Organic light-emitting elements, compounds, materials for organic light-emitting elements, and electronic devices

Abstract

This invention relates to an organic EL element having an anode, a cathode, and a light-emitting layer contained between the anode and the cathode. The light-emitting layer comprises a delayed-fluorescence compound M2 and a compound M3 represented by general formula (100), wherein the singlet state energy S1(M2) of compound M2 and the singlet state energy S1(M3) of compound M3 satisfy the mathematical relationship (Formula 1). In general formula (100), X1 is an oxygen atom or a sulfur atom, C1 is a carbon atom, and R... 11 ~R 18 R2, R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 Each can be an independent hydrogen atom or substituent, etc., with n being 1, 2, or 3. Where L1 is a single bond, n is 1, k is 1, 2, or 3, m is 2, 3, or 4, k+m=5, and L1 is a single bond or a linking group. S1(M3) > S1(M2) (number 1)

Description

[0001] This invention application is a divisional application filed in China based on the international application filed by Idemitsu Kosan Co., Ltd., under the PCT application number PCT / JP2019 / 048468, entitled "Organic electroluminescent element, compound, material for organic electroluminescent element and electronic device", which has entered the national phase in China. The application number of the Chinese invention application is 201980081332.8, and the application date is December 11, 2019. Technical Field

[0002] This invention relates to organic electroluminescent elements, compounds, materials for organic electroluminescent elements, and electronic devices. Background Technology

[0003] When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, while electrons are injected from the cathode. Then, in the light-emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical theorem of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons at a rate of 75%.

[0004] Fluorescent organic EL devices, which emit light from singlet excitons, are being used in full-color displays for mobile phones and televisions, but an internal quantum efficiency of 25% is considered the limit. Therefore, research is underway to improve the performance of organic EL devices.

[0005] Furthermore, it is hoped that triplet excitons, in addition to singlet excitons, can be utilized to make organic EL devices emit light more efficiently. Against this background, a highly efficient fluorescent organic EL device utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") is proposed and investigated.

[0006] For example, the mechanism of TADF (Thermally Activated Delayed Fluorescence) has been studied. This TADF mechanism utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under thermal action, occurring when using materials with a small energy difference (ΔST) between singlet and triplet energy levels. For example, information on thermally activated delayed fluorescence is described in "Adachi Chiba-ed, *Device Properties of Organic Semiconductors*, Kodansha, April 1, 2012, pp. 261-268".

[0007] Non-Patent Document 1 discloses an organic light-emitting diode comprising an organic light-emitting layer containing a TADF compound as an auxiliary dopant, mCP (1,3-bis(N-carbazolyl)benzene), mCBP (3,3'-bis(9H-carbazol-9-yl)biphenyl) or CPB (4,4'-bis(9-carbazolyl)-1,1'-biphenyl) as a host material and a fluorescent light-emitting material.

[0008] Patent Document 1 discloses an organic EL device having a light-emitting layer comprising an auxiliary dopant, a host material, and a fluorescent dopant. As an auxiliary dopant, a compound obtained by bonding a triazine ring and a fused carbazole ring via a phenylene ring is disclosed.

[0009] In Patent Document 2, as a material for organic EL elements used in conjunction with phosphorescent metal complexes, a compound having a structure in which an aryl group is bonded to a dibenzothiophene ring or a dibenzofuran ring is disclosed.

[0010] Existing technical documents Patent documents Patent Document 1: U.S. Patent Application Publication No. 2017 / 0062718 Patent Document 2: International Publication No. 2009 / 008099 Non-patent literature Non-patent literature 1: Hajime Nakanotani et al., “High-efficiency organic light-emitting diodes with fluorescent emitters”, Nature Communications, 5, 4016, 2014 Summary of the Invention The technical problem that the invention aims to solve In organic EL devices that utilize the TADF mechanism, further performance improvements are required, such as longer lifetime.

[0011] To achieve further high performance of the organic EL element, it is important to select the molecular structure of the material used in conjunction with the TADF compound.

[0012] The purpose of this invention is to provide a high-performance organic EL element, such as an organic EL element capable of emitting light with a long lifespan, and an electronic device equipped with the organic EL element.

[0013] Furthermore, the present invention aims to provide a compound for an organic EL element capable of achieving high performance, such as an organic EL element with long lifespan emission and an electronic device, and a material for an organic EL element containing the compound.

[0014] Solution to the above technical problems According to one aspect of the present invention, an organic electroluminescent element is provided, comprising: anode; cathode; A light-emitting layer is contained between the anode and the cathode. The luminescent layer comprises a delayed-fluorescence compound M2 and a compound M3 represented by the following general formula (100). The singlet energy S1(M2) of compound M2 and the singlet energy S1(M3) of compound M3 satisfy the following mathematical expression (number 1).

[0015] S1(M3) > S1(M2) (Number 1)

Chemistry 1

[0016] In the general formula (100), X1 is an oxygen atom or a sulfur atom, and C1 is a carbon atom. n is 1, 2, or 3. k is 1, 2, or 3. m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups, either substituted or unsubstituted, having a cyclic carbon number of 6 to 30. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (100), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R4 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The ring is formed by bonding one or more groups from a group of R4s together, or by bonding two or more groups from a plurality of R4s together, wherein the three R4s are the same or different from each other, and the three R4s are bonded to carbon atoms at any position of f, g, h and i as shown in the general formula (100), and C1 is bonded to carbon atoms at any position of f, g, h and i that are not bonded to the R4s. R as a substituent 11 ~R 18 R2, R31 R 32 R 34 R 35 R4 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0017] According to one aspect of the present invention, an electronic device is provided, which is equipped with an organic electroluminescent element according to one aspect of the present invention described above.

[0018] According to one aspect of the invention, compounds represented by the following general formula (201), the following general formula (202), or the following general formula (203) can be provided.

[0019]

Chemistry 2

[0020]

Transformation 3

[0021]

Chemistry 4

[0022] In the general formulas (201) to (203), X1 is an oxygen atom or a sulfur atom. n is 1, 2, or 3. k is 1, 2, or 3. m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and multiple R groups are such that at least one of n and k is 2 or more. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R 41 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 and R 41 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms in the cyclic formation. Among them, R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0023] According to one aspect of the invention, a compound represented by the following general formula (300) can be provided.

[0024]

Transformation 5

[0025] In the general formula (300), X1 is an oxygen atom or a sulfur atom. n is 1, 2, or 3. k is 1, 2, or 3. m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (300), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (300), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (300), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R 41 R 42 R 43 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0026] According to one aspect of the invention, compounds represented by any one of the following general formulas (501) to (514) can be provided.

[0027]

Transformation 6

[0028]

Transformation 7

[0029] According to one aspect of the present invention, a material for an organic electroluminescent device comprising the compound described above is provided.

[0030] According to one aspect of the present invention, it is possible to provide a high-performance organic EL element, such as an organic EL element capable of emitting light with a long lifespan, and an electronic device equipped with the organic EL element.

[0031] According to one aspect of the present invention, it is possible to provide a compound for an organic EL element capable of achieving high performance, such as an organic EL element with long lifespan light emission and an electronic device, and a material for an organic EL element containing the compound. Attached Figure Description

[0032] Figure 1 This is a diagram illustrating a schematic configuration of an example of an organic electroluminescent element according to a first embodiment of the present invention.

[0033] Figure 2 This is a schematic diagram of a device for measuring transient pulse (PL).

[0034] Figure 3 This is a graph showing an example of the decay curve of the transition PL.

[0035] Figure 4 This is a diagram showing the relationship between the energy levels and energy transfer of compounds M3 and M2 in the light-emitting layer of an example of an organic electroluminescent element according to a first embodiment of the present invention.

[0036] Figure 5 This is a diagram showing the relationship between the energy levels and energy transfer of compounds M3, M2, and M1 in the light-emitting layer of an example of an organic electroluminescent element according to a second embodiment of the present invention. Detailed Implementation

[0037] [First Implementation] The structure of the organic EL element according to the first embodiment of the present invention will be described.

[0038] An organic EL element has an organic layer between its two electrodes, an anode and a cathode. This organic layer comprises at least one layer made of an organic compound. Alternatively, the organic layer may be composed of multiple layers of organic compounds stacked together. The organic layer may also contain inorganic compounds. In the organic EL element of this embodiment, at least one layer of the organic layer is a light-emitting layer. Therefore, the organic layer may, for example, consist of a single light-emitting layer, or it may contain layers that can be used in an organic EL element. There is no particular limitation on the layers that can be used in an organic EL element; for example, at least any 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.

[0039] The organic EL element of this embodiment has a light-emitting layer contained between the anode and the cathode.

[0040] Figure 1 The diagram shows a schematic configuration of an example of an organic EL element in this embodiment.

[0041] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is composed of a 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 sequentially stacked from the anode 3 side.

[0042] The luminescent layer 5 may also contain a metal complex.

[0043] The light-emitting layer 5 is preferably free of phosphorescent materials (dopants).

[0044] The light-emitting layer 5 is preferably a rare-earth metal complex that does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0045] Furthermore, the light-emitting layer 5 is preferably free of metal complexes.

[0046] In the organic EL element 1 of this embodiment, the light-emitting layer 5 includes a delayed fluorescence compound M2 and a compound M3 represented by the general formula (100).

[0047] In this scheme, compound M2 is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material), and compound M3 is preferably a host material (sometimes also called a matrix material).

[0048] Compound M3 can be a compound with delayed fluorescence or a compound without delayed fluorescence.

[0049] The inventors have discovered that by using compound M3, represented by the general formula (100), together with compound M2, which exhibits delayed fluorescence, a high-performance organic EL element can be achieved.

[0050] Compound M3 has a structure in which the carbon atom at the 4-position or the carbon atom at the 4'-position of the dibenzofuran ring or the dibenzothiophene ring, which serves as the electron transport site, is substituted with, for example, a carbon atom at the 3-position or the carbon atom at the 3'-position of the dibenzofuran ring or the dibenzothiophene ring. Therefore, compared with compounds having a structure in which the carbon atom at the 3-position or the carbon atom at the 3'-position of the dibenzofuran ring or the dibenzothiophene ring, for example, is substituted with a carbon atom at the 3-position or the carbon atom at the 3'-position of the electron transport site, the conjugation length of compound M3 in this embodiment is extended.

[0051] In this embodiment, it can be considered that by including compound M3, which elongates the conjugate length of the electron transport site in the luminescent layer, electrons can be transported into the interior of the luminescent layer, thereby expanding the electron-hole recombination region. This can be considered a result of reducing the load on the luminescent layer. Typically, in most cases, to reduce ΔST, delayed fluorescence compounds are introduced into the molecule at sites with a large absolute value of LUMO (lowest unoccupied molecular orbital). However, if the luminescent layer contains a delayed fluorescence compound with this portion introduced, it can sometimes hinder the electron transport properties of the luminescent layer.

[0052] In this embodiment, it can be considered that since compound M3, which elongates the conjugate length of the electron transport site, and compound M2, which has delayed fluorescence, are both contained in the luminescent layer, the electron transport of the luminescent layer can be suppressed, and as a result, the degree of reduction in the load of the luminescent layer can be increased.

[0053] Furthermore, it can be argued that the conjugate length elongation of compound M3 in the electron transport region can also reduce the load in the compound's own electron transport.

[0054] Furthermore, in the local structure represented by the general formula (X), compound M3 has a carbazole ring bonded via a single bond or a linking group as a hole injection site, thus having a structure capable of injecting an appropriate amount of holes into the light-emitting layer.

[0055] Therefore, according to this embodiment, high-performance organic EL devices can be realized.

[0056] In this embodiment, "high performance" refers to at least one of long-life emission, improved luminous efficiency, reduced driving voltage, and increased brightness.

[0057] The structure of the organic EL element of this embodiment will be described in detail below. Reference numerals will be omitted from the accompanying drawings below.

[0058] <Emitting Layer> (Compound M3) The light-emitting layer of this embodiment contains compound M3 represented by the following general formula (100).

[0059] In this embodiment, compound M3 can be a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence, and preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0060]

Transformation 8

[0061] In the general formula (100), X1 is an oxygen atom or a sulfur atom, and C1 is a carbon atom. m is 1, 2, or 3, and k is 1, 2, or 3. m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (100), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R4 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The ring is formed by bonding one or more groups from a group of R4s together, or by bonding two or more groups from a plurality of R4s together, wherein the three R4s are the same or different from each other, and the three R4s are bonded to carbon atoms at any position of f, g, h and i as shown in the general formula (100), and C1 is bonded to carbon atoms at any position of f, g, h and i that are not bonded to the R4s. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0062] In general formula (100), the specific bonding modes of R2 and L1 with the carbon atoms at positions a, b, c, d and e shown in general formula (100) are as follows.

[0063] With n = 1, L1 being a divalent linking group, k = 1, and m = 4, the four R2s are bonded to carbon atoms at any of the positions a, b, c, d, and e shown in the general formula (100), and one L1 is bonded to a carbon atom at position a, b, c, d, or e that is not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0064] With n = 1, L1 being a divalent linking group, k = 2, and +m = 3, the three R2s are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0065] When n is 1, L1 is a divalent linking group, k is 3, and m is 2, the two R2s are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the three L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0066] For example, when n is 1, L1 is a divalent linking group, k is 1, and m is 4, the four R2s are bonded to carbon atoms at positions a, b, d, and e as shown in general formula (100), and the bonding mode when one L1 is bonded to carbon atom at position c as shown in general formula (100) is represented by the following general formula (B1).

[0067]

Chemistry 9

[0068] In general formula (B1), R 11 ~R 18 R in the general formula (100) respectively 11 ~R 18 Synonyms, R 21 R 22 R 24 and R 25 Each is independently synonymous with R2 in the general formula (100). In general formula (B1), * indicates that it is located in the general formula (100) relative to R. 32 The carbon atoms of the bonded benzene ring and R 34 The bonding positions between carbon atoms in a bonded benzene ring.

[0069] With n = 2, L1 being a trivalent linker, k = 1, and m = 4, the four R2s are bonded to carbon atoms at any of the positions a, b, c, d, and e shown in the general formula (100), and one L1 is bonded to a carbon atom at position a, b, c, d, or e that is not bonded to the R2. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0070] When n is 2, L1 is a trivalent linker, k is 2, and m is 3, the three R2s are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0071] When n is 2, L1 is a trivalent linker, k is 3, and m is 2, the two R2s are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the three L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0072] For example, when n is 2, L1 is a trivalent linker, k is 1, and m is 4, the four R2s are bonded to carbon atoms at positions a, b, d, and e as shown in general formula (100), and the bonding mode when one L1 is bonded to carbon atom at position c as shown in general formula (100) is represented by the following general formula (B2).

[0073]

Chemistry 10

[0074] In general formula (B2), R 11 ~R 18 R in the general formula (100) respectively 11 ~R 18 Synonyms, R 21 R 22 R 24 and R 25 Each is independently synonymous with R2 in the general formula (100). In general formula (B2), * indicates that it is located in the general formula (100) relative to R. 32 The carbon atoms of the bonded benzene ring and R 34 The bonding positions between carbon atoms in a bonded benzene ring.

[0075] In the general formula (B2), there are 2 Rs 11 Whether they are the same or different, 2 Rs 12 Whether they are the same or different, 2 Rs 13 Whether they are the same or different, 2 Rs 14 Whether they are the same or different, 2 Rs 15 Whether they are the same or different, 2 Rs 16 Whether they are the same or different, 2 Rs 17 Whether they are the same or different, 2 Rs 18 They are the same or different from each other.

[0076] When n is 3, L1 is a tetravalent linker, k is 1, and m is 4, the four R2s are bonded to carbon atoms at any of the positions a, b, c, d, and e shown in the general formula (100), and one L1 is bonded to a carbon atom at position a, b, c, d, or e that is not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0077] When n is 3, L1 is a tetravalent linker, k is 2, and m is 3, the three R2s are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0078] When n is 3, L1 is a tetravalent linker, k is 3, and m is 2, the two R2s are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the three L1s are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2s. Notably, multiple R2s are not bonded to carbon atoms at the same position.

[0079] In general formula (100), the specific bonding modes of R2 and the 9-position nitrogen atom of the carbazole ring shown in general formula (100) with the carbon atoms at positions a, b, c, d and e shown in general formula (100) are as follows.

[0080] With n = 1, L1 being a single bond, k = 1, and m = 4, the four R2 atoms are bonded to carbon atoms at any of the positions a, b, c, d, and e shown in the general formula (100). The nitrogen atom at position 9 of the carbazole ring shown in the general formula (100) is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. Notably, multiple R2 atoms are not bonded to carbon atoms at the same positions.

[0081] When n is 1, L1 is a single bond, k is 2, and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the nitrogen atom at position 9 of the two carbazole rings in the general formula (100) is bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. Notably, multiple R2 atoms are not bonded to carbon atoms at the same position.

[0082] When n is 1, L1 is a single bond, k is 3, and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the nitrogen atom at position 9 of the three carbazole rings in the general formula (100) is bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. However, multiple R2 atoms are not bonded to carbon atoms at the same position.

[0083] For example, when n is 1, L1 is a single bond, k is 1, and m is 4, the four R2 atoms are bonded to the carbon atoms at positions a, b, d, and e as shown in general formula (100), and the bonding mode when the nitrogen atom at position 9 of the carbazole ring shown in general formula (100) is bonded to the carbon atom at position c as shown in general formula (100) is represented by the following general formula (B3).

[0084]

Chemistry 11

[0085] In general formula (B3), R 11 ~R 18 R 21 R 22 R 24 and R 25 Respectively with R in the general formula (B1) 11 ~R 18 R 21 R 22 R 24 and R 25 Synonyms. In general formula (B3), * indicates that it is located in the general formula (100) relative to R. 32 The carbon atoms of the bonded benzene ring and R 34 The bonding positions between carbon atoms in a bonded benzene ring.

[0086] For example, when n is 1, L1 is a single bond, k is 2, and m is 3, the three R2 atoms are bonded to the carbon atoms at positions a, c, and e as shown in general formula (100), and the bonding mode when the nitrogen atom at position 9 of the two carbazole rings shown in general formula (100) is bonded to the carbon atoms at positions b and d as shown in general formula (100) is represented by the following general formula (B4).

[0087]

Chemistry 12

[0088] In general formula (B4), R 11 ~R 18 R in the general formula (B2) respectively 11 ~R 18 Synonyms, R 21 R 23 and R 25 Independently related to R in the general formula (B2) 21 R 22 R 24 and R 25 Synonyms. In general formula (B4), * indicates that it is located in the general formula (100) relative to R. 32 The carbon atoms of the bonded benzene ring and R34 The bonding positions between carbon atoms in a bonded benzene ring.

[0089] A preferred embodiment of compound M3 according to the first embodiment will be described.

[0090] In the following description, when the compound M3 of this embodiment is represented by a general formula, the positions corresponding to a, b, c, d, e, f, g, h, and i shown in the general formula (100) are respectively set as a, b, c, d, e, f, g, h, and i. In each general formula, the description of a, b, c, d, e, f, g, h, and i is sometimes omitted.

[0091] In compound M3 of this embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 A ring is formed by bonding any one or more groups within a group together.

[0092] In compound M3 of this embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in the group are bonded together to form a loop, and R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups, as well as groups consisting of two or more R4s, do not bond with each other.

[0093] In compound M3 of this embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any group in the set can bond with each other to form a ring.

[0094] In compound M3 of this embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any group in the set can bond with each other to form a loop, and R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups, as well as groups consisting of two or more R4s, do not bond with each other.

[0095] In compound M3 of this embodiment, in R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 When any one or more groups in a group are bonded together to form a ring, the ring preferably has a ring structure represented by the following general formula (400).

[0096]

Chemistry 13

[0097] In the general formula (400), Y1 is an oxygen atom or a sulfur atom, R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, where R 401 and R402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may or may not form a ring by bonding with each other.

[0098] In the general formula (100), R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 In the case where two or more groups in a group are bonded together to form a ring structure represented by the general formula (400), the multiple Y1s may be the same or different from each other, and the multiple Rs may be different from each other. 401 Multiple Rs that are the same or different from each other 402 Multiple Rs that are the same or different from each other 403 Multiple Rs that are the same or different from each other 404 They are the same or different from each other.

[0099] In the general formula (100), when at least either n or k is 2 or more, multiple Y1s are the same or different from each other, and multiple Rs... 401 Multiple Rs that are the same or different from each other 402 Multiple Rs that are the same or different from each other 403 Multiple Rs that are the same or different from each other 404 They are the same or different from each other.

[0100] In the ring structure represented by the general formula (400), *1 and *2 represent R in the general formula (100). 11 and R 12 The groups of two carbon atoms bonded separately, R 12 and R 13 The groups of two carbon atoms bonded separately, R 13 and R 14 The groups of two carbon atoms bonded separately, R 15 and R 16 The groups of two carbon atoms bonded separately, R 16 and R 17 The groups of two carbon atoms bonded separately, and R 17 and R 18 Carbon atoms from at least one group of two carbon atoms bonded separately.

[0101] In the general formula (400), R is preferred. 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 The groups do not bond with each other.

[0102] In the general formula (400), Y1 is preferably an oxygen atom.

[0103] In the general formula (400), Y1 is preferably a sulfur atom.

[0104] In compound M3 of this embodiment, for example, R 11 and R 12 group, R 12 and R 13 The group, and R 13 and R 14 When any group of elements in a group is bonded together to form a ring structure represented by the general formula (400), in the general formula (100), R has 11 ~R 18 The ring structure is represented by any one of the following general formulas (400-1) to (400-6).

[0105]

Chemistry 14

[0106] In the general formulas (400-1) to (400-6), Y1 and R 401 ~R 404 respectively with Y1 and R in the general formula (400) 401 ~R 404 Synonyms, R 11 ~R 18 Independently related to R in the general formula (100) 11 ~R 18 Synonyms.

[0107] In the case where L1 in the general formula (100) is a linking group, * indicates the bonding site with L1.

[0108] In the general formula (100), L1 is a single bond, and n is 1, k is 1, and m is 4. * is bonded to the carbon atom at position a, b, c, d, or e that is not bonded to the four R2s.

[0109] In the general formula (100), L1 is a single bond, and n is 1, k is 2, and m is 3. * is bonded to any carbon atom at any position of a, b, c, d, and e that is not bonded to the three R2s.

[0110] In the general formula (100), L1 is a single bond, and n is 1, k is 3, and m is 2. * is bonded to any carbon atom at any position of a, b, c, d, and e that is not bonded to two R2s.

[0111] In the general formulas (400-1) to (400-6), R is preferred. 11 and R 12 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 The groups do not bond with each other.

[0112] In the general formulas (400-1) to (400-6), Y1 is preferably an oxygen atom.

[0113] In the general formulas (400-1) to (400-6), Y1 is preferably a sulfur atom.

[0114] In the general formula (100), for example in R 11 and R 12 group, R 12 and R 13 The group, and R 13 and R 14 In the case where one group of the groups is bonded to each other to form a ring structure represented by the general formula (400), the compound M3 of this embodiment is represented by any one of the following general formulas (401) to (406).

[0115]

Chemistry 15

[0116]

Chemistry 16

[0117] In the general formulas (401) to (406), X1, R4, R 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 R2, L1, R 11 ~R18 m, n, and k are respectively related to X1, R4, R in the general formula (100). 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 R2, L1, R 11 ~R 18 m, n, and k are synonyms; Y1 represents an oxygen or sulfur atom; R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

[0118] In the general formulas (401) to (406), R is preferred. 11 and R 12 group, R 13 and R 14 group, R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 The groups do not bond with each other.

[0119] The compound M3 in this embodiment is preferably represented by any one of the following general formulas (401A) to (406A).

[0120]

Chemistry 17

[0121] [Chemistry 18]

[0122] In the general formulas (401A) to (406A), X1, R4, R 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 L1, R 11 ~R 18 And n is respectively related to X1, R4, R in the general formula (100) 45~R 48 C1, R 31 ~R 32 R 34 ~R 35 L1, R 11 ~R 18 And n is synonymous with R 21 ~R 22 and R 24 ~R 25 Each is independently synonymous with R2 in the general formula (100), Y1 is an oxygen atom or a sulfur atom, and R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

[0123] In the general formulas (401A) to (406A), R is preferred. 11 and R 12 group, R 13 and R 14 group, R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 The groups do not bond with each other.

[0124] The compound M3 in this embodiment is preferably represented by any one of the following general formulas (401B) to (406B).

[0125]

Chemistry 19

[0126]

Chemistry 20

[0127] In the general formulas (401B) to (406B), X1, R 45 ~R 48 R 31 ~R 32 R 34 ~R 35 L1 and R 11 ~R 18respectively with X1 and R in the general formula (100) 45 ~R 48 R 31 ~R 32 R 34 ~R 35 L1 and R 11 ~R 18 Synonyms, R 41 R 42 and R 44 Each is independently synonymous with R4 in the general formula (100), R 21 ~R 22 and R 24 ~R 25 Each is independently synonymous with R2 in the general formula (100), Y1 is an oxygen atom or a sulfur atom, and R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

[0128] In the general formulas (401B) to (406B), R is preferred. 11 and R 12 group, R 13 and R 14 group, R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 The groups do not bond with each other.

[0129] In compound M3 of this embodiment, R is also preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 45 and R 46group, R 46 and R 47 group, R 47 and R 48 Groups, as well as groups consisting of two or more R4s, do not bond with each other.

[0130] In compound M3 of this embodiment, R2 and R are preferred. 31 R 32 R 34 and R 35 It is a hydrogen atom.

[0131] In this embodiment, if compound M3 is a compound represented by any one of the general formulas (401) to (406), (401A) to (406A), and (401B) to (406B), then R2 or R3 is preferred. 21 ~R 22 R 24 ~R 25 R 31 ~R 32 and R 34 ~R 35 It is a hydrogen atom.

[0132] In compound M3 of this embodiment, R2 and R are preferred. 31 R 32 R 34 and R 35 L1 is a hydrogen atom, and L1 is a single bond or a group derived from an unsubstituted aryl group with 6 to 30 unsubstituted cyclic carbon atoms, or a group derived from an unsubstituted heterocyclic group with 5 to 30 unsubstituted cyclic atoms.

[0133] In this embodiment, if compound M3 is a compound represented by any one of the general formulas (401) to (406), (401A) to (406A), and (401B) to (406B), then R2 or R3 is preferred. 21 ~R 22 R 24 ~R 25 R 31 ~R 32 and R 34 ~R 35 L1 is a hydrogen atom, and L1 is a single bond or a group derived from an unsubstituted aryl group with 6 to 30 unsubstituted cyclic carbon atoms, or a group derived from an unsubstituted heterocyclic group with 5 to 30 unsubstituted cyclic atoms.

[0134] The compound M3 in this scheme is specifically represented by the following general formula (100X).

[0135]

Chemistry 21

[0136] In the general formula (100X), X1, R4, R 45 ~R 48 C1, R 11 ~R 18 , n and k are respectively related to X1, R4, R in the general formula (100) 45 ~R 48 C1, R 11 ~R 18 , n, and k are synonyms. L1 is a single bond or a group derived from an unsubstituted aryl group with 6 to 30 unsubstituted cyclic carbon atoms, or a group derived from an unsubstituted heterocyclic group with 5 to 30 unsubstituted cyclic atoms. When L1 is a single bond, n is 1. When k is 2 or higher, multiple L1 values ​​can be the same or different from each other.

[0137] In the general formula (100X), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0138] In compound M3 of this embodiment, n is preferably 1 or 2, and more preferably n is 1.

[0139] In compound M3 of this embodiment, k is preferably 1 or 2.

[0140] In the compound M3 of this embodiment, it is even more preferable that n is 1 or 2 and k is 1 or 2.

[0141] In the compound M3 of this embodiment, it is even more preferable that n is 1 and k is 1 or 2.

[0142] In the compound M3 of this embodiment, it is even more preferable that n is 2 and k is 1 or 2.

[0143] Specifically, the compound M3 of this embodiment when n is 2 is represented by the following general formula (100Y). The compound M3 of this embodiment when n is 1 is represented by the following general formula (100Z).

[0144]

Chemistry 22

[0145] In the general formula (100Y), X1, R4, R 45 ~R 48 C1, R2, R 31 R 32 R 34 R 35 L1, R 11 ~R18 m and k are respectively related to X1, R4, R in the general formula (100) 45 ~R 48 C1, R2, R 31 R 32 R 34 R 35 L1, R 11 ~R 18 m and k are synonyms.

[0146] In the general formula (100Y), k is preferably 1 or 2.

[0147] In the general formula (100Y), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0148]

Chemistry 23

[0149] In the general formula (100Z), X1, R4, R 45 ~R 48 C1, R2, R 31 R 32 R 34 R 35 L1, R 11 ~R 18 m and k are respectively related to X1, R4, R in the general formula (100) 45 ~R 48 C1, R2, R 31 R 32 R 34 R 35 L1, R 11 ~R 18 m and k are synonyms.

[0150] In the general formula (100Z), k is preferably 1 or 2.

[0151] In the general formula (100Z), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0152] In compound M3 of this embodiment, R is preferred. 11 ~R 18 R4 and R 45 ~R 48Each of the following is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0153] In compound M3 of this embodiment, R is more preferably preferred. 11 ~R 18 R4 and R 45 ~R 48 Each of the following groups is independently a hydrogen atom, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms.

[0154] In compound M3 of this embodiment, R is further preferred. 11 ~R 18 R4 and R 45 ~R 48 Each aryl group is independently composed of a hydrogen atom, or is either substituted or unsubstituted and has 6 to 30 cyclic carbon atoms.

[0155] In compound M3 of this embodiment, R is further preferred. 11 ~R 18 R4 and R 45 ~R 48 Each is a hydrogen atom, or a substituted or unsubstituted phenyl group.

[0156] In compound M3 of this embodiment, R is preferred. 11 ~R 18 Each of the following is independently a hydrogen atom or a substituted or unsubstituted phenyl group: R4 and R 45 ~R 48 Each is an independent hydrogen atom.

[0157] In this embodiment, if compound M3 is a compound represented by any one of the general formulas (401) to (406), (401A) to (406A), and (401B) to (406B), R is preferred. 11 ~R 18 R 401 ~R 404 R4 and R 41 R 42 and R 44 ~R 48 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. More preferably, it is a hydrogen atom, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. Further preferred are hydrogen atoms, or aryl groups with 6 to 30 substituted or unsubstituted carbon atoms in the cyclic group. More preferably, it contains hydrogen atoms, or substituted or unsubstituted phenyl groups.

[0158] In this embodiment, if compound M3 is a compound represented by any one of the general formulas (401) to (406), (401A) to (406A), and (401B) to (406B), R is preferred. 11 ~R 18 and R 401 ~R 404 R4 and R are each independently a hydrogen atom, or a substituted or unsubstituted phenyl group. 41 R 42 and R 44 ~R 48 Each is an independent hydrogen atom.

[0159] In compound M3 of this embodiment, L1 is preferably a single bond or a group derived from an unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

[0160] In compound M3 of this embodiment, L1 is more preferably a single bond or a group derived from an unsubstituted benzene ring.

[0161] In compound M3 of this embodiment, L1 is preferably a single bond.

[0162] The compound M3 in this embodiment is preferably a compound represented by the following general formula (100A) or the following general formula (100B).

[0163] The compound M3 in this embodiment is more preferably a compound represented by the following general formula (100A).

[0164]

Chemistry 24

[0165]

Chemistry 25

[0166] In the general formulas (100A) and (100B), X1 and R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 41 ~R 44 Each is independently synonymous with R4 in the general formula (100).

[0167] In the general formula (100A), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0168] In the general formula (100B), R has 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0169] In compound M3 of this embodiment, when L1 is a linking group, it is preferable that L1 is bonded to a carbon atom at position b, c or d as shown in the general formula (100).

[0170] In compound M3 of this embodiment, when L1 is a divalent linking group, n is 1, and k is 1, it is preferable that L1 is bonded to the carbon atom at position c shown in the general formula (100).

[0171] In compound M3 of this embodiment, when L1 is a trivalent linker, n is 2, and k is 1, it is preferable that L1 is bonded to the carbon atom at position c shown in the general formula (100).

[0172] In compound M3 of this embodiment, when L1 is a single bond, n is 1, and k is 1, it is preferable that the nitrogen atom at position 9 of the carbazole ring represented by the general formula (100) is bonded to the carbon atom at position c represented by the general formula (100).

[0173] In compound M3 of this embodiment, when L1 is a single bond, n is 2, and k is 2, it is preferable that the nitrogen atom at the 9th position of the two carbazole rings shown in the general formula (100) is bonded to the carbon atoms at positions b and d shown in the general formula (100), respectively.

[0174] In compound M3 of this embodiment, when L1 is a single bond, n is 3, and k is 3, it is preferable that the nitrogen atom at position 9 of the three carbazole rings shown in the general formula (100) is bonded to the carbon atoms at positions b, c, and d shown in the general formula (100), respectively.

[0175] The compound M3 in this embodiment is preferably a compound represented by the following general formula (100C).

[0176]

Chemistry 26

[0177] In the general formula (100C), X1, C1, R 11 ~R 18 n, L1, R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 respectively with X1, C1, R in the general formula (100) 11 ~R 18 n, L1, R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 Synonyms, R 21 R 22 R 24 and R 25 Each is independently synonymous with R2 in the general formula (100).

[0178] In the general formula (100C), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0179] The compound M3 in this embodiment is preferably a compound represented by the following general formula (100D).

[0180]

Chemistry 27

[0181] In the general formula (100D), X1, C1, R 11 ~R 18 R 31 R 32 R 34 R 35 R4 and R 45 ~R 48respectively with X1, C1, R in the general formula (100) 11 ~R 18 R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 Synonyms, R 21 R 23 and R 25 Each is independently synonymous with R2 in the general formula (100).

[0182] In the general formula (100D), there are 2 Rs 11 Same or different, 2 R 12 Same or different, 2 R 13 Same or different, 2 R 14 Same or different, 2 R 15 Same or different, 2 R 16 Same or different, 2 R 17 Same or different, 2 R 18 Same or different.

[0183] In the general formula (100D), R is present. 11 ~R 18 The two ring structures are also preferably represented independently by any one of the general formulas (400-1) to (400-6).

[0184] The compound M3 in this embodiment is preferably a compound represented by the following general formula (100E).

[0185]

Chemistry 28

[0186] In the general formula (100E), X1 and C1 are synonyms with X1 and C1 in the general formula (100), respectively, n is 1 or 2, k is 1 or 2, and R 11 ~R 18 R4 and R 45 ~R 48 Each aryl group is independently a hydrogen atom, or a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, wherein at least one of n and k is 2, and multiple R groups are formed. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups consisting of two or more R4s do not bond to each other. L1 is a single bond or a group derived from an unsubstituted aryl group with 6 to 30 unsubstituted cyclic carbon atoms, wherein, when L1 is a single bond, n is 1. When k is 2, multiple L1 values ​​can be identical or different from each other. When L1 is a linking group and k is 1, one L1 group bonds to a carbon atom at position a, b, c, d, or e. When L1 is a linking group and k is 2, the two L1 groups are bonded to carbon atoms at any position of a, b, c, d, and e, respectively. However, multiple L1 groups are not bonded to carbon atoms at the same position. When L1 is a single bond and k is 1, the nitrogen atom at position 9 of the carbazole ring shown in the general formula (100E) is bonded to the carbon atom at position a, b, c, d, or e shown in the general formula (100E). When L1 is a single bond and k is 2, the 9-position nitrogen atom of the two carbazole rings shown in the general formula (100E) is bonded to carbon atoms at any position of a, b, c, d and e shown in the general formula (100E), wherein the 9-position nitrogen atom of multiple carbazole rings is not bonded to carbon atoms at the same position.

[0187] The compound M3 in this embodiment is preferably a compound represented by the following general formula (100F).

[0188]

Chemistry 29

[0189] In the general formula (100F), X1 and C1 are synonyms with X1 and C1 in the general formula (100), respectively, and n is 1 or 2. When n is 1, the nitrogen atom at position 9 of one carbazole ring represented by the general formula (100F) is bonded to the carbon atom at position a, b, c, d, or e represented by the general formula (100F). When n is 2, the nitrogen atom at position 9 of the two carbazole rings shown in the general formula (100F) is bonded to carbon atoms at any position a, b, c, d, and e, respectively. However, the nitrogen atom at position 9 of multiple carbazole rings is not bonded to carbon atoms at the same position. R 11 ~R 18 Each of the R atoms is independently a hydrogen atom or a substituted or unsubstituted phenyl group, and when n is 2, there are multiple R atoms. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups do not bond with each other.

[0190] In compound M3 of this embodiment, X1 is preferably an oxygen atom.

[0191] In the compound M3 of this embodiment, it is also preferable that C1 in the general formula (100) is bonded to the carbon atom at the position of "h" shown in the general formula (100). R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0192] The compound M3 in this scheme is represented by the following general formula (201A).

[0193]

Transformation 30

[0194] In the general formula (201A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 41 R 42 and R 44 Each is independently synonymous with R4 in the general formula (100). Wherein, in the general formula (201A), R... 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0195] The compound represented by the general formula (201A) is synonymous with the compound represented by the general formula (201) in the fourth embodiment described later.

[0196] That is, in the general formula (201A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32R 34 R 35 R 41 R 42 R 44 and R 45 ~R 48 respectively with X1 and R in general formula (201) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 42 R 44 and R 45 ~R 48 Synonyms.

[0197] The compound of the fourth embodiment is a compound capable of realizing high-performance organic EL elements, such as organic EL elements that emit light with long lifetimes. Therefore, the compound of the fourth embodiment can be used as compound M3 in the first embodiment.

[0198] In the compound M3 of this embodiment, it is also preferable that C1 in the general formula (100) is bonded to the carbon atom at the position of "g" shown in the general formula (100). R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0199] The compound M3 in this scheme is represented by the following general formula (202A).

[0200]

Chemistry 31

[0201] In the general formula (202A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R35 and R 45 ~R 48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 41 R 43 and R 44 Each is independently synonymous with R4 in the general formula (100). Wherein, in the general formula (202A), R... 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0202] The compound represented by the general formula (202A) is synonymous with the compound represented by the general formula (202) in the fourth embodiment described later.

[0203] That is, in the general formula (202A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 43 R 44 and R 45 ~R 48 respectively with X1 and R in general formula (201) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 43 R 44 and R45 ~R 48 Synonyms.

[0204] The compound of the fourth embodiment is a compound capable of realizing high-performance organic EL elements, such as organic EL elements that emit light with long lifetimes. Therefore, the compound of the fourth embodiment can be used as compound M3 in the first embodiment.

[0205] In the compound M3 of this embodiment, it is also preferable that C1 in the general formula (100) is bonded to the carbon atom at the position of "f" shown in the general formula (100). R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0206] The compound M3 in this scheme is represented by the following general formula (203A).

[0207]

Chemistry 32

[0208] In the general formula (203A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 42 ~R 44 Each is independently synonymous with R4 in the general formula (100). Wherein, in the general formula (203A), R... 11and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0209] The compound represented by the general formula (203A) is synonymous with the compound represented by the general formula (203) in the fourth embodiment described later.

[0210] That is, in the general formula (203A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 42 ~R 44 and R 45 ~R 48 respectively with X1 and R in general formula (201) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 42 ~R 44 and R 45 ~R 48 Synonyms.

[0211] The compound of the fourth embodiment is a compound capable of realizing high-performance organic EL elements, such as organic EL elements that emit light with long lifetimes. Therefore, the compound of the fourth embodiment can be used as compound M3 in the first embodiment.

[0212] In the compound M3 of this embodiment, it is also preferred that C1 in the general formula (100) is bonded to the carbon atom at the position of "i" shown in the general formula (100).

[0213] The compound M3 in this scheme is represented by the following general formula (300A).

[0214]

Transformation 33

[0215] In the general formula (300A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 41 ~R 43 Each is independently synonymous with R4 in the general formula (100).

[0216] The compound represented by the general formula (300A) is synonymous with the compound represented by the general formula (300) in the fifth embodiment described later.

[0217] That is, in the general formula (300A), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 respectively with X1 and R in general formula (300) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 Synonyms.

[0218] In the general formula (300A), R is present. 11 ~R 18 The ring structure is also preferably represented by any one of the general formulas (400-1) to (400-6).

[0219] The compound of the fifth embodiment is a compound capable of realizing high-performance organic EL elements, such as organic EL elements that emit light with long lifetimes. Therefore, the compound of the fifth embodiment can be used as compound M3 in the first embodiment.

[0220] • Method for manufacturing compound M3 according to this embodiment Compound M3 of this embodiment can be manufactured, for example, by the method described in the examples described later. Compound M3 of this embodiment can be manufactured by mimicking the reactions described in the examples described later, using known alternative reactions and starting materials that match the target compound.

[0221] As a specific example of compound M3 in this embodiment, the following compounds may be cited. However, the present invention is not limited to these specific examples of compounds.

[0222]

Transformation 34

[0223]

Chemistry 35

[0224]

Transformation 36

[0225]

Chemistry 37

[0226]

Transformation 38

[0227]

Chemistry 39

[0228]

Chemistry 40

[0229]

Chemistry 41

[0230]

Chemistry 42

[0231]

Chemistry 43

[0232]

Chemistry 44

[0233]

Chemistry 45

[0234]

Chemistry 46

[0235]

Chemistry 47

[0236]

Chemistry 48

[0237]

Chemistry 49

[0238] [Transformation 50]

[0239]

Chemistry 51

[0240]

Chemistry 52

[0241]

Chemistry 53

[0242]

Chemistry 54

[0243]

Transformation 55

[0244]

Transformation 56

[0245]

Chemistry 57

[0246]

Chemistry 58

[0247]

Chemistry 59

[0248]

Transformation 60

[0249]

Chemistry 61

[0250]

Transformation 62

[0251]

Transformation 63

[0252]

Chemical Formula 64

[0253]

Chemical Formula 65

[0254]

Chemical Formula 66

[0255]

Chemical Formula 67

[0256]

Chemical Formula 68

[0257]

Chemical Formula 69

[0258]

Chemical Formula 70

[0259]

Chemical Formula 71

[0260]

Chemical Formula 72

[0261] (Compound M2) The light-emitting layer of this embodiment contains a compound M2 with delayed fluorescence properties.

[0262] As the compound M2 with delayed fluorescence properties, for example, a compound represented by the following general formula (1) can be cited.

[0263]

Chemical Formula 73

[0264] In the general formula (1), n is an integer of 1 or more and 4 or less, m is an integer of 1 or more and 4 or less, q is an integer of 0 or more and 4 or less, and m + n + q = 6. CN is a cyano group, The D1 is a group represented by the following general formula (2), the following general formula (3), or the following general formula (3x). When there are multiple D1s, the multiple D1s are the same or different from each other. Rx is a hydrogen atom or a substituent, or the groups of adjacent Rx bond to each other to form a ring. When there are multiple Rx, the multiple Rx are the same or different from each other. As substituents, Rx are each independently a halogen atom, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted amino groups Substituted or unsubstituted carbonyl groups Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 30 carbon atoms, or Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms in the cyclic structure. CN, D1, and Rx are bonded to carbon atoms in a six-membered ring, respectively.

[0265]

Chemistry 74

[0266] In the general formula (2), R1 to R8 are each independently a hydrogen atom or a substituent, or any one or more of the following groups are bonded together to form a ring: R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, and R7 and R8. The substituents R1 to R8 are each independently, Halogen atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted haloalkoxy groups with 1 to 30 carbon atoms Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0267] * indicates the site where the benzene ring in the general formula (1) is bonded to a carbon atom.

[0268]

Chemistry 75

[0269] In the general formula (3), R 31 ~R 38 Each is independently a hydrogen atom or a substituent, or R 31 and R 32 group, R 32 and R 33 group, R 33 and R 34 group, R 35 and R 36 group, R 36 and R 37 The group, and R 37 and R 38 A ring is formed by bonding any one or more groups within a group together. R as a substituent 31 ~R 38 Each of them is independently synonymous with R1 to R8 in the general formula (2). A represents a ring structure represented by the following general formula (131) or the following general formula (132), wherein the ring structure A is fused with adjacent ring structures at any position, where p is an integer of 1 to 4, and in the case where p is an integer of 2 or more, the multiple ring structures A are the same or different from each other. * indicates the site where the benzene ring in the general formula (1) is bonded to a carbon atom.

[0270]

Transformation 76

[0271] In the general formula (3X), R 41 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 41 ~R48 are each independently the same as R as a substituent in the general formula (3) 31 ~R 38 , B represents a ring structure represented by the following general formula (131) or the following general formula (132), and this ring structure B is fused to an adjacent ring structure at an arbitrary position. px is an integer of 1 or more and 4 or less. When px is an integer of 2 or more, the plurality of ring structures B are the same or different from each other. C represents a ring structure represented by the following general formula (131) or the following general formula (132), and this ring structure C is fused to an adjacent ring structure at an arbitrary position. py is an integer of 1 or more and 4 or less. When py is an integer of 2 or more, the plurality of ring structures C are the same or different from each other. * represents the position where the benzene ring in the general formula (1) is bonded to a carbon atom.

[0272]

Chemical formula 77

[0273] In the general formula (131), R 19 and R 20 are each independently a hydrogen atom or a substituent, or are bonded to each other with a part of an adjacent ring structure to form a ring, or the groups of R 19 and R 20 are bonded to each other to form a ring. In the general formula (132), X1 is CR 50 R 51 , NR 52 , a sulfur atom or an oxygen atom, and R 50 , R 51 and R 52 are each independently a hydrogen atom or a substituent, or R 50 and R 51 are bonded to each other to form a ring. R as a substituent 19 , R 20 , R 50 , R 51 and R 52 are each independently the same as R1 to R8 as substituents in the general formula (2).

[0274] In the general formula (131), R 19 and R 20 being bonded to each other with a part of an adjacent ring structure to form a ring specifically means any one of the following (I) to (IV).

[0275] In addition, in the general formula (131), R 19 and R 20The groups bond together to form a ring, specifically referring to the following (V). (I) When the ring structures represented by general formula (131) are adjacent to each other, one of the two adjacent rings, R, is a ring. 19 And another ring R 19 A group, a ring R 19 And another ring R 20 The group, and a ring R 20 And another ring R 20 A ring is formed by bonding any one or more groups within a group together.

[0276] (II) The ring structure represented by general formula (131) and the one with R in general formula (3) 35 ~R 38 When the benzene rings are adjacent, one of the two adjacent rings, R... 19 And another ring R 35 A group, a ring R 19 And another ring R 38 A group, a ring R 20 And another ring R 35 The group, and a ring R 20 And another ring R 38 A ring is formed by bonding any one or more groups within a group together.

[0277] (III) The ring structure represented by general formula (131) and the one with R in general formula (3X) 41 ~R 44 When the benzene rings are adjacent, one of the two adjacent rings, R... 19 And another ring R 41 A group, a ring R 19 And another ring R 44 A group, a ring R 20 And another ring R 41 The group, and a ring R 20 And another ring R 44 A ring is formed by bonding any one or more groups within a group together.

[0278] (IV) The ring structure represented by general formula (131) and the one with R in general formula (3X) 45 ~R 48 When the benzene rings are adjacent, one of the two adjacent rings, R... 19 And another ring R 45 A group, a ring R 19 And another ring R 48 A group, a ring R 20 And another ring R 45 The group, and a ring R20 And another ring R 48 A ring is formed by bonding any one or more groups within a group together.

[0279] (V) R of the ring structure represented by general formula (131) 19 and R 20 The groups bond to each other to form a ring. That is, (V) refers to R that is bonded to the same ring. 19 and R 20 The groups bond together to form a ring.

[0280] In compound M2 of this embodiment, Rx is independently, hydrogen atom, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or Unsubstituted alkyl groups having 1 to 30 carbon atoms, When Rx is an unsubstituted heterocyclic group with 5 to 30 cyclic atoms, Rx is preferably pyridyl, pyrimidinyl, triazine, dibenzofuranyl, or dibenzothiopheneyl.

[0281] In this specification, triazine group refers to a group obtained by removing one hydrogen atom from 1,3,5-triazine, 1,2,4-triazine or 1,2,3-triazine.

[0282] The triazine group is preferably a group obtained by removing one hydrogen atom from 1,3,5-triazine.

[0283] In compound M2 of this embodiment, it is more preferable that Rx is independently, hydrogen atom, Unsubstituted aryl groups with 6 to 30 carbon atoms, or Unsubstituted dibenzofuranyl, or Unsubstituted dibenzothiophene group.

[0284] In compound M2 of this embodiment, Rx is further preferably a hydrogen atom.

[0285] In compound M2 of this embodiment, R1 to R8 and R are preferably used as substituents. 31 ~R 38 R 19 ~R 20 R 41 ~R 48 and R 50 ~R 52 Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or Unsubstituted alkyl groups having 1 to 30 carbon atoms.

[0286] In this embodiment, compound M2 is preferably a compound represented by any one of the following general formulas (1-1) to (1-47).

[0287]

Transformation 78

[0288]

Chemistry 79

[0289]

Chemistry 80

[0290]

Chemistry 81

[0291] In the general formulas (1-1) to (1-47), D1 is independently synonymous with D1 in the general formula (1), and Rx is independently synonymous with Rx in the general formula (1).

[0292] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17), and (1-23) to (1-25).

[0293] In this embodiment, compound M2 is more preferably a compound represented by general formula (1-6), (1-23), or (1-24).

[0294] The compound M2 in this embodiment is further preferably a compound represented by the following general formula (1-6A), (1-23A) or (1-24A).

[0295]

Chemistry 82

[0296] In the general formulas (1-6A), (1-23A) and (1-24A), D1 is independently synonymous with D1 in the general formula (1).

[0297] The compound M2 in this embodiment is preferably a compound represented by general formulas (1-6).

[0298] The compound M2 in this embodiment is preferably a compound represented by general formula (1-23).

[0299] The compound M2 in this embodiment is preferably a compound represented by general formula (1-24).

[0300] The compound M2 in this embodiment is preferably a compound represented by the general formula (1-1), (1-10), or (1-21).

[0301] In compound M2 of this embodiment, D1 is preferably a group represented by any one of the following general formulas (3-1) to (3-12).

[0302]

Chemistry 83

[0303]

Chemical 84

[0304]

Chemical 85

[0305] In the general formulas (3-1) to (3-6), R 11 ~R 16 As a substituent, R 101 ~R 150 and R 61 ~R 70 Each can be an independent hydrogen atom or a substituent. R as a substituent 101 ~R 150 and R 61 ~R 70 Each independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms hydroxyl, Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms, substituted or unsubstituted arylamino groups with 6 to 28 carbon atoms in the cyclic formation, Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 14 carbon atoms in the cyclic formation. R as a substituent 11 ~R 16 Each independently, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms A substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0306] * represents the bonding site of the benzene ring in the general formula (1) to a carbon atom.

[0307]

Chemical formula 86

[0308]

Chemical formula 87

[0309]

Chemical formula 88

[0310] In the general formulas (3-7) to (3-12), X1 to X6 are each independently an oxygen atom, a sulfur atom or CR 151 R 152 , R 201 ~R 260 are each independently a hydrogen atom or a substituent, R 151 and R 152 are each independently a hydrogen atom or a substituent, or R 151 and R 152 bond to each other to form a ring, As substituents, R 201 ~R 260 , R 151 and R 152 are each independently, a halogen atom, <00031*******a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, ​​​​Substituted or unsubstituted haloalkoxy groups having 1 to 6 carbon atoms Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms, substituted or unsubstituted arylamino groups with 6 to 28 carbon atoms in the cyclic formation, Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or Arylthio groups with 6 to 14 carbon atoms, either substituted or unsubstituted.

[0311] * indicates the site where the benzene ring in the general formula (1) is bonded to a carbon atom.

[0312] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by any one of the general formulas (3-7) to (3-12), and it is also preferred that X1 to X6 in the general formulas (3-7) to (3-12) are sulfur atoms.

[0313] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by general formula (3-12), and it is also preferred that X6 in general formula (3-12) is a sulfur atom.

[0314] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by any one of the general formulas (3-7) to (3-12), where X1 to X6 in the general formulas (3-7) to (3-12) are oxygen atoms.

[0315] In compound M2 of this embodiment, it is also preferred that D1 is a group represented by any one of the general formulas (3-7) to (3-12), and X1 to X6 in general formulas (3-7) to (3-12) are CR 151 R 152 .

[0316] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by any one of the general formulas (3-1) to (3-6).

[0317] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17) and (1-23) to (1-25), and D1 is a group represented by any one of the general formulas (3-1) to (3-12).

[0318] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17) and (1-23) to (1-25), D1 is a group represented by any one of the general formulas (3-7) to (3-12), and X1 to X6 in the general formulas (3-7) to (3-12) are sulfur atoms.

[0319] In this embodiment, compound M2 is preferably a compound represented by general formula (1-6), (1-23) or (1-24), D1 is a group represented by any one of general formulas (3-7) to (3-12), and X1 to X6 in general formulas (3-7) to (3-12) are sulfur atoms.

[0320] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17) and (1-23) to (1-25), D1 is a group represented by any one of the general formulas (3-7) to (3-12), and X1 to X6 in the general formulas (3-7) to (3-12) are oxygen atoms.

[0321] In this embodiment, compound M2 is preferably a compound represented by general formula (1-6), (1-23) or (1-24), D1 is a group represented by any one of general formulas (3-7) to (3-12), and X1 to X6 in general formulas (3-7) to (3-12) are oxygen atoms.

[0322] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17), and (1-23) to (1-25), D1 is a group represented by any one of the general formulas (3-7) to (3-12), and X1 to X6 in general formulas (3-7) to (3-12) are CR 151 R 152 .

[0323] In this embodiment, compound M2 is preferably a compound represented by general formula (1-6), (1-23), or (1-24), D1 is a group represented by any one of general formulas (3-7) to (3-12), and X1 to X6 in general formulas (3-7) to (3-12) are CR 151 R 152 .

[0324] The compound M2 in this embodiment is preferably a compound represented by any one of the general formulas (1-4) to (1-7), (1-14) to (1-17) and (1-23) to (1-25), and D1 is a group represented by any one of the general formulas (3-1) to (3-6).

[0325] In this embodiment, compound M2 is preferably a compound represented by general formula (1-6), (1-23) or (1-24), and D1 is a group represented by any one of general formulas (3-1) to (3-6).

[0326] In compound M2 of this embodiment, R is preferably used as a substituent. 101 ~R 150 and R 61 ~R 70 Each independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms, or Unsubstituted alkyl groups having 1 to 6 carbon atoms, R as a substituent 11 ~R 16 Each independently, Unsubstituted aryl groups with 6 to 14 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms.

[0327] In compound M2 of this embodiment, R is also preferred. 101 ~R 150 and R 61 ~R 70 It is a hydrogen atom. R as a substituent 11 ~R 16 Each independently, Unsubstituted aryl groups with 6 to 14 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms.

[0328] In compound M2 of this embodiment, R is preferably used as a substituent. 201 ~R 260 Each independently, Halogen atoms, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms, R as a substituent 151 and R 152 Each independently, Unsubstituted aryl groups with 6 to 14 carbon atoms, or Unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0329] Furthermore, in compound M2 of this embodiment, R is more preferably a substituent.201 ~R 260 Each independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms, R as a substituent 151 and R 152 Each independently, Unsubstituted aryl groups with 6 to 14 carbon atoms, or Unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0330] In compound M2 of this embodiment, R is also preferred. 201 ~R 260 It is a hydrogen atom. R as a substituent 151 and R 152 Each independently, Unsubstituted aryl groups with 6 to 14 carbon atoms, or Unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0331] In the compound M2 of this embodiment, it is also preferred that D1 is a group represented by the following general formula (2-1), (2-2), (2-3) or (2-4).

[0332]

Chemistry 89

[0333] [Chemical 90]

[0334] In the general formulas (2-1) to (2-4), R 171 ~R 200 and R 71 ~R 82 Each is 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 R180 group, R 181 and R 182 group, R 182 and R 183 group, R 183 and R 184 group, R 185 and R 186 group, R 186 and R 187 group, R 187 and R 188 group, R 188 and R 189 group, R 189 and R 190 group, R 191 and R 192 group, R 192 and R 193 group, R 193 and R 194 group, R 194 and R 195 group, R 195 and R 196 group, R 197 and R 198 group, R 198 and R 199 group, R 199 and R 200 group, R 71 and R 72 group, R 72 and R 73 group, R 73 and R 74 group, R 75 and R 76 group, R 76 and R 77 group, R 77 and R 78 group, R 79 and R 80 group, R 80 and R 81 The group, and R 81 and R 82 A ring is formed by bonding any one or more groups within a group together. R as a substituent 171 ~R 200 and R 71 ~R 82 Each independently, Halogen atoms, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms hydroxyl, Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms Substituted or unsubstituted haloalkoxy groups having 1 to 6 carbon atoms Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms, Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or Arylthio groups with 6 to 14 carbon atoms, either substituted or unsubstituted.

[0335] * indicates the site where the benzene ring in the general formula (1) is bonded to a carbon atom.

[0336] In the compound M2 of this embodiment, it is even more preferable that D1 is a group represented by general formula (2-1), (2-3) or (2-4).

[0337] In compound M2 of this embodiment, it is further preferred that D1 is a group represented by general formula (2-1) or (2-3).

[0338] In this embodiment, compound M2 is preferably a compound represented by any one of the general formulas (1-1), (1-4) to (1-7), (1-10), (1-14) to (1-17), (1-21), and (1-23) to (1-25), and D1 is a group represented by the general formula (2-1), (2-2), (2-3), or (2-4).

[0339] In this embodiment, compound M2 is preferably a compound represented by general formula (1-6), (1-23) or (1-24), and D1 is a group represented by general formula (2-1), (2-2), (2-3) or (2-4).

[0340] The compound M2 in this embodiment is preferably a compound represented by general formula (1-1), (1-10) or (1-21), and D1 is a group represented by general formula (2-1), (2-2), (2-3) or (2-4), and more preferably a group represented by general formula (2-1), (2-3) or (2-4).

[0341] In compound M2 of this embodiment, R is preferably used as a substituent. 171 ~R 200 and R 71 ~R 82 Each independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms, or Unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0342] In compound M2 of this embodiment, R is also preferred. 171 ~R 200 and R 71 ~R 82 It is a hydrogen atom.

[0343] • Method for manufacturing compound M2 according to this embodiment The compound M2 of this embodiment can be manufactured by known methods.

[0344] As a specific example of compound M2 in this embodiment, the following compounds may be cited. However, the present invention is not limited to these specific examples of compounds.

[0345]

Chemistry 91

[0346]

Chemistry 92

[0347]

Chemistry 93

[0348]

Chemical 94

[0349]

Chemical 95

[0350]

Chemistry 96

[0351]

Chemistry 97

[0352]

Chem.98

[0353]

Chem.99

[0354]

Chemistry 100

[0355]

Chemistry 101

[0356]

Chemical Engineering 102

[0357]

Chemistry 103

[0358]

Chemical 104

[0359]

Chemistry 105

[0360]

Chemistry 106

[0361]

Chemistry 107

[0362]

Chemistry 108

[0363]

Chemistry 109

[0364] Delayed fluorescence Regarding delayed fluorescence, it is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). This document states that if the energy difference ΔE between the excited singlet and excited triplet states of a fluorescent material can be reduced... 13 In this case, the reverse energy transfer from the excited triplet state with low migration probability to the excited singlet state usually occurs efficiently, producing thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is illustrated in Figure 10.38 of this document. Compound M2 in this embodiment is preferably a compound that demonstrates thermally activated delayed fluorescence generated by such a mechanism.

[0365] Typically, delayed fluorescence can be confirmed by transition PL (Photo Luminescence) measurements.

[0366] Furthermore, the behavior of delayed fluorescence can be analyzed based on the decay curve obtained from transition PL measurements. Transition PL measurement refers to the method of irradiating the sample with a pulsed laser to excite it, and then measuring the decay behavior (transition characteristics) of PL emission after irradiation stops. PL emission in TADF materials consists of two components: the emission component from singlet excitons generated by the initial PL excitation and the emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after pulsed laser irradiation.

[0367] On the other hand, delayed fluorescence originates from the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays gradually. Consequently, there is a significant time difference between the emission of singlet excitons generated from the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[0368] Figure 2 The diagram shows a schematic of an example apparatus for measuring transient PL. Figure 2 The method for measuring transition PL and an example of analyzing the behavior of delayed fluorescence are explained.

[0369] Figure 2 The transition PL measurement device 100 includes: a pulsed laser unit 101 for irradiating light of a specified wavelength; a sample chamber 102 for housing the measurement sample; a beam splitter 103 for splitting the light emitted from the measurement sample; a streak camera 104 for imaging a two-dimensional image; and a personal computer 105 for reading and analyzing the two-dimensional image. Furthermore, the measurement of transition PL is not limited to... Figure 2 The device described.

[0370] The sample housed in the sample chamber 102 can be obtained by forming a thin film on a quartz substrate by doping the matrix material with a dopant material at a concentration of 12% by mass.

[0371] For the thin film sample housed in the sample chamber 102, a pulsed laser is irradiated from the pulsed laser unit 101 to excite the doped material. The emitted light is extracted in a direction 90 degrees relative to the irradiation direction of the excitation light, and the extracted light is split by the beam splitter 103 to form a two-dimensional image in the streak camera 104. The result is a two-dimensional image with the vertical axis corresponding to time, the horizontal axis corresponding to wavelength, and the bright spots corresponding to emission intensity. If this two-dimensional image is cut along a specified time axis, an emission spectrum with emission intensity as the vertical axis and wavelength as the horizontal axis can be obtained. Furthermore, if this two-dimensional image is cut along the wavelength axis, a decay curve (transition pulse) with the logarithm of emission intensity as the vertical axis and time as the horizontal axis can be obtained.

[0372] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the dopant material, thin film sample A was prepared as described above, and transition PL measurements were performed.

[0373]

Chemical 110

[0374] Here, the decay curves were analyzed using thin film sample A and thin film sample B. Thin film sample B was prepared using the reference compound H2 as the matrix material and the reference compound D1 as the dopant material, as described above.

[0375] Figure 3 The attenuation curves obtained from the transition PL measured on thin film sample A and thin film sample B are shown in the figure.

[0376]

Chemistry 111

[0377] As described above, by measuring the transition PL (luminescence intensity), a luminescence decay curve can be obtained with luminescence intensity as the vertical axis and time as the horizontal axis. Based on this luminescence decay curve, the fluorescence intensity ratio of fluorescence emitted from a singlet excited state generated by photoexcitation to delayed fluorescence emitted from a singlet excited state generated via reverse energy transfer from a triplet excited state can be calculated. In materials with delayed fluorescence, the proportion of slowly decaying delayed fluorescence intensity is relatively large compared to the intensity of rapidly decaying fluorescence.

[0378] Specifically, luminescence from materials with delayed fluorescence can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence observed immediately from the excited state after being excited by a pulse of light (light from a pulsed laser) of a wavelength absorbed by the material with delayed fluorescence. Delay luminescence refers to luminescence that is not immediately observed after the material is excited by the pulse of light but is observed later.

[0379] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0380] Furthermore, in this specification, a sample prepared by the method described below is used in the measurement of the delayed fluorescence of compound M2. For example, compound M2 is dissolved in toluene, and a dilute solution with an absorbance of less than 0.05 at the excitation wavelength is prepared to eliminate the effect of self-absorption. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[0381] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al., J. Phys. Chem., 80 (1976) 969.

[0382] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0383] In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the target compound (compound M2) is denoted as X. P The amount of delayed emission is denoted as X. D At that time, X D / X P The value is preferably 0.05 or higher.

[0384] The measurement of the amount and ratio of Prompt luminescence and Delay luminescence for compounds other than compound M2 in this specification is the same as the measurement of the amount and ratio of Prompt luminescence and Delay luminescence for compound M2.

[0385] <The relationship between compounds M3 and M2 in the luminescent layer> In the organic EL element of this embodiment, the singlet energy S1(M2) of compound M2 and the singlet energy S1(M3) of compound M3 satisfy the following mathematical expression (number 1).

[0386] S1(M3) > S1(M2) (Number 1) The band gap T at 77 [K] is preferably that of compound M3. 77K The band gap T of (M3) is greater than that of compound M2 at 77 [K]. 77K(M2). That is, preferably, the relationship satisfies the following mathematical expression (number 11).

[0387] T 77K (M3) > T 77K (M2)...(Number 11) Preferably, when the organic EL element of this embodiment emits light, compound M3 does not emit light primarily in the light-emitting layer.

[0388] • Relationship between triplet energy and band gap at 77 K Here, the relationship between the triplet energy and the band gap at 77 [K] is explained. In this embodiment, the band gap at 77 [K] differs from the normally defined triplet energy.

[0389] The triplet energy was measured as follows. First, the compound to be measured was dissolved in a suitable solvent, and the resulting solution was sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy was calculated based on the wavelength value of the intersection of this tangent and the horizontal axis according to the prescribed conversion formula.

[0390] In this embodiment, the compound with thermally activated delayed fluorescence (ΔST) is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are more likely to occur even at low temperatures (77 [K]), resulting in the coexistence of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as described above can be considered to contain emission from both the excited singlet and excited triplet states, making it difficult to distinguish which state the emission originates from, but the triplet energy value is essentially dominant.

[0391] Therefore, in this embodiment, the measurement method is the same as that for the usual triplet energy T, but in order to distinguish it strictly, the measured value is referred to as the bandgap T. 77K The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent and the horizontal axis was determined. edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the band gap T at 77[K]. 77K .

[0392] Conversion formula (F1): T77K [eV]=1239.85 / λ edge The tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum is drawn as shown below. Consider this tangent as it moves along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the point on the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the value of the vertical axis increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum.

[0393] Furthermore, the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point closest to the maximum value on the shortest wavelength side and where the slope value is the maximum value is taken as the tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum.

[0394] Phosphorescence can be measured using the main body of the Hitachi High Technology Co., Ltd. F-4500 spectrophotometer. However, the measuring device is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.

[0395] Singlet energy S1 The following methods can be cited as examples of methods for measuring the singlet energy S1 using a solution (sometimes called the solution method).

[0396] A 10 μmol / L toluene solution of the compound to be measured was placed in a quartz cell, and the absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). A tangent was drawn to the falling edge of the longer wavelength side of the absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy.

[0397] Conversion formula (F2): S1[eV]=1239.85 / λedge As an absorption spectroscopy measuring device, an example of such a device is the Hitachi spectrophotometer (device name: U3310), but it is not limited to this.

[0398] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is plotted as shown below. Consider this tangent at various points on the spectral curve as the maximum value on the longest wavelength side of the absorption spectrum is moved along the longer wavelength direction. This tangent repeatedly shows a decreasing and then increasing slope as the curve descends (i.e., as the vertical axis value decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent to the falling edge of the longer wavelength side of the absorption spectrum.

[0399] In addition, the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[0400] In this embodiment, the singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as △ST.

[0401] In this embodiment, the singlet energy S1(M2) of compound M2 and the band gap T at 77 [K] of compound M2 are... 77K The difference ΔST(M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the following mathematical expressions (Number 1A) to (Number 1D).

[0402] △ST(M2) = S1(M2) - T 77K (M2) < 0.3 eV (number 1A) △ST(M2) = S1(M2) - T 77K (M2) < 0.2 eV (Number 1B) △ST(M2) = S1(M2) - T 77K (M2) < 0.1 eV (C) △ST(M2) = S1(M2) - T 77K (M2) < 0.01 eV (number 1D) • Film thickness of the light-emitting layer In this embodiment, the thickness of the light-emitting layer in the organic EL element is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. If it is 5 nm or more, the formation of the light-emitting layer and the adjustment of color become easier; if it is 50 nm or less, it is easier to suppress the rise of the driving voltage.

[0403] • The content of compounds in the luminescent layer The content of compounds M2 and M3 in the light-emitting layer is preferably within, for example, the following range.

[0404] The content 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 even more preferably 20% by mass or more and 60% by mass or less.

[0405] The content of compound M3 is preferably 20% by mass or more and 90% by mass, more preferably 40% by mass or more and 90% by mass, and even more preferably 40% by mass or more and 80% by mass.

[0406] Furthermore, this embodiment does not exclude the inclusion of materials other than compounds M2 and M3 in the light-emitting layer.

[0407] The luminescent layer may contain only one compound M2, or it may contain two or more compounds M2. The luminescent layer may contain only one compound M3, or it may contain two or more compounds M3.

[0408] Figure 4 This is a diagram showing the energy levels and energy transfer relationships of compounds M3 and M2 in the luminescent layer. Figure 4 In this diagram, 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. Figure 4 The dashed arrows in the diagram represent energy transfer between the excited states. Energy transfer occurs from the lowest excited singlet state S1 of compound M3 to the lowest excited triplet state T1 of compound M2 via Förster transfer or Dexter transfer, respectively. Furthermore, if a material with a smaller ΔST(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 via thermal energy. As a result, fluorescence emission from the lowest excited singlet state S1 of compound M2 can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal efficiency can theoretically be increased to 100%.

[0409] The organic EL element of this embodiment contains a delayed fluorescence compound M2 and a compound M3 (represented by the general formula (100)) having a singlet energy greater than that of the compound M2 in the light-emitting layer.

[0410] The organic EL element of this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0411] The structure of organic EL elements will be further explained.

[0412] (Substrate) The substrate is used as a support for organic EL (electro-optical) devices. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. Flexible substrates are (flexible) substrates that can be bent; examples include plastic substrates. Materials used to form plastic substrates include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.

[0413] (anode) The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), silicon- or silicon-oxide-containing indium tin oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include 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 metallic materials (e.g., titanium nitride).

[0414] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Furthermore, for indium oxide containing tungsten oxide and zinc oxide, it can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. In addition, it can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, etc.

[0415] In the EL layer formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that is independent of the work function of the anode and is easy to inject holes (cavities). Therefore, materials that can be used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0416] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table that have low work functions, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca) and strontium (Sr) and their alloys (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb) and their alloys. Furthermore, when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Moreover, when using silver paste, coating or inkjet methods can be used.

[0417] (cathode) The cathode is preferably a metal, alloy, conductive compound, or mixture thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them.

[0418] Furthermore, when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[0419] Furthermore, by incorporating an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[0420] (hole injection layer) A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0421] In addition, examples of substances with high hole injection potential include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylamino)-[N-(4-diphenylamino)-[N-[N-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino]biphenyl (DNTPD). Aromatic amine compounds such as [phenyl]-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[0422] Furthermore, as substances with high hole injection capability, polymeric compounds (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymeric compounds with added acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0423] (Hole transport layer) The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, and anthracene derivatives can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N Aromatic amine compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (DFLDPBi), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (BSPB) are mentioned here. -6 cm 2 / (V) Substances with a hole mobility of s or higher.

[0424] The hole transport layer can use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnt. Polymers such as poly(N-vinylcarbazole) (PVK) or poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[0425] However, any material other than electrons can be used, as long as it has a higher hole transport capacity than electrons. Furthermore, the layer containing the material with high hole transport capacity can be not only a single layer, but also a layer obtained by stacking two or more layers of the aforementioned material.

[0426] When configuring two or more hole transport layers, it is preferable to configure a material with a larger bandgap on the side closer to the light-emitting layer. HT-2, used in the embodiments described later, is an example of such a material.

[0427] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport properties. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can preferably be used. The substances mentioned herein mainly have a 10 -6 cm 2 / (V) Materials with an electron mobility of s) or higher. Furthermore, any material whose electron transport is higher than its hole transport can be used as the electron transport layer, except for those mentioned above. Moreover, the electron transport layer can be a single layer or composed of two or more layers of the aforementioned materials stacked together.

[0428] In addition, polymeric compounds can be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[0429] (Electron injection layer) The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. In addition, materials obtained by containing alkali metals, alkaline earth metals, or their compounds in a substance with electron transport properties can be used, specifically materials obtained by containing magnesium (Mg) in Alq. Furthermore, in this case, electron injection from the cathode can be performed more efficiently.

[0430] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material generates electrons in the organic compound through the electron donor, thus exhibiting good electron injection and electron transport properties. In this case, the organic compound is preferably a material with good electron transport properties, specifically, substances constituting the aforementioned electron transport layer (metal complexes or heteroaromatic compounds, etc.) can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Furthermore, alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, barium oxides, etc. In addition, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[0431] (Layer formation method) The method for forming each layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. Known methods such as dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as spin coating, dip coating, flow coating, and inkjet coating can be used.

[0432] (film thickness) The thickness of each organic layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. However, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a higher applied voltage is required and the efficiency will be reduced. Therefore, the preferred thickness is usually in the range of several nm to 1 μm.

[0433] [Second Implementation] The structure of the organic EL element according to the second embodiment will be described. In the description of the second embodiment, the same reference numerals and names are given to the same components as in the first embodiment, and descriptions are omitted or simplified. Furthermore, in the second embodiment, the same materials and compounds as those described in the first embodiment can be used for materials and compounds not specifically mentioned.

[0434] The organic EL element of the second embodiment differs from the organic EL element of the first embodiment in that the light-emitting layer also contains a fluorescent compound M1. Otherwise, it is the same as the first embodiment.

[0435] That is, in the second embodiment, the luminescent layer comprises compound M3 represented by the general formula (100), compound M2 with delayed fluorescence, and compound M1 with fluorescence.

[0436] In this scheme, compound M1 is preferably a dopant material, compound M2 is preferably a host material, and compound M3 is preferably a host material. Sometimes, one of compounds M2 and M3 is referred to as the first host material, and the other as the second host material.

[0437] (Compound M1) The light-emitting layer in this embodiment contains a fluorescent compound M1.

[0438] The compound M1 in this embodiment is not a phosphorescent metal complex. Preferably, the compound M1 in this embodiment is not a heavy metal complex. Furthermore, the compound M1 in this embodiment is preferably not a metal complex.

[0439] As compound M1 in this embodiment, a fluorescent material can be used. Specifically, examples of fluorescent materials include, for instance, bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminophenanthrene derivatives, aryl-substituted phenanthrene derivatives, bisarylaminofluoranthracene derivatives, aryl-substituted fluoranthracene derivatives, indene-perylene derivatives, acenaphthene-fluoranthracene derivatives, compounds containing boron atoms, pyrrole methylene boron complexes, compounds having a pyrrole methylene skeleton, metal complexes of compounds having a pyrrole methylene skeleton, diketopyrrole derivatives, perylene derivatives, and tetraphenyl derivatives.

[0440] The compound M1 in this embodiment is preferably a compound represented by the following general formula (20).

[0441]

Chemistry 112

[0442] In the general formula (20), X is a nitrogen atom or a carbon atom bonded to Y. Y is a hydrogen atom or a substituent. R 21 ~R 26 Each is independently a hydrogen atom or a substituent, or R 21 and R 22group, R 22 and R 23 group, R 24 and R 25 The group, and R 25 and R 26 A ring is formed by bonding any one or more groups within a group together. Y and R as substituents 21 ~R 26 Independently from Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted haloalkoxy groups with 1 to 30 carbon atoms Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms, Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms Halogen atoms, carboxyl, Substituted or unsubstituted ester groups Substituted or unsubstituted carbamoyl group, Substituted or unsubstituted amino groups Nitro, cyano, Substituted or unsubstituted silyl groups, and Selected from the group consisting of substituted or unsubstituted siloxanes. Z 21 and Z 22 Each is an independent substituent, or Z 21 and Z 22 They bond together to form a ring. Z as a substituent 21 and Z 22 Independently from Halogen atoms, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, and Selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms in a cyclic structure.

[0443] In the general formula (20), for example, in R 25 and R 26 When the groups bond together to form a ring, compound M1 is represented by the following general formula (21).

[0444]

Chemistry 113

[0445] In the general formula (21), X, Y, R 21 ~R 24 Z 21 and Z 22 respectively with X, Y, R in the general formula (20) 21 ~R 24 Z 21 and Z 22 Synonyms, R 27 ~R 30 Each can be an independent hydrogen atom or a substituent, as R. 27 ~R 30 Substituents in the case of substituents, and the substituents of R 21 ~R 24 The listed substituents are synonyms.

[0446] In the general formula (20), in Z 21 and Z 22 When the compounds bond together to form a ring, compound M1 is represented, for example, by the following general formula (20A) or the following general formula (20B). However, compound M1 is not limited to the following structures.

[0447]

Chemistry 114

[0448] In the general formula (20A), X, Y, and R 21 ~R 26 respectively with X, Y and R in the general formula (20) 21 ~R 26 Synonyms, R 1A Each can be an independent hydrogen atom or a substituent, as R. 1A Substituents in the case of substituents, and the substituents of R 21 ~R26 The example substituents are synonyms, and n3 is 4.

[0449] In the general formula (20B), X, Y, and R 21 ~R 26 respectively with X, Y and R in the general formula (20) 21 ~R 26 Synonyms, R 1B Each can be an independent hydrogen atom or a substituent, as R. 1B Substituents in the case of substituents, and the substituents of R 21 ~R 26 The example substituents are synonyms, and n4 is 4.

[0450] Z 21 and Z 22 At least one of them (preferably Z) 21 and Z 22 Preferably, the group is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted cyclic aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, and substituted or unsubstituted cyclic aryloxy groups having 6 to 30 carbon atoms.

[0451] Z 21 and Z 22 At least one of them is more preferably a group selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms obtained by substituted with a fluorine atom, an aryloxy group having 6 to 30 cyclic carbon atoms obtained by substituted with a fluorine atom, and an aryloxy group having 6 to 30 cyclic carbon atoms obtained by substituted with a fluoroalkyl group having 1 to 30 carbon atoms.

[0452] Z is further preferred. 21 and Z 22 At least one of them is an alkoxy group having 1 to 30 carbon atoms obtained by substitution with a fluorine atom, more preferably Z. 21 and Z 22 An alkoxy group having 1 to 30 carbon atoms obtained by substitution with a fluorine atom.

[0453] Z is also preferred 21 and Z 22 They are the same group.

[0454] On the other hand, the Z is also preferred. 21 and the Z 22 At least one of them is a fluorine atom, more preferably the Z atom. 21 and the Z 22 It is a fluorine atom.

[0455] Furthermore, the Z is preferred. 21 and the Z 22 At least one of them is a group represented by the following general formula (20a).

[0456]

Chemical 115

[0457] In the general formula (20a), 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 cyclic aryl group having 6 to 12 carbon atoms; L2 is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms; m is 0, 1, 2, 3, 4, 5, 6, or 7. When m is 2, 3, 4, 5, 6, or 7, the multiple L2s may be the same or different from each other. m is preferably 0, 1, or 2. When m is 0, A is directly bonded to O (oxygen atom).

[0458] In the general formula (20), Z 21 and Z 22 In the case where the group is represented by the general formula (20a), compound M1 is a compound represented by the following general formula (22).

[0459] Compound M1 is also preferably a compound represented by the following general formula (22).

[0460]

Chemistry 116

[0461] In the general formula (22), X and X' are carbon atoms bonded to Y, and R' ..."""""'"""""""""""""""" "" """ """ """ """ """ """" """" """"" " 21 ~R 26 respectively with X, Y, R in the general formula (20) 21 ~R 26 Synonyms. A 21 And A 22 The term L is synonymous with A in the general formula (20a) and can be the same as or different from each other. 21 and L 22 Synonymous with L2 in the general formula (20a), they may be the same as or different from each other. m1 and m2 are independently 0, 1, 2, 3, 4, 5, 6 or 7, preferably 0, 1 or 2. When m1 is 2, 3, 4, 5, 6 or 7, multiple L 21 Whether they are the same or different, multiple Ls are considered when m2 is 2, 3, 4, 5, 6, or 7. 22 They are the same or different. When m1 is 0, A 21 A is directly bonded to O (oxygen atom), and when m2 is 0, A 22 It bonds directly with O (oxygen atom).

[0462] In the general formula (20a), at least one of A and L2 is preferably substituted with a halogen atom, more preferably with a fluorine atom.

[0463] In the general formula (20a), A is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, or a perfluoroaryl group having 6 to 12 cyclic carbon atoms, and even more preferably a perfluoroalkyl group having 1 to 6 carbon atoms.

[0464] In the general formula (20a), L2 is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms, or a perfluoroaryl group having 6 to 12 cyclic carbon atoms, and even more preferably a perfluoroalkylene group having 1 to 6 carbon atoms.

[0465] That is, the compound M1 is preferably a compound represented by the following general formula (22a).

[0466]

Chemistry 117

[0467] In the general formula (22a), X is synonymous with X in the general formula (20), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (20). R 21 ~R 26 Independently related to R in the general formula (20) 21 ~R 26 Synonyms m3 is between 0 and 4. m4 is between 0 and 4. m3 and m4 may be the same as or different from each other.

[0468] In the general formulas (20), (21), (22) and (22a), X is a carbon atom bonded to Y. Y is a hydrogen atom or a substituent. Y, as a substituent, is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, and more preferably substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms.

[0469] In the general formulas (20), (21), (22) and (22a), As a better option, the following options can be cited: X is a carbon atom bonded to Y. Y is a hydrogen atom or a substituent. Y, as a substituent, is an aryl group with 6 to 30 cyclic carbons, either substituted or unsubstituted. When Y, as a substituent, is an aryl group having 6 to 30 cyclic carbons, the substituent is: Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted haloalkoxy groups having 1 to 30 carbon atoms, or Aryl groups with 6 to 30 carbon atoms obtained by substitution with alkyl groups having 1 to 30 carbon atoms.

[0470] In compound M1, Z can be... 21 With the Z 22 They bond together to form a ring, but preferably the Z... 21 With the Z 22 They did not bond together to form a ring.

[0471] In the general formulas (20), (22) and (22a), R is preferred. 21 R 23 R 24 and R 26 At least one of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl halogroup having 1 to 30 carbon atoms.

[0472] In the general formulas (20), (22), and (22a), R is more preferably preferred. 21 R 23 R 24 and R 26 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms. In this case, R is preferred. 22 and R 25 It is a hydrogen atom.

[0473] In the general formulas (20), (22) and (22a), R is preferred. 21 R 23 R 24 and R 26 At least one of them is a substituted or unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0474] In the general formulas (20), (22), and (22a), R is more preferably preferred. 21 R 23 R 24 and R 26The aryl group is substituted or unsubstituted, with a cyclic carbon number of 6 to 30. In this case, R is preferred. 22 and R 25 It is a hydrogen atom.

[0475] In the general formulas (20), (22), and (22a), As a better option, the following options can be cited: R 21 R 23 R 24 and R 26 Each independently, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), Substituted or unsubstituted alkyl halogroups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or Aryl groups obtained by substitution with alkyl groups having 1 to 30 carbon atoms, resulting in cyclic carbon groups having 6 to 30 carbon atoms (preferably 6 to 12 carbon atoms). R 22 and R 25 It is a hydrogen atom.

[0476] In the general formula (21), R is preferred. 21 R 23 and R 24 At least one of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl halogroup having 1 to 30 carbon atoms.

[0477] In the general formula (21), R is more preferably preferred. 21 R 23 and R 24 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms. In this case, R is preferred. 22 It is a hydrogen atom.

[0478] In the general formula (21), R is preferred. 21 R 23 and R 24 At least one of them is a substituted or unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0479] In the general formula (21), R is more preferably preferred. 21 R 23 and R 24 The aryl group is substituted or unsubstituted, with a cyclic carbon number of 6 to 30. In this case, R is preferred. 22 It is a hydrogen atom.

[0480] In the general formula (21), As a better option, the following options can be cited: R 21 R 23 and R 24 Each independently, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), Substituted or unsubstituted alkyl halogroups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or Aryl groups obtained by substitution with alkyl groups having 1 to 30 carbon atoms, resulting in cyclic carbon groups having 6 to 30 carbon atoms (preferably 6 to 12 carbon atoms). R 22 It is a hydrogen atom.

[0481] In compound M1, examples of alkoxy groups substituted with fluorine atoms include: 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, 2,2,3,3,3-pentafluoro-1-propoxy, 2,2,3,3-tetrafluoro-1-propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 2,2,3,3,4,4,4-heptafluoro-1-butoxy, 2,2,3,3,4,4-hexafluoro-1-butoxy, nonafluorotert-butoxy, 2, 2,3,3,4,4,5,5,5-nonafluoropentoxy, 2,2,3,3,4,4,5,5,6,6,6-undecylfluorohexyloxy, 2,3-bis(trifluoromethyl)-2,3-butadioxy, 1,1,2,2-tetra(trifluoromethyl)ethoxy, 4,4,5,5,6,6,6-heptafluorohexane-1,2-dioxy, and 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecylfluorononane-1,2-dioxy, etc.

[0482] In compound M1, aryloxy groups obtained by substitution with fluorine atoms or by substitution with fluoroalkyl groups can be exemplified by pentafluorophenoxy, 3,4,5-trifluorophenoxy, 4-trifluoromethylphenoxy, 3,5-bistrifluoromethylphenoxy, 3-fluoro-4-trifluoromethylphenoxy, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy, 4-fluorocatechol, 4-trifluoromethylcatechol, and 3,5-bistrifluoromethylcatechol.

[0483] When compound M1 is a fluorescent compound, compound M1 is preferably a compound with a main peak wavelength of 400 nm to 700 nm.

[0484] In this specification, the main peak wavelength refers to the wavelength at which the measured compound is measured at 10 nm. -6 10 moles per liter or more -5The fluorescence intensity of a toluene solution dissolved at a concentration below mol / L was measured at the wavelength of the peak fluorescence spectrum. The measuring apparatus used was a spectrophotometer (Hitachi High-Tech Co., Ltd., F-7000).

[0485] Compound M1 preferably exhibits red or green luminescence.

[0486] In this specification, red emission refers to emission with the main peak wavelength of the fluorescence spectrum in the range of 600 nm to 660 nm.

[0487] 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 even more preferably 610 nm or more and 630 nm or less.

[0488] In this specification, green luminescence refers to luminescence with the main peak wavelength of the fluorescence spectrum in the range of 500 nm to 560 nm.

[0489] When compound M1 is a green fluorescent compound, the main peak wavelength of compound M1 is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm.

[0490] In this specification, blue emission refers to emission with the main peak wavelength of the fluorescence spectrum in the range of 430 nm to 480 nm.

[0491] 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.

[0492] The main peak wavelength of light emitted from the organic EL element is measured as described below.

[0493] The measurement was performed using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage was applied to an organic EL element to achieve a current density of 10 mA / cm². 2 The spectrophotometric emission brightness spectrum at that time.

[0494] In the obtained spectrophotometric emission brightness spectrum, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum is measured and taken as the main peak wavelength (unit: nm).

[0495] • Method for manufacturing compound M1 Compound M1 can be manufactured using known methods.

[0496] Specific examples of Compound M1 of the present embodiment are shown below. However, the present invention is not limited by these specific examples of the compounds.

[0497] In addition, the coordination bond between the boron atom and the nitrogen atom in the pyrromethene skeleton has various marking methods such as solid lines, dashed lines, arrows, or omissions. In this specification, it is represented by a solid line, or a dashed line, or omitted.

[0498]

Chemical Formula 118

[0499]

Chemical Formula 119

[0500]

Chemical Formula 120

[0501]

Chemical Formula 121

[0502]

Chemical Formula 122

[0503]

Chemical Formula 123

[0504]

Chemical Formula 124

[0505] <Relationship between Compound M3, Compound M2, and Compound M1 in the light-emitting layer> In the organic EL device of the present 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 (Formula 2).

[0506] S1(M2) > S1(M1) (Formula 2) 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.

[0507] 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 (Formula 2A).

[0508] S1(M3) > S1(M2) > S1(M1) … (Formula 2A) When the organic EL device of the present embodiment emits light, it is preferable that in the light-emitting layer, mainly the fluorescent light-emitting Compound M1 emits light.

[0509] Preferably, the organic EL element in this embodiment emits red or green light.

[0510] • The content of compounds in the luminescent layer The content of compounds M3, M2 and M1 contained in the light-emitting layer is preferably within, for example, the following range.

[0511] The content of compound M3 is preferably 10% by mass or more and 80% by mass or less.

[0512] The content 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 even more preferably 20% by mass or more and 60% by mass or less.

[0513] The content of compound M1 is preferably 0.01% by mass or more and 10% by mass, more preferably 0.01% by mass or more and 5% by mass, and even more preferably 0.01% by mass or more and 1% by mass.

[0514] The maximum allowed percentage of the total content of compounds M3, M2, and M1 in the luminescent layer is 100% by mass. Furthermore, it is not excluded that the luminescent layer in this embodiment may contain materials other than compounds M3, M2, and M1.

[0515] The luminescent layer may contain only one compound M3, or it may contain two or more compounds M3. The luminescent layer may contain only one compound M2, or it may contain two or more compounds M2. The luminescent layer may contain only one compound M1, or it may contain two or more compounds M1.

[0516] Figure 5 This is a diagram illustrating an example of the energy level relationships among compounds M3, M2, and M1 in the luminescent layer. Figure 5 In this diagram, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of compound M1, and T1 (M1) represents the lowest excited triplet state of compound M1. 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. Figure 5 The dashed arrows from S1(M2) to S1(M1) represent Foster-type energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1.

[0517] like Figure 5As shown, if a compound with a smaller ΔST (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) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of compound M2 to the Foster-type energy transfer of 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 believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0518] The organic EL element of the second embodiment includes a delayed fluorescence compound M2, a compound M3 (represented by the general formula (100)) having a singlet energy greater 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.

[0519] According to the second embodiment, high-performance organic EL elements, such as organic EL elements that emit light with a long lifetime, can be realized.

[0520] The organic EL element of the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0521] [Third Implementation Method] [Electronic Devices] The electronic device of this embodiment is equipped with an organic EL element from any of the above embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[0522] [Fourth Implementation Method] [Compound] The compound of the fourth embodiment is a compound represented by the following general formula (201), the following general formula (202), or the following general formula (203).

[0523]

Chemistry 125

[0524] In the general formula (201), X1 is an oxygen atom or a sulfur atom, n is 1, 2 or 3, k is 1, 2 or 3, m is 2, 3 or 4, k+m=5, R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and multiple R groups are such that at least one of n and k is 2 or more. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (201), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34and R 35 Each R2 can be an independent hydrogen atom or a substituent, wherein, when m is 2 or more, the multiple R2 atoms may be the same or different from each other. R 41 R 42 R 44 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 41 R 42 R 44 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms in the cyclic formation. Among them, R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0525]

Chemistry 126

[0526] In the general formula (202), X1 is an oxygen atom or a sulfur atom, n is 1, 2 or 3, k is 1, 2 or 3, m is 2, 3 or 4, k+m=5, R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and multiple R groups are such that at least one of n and k is 2 or more. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (202), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (202), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (202), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or a substituent, wherein, when m is 2 or more, the multiple R2 atoms may be the same or different from each other. R 41 R 43 R 44 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 41 R 43 R 44 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms in the cyclic formation. Among them, R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0527]

Chemistry 127

[0528] In the general formula (203), X1 is an oxygen atom or a sulfur atom, n is 1, 2 or 3, k is 1, 2 or 3, m is 2, 3 or 4, k+m=5, R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18The groups are not mutually bonded, and multiple R groups are such that at least one of n and k is 2 or more. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (203), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (203), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (203), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or a substituent, wherein, when m is 2 or more, the multiple R2 atoms may be the same or different from each other. R 42 ~R 44 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 42 ~R 44 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms in the cyclic formation. Among them, R 11 ~R 18At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

[0529] [Organic EL Components] As one embodiment of the organic EL element, it is an organic EL element obtained by replacing compound M3 in the organic EL element of the first embodiment with a compound of the fourth embodiment (a compound represented by any one of the general formulas (201) to (203)).

[0530] For example, the compounds represented by the general formulas (201) to (203) are synonymous with the compounds represented by the general formulas (201A) to (203A) exemplified as an example of compound M3 in the first embodiment.

[0531] That is, in the general formula (201), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 42 R 44 and R 45 ~R 48 respectively with X1 and R in general formula (201A) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 42 R 44 and R 45 ~R 48 Synonyms.

[0532] In the general formula (202), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 R 43 R 44 and R 45 ~R 48 respectively with X1 and R in general formula (202A) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34R 35 R 41 R 43 R 44 and R 45 ~R 48 Synonyms.

[0533] In the general formula (203), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 42 ~R 44 and R 45 ~R 48 respectively with X1 and R in general formula (203A) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 42 ~R 44 and R 45 ~R 48 Synonyms.

[0534] The compound of the fourth embodiment is a compound that enables high-performance organic EL elements, such as organic EL elements that emit light with a long lifetime.

[0535] Therefore, the organic EL element in one embodiment of the fourth method is also high-performance, for example, emitting light with a long lifespan.

[0536] [Fifth Implementation Method] [Compound] The compound of the fifth embodiment is represented by the following general formula (300).

[0537]

Chemistry 128

[0538] In the general formula (300), X1 is an oxygen atom or a sulfur atom, n is 1, 2 or 3, k is 1, 2 or 3, m is 2, 3 or 4, k+m=5, R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 can be a single bond or a linking group. When k is 2 or more, multiple L1s can be the same or different from each other. Where L1 is a single bond, n is 1. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (300), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (300), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (300), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or a substituent, wherein, when m is 2 or more, the multiple R2 atoms may be the same or different from each other. R 41 R 42 R 43 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 41 R 42 R 43 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0539] [Organic EL Components] As one embodiment of the fifth embodiment, the organic EL element is an organic EL element obtained by replacing compound M3 in the organic EL element of the first embodiment with the compound of the fifth embodiment (a compound represented by the general formula (300)).

[0540] For example, the compound represented by the general formula (300) is synonymous with the compound represented by the general formula (300A) exemplified as an example of compound M3 in the first embodiment.

[0541] That is, in the general formula (300), X1, R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 respectively with X1 and R in general formula (300A) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 Synonyms.

[0542] The compound of the fifth embodiment is a compound that enables high-performance organic EL elements, such as organic EL elements that emit light with a long lifetime.

[0543] Therefore, the organic EL element in one embodiment of the fifth method is also high-performance, for example, emitting light with a long lifespan.

[0544] Preferred embodiments of the compounds in the fourth and fifth embodiments will be described.

[0545] In the compounds of the fourth embodiment and the fifth embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in the group are bonded together to form a loop, and R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other.

[0546] In the compounds of the fourth embodiment and the fifth embodiment, R is preferred. 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other.

[0547] In the compounds of the fourth embodiment and the fifth embodiment, R2 and R are preferably preferred. 31 R 32 R 34 and R 35 It is a hydrogen atom. L1 is a single bond, or Derived from unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or A group derived from an unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

[0548] In the compounds of the fourth embodiment and the fifth embodiment, n is preferably 1 or 2, and more preferably n is 1.

[0549] In the compounds of the fourth embodiment and the fifth embodiment, k is preferably 1 or 2.

[0550] In the compounds of the fourth embodiment and the fifth embodiment, it is more preferable that n is 1 or 2 and k is 1 or 2.

[0551] In the compounds of the fourth embodiment and the fifth embodiment, R is preferred. 11 ~R 18 and R 41 ~R 48 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In the compounds of the fourth embodiment and the fifth embodiment, R is more preferred. 11 ~R 18 and R 41 ~R 48 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in the cyclic group, or a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms in the cyclic group. In the compounds of the fourth embodiment and the fifth embodiment, R is further preferred. 11 ~R 18 and R 41 ~R 48 Each aryl group is independently composed of hydrogen atoms, or is either substituted or unsubstituted and consists of 6 to 30 cyclic carbon atoms. In the compounds of the fourth embodiment and the fifth embodiment, R is further preferred. 11 ~R 18 and R 41 ~R 48 Each is a hydrogen atom, or a substituted or unsubstituted phenyl group.

[0552] In the compounds of the fourth embodiment and the fifth embodiment, R is preferred. 11 ~R 18 R is a phenyl group that is independently composed of hydrogen atoms or is either substituted or unsubstituted. 41 ~R 48 Each is an independent hydrogen atom.

[0553] In the compounds of the fourth embodiment and the fifth embodiment, L1 is preferably a single bond, or a group derived from an unsubstituted aryl group having 6 to 30 unsubstituted cyclic carbon atoms. In the compounds of the fourth embodiment and the fifth embodiment, it is more preferable that L1 is a single bond or a group derived from an unsubstituted benzene ring.

[0554] In the compounds of the fourth embodiment and the fifth embodiment, it is more preferable that L1 is a single bond.

[0555] In the compounds of the fourth embodiment and the fifth embodiment, X1 is preferably an oxygen atom.

[0556] In the compound of the fourth embodiment, R2 and R are preferred. 31 R 32 R 34 and R 35 For hydrogen atoms, n is 1 or 2, k is 1 or 2, R 11 ~R 18 and R 41 ~R 48 Each aryl group is independently composed of hydrogen atoms, or is either substituted or unsubstituted and consists of 6 to 30 cyclic carbon atoms. Among them, R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other. L1 is a single bond, or a group derived from an unsubstituted aryl group with 6 to 30 unsubstituted cyclic carbon atoms.

[0557] In the compounds of the fourth embodiment, R2 and R are also preferred. 31 R 32 R 34 and R 35 For hydrogen atoms, n is 1 or 2, k is 1 or 2, R 11 ~R 18 R is a phenyl group that is independently composed of hydrogen atoms, or is either substituted or unsubstituted. 41 ~R 48 L1 is a hydrogen atom and L1 is a single bond.

[0558] In the compound of the fifth embodiment, R2 and R are preferred. 31 R32 R 34 and R 35 For hydrogen atoms, n is 1 or 2, k is 1 or 2, R 11 ~R 18 R 41 ~R 43 and R 45 ~R 48 Each aryl group is independently composed of hydrogen atoms, or is either substituted or unsubstituted and consists of 6 to 30 cyclic carbon atoms. Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 41 and R 42 group, R 42 and R 43 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups are not bonded to each other, L1 is a single bond, or is a group derived from an unsubstituted aryl group with 6 to 30 cyclic carbons.

[0559] In the compounds of the fifth embodiment, R2 and R are also preferred. 31 R 32 R 34 and R 35 For hydrogen atoms, n is 1 or 2, k is 1 or 2, R 11 ~R 18 Each phenyl group is independently composed of a hydrogen atom, or is either substituted or unsubstituted. Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups do not bond with each other. R 41 ~R 43 and R 45 ~R 48 L1 is a hydrogen atom and L1 is a single bond.

[0560] [Fifth Implementation Method A] [Compound] The compound of the fifth embodiment A is a compound represented by any one of the following general formulas (501) to (514).

[0561]

Chemistry 129

[0562]

Chemistry 130

[0563] [Organic EL Components] The organic EL element of the fifth embodiment A is an organic EL element obtained by replacing compound M3 in the organic EL element of the first embodiment with a compound of the fifth embodiment A (a compound represented by any one of the general formulas (501) to (514)).

[0564] The compound represented by the general formulas (501) to (514) is an example of compound M3 in the first embodiment.

[0565] The compound of the fifth embodiment A is a compound that enables high-performance organic EL elements, such as organic EL elements that emit light with long lifetime.

[0566] Therefore, the organic EL element, as one aspect of the fifth embodiment A, is also high-performance, for example, emitting light with a long lifespan.

[0567] [Sixth Implementation Method] Materials for Organic EL Components The organic EL element material of the sixth embodiment includes at least one of the compounds of the fourth embodiment, the fifth embodiment, and the fifth embodiment A.

[0568] That is, the organic EL element material of the sixth embodiment includes at least one of the compounds represented by any one of the general formulas (201) to (203), (300) and (501) to (514).

[0569] According to the material for organic EL elements in the sixth embodiment, high-performance organic EL elements, such as organic EL elements that emit light with long lifespan, and electronic devices can be realized.

[0570] Furthermore, the organic EL element material of the sixth embodiment may also contain other compounds. In the case where the organic EL element material of the sixth embodiment further contains other compounds, these other compounds may be solid or liquid.

[0571] [Variations on the implementation method] Furthermore, the present invention is not limited to the above-described embodiments, and any modifications or improvements made within the scope of achieving the objectives of the present invention are included within the scope of the present invention.

[0572] For example, the light-emitting layer is not limited to a single layer; multiple light-emitting layers can be stacked. In the case of an organic EL device having multiple light-emitting layers, it is sufficient as long as at least one light-emitting layer meets the conditions described in the above embodiments. For example, the other light-emitting layers can be either fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize the emission caused by electron migration directly from the triplet excited state to the ground state.

[0573] Furthermore, in the case of an organic EL element having multiple light-emitting layers, these light-emitting layers can be arranged adjacent to each other, or they can be a so-called tandem organic EL element consisting of multiple light-emitting units stacked with an intermediate layer in between.

[0574] Alternatively, a blocking layer may be disposed adjacent to at least one of the anode and cathode sides of the light-emitting layer. The blocking layer is preferably grounded to the light-emitting layer to block at least one of holes, electrons, and excitons.

[0575] For example, when a barrier layer is grounded on the cathode side of the light-emitting layer, the barrier layer prevents the transport of electrons and prevents holes from reaching the cathode side layer (e.g., the electron transport layer) of the barrier layer. In the case of an organic EL element that includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer.

[0576] Furthermore, when a barrier layer is grounded on the anode side of the light-emitting layer, the barrier layer prevents the transport of holes and prevents electrons from reaching the anode side layer of the barrier layer (e.g., a hole transport layer). In the case of an organic EL element that includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer.

[0577] Alternatively, the blocking layer can be disposed adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. This prevents excitons generated in the light-emitting layer from moving to the electrode side of the blocking layer (e.g., electron transport layers and hole transport layers).

[0578] Preferably, the light-emitting layer is bonded to the blocking layer.

[0579] In addition, the specific structure and shape in the implementation of the present invention may adopt other structures within the scope of achieving the purpose of the present invention.

[0580] In this specification, the numerical range indicated by “~” refers to the range included by taking the value before “~” as the lower limit and the value after “~” as the upper limit.

[0581] In this specification, the mutual bonding of Rx and Ry to form a ring means, for example, that Rx and Ry contain carbon, nitrogen, oxygen, sulfur, or silicon atoms, and that the atoms in Rx (carbon, nitrogen, oxygen, sulfur, or silicon) are bonded to the atoms in Ry (carbon, nitrogen, oxygen, sulfur, or silicon) via single, double, triple, or divalent connecting groups to form a ring with five or more cyclic atoms (specifically, a heterocycle or aromatic hydrocarbon ring). x is a number, a letter, or a combination of numbers and letters. y is a number, a letter, or a combination of numbers and letters.

[0582] There are no particular limitations on the divalent linking group, for example -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa-, and groups obtained by combining two or more of these linking groups.

[0583] As a specific example of a heterocycle, one can cite the ring structure (heterocycle) obtained by removing chemical bonds from the "heteroaryl Sub2" illustrated in the "Explanation of Substituents in the General Formula" described later. These heterocycles may have substituents.

[0584] As a specific example of an aromatic hydrocarbon ring, one can cite the ring structure (aromatic hydrocarbon ring) obtained by removing chemical bonds from the "aryl Sub1" illustrated in the "Explanation of Substituents in the General Formula" described later. These aromatic hydrocarbon rings may have substituents.

[0585] Examples of Ra include, for instance, alkyl Sub3 with 1 to 30 carbon atoms that are substituted or unsubstituted, aryl Sub1 with 6 to 30 carbon atoms that are substituted or unsubstituted, and heteroaryl Sub2 with 5 to 30 carbon atoms that are substituted or unsubstituted, as illustrated in the “Explanation of Substituents in the General Formula” described later.

[0586] For example, the formation of a ring by mutual bonding of Rx and Ry means that: in the molecular structure represented by the following general formula (E1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring (ring structure) E represented by general formula (E2); in the molecular structure represented by general formula (F1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring F represented by general formula (F2); in the molecular structure represented by general formula (G1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring G represented by general formula (G2); in the molecular structure represented by general formula (H1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring H represented by general formula (H2); and in the molecular structure represented by general formula (I1), the atoms contained in Rx1 and the atoms contained in Ry1 form a ring I represented by general formula (I2).

[0587] In general formulas (E1) to (I1), * independently represents the position of a bond with other atoms in a molecule. The two * in general formula (E1) correspond to the two * in general formula (E2), the two * in general formula (F1) correspond to the two * in general formula (F2), the two * in general formula (G1) correspond to the two * in general formula (G2), the two * in general formula (H1) correspond to the two * in general formula (H2), and the two * in general formula (I1) correspond to the two * in general formula (I2).

[0588]

Chemistry 131

[0589]

Chemistry 132

[0590] In the molecular structures represented by general formulas (E2) to (I2), E to I represent ring structures (rings with 5 or more ring atoms). In general formulas (E2) to (I2), * independently represents the position of bonding with other atoms in a molecule. The two * in general formula (E2) correspond to the two * in general formula (E1). Similarly, the two * in general formulas (F2) to (I2) also correspond to the two * in general formulas (F1) to (I1).

[0591] For example, in general formula (E1), where Rx1 and Ry1 are bonded together to form ring E in general formula (E2), and ring E is an unsubstituted benzene ring, the molecular structure represented by general formula (E1) becomes the molecular structure represented by the following general formula (E3). Here, the two asterisks in general formula (E3) correspond independently to the two asterisks in general formula (E2) and general formula (E1), respectively.

[0592] For example, in general formula (E1), where Rx1 and Ry1 are bonded together to form ring E in general formula (E2), and ring E is an unsubstituted pyrrole ring, the molecular structure represented by general formula (E1) becomes the molecular structure represented by the following general formula (E4). Here, the two asterisks in general formula (E4) correspond independently to the two asterisks in general formula (E2) and general formula (E1), respectively. In general formulas (E3) and (E4), asterisks independently represent the positions in a molecule that are bonded to other atoms.

[0593]

Chemistry 133

[0594] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the atoms constituting the ring itself in a compound with a cyclic structure formed by atomic bonds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming the ring" as used below is the same unless otherwise specified. For example, the number of carbon atoms forming the ring of a benzene ring is 6, the number of carbon atoms forming the ring of a naphthalene ring is 10, the number of carbon atoms forming the ring of a pyridyl group is 5, and the number of carbon atoms forming the ring of a furanyl group is 4. Furthermore, when an alkyl group, for example, is substituted on a benzene or naphthalene ring, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms forming the ring. Additionally, when a fluorene ring, for example, is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms in the fluorene ring as a substituent is not included in the number of carbon atoms forming the ring.

[0595] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, aggregated rings, carbocyclic compounds, heterocyclic compounds) that form a cyclic structure (e.g., monocyclic, fused-ring, aggregated rings) by atomic bonds. Atoms that do not constitute a ring, and atoms contained in substituents when the ring is substituted, are not included in the number of cyclic atoms. This also applies to the "number of cyclic atoms" described below unless otherwise specified. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. Hydrogen atoms bonded to the carbon atoms of the pyridine or quinazoline rings, and atoms constituting substituents, are not included in the number of cyclic atoms. Furthermore, in cases where a fluorene ring is bonded to a fluorene ring as a substituent (including spirofluorene rings), the number of atoms of the fluorene ring as a substituent is not included in the number of cyclic atoms.

[0596] • Explanation of each substituent in the general formulas in this specification (Explanation of each substituent) In this specification, aryl (sometimes referred to as aromatic hydrocarbon group) is, for example, arylSub1, which is at least one group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluorenyl, pyrene, phenyl, fluoranyl, benzo[a]anthryl, benzo[c]phenanthryl, triphenylene, benzo[k]fluoranyl, benzo[g]phenyl, benzo[b]triphenylene, picenyl, and perylenyl.

[0597] The aryl Sub1 in this specification preferably has 6 to 30 carbon atoms in its ring, more preferably 6 to 20, even more preferably 6 to 14, and still more preferably 6 to 12. Among the above-mentioned aryl Sub1, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, and fluorenyl are preferred. For 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, and 4-fluorenyl, the carbon atom at position 9 is preferably substituted by a substituted or unsubstituted alkyl Sub3 or a substituted or unsubstituted aryl Sub1 as described later in this specification.

[0598] In this specification, the heteroaryl group (sometimes referred to as a heterocyclic group, heteroaromatic cyclic group, or aromatic heterocyclic group) is, for example, the heterocyclic group Sub2. The heterocyclic group Sub2 is a group comprising at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium, and germanium atoms as a heteroatom. Preferably, the heterocyclic group Sub2 comprises at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom.

[0599] The heterocyclic group Sub2 in this specification includes, for example, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthroxolinyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indoleyl, benzimidazolyl, indazolyl, imidazopyridyl, benzotriazolyl, carbazole, furanyl, thiophene, and oxazolyl. The group selected from the group consisting of , thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzoisoxazolyl, benzoisothiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothiaphenyl, piperidinyl, pyrrolyl, piperazine, morpholinyl, phenazinyl, phenothiazinyl, and phenothiazinyl.

[0600] The heterocyclic group Sub2 in this specification preferably has 5 to 30 cyclic atoms, more preferably 5 to 20, and even more preferably 5 to 14. Among the above-mentioned heterocyclic groups Sub2, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, and 9-carbazoleyl are even more preferred. Regarding 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, and 4-carbazoleyl, the nitrogen atom at the 9-position is preferably substituted by a substituted or unsubstituted aryl group Sub1 or a substituted or unsubstituted heterocyclic group Sub2 as described in this specification.

[0601] Furthermore, in this specification, the heterocyclic group Sub2 may also be a group derived from the local structure represented by the following general formulas (XY-1) to (XY-18).

[0602]

Chemistry 134

[0603]

Chemistry 135

[0604]

Transformation 136

[0605] In the general formulas (XY-1) to (XY-18), X A and Y A Each atom is an independent heteroatom, preferably an oxygen atom, sulfur atom, selenium atom, silicon atom, or germanium atom. The local structure represented by the general formula (XY-1) to (XY-18) has chemical bonds at any position to form a heterocyclic group, which may have substituents.

[0606] Furthermore, in this specification, the heterocyclic group Sub2 can also be represented by the following general formulas (XY-19) to (XY-22). Additionally, the positions of the chemical bonds can be appropriately changed.

[0607]

Chemistry 137

[0608] The alkyl group in this specification can be any of a straight-chain alkyl group, a branched alkyl group, or a cyclic alkyl group.

[0609] In this specification, alkyl groups are, for example, alkyl Sub3.

[0610] In this specification, straight-chain alkyl groups are, for example, straight-chain alkyl sub. 31 .

[0611] In this specification, branched alkyl groups are, for example, branched alkyl subs. 32 .

[0612] The cyclic alkyl group in this specification is, for example, a cyclic alkyl sub. 33 .

[0613] Alkyl Sub3, for example, is derived from straight-chain alkyl Sub 31 Branched alkyl Sub 32 and cyclic alkyl sub 33 At least one group selected from the group constitutes the composition.

[0614] Straight-chain alkyl sub 31 or branched alkyl sub 32 For example, at least one group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl.

[0615] The straight-chain alkyl sub in this specification 31 or branched alkyl sub 32 The number of carbon atoms is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and still more preferably 1 to 6. As the above-mentioned straight-chain alkyl Sub 31 or branched alkyl sub 32 More preferably, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, pentyl, isopentyl, and neopentyl.

[0616] The cyclic alkyl sub in this specification 33 For example, cycloalkyl Sub 331 .

[0617] The cycloalkyl sub in this specification 331 For example, at least one group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, and norbornyl. Cycloalkyl Sub 331 The preferred number of carbon atoms in the cyclic compound is 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and even more preferably 5 to 8. In the cycloalkyl sub 331 More preferably, cyclopentyl or cyclohexyl.

[0618] In this specification, alkyl halogens are, for example, alkyl halogens Sub4, which are alkyl groups obtained by substituting alkyl Sub3 with one or more halogen atoms, preferably fluorine atoms.

[0619] The alkyl halogroup Sub4 in this specification is, for example, selected from at least one group selected from the group consisting of fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethylmethyl, trifluoroethyl and pentafluoroethyl.

[0620] In this specification, substituted silyl groups are, for example, substituted silyl Sub5, which is derived from alkyl silyl Sub... 51 and arylsilyl Sub 52 At least one group selected from the group constitutes the composition.

[0621] The alkylsilyl sub in this specification 51 For example, a trialkylsilyl sub-sub-containing alkyl Sub3 as described above. 511 .

[0622] Trialkylsilyl Sub 511 For example, at least one group selected from the group consisting of trimethylsilyl, triethylsilyl, tri-n-butylsilyl, tri-n-octylsilyl, triisobutylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-propylsilyl, dimethyl-n-butylsilyl, dimethyl-tert-butylsilyl, diethylisopropylsilyl, vinyldimethylsilyl, propyldimethylsilyl, and triisopropylsilyl. Trialkylsilyl Sub 511 The three alkyl groups Sub3 in the formula can be the same as or different from each other.

[0623] The arylsilyl sub in this specification 52 For example, from dialkylarylsilylsub 521 alkyl diarylsilyl sub 522 and triarylsilyl Sub 523 At least one group selected from the group constitutes the composition.

[0624] Dialkylarylsilyl Sub 521 For example, a dialkylarylsilyl group having two of the above-mentioned alkyl groups Sub3 and one of the above-mentioned aryl groups Sub1. Dialkylarylsilyl Sub 521 The preferred number of carbon atoms is 8 to 30.

[0625] Alkyl diarylsilyl sub 522For example, an alkyl diarylsilyl group having one of the above-mentioned alkyl groups Sub3 and two of the above-mentioned aryl groups Sub1. Alkyl diarylsilyl Sub 522 The preferred number of carbon atoms is 13 to 30.

[0626] Triarylsilyl Sub 523 For example, a triarylsilyl group having three of the above-mentioned aryl groups Sub1. Triarylsilyl Sub 523 The preferred number of carbon atoms is 18 to 30.

[0627] The substituted or unsubstituted alkyl sulfonyl group in this specification is, for example, alkyl sulfonyl Sub6, alkyl sulfonyl Sub6 with -SO2R w express. -SO2R w R in w The above alkyl group Sub3 is indicated as substituted or unsubstituted.

[0628] In this specification, aralkyl (sometimes referred to as arylalkyl) is, for example, aralkyl Sub7. The aryl group in aralkyl Sub7 includes, for example, at least one of the aryl Sub1 and the heteroaryl Sub2 described above.

[0629] In this specification, the aralkyl Sub7 is preferably a group having an aryl Sub1, denoted as -Z3-Z4. Z3 is, for example, an alkylene group corresponding to the aforementioned alkyl Sub3. Z4 is, for example, the aforementioned aryl Sub1. Preferably, the aryl portion of the aralkyl Sub7 has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl portion has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6). The aralkyl group Sub7 is, for example, at least one group selected from the group consisting of benzyl, 2-phenylpropane-2-yl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0630] In this specification, the alkoxy group is, for example, alkoxy Sub8, which is represented as -OZ1. Z1 is, for example, the aforementioned alkyl Sub3. Alkoxy Sub8 is, for example, at least one group selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. The number of carbon atoms in the alkoxy Sub8 is preferably 1 to 30, more preferably 1 to 20.

[0631] In this specification, the haloalkoxy group is, for example, haloalkoxy Sub9, which is an alkoxy group obtained by substituting the above-mentioned alkoxy Sub8 with one or more halogen atoms, preferably fluorine atoms.

[0632] The aryloxy group (sometimes called arylalkoxy) in this specification is, for example, arylalkoxy Sub. 10 Arylalkoxy Sub 10 The aryl group in the aryl group includes at least one of aryl Sub1 and heteroaryl Sub2.

[0633] The arylalkoxy Sub in this specification 10 Represented as -OZ2. This Z2 is, for example, arylSub1 or heteroarylSub2. ArylalkoxySub 10 The preferred number of carbon atoms in the cyclic compound is 6 to 30, more preferably 6 to 20. As this arylalkoxy sub 10 For example, phenoxy groups can be cited.

[0634] The substituted amino group in this specification is, for example, a substituted amino group Sub. 11 Subsubstituted amino groups 11 For example, from arylamino Sub 111 and alkylamino Sub 112 At least one group selected from the group constitutes the composition.

[0635] Arylamino Sub 111 Represented as -NHR V1 , or -N(R) V1 2. The R V1 For example, arylSub1. -N(R) V1 The two R's in 2) V1 Same or different.

[0636] Alkylamino Sub 112 Represented as -NHR V2 , or -N(R) V2 2. The R V2 For example, alkyl Sub3-N(R) V2 The two R's in 2) V2 Same or different.

[0637] In this specification, the alkenyl group is, for example, an alkenyl sub. 12 alkenyl Sub 12 It is any one of straight-chain or branched chains, for example, at least one group selected from the group consisting of vinyl, propenyl, butenyl, oleenyl, eicosaptenyl, docosahexaenoyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl and 2-phenyl-2-propenyl.

[0638] In this specification, the alkynyl group is, for example, alkynyl group Sub. 13 , acetylenic Sub 13 It can be either straight-chain or branched, for example, at least one group selected from the group consisting of ethynyl, propynyl and 2-phenylethynyl.

[0639] In this specification, the alkylthio group is, for example, alkylthio group Sub. 14 .

[0640] Alkylthiosub 14 Represented as -SR V3 The R V3 For example, alkyl Sub3. Alkylthio Sub 14 The number of carbon atoms is preferably 1 to 30, more preferably 1 to 20.

[0641] In this specification, the aryl thio group is, for example, aryl thio group Sub. 15 .

[0642] Arylthiosub 15 Represented as -SR V4 The R V4 For example, aryl Sub1. Arylthio Sub 15 The number of cyclic carbons is preferably 6 to 30, more preferably 6 to 20.

[0643] Examples of halogen atoms in this specification include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms being preferred.

[0644] The substituted phosphine group in this specification is, for example, a substituted phosphine group Sub. 16 , substituted phosphine-based Sub 16 For example, phenylphosphine group.

[0645] In this specification, aryl carbonyl groups are, for example, aryl carbonyl groups (Sub). 17 aryl carbonyl Sub 17 It is represented as -COY'. The Y' is, for example, aryl Sub1. The aryl carbonyl Sub in this specification... 17 For example, at least one group selected from the group consisting of phenylcarbonyl, diphenylcarbonyl, naphthylcarbonyl and triphenylcarbonyl.

[0646] In this specification, the acyl group, for example, is an acyl group (Sub). 18 Acyl Sub 18 It is represented as -COR'. The R' is, for example, an alkyl Sub3. The acyl Sub in this specification... 18 For example, at least one group selected from the group consisting of acetyl and propionyl.

[0647] The substituted phosphoryl group in this specification is, for example, a substituted phosphoryl group Sub. 19 Subsubstituted phosphoryl group 19 It is represented by the following general formula (P).

[0648]

Chemistry 138

[0649] In the general formula (P), Ar P1 and Ar P2 It is any substituent selected from the group consisting of the above-mentioned alkyl Sub3 and the above-mentioned aryl Sub1.

[0650] In this specification, the ester group is, for example, the ester group Sub. 20 ester group Sub 20 For example, alkyl ester groups.

[0651] In this specification, the alkyl ester group is, for example, an alkyl ester group Sub. 201 alkyl ester group Sub 201 Represented as -C (=O) OR E R E For example, the above-mentioned alkyl Sub3, whether substituted or unsubstituted.

[0652] In this specification, siloxane alkyl groups are, for example, siloxane sub-alkyl groups. 21 Siloxane Sub 21 It is a silicon compound group obtained via an ether bond. Siloxane Sub 21 For example, trimethylsiloxane.

[0653] In this specification, the carbamoyl group is represented as -CONH2.

[0654] The substituted carbamoyl group in this specification is, for example, carbamoyl Sub. 22 Carbamoyl Sub 22 Represented as -CONH-Ar C 、or -CONH-R C Ar C For example, at least one group selected from the group consisting of substituted or unsubstituted aryl Sub1 (preferably with 6 to 10 cyclic carbon atoms) and heteroaryl Sub2 (preferably with 5 to 14 cyclic atoms). C It can be a group obtained by bonding aryl Sub1 and heteroaryl Sub2.

[0655] R C For example, the above-mentioned alkyl Sub3 (preferably with 1 to 6 carbon atoms) may be substituted or unsubstituted.

[0656] In this specification, "cyclic carbon" refers to the carbon atom that constitutes a saturated ring, unsaturated ring, or aromatic ring. "Cyclic atom" refers to the carbon atom and heteroatom that constitute a heterocycle (including saturated rings, unsaturated rings, and aromatic rings).

[0657] In addition, in this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0658] Hereinafter, alkylSub3 refers to the straight-chain alkylSub as described in the "Explanation of Substituents" section. 31 Branched alkyl Sub 32 and cyclic alkyl sub 33 One or more of the following groups.

[0659] Similarly, substituted silyl Sub5 refers to alkyl silyl Sub. 51 and arylsilyl Sub 52 One or more of the following groups.

[0660] Similarly, substituted amino Sub 11 It refers to arylamino Sub 111 and alkylamino Sub 112 One or more of the following groups.

[0661] In this specification, a substituent is referred to as "substituted or unsubstituted" in such cases, for example, substituent R. F1 , substituent R F1 From aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 Subsubstituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 Carbamoyl Sub 22 At least one group selected from the group consisting of an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxyl group, a nitro group, and a carboxyl group.

[0662] In this specification, the substituent R is used in cases of "substituted or unsubstituted". F1 It can also be diarylboronic (Ar) B1 Ar B2 B-). As the Ar B1 and Ar B2 Examples of this can be found in the aforementioned aryl Sub1. Ar B1 Ar B2 Ar in B- B1 And Ar B2 Same or different.

[0663] As a substituent R F1 Specific examples and preferred groups can be cited from the substituents in the "Description of Substituents" (e.g., aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub9). 10 Subsubstituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 and carbamoyl Sub 22 ) Specific examples and preferred groups are the same groups.

[0664] Substituent R in cases of "substituted or unsubstituted" F1 It can be derived from aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 Subsubstituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub20 Siloxane Sub 21 Carbamoyl Sub 22 At least one group selected from the group consisting of unsubstituted amino, unsubstituted silyl, halogen atom, cyano, hydroxyl, nitro and carboxyl (hereinafter also referred to as substituent R) F2 Further substitution. In addition, these multiple substituents R F2 They can also bond together to form a ring.

[0665] In the case of "substituted or unsubstituted", "unsubstituted" means not substituted by the substituent R. F1 It is replaced by a hydrogen atom and bonded together.

[0666] Furthermore, in this specification, the phrase "a ZZ group with XX to YY carbons, whether substituted or unsubstituted" refers to the number of carbons when the ZZ group is unsubstituted, and the number of carbons when there is no substitution (R). F1 The number of carbon atoms.

[0667] In this specification, the phrase "ZZ group with XX to YY atoms, whether substituted or unsubstituted" refers to the number of atoms in the unsubstituted ZZ group, and the number of atoms in the unsubstituted ZZ group. F1 The number of atoms.

[0668] The same applies to the cases of "substituted or unsubstituted" in the compounds or their partial structures described in this specification.

[0669] 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.

[0670] In this specification, the aromatic hydrocarbon group in the linking group can be, for example, a divalent or higher group obtained by removing one or more atoms from the monovalent aryl Sub1 described above.

[0671] In this specification, as a heterocyclic group in the linking group, examples include divalent or higher groups obtained by removing one or more atoms from the monovalent heteroaryl Sub2 described above.

[0672] Example The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[0673] <Compound> The compounds used in the manufacture of the organic EL elements of Examples 1-16 and the compounds synthesized in Synthetic Examples 1-16 are shown below.

[0674] Compounds 1 to 16 are compound M3 represented by the general formula (100).

[0675] Compounds 3-4 and compounds 14-15 also belong to the group of compounds represented by the general formula (201).

[0676] Compound 9 also belongs to the group of compounds represented by the general formula (300).

[0677] Compound 10 also belongs to the group of compounds represented by the general formula (202).

[0678] Compound 11 also belongs to the group of compounds represented by the general formula (203).

[0679]

Chemistry 139

[0680] [Chemistry 140]

[0681]

Chemistry 141

[0682]

Chemistry 142

[0683]

Chemistry 143

[0684]

Chemistry 144

[0685]

Chemistry 145

[0686] The comparative compounds Ref-1 and Ref-2 used in the manufacture of the organic EL elements of Comparative Examples 1 to 6 are shown below.

[0687]

Chemistry 146

[0688] Other compounds used in the manufacture of the organic EL elements of Examples 1-16 and Comparative Examples 1-6 are described below.

[0689]

Chemistry 147

[0690]

Chemistry 148

[0691]

Chemistry 149

[0692] [Chemical 150]

[0693]

Chemistry 151

[0694]

Chemistry 152

[0695] <Fabrication of Organic EL Components 1> [Example 1] A glass substrate (manufactured by Geoma Technology Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130nm.

[0696] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compounds HT and HA were co-evaporated onto the side with the transparent electrode lines, forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[0697] Next, compound HT is deposited on the hole injection layer to form a hole transport layer with a thickness of 200 nm.

[0698] Next, the compound EBL is deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm.

[0699] Next, compound RD (as fluorescent compound M1), compound TADF-1 (as delayed fluorescence compound M2), and compound 1 (as compound M3) were co-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 25 nm. The concentration of compound RD in the light-emitting layer was set to 1% by mass, the concentration of compound TADF-1 was set to 25% by mass, and the concentration of compound 1 was set to 74% by mass.

[0700] Next, the compound HBL is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm.

[0701] Next, the compound ET is deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm.

[0702] Next, lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[0703] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[0704] If the component configuration of the organic EL element of Example 1 is shown in a simplified manner, it is as follows.

[0705] ITO (130) / HT:HA (10, 97%: 3%) / HT (200) / EBL (10) / Compound 1:TADF-1:RD (25, 74%: 25%: 1%) / HBL (10) / ET (30) / LiF (1) / Al (80) Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[0706] Within the same brackets, the percentage figures (97%: 3%) indicate the proportions (mass%) of compounds HT and HA in the hole injection layer, and the percentage figures (74%: 25%: 1%) indicate the proportions (mass%) of compounds M3, M2, and M1 in the luminescent layer. The same labeling applies below.

[0707] [Comparative Examples 1-2] Except that compound 1 in Example 1 was replaced with the compound listed in the column for compound M3 in Table 1, the organic EL elements of Comparative Examples 1-2 were prepared in the same manner as in Example 1.

[0708] <Evaluation 1> The organic EL elements fabricated in Example 1 and Comparative Examples 1-2 were evaluated as follows. The measurement results are shown in Table 1.

[0709] In addition, Ref-1 and Ref-2 used in the luminescent layer of Comparative Examples 1 to 2 are described in the column of compound M3 for convenience.

[0710] • Drive voltage The measurement involves applying an electric current between the anode and cathode to achieve a current density of 10 mA / cm². 2 Voltage at that time (unit: V).

[0711] External quantum efficiency (EQE) The applied voltage to the element was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation) to achieve a current density of 10 mA / cm². 2 The spectroscopic emission brightness spectrum at that time was obtained. Based on the obtained spectroscopic emission brightness spectrum, it was assumed that Lambertian emission occurred, and the external quantum efficiency EQE (in %) was calculated.

[0712] ·Lifespan LT95 The measurement was performed using a CS-200 spectroradiometer (manufactured by Konica Minolta Corporation) to apply a voltage to the element to achieve a current density of 50 mA / cm². 2 The time it takes for the brightness to reach 95% of the initial brightness (unit: hr).

[0713] • Main peak wavelength λp The current density of the organic EL element was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Corporation) when a voltage was applied to the element to achieve a current density of 10 mA / cm². 2 The spectrophotometer of the emission intensity at that time was obtained. The wavelength λp (unit: nm) of the main peak was calculated based on the obtained spectrophotometer.

[0714] Table 1

[0715] • Explanation of Table 1 λp represents the main peak wavelength [nm] of the organic EL element. The same applies to Tables 2 and 3.

[0716] As shown in Table 1, the organic EL element of Example 1 exhibits a longer LT95 value compared to the organic EL element of Comparative Example 1, which used compound Ref-1 instead of compound 1 (as compound M3), and the organic EL element of Comparative Example 2, which used compound Ref-2 instead of compound 1 (as compound M3). Therefore, the organic EL element of Example 1 emits light with a long lifetime.

[0717] Furthermore, compared with the organic EL elements of Comparative Examples 1 and 2, the organic EL element of Example 1 has a lower driving voltage and a higher external quantum efficiency (EQE).

[0718] <Fabrication of Organic EL Components 2> [Example 2] A glass substrate (manufactured by Geoma Technology Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130nm.

[0719] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compounds HT and HA were co-evaporated onto the side with the transparent electrode lines, forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[0720] Next, compound HT is deposited on the hole injection layer to form a hole transport layer with a thickness of 200 nm.

[0721] Next, the compound CBP is deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm.

[0722] Next, compound RD (as fluorescent compound M1), compound TADF-1 (as delayed fluorescence compound M2), and compound 1 (as compound M3) were co-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 25 nm. The concentration of compound RD in the light-emitting layer was set to 1% by mass, the concentration of compound TADF-1 was set to 25% by mass, and the concentration of compound 1 was set to 74% by mass.

[0723] Next, the compound HBL is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm.

[0724] Next, the compound ET is deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm.

[0725] Next, lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[0726] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[0727] If the component configuration of the organic EL element of Example 2 is shown in a simplified manner, it is as follows.

[0728] ITO (130) / HT:HA (10, 97%: 3%) / HT (200) / CBP (10) / Compound 1:TADF-1:RD (25, 74%: 25%: 1%) / HBL (10) / ET (30) / LiF (1) / Al (80) Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[0729] [Examples 3-4] Except that compound 1 in Example 2 was replaced with the compound listed in the column for compound M3 in Table 2, the organic EL elements of Examples 3 to 4 were prepared in the same manner as in Example 2.

[0730] [Comparative Examples 3-4] Except that compound 1 in Example 2 was replaced with the compound listed in the column for compound M3 in Table 2, the organic EL elements of Comparative Examples 3-4 were prepared in the same manner as in Example 2.

[0731] <Evaluation 2> The main peak wavelength λp and lifetime LT95 of the organic EL elements fabricated in Examples 2-4 and Comparative Examples 3-4 were measured using the same method as in Example 1. The results are shown in Table 2.

[0732] In addition, Ref-1 and Ref-2 used in the luminescent layer of Comparative Examples 3 to 4 are described in the column of compound M3 for convenience.

[0733] Table 2

[0734] As shown in Table 2, the organic EL elements of Examples 2-4 exhibit longer LT95 values ​​compared to the organic EL element of Comparative Example 3, which used compound Ref-1 instead of compounds 1-3 as compound M3, and the organic EL element of Comparative Example 4, which used compound Ref-2 instead of compounds 1-3 as compound M3. Therefore, the organic EL elements of Examples 2-4 exhibit long-lifetime luminescence.

[0735] <Fabrication of Organic EL Components 3> [Example 5] A glass substrate (manufactured by Geoma Technology Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130nm.

[0736] The washed glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compounds HT and HA were co-evaporated onto the side with the transparent electrode lines, forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[0737] Next, compound HT is deposited on the hole injection layer to form a hole transport layer with a thickness of 200 nm.

[0738] Next, the compound EBL is deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm.

[0739] Next, compound RD (as fluorescent compound M1), compound TADF-2 (as delayed fluorescence compound M2), and compound 1 (as compound M3) were co-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 25 nm. The concentration of compound RD in the light-emitting layer was set to 1% by mass, the concentration of compound TADF-2 was set to 25% by mass, and the concentration of compound 1 was set to 74% by mass.

[0740] Next, the compound HBL is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm.

[0741] Next, the compound ET is deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm.

[0742] Next, lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[0743] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[0744] If the component configuration of the organic EL element of Example 5 is shown in a simplified manner, it is as follows.

[0745] ITO (130) / HT:HA (10, 97%: 3%) / HT (200) / EBL (10) / Compound 1:TADF-2:RD (25, 74%: 25%: 1%) / HBL (10) / ET (30) / LiF (1) / Al (80) Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[0746] <Evaluation 3> The main peak wavelength λp, driving voltage, external quantum efficiency EQE, and lifetime LT95 of the organic EL element fabricated in Example 5 were measured using the same method as in Example 1. The results are shown in Table 3.

[0747] Table 3

[0748] As shown in Table 3, the organic EL element of Example 5 exhibits a relatively long LT95 value. Therefore, the organic EL element of Example 5 emits light with a long lifetime.

[0749] <Fabrication of Organic EL Components 4> [Example 6] The organic EL element of Example 6 was prepared in the same manner as in Example 1, except that compound M2 in Example 1 was replaced with the compound listed in the column for compound M2 in Table 4.

[0750] If the component configuration of the organic EL element of Example 6 is shown in a simplified manner, it is as follows.

[0751] ITO (130) / HT:HA (10, 97%: 3%) / HT (200) / EBL (10) / Compound 1:TADF-3:RD (25, 74%: 25%: 1%) / HBL (10) / ET (30) / LiF (1) / Al (80) Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[0752] [Examples 7-16] Except that compound 1 in Example 6 was replaced with the compound listed in the column for compound M3 in Table 4, the organic EL elements of Examples 7 to 16 were prepared in the same manner as in Example 6.

[0753] [Comparative Examples 5-6] Except that compound 1 in Example 6 was replaced with the compound listed in the column for compound M3 in Table 4, the organic EL elements of Comparative Examples 5-6 were prepared in the same manner as in Example 6.

[0754] <Rating 4> The main peak wavelength λp, driving voltage, external quantum efficiency EQE, and lifetime LT95 of the organic EL devices fabricated in Examples 6-16 and Comparative Examples 5-6 were measured using the same method as in Example 1. The results are shown in Table 4.

[0755] In addition, Ref-1 and Ref-2 used in the luminescent layer of Comparative Examples 5 and 6 are described in the column of compound M3 for convenience.

[0756] Table 4

[0757] As shown in Table 4, the organic EL devices of Examples 6-16 significantly improved LT95 compared to the organic EL devices of Comparative Examples 5-6. Furthermore, compared to the organic EL device of Comparative Example 6, the organic EL devices of Examples 6-16 significantly reduced the driving voltage and significantly improved the external quantum efficiency (EQE).

[0758] <Compound Evaluation> The physical properties of the compounds used in the luminescent layers of each example and the compounds synthesized in the synthesis examples described later were measured by the following methods.

[0759] Thermally activated delayed fluorescence (Delayed fluorescence of compound TADF-1) Delayed fluorescence by utilizing Figure 2The apparatus shown is used to measure the transition PL for confirmation. The compound TADF-1 is dissolved in toluene, and to eliminate the effect of self-absorption, a dilute solution with an absorbance below 0.05 at the excitation wavelength is prepared. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[0760] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al., J. Phys. Chem., 80 (1976) 969.

[0761] Upon excitation by pulsed light (light irradiated by a pulsed laser) at a wavelength absorbed by the compound TADF-1, there exists prompt emission (instantaneous emission) immediately observable from the excitation state and delayed emission (delayed emission) not immediately observable after excitation. In this embodiment, delayed fluorescence emission refers to the amount of delayed emission (delayed emission) being 5% or more relative to the amount of prompt emission (instantaneous emission). Specifically, the amount of prompt emission (instantaneous emission) is denoted as X. P The amount of delayed emission is denoted as X. D At that time, X D / X P The value is above 0.05.

[0762] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0763] For compound TADF-1, it was confirmed that the amount of delayed luminescence was greater than 5% relative to the amount of immediate luminescence. Specifically, for compound TADF-1, X was confirmed. D / X P The value is above 0.05.

[0764] (Delayed fluorescence of compounds TADF-2 and TADF-3) Except that compound TADF-2 was used instead of compound TADF-1, the delayed fluorescence of compound TADF-2 was confirmed in the same manner as described above. For compound TADF-2, X was confirmed. D / X P The value is above 0.05.

[0765] Except that compound TADF-3 was used instead of compound TADF-1, the delayed fluorescence of compound TADF-3 was confirmed in the same manner as described above. For compound TADF-3, X was confirmed. D / X P The value is above 0.05.

[0766] Singlet energy S1 The singlet energies S1 of compounds 1–16, TADF-1, TADF-2, TADF-3, RD, Ref-1, and Ref-2 were measured using the solution method described above. The measurement results are shown in Tables 5–7.

[0767] • Bandgap at 77K The band gap T at 77 K for compounds TADF-1, TADF-2, and TADF-3 was measured using the method described above. 77K △ST was calculated. The results are shown in Table 6.

[0768] • The main peak wavelength λ of the compound The main peak wavelengths λ of compounds TADF-1, TADF-2, TADF-3, and compound RD were measured using the following methods. The measurement results are shown in Tables 6 and 7.

[0769] A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The emission spectrum of the sample was measured at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). In this embodiment, the emission spectrum was measured using a Hitachi spectrophotometer (device name: F-7000). However, the emission spectrum measurement apparatus is not limited to the apparatus used herein. In the emission spectrum, the wavelength of the peak where the emission intensity reaches its maximum is taken as the main peak wavelength λ.

[0770] Table 5

[0771] Table 6

[0772] • Explanation of Table 6 "<0.01" means that △ST is less than 0.01eV.

[0773] Table 7

[0774] <Compound Synthesis> • Synthesis Example 1: Synthesis of Compound 1

Chemistry 153

[0775] Under a nitrogen atmosphere, xylene (50 mL) was added to a mixture of carbazole (1.84 g, 11.0 mmol), 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan (4.39 g, 11.0 mmol), palladium acetate (49.4 mg, 0.22 mmol), tri-tert-butylphosphine tetrafluoroborate (t-Bu3P-HBF4) (122.7 mg, 0.44 mmol), and sodium tert-butoxide (t-BuONa) (2.11 g, 22.0 mmol), and the mixture was stirred at 130 °C for 8 hours. After the reaction was complete, the solid was filtered off and recrystallized with toluene to give compound 1 (3.31 g, 62% yield). The compound was identified as compound 1 by LC-MS (Liquid Chromatography-Mass Spectrometry).

[0776] • Synthesis Example 2: Synthesis of Compound 2

Chemistry 154

[0777] Under a nitrogen atmosphere, 1,2-dimethoxyethane (70 mL) and water (35 mL) were added to a mixture of (3,5-bis(9H-carbazole-9-yl)phenyl)boronic acid (4.98 g, 11.0 mmol), 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan (4.39 g, 11.0 mmol), tetrakis(triphenylphosphine)palladium (635.6 mg, 0.55 mmol), and sodium carbonate (2.33 g, 22.0 mmol). The mixture was stirred at 85 °C for 8 hours. After the reaction was complete, the solid was filtered off and recrystallized with toluene to give compound 2 (5.01 g, 70% yield). The compound was identified as compound 2 by LC-MS analysis.

[0778] • Synthesis Example 3: Synthesis of Compound 3

Chemistry 155

[0779] Except that 2,7-diphenyl-9H-carbazole was used instead of carbazole in the synthesis of compound 1 in Synthesis Example 1, compound 3 was synthesized in the same manner as in Synthesis Example 1 to obtain compound 3. The yield was 59%. It was identified as compound 3 by LC-MS analysis.

[0780] • Synthesis Example 4: Synthesis of Compound 4

Chemistry 156

[0781] Except that 3,6-diphenyl-9H-carbazole was used instead of carbazole in the synthesis of compound 1 in Synthesis Example 1, compound 4 was synthesized in the same manner as in Synthesis Example 1 to obtain compound 4. The yield was 65%. It was identified as compound 4 by LC-MS analysis.

[0782] • Synthesis Example 5: Synthesis of Compound 5

Chemistry 157

[0783] Except that 4-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan was used instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan in the synthesis of compound 1 in Synthetic Example 1, compound 5 was synthesized in the same manner as in Synthetic Example 1, yielding compound 5. The yield was 52%. It was identified as compound 5 by LC-MS analysis.

[0784] • Synthesis Example 6: Synthesis of Compound 6

Chemistry 158

[0785] Except that 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene was used instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan in the synthesis of compound 1 in Synthetic Example 1, compound 6 was synthesized in the same manner as in Synthetic Example 1, yielding compound 6. The yield was 65%. It was identified as compound 6 by LC-MS analysis.

[0786] • Synthesis Example 7: Synthesis of Compound 7

Chemistry 159

[0787] Except that (4-(9H-carbazole-9-yl)phenyl)boronic acid was used instead of (3,5-bis(9H-carbazole-9-yl)phenyl)boronic acid in the synthesis of compound 2 in Synthesis Example 2, the same synthesis as in Synthesis Example 2 was performed to obtain compound 7. The yield was 43%. It was identified as compound 7 by LC-MS analysis.

[0788] • Synthesis Example 8: Synthesis of Compound 8 [Chemical 160]

[0789] Except that (4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (3,5-bis(9H-carbazole-9-yl)phenyl)boronic acid, and 9-(8-bromodibenzo[b,d]furan-2-yl)-9H-carbazole was used instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl))dibenzo[b,d]furan was used in the same manner as in Synthetic Example 2, compound 8 was obtained. The yield was 57%. It was identified as compound 8 by LC-MS analysis.

[0790] • Synthesis Example 9: Synthesis of Compound 9

Chemistry 161

[0791] Except that (4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (3,5-bis(9H-carbazole-9-yl)phenyl)boronic acid, and 1-bromodibenzo[b,d]furan was used instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl))dibenzo[b,d]furan was used in the same manner as in Synthetic Example 2, compound 9 was obtained. The yield was 26%. It was identified as compound 9 by LC-MS analysis.

[0792] • Synthesis Example 10: Synthesis of Compound 10

Chemistry 162

[0793] Except for the use of (4-(3,6-diphenyl-9H-carbazole-9H-9-yl)phenyl)boronic acid instead of (3,5-di(9H-carbazole-9-yl)phenyl)boronic acid and the use of 3-(4-bromophenyl)dibenzo[b,d]furan instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl))dibenzo[b,d]furan in the synthesis of compound 2 in Synthetic Example 2, the synthesis was carried out in the same manner as in Synthetic Example 2, yielding compound 10. The yield was 46%. It was identified as compound 10 by LC-MS analysis.

[0794] • Synthesis Example 11: Synthesis of Compound 11

Chemistry 163

[0795] Except for the use of (4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl)boronic acid instead of (3,5-di(9H-carbazole-9-yl)phenyl)boronic acid and the use of 4-(4-bromophenyl)dibenzo[b,d]furan instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl))dibenzo[b,d]furan in the synthesis of compound 2 in Synthetic Example 2, the synthesis was carried out in the same manner as in Synthetic Example 2 to obtain compound 11. The yield was 55%. It was identified as compound 11 by LC-MS analysis.

[0796] • Synthesis Example 12: Synthesis of Compound 12

Chemistry 164

[0797] Except that 12H-benzofuran[2,3-a]carbazole was used instead of carbazole in the synthesis of compound 1 in Synthesis Example 1, compound 12 was synthesized in the same manner as in Synthesis Example 1, yielding compound 12. The yield was 61%. It was identified as compound 12 by LC-MS analysis.

[0798] • Synthesis Example 13: Synthesis of Compound 13

Chemistry 165

[0799] Except that 7H-benzofuran[2,3-b]carbazole was used instead of carbazole in the synthesis of compound 1 in Synthesis Example 1, the same synthesis as in Synthesis Example 1 was performed to obtain compound 13. The yield was 59%. It was identified as compound 13 by LC-MS analysis.

[0800] • Synthesis Example 14: Synthesis of Compound 14

Chemistry 166

[0801] Compound 14 was obtained in the same manner as in Synthesis Example 1, except that 2-phenyl-9H-carbazole was used instead of carbazole in the synthesis of Compound 1 in Synthesis Example 1. The yield was 65%. Compound 14 was identified by LC-MS analysis.

[0802] ·Synthesis Example 15: Synthesis of Compound 15

Chemical Formula 167

[0803] Compound 15 was obtained in the same manner as in Synthesis Example 1, except that 3-phenyl-9H-carbazole was used instead of carbazole in the synthesis of Compound 1 in Synthesis Example 1. The yield was 61%. Compound 15 was identified by LC-MS analysis.

[0804] ·Synthesis Example 16: Synthesis of Compound 16

Chemical Formula 168

[0805] Compound 16 was obtained in the same manner as in Synthesis Example 2, except that (4-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of (3,5-di(9H-carbazol-9-yl)phenyl)boronic acid and 3-(4-bromophenyl)dibenz[b,d]furan was used instead of 2-(4'-bromo-[1,1'-biphenyl]-4-yl)dibenz[b,d]furan in the synthesis of Compound 2 in Synthesis Example 2. The yield was 50%. Compound 16 was identified by LC-MS analysis.

[0806] Explanation of Reference Numerals 1 Organic EL device 2 Substrate 3 Anode 4 Cathode 5 Light-emitting layer 6 Hole injection layer 7 Hole transport layer 8 Electron transport layer 9 Electron injection layer.

Claims

1. An organic electroluminescent element, characterized in that, have: anode; cathode; A light-emitting layer is contained between the anode and the cathode. The luminescent layer comprises a delayed-fluorescence compound M2 and a compound M3 represented by the following general formula (100). The singlet energy S1(M2) of compound M2 and the singlet energy S1(M3) of compound M3 satisfy the following mathematical relationship (Equation 1): S1(M3) > S1(M2) (number 1) 【Chemistry 1】 In the general formula (100), X1 is an oxygen atom or a sulfur atom, and C1 is a carbon atom. n is 1, 2, or 3. k is 1, 2, or 3. When m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (100), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (100), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (100), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R4 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The ring is formed by bonding one or more groups from a group of R4s together, or by bonding two or more groups from a plurality of R4s together, wherein the three R4s are the same or different from each other, and the three R4s are bonded to carbon atoms at any position of f, g, h and i as shown in the general formula (100), and C1 is bonded to carbon atoms at any position of f, g, h and i that are not bonded to the R4s. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R4 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

2. The organic electroluminescent element as described in claim 1, characterized in that, The light-emitting layer also contains a fluorescent compound M1. The singlet energy S1(M2) of compound M2 and the singlet energy S1(M1) of compound M1 satisfy the following mathematical expression (Equation 2): S1(M2) > S1(M1) (number 2).

3. The organic electroluminescent element as described in claim 1 or 2, characterized in that, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in the group are bonded together to form a loop, and R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups consisting of two or more R4s do not bond to each other.

4. The organic electroluminescent element as described in claim 1 or 2, characterized in that, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups consisting of two or more R4s do not bond to each other.

5. The organic electroluminescent element according to any one of claims 1 to 4, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. L1 is a single bond, or Derived from unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or A group derived from an unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

6. The organic electroluminescent element according to any one of claims 1 to 5, characterized in that, n is 1 or 2, k is 1 or 2.

7. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, n is 1, k is 1 or 2.

8. The organic electroluminescent element according to any one of claims 1 to 6, characterized in that, n is 2, k is 1 or 2.

9. The organic electroluminescent element according to any one of claims 1 to 8, characterized in that, R 11 ~R 18 R4 and R 45 ~R 48 Each independently, hydrogen atom, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or Alkyl groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

10. The organic electroluminescent element according to any one of claims 1 to 9, characterized in that, R 11 ~R 18 R4 and R 45 ~R 48 Each independently, hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or Heterocyclic groups with 5 to 30 cyclic atoms, either substituted or unsubstituted.

11. The organic electroluminescent element according to any one of claims 1 to 10, characterized in that, R 11 ~R 18 R4 and R 45 ~R 48 Each independently, hydrogen atom, or Aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

12. The organic electroluminescent element according to any one of claims 1 to 11, characterized in that, R 11 ~R 18 R4 and R 45 ~R 48 Each independently, hydrogen atom, or Substituted or unsubstituted phenyl groups.

13. The organic electroluminescent element according to any one of claims 1 to 12, characterized in that, R 11 ~R 18 Each independently, hydrogen atom, or Substituted or unsubstituted phenyl groups R4 and R 45 ~R 48 Each is an independent hydrogen atom.

14. The organic electroluminescent element according to any one of claims 1 to 13, characterized in that, L1 is a single bond, or A group derived from an unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

15. The organic electroluminescent element according to any one of claims 1 to 14, characterized in that, L1 is a single bond, or A group derived from an unsubstituted benzene ring.

16. The organic electroluminescent element according to any one of claims 1 to 15, characterized in that, L1 is a single bond.

17. The organic electroluminescent element as described in claim 1 or 2, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by the following general formula (100A) or the following general formula (100B). 【Chemistry 2】 【Transformation 3】 In the general formulas (100A) and (100B), X1 and R 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 respectively with X1 and R in the general formula (100) 11 ~R 18 n, k, m, L1, R2, R 31 R 32 R 34 R 35 and R 45 ~R 48 Synonyms, R 41 ~R 44 Each is independently synonymous with R4 in the general formula (100).

18. The organic electroluminescent element as claimed in claim 17, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by the general formula (100A).

19. The organic electroluminescent element as described in claim 1 or 2, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by the general formula (100E). 【Chemistry 4】 In the general formula (100E), X1 and C1 are synonyms with X1 and C1 in the general formula (100), respectively. n is 1 or 2, k is 1 or 2, R 11 ~R 18 R4 and R 45 ~R 48 Each independently, hydrogen atom, or Aryl groups, substituted or unsubstituted, with a cyclic carbon number of 6–30. When at least one of n and k is 2, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 Groups consisting of two or more R4s do not bond to each other. L1 is a single bond, or A group derived from an unsubstituted aryl group having 6 to 30 unsubstituted cyclic carbon atoms, wherein n is 1 when L1 is a single bond, and multiple L1 groups may be the same or different when k is 2. When k is 1, one L1 atom bonds to a carbon atom at position a, b, c, d, or e. When k is 2, the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e, respectively.

20. The organic electroluminescent element as described in claim 1 or 2, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by the general formula (100F). 【Transformation 5】 In the general formula (100F), X1 and C1 are synonyms with X1 and C1 in the general formula (100), respectively. n is 1 or 2, When n is 1, the nitrogen atom at position 9 of one carbazole ring in the general formula (100F) bonds to a carbon atom at position a, b, c, d, or e in the general formula (100F). When n is 2, the nitrogen atom at position 9 of the two carbazole rings in the general formula (100F) bonds to a carbon atom at any position a, b, c, d, or e, respectively. R 11 ~R 18 Each independently, hydrogen atom, or Substituted or unsubstituted phenyl groups When n is 2, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups do not bond with each other.

21. The organic electroluminescent element as described in claim 1 or 2, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by any one of the following general formulas (401) to (406). 【Transformation 6】 【Transformation 7】 In the general formulas (401) to (406), X1, R4, R 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 R2, L1, R 11 ~R 18 m, n, and k are respectively related to X1, R4, R in the general formula (100). 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 R2, L1, R 11 ~R 18 m, n, and k are synonyms; Y1 represents an oxygen atom or a sulfur atom; R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

22. The organic electroluminescent element as described in claim 21, characterized in that, n is 1 or 2, k is 1 or 2.

23. The organic electroluminescent element as described in claim 21, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by any one of the following general formulas (401A) to (406A). 【Transformation 8】 【Chemistry 9】 In the general formulas (401A) to (406A), X1, R4, R 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 L1, R 11 ~R 18 And n is respectively related to X1, R4, R in the general formula (100) 45 ~R 48 C1, R 31 ~R 32 R 34 ~R 35 L1, R 11 ~R 18 And n is synonymous with R 21 ~R 22 and R 24 ~R 25 Each is independently synonymous with R2 in the general formula (100), Y1 is an oxygen atom or a sulfur atom, and R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

24. The organic electroluminescent element as described in claim 23, characterized in that, Compound M3, represented by the general formula (100), is a compound represented by any one of the following general formulas (401B) to (406B). 【Chemistry 10】 【Chemistry 11】 In the general formulas (401B) to (406B), X1, R 45 ~R 48 R 31 ~R 32 R 34 ~R 35 L1 and R 11 ~R 18 respectively with X1 and R in the general formula (100) 45 ~R 48 R 31 ~R 32 R 34 ~R 35 L1 and R 11 ~R 18 Synonyms, R 41 R 42 and R 44 Each is independently synonymous with R4 in the general formula (100), R 21 ~R 22 and R 24 ~R 25 Each is independently synonymous with R2 in the general formula (100), Y1 is an oxygen atom or a sulfur atom, and R 401 ~R 404 Independently related to R in the general formula (100) 11 ~R 18 Synonyms, of which R 401 and R 402 group, R 402 and R 403 The group, and R 403 and R 404 Any one or more groups in the group may bond together to form a ring or not.

25. The organic electroluminescent element according to any one of claims 21 to 24, characterized in that, R 45 and R 46 group, R 46 and R 47 group, R 47 and R 48 group, R 41 and R 42 Groups consisting of two or more R4s do not bond to each other.

26. The organic electroluminescent element according to any one of claims 21 to 25, characterized in that, R2, R 21 ~R 22 R 24 ~R 25 R 31 ~R 32 and R 34 ~R 35 It is a hydrogen atom. L1 is a single bond, or Derived from unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or A group derived from an unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

27. The organic electroluminescent element according to any one of claims 1 to 26, characterized in that, X1 is an oxygen atom.

28. An electronic device, characterized in that, It is equipped with an organic electroluminescent element as described in any one of claims 1 to 27.

29. A compound, characterized in that, Expressed by the following general formula (201), the following general formula (202), or the following general formula (203), 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 In the general formulas (201) to (203), X1 is an oxygen atom or a sulfur atom. n is 1, 2, or 3. k is 1, 2, or 3. When m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups are not mutually bonded, and multiple R groups are such that at least one of n and k is 2 or more. 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (201), (202), or (203), respectively, and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R 41 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 and R 41 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or Substituted or unsubstituted arylthio groups with 6 to 30 carbon atoms in the cyclic formation. Among them, R 11 ~R 18 At least one of them is an unsubstituted aryl group with a cyclic carbon number of 6 to 30.

30. A compound, characterized in that, Represented by the following general formula (300), 【Chemistry 15】 In the general formula (300), X1 is an oxygen atom or a sulfur atom. n is 1, 2, or 3. k is 1, 2, or 3. When m is 2, 3, or 4, k + m = 5. R 11 ~R 18 Each is independently a hydrogen atom or a substituent, or R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in a set are bonded together to form a ring, where at least one of n and k is 2 or more, multiple R 11 Multiple Rs that are the same or different from each other 12 Multiple Rs that are the same or different from each other 13 Multiple Rs that are the same or different from each other 14 Multiple Rs that are the same or different from each other 15 Multiple Rs that are the same or different from each other 16 Multiple Rs that are the same or different from each other 17 Multiple Rs that are the same or different from each other 18 Whether they are the same or different, L1 is a single bond or a linking group, where n is 1 when L1 is a single bond. When k is 2 or higher, multiple L1 values ​​can be identical or different from each other. L1, as a linking group, is... Derived from aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted. Groups derived from heterocyclic groups with 5 to 30 cyclic atoms, whether substituted or unsubstituted, or A group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms. When k is 1 and m is 4, the four R2 atoms are bonded to carbon atoms at any position a, b, c, d, and e as shown in the general formula (300), and one L1 atom is bonded to carbon atoms at positions a, b, c, d, or e that are not bonded to the R2 atoms. When k is 2 and m is 3, the three R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e as shown in the general formula (300), and the two L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. When k is 3 and m is 2, the two R2 atoms are bonded to carbon atoms at any position of a, b, c, d, and e in the general formula (300), and the three L1 atoms are bonded to carbon atoms at any position of a, b, c, d, and e that are not bonded to the R2 atoms. R2, R 31 R 32 R 34 and R 35 Each R2 can be an independent hydrogen atom or substituent, and when m is 2 or more, the multiple R2s can be the same or different from each other. R 41 R 42 R 43 and R 45 ~R 48 Each is independently a hydrogen atom or a substituent, or R 41 and R 42 group, R 42 and R 43 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 A ring is formed by bonding any one or more groups within a group together. R as a substituent 11 ~R 18 R2, R 31 R 32 R 34 R 35 R 41 ~R 43 and R 45 ~R 48 Each independently, Halogen atoms, cyano, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms Alkenes with 2 to 30 carbon atoms, whether substituted or unsubstituted. Alkyne groups with 2 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Substituted or unsubstituted aryl phosphoryl groups with 6 to 60 carbon atoms hydroxyl, Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group, amino, Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation, Thiol group, Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

31. The compound according to claim 29 or 30, characterized in that, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 Any one or more groups in the group are bonded together to form a loop, and R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other.

32. The compound according to claim 29 or 30, characterized in that, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other.

33. The compound according to any one of claims 29 to 32, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. L1 is a single bond, or Derived from unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or A group derived from an unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

34. The compound according to any one of claims 29 to 33, characterized in that, n is 1 or 2, k is 1 or 2.

35. The compound according to any one of claims 29 to 34, characterized in that, R 11 ~R 18 and R 41 ~R 48 Each independently, hydrogen atom, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or Alkyl groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

36. The compound according to any one of claims 29 to 35, characterized in that, L1 is a single bond, or A group derived from an unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

37. The compound of claim 29, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. n is 1 or 2, k is 1 or 2, R 11 ~R 18 and R 41 ~R 48 Each independently, hydrogen atom, or Aryl groups, substituted or unsubstituted, with a cyclic carbon number of 6–30. Among them, R 41 and R 42 group, R 42 and R 43 group, R 43 and R 44 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other. L1 is a single bond, or A group derived from an unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

38. The compound according to claim 29, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. n is 1 or 2, k is 1 or 2, R 11 ~R 18 Each independently, hydrogen atom, or Substituted or unsubstituted phenyl groups R 41 ~R 48 It is a hydrogen atom. L1 is a single bond.

39. The compound according to claim 30, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. n is 1 or 2, k is 1 or 2, R 11 ~R 18 R 41 ~R 43 and R 45 ~R 48 Each independently, hydrogen atom, or Aryl groups, substituted or unsubstituted, with a cyclic carbon number of 6–30. Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 group, R 17 and R 18 group, R 41 and R 42 group, R 42 and R 43 group, R 45 and R 46 group, R 46 and R 47 The group, and R 47 and R 48 The groups do not bond with each other. L1 is a single bond, or A group derived from an unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

40. The compound according to claim 30, characterized in that, R2, R 31 R 32 R 34 and R 35 It is a hydrogen atom. n is 1 or 2, k is 1 or 2, R 11 ~R 18 Each independently, hydrogen atom, or Substituted or unsubstituted phenyl groups Among them, R 11 and R 12 group, R 12 and R 13 group, R 13 and R 14 group, R 15 and R 16 group, R 16 and R 17 The group, and R 17 and R 18 The groups do not bond with each other. R 41 ~R 43 and R 45 ~R 48 It is a hydrogen atom. L1 is a single bond.

41. A compound, characterized in that, Represented by any one of the following general formulas (501) to (514), 【Chemistry 16】 【Chemistry 17】 。 42. A material for organic electroluminescent devices, characterized in that, The compound comprising any one of claims 29 to 41.

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