0162] a halogen atom,

[0163] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0164] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0165] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0166] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0167] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0168] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0169] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0170] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0171] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0172] a hydroxyl group,

[0173] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0174] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0175] an amino group,

[0176] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0177] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0178] a mercapto group,

[0179] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0180] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0181] n is 0, 1, 2 or 3,

[0182] when there are multiple Rs 405 the multiple Rs 405 are the same as or different from each other,

[0183] when there are multiple Rs 406 the multiple Rs 406 are the same as or different from each other,

[0184] when there are multiple Rs 407 the multiple Rs 407 are the same as or different from each other,

[0185] when there are multiple Rs 408In the case of multiple Rs 408 are the same as or different from each other.)

[0186] According to one aspect of the present invention, there can be provided an organic electroluminescent element having an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer including a compound M2 having delayed fluorescence and a compound according to any one of the above aspects of the present invention.

[0187] According to one aspect of the present invention, there can be provided an electronic device equipped with an organic electroluminescent element according to any one of the above aspects of the present invention.

[0188] According to one aspect of the present invention, it is possible to provide a compound and an organic electroluminescent element with improved performance, particularly improved luminous efficiency, and an electronic device equipped with the organic electroluminescent element. BRIEF DESCRIPTION OF THE DRAWINGS

[0189] Figure 1 FIG. is a schematic configuration diagram showing an example of an organic electroluminescent element according to a first embodiment of the present invention.

[0190] Figure 2 FIG. is a schematic diagram of an apparatus for measuring transient PL.

[0191] Figure 3 FIG. is a diagram showing an example of an attenuation curve of transient PL.

[0192] Figure 4 FIG. is a diagram showing the relationship between the energy levels and energy transfer of compound M3 and compound M2 in the light-emitting layer of an example of an organic electroluminescent element according to a first embodiment of the present invention.

[0193] Figure 5 FIG. is a diagram showing the relationship between the energy levels and energy transfer of compound M3, compound M2, and compound M1 in the light-emitting layer of an example of an organic electroluminescent element according to a second embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0194] 〔First Embodiment〕

[0195] The configuration of the organic EL element according to the first embodiment of the present invention will be described.

[0196] The organic EL element has an organic layer between two electrodes, namely an anode and a cathode. This organic layer at least includes one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating multiple layers composed of organic compounds. The organic layer may also contain an inorganic compound. In the organic EL element of the present embodiment, at least one layer in the organic layer is a light-emitting layer. Therefore, for example, the organic layer can be composed of one light-emitting layer, or can include layers that can be used in the organic EL element. There is no particular limitation on the layers that can be used in the organic EL element. For example, at least any one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a blocking layer can be cited.

[0197] The organic EL element of the present embodiment has a light-emitting layer included between the anode and the cathode.

[0198] Figure 1 The schematic configuration of an example of the organic EL element in the present embodiment is shown.

[0199] The organic EL element 1 includes a light-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 formed by laminating a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.

[0200] In one aspect of the present embodiment, the light-emitting layer may also contain a metal complex.

[0201] Furthermore, in one aspect of the present embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material).

[0202] Furthermore, in one aspect of the present embodiment, the light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, as the heavy metal complex, for example, iridium complexes, osmium complexes, platinum complexes, etc. can be cited.

[0203] Furthermore, in one aspect of the present embodiment, the light-emitting layer preferably does not contain a metal complex.

[0204] In the organic EL element of the present embodiment, the light-emitting layer contains a delayed fluorescence compound M2 and a compound M3 represented by the following general formula (3).

[0205] In the case of this aspect, the compound M2 is preferably a dopant material (sometimes also referred to as a guest material, emitter, light-emitting material), and the compound M3 is preferably a host material (sometimes also referred to as a matrix material).

[0206] <Light-emitting layer>

[0207] (Compound M3)

[0208] The light-emitting layer of this embodiment contains a compound M3 represented by the following general formula (3).

[0209] The compound M3 of the present embodiment may be a compound that exhibits thermally activated delayed fluorescence or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0210]

Chemistry 10

[0211]

[0212] (In the general formula (3), A 30 is a group represented by the following general formula (3a), general formula (3b), general formula (3c), general formula (3d), general formula (3e) or general formula (3f).

[0213]

Chemistry 11

[0214]

[0215]

Chemistry 12

[0216]

[0217]

Chemistry 13

[0218]

[0219] (In the general formula (3a), general formula (3b), general formula (3c), general formula (3d), general formula (3e) and general formula (3f),

[0220] X 31 , X 32 , X 33 , X 34 , X 35 and X 36 are independently an oxygen atom, a sulfur atom, NR 371 or SiR 372 R 373 ,

[0221] R 371 , R 372 and R 373 are independently a hydrogen atom or a substituent,

[0222] R 310 ~R 319 are independently a hydrogen atom or a substituent, or R 310 and R 311 Group, R 311 and R 312 Group, R 312and R 313 group of, R 314 and R 315 group of, R 316 and R 317 group of, R 317 and R 318 group of, and also R 318 and R 319 Any one or more groups among the groups of form a ring by bonding to each other.

[0223] R 320 ~R 329 are each independently a hydrogen atom or a substituent, or R 320 and R 321 group of, R 321 and R 322 group of, R 322 and R 323 group of, R 324 and R 325 group of, R 326 and R 327 group of, R 327 and R 328 group of, and also R 328 and R 329 Any one or more groups among the groups of form a ring by bonding to each other.

[0224] R 330 ~R 339 are each independently a hydrogen atom or a substituent, or R 330 and R 331 group of, R 331 and R 332 group of, R 332 and R 333 group of, R 335 and R 336 group of, R 336 and R 337 group of, and also R 337 and R 338 Any one or more groups among the groups of form a ring by bonding to each other.

[0225] R 340 ~R 349 are each independently a hydrogen atom or a substituent, or R 340 and R 341 group of, R 341 and R 342 group of, R 342 and R 343 group of, R 345 and R 346 group of, R 346and R 347 groups of, and R 347 and R 348 any one or more groups among the groups of bond to each other to form a ring,

[0226] R 350 to R 359 are each independently a hydrogen atom or a substituent, or R 350 and R 351 groups of, R 351 and R 352 groups of, R 352 and R 353 groups of, R 354 and R 355 groups of, R 355 and R 356 groups of, R 356 and R 357 groups of, and R 358 and R 359 any one or more groups among the groups of bond to each other to form a ring,

[0227] R 360 to R 369 are each independently a hydrogen atom or a substituent, or R 360 and R 361 groups of, R 361 and R 362 groups of, R 362 and R 363 groups of, R 364 and R 365 groups of, R 365 and R 366 groups of, R 366 and R 367 groups of, and R 368 and R 369 any one or more groups among the groups of bond to each other to form a ring,

[0228] As the substituent R 371 , R 372 and R 373 , and as the substituent R 310 to R 319 , R 320 to R 329 , R 330 to R 339 , R 340 to R 349 , R 350 to R 359 and R 360 to R 369 are each independently,

[0229] a halogen atom,

[0230] a cyano group,

[0231] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0232] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0233] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0234] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0235] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0236] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0237] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0238] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0239] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0240] a hydroxyl group,

[0241] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0242] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0243] an amino group,

[0244] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[0245] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[0246] a mercapto group,

[0247] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0248] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0249] * represents the bonding position to L 30 .)

[0250] (In the general formula (3),

[0251] L 30 is,

[0252] A substituted or unsubstituted arylene group having 6 to 22 ring carbon atoms,

[0253] a group formed by bonding two substituted or unsubstituted arylene groups having 6 to 22 ring carbon atoms, or

[0254] a group formed by bonding three substituted or unsubstituted arylene groups having 6 to 22 ring carbon atoms,

[0255] R 31 ~R 38 are each independently a hydrogen atom or a substituent, or a group of R 31 and R 32 's group, R 32 and R 33 's group, R 33 and R 34 's group, R 35 and R 36 's group, R 36 and R 37 's group, and also a group of R 37 and R 38 's group, any one or more groups among them are bonded to each other to form a ring,

[0256] L 30 when having a substituent, the substituent and R as a substituent 31 ~R 38 are each independently

[0257] a halogen atom,

[0258] a cyano group,

[0259] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0260] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0261] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0262] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0263] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0264] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0265] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0266] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0267] Substituted or unsubstituted arylphosphoryl groups having 6 to 60 ring carbon atoms,

[0268] hydroxyl groups,

[0269] substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms,

[0270] substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms,

[0271] amino groups,

[0272] substituted or unsubstituted alkylamino groups having 2 to 30 carbon atoms,

[0273] substituted or unsubstituted arylamino groups having 6 to 60 ring carbon atoms,

[0274] mercapto groups,

[0275] substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or

[0276] substituted or unsubstituted arylthio groups having 6 to 30 ring carbon atoms.)

[0277] In compound M3, preferably A 30 is a group represented by the general formula (3a) or general formula (3d).

[0278] In compound M3, more preferably A 30 is a group represented by the general formula (3a). When A 30 is represented by the general formula (3a), compound M3 is represented by the following general formula (3A).

[0279]

Chemical formula 14

[0280]

[0281] R 31 ~R 38 , L 30 , X 31 , R 310 ~R 319 in the general formula (3A) are respectively synonymous with R 31 ~R 38 , L 30 , X 31 , R 310 ~R 319 in the general formula (3) or general formula (3a).

[0282] In compound M3, the groups of R 31 and R 32 , the groups of R 32 and R 33 are also preferred.33 and R 34 groups of, R 35 and R 36 groups of, R 36 and R 37 groups of, and also R 37 and R 38 groups of do not bond to each other. That is, in compound M3, it is also preferable that R 31 to R 38 are each independently a hydrogen atom or a substituent.

[0283] In compound M3, it is also preferable that R 31 and R 32 groups of, R 32 and R 33 groups of, R 33 and R 34 groups of, R 35 and R 36 groups of, R 36 and R 37 groups of, and also R 37 and R 38 at least one group among the groups of forms a ring by bonding to each other.

[0284] Compound M3 is also preferably represented by the following general formula (31), general formula (32), general formula (33), general formula (34), general formula (35), or general formula (36).

[0285]

Chemical formula 15

[0286]

[0287]

Chemical formula 16

[0288]

[0289]

Chemical formula 17

[0290]

[0291] (In the general formulas (31) to (36),

[0292] Y 31 、Y 32 、Y 33 、Y 34 、Y 35 and Y 36 are each independently an oxygen atom, a sulfur atom, NR 374 or SiR 375 R 376 ,

[0293] R 374 、R375 and R 376 are each independently a hydrogen atom or a substituent,

[0294] A 30 、L 30 、R 31 ~R 38 are respectively synonymous with A 30 、L 30 、R 31 ~R 38 in the general formula (3),

[0295] R 301 ~R 304 are each independently a hydrogen atom or a substituent, or a group of R 301 and R 302 、a group of R 302 and R 303 、or any one or more groups in a group of R 303 and R 304 are bonded to each other to form a ring,

[0296] R 301 ~R 304 、and R 374 、R 375 and R 376 are each independently,

[0297] a halogen atom,

[0298] a cyano group,

[0299] an aryl group having 6 to 30 ring carbon atoms which is substituted or unsubstituted,

[0300] a heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted,

[0301] an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted,

[0302] a haloalkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted,

[0303] an alkenyl group having 2 to 30 carbon atoms which is substituted or unsubstituted,

[0304] an alkynyl group having 2 to 30 carbon atoms which is substituted or unsubstituted,

[0305] an alkylsilyl group having 3 to 30 carbon atoms which is substituted or unsubstituted,

[0306] an arylsilyl group having 6 to 60 ring carbon atoms which is substituted or unsubstituted,

[0307] an arylphosphoryl group having 6 to 60 ring carbon atoms which is substituted or unsubstituted,

[0308] hydroxyl group

[0309] substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms

[0310] substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms

[0311] amino group

[0312] substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms

[0313] substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms

[0314] mercapto group

[0315] substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[0316] substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms.)

[0317] In compound M3, preferably, the groups of R 301 and R 302 , the groups of R 302 and R 303 , and the groups of R 303 and R 304 do not bond to each other.

[0318] In compound M3, preferably, R 301 to R 304 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0319] In compound M3, more preferably, R 301 to R 304 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.

[0320] In compound M3, further preferably, R 301 to R 304 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

[0321] In compound M3, even more preferably, R 301 to R 304 are hydrogen atoms.

[0322] In compound M3, preferably, Y 31 , Y32 and Y 33 and Y 34 and Y 35 and Y 36 are each independently an oxygen atom or a sulfur atom.

[0323] In compound M3, preferably, R 31 to R 38 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0324] In compound M3, more preferably, R 31 to R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0325] In compound M3, further preferably, R 31 to R 38 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0326] In compound M3, even more preferably, R 31 to R 38 is a hydrogen atom.

[0327] In compound M3, preferably, R 31 to R 38 and also R 301 to R 304 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0328] In compound M3, more preferably, R 31 to R 38 and also R 301 to R 304 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0329] In compound M3, further preferably, R 31 to R 38 and also R 301 to R 304 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0330] In compound M3, R is more preferably 31 ~R 38 and R 301 ~R 304 is a hydrogen atom.

[0331] In compound M3, L is preferably 30 a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0332] In compound M3, L is more preferably 30 a substituted or unsubstituted biphenylene group.

[0333] In compound M3, when L 30 has a substituent, the substituent (sometimes referred to as substituent F L ) is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0334] In compound M3, L is also preferably 30 at least one group selected from the group consisting of the groups represented by the following general formulas (L30-1) to (L30-4), (L30-4-2), (L30-5) to (L30-11).

[0335]

Chemical formula 18

[0336]

[0337]

Chemical formula 19

[0338]

[0339] In the general formulas (L30-1) to (L30-4), (L30-4-2), (L30-5) to (L30-11), Q1 to Q 14 are each independently a hydrogen atom or a substituent, and Q1 to Q as substituents 14 are each independently

[0340] a halogen atom,

[0341] a cyano group,

[0342] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0343] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0344] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0345] A substituted or unsubstituted haloalkyl having 1 to 30 carbon atoms,

[0346] A substituted or unsubstituted alkenyl having 2 to 30 carbon atoms,

[0347] A substituted or unsubstituted alkynyl having 2 to 30 carbon atoms,

[0348] A substituted or unsubstituted alkylsilyl having 3 to 30 carbon atoms,

[0349] A substituted or unsubstituted arylsilyl having 6 to 60 ring carbon atoms,

[0350] A substituted or unsubstituted arylphosphoryl having 6 to 60 ring carbon atoms,

[0351] Hydroxy,

[0352] A substituted or unsubstituted alkoxy having 1 to 30 carbon atoms,

[0353] A substituted or unsubstituted aryloxy having 6 to 30 ring carbon atoms,

[0354] Amino,

[0355] A substituted or unsubstituted alkylamino having 2 to 30 carbon atoms,

[0356] A substituted or unsubstituted arylamino having 6 to 60 ring carbon atoms,

[0357] Mercapto,

[0358] A substituted or unsubstituted alkylthio having 1 to 30 carbon atoms, or

[0359] A substituted or unsubstituted arylthio having 6 to 30 ring carbon atoms.

[0360] Preferably, Q1 to Q as substituents 14 are each independently a hydrogen atom, a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl having 1 to 30 carbon atoms.

[0361] In compound M3, it is also preferred that X 31 , X 32 , X 33 , X 34 , X 35 and X 36 are each independently an oxygen atom, NR 301 or SiR 302 R 303 .

[0362] In compound M3, it is also preferred that X 31 , X 32 , X 33 , X34 , X 35 and X 36 are each independently an oxygen atom or a sulfur atom.

[0363] In compound M3, it is also preferred that X 31 , X 32 , X 33 , X 34 , X 35 and X 36 is an oxygen atom.

[0364] In compound M3, when X 31 is an oxygen atom, for example, the general formula (3a) is represented by the following general formula (3a-1), and when X 31 is a sulfur atom, for example, the general formula (3a) is represented by the following general formula (3a-2), and when X 31 is NR 371 , for example, the general formula (3a) is represented by the following general formula (3a-3), and when X 31 is SiR 372 R 373 , for example, the general formula (3a) is represented by the following general formula (3a-4).

[0365]

Chemical formula 20

[0366]

[0367]

Chemical formula 21

[0368]

[0369] In compound M3, it is preferred that

[0370] the group of R 310 and R 311 , the group of R 311 and R 312 , the group of R 312 and R 313 , the group of R 314 and R 315 , the group of R 316 and R 317 , the group of R 317 and R 318 , and also the group of R 318 and R 319 do not bond to each other,

[0371] the group of R 320 and R 321 , the group of R 321 and R 322 , the group of R 322 and R323 groups of, R 324 and R 325 groups of, R 326 and R 327 groups of, R 327 and R 328 groups of, and also R 328 and R 329 The groups of do not bond to each other,

[0372] R 330 and R 331 groups of, R 331 and R 332 groups of, R 332 and R 333 groups of, R 335 and R 336 groups of, R 336 and R 337 groups of, and also R 337 and R 338 The groups of do not bond to each other,

[0373] R 340 and R 341 groups of, R 341 and R 342 groups of, R 342 and R 343 groups of, R 345 and R 346 groups of, R 346 and R 347 groups of, and also R 347 and R 348 The groups of do not bond to each other,

[0374] R 350 and R 351 groups of, R 351 and R 352 groups of, R 352 and R 353 groups of, R 354 and R 355 groups of, R 355 and R 356 groups of, R 356 and R 357 groups of, and also R 358 and R 359 The groups of do not bond to each other,

[0375] R 360 and R 361 groups of, R 361 and R 362 groups of, R 362 and R 363group of, R 364 and R 365 group of, R 365 and R 366 group of, R 366 and R 367 group of, and also R 368 and R 369 The groups do not bond to each other.

[0376] In compound M3, preferably R 310 ~R 319 , R 320 ~R 329 , R 330 ~R 339 , R 340 ~R 349 , R 350 ~R 359 , R 360 ~R 369 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0377] In compound M3, more preferably R 310 ~R 319 , R 320 ~R 329 , R 330 ~R 339 , R 340 ~R 349 , R 350 ~R 359 , R 360 ~R 369 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0378] In compound M3, further preferably R 310 ~R 319 , R 320 ~R 329 , R 330 ~R 339 , R 340 ~R 349 , R 350 ~R 359 , R 360 ~R 369 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0379] In compound M3, even more preferably R310 ~R 319 、R 320 ~R 329 、R 330 ~R 339 、R 340 ~R 349 、R 350 ~R 359 and R 360 ~R 369 is a hydrogen atom.

[0380] · Method for manufacturing compound M3 of the present embodiment

[0381] The compound M3 of the present embodiment can be manufactured, for example, by the method described in the examples below. The compound M3 of the present embodiment can be manufactured by imitating the reactions described in the examples below and using known alternative reactions and raw materials that match the target product.

[0382] · Specific examples of compound M3

[0383] As specific examples of the compound M3 of the present embodiment, the following compounds can be cited, for example. However, the present invention is not limited to these specific examples of the compounds.

[0384]

Chemical formula 22

[0385]

[0386]

Chemical formula 23

[0387]

[0388]

Chemical formula 24

[0389]

[0390]

Chemical formula 25

[0391]

[0392]

Chemical formula 26

[0393]

[0394]

Chemical formula 27

[0395]

[0396]

Chemical formula 28

[0397]

[0398]

Chemical formula 29

[0399]

[0400]

Chemical 30

[0401]

[0402]

Chemical 31

[0403]

[0404]

Chemical 32

[0405]

[0406]

Chemical 33

[0407]

[0408]

Chemical 34

[0409]

[0410]

Chemical 35

[0411]

[0412]

Chemical 36

[0413]

[0414]

Chemical 37

[0415]

[0416]

Chemical 38

[0417]

[0418]

Chemical 39

[0419]

[0420]

Chemical 40

[0421]

[0422]

Chemical 41

[0423]

[0424]

Chemical 42

[0425]

[0426]

Chemical 43

[0427]

[0428]

Chemical 44

[0429]

[0430]

Chemical 45

[0431]

[0432]

Chemical 46

[0433]

[0434]

Chemical 47

[0435]

[0436]

Chemical 48

[0437]

[0438]

Chemical 49

[0439]

[0440]

Chemical 50

[0441]

[0442]

Chemical 51

[0443]

[0444]

Chemical 52

[0445]

[0446]

Chemical 53

[0447]

[0448]

Chemical 54

[0449]

[0450]

Chemical 55

[0451]

[0452]

Chemical 56

[0453]

[0454]

Chemical 57

[0455]

[0456]

Chemical 58

[0457]

[0458]

Chemical 59

[0459]

[0460]

Chemical 60

[0461]

[0462]

Chemical 61

[0463]

[0464]

Chemical 62

[0465]

[0466]

Chemical 63

[0467]

[0468]

Chemical 64

[0469]

[0470]

Chemical 65

[0471]

[0472]

Chemical 66

[0473]

[0474]

Chemical 67

[0475]

[0476]

Chemical 68

[0477]

[0478]

Chemical 69

[0479]

[0480]

Chemical 70

[0481]

[0482]

Chemical 71

[0483]

[0484]

Chemical 72

[0485]

[0486]

Chemical Formula 73

[0487]

[0488]

Chemical Formula 74

[0489]

[0490]

Chemical Formula 75

[0491]

[0492]

Chemical Formula 76

[0493]

[0494]

Chemical Formula 77

[0495]

[0496]

Chemical Formula 78

[0497]

[0498]

Chemical Formula 79

[0499]

[0500]

Chemical Formula 80

[0501]

[0502]

Chemical Formula 81

[0503]

[0504]

Chemical Formula 82

[0505]

[0506]

Chemical Formula 83

[0507]

[0508]

Chemical Formula 84

[0509]

[0510]

Chemical Formula 85

[0511]

[0512]

Chemical Formula 86

[0513]

[0514]

Chemical 87

[0515]

[0516]

Chemical 88

[0517]

[0518]

Chemical 89

[0519]

[0520]

Chemical 90

[0521]

[0522]

Chemical 91

[0523]

[0524]

Chemical 92

[0525]

[0526]

Chemical 93

[0527]

[0528]

Chemical 94

[0529]

[0530]

Chemical 95

[0531]

[0532]

Chemical 96

[0533]

[0534]

Chemical 97

[0535]

[0536]

Chemical 98

[0537]

[0538]

Chemical 99

[0539]

[0540]

Chemical 100

[0541]

[0542]

Chemical 101

[0543]

[0544]

Chemical 102

[0545]

[0546]

Chemical 103

[0547]

[0548]

Chemical 104

[0549]

[0550]

Chemical 105

[0551]

[0552]

Chemical 106

[0553]

[0554]

Chemical 107

[0555]

[0556]

Chemical 108

[0557]

[0558]

Chemical 109

[0559]

[0560]

Chemical 110

[0561]

[0562]

Chemical 111

[0563]

[0564]

Chemical 112

[0565]

[0566]

Chemical 113

[0567]

[0568]

Chemical 114

[0569]

[0570] [Chemical Formula 115]

[0571]

[0572] [Chemical Formula 116]

[0573]

[0574] [Chemical Formula 117]

[0575]

[0576] [Chemical Formula 118]

[0577]

[0578] [Chemical Formula 119]

[0579]

[0580] (Compound M2)

[0581] The light-emitting layer of this embodiment contains a compound M2 with delayed fluorescence properties.

[0582] ·Delayed fluorescence properties

[0583] Regarding delayed fluorescence, it is explained on pages 261 - 268 of "Device Physical Properties of Organic Semiconductors" (edited by Chiba Yaya, published by Kodansha). In this document, it is stated that if the energy difference △E between the excited singlet state and the excited triplet state of a fluorescent material can be reduced 13 , then reverse energy transfer from the excited triplet state with low migration probability to the excited singlet state occurs efficiently, generating thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is illustrated in Figure 10.38 of this document. The compound M2 in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0584] Generally, the emission of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0585] It is also possible to analyze the behavior of delayed fluorescence based on the decay curve obtained from transient PL measurement. Transient PL measurement is a method of irradiating a sample with pulsed laser light to excite it and measuring the decay behavior (transient characteristics) of the PL emission after the irradiation is stopped. The PL emission 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 light is irradiated.

[0586] On the other hand, delayed fluorescence is the luminescence from singlet excitons generated via long-lived triplet excitons, so it decays smoothly. 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.

[0587] Figure 2 The schematic diagram of an example device for measuring transient PL is shown.

[0588] An example of the measurement method of transient PL using Figure 2 and the analysis of the behavior of delayed fluorescence will be described.

[0589] Figure 2 The transient PL measurement device 100 of Figure 2 includes: a pulsed laser unit 101 that can irradiate light of a specified wavelength; a sample chamber 102 that houses the measurement sample; a spectroscope 103 that spectroscopically analyzes 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

[0590] The sample housed in the sample chamber 102 can be obtained by forming a film of a thin film doped with a dopant material at a concentration of 12 mass% with respect to a matrix material on a quartz substrate.

[0591] For the thin film sample housed in the sample chamber 102, pulsed laser light is irradiated from the pulsed laser unit 101 to excite the dopant material. The 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 imaged 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.

[0592] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the doping material, a thin film sample A was fabricated as described above, and transient PL measurement was performed.

[0593] [Chemical Formula 120]

[0594]

[0595] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. For thin film sample B, the following reference compound H2 was used as the matrix material, and the aforementioned reference compound D1 was used as the doping material, and the thin film sample was fabricated as described above.

[0596] Figure 3 The decay curves obtained from the transient PL measurements of thin film sample A and thin film sample B are shown.

[0597] [Chemical Formula 121]

[0598]

[0599] As described above, through transient PL measurement, a luminescence decay curve with the luminescence intensity on the vertical axis and time on the horizontal axis can be obtained. Based on this luminescence decay curve, the fluorescence intensity ratio between 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 delayed fluorescence material, the proportion of the intensity of the slowly decaying delayed fluorescence is relatively large compared to the intensity of the rapidly decaying fluorescence.

[0600] Specifically, as the luminescence from a delayed fluorescence material, there are Prompt luminescence (instantaneous luminescence) and Delay luminescence (delayed luminescence). Prompt luminescence (instantaneous luminescence) refers to the luminescence immediately observed from the excited state after excitation by pulsed light (light irradiated from a pulsed laser) with a wavelength absorbed by the delayed fluorescence material. Delay luminescence (delayed luminescence) refers to the luminescence that cannot be immediately observed after excitation by the pulsed light but is observed later.

[0601] The amounts and ratio of Prompt luminescence and Delay luminescence 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 aforementioned Reference 1 or Figure 2 the device described therein.

[0602] In addition, in the present embodiment, a specimen prepared by the method shown below is used in the measurement of the delayed fluorescence property of Compound M2. For example, Compound M2 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 specimen solution is frozen and degassed, it is sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free specimen solution saturated with argon.

[0603] The fluorescence spectrum of the above specimen solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and 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.

[0604] The amounts of prompt luminescence and delay luminescence and their ratio can be determined by the same method as 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 in

[0605] In the present embodiment, the amount of prompt luminescence (instantaneous luminescence) of the compound to be measured (Compound M2) is denoted as X P and the amount of delay luminescence (delayed luminescence) is denoted as X D When D / X P the value of is preferably 0.05 or more.

[0606] The measurement of the amounts of prompt luminescence and delay luminescence and their ratio for compounds other than Compound M2 in this specification is the same as the measurement of the amounts of prompt luminescence and delay luminescence and their ratio for Compound M2.

[0607] As Compound M2, for example, a compound represented by the following general formula (2) can be exemplified.

[0608]

Chemical Formula 122

[0609]

[0610] In the general formula (2),

[0611] n is 1, 2, 3 or 4,

[0612] m is 1, 2, 3 or 4,

[0613] q is 0, 1, 2, 3 or 4,

[0614] m + n + q = 6,

[0615] CN is a cyano group,

[0616] The D1 is a group represented by the following general formula (2a), the following general formula (2b) or the following general formula (2c). When there are multiple D1s, the multiple D1s are the same as or different from each other.

[0617] Rx is a hydrogen atom or a substituent, or adjacent Rx groups bond to each other to form a ring. When there are multiple Rx groups, the multiple Rx groups are the same as or different from each other.

[0618] Rx as a substituent is independently respectively

[0619] a halogen atom,

[0620] an aryl group with 6 to 30 ring carbon atoms which is substituted or unsubstituted,

[0621] a heterocyclic group with 5 to 30 ring atoms which is substituted or unsubstituted,

[0622] an amino group which is substituted or unsubstituted,

[0623] a carbonyl group which is substituted or unsubstituted,

[0624] an alkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted,

[0625] a haloalkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted,

[0626] an alkylsilyl group with 3 to 30 carbon atoms which is substituted or unsubstituted, or

[0627] an arylsilyl group with 6 to 60 ring carbon atoms which is substituted or unsubstituted,

[0628] CN, D1 and Rx are respectively bonded to the carbon atoms of the six - membered ring.

[0629]

Chemical formula 123

[0630]

[0631] In the general formula (2a), R1 to R8 are independently respectively a hydrogen atom or a substituent, or any one or more of the groups of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, and R7 and R8 bond to each other to form a ring.

[0632] R1 to R8 as substituents are independently respectively

[0633] a halogen atom,

[0634] an aryl group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted,

[0635] a heterocyclic group having 5 to 30 ring atoms, which may be substituted or unsubstituted,

[0636] an alkyl group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0637] a haloalkyl group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0638] an alkylsilyl group having 3 to 30 carbon atoms, which may be substituted or unsubstituted,

[0639] an arylsilyl group having 6 to 60 ring carbon atoms, which may be substituted or unsubstituted,

[0640] a hydroxyl group,

[0641] an alkoxy group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0642] a haloalkoxy group having 1 to 30 carbon atoms, which may be substituted or unsubstituted,

[0643] an aryloxy group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted,

[0644] an alkylamino group having 2 to 30 carbon atoms, which may be substituted or unsubstituted,

[0645] an arylamino group having 6 to 60 ring carbon atoms, which may be substituted or unsubstituted,

[0646] a mercapto group,

[0647] an alkylthio group having 1 to 30 carbon atoms, which may be substituted or unsubstituted, or

[0648] an arylthio group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted.

[0649] * indicates the bonding position to the carbon atom of the benzene ring in the general formula (2).

[0650]

Chemical Formula 124

[0651]

[0652] In the general formula (2b),

[0653] R 21 ~R 28 are each independently a hydrogen atom or a substituent, or a group of R 21 and R 22 , a group of R 22 and R 23 , a group of R 23 and R24 group, R 25 and R 26 group, R 26 and R 27 group, and also R 27 and R 28 Any one or more of the groups in the group bond to each other to form a ring.

[0654] R as a substituent 21 ~R 28 are each independently synonymous with R1 to R8 as substituents in the general formula (2a).

[0655] A represents a ring structure represented by the following general formula (211) or the following general formula (212), and this ring structure A is fused to an adjacent ring structure at an arbitrary position.

[0656] p is 1, 2, 3 or 4.

[0657] When p is 2, 3 or 4, the plurality of ring structures A are the same as or different from each other.

[0658] * represents the bonding site to the carbon atom of the benzene ring in the general formula (2).

[0659]

Chemical Formula 125

[0660]

[0661] In the general formula (2c),

[0662] R 2001 ~R 2008 are each independently a hydrogen atom or a substituent, or R 2001 and R 2002 group, R 2002 and R 2003 group, R 2003 and R 2004 group, R 2005 and R 2006 group, R 2006 and R 2007 group, and also R 2007 and R 2008 Any one or more of the groups in the group bond to each other to form a ring.

[0663] R as a substituent 2001 ~R 2008 are each independently synonymous with R1 to R8 as substituents in the general formula (2a).

[0664] B represents a ring structure represented by the following general formula (211) or the following general formula (212), and this ring structure B is fused to an adjacent ring structure at any position.

[0665] px is 1, 2, 3, or 4.

[0666] When px is 2, 3, or 4, the multiple ring structures B are the same as or different from each other.

[0667] C represents a ring structure represented by the following general formula (211) or the following general formula (212), and this ring structure C is fused to an adjacent ring structure at any position.

[0668] py is 1, 2, 3, or 4.

[0669] When py is 2, 3, or 4, the multiple ring structures C are the same as or different from each other.

[0670] * represents the bonding site to the carbon atom of the benzene ring in the general formula (2).

[0671]

Chemical Formula 126

[0672]

[0673] In the general formula (211), R 2009 and R 2010 are each independently a hydrogen atom or a substituent, or bond to each other to form a ring with a part of an adjacent ring structure, or the group of R 2009 and R 2010 bond to each other to form a ring.

[0674] In the general formula (212), X 201 is CR 2011 R 2012 , NR 2013 , a sulfur atom, or an oxygen atom, and R 2011 , R 2012 and R 2013 are each independently a hydrogen atom or a substituent, or R 2011 and R 2012 bond to each other to form a ring.

[0675] As substituents, R 2009 , R 2010 , R 2011 , R 2012 and R 2013 are each independently synonymous with R1 to R8 as substituents in the general formula (2a).

[0676] In the general formula (211), R 2009 and R 2010Independently bond to a part of an adjacent ring structure to form a ring, specifically referring to any one of the following (I) to (IV).

[0677] In addition, in the general formula (211), R 2009 and R 2010 bond to each other to form a ring, specifically referring to the following (V).

[0678] (I) When the ring structures represented by the general formula (211) are adjacent to each other, one of the R 2009 in one of the two adjacent rings and the R 2009 in the other ring, one of the R 2009 in one ring and the R 2010 in the other ring, and also one of the R 2010 in one ring and the R 2010 in the other ring, any one or more of these groups bond to each other to form a ring.

[0679] (II) When the ring structure represented by the general formula (211) is adjacent to the benzene ring having R 25 to R 28 in the general formula (2b), one of the R 2009 in one of the two adjacent rings and the R 25 in the other ring, one of the R 2009 in one ring and the R 28 in the other ring, one of the R 2010 in one ring and the R 25 in the other ring, and also one of the R 2010 in one ring and the R 28 in the other ring, any one or more of these groups bond to each other to form a ring.

[0680] (III) When the ring structure represented by the general formula (211) is adjacent to the benzene ring having R 2001 to R 2004 in the general formula (2c), one of the R 2009 in one of the two adjacent rings and the R 2001 in the other ring, one of the R 2009 in one ring and the R 2004 in the other ring, one of the R 2010 in one ring and the R 2001 in the other ring, and also one of the R 2010 in one ring and the R 2004 in the other ring, any one or more of these groups bond to each other to form a ring.

[0681] (IV) When the ring structure represented by the general formula (211) is adjacent to the benzene ring having R 2005 to R2008 When adjacent to the benzene ring, R of one of the two adjacent rings 2009 and R of the other ring 2005 of the group, R of one ring 2009 and R of the other ring 2008 of the group, R of one ring 2010 and R of the other ring 2005 of the group, and also R of one ring 2010 and R of the other ring 2008 of the group, any one or more of the groups bond to each other to form a ring.

[0682] (V) R of the ring structure represented by the general formula (211) 2009 and R 2010 of the group bond to each other to form a ring. That is, (V) means R 2009 and R 2010 of the group that bond to the same ring bond to each other to form a ring.

[0683] In the compound M2 of the present embodiment, preferably, each Rx is independently

[0684] a hydrogen atom,

[0685] an unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0686] an unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0687] an unsubstituted alkyl group having 1 to 30 carbon atoms.

[0688] When Rx is an unsubstituted heterocyclic group having 5 to 30 ring atoms, Rx as the unsubstituted heterocyclic group having 5 to 30 ring atoms is a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

[0689] In the present specification, the triazinyl group means a group obtained by removing one hydrogen atom from 1,3,5-triazine, 1,2,4-triazine or 1,2,3-triazine.

[0690] The triazinyl group is preferably a group obtained by removing one hydrogen atom from 1,3,5-triazine.

[0691] In the compound M2 of the present embodiment, more preferably, each Rx is independently

[0692] a hydrogen atom,

[0693] an unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0694] an unsubstituted dibenzofuranyl group, or

[0695] Unsubstituted dibenzothienyl.

[0696] In the compound M2 of the present embodiment, it is more preferred that Rx is a hydrogen atom.

[0697] In the compound M2 of this embodiment, it is preferred that R1 to R8, R 21 ~R 28 , R 2001 ~R 2008 , R 2009 ~R 2010 and R 2011 ~R 2013 Independently,

[0698] unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0699] an unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0700] An unsubstituted alkyl group having 1 to 30 carbon atoms.

[0701] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by the following general formula (D-21), (D-22), (D-23) or (D-24).

[0702]

Chemistry 127

[0703]

[0704]

Chemistry 128

[0705]

[0706] In the general formulas (D-21) to (D-24), R 171 ~R 200 and R 71 ~R 82 are independently a hydrogen atom or a substituent, or R 171 and R 172 Group, R 172 and R 173 Group, R 173 and R 174 Group, R 174 and R 175 Group, R 175 and R 176 Group, R 177 and R 178 Group, R 178 and R 179 Group, R 179 and R 180 Group, R181 and R 182 group of, R 182 and R 183 group of, R 183 and R 184 group of, R 185 and R 186 group of, R 186 and R 187 group of, R 187 and R 188 group of, R 188 and R 189 group of, R 189 and R 190 group of, R 191 and R 192 group of, R 192 and R 193 group of, R 193 and R 194 group of, R 194 and R 195 group of, R 195 and R 196 group of, R 197 and R 198 group of, R 198 and R 199 group of, R 199 and R 200 group of, R 71 and R 72 group of, R 72 and R 73 group of, R 73 and R 74 group of, R 75 and R 76 group of, R 76 and R 77 group of, R 77 and R 78 group of, R 79 and R 80 group of, R 80 and R 81 group of, and also R 81 and R 82 Any one or more groups among the groups of are bonded to each other to form a ring.

[0707] R as a substituent 171 ~R 200 and R 71 ~R 82 are each independently

[0708] a halogen atom

[0709] Aryl having 6 to 14 ring carbon atoms, which may or may not be substituted,

[0710] Heterocyclic group having 5 to 14 ring atoms, which may or may not be substituted,

[0711] Alkyl having 1 to 6 carbon atoms, which may or may not be substituted,

[0712] Halogenated alkyl having 1 to 30 carbon atoms, which may or may not be substituted,

[0713] Alkylsilyl having 3 to 6 carbon atoms, which may or may not be substituted,

[0714] Hydroxyl group,

[0715] Alkoxy group having 1 to 6 carbon atoms, which may or may not be substituted,

[0716] Halogenated alkoxy group having 1 to 6 carbon atoms, which may or may not be substituted,

[0717] Aryloxy group having 6 to 14 ring carbon atoms, which may or may not be substituted,

[0718] Alkylamino group having 2 to 12 carbon atoms, which may or may not be substituted,

[0719] Mercapto group,

[0720] Alkylthio group having 1 to 6 carbon atoms, which may or may not be substituted, or

[0721] Arylthio group having 6 to 14 ring carbon atoms, which may or may not be substituted.

[0722] * indicates the bonding site to the carbon atom of the benzene ring in the general formula (2).

[0723] In the compound M2 of the present embodiment, it is more preferably that the D1 is a group represented by the general formula (D-21), (D-23) or (D-24).

[0724] In the compound M2 of the present embodiment, it is further preferably that the D1 is a group represented by the general formula (D-21) or (D-23).

[0725] In the compound M2 of the present embodiment, preferably, as substituents, R 171 ~R 200 and R 71 ~R 82 are each independently

[0726] Aryl having 6 to 14 ring carbon atoms, which is not substituted,

[0727] Heterocyclic group having 5 to 14 ring atoms, which is not substituted, or

[0728] Alkyl having 1 to 6 carbon atoms, which is not substituted.

[0729] In the compound M2 of the present embodiment, R is also preferably 171 ~R 200 and R 71 ~R 82 are hydrogen atoms.

[0730] As the compound M2, for example, a compound represented by the following general formula (22) can be cited.

[0731]

Chemical Formula 129

[0732]

[0733] In the general formula (22), Ar1 is any group selected from the group consisting of 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 fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxyl group, and groups represented by the following general formulas (1a) to (1j).

[0734] In the general formula (22), Ar EWG is a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms containing one or more nitrogen atoms in the ring, or a substituted aryl group having 6 to 30 ring carbon atoms substituted with one or more cyano groups.

[0735] In the general formula (22), Ar X are each independently a hydrogen atom or a substituent. As the substituent Ar X is any group selected from the group consisting of 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 fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxyl group, and groups represented by the following general formulas (1a) to (1j).

[0736] In the general formula (22), n is 0, 1, 2, 3, 4 or 5. When n is 2, 3, 4 or 5, the plurality of Ar X are the same as or different from each other.

[0737] In the general formula (22), ring (A) is a five-membered ring, a six-membered ring or a seven-membered ring. Ring (A) can be an aromatic hydrocarbon ring or a heterocyclic ring. Ar1 and Ar XBonded to the elements constituting the ring (A), respectively.

[0738] In the general formula (22), at least any one of Ar1 and Ar X is any group selected from the group consisting of the groups represented by the following general formulas (1a) to (1j).

[0739]

Chemical formula 130

[0740]

[0741]

Chemical formula 131

[0742]

[0743]

Chemical formula 132

[0744]

[0745]

Chemical formula 133

[0746]

[0747]

Chemical formula 134

[0748]

[0749]

Chemical formula 135

[0750]

[0751]

Chemical formula 136

[0752]

[0753] In the general formulas (1a) to (1j), X1 to X 20 are each independently a nitrogen atom (N) or a carbon atom bonded to R A1 (C-R A1 ).

[0754] In the general formula (1b), any one of X5 to X8 is a carbon atom bonded to any one of X9 to X 12 , and any one of X9 to X 12 is a carbon atom bonded to any one of X5 to X8.

[0755] In the general formula (1c), any one of X5 to X8 is a carbon atom bonded to the nitrogen atom in the ring containing A2.

[0756] In the general formula (1e), any one of X5 to X8 and X 18 is a carbon atom bonded to any one of X9 to X 12 , and any one of X9 to X12 Any one of them is a carbon atom bonded to X5 to X8 and X 18 Any one of the keys.

[0757] In the general formula (1f), any one of X5 to X8 and X 18 Any one of them is bonded to X9 to X 12 And X 19 Any one of them is a carbon atom bonded to any one of X9 to X 12 And X 19 Any one of them is bonded to any one of X5 to X8 and X 18 Any one of the keys.

[0758] In the general formula (1g), any one of X5 to X8 is bonded to X9 to X 12 And X 19 Any one of them is a carbon atom bonded to any one of X9 to X 12 And X 19 Any one of them is a carbon atom bonded to any one of X5 to X8.

[0759] In the general formula (1h), any one of X5 to X8 and X 18 Any one of them is a carbon atom bonded to a nitrogen atom in the ring containing A2.

[0760] In the general formula (1i), any one of X5 to X8 and X 18 Any one of them is bonded to the nitrogen atom that connects the ring containing X9 to X 12 And X 19 The ring of is connected to the ring containing X 13 ~X 16 And X 20 Any one of the rings of and X

[0761] In the general formula (1j), any one of X5 to X8 is bonded to the nitrogen atom that connects the ring containing X9 to X 12 And X 19 The ring of is connected to the ring containing X 13 ~X 16 And X 20 Any one of the rings of and X

[0762] R A1 Are each independently a hydrogen atom or a substituent, or any one or more groups in the group formed by a plurality of R A1 Bond to each other directly to form a ring or form a ring via a heteroatom,

[0763] R as a substituent A1It is any group selected from the group consisting of a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxyl group.

[0764] A plurality of Rs as substituents A1 are the same as or different from each other.

[0765] In the general formula (1a), X1 to X8 are carbon atoms (C-R A1 ) bonded to R. When this is the case, it is preferable that a plurality of Rs A1 do not form a ring. A1

[0766] In the general formulas (1a) to (1j), * represents the bonding site to the ring (A).

[0767] In the general formulas (1a) to (1j), A1 and A2 are each independently a single bond, an oxygen atom (O), a sulfur atom (S), C(R 2021 )(R 2022 ), Si(R 2023 )(R 2024 ), C(=O), S(=O), SO2, or N(R 2025 ). Rs 2021 to R 2025 are each independently a hydrogen atom or a substituent. As substituents, Rs 2021 to R 2025 are each independently any group selected from the group consisting of a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxyl group.

[0768] ​In the general formulas (1a) to (1j), Ara is any group selected from the group consisting of 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 fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, and a substituted silyl group. Ara 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.

[0769] When A1 is a single bond in the general formula (1a), it is represented by the following general formula (1aa). When A1 is O, it is represented by the following general formula (1ab). When A1 is S, it is represented by the following general formula (1ac). When A1 is C(R 2021 )(R 2022 ), it is represented by the following general formula (1ad). When A1 is Si(R 2023 )(R 2024 ), it is represented by the following general formula (1ae). When A1 is C(=O), it is represented by the following general formula (1af). When A1 is S(=O), it is represented by the following general formula (1ag). When A1 is SO2, it is represented by the following general formula (1ah). When A1 is N(R 2025 ), it is represented by the following general formula (1ai). In the following general formulas (1aa) to (1ai), X1 to X8 and R 2021 to R 2025 have the same meanings as above. For the general formulas (1b), (1c), (1e), (1g) to (1j), the connection mode of the rings of A1 and A2 to each other is also the same as that of the following general formulas (1aa) to (1ai). In the following general formula (1aa), when X1 to X8 are carbon atoms (C-R A1 ) bonded to R A1 , it is preferred that a plurality of R A1 as substituents do not form a ring.

[0770]

Chemical formula 137

[0771]

[0772]

Chemical formula 138

[0773]

[0774]

Chemical formula 139

[0775]

[0776] Compound M2 is preferably represented by the following general formula (221).

[0777]

Chemical 140

[0778]

[0779] Ar1, Ar in the general formula (221) EWG , Ar x , n and ring (A) are synonymous with Ar1, Ar in the general formula (22) EWG , Ar x , n and ring (A), respectively.

[0780] Compound M2 is also preferably represented by the following general formula (222).

[0781]

Chemical 141

[0782]

[0783] In the general formula (222), Y1 to Y5 are each independently a nitrogen atom (N), a carbon atom bonded to a cyano group (C-CN), or a carbon atom bonded to R A2 (C-R A2 ), and at least one of Y1 to Y5 is N or C-CN. A plurality of R A2 are the same or different from each other. R A2 are each independently a hydrogen atom or a substituent, and R A2 as a substituent is a group selected from the group consisting of a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxyl group.

[0784] A plurality of R A2 are the same or different from each other.

[0785] In the general formula (222), Ar1 is synonymous with Ar1 in the general formula (22).

[0786] In the general formula (222), Ar2 to Ar5 are each independently a hydrogen atom or a substituent. As the substituent, Ar2 to Ar5 are each independently selected from the group consisting of 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 fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxyl group, and a group represented by the general formula (1a) to (1c).

[0787] In the general formula (222), at least one of Ar1 to Ar5 is an arbitrary group selected from the group consisting of the groups represented by the general formula (1a) to (1c).

[0788] Compound M2 is also preferably a compound represented by the following general formula (11aa), the following general formula (11bb), or the following general formula (11cc).

[0789]

Chemical Formula 142

[0790]

[0791]

Chemical Formula 143

[0792]

[0793] In the general formulas (11aa), (11bb), and (11cc), Y1 to Y5, R A2 , Ar2 to Ar5, X1 to X 16 , R A1 and Ara respectively represent the same meanings as Y1 to Y5, R A2 , Ar2 to Ar5, X1 to X 16 , R A1 and Ara described above.

[0794] As compound M2, for example, a compound represented by the following general formula (23) can be cited.

[0795]

Chemical Formula 144

[0796]

[0797] In the general formula (23),

[0798] Az is selected from

[0799] a substituted or unsubstituted pyridine ring,

[0800] a substituted or unsubstituted pyrimidine ring,

[0801] A triazine ring which may or may not be substituted, and

[0802] a pyrazine ring which may or may not be substituted

[0803] a ring structure selected from the group consisting of

[0804] c is 0, 1, 2, 3, 4 or 5,

[0805] When c is 0, Cz and Az are bonded by a single bond,

[0806] When c is 1, 2, 3, 4 or 5, L 23 is selected from

[0807] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and

[0808] a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms

[0809] a linking group selected from the group consisting of

[0810] When c is 2, 3, 4 or 5, a plurality of Ls 23 are the same as or different from each other,

[0811] a plurality of Ls 23 bond to each other to form a ring or do not form a ring,

[0812] Cz is represented by the following general formula (23a).

[0813]

Chemical formula 145

[0814]

[0815] In the general formula (23a),

[0816] Y 21 ~Y 28 are each independently a nitrogen atom or CR A3 ,

[0817] R A3 are each independently a hydrogen atom or a substituent, or a plurality of Rs A3 bond to each other in any one or more groups in the group formed by each other to form a ring,

[0818] As the substituent R A3 are each independently selected from

[0819] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0820] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0821] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0822] A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,

[0823] A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0824] A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0825] A substituted phosphoryl group,

[0826] A substituted silyl group,

[0827] A cyano group,

[0828] A nitro group, and

[0829] A carboxyl group

[0830] A group selected from the group consisting of

[0831] A plurality of Rs A3 Are the same as or different from each other,

[0832] *1 represents a bonding site to a carbon atom in the structure of the linking group represented by L 23 Or a bonding site to a carbon atom in the ring structure represented by Az.

[0833] It is also preferred that Y 21 ~Y 28 Is CR A3 .

[0834] In the general formula (23), it is preferred that c is 0 or 1.

[0835] It is also preferred that Cz is represented by the following general formula (23b), general formula (23c) or general formula (23d).

[0836]

Chemical Formula 146

[0837]

[0838]

Chemical Formula 147

[0839]

[0840]

Chemical Formula 148

[0841]

[0842] In the general formula (23b), general formula (23c) and general formula (23d), Y 21 ~Y 28 And Y 51 ~Y58 are each independently a nitrogen atom or CR A4 ,

[0843] Among them, in the general formula (23b), Y 25 ~Y 28 at least one of which is a carbon atom bonded to any one of Y 51 ~Y 54 , Y 51 ~Y 54 at least one of which is a carbon atom bonded to any one of Y 25 ~Y 28 .

[0844] In the general formula (23c), Y 25 ~Y 28 at least one of which is a carbon atom bonded to a nitrogen atom in a five-membered ring of a nitrogen-containing fused ring containing Y 51 ~Y 58 .

[0845] In the general formula (23d), *a and *b respectively represent bonding sites with any one of Y 21 ~Y 28 , Y 25 ~Y 28 at least one of which is the bonding site represented by *a, Y 25 ~Y 28 at least one of which is the bonding site represented by *b,

[0846] n is 1, 2, 3 or 4,

[0847] R A4 are each independently a hydrogen atom or a substituent, or any one or more groups in a group formed by multiple R A4 bond to each other to form a ring,

[0848] As the substituent, R A4 are each independently selected from

[0849] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0850] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0851] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0852] a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,

[0853] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0854] A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0855] A substituted phosphoryl group,

[0856] A substituted silyl group,

[0857] A cyano group,

[0858] A nitro group, and

[0859] A carboxyl group

[0860] Any substituent selected from the group consisting of

[0861] Multiple Rs A4 Are the same as or different from each other,

[0862] Z 21 And Z 22 Are each independently selected from an oxygen atom, a sulfur atom, NR 45 And CR 46 R 47 Any one selected from the group consisting of

[0863] R 45 Is a hydrogen atom or a substituent,

[0864] R 46 And R 47 Are each independently a hydrogen atom or a substituent, or R 46 And R 47 The groups of combine with each other to form a ring,

[0865] As substituents, R 45 、R 46 And R 47 Are each independently selected from

[0866] A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0867] A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0868] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0869] A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,

[0870] A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0871] A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0872] A substituted phosphoryl group,

[0873] A substituted silyl group,

[0874] cyano,

[0875] nitro, and

[0876] carboxy

[0877] any substituent selected from the group consisting of

[0878] a plurality of Rs 45 are the same as or different from each other,

[0879] a plurality of Rs 46 are the same as or different from each other,

[0880] a plurality of Rs 47 are the same as or different from each other,

[0881] * represents the bonding site to the carbon atom in the ring structure represented by Az.

[0882] Preferably, Z 21 is NR 45 .

[0883] When Z 21 is NR 45 in this case, preferably R 45 is an aryl group having 6 to 30 ring carbon atoms which is substituted or unsubstituted.

[0884] Preferably, Z 22 is NR 45 .

[0885] When Z 22 is NR 45 in this case, preferably R 45 is an aryl group having 6 to 30 ring carbon atoms which is substituted or unsubstituted.

[0886] Y 51 to Y 58 is preferably CR A4 wherein, in this case, at least any one of Y 51 to Y 58 is a carbon atom bonded to the ring structure represented by the general formula (23a).

[0887] It is also preferred that Cz is represented by the general formula (23d) and n is 1.

[0888] Preferably, Az is a ring structure selected from the group consisting of a substituted or unsubstituted pyrimidine ring and a substituted or unsubstituted triazine ring.

[0889] More preferably, Az is a ring structure selected from the group consisting of a pyrimidine ring having substituents and a triazine ring having substituents, and the substituents of these pyrimidine rings and triazine rings are groups selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, and more preferably are substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms.

[0890] When the pyrimidine ring and triazine ring of Az have a substituted or unsubstituted aryl group as a substituent, the ring-forming carbon number of the aryl group is preferably 6 to 20, more preferably 6 to 14, and further preferably 6 to 12.

[0891] When Az has a substituted or unsubstituted aryl group as a substituent, the substituent is preferably any one selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, and substituted or unsubstituted fluorenyl, and more preferably any one selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl.

[0892] When Az has a substituted or unsubstituted heteroaryl group as a substituent, the substituent is preferably any one selected from the group consisting of substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0893] R A4 Each independently is a hydrogen atom or a substituent, and preferably R as a substituent A4 is any one selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms.

[0894] When R as a substituent A4 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, R as a substituent A4 is preferably any one selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, and substituted or unsubstituted fluorenyl, and more preferably any one selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl.

[0895] When R as a substituent A4 is a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, R as a substituent A4Preferably any substituent selected from the group consisting of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.

[0896] R preferably as a substituent 45 , R 46 and R 47 are each independently any substituent selected from the group consisting of 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, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0897] · Method for producing compound M2 of the present embodiment

[0898] Compound M2 of the present embodiment can be produced by a known method.

[0899] · Specific examples of compound M2

[0900] As specific examples of compound M2 of the present embodiment, for example, the following compounds can be cited. However, the present invention is not limited by these specific examples of the compounds.

[0901]

Chemical Formula 149

[0902]

[0903]

Chemical Formula 150

[0904]

[0905]

Chemical Formula 151

[0906]

[0907]

Chemical Formula 152

[0908]

[0909]

Chemical Formula 153

[0910]

[0911]

Chemical Formula 154

[0912]

[0913]

Chemical Formula 155

[0914]

[0915]

Chemical Formula 156

[0916]

[0917]

Chemical 157

[0918]

[0919]

Chemical 158

[0920]

[0921]

Chemical 159

[0922]

[0923]

Chemical 160

[0924]

[0925]

Chemical 161

[0926]

[0927]

Chemical 162

[0928]

[0929]

Chemical 163

[0930]

[0931]

Chemical 164

[0932]

[0933]

Chemical 165

[0934]

[0935]

Chemical 166

[0936]

[0937]

Chemical 167

[0938]

[0939]

Chemical 168

[0940]

[0941]

Chemical 169

[0942]

[0943]

Chemical 170

[0944]

[0945]

Chemical 171

[0946]

[0947]

Chemical 172

[0948]

[0949]

Chemical 173

[0950]

[0951]

Chemical 174

[0952]

[0953]

Chemical 175

[0954]

[0955]

Chemical 176

[0956]

[0957]

Chemical 177

[0958]

[0959]

Chemical 178

[0960]

[0961]

Chemical 179

[0962]

[0963] <Relationship between Compound M3 and Compound M2 in the Light-Emitting Layer>

[0964] In the organic EL element of the present embodiment, the singlet energy S1(M2) of Compound M2 and the singlet energy S1(M3) of Compound M3 satisfy the relationship of the following mathematical formula (Formula 1).

[0965] S1(M3) > S1(M2) … (Formula 1)

[0966] Preferably, the energy gap T 77K (M3) at 77 [K] of Compound M3 is greater than the energy gap T 77K (M2) at 77 [K] of Compound M2. That is, it is preferably to satisfy the relationship of the following mathematical formula (Formula 11).

[0967] T 77K (M3) > T 77K(M2)…(Number 11)

[0968] Preferably, when the organic EL element of the present embodiment emits light, in the light-emitting layer, compound M3 mainly does not emit light.

[0969] · Relationship between triplet energy and energy gap at 77 [K]

[0970] Here, the relationship between the triplet energy and the energy gap at 77 [K] will be described. In the present embodiment, there are differences between the energy gap at 77 [K] and the triplet energy defined normally.

[0971] The measurement of the triplet energy is performed 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, and 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.

[0972] Here, among the compounds of the present embodiment, the compounds with thermally activated delayed fluorescence property are preferably those with a smaller △ST. If △ST is smaller, even in the low temperature (77 [K]) state, intersystem crossing and reverse intersystem crossing are likely to occur, and the singlet excited state and the triplet excited state coexist. As a result, it can be considered that the spectrum measured in the same way as above includes luminescence from both the singlet excited state and the triplet excited state, and it is difficult to distinguish which state the luminescence comes from, but basically the value of the triplet energy is dominant.

[0973] Therefore, in the present embodiment, the measurement method is the same as the usual 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)) at a concentration of 10 μmol / L, and this solution is placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis: phosphorescence emission intensity, and 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 edge [nm] of the intersection of this tangent and the horizontal axis, the energy calculated according to the following conversion formula (F1) is taken as the energy gap T at 77 [K] 77K .

[0974] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0975] The tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum is drawn as follows. Consider that this tangent is the tangent at each point on the curve toward the long-wavelength side when moving on the spectral curve from the maximum value on the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest-wavelength side of the spectrum maximum. This tangent has an increasing slope as the curve rises (i.e., as the value on the vertical axis increases). The tangent drawn at the point where the value of this slope takes the maximum value (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum.

[0976] In addition, the maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the maximum value on the shortest-wavelength side described above, and the tangent 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 to the rising edge on the short-wavelength side of the phosphorescence spectrum.

[0977] The measurement of phosphorescence can be performed using the F-4500 type spectrofluorometer main body 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.

[0978] · Singlet energy S1

[0979] As a method for measuring the singlet energy S1 using a solution (sometimes referred to as the solution method), the following method can be cited as an example.

[0980] Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300 K) (with the vertical axis: absorption intensity, and the horizontal axis: wavelength). Draw a tangent 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 and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy.

[0981] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[0982] 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.

[0983] The tangent to the falling edge on the long-wavelength side of the absorption spectrum is drawn as follows. Consider that this tangent is the tangent at each point on the curve when moving along the long-wavelength direction on the spectral curve from the maximum value on the longest-wavelength side of the absorption spectrum maximum. This tangent has a decreasing slope and then an increasing slope repeatedly as the curve descends (i.e., as the value on the vertical axis decreases). The tangent drawn at the point where the value of the slope takes the minimum value on the longest-wavelength side (where the absorbance does not reach 0.1 or less) is taken as the tangent to the falling edge on the long-wavelength side of the absorption spectrum.

[0984] In addition, a maximum point with an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side described above.

[0985] 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.

[0986] In the present embodiment, the difference ΔST(M2) between the singlet energy S1(M2) of compound M2 and the energy gap T 77K (M2) at 77 [K] of compound M2 is preferably less than 0.3 eV, more preferably less than 0.2 eV, still more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationships of the following mathematical formulas (Equation 1A) to (Equation 1D).

[0987] ΔST(M2) = S1(M2) - T 77K (M2) < 0.3 eV... (Equation 1A)

[0988] ΔST(M2) = S1(M2) - T 77K (M2) < 0.2 eV... (Equation 1B)

[0989] ΔST(M2) = S1(M2) - T 77K (M2) < 0.1 eV... (Equation 1C)

[0990] ΔST(M2) = S1(M2) - T 77K (M2) < 0.01 eV... (Equation 1D)

[0991] · Thickness of the light-emitting layer

[0992] In the organic EL element of the present embodiment, the thickness of the light-emitting layer 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.

[0993] · Content ratio of the compound in the light-emitting layer

[0994] The content ratios of compound M2 and compound M3 contained in the light-emitting layer are preferably within the following ranges, for example.

[0995] The content ratio of compound M2 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 still more preferably 20% by mass or more and 60% by mass or less.

[0996] The content rate of compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and still more preferably 40% by mass or more and 80% by mass or less.

[0997] In addition, this embodiment does not exclude the inclusion of materials other than compound M2 and compound M3 in the light-emitting layer.

[0998] The light-emitting layer may contain only one kind of compound M2, or may contain two or more kinds of compound M2. The light-emitting layer may contain only one kind of compound M3, or may contain two or more kinds of compound M3.

[0999] Figure 4 It is a diagram showing the energy levels of compound M3 and compound M2 in the light-emitting layer and the relationship of energy transfer.

[1000] Figure 4 In, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3.

[1001] Figure 4 The dotted arrows in represent the energy transfer between the respective excited states. Through Förster transfer from the lowest excited singlet state S1 of compound M3, or Dexter transfer from the lowest excited triplet state T1, energy transfer is carried out to the lowest excited singlet state S1 or the lowest excited triplet state T1 of compound M2, respectively.

[1002] Furthermore, if a material with a smaller △ST(M2) is used as compound M2, the lowest excited triplet state T1 of compound M2 can undergo reverse intersystem crossing to the lowest excited singlet state S1 through thermal energy. As a result, fluorescence emission from the lowest excited singlet state S1 of compound M2 can be observed. It is considered that by utilizing the delayed fluorescence based on this TADF mechanism, the internal efficiency can theoretically be increased to 100%.

[1003] The organic EL element of this embodiment contains a delayed fluorescence compound M2 and a compound M3 having a singlet energy larger than that of the compound M2 in the light-emitting layer.

[1004] According to this embodiment, a high-performance organic EL element, for example, an organic EL element that emits light with high efficiency, can be realized.

[1005] The organic EL element of this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1006] The structure of the organic EL element will be further described.

[1007] (Substrate)

[1008] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, and plastic can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include plastic substrates. As materials for forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate can be cited. In addition, an inorganic vapor deposition film can also be used.

[1009] (Anode)

[1010] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or a mixture thereof having 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.

[1011] 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% by mass or more and 10% by mass or less of zinc oxide with respect to indium. In addition, for example, for indium containing tungsten oxide and zinc oxide, it can be formed by sputtering using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide with respect to indium. In addition to this, it can also be fabricated by vacuum evaporation, coating, inkjet, spin coating, etc.

[1012] 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 mixtures thereof, and also include elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1013] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing them (such as MgAg and AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them, etc., which are materials with a smaller work function. Additionally, 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 a silver paste or the like, a coating method or an inkjet method can be used, etc.

[1014] (Cathode)

[1015] The cathode is preferably made of a metal, an alloy, a conductive compound, or a mixture thereof, etc., with a smaller work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing them (such as MgAg and AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them, etc.

[1016] 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. Moreover, when using a silver paste or the like, a coating method or an inkjet method can be used, etc.

[1017] Furthermore, 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, etc., regardless of the work function value. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, etc.

[1018] (Hole injection layer)

[1019] The hole injection layer is a layer containing a substance with high hole injection properties. As substances 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.

[1020] In addition, as substances with high hole injection properties, examples of low molecular weight organic compounds include 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), and other aromatic amine compounds, as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[1021] In addition, as substances with high hole injection properties, high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, examples of high molecular compounds include 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), and other high molecular compounds. In addition, high molecular compounds with added acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[1022] (Hole transport layer)

[1023] The hole transport layer is a layer containing a substance with high hole transportability. 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.

[1024] 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. High molecular compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[1025] However, as long as the substance has higher hole transportability than electrons, other substances can also be used. In addition, the layer containing a substance with high hole transportability can be not only a single layer, but also a layer obtained by laminating two or more layers formed of the above substances.

[1026] When two or more hole transport layers are arranged, it is preferable to arrange a material with a larger energy gap on the side closer to the light-emitting layer. As such a material, compounds EBL and compound EBL-2 used in the following examples can be cited.

[1027] (Electron transport layer)

[1028] 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 organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition, 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), bathocuproine (abbreviation: BPhen), bathocuproin (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, substances other than the 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.

[1029] 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.

[1030] (Electron injection layer)

[1031] 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 transporting 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.

[1032] Alternatively, in the electron injection layer, a composite material formed by mixing an organic compound and an electron donor can also be used. Such a composite material generates electrons in the organic compound through the electron donor, so it has good electron injection property and electron transporting property. In this case, as the organic compound, a material with good electron transport of the generated electrons is preferably used, 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.

[1033] (Layer formation method)

[1034] 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.

[1035] (Film thickness)

[1036] 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.

[1037] The inventors have found that by using the compound M3 represented by the general formula (3) and the delayed fluorescence compound M2 together, a high-performance organic EL element can be achieved.

[1038] Compound M3 has carbazole which can be regarded as at least one of the hole injection site and the hole transport site, and A which has at least one of the hole injection property and the hole transport property higher than that of carbazole. 30 (preferably benzofuran carbazole) both, so with no A 30 On the other hand, compared with a compound having only carbazole (eg, CBP), at least one of the hole injection property and the hole transport property is moderately high.

[1039] In the present embodiment, it is considered that by including in the light-emitting layer a compound M3 that appropriately improves at least one of the hole injection and hole transport properties, an appropriate amount of holes can be supplied to the light-emitting layer, and the amount of holes and electrons can be matched. It can be considered that the result is that the element can be made efficient. Usually, in most cases, the compound of delayed fluorescence introduces a large absolute value of the energy level of LUMO (lowest unoccupied molecular orbital) into the molecule in order to reduce ΔST, and the absolute value of the energy level of HOMO (highest occupied orbital) of the entire molecule is also increased. There are many cases. However, if the absolute value of the energy level of HOMO is large, it is sometimes hindered to inject holes into the light-emitting layer and it becomes impossible to supply an appropriate amount of holes to the light-emitting layer.

[1040] In this embodiment, it can be considered that since the light-emitting layer contains a delayed fluorescence compound M2 and also contains a compound M3 that appropriately improves at least one of the hole injection property and the hole transport property, the situation where the hole injection into the light-emitting layer is hindered is suppressed, and an appropriate amount of holes can be supplied to the light-emitting layer, resulting in the realization of high efficiency of the element.

[1041] Therefore, according to this embodiment, a high-performance organic EL element can be realized.

[1042] The “high performance” in this embodiment mode refers to at least one of emitting light with a long life, improving the light emission efficiency, and reducing the driving voltage.

[1043] [Second embodiment]

[1044] The structure of the organic EL element of the second embodiment is described. In the description of the second embodiment, the same components as those of the first embodiment are given the same reference numerals and names, etc., and the description is omitted or simplified. In addition, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

[1045] The organic EL device of the second embodiment is different from the organic EL device of the first embodiment in that the light-emitting layer further contains a fluorescent compound M1. The other aspects are the same as those of the first embodiment.

[1046] That is, in the second embodiment, the light-emitting layer contains the compound M3 represented by the general formula (3), the delayed fluorescence compound M2, and the fluorescent light-emitting compound M1.

[1047] In the case of this scheme, the compound M1 is preferably a dopant material, the compound M2 is preferably a host material, and the compound M3 is preferably not a dopant material.

[1048] (Compound M1)

[1049] The light-emitting layer of this embodiment contains the fluorescent light-emitting compound M1.

[1050] The compound M1 of this embodiment is not a phosphorescent metal complex. The compound M1 of this embodiment is preferably not a heavy metal complex. In addition, the compound M1 of this embodiment is preferably not a metal complex.

[1051] As the compound M1 of this embodiment, a fluorescent light-emitting material can be used. As the fluorescent light-emitting material, specifically, for example, diarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, diarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, diarylaminopyrene derivatives, aryl-substituted pyrene derivatives, diarylamino derivatives, aryl-substituted derivatives, diarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indeno[1,2,3-cd]pyrene derivatives, acenaphtho[1,2,3-cd]fluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and tetracene derivatives, etc.

[1052] The compound M1 of this embodiment is preferably a compound represented by the following general formula (10).

[1053]

Chemical 180

[1054]

[1055] In the general formula (10),

[1056] X is a nitrogen atom or a carbon atom bonded to Y,

[1057] Y is a hydrogen atom or a substituent,

[1058] R 10 ~R 15 are each independently a hydrogen atom or a substituent, or the group of R 10 and R 11 , the group of R 11 and R 12 , the group of R 13 and R14 groups, and R 14 and R 15 any one or more of the groups in the group are bonded to each other to form a ring,

[1059] Y and R as substituents 10 ~R 15 are each independently selected from

[1060] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1061] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1062] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1063] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1064] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1065] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms,

[1066] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[1067] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1068] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1069] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1070] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[1071] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[1072] a halogen atom,

[1073] a carboxyl group,

[1074] a substituted or unsubstituted ester group,

[1075] a substituted or unsubstituted carbamoyl group,

[1076] a substituted or unsubstituted amino group,

[1077] a nitro group,

[1078] a cyano group,

[1079] a substituted or unsubstituted silyl group, and

[1080] selected from the group consisting of substituted or unsubstituted siloxanyl groups,

[1081] Z 11 and Z 12 are each independently a substituent, or Z 11 and Z 12 are bonded to each other to form a ring,

[1082] Z as a substituent 11 and Z 12 are each independently selected from

[1083] a halogen atom,

[1084] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1085] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1086] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1087] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1088] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and

[1089] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[1090] In the general formula (10), for example, when the groups of R 14 and R 15 are bonded to each other to form a ring, the compound M1 is represented by the following general formula (11).

[1091]

Chemical 181

[1092]

[1093] In the general formula (11), X, Y, R 10 to R 13 , Z 11 and Z 12 are respectively synonymous with X, Y, R 10 to R 13 , Z 11 and Z 12 in the general formula (10), R 16 to R 19 are each independently a hydrogen atom or a substituent, and R 16 to R 19 as substituents are each independently synonymous with R 10 to R 13 as substituents.

[1094] In the general formula (10), when Z 11 and Z 12 are bonded to each other to form a ring, the compound M1 is represented by, for example, the following general formula (10A) or the following general formula (10B). However, the compound M1 is not limited to the following structures.

[1095]

Chemical 182

[1096]

[1097] In the general formula (10A), X, Y, and R 10 ~R 15 are respectively synonymous with X, Y, and R 10 ~R 15 in the general formula (10), R 1A are each independently a hydrogen atom or a substituent, and R 1A as a substituent is synonymous with R 10 ~R 15 in the general formula (10), and n3 is 4.

[1098] In the general formula (10B), X, Y, and R 10 ~R 15 are respectively synonymous with X, Y, and R 10 ~R 15 in the general formula (10), R 1B are each independently a hydrogen atom or a substituent, and R 1B as a substituent is synonymous with R 10 ~R 15 in the general formula (10), and n4 is 4.

[1099] Z 11 and Z 12 at least one of (preferably both Z 11 and Z 12 ) is preferably 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.

[1100] Z 11 and Z 12At least any one of them is more preferably a group selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms obtained by substituting with a fluorine atom, an aryloxy group having 6 to 30 ring-constituting carbon atoms obtained by substituting with a fluorine atom, and an aryloxy group having 6 to 30 ring-constituting carbon atoms obtained by substituting with a fluoroalkyl group having 1 to 30 carbon atoms.

[1101] It is further preferably Z 11 and Z 12 At least any one of them is an alkoxy group having 1 to 30 carbon atoms obtained by substituting with a fluorine atom, and it is even more preferably Z 11 and Z 12 is an alkoxy group having 1 to 30 carbon atoms obtained by substituting with a fluorine atom.

[1102] It is also preferably Z 11 and Z 12 are the same group.

[1103] On the other hand, it is also preferably that at least any one of the said Z 11 and the said Z 12 is a fluorine atom, and it is even more preferably that the said Z 11 and the said Z 12 are fluorine atoms.

[1104] It is also preferably that at least any one of the said Z 11 and the said Z 12 is a group represented by the following general formula (10a).

[1105]

Chemical formula 183

[1106]

[1107] In the said 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-constituting carbon atoms, L1 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-constituting carbon atoms, m is 0, 1, 2, 3, 4, 5, 6 or 7, and when m is 2, 3, 4, 5, 6 or 7, a plurality of L1s 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).

[1108] In the said general formula (10), when Z 11 and Z 12 are groups represented by the said general formula (10a), compound M1 is a compound represented by the following general formula (12).

[1109] Compound M1 is also preferably a compound represented by the following general formula (12).

[1110]

Chemical 184

[1111]

[1112] In the general formula (12), when X and X are carbon atoms bonded to Y, Y and R 10 ~R 15 are respectively synonymous with X, Y, and R 10 ~R 15 in the general formula (10). A 11 and A 12 are synonymous with A in the general formula (10a) and can be the same as or different from each other. L 11 and L 12 are synonymous with L1 in the general formula (10a) and can 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 multiple Ls 11 are the same as or different from each other, and when m2 is 2, 3, 4, 5, 6, or 7, the multiple Ls 12 are the same as or different from each other. When m1 is 0, A 11 is directly bonded to O (oxygen atom), and when m2 is 0, A 12 is directly bonded to O (oxygen atom).

[1113] At least any one of A and L1 in the general formula (10a) is preferably substituted with a halogen atom, more preferably substituted with a fluorine atom.

[1114] 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.

[1115] L1 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.

[1116] That is, the compound M1 is also preferably a compound represented by the following general formula (12a).

[1117]

Chemical 185

[1118]

[1119] In the general formula (12a),

[1120] X is synonymous with X in the general formula (10), and when X is a carbon atom bonded to Y, Y is synonymous with Y in the general formula (10),

[1121] R 10 ~R 15 are each independently the same as R in the general formula (10) 10 ~R 15 .

[1122] m3 is 0, 1, 2, 3 or 4,

[1123] m4 is 0, 1, 2, 3 or 4,

[1124] and m3 and m4 are the same as or different from each other.

[1125] In the general formulas (10), (11), (12) and (12a),

[1126] X is a carbon atom bonded to Y,

[1127] Y is a hydrogen atom or a substituent,

[1128] 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.

[1129] In the general formulas (10), (11), (12) and (12a),

[1130] As a more preferred embodiment, the following embodiments can be cited:

[1131] X is a carbon atom bonded to Y,

[1132] Y is a hydrogen atom or a substituent,

[1133] Y as the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1134] In the case where Y as the substituent is a substituted aryl group having 6 to 30 ring carbon atoms, the substituent is

[1135] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1136] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1137] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1138] a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, or

[1139] an aryl group having 6 to 30 ring carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms.

[1140] In the compound M1, it may be the said Z 11 With the said Z 12 Bond to each other to form a ring, but preferably the said Z 11 With the said Z 12 Do not bond to each other to form a ring.

[1141] In the general formulas (10), (12) and (12a), preferably R 10 , R 12 , R 13 And R 15 At least any one of them is an alkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted, or a haloalkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted.

[1142] In the general formulas (10), (12) and (12a), more preferably R 10 , R 12 , R 13 And R 15 Are an alkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted, or a haloalkyl group with 1 to 30 carbon atoms which is substituted or unsubstituted. In this case, preferably R 11 And R 14 Are hydrogen atoms.

[1143] In the general formulas (10), (12) and (12a), preferably R 10 , R 12 , R 13 And R 15 At least any one of them is an aryl group with 6 to 30 ring-forming carbon atoms which is substituted or unsubstituted.

[1144] In the general formulas (10), (12) and (12a), more preferably R 10 , R 12 , R 13 And R 15 Are an aryl group with 6 to 30 ring-forming carbon atoms which is substituted or unsubstituted. In this case, preferably R 11 And R 14 Are hydrogen atoms.

[1145] In the general formulas (10), (12) and (12a),

[1146] As a more preferred embodiment, the following embodiments can be exemplified:

[1147] R 10 , R 12 , R 13 And R 15 Are each independently

[1148] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[1149] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[1150] an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) obtained by substituting with an alkyl group having 1 to 30 carbon atoms,

[1151] R 11 and R 14 is a hydrogen atom.

[1152] In the general formula (11), preferably, at least one of R 10 , R 12 and R 13 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.

[1153] In the general formula (11), more preferably, R 10 , R 12 and R 13 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 11 is a hydrogen atom.

[1154] In the general formula (11), preferably, at least one of R 10 , R 12 and R 13 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1155] In the general formula (11), more preferably, R 10 , R 12 and R 13 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In this case, preferably, R 11 is a hydrogen atom.

[1156] In the general formula (11),

[1157] As a more preferred embodiment, the following embodiments can be exemplified:

[1158] R 10 , R 12 and R 13 are each independently

[1159] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),

[1160] A substituted or unsubstituted haloalkyl having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or

[1161] an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) obtained by substituting an alkyl group having 1 to 30 carbon atoms,

[1162] R 11 is a hydrogen atom.

[1163] In compound M1, examples of the alkoxy group obtained by substituting 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(bis(trifluoromethyl))ethenoxy, 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, etc.

[1164] In compound M1, examples of the aryloxy group obtained by substituting a fluorine atom or the aryloxy group obtained by substituting 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, etc.

[1165] When compound M1 is a fluorescent compound, compound M1 preferably emits light with a main peak wavelength of 400 nm or more and 700 nm or less.

[1166] In this specification, the main peak wavelength refers to the peak wavelength of the fluorescence spectrum with the maximum emission intensity measured for a toluene solution of the compound to be measured dissolved at a concentration of 10 -6 mol / L or more and 10 -5 mol / L or less. A spectrofluorometer (manufactured by Hitachi High-Technologies Corporation, F-7000) is used as the measuring device.

[1167] Compound M1 preferably emits red light or green light.

[1168] In this specification, the red luminescence refers to the luminescence with the main peak wavelength of the fluorescence spectrum within the range of more than 600 nm and less than 660 nm.

[1169] When compound M1 is a red fluorescent compound, the main peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and still more preferably 610 nm or more and 630 nm or less.

[1170] In this specification, the green luminescence refers to the luminescence with the main peak wavelength of the fluorescence spectrum within the range of more than 500 nm and less than 560 nm.

[1171] When compound M1 is a green fluorescent compound, the main peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and still more preferably 510 nm or more and 540 nm or less.

[1172] In this specification, the blue luminescence refers to the luminescence with the main peak wavelength of the fluorescence spectrum within the range of more than 430 nm and less than 480 nm.

[1173] When compound M1 is a blue fluorescent compound, the main peak wavelength of compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[1174] The measurement of the main peak wavelength of the light emitted from the organic EL element is carried out as described below.

[1175] 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 so that the current density reaches 10 mA / cm 2 at this time.

[1176] In the obtained spectro-emission luminance spectrum, measure the peak wavelength of the emission spectrum with the maximum emission intensity, and use it as the main peak wavelength (unit: nm).

[1177] · Manufacturing method of compound M1

[1178] Compound M1 can be manufactured by a known method.

[1179] · Specific examples of compound M1

[1180] Specific examples of compound M1 of the present embodiment are shown below. Among them, the present invention is not limited by these specific examples of the compounds.

[1181] In addition, the coordination bond between the boron atom and the nitrogen atom in the pyrromethine skeleton has various marking methods 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.

[1182]

Chemical 186

[1183]

[1184]

Chemical 187

[1185]

[1186]

Chemical 188

[1187]

[1188]

Chemical 189

[1189]

[1190]

Chemical 190

[1191]

[1192]

Chemical 191

[1193]

[1194]

Chemical 192

[1195]

[1196] <Relationship among Compound M3, Compound M2, and Compound M1 in the Light-Emitting Layer>

[1197] In the organic EL element of this embodiment, it is preferable that the singlet energy S1(M2) of Compound M2 and the singlet energy S1(M1) of Compound M1 satisfy the relationship of the following mathematical formula (Equation 2).

[1198] S1(M2) > S1(M1) … (Equation 2)

[1199] In addition, it is preferable that the singlet energy S1(M3) of Compound M3 is greater than the singlet energy S1(M1) of Compound M1.

[1200] S1(M3) > S1(M1) … (Equation 2A)

[1201] It is preferable that the singlet energy S1(M3) of Compound M3, the singlet energy S1(M2) of Compound M2, and the singlet energy S1(M1) of Compound M1 satisfy the relationship of the following mathematical formula (Equation 2B).

[1202] S1(M3) > S1(M2) > S1(M1) … (Equation 2B)

[1203] Preferably, when the organic EL element of the present embodiment emits light, in the light-emitting layer, mainly the fluorescent compound M1 emits light.

[1204] Preferably, the organic EL element of the present embodiment emits red light or green light.

[1205] · Content ratio of the compounds in the light-emitting layer

[1206] The content ratios of the compounds M3, M2, and M1 contained in the light-emitting layer are preferably within the following ranges, for example.

[1207] The content ratio of the compound M3 is preferably 10% by mass or more and 80% by mass or less.

[1208] The content ratio of the compound M2 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.

[1209] The content ratio of the compound M1 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.

[1210] The upper limit of the total content ratio of the compounds M3, M2, and M1 in the light-emitting layer is 100% by mass. In addition, it is not excluded that materials other than the compounds M3, M2, and M1 are included in the light-emitting layer of the present embodiment.

[1211] The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3. The light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2. The light-emitting layer may contain only one type of compound M1, or may contain two or more types of compound M1.

[1212] Figure 5 It is a diagram showing an example of the relationship between the energy levels of the compounds M3, M2, and M1 in the light-emitting layer. Figure 5 In the figure, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the compound M1, and T1(M1) represents the lowest excited triplet state of the compound M1. S1(M2) represents the lowest excited singlet state of the compound M2, and T1(M2) represents the lowest excited triplet state of the compound M2. S1(M3) represents the lowest excited singlet state of the compound M3, and T1(M3) represents the lowest excited triplet state of the compound M3. Figure 5The dotted arrow from S1(M2) to S1(M1) indicates Förster-type energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1.

[1213] As Figure 5 shown, if a compound with a smaller △ST(M2) is used as compound M2, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) through thermal energy. Also, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of compound M2 to compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of compound M1 can be observed. It is considered that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1214] The organic EL element of the second embodiment includes a delayed fluorescence compound M2, a compound M3 having a singlet energy larger than that of the compound M2, and a compound M1 having a singlet energy smaller than that of the delayed fluorescence compound M2 in the light-emitting layer.

[1215] According to the second embodiment, a high-performance organic EL element, such as an organic EL element that emits light with high efficiency, can be achieved.

[1216] The organic EL element of the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1217] [Third Embodiment]

[1218] [Compound]

[1219] The compound of the third embodiment is a compound represented by the following general formula (301). As a specific example of the compound of the third embodiment, the compounds belonging to the following general formula (301) in the specific examples of M3 in the first embodiment are cited.

[1220] [Chemical Formula 193]

[1221]

[1222] (In the general formula (301), 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).)

[1223] [Chemical Formula 194]

[1224]

[1225]

Chemistry 195

[1226]

[1227]

Chemistry 196

[1228]

[1229] (In the general formula (31a), general formula (31b), general formula (31c), general formula (31d), general formula (31e) and general formula (31f),

[1230] R 310 ~R 319 are independently a hydrogen atom or a substituent,

[1231] R 320 ~R 329 are independently a hydrogen atom or a substituent,

[1232] R 330 ~R 339 are independently a hydrogen atom or a substituent,

[1233] R 340 ~R 349 are independently a hydrogen atom or a substituent,

[1234] R 350 ~R 359 are independently a hydrogen atom or a substituent,

[1235] R 360 ~R 369 are independently a hydrogen atom or a substituent,

[1236] 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 Independently,

[1237] Halogen atoms,

[1238] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1239] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1240] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1241] A substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1242] A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1243] A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[1244] A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[1245] A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[1246] A substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[1247] A hydroxyl group,

[1248] A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1249] A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1250] An amino group,

[1251] A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[1252] A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[1253] A mercapto group,

[1254] A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[1255] A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1256] * represents the bonding position of the benzene ring bonded to R 401 ~R 404 (The bonding position of the benzene ring.)

[1257] (In the general formula (301),

[1258] R 31 ~R 38 Are each independently a hydrogen atom or a substituent,

[1259] R 401 ~R 412 Are each independently a hydrogen atom or a substituent,

[1260] As substituents, R 31 ~R 38 And as substituents, R 401~R 412 Each independently is

[1261] a halogen atom,

[1262] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1263] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1264] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1265] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1266] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1267] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[1268] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[1269] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[1270] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[1271] a hydroxyl group,

[1272] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1273] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1274] an amino group,

[1275] a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,

[1276] a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,

[1277] a mercapto group,

[1278] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[1279] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1280] n is 0, 1, 2 or 3,

[1281] When there are multiple Rs 405 , the multiple Rs 405 are the same or different from each other,

[1282] When there are multiple Rs 406In the case of multiple Rs 406 are the same as or different from each other,

[1283] In the case of multiple Rs 407 are the same as or different from each other, 407 are the same as or different from each other,

[1284] In the case of multiple Rs 408 are the same as or different from each other.) 408 are the same as or different from each other.)

[1285] In the general formula (31a), the groups of R 310 and R 311 , the groups of R 311 and R 312 , the groups of R 312 and R 313 , the groups of R 314 and R 315 , the groups of R 316 and R 317 , the groups of R 317 and R 318 , and the group of R 318 and R 319 do not bond to each other.

[1286] In the general formula (31b), the groups of R 320 and R 321 , the groups of R 321 and R 322 , the groups of R 322 and R 323 , the groups of R 324 and R 325 , the groups of R 326 and R 327 , the groups of R 327 and R 328 , and the group of R 328 and R 329 do not bond to each other.

[1287] In the general formula (31c), the groups of R 330 and R 331 , the groups of R 331 and R 332 , the groups of R 332 and R 333 , the groups of R 335 and R 336 , the groups of R 336 and R 337 , and the group of R 337 and R 338 do not bond to each other.

[1288] In the general formula (31d), R 340 and R 341 groups, R 341 and R 342 groups, R 342 and R 343 groups, R 345 and R 346 groups, R 346 and R 347 groups, and also R 347 and R 348 groups do not bond to each other.

[1289] In the general formula (31e), R 350 and R 351 groups, R 351 and R 352 groups, R 352 and R 353 groups, R 354 and R 355 groups, R 355 and R 356 groups, R 356 and R 357 groups, and also R 358 and R 359 groups do not bond to each other.

[1290] In the general formula (31f), R 360 and R 361 groups, R 361 and R 362 groups, R 362 and R 363 groups, R 364 and R 365 groups, R 365 and R 366 groups, R 366 and R 367 groups, and also R 368 and R 369 groups do not bond to each other.

[1291] In the compound of the third embodiment, preferably n is 0 or 1.

[1292] The compound of the third embodiment is preferably represented by the following general formula (302).

[1293]

Chemical Formula 197

[1294]

[1295] (A in the general formula (302) 31 , R401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 are respectively synonymous with A in the general formula (301).) 31 、R 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 synonymous.)

[1296] In the compound of the third embodiment, preferably A 31 is a group represented by the general formula (31a) or the general formula (31d).

[1297] The compound of the third embodiment is preferably represented by the following general formula (303).

[1298]

Chemical 198

[1299]

[1300] (R in the general formula (303) 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 、R 310 ~R 319 are respectively synonymous with R in the general formula (301).) 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 、R 310 ~R 319 synonymous.)

[1301] In the compound of the third embodiment, preferably R 31 ~R 38 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1302] In the compound of the third embodiment, more preferably R 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1303] In the compound of the third embodiment, R is further preferably 31 ~R 38 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1304] In the compound of the third embodiment, R is even more preferably 31 ~R 38 is a hydrogen atom.

[1305] In the compound of the third embodiment, R is preferably 401 ~R 412 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1306] In the compound of the third embodiment, R is more preferably 401 ~R 412 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1307] In the compound of the third embodiment, R is further preferably 401 ~R 412 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1308] In the compound of the third embodiment, R is even more preferably 401 ~R 412 is a hydrogen atom.

[1309] In the compound of the third embodiment, R 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 a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1310] In the compound of the third embodiment, R 401 ~R 412 and also R 31 ~R 38Each of them is independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1311] Among the compounds of the third embodiment, R 401 ~R 412 And R 31 ~R 38 Each of them is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1312] In the compound of the third embodiment, it is further preferred that R 401 ~R 412 And R 31 ~R 38 Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1313] In the compound of the third embodiment, it is further preferred that R 401 ~R 412 And R 31 ~R 38 A hydrogen atom.

[1314] Among the compounds of the third embodiment, R 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 of them is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1315] In the compound of the third embodiment, it is further preferred that R 310 ~R 319 , R 320 ~R 329 , R 330 ~R 339 , R 340 ~R 349 , R 350 ~R 359 and R 360 ~R 369Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1316] In the compound of the third embodiment, it is further preferred that R 310 ~R 319 , R 320 ~R 329 , R 330 ~R 339 , R 340 ~R 349 , R 350 ~R 359 and R 360 ~R 369 A hydrogen atom.

[1317] The compound of the third embodiment also corresponds to a compound of one embodiment of the compound M3 described in the first embodiment. Therefore, specific examples of the compound of the third embodiment are also shown in the specific examples of the compound M3 described in the first embodiment.

[1318] [Organic EL element]

[1319] The organic EL device as one mode of the third embodiment is an organic EL device in which the compound M3 in the organic EL device of the first embodiment is replaced by the compound of the third embodiment.

[1320] The compound of the third embodiment can achieve higher performance of an organic EL element, for example, can improve the light emission efficiency of the organic EL element.

[1321] Therefore, the organic EL element as one aspect of the third embodiment also has high performance, for example, high light emission efficiency.

[1322] [Fourth embodiment]

[1323] [Compound]

[1324] The compound of the fourth embodiment is a compound represented by the following general formula (310). As specific examples of the compound of the fourth embodiment, compounds belonging to the following general formula (310) among the specific examples of M3 in the first embodiment are cited.

[1325]

Chemistry 199

[1326]

[1327] (In the general formula (310),

[1328] R 310 ~R 319 are each independently a hydrogen atom or a substituent,

[1329] R 31 ~R 38 are each independently a hydrogen atom or a substituent,

[1330] R 401 ~R 412 are each independently a hydrogen atom or a substituent,

[1331] R as a substituent 310 ~R 319 and R as a substituent 31 ~R 38 and also R as a substituent 401 ~R 412 are each independently,

[1332] a halogen atom,

[1333] an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted,

[1334] a heterocyclic group having 5 to 30 ring atoms which may be substituted or unsubstituted,

[1335] an alkyl group having 1 to 30 carbon atoms which may be substituted or unsubstituted,

[1336] a haloalkyl group having 1 to 30 carbon atoms which may be substituted or unsubstituted,

[1337] an alkenyl group having 2 to 30 carbon atoms which may be substituted or unsubstituted,

[1338] an alkynyl group having 2 to 30 carbon atoms which may be substituted or unsubstituted,

[1339] an alkylsilyl group having 3 to 30 carbon atoms which may be substituted or unsubstituted,

[1340] an arylsilyl group having 6 to 60 ring carbon atoms which may be substituted or unsubstituted,

[1341] an arylphosphoryl group having 6 to 60 ring carbon atoms which may be substituted or unsubstituted,

[1342] a hydroxyl group,

[1343] an alkoxy group having 1 to 30 carbon atoms which may be substituted or unsubstituted,

[1344] an aryloxy group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted,

[1345] an amino group,

[1346] an alkylamino group having 2 to 30 carbon atoms which may be substituted or unsubstituted,

[1347] an arylamino group having 6 to 60 ring carbon atoms which may be substituted or unsubstituted,

[1348] a mercapto group,

[1349] A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or

[1350] a substituted or unsubstituted arylthio group having 6 to 30 ring-constituting carbon atoms,

[1351] n is 0, 1, 2 or 3,

[1352] When there are multiple Rs 405 , the multiple Rs 405 are the same as or different from each other,

[1353] When there are multiple Rs 406 , the multiple Rs 406 are the same as or different from each other,

[1354] When there are multiple Rs 407 , the multiple Rs 407 are the same as or different from each other,

[1355] When there are multiple Rs 408 , the multiple Rs 408 are the same as or different from each other.)

[1356] In the compound of the fourth embodiment, the groups of R 310 and R 311 , the groups of R 311 and R 312 , the groups of R 312 and R 313 , the groups of R 313 and R 314 , the groups of R 314 and R 315 , the groups of R 315 and R 316 , the groups of R 316 and R 317 , the groups of R 317 and R 318 , the groups of R 318 and R 319 do not bond to each other.

[1357] In the compound of the fourth embodiment, preferably n is 0 or 1.

[1358] The compound of the fourth embodiment is preferably represented by the following general formula (311).

[1359]

Chemical Formula 200

[1360]

[1361] (R in the general formula (311) 310 to R 319 , R401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 are respectively synonymous with R 310 ~R 319 、R 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 in the general formula (310).)

[1362] In the compound of the fourth embodiment, preferably, R 31 ~R 38 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1363] In the compound of the fourth embodiment, more preferably, R 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1364] In the compound of the fourth embodiment, still more preferably, R 31 ~R 38 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1365] In the compound of the fourth embodiment, even more preferably, R 31 ~R 38 is a hydrogen atom.

[1366] In the compound of the fourth embodiment, preferably, R 401 ~R 412 are each independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1367] In the compound of the fourth embodiment, more preferably, R 401 ~R 412 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1368] In the compound of the fourth embodiment, still more preferably, R 401 ~R412 Each is independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1369] In the compound of the fourth embodiment, R is more preferably 401 ~R 412 a hydrogen atom.

[1370] In the compound of the fourth embodiment, R is preferably 401 ~R 412 and R is also 31 ~R 38 Each is independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1371] In the compound of the fourth embodiment, R is even more preferably 401 ~R 412 and R is also 31 ~R 38 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1372] In the compound of the fourth embodiment, R is further preferably 401 ~R 412 and R is also 31 ~R 38 Each is independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1373] In the compound of the fourth embodiment, R is more preferably 401 ~R 412 and R is also 31 ~R 38 a hydrogen atom.

[1374] In the compound of the fourth embodiment, R is further preferably 310 ~R 319 Each is independently a hydrogen 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1375] In the compound of the fourth embodiment, R is even more preferably 310 ~R 319 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[1376] In the compound of the fourth embodiment, R is further preferably 310 ~R 319 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1377] In the compound of the fourth embodiment, R is even more preferably 310 ~R 319 is a hydrogen atom.

[1378] In addition, the compound of the fourth embodiment also corresponds to a compound of one aspect of the compound M3 described in the first embodiment. Therefore, specific examples of the compound of the fourth embodiment are also shown in the specific examples of the compound M3 described in the first embodiment.

[1379] [Organic EL element]

[1380] As one aspect of the organic EL element of the fourth embodiment, the organic EL element is obtained by substituting the compound M3 in the organic EL element of the first embodiment with the compound of the fourth embodiment.

[1381] The compound of the fourth embodiment can achieve high performance of the organic EL element, for example, can improve the luminous efficiency of the organic EL element.

[1382] Therefore, as one aspect of the organic EL element of the fourth embodiment, the organic EL element is also of high performance, for example, has a high luminous efficiency.

[1383] [Fifth embodiment]

[1384] [Electronic device]

[1385] The electronic device of the present embodiment is equipped with the organic EL element of any one of the above embodiments. 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.

[1386] [Sixth embodiment]

[1387] [Material for organic EL element]

[1388] The material for an organic EL element of the sixth embodiment contains at least any one of the compound of the third embodiment and the compound of the fourth embodiment.

[1389] According to the material for an organic EL element of the sixth embodiment, high performance of the organic EL element can be achieved, for example, the luminous efficiency of the organic EL element can be improved.

[1390] In addition, the material for an organic EL element of the sixth embodiment may also contain other compounds. When the material for an organic EL element of the sixth embodiment further contains other compounds, these other compounds may be solid or liquid.

[1391] 〔Modifications of the Embodiment〕

[1392] In addition, the present invention is not limited to the above-described embodiments, and modifications, improvements, etc. within the scope capable of achieving the object of the present invention are included in the present invention.

[1393] 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, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission caused by direct electron transfer from a triplet excited state to the ground state.

[1394] 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.

[1395] In addition, for example, a blocking layer may be 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 one of holes, electrons, and excitons.

[1396] For example, when a blocking layer is disposed in contact with the cathode side of the light-emitting layer, the blocking layer transports electrons and blocks holes from reaching the layer on the cathode side of the blocking layer (for example, the electron transport layer). When the organic EL element includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer.

[1397] In addition, when a blocking layer is disposed in contact with the anode side of the light-emitting layer, the blocking layer transports holes and blocks electrons from reaching the layer on the anode side of the blocking layer (for example, the hole transport layer). When the organic EL element includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer.

[1398] In addition, the blocking layer may be disposed adjacent to the light-emitting layer so that the excitation energy does not leak from the light-emitting layer to its peripheral layer. The movement of excitons generated in the light-emitting layer to the layer on the electrode side of the blocking layer (for example, the electron transport layer and the hole transport layer, etc.) is blocked.

[1399] It is preferable that the light-emitting layer and the blocking layer are joined.

[1400] 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.

[1401] 〔Other Explanation〕

[1402] In this specification, the numerical range indicated by "~" means the range including the numerical value before "~" as the lower limit value and the numerical value after "~" as the upper limit value.

[1403] In this specification, Rx and Ry bonding to each other to form a ring means that, for example, Rx and Ry contain carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms or silicon atoms, and the atoms (carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms or silicon atoms) contained in Rx are bonded to the atoms (carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms or silicon atoms) contained in Ry via a single bond, double bond, triple bond or divalent linking group to form a ring having 5 or more ring-forming atoms (specifically, a heterocyclic ring or an aromatic hydrocarbon ring). x is a number, a character or a combination of a number and a character. y is a number, a character or a combination of a number and a character.

[1404] There is no particular limitation on the divalent linking group. For example, -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa- and groups obtained by combining two or more of these linking groups can be exemplified.

[1405] As a specific example of the heterocyclic ring, a ring structure (heterocyclic ring) obtained by removing a chemical bond from the "heteroaryl Sub2" exemplified in the "Explanation of Each Substituent in the General Formula" described later can be exemplified. These heterocyclic rings may have substituents.

[1406] As a specific example of the aromatic hydrocarbon ring, a ring structure (aromatic hydrocarbon ring) obtained by removing a chemical bond from the "aryl Sub1" exemplified in the "Explanation of Each Substituent in the General Formula" described later can be exemplified. These aromatic hydrocarbon rings may have substituents.

[1407] 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 "Explanation of Each Substituent in the General Formula" described later can be exemplified.

[1408] 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).

[1409] In the general formulas (E1) to (I1), * each independently represents the position of bonding to other atoms in a 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).

[1410]

Chemical formula 201

[1411]

[1412]

Chemical formula 202

[1413]

[1414] 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 a 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).

[1415] 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) each independently correspond to the two * in the general formulas (E2) and (E1).

[1416] 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 the following general formula (E4). Here, the two * in general formula (E4) respectively independently correspond to the two * in general formula (E2) and general formula (E1). In general formulas (E3) and (E4), * respectively independently represents the position of bonding to other atoms in one molecule.

[1417]

Chemical formula 203

[1418]

[1419] 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 whose atoms are bonded to form a ring structure (such as a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a 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 a substituent is not included in the number of ring-forming carbon atoms.

[1420] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself in a compound whose atoms are bonded to form a ring structure (such as a monocyclic ring, a fused-ring, a ring assembly) (such as a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a 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 a pyridine ring or a quinazoline ring and atoms constituting a 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 a substituent is not included in the number of ring-forming atoms.

[1421] · Explanation of each substituent in the general formula in this specification (Explanation of each substituent)

[1422] As used herein, an aryl group (sometimes referred to as an aromatic hydrocarbon group) is, for example, aryl Sub1, which is at least one group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyrenyl, -yl, fluoranthenyl, benzo[a]anthracenyl, benzo[c]phenanthrenyl, triphenylene, benzo[k]fluoranthenyl, benzo[g] -yl, benzo[b]triphenylene, picenyl, and perylenyl.

[1423] As aryl Sub1 in this specification, the number of ring carbon atoms is preferably 6-30, more preferably 6-22, further preferably 6-20, still further preferably 6-14, and yet further preferably 6-12. Among the above aryl Sub1, phenyl, biphenyl, naphthyl, phenanthrenyl, 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 hereinafter in this specification.

[1424] As used herein, a heteroaryl group (sometimes referred to as a heterocyclic group, heteroaromatic ring group, or aromatic heterocyclic group) is, for example, heterocyclic group Sub2. Heterocyclic group Sub2 is a group containing at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium, and germanium atoms as a heteroatom. Heterocyclic group Sub2 is preferably a group containing at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom.

[1425] As heterocyclic group Sub2 in this specification, for example, it is at least one group selected from the group consisting of pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthroline, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuryl, benzothienyl, benzoxazolyl, benzothiazolyl, benzoisoxazolyl, benzoisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzofuryl, dibenzothienyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, and phenoxazinyl.

[1426] 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 Sub1 or the substituted or unsubstituted heterocyclic group Sub2 in this specification.

[1427] In addition, in this specification, the heterocyclic group Sub2 may also be, for example, a group derived from the partial structures represented by the following general formulas (XY-1) to (XY-18).

[1428]

Chemical formula 204

[1429]

[1430]

Chemical formula 205

[1431]

[1432]

Chemical formula 206

[1433]

[1434] 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 this heterocyclic group may have a substituent.

[1435] 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 can also be appropriately changed.

[1436]

Chemical formula 207

[1437]

[1438] The alkyl group in this specification can be any of a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group.

[1439] The alkyl group in this specification is, for example, alkyl Sub3.

[1440] The linear alkyl group in this specification is, for example, linear alkyl Sub 31 .

[1441] The branched alkyl group in this specification is, for example, branched alkyl Sub 32 .

[1442] The cyclic alkyl group in this specification is, for example, cyclic alkyl Sub 33 .

[1443] 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 .

[1444] 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.

[1445] The linear alkyl Sub in this specification 31 or branched alkyl Sub 32 preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms. As the above linear alkyl Sub 31 or branched alkyl Sub 32 , even more preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, pentyl, isopentyl, and neopentyl.

[1446] The cyclic alkyl Sub in this specification 33 is, for example, cycloalkyl Sub 331 .

[1447] The cycloalkyl Sub in this specification 331 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 ring-forming carbon atoms of cycloalkyl Sub 331 preferably is 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and even more preferably 5 to 8. In cycloalkyl Sub 331Among them, a cyclopentyl group or a cyclohexyl group is more preferably used.

[1448] The haloalkyl group in this specification is, for example, haloalkyl Sub4, and haloalkyl Sub4 is an alkyl group obtained by substituting 1 or more halogen atoms, preferably fluorine atoms, for alkyl Sub3.

[1449] 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.

[1450] 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.

[1451] The alkylsilyl Sub 51 in this specification is, for example, a trialkylsilyl Sub 511 having the above alkyl Sub3.

[1452] 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 3 alkyl Sub3 in the trialkylsilyl Sub 511 can be the same or different from each other.

[1453] 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.

[1454] The dialkylarylsilyl Sub 521 is, for example, a dialkylarylsilyl having 2 of the above alkyl Sub3 and 1 of the above aryl Sub1. The carbon number of the dialkylarylsilyl Sub 521 is preferably 8 to 30.

[1455] 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.

[1456] 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.

[1457] 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.

[1458] The aralkyl group (sometimes referred to as arylalkyl) in this specification is, for example, aralkyl Sub7. The aryl in aralkyl Sub7 includes at least one of the above aryl Sub1 and the above heteroaryl Sub2.

[1459] The aralkyl Sub7 in this specification is preferably a group having aryl Sub1, 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. Preferably, the aryl part of the aralkyl Sub7 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.

[1460] 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.

[1461] The haloalkoxy group in the present 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.

[1462] The aryloxy group (sometimes referred to as arylalkoxy group) in the present specification is, for example, arylalkoxy Sub 10 . The aryl in arylalkoxy Sub 10 includes at least one of aryl Sub1 and heteroaryl Sub2.

[1463] The arylalkoxy Sub 10 in the present specification 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 can be cited as an example.

[1464] The substituted amino group in the present 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 .

[1465] 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 are V1 the same or different.

[1466] 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 are V2 the same or different.

[1467] The alkenyl group in the present 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.

[1468] The alkynyl group in this specification is, for example, alkynyl Sub 13 , alkynyl Sub 13 can be either straight-chain or branched-chain, and is, for example, at least any one group selected from the group consisting of ethynyl, propynyl, and 2-phenylethynyl.

[1469] The alkylthio group in this specification is, for example, alkylthio Sub 14 .

[1470] 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.

[1471] The arylthio group in this specification is, for example, arylthio Sub 15 .

[1472] 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.

[1473] 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.

[1474] The substituted phosphino group in this specification is, for example, substituted phosphino Sub 16 , substituted phosphino Sub 16 is, for example, phenylphosphino.

[1475] 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.

[1476] 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.

[1477] The substituted phosphoryl group in this specification is, for example, the substituted phosphoryl group Sub 19 , the substituted phosphoryl group Sub 19 is represented by the following general formula (P).

[1478]

Chemical Formula 208

[1479]

[1480] In the general formula (P), Ar P1 and Ar P2 are each a substituent selected from the group consisting of the above-mentioned alkyl Sub3 and the above-mentioned aryl Sub1.

[1481] The ester group in this specification is, for example, the ester group Sub 20 , the ester group Sub 20 is at least one group selected from the group consisting of an alkyl ester group and an aryl ester group, for example.

[1482] The alkyl ester group in this specification is, for example, the 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-mentioned substituted or unsubstituted alkyl Sub3 (preferably having 1 to 10 carbon atoms).

[1483] The aryl ester group in this specification is, for example, the 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-mentioned substituted or unsubstituted aryl Sub1.

[1484] The siloxanyl group in this specification is, for example, the 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, a trimethylsiloxanyl group.

[1485] The carbamoyl group in this specification is represented as -CONH2.

[1486] The substituted carbamoyl group in this specification is, for example, the 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.

[1487] R C For example, it is the above-mentioned substituted or unsubstituted alkyl Sub3 (preferably having 1 to 6 carbon atoms).

[1488] 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).

[1489] In addition, in this specification, a hydrogen atom includes isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[1490] 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.

[1491] Similarly, substituted silyl Sub5 refers to any one or more groups among alkylsilyl Sub 51 and arylsilyl Sub 52 among them.

[1492] Similarly, substituted amino Sub 11 refers to any one or more groups among arylamino Sub 111 and alkylamino Sub 112 among them.

[1493] 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, aryloxyalkyl 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.

[1494] In this specification, in the case of "substituted or unsubstituted", the substituent R F1 can also be diarylboron group (Ar B1 Ar B2 B-). As an example of this Ar B1 and Ar B2 , the above-mentioned aryl Sub1 can be cited. Ar B1 Ar B2 in Ar B1 B- and Ar B2 are the same or different.

[1495] 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, 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 and carbamoyl Sub 22 ) can be cited.

[1496] In the case of "substituted or unsubstituted", the substituent R F1may 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, these multiple substituents R F2 may also bond to each other to form a ring.

[1497] In the case of "substituted or unsubstituted", "unsubstituted" means not substituted by the substituent R F1 and bonded to a hydrogen atom.

[1498] 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.

[1499] 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.

[1500] In the compounds or their partial structures described in this specification, in the case of "substituted or unsubstituted", it is the same as described above.

[1501] 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.

[1502] In this specification, as the aromatic hydrocarbon group in the linking group, for example, a divalent or higher group obtained by removing one or more atoms from the above-mentioned monovalent aryl group Sub1 can be exemplified.

[1503] In this specification, as the heterocyclic group in the linking group, for example, a divalent or higher group obtained by removing one or more atoms from the above-mentioned monovalent heteroaryl group Sub2 can be exemplified.

[1504]

Examples

[1505] <Compound>

[1506] The structure of the compound represented by the general formula (3) used for the production of the organic EL elements in Examples 1 to 4 is shown below.

[1507]

Chemical Formula 209

[1508]

[1509]

Chemical Formula 210

[1510]

[1511] The structure of the comparative compound used for the production of the organic EL elements in Comparative Examples 1 to 3 is shown below.

[1512]

Chemical Formula 211

[1513]

[1514] The structure of the other compounds used for the production of the organic EL elements in Examples 1 to 4 and Comparative Examples 1 to 3 is shown below.

[1515]

Chemical Formula 212

[1516]

[1517]

Chemical Formula 213

[1518]

[1519]

Chemical Formula 214

[1520]

[1521]

Chemical Formula 215

[1522]

[1523]

Chemical Formula 216

[1524]

[1525] <Fabrication of Organic EL Element>

[1526] An organic EL element was fabricated and evaluated as described below.

[1527] 〔Example 1〕

[1528] A glass substrate (manufactured by Gio Ma Technology Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then UV ozone washed for 1 minute. The film thickness of ITO was set to 130 nm.

[1529] The washed glass substrate with the transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus, and compound HT and compound HA were co-evaporated in such a manner as to cover the transparent electrode on the surface on the side where the transparent electrode line was 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.

[1530] Next, compound HT was evaporated on the hole injection layer to form a hole transport layer with a film thickness of 200 nm.

[1531] Next, compound EBL was evaporated on the hole transport layer to form an electron blocking layer with a film thickness of 10 nm.

[1532] Next, compound M3a as compound M3, compound TADF as compound M2, and compound RD as compound M1 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 M3a in the light-emitting layer was set to 74% by mass, the concentration of compound TADF was set to 25% by mass, and the concentration of compound RD was set to 1% by mass.

[1533] Next, compound HBL was evaporated on the light-emitting layer to form a hole blocking layer with a film thickness of 10 nm.

[1534] Next, compound ET was evaporated on the hole blocking layer to form an electron transport layer with a film thickness of 30 nm.

[1535] 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.

[1536] Then, metallic aluminum (Al) was evaporated on the electron injection electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1537] If the element configuration of the organic EL element of Example 1 is schematically shown, it is as follows.

[1538] ITO(130) / HT: HA(10, 97%:3%) / HT(200) / EBL(10) / M3a: TADF: RD(25, 74%:25%:1%) / HBL(10) / ET(30) / LiF(1) / Al(80)

[1539] In addition, the numbers in parentheses represent the film thickness (unit: nm).

[1540] 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 compound M3a, compound TADF, and compound RD in the light-emitting layer. The following markings are also made in the same way.

[1541] [Comparative Example 1]

[1542] A comparative example 1 organic EL element was fabricated in the same manner as in Example 1, except that compound M3a in the light-emitting layer of the organic EL element in Example 1 was changed to the compound described in Table 1.

[1543] <Evaluation of Organic EL Element>

[1544] The following evaluations were performed on the organic EL elements fabricated in Examples 1 to 4 and Comparative Examples 1 to 3. The evaluation results are shown in Table 1 or Table 2. In addition, for convenience, the comparative compound Ref-1 used in Comparative Example 1 and Comparative Example 2 and the comparative compound Ref-2 used in Comparative Example 3 are described in the column of compound M3.

[1545] ·Peak wavelength (λp)

[1546] The spectro-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 The peak wavelength λp (unit: nm) was determined from the obtained spectro-emission luminance spectrum.

[1547] ·Drive voltage

[1548] 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

[1549] ·External quantum efficiency EQE

[1550] The spectro-emission luminance 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 ​The spectral emission luminance spectrum at that time. Based on the obtained spectral emission luminance spectrum, assuming Lambertian emission, the external quantum efficiency EQE (unit: %) was calculated.

[1551]

Table 1

[1552]

[1553] In Table 1 and Table 2 above, S1 [eV] represents the physical property value of the compound used in the light-emitting layer of each example and comparative example. For example, in Example 1, S1 of compound M3a is 3.42 eV, and S1 of compound TADF is 2.38 eV.

[1554] In addition, Ref-1 in Comparative Example 1 does not conform to the general formula of compound M3, but for convenience, it is marked in the same column as M3a in Example 1 in the table.

[1555] The organic EL element of Example 1 emits light with high efficiency compared to the organic EL element of Comparative Example 1.

[1556] <Fabrication of Organic EL Element>

[1557] 〔Example 2〕

[1558] 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 washed in isopropyl alcohol for 5 minutes and then UV-ozone washed for 1 minute. The film thickness of ITO was set to 130 nm.

[1559] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus, and compound HT and compound HA were co-evaporated in such a way as to cover the transparent electrode on the surface on the side where the transparent electrode lines were formed, 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.

[1560] Next, compound HT was evaporated on the hole injection layer to form a hole transport layer with a film thickness of 200 nm.

[1561] Next, compound EBL-2 was evaporated on this hole transport layer to form an electron blocking layer with a film thickness of 10 nm.

[1562] Next, co-evaporation of compound M3a as compound M3, compound TADF-2 as compound M2, and compound RD as compound M1 was performed on the electron blocking layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of compound M3a in the light-emitting layer was set to 74% by mass, the concentration of compound TADF-2 was set to 25% by mass, and the concentration of compound RD was set to 1% by mass.

[1563] Next, compound HBL was evaporated on the light-emitting layer to form a hole blocking layer with a film thickness of 10 nm.

[1564] Next, compound ET was evaporated on the hole blocking layer to form an electron transport layer with a film thickness of 30 nm.

[1565] Next, lithium fluoride (LiF) was evaporated on the electron transport layer to form an electron-injecting electrode (cathode) with a film thickness of 1 nm.

[1566] Then, metallic aluminum (Al) was evaporated on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1567] If the element configuration of the organic EL element of Example 1 is schematically shown, it is as follows.

[1568] ITO(130) / HT:HA(10, 97%:3%) / HT(200) / EBL-2(10) / M3a:TADF-2:RD(25, 74%:25%:1%) / HBL(10) / ET(30) / LiF(1) / Al(80)

[1569] In addition, the numbers in parentheses represent the film thickness (unit: nm).

[1570] Within the same parentheses, the numbers represented by percentages (97%:3%) show the ratio (mass%) of compound HT and compound HA in the hole injection layer, and the numbers represented by percentages (74%:25%:1%) show the ratio (mass%) of compound M3a, compound TADF-2, and compound RD in the light-emitting layer. The same labeling is performed hereinafter.

[1571] 〔Example 3 and Example 4〕

[1572] Except that the compound M3a in the light-emitting layer of the organic EL element of Example 2 was changed to the compound described in Table 2, the organic EL elements of Example 3 and Example 4 were produced in the same manner as in Example 2, respectively.

[1573] 〔Comparative Example 2 and Comparative Example 3〕

[1574] An organic EL element of Comparative Example 2 and an organic EL element of Comparative Example 3 were fabricated in the same manner as in Example 2, except that Compound M3a in the light-emitting layer of the organic EL element of Example 2 was changed to the compound described in Table 2.

[1575] <Evaluation of Organic EL Element>

[1576] The external quantum efficiency EQE and the main peak wavelength λp of the fabricated organic EL element were evaluated by the same method as described above. The evaluation results are shown in Table 2.

[1577]

Table 2

[1578]

[1579] In addition, Ref-1 of Comparative Example 2 and Ref-2 of Comparative Example 3 do not conform to the general formula of Compound M3, but for convenience, they are marked in the same column as Compound M3 of Examples 2 to 4 in the table.

[1580] The organic EL elements of Examples 2 to 4 emit light with high efficiency as compared with the organic EL elements of Comparative Examples 2 to 3.

[1581] <Evaluation of Compound>

[1582] The physical property values of the compounds used in Examples 1 to 4 and Comparative Examples 1 to 3 were measured by the following method.

[1583] (Delayed Fluorescence Property)

[1584] · Delayed fluorescence property of Compound TADF

[1585] The delayed fluorescence property was confirmed by measuring transient PL using the apparatus shown in Figure 2 . The Compound TADF was dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength was prepared in order to eliminate the influence of self-absorption. In addition, in order to prevent quenching caused by oxygen, the sample solution was frozen and degassed, and then sealed in a capped cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[1586] The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated by equation (1) in Morris et al., 《J. Phys. Chem.》, 80 (1976) 969.

[1587] After being excited by pulsed light (light irradiated by a pulsed laser) having a wavelength absorbed by the compound TADF, there are Prompt luminescence (instantaneous luminescence) immediately observable from this excited state and Delay luminescence (delayed luminescence) not immediately observable after this excitation but observable thereafter. The delayed fluorescence luminescence in this embodiment means that the amount of Delay luminescence (delayed luminescence) is 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.

[1588] The amounts of Prompt luminescence and Delay luminescence and their ratio can be determined by the same method as the method described in "Nature 492, 234 - 238, 2012" (Reference 1). In addition, the devices for calculating the amounts of Prompt luminescence and Delay luminescence are not limited to the devices described in the said Reference 1 or Figure 2 the devices described in

[1589] For the compound TADF, it was confirmed that the amount of Delay luminescence (delayed luminescence) is 5% or more relative to the amount of Prompt luminescence (instantaneous luminescence).

[1590] Furthermore, as a result of performing the same measurement on the compound TADF - 2 as on the compound TADF, it was also confirmed that the amount of Delay luminescence (delayed luminescence) of the compound TADF - 2 is 5% or more relative to the amount of Prompt luminescence (instantaneous luminescence).

[1591] Specifically, for the compounds TADF and TADF - 2, the value of X D / X P is 0.05 or more for both.

[1592] (Singlet energy S1)

[1593] The singlet energy S1 of the compounds M3a, M3b, M3d, TADF, TADF - 2, RD, comparative compound Ref - 1, and comparative compound Ref - 2 was measured by the above solution method. The measurement results are shown in Table 1 or Table 2.

[1594] Furthermore, as a result of similarly measuring the singlet energies of the compounds M3c and M3e in the synthesis examples described later, they were 3.35 eV and 3.46 eV respectively.

[1595] (Energy gap at 77 [K])

[1596] The energy gap T of the compound TADF and the compound TADF-2 at 77[K] was measured by the above method. 77K .

[1597] (△ST)

[1598] Based on the measured singlet energy S1 and energy gap T at 77[K] 77K ΔST was calculated. It was confirmed that ΔST of both the compound TADF and the compound TADF-2 was less than 0.01.

[1599] [Synthesis Example 1: Synthesis of Compound M3a]

[1600] (1-1) Synthesis of Compound M3a

[1601] The synthesis scheme of compound M3a is shown below.

[1602]

Chemistry 217

[1603]

[1604] 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 M3a (51.5 g, yield 87%). It was identified as compound M3a by LC-MS (Liquid Chromatography Mass Spectrometry) analysis.

[1605] [Synthesis Example 2: Synthesis of Compound M3b]

[1606] (1-2) Synthesis of Compound M3b

[1607] The synthesis scheme of compound M3b is shown below.

[1608]

Chemistry 218

[1609]

[1610] Under nitrogen atmosphere, xylene (650 mL) was added to a mixture of 7H-benzofuran [2,3-b] carbazole (25.8 g, 100 mmol), 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H-carbazole (40.0 g, 100 mmol), tri (dibenzylideneacetone) dipalladium (1.83 g, 2.00 mmol), tri-tert-butylphosphine tetrafluoroborate (1.16 g, 4.00 mmol) and sodium tert-butoxide (11.5 g, 120 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 M3b (45.7 g, yield 79%). It was identified as compound M3b by LC-MS (Liquid Chromatography Mass Spectrometry) analysis.

[1611] [Synthesis Example 3: Synthesis of Compound M3c]

[1612] (1-3) Synthesis of Compound M3c

[1613] The synthesis scheme of compound M3c is shown below.

[1614]

化219

[1615]

[1616] Under nitrogen atmosphere, xylene (650 mL) was added to a mixture of 12H-[1]benzothieno[2,3-a]carbazole (27.3 g, 100 mmol), 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole (40.0 g, 100 mmol), tri(dibenzylideneacetone)dipalladium (1.83 g, 2.00 mmol), tri-tert-butylphosphine tetrafluoroborate (1.16 g, 4.00 mmol) and sodium tert-butoxide (11.5 g, 120 mmol), and the mixture was 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 M3c (42.5 g, yield 72%). It was identified as compound M3c by LC-MS (Liquid Chromatography Mass Spectrometry) analysis.

[1617] [Synthesis Example 4: Synthesis of Compound M3d]

[1618] (1-4) Synthesis of Compound M3e

[1619] The synthesis scheme of compound M3e is shown below.

[1620]

Chemistry 220

[1621]

[1622] Except in Synthesis Example 1 where 9-(3’-bromo-[1,1’-biphenyl]-3-yl)-9H-carbazole was used to replace 9-(4’-bromo-[1,1’-biphenyl]-4-yl)-9H-carbazole, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain Compound M3e. The yield was 63%. It was identified as Compound M3e by analysis using LC-MS (Liquid Chromatography Mass Spectrometry).

[1623] Description of Reference Numerals

[1624] 1 Organic EL element

[1625] 2 Substrate

[1626] 3 Anode

[1627] 4 Cathode

[1628] 5 Light-emitting layer

[1629] 6 Hole injection layer

[1630] 7 Hole transport layer

[1631] 8 Electron transport layer

[1632] 9 Electron injection layer.

Claims

1. An organic electroluminescent element, characterized in that, having: an anode; a cathode; a light-emitting layer, disposed between the anode and the cathode, the light-emitting layer including a compound M2 having delayed fluorescence and a compound M3 represented by the following general formula (3), the singlet energy S1(M2) of the compound M2 and the singlet energy S1(M3) of the compound M3 satisfy the relationship of the following mathematical formula (Equation 1), S1(M3) > S1(M2)…(Equation 1), In the general formula (3), A 30 is a group represented by the following general formula (3a), general formula (3b), general formula (3c), general formula (3d), general formula (3e) or general formula (3f), in the general formula (3a), general formula (3b), general formula (3c), general formula (3d), general formula (3e), and general formula (3f), X 31 , X 32 , X 33 , X 34 , X 35 and X 36 are each independently an oxygen atom R 310 ~R 319 are each independently a hydrogen atom, R 320 ~R 329 each independently represents a hydrogen atom, R 330 ~R 339 each independently represents a hydrogen atom, R 340 ~R 349 each independently represents a hydrogen atom, R 350 ~R 359 each independently represents a hydrogen atom, R 360 ~R 369 each independently represents a hydrogen atom *Indicates the bonding position with L 30 and in the general formula (3), L 30 is an unsubstituted arylene group having 6 to 22 ring carbon atoms, a group formed by bonding two unsubstituted arylene groups having 6 to 22 ring carbon atoms, or a group formed by bonding three unsubstituted arylene groups having 6 to 22 ring carbon atoms, R 31 ~R 38 Each is independently a hydrogen atom.

2. The organic electroluminescent element according to claim 1, characterized in that the light-emitting layer further includes a fluorescent compound M1, the singlet energy S1(M2) of the compound M2 and the singlet energy S1(M1) of the compound M1 satisfy the relationship of the following mathematical formula (Equation 2), S1(M2) > S1(M1)…(Equation 2).

3. The organic electroluminescent element according to claim 1 or 2, characterized in that L 30 For an unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted terphenylene group.

4. The organic electroluminescent element according to claim 1 or 2, characterized in that L 30 is an unsubstituted biphenylene group.

5. The organic electroluminescent element according to claim 1 or 2, characterized in that L 30 is at least any one group selected from the group consisting of groups represented by the following general formulas (L30-1) to (L30-4), (L30-4-2), (L30-5) to (L30-11): In the general formulas (L30-1) to (L30-4), (L30-4-2), (L30-5) to (L30-11), Q1 to Q 14 are each independently a hydrogen atom.

6. The organic electroluminescent element according to claim 1 or 2, characterized in that A 30 is a group represented by the general formula (3a) or the general formula (3d).

7. The organic electroluminescent element according to claim 1 or 2, characterized in that A 30 is a group represented by the general formula (3a).

8. The organic electroluminescent element according to claim 1 or 2, characterized in that the compound M3 is a compound that does not exhibit thermally activated delayed fluorescence.

9. The organic electroluminescent element according to claim 1 or 2, characterized in that A 10 μmol / L toluene solution of the compound to be measured is prepared as a sample in a quartz cell, and the absorption spectrum of the sample is measured at 300 K. The vertical axis of the absorption spectrum is set as the absorption intensity, and the horizontal axis is set as the wavelength. A tangent line is drawn for the descending edge on the long wavelength side of the absorption spectrum, and the wavelength value λedge [nm] of the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy, Conversion formula (F2): S1 [eV] = 1239.85 / λedge.

10. The organic electroluminescent element according to claim 1 or 2, characterized in that The energy gap T of the compound M3 at 77 [K] 77K (M3) and the energy gap T of the compound M2 at 77 [K] 77K (M2) satisfies the relationship of the following mathematical formula (Formula 11). T 77K (M3) > T 77K (M2)…(Number 11).

11. The organic electroluminescent element according to claim 10, characterized in that Dissolve the compound to be measured in EPA at a concentration of 10 μmol / L. The volume ratio of this EPA is diethyl ether:isopentane:ethanol = 5:5:

2. Put this solution into a quartz cell as the measurement sample. For this measurement sample, measure the phosphorescence spectrum at 77 [K]. Set the vertical axis of this phosphorescence spectrum as the phosphorescence emission intensity and the horizontal axis as the wavelength. Make 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, take 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 .

12. The organic electroluminescent element according to claim 1 or 2, characterized in that when the organic EL element emits light, in the light-emitting layer, the compound M3 does not emit light.

13. The organic electroluminescent element according to claim 1, characterized in that the content of the compound M3 in the light-emitting layer is 20% by mass or more and 90% by mass or less.

14. The organic electroluminescent element according to claim 1 or 13, characterized in that the content rate of the compound M3 in the light-emitting layer is 40% by mass or more and 90% by mass or less.

15. The organic electroluminescent element according to claim 1 or 13, characterized in that the content rate of the compound M3 in the light-emitting layer is 40% by mass or more and 80% by mass or less.

16. The organic electroluminescent element according to claim 2, characterized in that the content rate of the compound M3 in the light-emitting layer is 10% by mass or more and 80% by mass or less.

17. The organic electroluminescent element according to claim 1 or 2, characterized in that the light-emitting layer contains only one kind of the compound M3.

18. The organic electroluminescent element according to claim 1 or 2, characterized in that the light-emitting layer contains two or more kinds of the compound M3.

19. The organic electroluminescent element according to claim 1 or 2, characterized in that the light-emitting layer contains the following compound M3b as the compound M3.

20. The organic electroluminescent element according to claim 1 or 2, characterized in that the light-emitting layer contains the following compound M3a as the compound M3.

21. An electronic device, characterized in that, An organic electroluminescent element according to any one of claims 1 to 20 is mounted.

22. A compound, characterized in that, It is represented by the following general formula (301), In the general formula (301), 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), 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 each independently represents a hydrogen atom R 320 ~R 329 each independently represents a hydrogen atom R 330 ~R 339 each independently represents a hydrogen atom R 340 ~R 349 each independently represents a hydrogen atom R 350 ~R 359 each independently represents a hydrogen atom R 360 ~R 369 each independently represents a hydrogen atom * indicates the bonding position of the benzene ring bonded to R 401 ~R 404 to the bonding position of the benzene ring, In the general formula (301), R 31 ~R 38 each independently represents a hydrogen atom, R 401 ~R 412 each independently represents a hydrogen atom n is 0, 1, 2, or 3.

23. The compound according to claim 22, characterized in that n is 0 or 1.

24. The compound according to claim 22 or 23, characterized in that, It is represented by the following general formula (302), A in the general formula (302) 31 , R 401 ~R 404 , R 409 ~R 412 , R 31 ~R 38 are respectively synonymous with A in the general formula (301) 31 , R 401 ~R 404 , R 409 ~R 412 , R 31 ~R 38 .

25. The compound according to claim 22 or 23, characterized in that A 31 is a group represented by the general formula (31a) or the general formula (31d).

26. The compound according to claim 22 or 23, characterized in that It is represented by the following general formula (303), R in the general formula (303) 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 、R 310 ~R 319 are respectively synonymous with R 401 ~R 404 、R 409 ~R 412 、R 31 ~R 38 、R 310 ~R 319 in the general formula (301).

27. The compound according to claim 24, characterized in that The compound represented by the general formula (302) is the following compound M3b.

28. The compound according to claim 26, characterized in that The compound represented by the general formula (303) is the following compound M3a.

29. An organic electroluminescent element, characterized in that, It has: an anode; a cathode; a light-emitting layer, which is included between the anode and the cathode, the light-emitting layer contains a delayed fluorescence compound M2 and the compound according to any one of claims 22 to 28.

30. An electronic device, characterized in that, An organic electroluminescent element according to claim 29 is mounted.

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