Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

Provided is a compound represented by general formula (1), where D is a group represented by general formula (11), general formula (12), or general formula (13), where at least one D is a group represented by general formula (12) or general formula (13), where at least one R is a substituent, and the sum of the number of substituents R and the number of groups represented by general formula (12) or general formula (13) is 3 or 4.

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 / JP2020 / 037282, entitled "Compound, Material for Organic Electroluminescent Device, Organic Electroluminescent Device and Electronic Device", which has entered the national phase in China. The application number of the Chinese invention application is 202080068066.8, and the application date is September 30, 2020. Technical Field

[0002] This invention relates to compounds, materials for organic electroluminescent elements, 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 their internal quantum efficiency of 25% is considered the limit. Therefore, research is underway to improve the performance of organic EL devices.

[0005] For example, 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") has been proposed and investigated.

[0006] The TADF (Thermally Activated Delayed Fluorescence) mechanism is a mechanism that utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under thermal influence when using materials with a small energy difference (ΔST) between singlet and triplet energy levels. For example, information on TADF is described in "Chiba Adachi, 'Device Properties of Organic Semiconductors,' Kodansha, April 1, 2012, pp. 261-268."

[0007] Compounds exhibiting thermally activated delayed fluorescence (TADF properties) (hereinafter also referred to as TADF-type compounds) are known to include compounds in which the donor and acceptor sites are bonded within the molecule.

[0008] Examples of literature relating to organic EL elements and compounds used in organic EL elements include Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, and Patent Document 5.

[0009] Existing technical documents Patent documents Patent Document 1: International Publication No. 2019 / 107932 Patent Document 2: International Publication No. 2019 / 107933 Patent Document 3: International Publication No. 2019 / 107934 Patent Document 4: International Publication No. 2014 / 208698 Patent Document 5: International Publication No. 2018 / 237389 Summary of the Invention The technical problem that the invention aims to solve To improve the performance of electronic devices such as displays, it is desirable to further enhance the performance of organic EL components.

[0010] One example of the performance characteristics of organic EL devices is luminous efficiency. As a factor in improving luminous efficiency, using compounds with high photoluminescence quantum yield (PLQY) can be cited. Furthermore, another performance characteristic of organic EL devices is a lower driving voltage.

[0011] The object of this invention is to provide a compound with a high PLQY. Furthermore, the object of this invention is to provide a material for an organic electroluminescent device (OLED) comprising a compound with a high PLQY, as well as the organic OLED, and an electronic device equipped with the organic OLED. Additionally, the object of this invention is to provide a high-performance organic EL device and an electronic device equipped with the organic OLED.

[0012] Solution to the above technical problems According to one aspect of the present invention, a compound represented by the following general formula (1) is provided.

[0013] [Chemistry 1]

[0014] (In the general formula (1),) D is a group represented by the following general formula (11), general formula (12) or general formula (13), Wherein, at least one D is a group represented by the following general formula (12) or general formula (13), m is 1, 2, or 3. When m is 2 or 3, multiple Ds may be the same or different from each other. R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heteroaryl groups with 5–14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms substituted or unsubstituted arylsilyl groups having 3 to 6 carbon atoms 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 alkylamino groups with 2 to 12 carbon atoms 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. In this case, at least one R is a substituent. At least one R, acting as a substituent, is bonded to the benzene ring in the general formula (1) via a carbon-carbon bond. n is 1, 2, or 3. When n is 2 or 3, multiple R's can be the same or different from each other. The sum of the number of R substituents and the number of groups represented by the following general formula (12) or general formula (13) is 3 or 4. [Chemistry 2]

[0015] [Chemistry 3]

[0016] [Chemistry 4]

[0017] (In the general formula (11), R1 to R8 are each independently a hydrogen atom, a halogen atom, or a substituent.) R in the general formula (12) 11 ~R 18 Each can be independently a hydrogen atom, a halogen 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 A ring is formed by bonding together any one or more groups within a group. R in the general formula (13) 111 ~R 118 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 111 and R 112 group, R 112 and R 113 group, R 113 and R 114 group, R 115 and R 116 group, R 116 and R 117 The group, and R 117 and R 118 A ring is formed by bonding together any one or more groups within a group. R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, 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 cycloalkyl groups with 3 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, 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, 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, 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. In the general formulas (12) and (13), A, B, and C are each independently selected from the group of ring structures represented by the following general formulas (14), (15), and (16). The ring structure A, ring structure B, and ring structure C can be condensed with the adjacent ring structure at any position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, multiple ring structures A may be the same or different from each other. When px is 2, 3, or 4, multiple ring structures B may be the same or different from each other. When py is 2, 3, or 4, multiple ring structures C may be the same or different from each other. Wherein, at least one D is p, which is 2, 3, or 4 and contains a group represented by said general formula (12) as ring structure A, selected from the group consisting of ring structures represented by general formulas (15) and (16) below; or at least one of px and py is 2, 3, or 4 and contains a group represented by said general formula (13) as ring structure B or ring structure C, selected from the group consisting of ring structures represented by general formulas (15) and (16) below. In general formulas (11) to (13), * indicates the position where it bonds to the benzene ring in general formula (1). [Chemistry 5]

[0018] (In the general formula (14), R 19 and R 20 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups bond together to form a ring. In the general formulas (15) and (16), X1 and X2 are NR independently. 120 sulfur atoms or oxygen atoms R 120 It can be a hydrogen atom, a halogen atom, or a substituent. R as a substituent 19 R 20 and R 120 Each of these is independently synonymous with R1 through R8, which are substituents. According to one aspect of the present invention, a material for an organic electroluminescent element containing the compound described above is provided.

[0019] According to one aspect of the present invention, an organic electroluminescent element is provided, having an anode, a cathode, and an organic layer, wherein the organic layer comprises a compound of the present invention as a first compound.

[0020] 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.

[0021] According to one aspect of the present invention, a compound with a high PLQY can be provided. Furthermore, according to one aspect of the present invention, a material for an organic electroluminescent element or an organic electroluminescent element comprising a compound with a high PLQY can be provided. Furthermore, according to one aspect of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. Furthermore, according to one aspect of the present invention, a high-performance organic EL element and an electronic device equipped with the organic electroluminescent element can also be provided. Attached Figure Description

[0022] Figure 1 This is a schematic diagram of a device for measuring transient pulse (PL).

[0023] Figure 2 This is a graph showing an example of the decay curve of the transition PL.

[0024] Figure 3 This is a diagram illustrating a schematic configuration of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0025] Figure 4 This is a diagram showing the relationship between the energy levels and energy transfer of the first and second compounds in the light-emitting layer of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0026] Figure 5 This is a diagram showing the relationship between the energy levels and energy transfer of the first, second, and third compounds in the light-emitting layer of an example of an organic electroluminescent element according to a fourth embodiment of the present invention.

[0027] Figure 6 This is a diagram showing the relationship between the energy levels and energy transfer of the first and third compounds in the light-emitting layer of an example of an organic electroluminescent element according to a fifth embodiment of the present invention. Detailed Implementation

[0028] [First Implementation] (Compound) The compounds in this embodiment are compounds represented by the following general formula (1).

[0029] [Chemistry 6]

[0030] (In the general formula (1),) D is a group represented by the following general formula (11), general formula (12) or general formula (13), Wherein, at least one D is a group represented by the following general formula (12) or general formula (13), m is 1, 2 or 3 When m is 2 or 3, multiple Ds may be the same or different from each other. R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heteroaryl groups with 5–14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms substituted or unsubstituted arylsilyl groups having 3 to 6 carbon atoms 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 alkylamino groups with 2 to 12 carbon atoms 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. In this case, at least one R is a substituent. At least one R, acting as a substituent, is bonded to the benzene ring in the general formula (1) via a carbon-carbon bond. n is 1, 2, or 3. When n is 2 or 3, multiple R's can be the same or different from each other. The sum of the number of R substituents and the number of groups represented by the following general formula (12) or general formula (13) is 3 or 4. [Chemistry 7]

[0031] [Chemistry 8]

[0032] [Chemistry 9]

[0033] (In the general formula (11), R1 to R8 are each independently a hydrogen atom, a halogen atom, or a substituent.) R in the general formula (12) 11 ~R 18 Each can be independently a hydrogen atom, a halogen 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 A ring is formed by bonding together any one or more groups within a group. R in the general formula (13) 111 ~R 118 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 111 and R 112 group, R 112 and R 113 group, R 113 and R 114 group, R 115 and R 116 group, R 116 and R 117 The group, and R 117 and R 118 A ring is formed by bonding together any one or more groups within a group. R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, 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 cycloalkyl groups with 3 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, 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, 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, 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. In the general formulas (12) and (13), A, B, and C are each independently selected from the group of ring structures represented by the following general formulas (14), (15), and (16). The ring structure A, ring structure B, and ring structure C can be condensed with the adjacent ring structure at any position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, multiple ring structures A may be the same or different from each other. When px is 2, 3, or 4, multiple ring structures B may be the same or different from each other. When py is 2, 3, or 4, multiple ring structures C may be the same or different from each other. Wherein, at least one D is p, which is 2, 3, or 4 and contains a group represented by said general formula (12) as ring structure A, selected from the group consisting of ring structures represented by general formulas (15) and (16) below; or at least one of px and py is 2, 3, or 4 and contains a group represented by said general formula (13) as ring structure B or ring structure C, selected from the group consisting of ring structures represented by general formulas (15) and (16) below. In general formulas (11) to (13), * indicates the position where it bonds to the benzene ring in general formula (1). [Chemistry 10]

[0034] (In the general formula (14), R 19 and R 20 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups bond together to form a ring. In the general formulas (15) and (16), X1 and X2 are NR independently. 120 sulfur atoms or oxygen atoms R 120 It can be a hydrogen atom, a halogen atom, or a substituent. R as a substituent 19 R 20 and R 120Each of these is independently synonymous with R1 through R8, which are substituents. The compound of this embodiment has at least one D group in its molecule. A or group D B As D in the general formula (1).

[0035] Group D A It is a group represented by the general formula (12), wherein p is 2, 3 or 4, and includes any ring structure selected from the group consisting of ring structures represented by the general formulas (15) and (16) as ring structure A. Group D A Preferably, p is 2, 3 or 4, and includes a ring structure represented by the general formula (14) and a ring structure represented by the general formula (15) as ring structure A.

[0036] Group D B It is a group represented by the general formula (13), wherein at least one of px and py is 2, 3 or 4, and includes any ring structure selected from the group consisting of ring structures represented by the general formulas (15) and (16) as ring structure B or ring structure C. Group D B Preferably, at least one of px and py is 2, 3 or 4, and includes a ring structure represented by the general formula (14) and a ring structure represented by the general formula (15) as ring structure B or ring structure C.

[0037] Furthermore, in the compound of this embodiment, the number N of R as substituents is... R With group D A or group D B The number N D The sum (N R +N D () is 3 or 4.

[0038] The fact that R, as a substituent, is bonded to the benzene ring in the general formula (1) via carbon-carbon bonds means that the carbon atom in the element R, as a substituent, is directly bonded to any one of the six carbon atoms constituting the benzene ring in the general formula (1).

[0039] In the compound of this embodiment, the sum of the number of R as a substituent and the number of groups represented by the general formula (12) or general formula (13) is preferably 4.

[0040] In the compounds of this embodiment, the number N of R as substituents is... R With group D A or group D B The number N D The sum (N R +N D The preferred value is 4.

[0041] The compound represented by the general formula (1) is also preferably a compound represented by the general formula (110), general formula (120) or general formula (130).

[0042] [Chemistry 11]

[0043] (In the general formulas (110), (120) and (130), D, m, R and n are synonyms with D, m, R and n in the general formula (1), respectively.) The compound represented by the general formula (1) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (111) to (118).

[0044] [Chemistry 12]

[0045] (In the general formulas (111) and (112), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 Synonymous with R as a substituent in the general formula (1). [Chemistry 13]

[0046] (In the general formulas (113) to (116), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122 At least one of them is a substituent, and R is a substituent. 121 and R 122 Synonymous with R as a substituent in the general formula (1). [Chemistry 14]

[0047] (In the general formulas (117) and (118), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 Synonymous with R as a substituent in the general formula (1). The compound represented by the general formula (1) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (121) to (129).

[0048] [Chemistry 15]

[0049] (In the general formulas (121) to (123), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 Synonymous with R as a substituent in the general formula (1). [Chemistry 16]

[0050] (In the general formulas (124) to (126), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122 At least one of them is a substituent, and R is a substituent. 121 and R 122Synonymous with R as a substituent in the general formula (1). [Chemistry 17]

[0051] (In the general formulas (127) to (129), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 Synonymous with R as a substituent in the general formula (1). The compound represented by the general formula (1) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (131) to (135).

[0052] [Chemistry 18]

[0053] (In the general formula (131), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 Synonymous with R as a substituent in the general formula (1). [Chemistry 19]

[0054] (In the general formulas (132) to (134), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122At least one of them is a substituent, and R is a substituent. 121 and R 122 Synonymous with R as a substituent in the general formula (1). [Chemistry 20]

[0055] (In the general formula (135), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 Synonymous with R as a substituent in the general formula (1). Preferably, R in the general formula (12) 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. R in the general formula (13) 111 and R 112 group, R 112 and R 113 group, R 113 and R 114 group, R 115 and R 116 group, R 116 and R 117 The group, and R 117 and R 118 The groups are not mutually bonded.

[0056] In the general formula (14), R is preferred. 19 and R 20 The groups do not bond with each other.

[0057] The compound of this embodiment preferably has at least one group represented by the general formula (12).

[0058] In the general formula (12), p is preferably 2, 3 or 4.

[0059] In the general formula (13), preferably px and py are 2, 3 or 4 independently, respectively.

[0060] The compound of this embodiment preferably has at least one group D represented by the general formula (12). A As D in the general formula (1), wherein the group D represented by the general formula (12) A In this context, p is 2, 3, or 4, and includes any ring structure selected from the group consisting of ring structures represented by the general formula (15) and the general formula (16) as ring structure A.

[0061] In the compounds of this embodiment, it is preferred that ring structure A, ring structure B and ring structure C are each independently selected from the group consisting of ring structures represented by the general formula (14) and general formula (15).

[0062] In the compounds of this embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of groups represented by the following general formulas (12A), (12B), (12C), (12D), (12E) and (12F).

[0063] [Chemistry 21]

[0064] [Chemistry 22]

[0065] [Chemistry 23]

[0066] [Chemistry 24]

[0067] [Chemistry 25]

[0068] [Chemistry 26]

[0069] (In the general formulas (12A), (12B), (12C), (12D), (12E) and (12F), R 11 ~R 18 Independently related to R in the general formula (12) 11 ~R 18 Synonyms R 19 and R 20 Independently related to R in the general formula (14)19 and R 20 Synonyms X1 is synonymous with X1 in the general formula (15). The asterisk (*) in general formulas (12A), (12B), (12C), (12D), (12E), and (12F) indicates the position where the benzene ring in general formula (1) is bonded. R is preferably found in the general formulas (12A), (12B), (12C), (12D), (12E), and (12F). 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 The group, and R 19 and R 20 The groups are not mutually bonded.

[0070] In the compounds of this embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of the groups represented by the general formulas (12A), (12D) and (12F).

[0071] In the compound of this embodiment, X1 is preferably an oxygen atom or a sulfur atom.

[0072] In the compound of this embodiment, group D A Preferably, it is any group selected from the group consisting of groups represented by the general formula (12A), (12B), (12C), (12D), (12E) and (12F).

[0073] The compound of this embodiment preferably has at least one group selected from the group consisting of groups represented by the general formulas (12A), (12B), (12C), (12D), (12E), and (12F) as D in the general formula (1).

[0074] The compound of this embodiment is more preferably a group having at least one group selected from the group consisting of groups represented by the general formula (12A), (12B), (12C), (12D), (12E) and (12F) and X1 being an oxygen atom or a sulfur atom as D in the general formula (1).

[0075] Preferably, D in the general formulas (110), (120) and (130) is independently selected from the group consisting of groups represented by the general formulas (12A), (12B), (12C), (12D), (12E) and (12F).

[0076] D in the preferred general formulas (111) to (118), (121) to (129), and (131) to (135) 11 D 12 and D 13 Each is independently selected from the group consisting of groups represented by the general formulas (12A), (12B), (12C), (12D), (12E), and (12F).

[0077] In the compounds of this embodiment, R1 to R8 are preferably used as substituents, and R is preferably used as a substituent. 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having a cyclic carbon number of 3 to 30.

[0078] In the compounds of this embodiment, R1 to R8 are preferably used as substituents, and R is preferably used as a substituent. 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having 3 to 6 carbon atoms.

[0079] In the compounds of this embodiment, R1 to R8 are preferably used as substituents, and R is preferably used as a substituent. 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Unsubstituted alkyl groups having 1 to 30 carbon atoms Unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Unsubstituted alkoxy groups with 1 to 30 carbon atoms Unsubstituted aryloxy groups with 6–30 carbon atoms in the cyclic ring, Unsubstituted alkylamino groups with 2 to 30 carbon atoms Unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic ring, Unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Unsubstituted arylthio groups with 6 to 30 cyclic carbons.

[0080] In the compounds of this embodiment, R1 to R8 are preferably used as substituents, and R is preferably used as a substituent. 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted alkyl groups having 1 to 30 carbon atoms, or Unsubstituted cycloalkyl groups with 3 to 30 carbon atoms.

[0081] In the compounds of this embodiment, R1 to R8 and R are also preferred. 11 ~R 18 and R 111 ~R 118 It is a hydrogen atom.

[0082] In the compounds of this embodiment, preferably, R is independently a hydrogen atom, a halogen atom, or a substituent. R, as a substituent, is independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heteroaryl groups with 5–14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having 3 to 6 carbon atoms.

[0083] In the compounds of this embodiment, preferably, R is independently a hydrogen atom, a halogen atom, or a substituent. R, as a substituent, is independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heteroaryl groups with 5–14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Unsubstituted alkylsilyl groups with 3 to 6 carbon atoms Unsubstituted arylsilyl groups with 3 to 6 carbon atoms, Unsubstituted alkoxy groups with 1 to 6 carbon atoms, Unsubstituted aryloxy groups with 6–14 cyclic carbon atoms, Unsubstituted alkylamino groups with 2 to 12 carbon atoms, Unsubstituted alkylthio groups with 1 to 6 carbon atoms, or Unsubstituted arylthio groups with 6 to 14 cyclic carbons.

[0084] In the compounds of this embodiment, preferably, R is independently a hydrogen atom, a halogen atom, or a substituent. R, as a substituent, is independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heteroaryl groups with 5–14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms, or Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms.

[0085] The compound used in this embodiment is preferably a compound with delayed fluorescence.

[0086] 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. The compounds of this embodiment are preferably those demonstrating thermally activated delayed fluorescence generated by such a mechanism.

[0087] Typically, delayed fluorescence can be confirmed by transition PL (Photo Luminescence) measurements.

[0088] 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 exciting a sample by irradiating it with a pulsed laser and measuring the decay behavior (transition characteristics) of PL emission after irradiation stops. PL emission in TADF materials consists of two components: the emission component from singlet excitons generated by the initial PL excitation and the emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after pulsed laser irradiation.

[0089] On the other hand, delayed fluorescence originates from the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays slowly. 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.

[0090] Figure 1 The diagram shows a schematic of an example apparatus for measuring transient PL. Figure 1 The method for measuring transition PL and an example of analyzing the behavior of delayed fluorescence are explained.

[0091] Figure 1 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 1 The device described.

[0092] 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.

[0093] 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 predetermined 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.

[0094] 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.

[0095] [Chemistry 27]

[0096] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the reference compound H2 as the matrix material and the reference compound D1 as the dopant material.

[0097] Figure 2 The figure shows the attenuation curves obtained from the transition PL measured on thin film sample A and thin film sample B.

[0098] [Chemistry 28]

[0099] 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.

[0100] Specifically, luminescence from materials with delayed fluorescence can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence that is immediately observed 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 being excited by the pulse of light but is observed later.

[0101] 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 1 The device described in the text.

[0102] Furthermore, the delayed fluorescence of the compound in this embodiment is measured using a sample prepared by the method described below. For example, the compound of this embodiment is dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared to eliminate the effect of self-absorption. In addition, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, and then sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[0103] 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.

[0104] 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 1 The device described in the text.

[0105] In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the target compound is denoted as X. P The amount of delayed emission is denoted as X. D At that time, X D / X P The value is preferably 0.05 or higher.

[0106] The measurement of the amount of Prompt emission and the ratio of Delay emission for compounds other than those in this embodiment, as well as the measurement of the amount of Prompt emission and the ratio of Delay emission for compounds in this embodiment, are the same as those for compounds in this embodiment.

[0107] ·△ST In this embodiment, the minimum excited singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as △ST.

[0108] The lowest excited singlet energy S1 (M1) of the compound in this embodiment and the band gap T at 77 [K] of the compound in this embodiment 77KThe difference ΔST(M1) is preferably less than 0.3 eV, more preferably less than 0.2 eV, and even more preferably less than 0.1 eV. That is, ΔST(M1) preferably satisfies the following mathematical expression (number 10), (number 11), (number 12) or (number 13).

[0109] △ST(M1) = S1(M1) - T 77K (M1)<0.3eV…(Number 10) △ST(M1) = S1(M1) - T 77K (M1)<0.2eV…(Number 11) △ST(M1) = S1(M1) - T 77K (M1)<0.1eV…(Number 12) △ST(M1) = S1(M1) - T 77K (M1)<0.01eV…(Number 13) • 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.

[0110] The triplet energy was measured as follows. First, the compound to be measured was dissolved in a suitable solvent, and the resulting solution was sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy was calculated based on the wavelength value of the intersection of the tangent and the horizontal axis according to a prescribed conversion formula.

[0111] 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. Although it is difficult to distinguish which state the emission originates from, the triplet energy value is essentially dominant.

[0112] 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. 77KThe compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the band gap T at 77[K]. 77K .

[0113] Conversion formula (F1): T 77K [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.

[0114] 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.

[0115] 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.

[0116] • Lowest excited singlet energy S1 The following methods can be cited as examples of methods for measuring the lowest excited singlet energy S1 using a solution (sometimes called the solution method).

[0117] 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 long 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 lowest excited singlet energy.

[0118] 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.

[0119] 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.

[0120] In addition, the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[0121] • Method for manufacturing the compound of this embodiment The compounds of this embodiment can be manufactured by the synthesis method described in the examples below, or by using known alternative reactions and starting materials that match the target compound.

[0122] Specific examples of compounds in this embodiment Specific examples of compounds used in this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are designated as D in the chemical formula, and protium atoms are designated as H or omitted.

[0123] [Chemistry 29]

[0124] [Chemistry 30]

[0125] [Chemistry 31]

[0126] [Chemistry 32]

[0127] [Chemistry 33]

[0128] [Chemistry 34]

[0129] [Chemistry 35]

[0130] [Chemistry 36]

[0131] [Chemistry 37]

[0132] [Chemistry 38]

[0133] [Chemistry 39]

[0134] [Chemistry 40]

[0135] [Chemistry 41]

[0136] [Chemistry 42]

[0137] [Chemistry 43]

[0138] [Chemistry 44]

[0139] [Chemistry 45]

[0140] [Chemistry 46]

[0141] [Chemistry 47]

[0142] [Chemistry 48]

[0143] [Chemistry 49]

[0144] [Transformation 50]

[0145] [Chemistry 51]

[0146] [Chemistry 52]

[0147] [Chemistry 53]

[0148] [Chemistry 54]

[0149] [Chemistry 55]

[0150] [Chemistry 56]

[0151] [Chemistry 57]

[0152] [Chem.58]

[0153] [Chemistry 59]

[0154] [Transformation 60]

[0155] [Chemistry 61]

[0156] [Chemistry 62]

[0157] [Chemistry 63]

[0158] [Chemistry 64]

[0159] [Chemistry 65]

[0160] [Chemistry 66]

[0161] [Chemistry 67]

[0162] [Chemistry 68]

[0163] [Chemistry 69]

[0164] [Chemistry 70]

[0165] [Chemistry 71]

[0166] [Chemistry 72]

[0167] [Chemistry 73]

[0168] [Chemistry 74]

[0169] [Chemistry 75]

[0170] [Chemistry 76]

[0171] [Chemistry 77]

[0172] [Chemistry 78]

[0173] [Chemistry 79]

[0174] [Chemistry 80]

[0175] [Chemistry 81]

[0176] [Chemistry 82]

[0177] [Chemistry 83]

[0178] [Chemistry 84]

[0179] [Chemistry 85]

[0180] According to this embodiment, a compound with a high PLQY can be provided.

[0181] The measurement method for PLQY is described in the following examples.

[0182] [Second Implementation] (Materials used in organic electroluminescent devices) The material for the organic electroluminescent element in this embodiment contains the compound of the first embodiment. As one example, a material for the organic electroluminescent element containing only the compound of the first embodiment can be cited; as another example, a material for the organic electroluminescent element containing the compound of the first embodiment and other compounds different from those in the first embodiment can be cited.

[0183] In the materials for organic electroluminescent elements according to this embodiment, the compound of the first embodiment is preferably the host material. In this case, the material for the organic electroluminescent element may include the compound of the first embodiment as the host material and other compounds such as dopant materials.

[0184] Furthermore, among the materials for organic electroluminescent elements in this embodiment, the compound of the first embodiment is preferably a delayed fluorescence material.

[0185] [Third Implementation Method] [Organic electroluminescent devices] The organic EL element of this embodiment will be described.

[0186] The organic EL element of this embodiment has an organic layer between the two electrodes, the anode and the cathode. This organic layer comprises at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may also contain inorganic compounds.

[0187] In the organic EL element of this embodiment, the organic layer contains the compound of the first embodiment.

[0188] The organic EL element in this embodiment has a first organic layer as the organic layer.

[0189] In the organic EL element of this embodiment, at least one of the organic layers is preferably a light-emitting layer. In this embodiment, the light-emitting layer preferably contains the compound of the first embodiment.

[0190] The organic layer may be composed of a single light-emitting layer, or it may contain layers that can be used in organic EL devices. There is no particular limitation on the layers that can be used in organic EL devices, and examples include at least one layer selected from the group consisting of hole injection layers, hole transport layers, electron injection layers, electron transport layers, and blocking layers.

[0191] In one embodiment, the first organic layer, which serves as the light-emitting layer, may contain a metal complex.

[0192] Furthermore, in one embodiment, the first organic layer serving as the light-emitting layer preferably does not contain metal complexes.

[0193] Furthermore, in one embodiment, the light-emitting layer preferably does not contain phosphorescent materials (dopant materials).

[0194] Furthermore, in one embodiment, the light-emitting layer is preferably free of heavy metal complexes and phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0195] Figure 3 The diagram shows a schematic configuration of an example of an organic EL element according to this embodiment.

[0196] 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.

[0197] (Emitting layer) In this embodiment, the first organic layer is a light-emitting layer. The first organic layer, serving as the light-emitting layer, comprises a first compound and a second compound. The first compound in the first organic layer is preferably the compound of the first embodiment.

[0198] In this scheme, the first compound is preferably a host material (sometimes also called a matrix material), and the second compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[0199] In this embodiment, when the light-emitting layer contains the compound of the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and more preferably does not contain a metal complex other than a phosphorescent metal complex.

[0200] <First Compound> The first compound is the compound of the first embodiment.

[0201] The first compound is preferably a compound with delayed fluorescence.

[0202] <Second Compound> The second compound is preferably a fluorescent compound that does not exhibit delayed fluorescence.

[0203] As the second compound 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, pyrrole methylene boron complexes, compounds having a pyrrole methylene skeleton, metal complexes of compounds having a pyrrole methylene skeleton, diketopyrrole-pyrrole derivatives, perylene derivatives, and tetraphenyl derivatives.

[0204] In this embodiment, the second compound is preferably a compound represented by the following general formula (2).

[0205] [Chemistry 86]

[0206] In the general formula (2), 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 22 group, R 22 and R 23 group, R 24 and R 25 The group, and R 25 and R 26 A ring is formed by bonding together any one or more groups within a group. 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.

[0207] In the case where the second compound is a fluorescent compound, the second compound preferably exhibits luminescence with a main peak wavelength of 400 nm or more and 700 nm or less.

[0208] In this specification, the main peak wavelength refers to the wavelength at which the measured compound is measured at 10 nm. -6 10 moles per liter or more -5 The fluorescence 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).

[0209] The second compound is preferably one that emits red or green light.

[0210] 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.

[0211] When the second compound is a red fluorescent compound, the main peak wavelength of the second compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less.

[0212] 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.

[0213] When the second compound is a green fluorescent compound, the main peak wavelength of the second compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 530 nm or less.

[0214] 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.

[0215] When the second compound is a blue fluorescent compound, the main peak wavelength of the second compound is preferably 430 nm or more and 480 nm or less, more preferably 445 nm or more and 480 nm or less.

[0216] Method for manufacturing the second compound The second compound can be manufactured using known methods.

[0217] ·Specific examples of the second compound Specific examples of the second compound of this embodiment are shown below. However, the second compound in this invention is not limited to these specific examples.

[0218] Furthermore, the coordination bonds between boron and nitrogen atoms in the pyrrole methylene skeleton can be marked using various methods, including solid lines, dashed lines, arrows, or omissions. In this specification, they are represented by solid lines, dashed lines, or omitted.

[0219] [Chemistry 87]

[0220] [Chemistry 88]

[0221] [Chemistry 89]

[0222] [Chemistry 90]

[0223] [Chemistry 91]

[0224] [Chemistry 92]

[0225] [Chemistry 93]

[0226] <The relationship between the first and second compounds in the luminescent layer> In the organic EL element of this embodiment, it is preferable that the lowest excitation singlet energy S1 (M1) of the first compound and the lowest excitation singlet energy S1 (M2) of the second compound satisfy the following mathematical expression (Equation 3).

[0227] S1(M1) > S1(M2) … (Number 3) The preferred bandgap T is at 77 [K] for the first compound. 77K (M1) is greater than the band gap T when it is greater than 77 [K] of the second compound. 77K (M2). That is, preferably, the relationship satisfies the following mathematical expression (number 5).

[0228] T 77K (M1) > T 77K (M2) … (Number 5) Preferably, when the organic EL element of this embodiment emits light, the second compound mainly emits light in the light-emitting layer.

[0229] • TADF mechanism Figure 4 This is a diagram illustrating an example of the relationship between the energy levels of the second compound M2 and the first compound M1 in the luminescent layer. Figure 4 In this diagram, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of the first compound M1. T1 (M1) represents the lowest excited triplet state of the first compound M1. S1 (M2) represents the lowest excited singlet state of the second compound M2. T1 (M2) represents the lowest excited triplet state of the second compound M2.

[0230] Figure 4 The dashed arrows from S1 (M1) to S1 (M2) in the diagram represent the energy transfer from the lowest excited singlet state of the first compound M1 to the Forster-type energy transfer of the second compound M2.

[0231] like Figure 4As shown, if a compound with a smaller ΔST (M1) is used as the first compound M1, the lowest excited triplet state T1 (M1) can undergo a reverse intersystem crossing to the lowest excited singlet state S1 (M1) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1 (M1) of the first compound M1 to the second compound M2, generating the lowest excited singlet state S1 (M2). As a result, fluorescence emission from the lowest excited singlet state S1 (M2) of the second 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%.

[0232] Preferably, the organic EL element in this embodiment emits red or green light.

[0233] In the case where the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[0234] In the case where the organic EL element in this embodiment emits red light, the main peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less.

[0235] In the case where the organic EL element of this embodiment emits blue light, the main peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0236] The main peak wavelength of light emitted from the organic EL element is measured as described below.

[0237] 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.

[0238] 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).

[0239] • 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.

[0240] • The content of compounds in the luminescent layer The content of the first compound and the second compound contained in the light-emitting layer is preferably within, for example, the following range.

[0241] The content of the first compound is preferably 10% by mass or more and 80% by mass, more preferably 10% by mass or more and 60% by mass, and even more preferably 20% by mass or more and 60% by mass. In addition, the content of the first compound may be 90% by mass or more and 99.9% by mass, 95% by mass or more and 99.9% by mass, or 99% by mass or more and 99.9% by mass.

[0242] The content of the second compound 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.

[0243] Furthermore, this embodiment does not exclude the inclusion of materials other than the first compound and the second compound in the light-emitting layer.

[0244] The luminescent layer may contain only one first compound or two or more first compounds. The luminescent layer may contain only one second compound or two or more second compounds.

[0245] (Substrate) The substrate is used as a support for organic EL elements. 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 made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, inorganic vapor-deposited films can also be used.

[0246] (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).

[0247] 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, and other methods.

[0248] 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.

[0249] It can also use elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), and alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them. Furthermore, when using alkali metals, alkaline earth metals, and their alloys as the anode, vacuum evaporation or sputtering methods can be used. Moreover, when using silver paste, coating or inkjet methods can be used.

[0250] (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), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them.

[0251] 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.

[0252] Furthermore, by incorporating an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, and silicon- or silicon-oxide-containing indium tin oxide, regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[0253] (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.

[0254] 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), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (TDATA). Aromatic amine compounds such as DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as: PCzPCN1) are also mentioned.

[0255] Furthermore, as substances with high hole injection potential, 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.

[0256] (Hole transport layer) The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., 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), 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 Substances with a hole mobility of / Vs or higher.

[0257] In the hole transport layer, carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPANth can also be used. Polymer compounds such as poly(N-vinylcarbazole) (PVK) or poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[0258] However, any material other than these 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 a single layer or a layer obtained by stacking two or more layers of the aforementioned materials.

[0259] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (p-EtTAZ), phenanthroline (BPhen), copper hydroxide (BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (BzOs) can also be used. The substances mentioned here mainly possess 10... -6 cm 2 Materials with an electron mobility of / Vs or higher. Furthermore, any material whose electron transport capacity is higher than its hole transport capacity can also be used as the electron transport layer. In addition, the electron transport layer can be a single layer or a layer formed by stacking two or more layers of the aforementioned materials.

[0260] 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.

[0261] (Electron injection layer) The electron injection layer is a layer containing a material with high electron injection capacity. 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.

[0262] 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 excellent electron injection and electron transport properties. In this case, the organic compound is preferably a material with excellent electron transport properties, specifically, substances constituting the electron transport layer described above (metal complexes or heteroaromatic compounds, etc.) can be used. The electron donor is any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Furthermore, alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, barium oxides, etc. Additionally, Lewis bases such as magnesium oxide can be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[0263] (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.

[0264] (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.

[0265] The organic EL element of the third embodiment includes a compound of the first embodiment as the first compound and a second compound having a lower minimum excitation singlet energy than the first compound in the light-emitting layer.

[0266] The organic EL element of the third embodiment contains the compound of the first embodiment (first compound) with a high PLQY. Therefore, according to the third embodiment, a high-performance organic EL element can be provided. Examples of the performance characteristics of the organic EL element include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0267] The organic EL element of the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0268] [Fourth Implementation Method] The structure of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same reference numerals and names are used for the same components as in the third embodiment, and descriptions are omitted or simplified. Furthermore, in the fourth embodiment, the same materials and compounds as those described in the third embodiment can be used for materials and compounds not specifically mentioned.

[0269] The organic EL element of the fourth embodiment differs from the organic EL element of the third embodiment in that the light-emitting layer further comprises a third compound. Otherwise, it is the same as the third embodiment.

[0270] That is, in the fourth embodiment, the light-emitting layer, which serves as the first organic layer, includes a first compound, a second compound, and a third compound.

[0271] In this scheme, the first compound is preferably the host material, and the second compound is preferably the dopant material.

[0272] <The Third Compound> The third compound can be a compound with delayed fluorescence or a compound without delayed fluorescence.

[0273] While not particularly limited, the third compound is preferably a compound other than an amine compound. Furthermore, carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives can be used as the third compound, but are not limited to these derivatives.

[0274] The third compound is also preferably a compound in which at least one of the following general formula (31), general formula (32), general formula (33A), and general formula (34B) is contained in a molecule.

[0275] [Chemistry 94]

[0276] In the general formula (31), Y 31 ~Y36 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. Among them, Y 31 ~Y 36 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound. In the general formula (32), Y 41 ~Y 48 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. Among them, Y 41 ~Y 48 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound. X 30 Nitrogen, oxygen, or sulfur atoms that are bonded to other atoms in the molecule of the third compound.

[0277] In the general formulas (33A) and (34A), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[0278] In the general formula (32), Y is also preferred. 41 ~Y 48 At least two of them are carbon atoms bonded to other atoms in the molecule of the third compound, forming a ring structure containing the carbon atoms.

[0279] For example, the preferred local structure represented by the general formula (32) is any one of the local structures selected from the group consisting of local structures represented by the following general formulas (321), (322), (323), (324), (325) and (326).

[0280] [Chem. 95]

[0281] [Chemistry 96]

[0282] [Chemistry 97]

[0283] In the general formulas (321) to (326), X 30 Each of the nitrogen, oxygen, or sulfur atoms is independently bonded to other atoms in the molecule of the third compound. Y 41 ~Y 48Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound. X 31 Each of the following is an independent nitrogen atom, oxygen atom, sulfur atom, or carbon atom bonded to other atoms in the molecule of the third compound. Y 61 ~Y 64 Carbon atoms that are either nitrogen atoms or carbon atoms bonded independently to other atoms in the molecule of a third compound.

[0284] In this embodiment, the third compound preferably has a local structure represented by general formula (323) in general formulas (321) to (326).

[0285] The local structure represented by the general formula (31) is preferably contained in the third compound as at least one group selected from the group represented by the general formula (33) and the group represented by the general formula (34).

[0286] The third compound is also preferably having at least one of the local structures represented by the following general formulas (33) and (34). As shown in the local structures represented by the following general formulas (33) and (34), the bonding sites are located at meta positions, thus enabling the third compound to achieve a band gap T at 77 [K]. 77K (M3) remains at a high level.

[0287] [Chem. 98]

[0288] In the general formula (33), Y 31 Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[0289] In the general formula (34), Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[0290] In the general formulas (33) and (34), R 31 Each can be an independent hydrogen atom or a substituent. R as a substituent 31 Independently from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms Substituted or unsubstituted silyl groups Replacement of germanium-based Substituted phosphine oxide group, Halogen atoms, cyano, Nitro, and Choose from the group consisting of substituted or unsubstituted carboxyl groups.

[0291] Wherein, the R 31 The aryl group, whether substituted or unsubstituted, with a cyclic carbon number of 6 to 30, is preferably a non-fused ring.

[0292] In the general formulas (33) and (34), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[0293] In the general formula (33), Y is preferred. 31 Y 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[0294] Furthermore, in the general formula (34), Y is preferred. 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[0295] The preferred substituted germanium-based form is -Ge(R) 301 )3 indicates. R 301 Each is an independent substituent. Substituent R 301 Preferably, it is an alkyl group with 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted. Multiple R 301 They are the same or different from each other.

[0296] The local structure represented by the general formula (32) is preferably contained in the third compound as at least one group selected from the group composed of the groups represented by the following general formulas (35) to (39) and the following general formula (30a).

[0297] [Chemistry 99]

[0298] [Chemistry 100]

[0299] [Chemistry 101]

[0300] In the general formula (35), Y 41 To Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0301] In the general formulas (36) and (37), Y 41 ~Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0302] In the general formula (38), Y 41 Y 42 Y 44 Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0303] In the general formula (39), Y 42 ~Y 48 Each independently consists of a nitrogen atom or CR 32 .

[0304] In the general formula (30a), Y 42 ~Y 47 Each independently consists of a nitrogen atom or CR 32 .

[0305] In the general formulas (35) to (39) and (30a), R 32 Each can be an independent hydrogen atom or a substituent. R as a substituent 32 from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms Substituted or unsubstituted silyl groups Replacement of germanium-based Substituted phosphine oxide group, Halogen atoms, cyano, Nitro, and Choose from the group consisting of substituted or unsubstituted carboxyl groups. Multiple R 32 They are the same or different from each other.

[0306] In the general formulas (37) to (39) and (30a), X 30 For NR 33 oxygen or sulfur atoms R 33 from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms Substituted or unsubstituted silyl groups Replacement of germanium-based Substituted phosphine oxide group, Fluorine atom, cyano, Nitro, and Choose from the group consisting of substituted or unsubstituted carboxyl groups. Multiple R 33 They are the same or different from each other.

[0307] Wherein, the R 33 The aryl group, whether substituted or unsubstituted, with a cyclic carbon number of 6 to 30, is preferably a non-fused ring.

[0308] In the general formulas (35) to (39) and (30a), * independently represents the site where the third compound is bonded to other atoms or other structures in the molecule.

[0309] In the general formula (35), Y is preferred. 41 ~Y 48 CR independently 32In the general formulas (36) and (37), Y is preferred. 41 ~Y 45 Y 47 and Y 48 CR independently 32 In the general formula (38), Y is preferred. 41 Y 42 Y 44 Y 45 Y 47 and Y 48 CR independently 32 In the general formula (39), Y is preferred. 42 ~Y 48 CR independently 32 In the general formula (30a), Y is preferred. 42 ~Y 47 CR independently 32 Multiple R 32 They are the same or different from each other.

[0310] In the third compound, X 30 Preferably, it contains oxygen atoms or sulfur atoms, and more preferably oxygen atoms.

[0311] In the third compound, R is preferred. 31 and R 32 R can be a hydrogen atom or a substituent, and can be a substituent. 31 And R as a substituent 32 Each group is independently selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms. More preferably, R 31 and R 32 It consists of a hydrogen atom, a cyano group, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 5 to 30 substituted or unsubstituted cyclic atoms. Specifically, R, as a substituent... 31 And R as a substituent 32 When the aryl group is a substituted or unsubstituted cyclic carbon group with a carbon number of 6 to 30, the aryl group is preferably a non-fused ring.

[0312] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[0313] • Method for manufacturing the third compound The third compound can be manufactured by methods described, for example, in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650. Furthermore, the third compound can be manufactured, for example, by using known alternative reactions and starting materials that match the target compound.

[0314] Examples of substituents in the third compound are shown below, but the invention is not limited to these examples.

[0315] Specific examples of aryl groups (sometimes called aromatic hydrocarbon groups) include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrene, phenyl, benzo[c]phenanthryl, benzo[g]phenyl, benzo[anthracene], triphenylene, fluorenyl, 9,9-dimethylfluorenyl, benzo[anthracene]fluorenyl, dibenzo[anthracene]fluorenyl, biphenyl, triphenyl, tetraphenyl, fluoranthyl, etc., with phenyl, biphenyl, triphenyl, tetraphenyl, naphthyl, triphenylene, and fluorenyl being preferred examples.

[0316] Examples of aryl groups with substituents include tolyl, xylyl, and 9,9-dimethylfluorenyl.

[0317] As illustrated in the specific example, aryl groups include both fused aryl groups and unfused aryl groups.

[0318] The preferred aryl group is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, triphenylene, or fluorene.

[0319] Specific examples of heteroaryl groups (sometimes called heterocyclic groups, heteroaromatic cyclic groups, or aromatic heterocyclic groups) include pyrroloyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolyl, isoyindolyl, imidazolyl, benzimidazolyl, indolyl, imidazo[1,2-a]pyridyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, azadibenzothiophenyl, and quinoline. The group can be categorized into several groups, including quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, naphridinyl, carbazoleyl, azacarbazoleyl, phenanthinyl, acridineyl, phenanthrololinyl, phenazinyl, phenothiazinyl, phenotoxazinyl, oxazolyl, oxadiazolyl, furo-coryl, benzoxoxazolyl, thiophenyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., with preferred examples being dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothiophenyl.

[0320] As a heteroaryl group, it is preferably dibenzofuranyl, dibenzothiophene, carbazoyl, pyridyl, pyrimidinyl, triazine, azidodibenzofuranyl or azidodibenzothiophene, and more preferably dibenzofuranyl, dibenzothiophene, azidodibenzofuranyl or azidodibenzothiophene.

[0321] In the third compound, the substituted silyl group is preferably selected from the group consisting of substituted or unsubstituted trialkylsilyl groups, substituted or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups.

[0322] Specific examples of substituted or unsubstituted trialkylsilyl compounds include trimethylsilyl and triethylsilyl.

[0323] Specific examples of substituted or unsubstituted arylalkylsilyl compounds include diphenylmethylsilyl, xylylmethylsilyl, and phenyldimethylsilyl.

[0324] Specific examples of substituted or unsubstituted triarylsilyl compounds include triphenylsilyl and trimethylsilyl.

[0325] In the third compound, the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group.

[0326] Specific examples of substituted or unsubstituted diarylphosphine oxides include diphenylphosphine oxide and xylylphosphine oxide.

[0327] In the third compound, substituted carboxyl groups can be exemplified by, for example, benzoyloxy groups.

[0328] Specific examples of the third compound Specific examples of the third compound in this embodiment are shown below. However, the third compound in this invention is not limited to these specific examples.

[0329] [Chemistry 102]

[0330] [Chemistry 103]

[0331] [Chemistry 104]

[0332] [Chemistry 105]

[0333] <The relationship between the first, second, and third compounds in the luminescent layer> In the organic EL element of this embodiment, it is preferable that the lowest excitation singlet energy S1 (M1) of the first compound and the lowest excitation singlet energy S1 (M3) of the third compound satisfy the following mathematical expression (Equation 2).

[0334] S1(M3)>S1(M1) (Number 2) The band gap T at 77 [K] is preferably that of the third compound. 77K (M3) The band gap T when it is greater than 77 [K] of the first compound 77K (M1).

[0335] The band gap T at 77 [K] is preferably that of the third compound. 77K (M3) has a band gap T greater than 77 [K] for the second compound. 77K (M2).

[0336] Preferably, the lowest excited singlet state energy S1 (M1) of the first compound, the lowest excited singlet state energy S1 (M2) of the second compound, and the lowest excited singlet state energy S1 (M3) of the third compound satisfy the following mathematical expression (Equation 2A).

[0337] S1(M3)>S1(M1)>S1(M2)…(Number 2A) The preferred bandgap T is at 77 [K] for the first compound. 77K The band gap T of (M1) and the second compound at 77 [K] 77K The band gap T of (M2) and the third compound at 77 [K] 77K (M3) satisfies the following mathematical expression (number 2B).

[0338] T 77K (M3) > T 77K (M1) > T 77K (M2) … (Number 2B) Preferably, when the organic EL element of this embodiment emits light, the light-emitting layer mainly contains fluorescent compounds that emit light.

[0339] Preferably, the organic EL element of this embodiment emits red light or green light in the same way as the organic EL element of the third embodiment.

[0340] The peak wavelength of light emitted from the organic EL element can be measured using the same method as the organic EL element in the third embodiment.

[0341] • The content of compounds in the luminescent layer The content of the first compound, the second compound, and the third compound contained in the light-emitting layer is preferably within, for example, the following range.

[0342] The content of the first compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[0343] The content of the second compound 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.

[0344] The content of the third compound is preferably 10% by mass or more and 80% by mass or less.

[0345] The maximum allowed content of the first compound, the second compound, and the third compound in the light-emitting layer is 100% by mass. Furthermore, it is not excluded that this embodiment may include materials other than the first compound, the second compound, and the third compound in the light-emitting layer.

[0346] The luminescent layer may contain only one first compound or two or more first compounds. The luminescent layer may contain only one second compound or two or more second compounds. The luminescent layer may contain only one third compound or two or more third compounds.

[0347] Figure 5 This is a diagram illustrating an example of the relationship between the energy levels of the first, second, and third compounds in the luminescent layer. Figure 5 In this diagram, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of the first compound, and T1 (M1) represents the lowest excited triplet state of the first compound. S1 (M2) represents the lowest excited singlet state of the second compound, and T1 (M2) represents the lowest excited triplet state of the second compound. S1 (M3) represents the lowest excited singlet state of the third compound, and T1 (M3) represents the lowest excited triplet state of the third compound. Figure 5 The dashed arrows from S1(M1) to S1(M2) represent Foster-type energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound.

[0348] like Figure 5 As shown, if a compound with a smaller ΔST (M1) is used as the first compound, the lowest excited triplet state T1 (M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M1) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1 (M1) of the first compound to the lowest excited singlet state S1 (M2) of the second compound, generating the lowest excited singlet state S1 (M2). As a result, fluorescence emission from the lowest excited singlet state S1 (M2) of the second compound can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0349] The organic EL element of the fourth embodiment includes, in the light-emitting layer, a compound of the first embodiment as the first compound, a second compound having a lower minimum excitation singlet energy than the first compound, and a third compound having a higher minimum excitation singlet energy than the first compound.

[0350] The organic EL element of the fourth embodiment contains the compound of the first embodiment (first compound) with a high PLQY, and therefore, according to the fourth embodiment, a high-performance organic EL element can be provided.

[0351] The organic EL element of the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0352] [Fifth Implementation Method] The structure of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same reference numerals and names as those in the third or fourth embodiment are used, and descriptions are omitted or simplified. Furthermore, in the fifth embodiment, the same materials and compounds as those described in the third or fourth embodiment can be used for materials and compounds not specifically mentioned.

[0353] The organic EL element of the fifth embodiment differs from the organic EL elements of the third or fourth embodiments in that the light-emitting layer contains the first compound and the third compound but not the second compound. Otherwise, it is the same as the third or fourth embodiments.

[0354] That is, in the fifth embodiment, the light-emitting layer, which is the first organic layer, includes the first compound and the third compound.

[0355] In this scheme, the third compound is preferably the host material, and the first compound is preferably the dopant material.

[0356] In this embodiment, when the light-emitting layer contains the compound of the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and more preferably does not contain a metal complex other than a phosphorescent metal complex.

[0357] <First Compound> The first compound is the compound of the first embodiment.

[0358] The first compound is preferably a compound with delayed fluorescence.

[0359] <The Third Compound> The third compound is the same as the third compound described in the fourth embodiment.

[0360] <The relationship between the first and third compounds in the luminescent layer> In the organic EL element of this embodiment, it is preferable that the lowest excitation singlet energy S1 (M1) of the first compound and the lowest excitation singlet energy S1 (M3) of the third compound satisfy the following mathematical expression (Equation 2).

[0361] S1(M3)>S1(M1) (Number 2) The band gap T at 77 [K] is preferably that of the third compound. 77K (M3) The band gap T when it is greater than 77 [K] of the first compound 77K (M1).

[0362] Figure 6 This diagram illustrates the principle of light emission according to an embodiment of the present invention.

[0363] Figure 6 In this diagram, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of the first compound, and T1 (M1) represents the lowest excited triplet state of the first compound. S1 (M3) represents the lowest excited singlet state of the third compound, and T1 (M3) represents the lowest excited triplet state of the third compound.

[0364] like Figure 6 As shown, if a compound with a smaller ΔST (M1) is used as the first compound, the lowest excited triplet state T1 (M1) of the first compound can be reverse-intersystemed through thermal energy to the lowest excited singlet state S1 (M1).

[0365] By utilizing the reverse intersystem crossing generated in the first compound, for example, luminescence as shown in (i) or (ii) below can be observed.

[0366] (i) In the absence of a fluorescent dopant in the luminescent layer that has a minimum excited singlet state S1 less than the minimum excited singlet state S1 (M1) of the first compound, luminescence from the minimum excited singlet state S1 (M1) of the first compound can be observed.

[0367] (ii) When the luminescent layer contains a fluorescent dopant whose lowest excitation singlet state S1 is less than the lowest excitation singlet state S1 (M1) of the first compound (or a fluorescent second compound in the third or fourth embodiment), luminescence from the fluorescent dopant can be observed.

[0368] Furthermore, the light emission shown in (i) above can be observed in the organic EL element of this embodiment. The light emission shown in (ii) above can be observed in the organic EL element of the third or fourth embodiment described above.

[0369] • The content of compounds in the luminescent layer The content of the first compound and the third compound contained in the light-emitting layer is preferably within, for example, the following range.

[0370] The content of the first compound is preferably 10% by mass or more and 90% by mass, more preferably 10% by mass or more and 80% by mass, even more preferably 10% by mass or more and 60% by mass, and even more preferably 20% by mass or more and 60% by mass.

[0371] The content of the third compound is preferably 10% by mass or more and 90% by mass or less.

[0372] The maximum combined content of the first and third compounds in the luminescent layer is 100% by mass.

[0373] The luminescent layer may contain only one first compound or two or more first compounds. The luminescent layer may contain only one third compound or two or more third compounds.

[0374] The organic EL element of the fifth embodiment contains the compound of the first embodiment (first compound) with a high PLQY, and therefore, according to the fifth embodiment, a high-performance organic EL element can be provided.

[0375] The organic EL element of the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0376] [Sixth 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 lights.

[0377] [Other Notes] In this specification, the mutual bonding of Rx and Ry to form a ring means, for example, that Rx and Ry contain carbon, nitrogen, oxygen, sulfur, or silicon atoms, and that the atoms in Rx (carbon, nitrogen, oxygen, sulfur, or silicon) are bonded to the atoms in Ry (carbon, nitrogen, oxygen, sulfur, or silicon) via single, double, triple, or divalent connecting groups to form a ring with five or more ring atoms (specifically, a heterocycle or aromatic hydrocarbon ring). x is a number, a letter, or a combination of numbers and letters. y is a number, a letter, or a combination of numbers and letters.

[0378] 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.

[0379] 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.

[0380] 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.

[0381] 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.

[0382] 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).

[0383] In general formulas (E1) to (I1), * independently represents the position where the atom bonds to 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).

[0384] [Chemistry 106]

[0385] [Chemistry 107]

[0386] 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 indicates the position bonded to 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).

[0387] 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.

[0388] 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), the asterisks independently indicate the positions where the molecules are bonded to other atoms in a molecule.

[0389] [Chemistry 108]

[0390] 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. This also applies to the "number of carbon atoms forming the ring" described below 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.

[0391] 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 (including spirofluorene rings) is bonded to a fluorene ring, the number of atoms of the fluorene ring as a substituent is not included in the number of cyclic atoms.

[0392] • Explanation of each substituent in the general formula (Explanation of each substituent) Next, the substituents in the general formulas in this specification will be explained.

[0393] In this specification, the aryl group (sometimes referred to as an aromatic hydrocarbon group) is, for example, aryl Sub1. As aryl Sub1, the number of carbon atoms in the ring is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 14, and even more preferably 6 to 12.

[0394] The aryl Sub1 in this specification is, for example, 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.

[0395] Among the aryl Sub1 groups described above, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, and fluorenyl are preferred. For 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, and 4-fluorenyl groups, the carbon atom at the 9-position is preferably substituted with a substituted or unsubstituted alkyl Sub3 or a substituted or unsubstituted aryl Sub1 group as described later in this specification.

[0396] In this specification, the heteroaryl group (sometimes referred to as a heterocyclic group, heteroaromatic cyclic group, or aromatic heterocyclic group) is, for example, a 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. The heterocyclic group Sub2 is preferably a group comprising at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom. As the heterocyclic group Sub2, the number of cyclic atoms is preferably 5 to 30, more preferably 5 to 20, and even more preferably 5 to 14.

[0397] 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.

[0398] More preferably, among the aforementioned heterocyclic groups Sub2, are 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. For 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, and 4-carbazoleyl, the nitrogen atom at the 9-position is preferably substituted with a substituted or unsubstituted aryl group Sub1 or a substituted or unsubstituted heterocyclic group Sub2 as described in this specification.

[0399] Furthermore, in this specification, the heterocyclic group Sub2 may also be a group derived from a local structure represented by the following general formulas (XY-1) to (XY-18).

[0400] [Chemistry 109]

[0401] [Chemical 110]

[0402] [Chemistry 111]

[0403] 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.

[0404] 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.

[0405] [Chemistry 112]

[0406] The alkyl group in this specification can be any one of straight-chain alkyl, branched alkyl, or cyclic alkyl.

[0407] In this specification, alkyl groups are, for example, alkyl Sub3.

[0408] In this specification, straight-chain alkyl groups are, for example, straight-chain alkyl sub. 31 .

[0409] In this specification, branched alkyl groups are, for example, branched alkyl subs. 32 .

[0410] The cyclic alkyl group in this specification is, for example, a cyclic alkyl sub. 33 (Sometimes referred to as cycloalkyl sub) 331 ).

[0411] 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.

[0412] 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 even more preferably 1 to 6.

[0413] The cycloalkyl sub in this specification 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. Cycloalkyl Sub 331 The number of carbon atoms in the ring is preferably 3 to 6.

[0414] The straight-chain alkyl sub in this specification 31 or branched alkyl sub 32For 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.

[0415] 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.

[0416] The cyclic alkyl sub in this specification 33 For example, cycloalkyl Sub 331 .

[0417] 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. In cycloalkyl Sub 331 More preferably, cyclopentyl or cyclohexyl.

[0418] In this specification, alkyl halogens are, for example, alkyl halogens Sub4, which are alkyl groups obtained by substituting one or more halogen atoms, preferably fluorine atoms, into alkyl groups Sub3.

[0419] 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.

[0420] In this specification, substituted silyl groups are, for example, substituted silyl Sub5, and substituted silyl Sub5 is, for example, derived from alkyl silyl Sub. 51 and arylsilyl Sub 52 At least one group selected from the group constitutes the composition.

[0421] The alkylsilyl sub in this specification 51 For example, a trialkylsilyl sub-sub-containing alkyl Sub3 as described above. 511 .

[0422] Trialkylsilyl Sub 511For 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.

[0423] 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.

[0424] 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.

[0425] Alkyl diarylsilyl sub 522 For 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.

[0426] 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.

[0427] 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.

[0428] 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.

[0429] 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. In this aralkyl Sub7, the aryl moiety preferably has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl moiety preferably 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, selected from 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.

[0430] In this specification, the alkoxy group is, for example, alkoxySub8, which is represented as -OZ1. Z1 is, for example, the aforementioned alkylSub3.

[0431] The number of carbon atoms in the alkoxy Sub8 is preferably 1 to 30, more preferably 1 to 20.

[0432] Alkoxy Sub8 is, for example, at least one group selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy.

[0433] 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.

[0434] The aryloxy group (sometimes called arylalkoxy) in this specification is, for example, arylalkoxySub. 10 Arylalkoxy Sub 10 The aryl group in the aryl group includes at least one of aryl Sub1 and heteroaryl Sub2.

[0435] 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 formation is 6 to 30, more preferably 6 to 20. As this arylalkoxy Sub 10 For example, phenoxy groups can be cited.

[0436] In this specification, substituted amino groups are, for example, substituted amino sub. 11 Subsubstituted amino groups 11For example, from arylaminosub 111 and alkylamino Sub 112 At least one group selected from the group constitutes the composition.

[0437] 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.

[0438] Alkylamino Sub 112 Represented as -NHR V2 or -N(R) V2 2.

[0439] The R V2 For example, alkyl Sub3-N(R) V2 The two R's in 2) V2 Same or different.

[0440] 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.

[0441] 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.

[0442] In this specification, the alkylthio group is, for example, alkylthio group Sub. 14 .

[0443] 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.

[0444] In this specification, the aryl thio group is, for example, aryl thio group Sub. 15 .

[0445] Arylthiosub 15 Represented as -SRV4 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.

[0446] Examples of halogen atoms in this specification include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms being preferred.

[0447] 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.

[0448] 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.

[0449] 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.

[0450] 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).

[0451] [Chemistry 113]

[0452] 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.

[0453] In this specification, the ester group is, for example, the ester group Sub. 20 ester group Sub 20 For example, at least one group selected from the group consisting of alkyl esters and aryl esters.

[0454] 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) ORE R E For example, the above-mentioned alkyl Sub3 (preferably with 1 to 10 carbon atoms) may be substituted or unsubstituted.

[0455] In this specification, the aryl ester group is, for example, an aryl ester group Sub. 202 aryl ester group Sub 202 Represented as -C (=O) OR Ar R Ar For example, the above-mentioned aryl Sub1 may be substituted or unsubstituted.

[0456] 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.

[0457] In this specification, the carbamoyl group is represented as -CONH2.

[0458] 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.

[0459] R C For example, the above-mentioned alkyl Sub3 (preferably with 1 to 6 carbon atoms) may be substituted or unsubstituted.

[0460] 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 heteroatoms that constitute a heterocycle (including saturated rings, unsaturated rings, and aromatic rings).

[0461] In this specification, "hydrogen atom" unless otherwise specified as "protium atom" or "deuterium atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0462] In this specification, hydrogen atoms are assumed to be bonded at bonding positions in the chemical structural formula, not explicitly shown in the symbols such as "R" or "D" representing a deuterium atom, i.e., protium, deuterium, or tritium atoms are bonded.

[0463] 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 Any one or more groups in it.

[0464] Similarly, substituted silyl Sub5 refers to alkyl silyl Sub. 51 and arylsilyl Sub 52 Any one or more groups in it.

[0465] Similarly, substituted amino Sub 11 It refers to arylamino Sub 111 and alkylamino Sub 112 Any one or more groups in it.

[0466] In this specification, a substituent is referred to as "substituted or unsubstituted" in such cases, for example, substituent R. F1 , substituent R F1 From aryl Sub1, heteroaryl Sub2, alkyl Sub3, haloalkyl Sub4, substituted silyl Sub5, alkylsulfonyl Sub6, aralkyl Sub7, alkoxy Sub8, haloalkoxy Sub9, arylalkoxy Sub 10 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based 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 thiol group, a nitro group, and a carboxyl group.

[0467] 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 B2Ar in B- B1 And Ar B2 Same or different.

[0468] 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 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 and carbamoyl Sub 22 ) Specific examples and preferred groups are the same groups.

[0469] 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 Substituted amino groups 11 Alkenyl Sub 12 , acetylinyl Sub 13 alkylthiosub 14 arylthiosub 15 Substituted phosphine-based Sub 16 aryl carbonyl Sub 17 Acyl Sub 18 Substituted phosphoryl group Sub 19 , ester group Sub 20 Siloxane Sub 21 Carbamoyl Sub 22 At least one group selected from the group consisting of unsubstituted amino, unsubstituted silyl, halogen atom, cyano, hydroxyl, thiol, nitro and carboxyl (hereinafter also referred to as substituent R) F2 Further substitution. In addition, these multiple substituents R F2They can also bond together to form a ring.

[0470] In the case of "substituted or unsubstituted", "unsubstituted" means not substituted by the substituent R. F1 It is replaced by hydrogen atoms that are bonded together.

[0471] 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.

[0472] 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.

[0473] The same applies to the cases of "substituted or unsubstituted" in the compounds or their partial structures described in this specification.

[0474] 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.

[0475] 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.

[0476] 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.

[0477] In this specification, the numerical range represented by "AA~BB" refers to the range including the value AA before "AA~BB" as the lower limit and the value BB after "AA~BB" as the upper limit.

[0478] [Changes in Implementation Method] Furthermore, the present invention is not limited to the above-described embodiments, and modifications and improvements made within the scope of achieving the purpose of the present invention are included within the present invention.

[0479] For example, the light-emitting layer is not limited to one 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 satisfies 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 from the triplet excited state to the ground state.

[0480] 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 intermediate layers in between.

[0481] 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.

[0482] For example, when a barrier layer is grounded on the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the cathode side layer (e.g., an 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.

[0483] Furthermore, when a blocking layer is grounded on the anode side of the light-emitting layer, this blocking layer transports holes and prevents electrons from reaching the anode side layer of the blocking 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 blocking layer between the light-emitting layer and the hole transport layer.

[0484] 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).

[0485] Preferably, the light-emitting layer is bonded to the blocking layer.

[0486] 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.

[0487] Example The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[0488] <Compound> The structures of the compounds represented by general formula (1) in Examples 1-16 or Synthetic Examples 1-10 are shown below.

[0489] [Chemistry 114]

[0490] [Chemistry 115]

[0491] [Chemistry 116]

[0492] [Chemistry 117]

[0493] The structures of the comparative compounds in Comparative Examples 1 to 4 are shown below.

[0494] [Chemistry 118]

[0495] The structures of the compounds used to manufacture organic EL elements in Examples 10-16 and Comparative Examples 3-4 are shown below.

[0496] [Chemistry 119]

[0497] [Chemistry 120]

[0498] [Chemistry 121]

[0499] [Chemistry 122]

[0500] <Compound Evaluation> (Preparation of toluene solution) Compound A1 was dissolved in toluene to achieve a concentration of 5 μmol / L, thus preparing a toluene solution of compound A1. The prepared solution was then bubbled with nitrogen for 5 minutes, and the system was sealed to prevent the ingress of outside air.

[0501] For compounds A2, A3, A4, A5, A6, A7, A8, A9, Ref-1, and Ref-2, toluene solutions were prepared in the same manner as for compound A1. The prepared solutions were then bubbled with nitrogen for 5 minutes and sealed to prevent the ingress of external air.

[0502] (Measurement of fluorescence quantum yield (PLQY)) For the toluene solutions of compounds A1, A2, A3, A4, A5, A6, A7, A8, A9, Ref-1, and Ref-2, PLQY was measured using an absolute PL (photoluminescence) quantum yield measurement device, Quantaurus-QY (manufactured by Hamamatsu Photonics Co., Ltd.).

[0503] The PLQY values ​​of compounds A1, A2, A3, A4, A5, A6, A7, A8, A9, Ref-1, and Ref-2 are shown in Tables 1 and 2. Table 1 shows the relative PLQY values ​​when the PLQY of Comparative Example 1 is set to 100. Table 2 shows the relative PLQY values ​​when the PLQY of Comparative Example 2 is set to 100. Specifically, the values ​​were calculated using the following mathematical formula.

[0504] (Relative PLQY values ​​in Table 1) = {(Absolute PLQY values ​​of compounds in each example or comparative example in Table 1) / (Absolute PLQY value of comparative compound Ref-1)} × 100 (Relative PLQY values ​​in Table 2) = {(Absolute PLQY values ​​of compounds in each example or comparative example in Table 2) / (Absolute PLQY value of comparative compound Ref-2)} × 100 (Main peak wavelength of the compound) A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The fluorescence spectrum of the sample was measured at room temperature (300 K) (vertical axis: fluorescence intensity, horizontal axis: wavelength). In this embodiment, a Hitachi spectrophotometer (device name: F-7000) was used to measure the fluorescence spectrum. However, the fluorescence spectroscopy measuring device is not limited to the one used herein. In the fluorescence spectrum, the wavelength of the peak with the highest fluorescence intensity is taken as the main peak wavelength.

[0505] The peak wavelengths of the fluorescence spectra of compounds A1, A2, A3, A4, A5, A6, A7, A8, A9, Ref-1, and Ref-2 are shown in Tables 1 and 2.

[0506] (Thermal activated delayed fluorescence) Delayed fluorescence of compound A1 Delayed fluorescence by utilizing Figure 1 The apparatus shown is used to measure the transition PL for confirmation. Compound A1 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 oxygen-induced extinction, the sample solution is frozen and degassed before being sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[0507] 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.

[0508] Upon excitation by pulsed light (light irradiated by a pulsed laser) at a wavelength absorbed by compound A1, 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.

[0509] 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 1 The device described in the text.

[0510] For compound A1, it was confirmed that the amount of delayed luminescence was more than 5% relative to the amount of prompt luminescence.

[0511] Specifically, for compound A1, X was identified. D / X P The value is above 0.05.

[0512] In the table, the ">0.05" marker indicates X D / X P The value is greater than 0.05.

[0513] Delayed fluorescence of compounds A2–A9, comparative compound Ref-1, and comparative compound Ref-2 Except for replacing compound A1 with compounds A2-A9, comparative compound Ref-1, and comparative compound Ref-2 respectively, the delayed fluorescence of compounds A2-A9, comparative compound Ref-1, and comparative compound Ref-2 was confirmed in the same manner as described above.

[0514] For compounds A2–A9, comparative compound Ref-1, and comparative compound Ref-2, X D / X P The values ​​are all above 0.05.

[0515] (Singlet energy S1) The singlet energies S1 of compounds A1–A9, comparative compound Ref-1, and comparative compound Ref-2 were measured using the solution method described above. The measurement results are shown in Tables 1 and 2.

[0516] (△ST) T values ​​for compounds A1–A9, comparative compound Ref-1, and comparative compound Ref-2 77K Measurements were performed. The band gap T, as described in the section on "Relationship between Triplete Energy and Band Gap at 77 [K]", was used. 77K The measurement method measures the T values ​​of compounds A1–A9, comparative compound Ref-1, and comparative compound Ref-2. 77K .

[0517] Based on the above value of the singlet energy S1 and T 77K The value of ΔST was used to confirm the value of ΔST. The values ​​of ΔST for each compound are shown in Table 1 and Table 2. In the tables, the notation "<0.01" indicates that ΔST is less than 0.01 eV.

[0518] [Table 1]

[0519] [Table 2]

[0520] As shown in Table 1, PLQY is improved according to compounds A1 to A4 represented by the general formula (1) compared to the comparative compound Ref-1, which has the same p-dicyanophenyl skeleton.

[0521] As shown in Table 2, PLQY is improved according to compounds A5 to A9 represented by the general formula (1) compared to the comparative compound Ref-2, which has the same m-dicyanophenyl skeleton.

[0522] <Fabrication of Organic EL Components> Organic EL elements were fabricated and evaluated as described below.

[0523] (Example 10) 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.

[0524] The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HT-1 and compound 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-1 in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[0525] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 110 nm.

[0526] Next, compound HT-2 is deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[0527] Next, the compound CBP is deposited on the second hole transport layer to form an electron blocking layer with a thickness of 5 nm.

[0528] Next, compound Matrix-1 (as the third compound), compound Matrix-2, and compound A5 (as the first compound) were co-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 25 nm. The concentrations of compound Matrix-1, compound Matrix-2, and compound A5 in the light-emitting layer were set to 25% by mass and 50% by mass, respectively.

[0529] Next, compound ET-1 is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 5 nm.

[0530] Next, compound ET-2 was deposited on the hole blocking layer to form an electron transport layer with a thickness of 50 nm.

[0531] 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.

[0532] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[0533] If the component configuration of the organic EL element of Example 10 is shown in a simplified manner, it is as follows.

[0534] ITO (130) / HT-1: HA (10, 97%: 3%) / HT-1 (110) / HT-2 (5) / CBP (5) / Matrix-1: Matrix-2: A5 (25, 25%: 25%: 50%) / ET-1 (5) / ET-2 (50) / LiF (1) / Al (80) Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[0535] Within the same brackets, the percentage figures (97%: 3%) indicate the proportions (mass%) of compounds HT-1 and HA in the hole injection layer, and the percentage figures (25%: 25%: 50%) indicate the proportions (mass%) of compounds Matrix-1, Matrix-2, and A5 in the luminescent layer. The same labeling applies below.

[0536] (Examples 11-13) Except for changing the first compound in the light-emitting layer of Example 10 to the first compound described in Table 3, the organic EL elements of Examples 11 to 13 were fabricated in the same manner as in Example 10.

[0537] (Comparative Example 3) Except that the first compound in the light-emitting layer of Example 10 was changed to the first compound described in Table 3, the organic EL element of Comparative Example 3 was made in the same manner as in Example 10.

[0538] (Example 14) Except for the modification of the light-emitting layer in Example 10 as described below, the organic EL element of Example 14 is fabricated in the same manner as in Example 10.

[0539] The light-emitting layer of the organic EL element in Example 14 is shown in Table 4. Compound Matrix-1 and Compound Matrix-2 (as the third compound), Compound A5 (as the first compound), and Compound GD (as the second compound) were co-deposited to form a light-emitting layer with a thickness of 25 nm. The concentrations of Compound Matrix-1, Compound Matrix-2, Compound A5, and Compound GD in the light-emitting layer were set to 24.5% by mass, 24.5% by mass, 50% by mass, and 1% by mass.

[0540] (Examples 15-16) Except that the first compound in the light-emitting layer of Example 14 was changed to the first compound listed in Table 4, the organic EL elements of Examples 15 and 16 were made in the same manner as in Example 14.

[0541] (Comparative Example 4) Except that the first compound in the light-emitting layer of Example 14 was changed to the first compound described in Table 4, the organic EL element of Comparative Example 4 was made in the same manner as in Example 14.

[0542] <Evaluation of Organic EL Components> • 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).

[0543] Table 3 shows the relative values ​​of the driving voltage of the organic EL element of Examples 10 to 13 or Comparative Example 3 to the driving voltage of the organic EL element of Comparative Example 3 when the driving voltage of the organic EL element of Comparative Example 3 is set to 1.00.

[0544] Driving voltage (relative value) = [Driving voltage of the organic EL element in Examples 10-13 or Comparative Example 3] / [Driving voltage of the organic EL element in Comparative Example 3] [Table 3]

[0545] Table 4 shows the relative values ​​of the driving voltage of the organic EL element of Examples 14 to 16 or Comparative Example 4 relative to the driving voltage of the organic EL element of Comparative Example 4 when the driving voltage of the organic EL element of Comparative Example 4 is set to 1.00.

[0546] Drive voltage (relative value) = [Drive voltage of the organic EL element in Examples 14-16 or Comparative Example 4] / [Drive voltage of the organic EL element in Comparative Example 4] [Table 4]

[0547] As can be clearly seen from Tables 3 and 4, the driving voltage of the organic EL element using the compound represented by the general formula (1) is reduced compared to the organic EL element using the comparative compound Ref-2, which has the same m-dicyanophenyl skeleton.

[0548] <Modifications of the Embodiments> In Examples 10-13 described in Table 3, compounds Matrix-1 and Matrix-2 were used as the third compound. As a variation of these examples, for example, an organic EL element using only compound Matrix-1 as the third compound can be fabricated. The compounds in the light-emitting layer under such a variation of Examples 10-13 are shown in Table 5 below.

[0549] [Table 5]

[0550] <Compound Synthesis> (Synthesis Example 1) The following describes the synthesis method of compound A1.

[0551] [Chemistry 123]

[0552] Under a nitrogen atmosphere, 1,4-dibromo-2,5-difluorobenzene (15.2 g, 55.9 mmol), copper(I) chloride (13.8 g, 139 mmol), and NMP (200 mL) were added to a 500 mL flask and heated and stirred at 170 °C. After 4 hours of heating and stirring, the material in the flask was heated to 175 °C and stirred for another hour, then cooled to room temperature. After cooling, 200 mL of water was added to the flask, and the precipitated solid was removed by filtration through diatomaceous earth. The filtrate was extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine. The washed organic layer was dried with magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure. The compound obtained after depressurization was purified by silica gel column chromatography to give 1,4-dichloro-2,5-difluorobenzene (4.11 g, 22.5 mmol). NMP is an abbreviation for N-methyl-2-pyrrolidone.

[0553] Under a nitrogen atmosphere, 1,4-dichloro-2,5-difluorobenzene (4.11 g, 22.5 mmol), trimethylchlorosilane (6.3 mL, 50 mmol), and THF (25 mL) were added to a 200 mL three-necked flask. After cooling the contents of the flask to -78 °C using a dry ice / acetone bath, the prepared LDA was added dropwise. The solution obtained after adding all the LDA was stirred at room temperature for 2 hours. After stirring, water (10 mL) was added to the three-necked flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried with magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure. The obtained 2,5-dichloro-3,6-difluoro-1,4-phenylenebistrimethylsilane (6.61 g, 20.2 mmol) was used in the next reaction without purification. Trimethylchlorosilane is sometimes abbreviated as TMSCl. LDA is short for Lithium Diisopropyl Amide.

[0554] Under a nitrogen atmosphere, 2,5-dichloro-3,6-difluoro-1,4-phenylenebistrimethylsilane (6.61 g, 20.2 mmol) and dichloromethane (100 mL) were added to a 500 mL pear-shaped flask. Iodine monochloride (2.5 mL) was added dropwise at room temperature, and the mixture was stirred at 40 °C. Every 2 hours, iodine monochloride (0.5 mL) was added dropwise to the reaction system, for a total of 4.5 mL. After all the iodine monochloride had been added, the mixture was stirred for another 1 hour and 30 minutes, and then allowed to return to room temperature. Next, a saturated sodium thiosulfate aqueous solution (20 mL) was added to the pear-shaped flask, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, and then dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to obtain 1,4-dichloro-2,5-difluoro-3,6-diiodobenzene (6.20 g, 14.3 mmol). DCM is an abbreviation for dichloromethane.

[0555] In a 5 mL vial, 1,4-dichloro-2,5-difluoro-3,6-diiodobenzene (435 mg, 1.0 mmol), copper cyanide (360 mg, 4.0 mmol), and DMF (5 mL) were added, and the mixture was heated and stirred at 150 °C. After 1 hour and 30 minutes, the mixture was cooled to room temperature, and then the reaction solution was injected into 10 mL of ammonia water. Next, the organic layer was extracted with dichloromethane, washed with water and brine, and dried over magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after solvent removal under reduced pressure was purified by silica gel column chromatography to obtain 1,4-dicyano-2,5-dichloro-3,6-difluorobenzene (160 mg). DMF is an abbreviation for N,N-dimethylformamide.

[0556] [Chemistry 124]

[0557] Under a nitrogen atmosphere, 2,5-dichloro-3,6-difluoroterephthalonitrile (16.3 g, 70 mmol), phenylboronic acid (17.9 g, 147 mmol), Pd₂dba₃ (1.60 g, 1.75 mmol), P(t-Bu)₃HBF₄ (1.01 g, 3.5 mmol), DME (210 mL), sodium carbonate (5.6 g, 53 mmol), and water (105 mL) were added to a 500 mL three-necked flask and stirred at 80 °C for 4 hours. After stirring, the reaction solution was cooled to room temperature, and the organic layer was extracted with toluene. The extracted organic layer was washed with water and brine, and then concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to obtain 3',6'-difluoro-[1,1':4',1"-terphenyl]-2',5'-dicarboxynitrile (18.8 g, 59.6 mmol). The structure of the purified compound was then identified by ASAP / MS (Atmospheric Pressure Solid Analysis Probe Mass Spectrometry).

[0558] [Chemistry 125]

[0559] Under a nitrogen atmosphere, 12H-benzo[4,5]thieno[2,3-a]carbazole (2.87 g, 110.5 mmol) and DMF (30 mL) were added to a 200 mL flask. After cooling the flask to 0 °C, sodium hydride (0.44 g, 10.5 mmol) was added, and the mixture was stirred for 10 minutes. After stirring, 1.58 g (5.0 mmol) of 3',6'-difluoro-[1,1':4',1"-terphenyl]-2',5'-dicarboxynitrile was added to the flask, and the mixture was then heated to room temperature and stirred for 4 hours. After stirring, 10 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography, followed by resuscitation and washing with methanol and dimethoxyethane to obtain the target compound A1 (2.82 g, 3.43 mmol). The structure of compound A1 was then identified by LC / MS (Liquid Chromatography-Mass Spectrometry).

[0560] (Synthesis Example 2) The following describes the synthesis method of compound A2.

[0561] [Chemistry 126]

[0562] Under a nitrogen atmosphere, 12H-benzofluoro[2,3-a]carbazole (2.70 g, 10.5 mmol) and DMF (30 mL) were added to a 300 mL flask. After cooling the flask to 0 °C, sodium hydride (0.44 g, 10.5 mmol) was added, and the mixture was stirred for 10 minutes. Following stirring, 3',6'-difluoro-[1,1':4',1"-terphenyl]-2',5'-dicarboxynitrile (1.58 g, 5.0 mmol) was added to the flask, and the mixture was then heated to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography, followed by resuscitation and washing with methanol, dimethoxyethane, and toluene to obtain the target compound A2 (2.42 g, 3.06 mmol). The structure of compound A2 was identified by LC / MS.

[0563] (Synthesis Example 3) The following describes the synthesis method of compound A3.

[0564] [Chemistry 127]

[0565] Under a nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (2.87 g, 10.5 mmol) and DMF (52 mL) were added to a 300 mL flask. The flask was cooled to 0 °C, and sodium hydride (0.44 g, 10.5 mmol) was added, followed by stirring for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1"-terphenyl]-2',5'-dicarboxynitrile (1.58 g, 5.0 mmol) was added, and the mixture was heated to room temperature and stirred for 4 hours. After stirring, 40 mL of water was added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography, followed by resuscitation and washing with dimethoxyethane, ethyl acetate, and toluene to obtain the target compound A3 (4.02 g, 4.9 mmol). The structure of compound A3 was identified by LC / MS.

[0566] (Synthesis Example 4) The following describes the synthesis method of compound A4.

[0567] [Chemistry 128]

[0568] Under a nitrogen atmosphere, tetrafluoroterephthalonitrile (25 g, 125 mmol), 625 mL of 1,4-dioxane, and 400 mL of water were added to a 2000 mL three-necked flask. Next, 13 mL of 30% (w / w) ammonia solution was added, and the mixture was heated and stirred at 80 °C for 10 hours. After heating and stirring, the mixture was allowed to return to room temperature (25 °C). The solvent was removed by distillation using an evaporator, and the solid was purified by silica gel column chromatography to obtain 24 g of a white solid. Analysis of the white solid by GC-MS (Gas Chromatograph Mass Spectrum) identified it as compound M41 (yield 98%).

[0569] Under a nitrogen atmosphere, compound M41 (10 g, 51 mmol), iodine (26 g, 102 mmol), and 100 mL of acetonitrile were added to a 200 mL three-necked flask. Next, tert-butyl nitrite (t-BuONO) (10 g, 102 mmol) was added to the flask, and the mixture was stirred at 25 °C for 8 hours. After stirring, 50 mL of saturated sodium bisulfite aqueous solution was added to the reaction solution to extract the organic layer. The solvent was removed from the resulting solution by rotary evaporation, and the solid was purified by silica gel column chromatography to give 8.4 g of a white solid. GC-MS analysis of the white solid identified it as compound M42 (yield 54%).

[0570] [Chemistry 129]

[0571] Under a nitrogen atmosphere, compound M42 (8.4 g, 27 mmol), tributylphenyltin (10 g, 27 mmol), 90 mL of toluene, and Pd(PPh3)4 (1.6 g, 1.4 mmol) were added, and the mixture was heated under reflux with stirring for 8 hours.

[0572] After the reaction was complete, the reaction solution was purified by silica gel column chromatography to obtain 5.2 g of white solid. GC-MS analysis of the white solid identified it as compound M43 (yield 75%).

[0573] [Chemistry 130]

[0574] Under a nitrogen atmosphere, 12H-benzofuran[2,3-a]carbazole (1.74 g, 6.78 mmol), sodium hydride (0.27 g, 6.78 mmol), and 30 mL of DMF were added to a 200 mL three-necked flask, and the mixture was stirred at room temperature (25 °C) for 30 minutes. Next, compound M43 (0.5 g, 1.94 mmol) was added to the flask, and the mixture was stirred at 80 °C for 4 hours. Subsequently, the reaction mixture was added to 50 mL of saturated ammonium chloride aqueous solution, and the precipitated solid was purified by silica gel column chromatography to give 1.0 g of a yellow solid. Analysis of the yellow solid by ASAP-MS identified it as compound A4 (yield 55%). ASAP-MS is synonymous with ASAP / MS.

[0575] (Synthesis Example 5) The following describes the synthesis method of compound A5.

[0576] [Chemistry 131]

[0577] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (50 g, 184 mmol), trimethylchlorosilane (60 g, 552 mmol), and THF (200 mL) were added to a 1000 mL three-necked flask. After cooling the contents of the flask to -78 °C using a dry ice / acetone bath, 230 mL of diisopropylaminolithium (2 M, THF solution) was added dropwise. The mixture was stirred at -78 °C for 2 hours, then brought to room temperature and stirred for another 2 hours. After stirring, water (200 mL) was added to the flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed using a rotary evaporator under reduced pressure. The resulting intermediate a (73 g, 175 mmol, 95% yield) was used in the next reaction without purification. Trimethylchlorosilane is sometimes abbreviated as TMS-Cl. In the chemical formula of intermediate a, TMS stands for trimethylsilyl. LDA is short for Lithium Diisopropyl Amide.

[0578] Under a nitrogen atmosphere, intermediate a (73 g, 175 mmol) and dichloromethane (200 mL) were added to a 1000 mL pear-shaped flask. Iodine monochloride (85 g, 525 mmol) was dissolved in dichloromethane (200 mL) and added dropwise at 0 °C, followed by stirring at 40 °C for 4 hours. After stirring, the mixture was allowed to return to room temperature, and saturated sodium bisulfite aqueous solution (100 mL) was added. The organic layer was extracted with dichloromethane, washed with water and brine, and dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate b (65 g, 124 mmol, yield 71%).

[0579] Under a nitrogen atmosphere, intermediate b (22 g, 42 mmol), phenylboronic acid (12.8 g, 105 mmol), palladium acetate (0.47 g, 2.1 mmol), sodium carbonate (22 g, 210 mmol), and methanol (150 mL) were added to a 500 mL three-necked flask, and the mixture was stirred at 80 °C for 4 hours. After stirring, the reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and then concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate c (10 g, 24 mmol, yield 56%). The structure of the purified compound was identified by ASAP / MS (Atmospheric Pressure Solid Analysis Probe Mass Spectrometry).

[0580] Under a nitrogen atmosphere, intermediate c (10 g, 24 mmol), copper cyanide (10.6 g, 118 mmol), and DMF (15 mL) were added to a 200 mL three-necked flask, and the mixture was heated and stirred at 150 °C for 8 hours. After stirring, the mixture was cooled to room temperature, and then the reaction solution was injected into 10 mL of ammonia water. The organic layer was then extracted with dichloromethane, washed with water and brine, and dried over magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after solvent removal under reduced pressure was purified by silica gel column chromatography to give intermediate d (5.8 g, 18.34 mmol, yield 78%). DMF is an abbreviation for N,N-dimethylformamide.

[0581] Under a nitrogen atmosphere, intermediate d (1.0 g, 3.2 mmol), 12H-[1]benzothiophene[2,3-a]carbazole (1.9 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol), and 30 mL of DMF were added to a 100 mL three-necked flask, and the mixture was stirred at 120 °C for 6 hours. After stirring, the precipitated solid was filtered off and purified by silica gel column chromatography to obtain compound A5 (1.8 g, 2.2 mmol, yield 69%). The obtained compound was identified as compound A5 by ASAP-MS analysis.

[0582] (Synthesis Example 6) The following describes the synthesis method of compound A6.

[0583] [Chemistry 132]

[0584] Under a nitrogen atmosphere, intermediate b (30 g, 57 mmol), phenyl-d5-boronic acid (15.9 g, 125 mmol), palladium acetate (0.64 g, 2.9 mmol), sodium carbonate (27 g, 250 mmol), and methanol (150 mL) were added to a 500 mL three-necked flask, and the mixture was stirred at 80 °C for 6 hours. After stirring, the reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and then concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate e (12.6 g, 29 mmol, yield 51%). The structure of the purified compound was identified by ASAP / MS.

[0585] Under a nitrogen atmosphere, intermediate e (12.6 g, 29 mmol), copper cyanide (13 g, 145 mmol), and DMF (20 mL) were added to a 200 mL three-necked flask, and the mixture was heated and stirred at 150 °C for 8 hours. After stirring, the mixture was cooled to room temperature, and then the reaction solution was injected into 10 mL of ammonia water. The organic layer was then extracted with dichloromethane, washed with water and brine, and dried with magnesium sulfate. After drying, the solvent was removed by rotary evaporation under reduced pressure. The compound obtained after solvent removal under reduced pressure was purified by silica gel column chromatography to give intermediate f (6.2 g, 19.1 mmol, yield 66%).

[0586] Under a nitrogen atmosphere, intermediate f (1.5 g, 4.6 mmol), 12H-[1]benzothiophene[2,3-a]carbazole (2.8 g, 10.1 mmol), potassium carbonate (1.9 g, 13.8 mmol), and 30 mL of DMF were added to a 100 mL three-necked flask, and the mixture was stirred at 120 °C for 6 hours. After stirring, the precipitated solid was filtered off and purified by silica gel column chromatography to obtain compound A6 (3.2 g, 3.82 mmol, yield 83%). The obtained compound was identified as compound A6 by ASAP-MS analysis.

[0587] (Synthesis Example 7) The following describes the synthesis method of compound A7.

[0588] [Chemistry 133]

[0589] Under a nitrogen atmosphere, 4-bromodibenzothiophene (13.2 g, 50 mmol), 2-chloro-4,5-dimethylaniline (9.4 g, 60 mmol), tris(dibenzylacetone)dipalladium(0) (0.45 g, 0.5 mmol), tri-tert-butylphosphine tetrafluoroborate (0.58 g, 2.0 mmol), sodium tert-butoxide (7.2 g, 75 mmol), and 150 mL of toluene were added to a 300 mL three-necked flask. The mixture was heated and stirred at 60 °C for 4 hours. After stirring, the mixture was cooled to room temperature (25 °C). The reaction solution was purified by silica gel column chromatography to give intermediate g (15 g, 44.5 mmol, yield 89%). The purified compound was identified as intermediate g by GC-MS analysis.

[0590] Under a nitrogen atmosphere, intermediate g (15 g, 44.5 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.79 g, 1.78 mmol), palladium(II) acetate (0.2 g, 0.89 mmol), potassium carbonate (12.2 g, 89 mmol), and 120 mL of N,N-dimethylacetamide (DMAc) were added to a 300 mL three-necked flask and stirred at 130 °C for 7 hours. After stirring, the mixture was cooled to room temperature (25 °C). The reaction solution was purified by silica gel column chromatography to give intermediate h (12 g, 40.5 mmol, yield 91%). The purified compound was identified as intermediate h by GC-MS analysis.

[0591] Under a nitrogen atmosphere, intermediates d (1.0 g, 3.2 mmol), h (2.1 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol), and 30 mL of DMF were added to a 100 mL three-necked flask, and the mixture was stirred at 120 °C for 4 hours. The precipitated solid was filtered off and purified by silica gel column chromatography to give compound A7 (1.5 g, 1.7 mmol, yield 54%). The obtained compound was identified as compound A7 by ASAP-MS analysis.

[0592] (Synthesis Example 8) The following describes the synthesis method of compound A8.

[0593] [Chemistry 134]

[0594] Under a nitrogen atmosphere, 3-bromodibenzothiophene (26.3 g, 100 mmol), trimethylchlorosilane (33 g, 300 mmol), and THF (150 mL) were added to a 500 mL three-necked flask. The contents of the flask were cooled to -78 °C using a dry ice / acetone bath, and then 125 mL of diisopropylaminolithium (2 M, THF solution) was added dropwise. The mixture was stirred at -78 °C for 2 hours, then brought to room temperature and stirred for another 2 hours. After stirring, 100 mL of water was added to the flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed using a rotary evaporator under reduced pressure. 200 mL of dichloromethane was added to the resulting liquid, followed by the dropwise addition of iodine monochloride (49 g, 300 mmol) at 0 °C, and then stirred at 40 °C for 6 hours. After stirring, the mixture was allowed to return to room temperature. A saturated sodium bisulfite aqueous solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, and then dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate i (28 g, 72 mmol, yield 72%).

[0595] Under a nitrogen atmosphere, 4-bromodibenzothiophene (13.2 g, 50 mmol), copper oxide (I) (0.1 g, 0.66 mmol), ammonia (100 mL, 30%), and NMP (N-methylpyrrolidone) (100 mL) were added to a 500 mL three-necked flask and stirred at 80 °C for 12 hours. After stirring, the mixture was allowed to return to room temperature, and the organic layer was extracted with 100 mL of deion-exchanged water and diethyl ether. The extracted organic layer was washed with water and brine, and then dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate j (9.0 g, 45 mmol, 90% yield).

[0596] Under a nitrogen atmosphere, intermediates i (17.5 g, 45 mmol), j (9.0 g, 45 mmol), tris(dibenzylacetone)dipalladium(0) (0.8 g, 0.9 mmol), xantphos (4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene)) (1.0 g, 1.8 mmol), sodium tert-butoxide (6.5 g, 68 mmol), and 150 mL of toluene were added to a 300 mL three-necked flask. The mixture was heated and stirred at 100 °C for 8 hours, and then cooled to room temperature (25 °C). The reaction solution was purified by silica gel column chromatography to give intermediate k (9.5 g, 20.7 mmol, yield 46%). The purified compound was identified as intermediate k by GC-MS analysis.

[0597] Under a nitrogen atmosphere, intermediate K (9.5 g, 20.7 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.36 g, 0.82 mmol), palladium(II) acetate (0.093 g, 0.41 mmol), potassium carbonate (5.8 g, 42 mmol), and 60 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-necked flask. The mixture was stirred at 160 °C for 10 hours and then cooled to room temperature (25 °C). The precipitated solid was filtered off and washed with acetone to give intermediate L (6.9 g, 18.2 mmol, yield 88%). GC-MS analysis identified the washed compound as intermediate L.

[0598] Under a nitrogen atmosphere, intermediate d (1.0 g, 3.2 mmol), intermediate L (2.7 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol), and 30 mL of DMF were added to a 100 mL three-necked flask, and the mixture was stirred at 140 °C for 4 hours. After stirring, the precipitated solid was filtered off and purified by silica gel column chromatography to give compound A8 (2.3 g, 2.2 mmol, yield 69%). The obtained compound was identified as compound A8 by ASAP-MS analysis.

[0599] (Synthesis Example 9) The following describes the synthesis method of compound A9.

[0600] [Chemistry 135]

[0601] Under a nitrogen atmosphere, 2,4,6-trifluoro-1,1'-biphenyl (10 g, 48 mmol), trimethylchlorosilane (17 g, 144 mmol), and THF (50 mL) were added to a 200 mL three-necked flask. The contents of the flask were cooled to -78 °C using a dry ice / acetone bath, and then 60 mL of diisopropylaminolithium (2 M, THF solution) was added dropwise. The mixture was stirred at -78 °C for 2 hours, then brought to room temperature and stirred for another 2 hours. After stirring, 50 mL of water was added to the flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure. The resulting intermediate n (15 g, 44 mmol, 92% yield) was used in the next reaction without purification. Trimethylchlorosilane is sometimes abbreviated as TMS-Cl. In the chemical formula of intermediate n, TMS stands for trimethylsilyl. LDA is short for Lithium Diisopropyl Amide.

[0602] Under a nitrogen atmosphere, intermediate n (15 g, 44 mmol) and dichloromethane (100 mL) were added to a 500 mL flask. Iodine monochloride (21 g, 132 mmol) was dissolved in dichloromethane (200 mL) and added dropwise at 0 °C, followed by stirring at 40 °C for 4 hours. After stirring, the mixture was allowed to return to room temperature, and saturated sodium bisulfite aqueous solution (100 mL) was added. The organic layer was extracted with dichloromethane, washed with water and brine, and dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate o (10 g, 121 mmol, yield 48%).

[0603] Under a nitrogen atmosphere, intermediate O (10 g, 21 mmol), copper cyanide (4.1 g, 46 mmol), and NMP (N-methyl-2-pyrrolidone) (45 mL) were added to a 200 mL three-necked flask, and the mixture was heated and stirred at 150 °C for 8 hours. After stirring, the mixture was cooled to room temperature, and the reaction solution was injected into 30 mL of ammonia water. The organic layer was then extracted with dichloromethane, washed with water and brine, and dried over magnesium sulfate. After drying, the solvent was removed by rotary evaporation under reduced pressure. The compound obtained after solvent removal under reduced pressure was purified by silica gel column chromatography to give intermediate P (1.8 g, 7.1 mmol, yield 34%).

[0604] Under a nitrogen atmosphere, 12H-[1]benzothiophene[2,3-a]carbazole (3.0 g, 11 mmol) and DMF (20 mL) were added to a 100 mL flask. After cooling the flask to 0 °C, sodium hydride (0.44 g, 11 mmol) was added and stirred for 30 minutes. After stirring, intermediate p (0.8 g, 3.2 mmol) was added to the flask, and the temperature was raised to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography to obtain compound A9 (1.6 g, 1.60 mmol, yield 50%). The obtained compound was identified as compound A9 by ASAP-MS analysis.

[0605] (Synthesis Example 10) The following describes the synthesis method of compound A10.

[0606] [Chemistry 136]

[0607] Under a nitrogen atmosphere, 4,5-difluorophthalonitrile (10 g, 61 mmol), bromobenzene (38 g, 244 mmol), potassium carbonate (13 g, 91 mmol), palladium acetate (0.4 g, 1.8 mmol), tricyclohexylphosphine (0.4 g, 1.8 mmol), palladium acetate (0.4 g, 1.8 mmol), 2-ethylhexanoic acid (2 ml, 12.2 mmol), and 120 ml xylene were added to a 300 ml three-necked flask and stirred at 150 °C for 10 hours. After stirring, the reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and concentrated using a rotary evaporator. The concentrated compound was purified by silica gel column chromatography to give intermediate m (7.2 g, 23 mmol, yield 37%). Furthermore, the structure of the purified compound was identified as intermediate m by ASAP / MS. ASAP / MS is short for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry. P(Cy)3 is short for tricyclohexylphosphine.

[0608] Under a nitrogen atmosphere, 12H-[1]benzothiophene[2,3-a]carbazole (3.0 g, 11 mmol) and DMF (20 mL) were added to a 100 mL flask. After cooling the flask to 0 °C, sodium hydride (0.44 g, 11 mmol) was added and stirred for 30 minutes. After stirring, intermediate m (1.4 g, 4.4 mmol) was added to the flask, and the temperature was raised to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography to obtain compound A10 (2.6 g, 3.16 mmol, yield 71%). The obtained compound was identified as compound A10 by ASAP-MS analysis.

[0609] (Comparative Synthesis Example 1) The following describes the synthesis method of the comparative compound Ref-1.

[0610] [Chemistry 137]

[0611] Under a nitrogen atmosphere, 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole (2.97 g, 10.5 mmol) and DMF (30 mL) were added to a 300 mL flask. The flask was cooled to 0 °C, and sodium hydride (0.44 g, 10.5 mmol) was added, followed by stirring for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1"-terphenyl]-2',5'-dicarboxynitrile (1.58 g, 5.0 mmol) was added, and the mixture was heated to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography, followed by resuspending and washing with dimethoxyethane to obtain the target comparative compound Ref-1 (3.9 g, 4.6 mmol). The structure of compound Ref-1 was identified by LC / MS.

[0612] (Comparative Synthesis Example 2) The following describes the synthesis of the comparative compound Ref-2.

[0613] [Chemistry 138]

[0614] Under a nitrogen atmosphere, 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole (2.00 g, 7.1 mmol) and DMF (20 mL) were added to a 200 mL flask. The flask was cooled to 0 °C, and sodium hydride (0.28 g, 7.1 mmol) was added, followed by stirring for 30 minutes. After stirring, intermediate d (1.00 g, 3.2 mmol) was added to the flask, and the mixture was then heated to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the solid was recovered by filtration. The recovered solid was purified by silica gel column chromatography to give the comparative compound Ref-2 (0.9 g, 1.00 mmol, yield 34%). The compound was identified as Ref-2 by ASAP-MS analysis.

[0615] Explanation of reference numerals in the attached figures 1 Organic EL element 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. A compound, characterized in that, Represented by the following general formula (1), [Chemistry 1] In the general formula (1), D is a group represented by the following general formula (11), general formula (12) or general formula (13), Wherein, at least one D is a group represented by the following general formula (12) or general formula (13), m is 1, 2, or 3. When m is 2 or 3, multiple Ds may be the same or different from each other. R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heteroaryl groups with 5–14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms substituted or unsubstituted arylsilyl groups having 3 to 6 carbon atoms 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 alkylamino groups with 2 to 12 carbon atoms 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. In this case, at least one R is a substituent. At least one R, acting as a substituent, is bonded to the benzene ring in the general formula (1) via a carbon-carbon bond. n is 1, 2, or 3. When n is 2 or 3, multiple R's can be the same or different from each other. The sum of the number of R substituents and the number of groups represented by the following general formula (12) or general formula (13) is 3 or 4. [Chemistry 2] [Chemistry 3] [Chemistry 4] In the general formula (11), R1 to R8 are each independently a hydrogen atom, a halogen atom, or a substituent. R in the general formula (12) 11 ~R 18 Each can be independently a hydrogen atom, a halogen 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 A ring is formed by bonding together any one or more groups within a group. R in the general formula (13) 111 ~R 118 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 111 and R 112 group, R 112 and R 113 group, R 113 and R 114 group, R 115 and R 116 group, R 116 and R 117 The group, and R 117 and R 118 A ring is formed by bonding together any one or more groups within a group. R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, 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 cycloalkyl groups with 3 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, 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, 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, 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. In the general formulas (12) and (13), A, B, and C are each independently selected from the group of ring structures represented by the following general formulas (14), (15), and (16). The ring structure A, ring structure B, and ring structure C can be condensed with the adjacent ring structure at any position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, multiple ring structures A may be the same or different from each other. When px is 2, 3, or 4, multiple ring structures B may be the same or different from each other. When py is 2, 3, or 4, multiple ring structures C may be the same or different from each other. Wherein, at least one D is p, which is 2, 3, or 4 and contains a group represented by said general formula (12) as ring structure A, selected from the group consisting of ring structures represented by general formulas (15) and (16) below; or at least one of px and py is 2, 3, or 4 and contains a group represented by said general formula (13) as ring structure B or ring structure C, selected from the group consisting of ring structures represented by general formulas (15) and (16) below. In the general formulas (11) to (13), * indicates the position where it is bonded to the benzene ring in the general formula (1). [Chemistry 5] In the general formula (14), R 19 and R 20 Each can be independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups bond together to form a ring. In the general formulas (15) and (16), X1 and X2 are NR independently. 120 sulfur atoms or oxygen atoms R 120 It can be a hydrogen atom, a halogen atom, or a substituent. R as a substituent 19 R 20 and R 120 They are each independently synonymous with R1 to R8, which are substituents.

2. The compound according to claim 1, characterized in that, The sum of the number of R substituents and the number of groups represented by the general formula (12) or general formula (13) is 4.

3. The compound according to claim 1 or 2, characterized in that, Compounds represented by the general formula (1) are represented by the following general formulas (110), (120), or (130). [Chemistry 6] In the general formulas (110), (120) and (130), D, m, R and n are synonyms with D, m, R and n in the general formula (1), respectively.

4. The compound according to any one of claims 1 to 3, characterized in that, The compound represented by the general formula (1) is any compound selected from the group consisting of compounds represented by the following general formulas (111) to (118). [Chemistry 7] In the general formulas (111) and (112), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 8] In the general formulas (113) to (116), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122 At least one of them is a substituent, and R is a substituent. 121 and R 122 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 9] In the general formulas (117) and (118), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 It is synonymous with R as a substituent in the general formula (1).

5. The compound according to any one of claims 1 to 3, characterized in that, The compound represented by the general formula (1) is any compound selected from the group consisting of compounds represented by the following general formulas (121) to (129). [Chemistry 10] In the general formulas (121) to (123), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 11] In the general formulas (124) to (126), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122 At least one of them is a substituent, and R is a substituent. 121 and R 122 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 12] In the general formulas (127) to (129), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 It is synonymous with R as a substituent in the general formula (1).

6. The compound according to any one of claims 1 to 3, characterized in that, The compound represented by the general formula (1) is any compound selected from the group consisting of compounds represented by the following general formulas (131) to (135). [Chemistry 13] In the general formula (131), D 11 It is a group represented by the general formula (12) or general formula (13). R 121 ~R 123 Each is independently synonymous with R in the general formula (1), wherein R 121 ~R 123 At least one of them is a substituent, and R is a substituent. 121 ~R 123 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 14] In the general formulas (132) to (134), D 11 and D 12 Each is independently synonymous with D in the general formula (1), where D 11 and D 12 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 and R 122 Each is independently synonymous with R in the general formula (1), wherein R 121 and R 122 At least one of them is a substituent, and R is a substituent. 121 and R 122 The R in the general formula (1) is synonymous with the substituent R. [Chemistry 15] In the general formula (135), D 11 ~D 13 Each is independently synonymous with D in the general formula (1), where D 11 ~D 13 At least one of them is a group represented by the general formula (12) or general formula (13), R 121 As a substituent, R as a substituent 121 It is synonymous with R as a substituent in the general formula (1).

7. The compound according to any one of claims 1 to 6, characterized in that, R in the general formula (12) 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. R in the general formula (13) 111 and R 112 group, R 112 and R 113 group, R 113 and R 114 group, R 115 and R 116 group, R 116 and R 117 The group, and R 117 and R 118 The groups are not mutually bonded.

8. The compound according to any one of claims 1 to 7, characterized in that, It has at least one group represented by the general formula (12).

9. The compound according to any one of claims 1 to 8, characterized in that, The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the following general formulas (12A), (12B), (12C), (12D), (12E) and (12F). [Chemistry 16] [Chemistry 17] [Chemistry 18] [Chemistry 19] [Chemistry 20] [Chemistry 21] In the general formulas (12A), (12B), (12C), (12D), (12E), and (12F), R 11 ~R 18 Independently related to R in the general formula (12) 11 ~R 18 Synonyms R 19 and R 20 Independently related to R in the general formula (14) 19 and R 20 Synonyms X1 is synonymous with X1 in the general formula (15). The asterisk (*) in the general formulas (12A), (12B), (12C), (12D), (12E), and (12F) indicates the position where the benzene ring in the general formula (1) is bonded.

10. The compound according to claim 9, characterized in that, The group represented by the general formula (12) is any group selected from the group consisting of the groups represented by the general formulas (12A), (12D) and (12F).

11. The compound according to any one of claims 1 to 10, characterized in that, X1 is an oxygen atom or a sulfur atom.

12. The compound according to any one of claims 1 to 11, characterized in that, R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having a cyclic carbon number of 3 to 30.

13. The compound according to any one of claims 1 to 12, characterized in that, R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having 3 to 6 carbon atoms.

14. The compound according to any one of claims 1 to 11, characterized in that, R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted heterocyclic groups with 5 to 30 cyclic atoms Unsubstituted alkyl groups having 1 to 30 carbon atoms Unsubstituted cycloalkyl groups with 3 to 30 carbon atoms Unsubstituted alkylsilyl groups with 3 to 30 carbon atoms Unsubstituted arylsilyl groups with 6 to 60 carbon atoms, Unsubstituted alkoxy groups with 1 to 30 carbon atoms Unsubstituted aryloxy groups with 6–30 carbon atoms in the cyclic ring, Unsubstituted alkylamino groups with 2 to 30 carbon atoms Unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic ring, Unsubstituted alkylthio groups with 1 to 30 carbon atoms, or Unsubstituted arylthio groups with 6 to 30 cyclic carbons.

15. The compound according to any one of claims 1 to 11, characterized in that, R1 to R8 as substituents, R as substituents 11 ~R 18 And R as a substituent 111 ~R 118 Each independently, Unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group, Unsubstituted alkyl groups having 1 to 30 carbon atoms, or Unsubstituted cycloalkyl groups with 3 to 30 carbon atoms.

16. The compound according to any one of claims 1 to 15, characterized in that, R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, substituted or unsubstituted aryl groups with 6 to 14 carbon atoms Substituted or unsubstituted heteroaryl groups with 5–14 cyclic atoms Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having 3 to 6 carbon atoms.

17. The compound according to any one of claims 1 to 15, characterized in that, R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heteroaryl groups with 5–14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Unsubstituted alkylsilyl groups with 3 to 6 carbon atoms Unsubstituted arylsilyl groups with 3 to 6 carbon atoms, Unsubstituted alkoxy groups with 1 to 6 carbon atoms, Unsubstituted aryloxy groups with 6–14 cyclic carbon atoms, Unsubstituted alkylamino groups with 2 to 12 carbon atoms, Unsubstituted alkylthio groups with 1 to 6 carbon atoms, or Unsubstituted arylthio groups with 6 to 14 cyclic carbons.

18. The compound according to any one of claims 1 to 15, characterized in that, R can be a hydrogen atom, a halogen atom, or a substituent, respectively. R, as a substituent, is independently, Unsubstituted aryl groups with 6–14 cyclic carbons Unsubstituted heteroaryl groups with 5–14 cyclic atoms Unsubstituted alkyl groups having 1 to 6 carbon atoms, or Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms.

19. A material for use in organic electroluminescent devices, characterized in that, Contains the compound according to any one of claims 1 to 18.

20. An organic electroluminescent element, characterized in that, It has an anode, a cathode, and an organic layer. The organic layer comprises a compound as a first compound according to any one of claims 1 to 18.

21. The organic electroluminescent element as described in claim 20, characterized in that, The organic layer has at least one light-emitting layer. The light-emitting layer contains the first compound.

22. An electronic device, characterized in that, It is equipped with the organic electroluminescent element as described in claim 20 or 21.

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