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

Abstract

To provide a compound having a high PLQY.SOLUTION: Provided is a compound represented by the general formula (1) below, wherein D is a group represented by the general formula (11) below or the like, m is 1, 2, or 3, where when m is 2 or 3, a plurality of D are mutually the same or different, R is each independently a hydrogen atom, a halogen atom, or a substituent, and n is 1, 2, or 3, where when n is 2 or 3, a plurality of R are mutually the same or different.SELECTED DRAWING: Figure 3

Description

[Technical field]

[0001] The present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device. [Background technology]

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic electroluminescence (EL) elements that use light emitted from singlet excitons are being applied to full-color displays of mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, research is being conducted to improve the performance of organic EL elements.

[0003] For example, it is expected that organic EL elements can emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. In this context, highly efficient fluorescent organic EL elements using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being studied. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon that reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors" edited by Adachi Chinaya, Kodansha, published April 1, 2012, pp. 261-268. Known examples of compounds exhibiting thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF compounds) include compounds in which a donor moiety and an acceptor moiety are bound in the molecule.

[0004] Examples of documents relating to organic EL devices and compounds used in organic EL devices include Patent Documents 1, 2, 3, 4, and 5. [Prior art documents] [Patent documents]

[0005] [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 [Problem to be solved by the invention]

[0006] In order to improve the performance of electronic devices such as displays, there is a demand for further improvement in the performance of organic EL elements. The performance of an organic EL element includes luminous efficiency. A factor for improving the luminous efficiency is to use a compound with a high photoluminescence quantum yield (PLQY). Another performance of an organic EL element is low driving voltage.

[0007] The present invention aims to provide a compound with a high PLQY. Another object of the present invention is to provide a material for an organic electroluminescence device containing a compound with a high PLQY, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device. Another object of the present invention is to provide a high-performance organic EL device, and to provide an electronic device equipped with the organic electroluminescence device. [Means for solving the problem]

[0008] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1):

[0009] [ka]

[0010] (In the general formula (1), D is a group represented by the following general formula (11), general formula (12), or general formula (13), However, 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, D's are the same or different, R is each independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms; a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms, With the proviso that at least one R is a substituent, At least one R 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, R's are the same or different, 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.

[0011] [ka]

[0012] [ka]

[0013] [ka]

[0014] (R1 to R8 in the general formula (11) each independently represents a hydrogen atom, a halogen atom, or a substituent, R in the general formula (12) 11 ~R 18 are each 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 16and R 17 and R 17 and R 18 any one or more of the pairs of R in the general formula (13) 111 ~R 118 are each 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 and R 117 and R 118 any one or more of the pairs of R1 to R8 as substituents, R as substituents 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, In the general formula (12) and the general formula (13), A, B, and C each independently represent a ring structure selected from the group consisting of ring structures represented by the following general formula (14), general formula (15), and general formula (16), The ring structure A, the ring structure B, and the ring structure C are 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, the ring structures A are the same or different from each other, When px is 2, 3 or 4, the ring structures B are the same or different from each other, When py is 2, 3 or 4, the ring structures C are the same or different from each other, provided that at least one D is a group represented by the general formula (12) in which p is 2, 3, or 4 and which contains, as the ring structure A, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), or a group represented by the general formula (13) in which at least one of px and py is 2, 3, or 4 and which contains, as the ring structure B or ring structure C, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), In the general formulae (11) to (13), * indicates the bonding position to the benzene ring in the general formula (1).

[0015] [ka]

[0016] (In the general formula (14), R 19 and R 20 are each independently a hydrogen atom, a halogen atom or a substituent, or R 19 and R 20 are bonded to each other to form a ring, In the general formula (15) and the general formula (16), X1 and X2 each independently represent NR120 , a sulfur atom, or an oxygen atom; R 120 is a hydrogen atom, a halogen atom or a substitution, R as a Substituent 19 , R 20 and R 120 each independently has the same meaning as R1 to R8 as the substituent.)

[0017] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which contains the compound according to the above-mentioned aspect of the present invention.

[0018] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an organic layer, the organic layer containing the compound according to the aspect of the present invention as a first compound.

[0019] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention.

[0020] According to one aspect of the present invention, a compound having a high PLQY can be provided. According to another aspect of the present invention, a material for an organic electroluminescence device or an organic electroluminescence device containing a compound having a high PLQY can be provided. According to another aspect of the present invention, an electronic device equipped with the organic electroluminescence device can be provided. According to another aspect of the present invention, a high-performance organic EL device can be provided, and an electronic device equipped with the organic electroluminescence device can also be provided. [Brief description of the drawings]

[0021] [Figure 1] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Diagram 2] FIG. 13 is a diagram showing an example of an attenuation curve of a transient PL. [Diagram 3] FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 4] FIG. 11 is a diagram showing the energy levels of a first compound and a second compound in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship of energy transfer. [Diagram 5] FIG. 13 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an emitting layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention, and the relationship between energy transfer. [Figure 6] FIG. 13 is a diagram showing the energy levels of a first compound and a third compound in an emitting layer of an example of an organic electroluminescence element according to a fifth embodiment of the present invention, and a relationship between energy transfer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] First Embodiment (compound) The compound according to this embodiment is a compound represented by the following general formula (1).

[0023] [ka]

[0024] (In the general formula (1), D is a group represented by the following general formula (11), general formula (12), or general formula (13), However, 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, D's are the same or different, R is each independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms; a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms, With the proviso that at least one R is a substituent, At least one R 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, R's are the same or different, 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.

[0025] [ka]

[0026] [ka]

[0027] [ka]

[0028] (R1 to R8 in the general formula (11) each independently represents a hydrogen atom, a halogen atom, or a substituent, R in the general formula (12) 11 ~R18 are each 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 and R 17 and R 18 any one or more of the pairs of R in the general formula (13) 111 ~R 118 are each 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 and R 117 and R 118 any one or more of the pairs of R1 to R8 as substituents, R as substituents 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, In the general formula (12) and the general formula (13), A, B, and C each independently represent a ring structure selected from the group consisting of ring structures represented by the following general formula (14), general formula (15), and general formula (16), The ring structure A, the ring structure B, and the ring structure C are 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, the ring structures A are the same or different from each other, When px is 2, 3 or 4, the ring structures B are the same or different from each other, When py is 2, 3 or 4, the ring structures C are the same or different from each other, provided that at least one D is a group represented by the general formula (12) in which p is 2, 3, or 4 and which contains, as the ring structure A, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), or a group represented by the general formula (13) in which at least one of px and py is 2, 3, or 4 and which contains, as the ring structure B or ring structure C, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), In the general formulae (11) to (13), * indicates the bonding position to the benzene ring in the general formula (1).

[0029] [ka]

[0030] (In the general formula (14), R 19 and R 20 are each independently a hydrogen atom, a halogen atom or a substituent, or R 19 and R 20 are bonded to each other to form a ring, In the general formula (15) and the general formula (16), X1 and X2 each independently represent NR 120 , a sulfur atom, or an oxygen atom; R 120 is a hydrogen atom, a halogen atom or a substitution, R as a Substituent 19 , R 20 and R 120 each independently has the same meaning as R1 to R8 as the substituent.)

[0031] The compound according to this embodiment has a group D A Or group D B has at least one Base D A is a group represented by the general formula (12) in which p is 2, 3 or 4 and which contains, as the ring structure A, any ring structure selected from the group consisting of the ring structures represented by the general formulae (15) and (16). Group D A It is preferable that p is 2, 3 or 4, and the ring structure A contains a ring structure represented by the general formula (14) and a ring structure represented by the general formula (15). Base D B is a group represented by the general formula (13) in which at least one of px and py is 2, 3, or 4, and which contains, as the ring structure B or the ring structure C, any ring structure selected from the group consisting of the ring structures represented by the general formulae (15) and (16). Group D B It is preferable that at least one of px and py is 2, 3, or 4, and the ring structure B or the ring structure C includes a ring structure represented by the general formula (14) and a ring structure represented by the general formula (15). Furthermore, in the compound according to this embodiment, the number N of the substituents RR And, group D A Or group D B Number of N D The sum of (N R +N D ) is 3 or 4.

[0032] The phrase "R as a substituent is bonded to the benzene ring in the general formula (1) through a carbon-carbon bond" means that a carbon atom among elements contained in R as a substituent is directly bonded to any one of six carbon atoms constituting the benzene ring in the general formula (1).

[0033] In the compound according to this embodiment, the sum of the number of R substituents and the number of groups represented by the general formula (12) or (13) is preferably 4.

[0034] In the compound according to this embodiment, the number N of the substituent R R And, group D A Or group D B Number of N D The sum of (N R +N D ) is preferably 4.

[0035] The compound represented by the general formula (1) is also preferably a compound represented by the following general formula (110), general formula (120) or general formula (130).

[0036] [ka]

[0037] (In the general formula (110), general formula (120), and general formula (130), D, m, R, and n are respectively defined as D, m, R, and n in the general formula (1).)

[0038] The compound represented by the general formula (1) is also preferably any compound selected from the group consisting of compounds represented by the following general formulae (111) to (118).

[0039] [ka]

[0040] (In the general formulae (111) and (112), D 11 is a group represented by the general formula (12) or general formula (13), R 121 ~R 123 are each independently defined as R in the general formula (1), provided that R 121 ~R 123 At least one of the substituents is a substituent, and R 121 ~R 123 has the same meaning as R as the substituent in the general formula (1).

[0041] [ka]

[0042] (In the general formulae (113) to (116), D 11 and D. 12 Each independently has the same meaning as D in the general formula (1), provided that D 11 and D. 12 At least one of the above is a group represented by general formula (12) or general formula (13), R 121 and R 122 are each independently defined as R in the general formula (1), provided that R 121 and R 122 At least one of the substituents is a substituent, and R 121 and R 122 has the same meaning as R as the substituent in the general formula (1).

[0043] [ka]

[0044] (In the general formulae (117) and (118), D 11 ~D 13 Each independently has the same meaning as D in the general formula (1), provided that D 11 ~D 13 At least one of the above is a group represented by general formula (12) or general formula (13), R 121 is a substituent, and R as a substituent 121 has the same meaning as R as the substituent in the general formula (1).

[0045] The compound represented by the general formula (1) is also preferably any compound selected from the group consisting of compounds represented by the following general formulae (121) to (129).

[0046] [ka]

[0047] (In the general formulae (121) to (123), D 11 is a group represented by the general formula (12) or general formula (13), R 121 ~R 123 are each independently defined as R in the general formula (1), provided that R 121 ~R 123 At least one of the substituents is a substituent, and R 121 ~R 123 has the same meaning as R as the substituent in the general formula (1).

[0048] [ka]

[0049] (In the general formulae (124) to (126), D 11 and D. 12Each independently has the same meaning as D in the general formula (1), provided that D 11 and D. 12 At least one of the above is a group represented by general formula (12) or general formula (13), R 121 and R 122 are each independently defined as R in the general formula (1), provided that R 121 and R 122 At least one of the substituents is a substituent, and R 121 and R 122 has the same meaning as R as the substituent in the general formula (1).

[0050] [ka]

[0051] (In the general formulae (127) to (129), D 11 ~D 13 Each independently has the same meaning as D in the general formula (1), provided that D 11 ~D 13 At least one of the above is a group represented by general formula (12) or general formula (13), R 121 is a substituent, and R as a substituent 121 has the same meaning as R as the substituent in the general formula (1).

[0052] The compound represented by the general formula (1) is also preferably any compound selected from the group consisting of compounds represented by the following general formulae (131) to (135).

[0053] [ka]

[0054] (In the general formula (131), D 11is a group represented by the general formula (12) or general formula (13), R 121 ~R 123 are each independently defined as R in the general formula (1), provided that R 121 ~R 123 At least one of the substituents is a substituent, and R 121 ~R 123 has the same meaning as R as the substituent in the general formula (1).

[0055] [ka]

[0056] (In the general formulae (132) to (134), D 11 and D. 12 Each independently has the same meaning as D in the general formula (1), provided that D 11 and D. 12 At least one of the above is a group represented by general formula (12) or general formula (13), R 121 and R 122 are each independently defined as R in the general formula (1), provided that R 121 and R 122 At least one of the substituents is a substituent, and R 121 and R 122 has the same meaning as R as the substituent in the general formula (1).

[0057] [ka]

[0058] (In the general formula (135), D 11 ~D 13 Each independently has the same meaning as D in the general formula (1), provided that D 11 ~D 13At least one of the above is a group represented by general formula (12) or general formula (13), R 121 is a substituent, and R as a substituent 121 has the same meaning as R as the substituent in the general formula (1).

[0059] 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 and R 17 and R 18 None of the pairs are 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 and R 117 and R 118 It is preferred that none of the pairs are bonded to each other.

[0060] In the general formula (14), R 19 and R 20 It is preferred that the pairs are not bonded to each other.

[0061] The compound according to this embodiment preferably has at least one group represented by the general formula (12).

[0062] In the general formula (12), p is preferably 2, 3 or 4. In the general formula (13), px and py are preferably each independently 2, 3 or 4.

[0063] The compound according to this embodiment is a compound represented by the general formula (1), in which p is 2, 3 or 4 as D, and the ring structure A is a group D represented by the general formula (12) containing any one of the ring structures selected from the group consisting of the ring structures represented by the general formulas (15) and (16). A It is preferable to have at least one of the following:

[0064] In the compound according to this embodiment, it is preferable that the ring structure A, the ring structure B, and the ring structure C are each independently any ring structure selected from the group consisting of the ring structures represented by the general formula (14) and the general formula (15).

[0065] In the compound according to this embodiment, the group represented by the general formula (12) is preferably any one group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E) and (12F).

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R 11 ~R 18 each independently represents R in the general formula (12) 11 ~R 18 is synonymous with R 19 and R 20 each independently represents R in the general formula (14). 19 and R 20 is synonymous with X1 has the same meaning as X1 in general formula (15), In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), * indicates the bonding position to the benzene ring in the general formula (1).

[0073] R in the general formulae (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 and R 19 and R 20 It is preferred that none of the pairs are bonded to each other.

[0074] In the compound according to 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 formulae (12A), (12D) and (12F).

[0075] In the compound according to this embodiment, X1 is preferably an oxygen atom or a sulfur atom.

[0076] In the compound according to this embodiment, the group D A is preferably any group selected from the group consisting of groups represented by general formulas (12A), (12B), (12C), (12D), (12E) and (12F).

[0077] The compound according to this embodiment preferably has, as D in the general formula (1), at least one group selected from the group consisting of groups represented by the general formulae (12A), (12B), (12C), (12D), (12E) and (12F). It is more preferable that the compound according to this embodiment has at least one group in which D in the general formula (1) is any group selected from the group consisting of groups represented by the general formulas (12A), (12B), (12C), (12D), (12E) and (12F), and X1 is an oxygen atom or a sulfur atom.

[0078] It is preferable that D in the general formula (110), the general formula (120), and the general formula (130) each independently represents any one group selected from the group consisting of the groups represented by the general formulae (12A), (12B), (12C), (12D), (12E), and (12F).

[0079] D in the general formulae (111) to (118), (121) to (129), and (131) to (135) 11 , D 12 and D. 13 are preferably each independently any group selected from the group consisting of groups represented by general formulas (12A), (12B), (12C), (12D), (12E) and (12F).

[0080] In the compound according to this embodiment, R1 to R8 as substituents, R 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; It is preferable.

[0081] In the compound according to this embodiment, R1 to R8 as substituents, R 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms is preferred.

[0082] In the compound according to this embodiment, R1 to R8 as substituents, R 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or An unsubstituted arylthio group having 6 to 30 ring carbon atoms is preferred.

[0083] In the compound according to this embodiment, R1 to R8 as substituents, R 11 ~R 18 , and R as a substituent 111 ~R 118 are each independently an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or An unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms is preferred.

[0084] In the compound according to this embodiment, R1 to R8, R 11 ~R 18 , and R 111 ~R 118 is also preferably a hydrogen atom.

[0085] In the compound according to this embodiment, each R is independently a hydrogen atom, a halogen atom, or a substituent. Each R as a substituent is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms is preferred.

[0086] In the compound according to this embodiment, each R is independently a hydrogen atom, a halogen atom, or a substituent. Each R as a substituent is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heteroaryl group having 5 to 14 ring atoms; an unsubstituted alkyl group having 1 to 6 carbon atoms; an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; an unsubstituted alkylsilyl group having 3 to 6 carbon atoms; an unsubstituted arylsilyl group having 3 to 6 carbon atoms; an unsubstituted alkoxy group having 1 to 6 carbon atoms; an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or An unsubstituted arylthio group having 6 to 14 ring carbon atoms is preferred.

[0087] In the compound according to this embodiment, each R is independently a hydrogen atom, a halogen atom, or a substituent. Each R as a substituent is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heteroaryl group having 5 to 14 ring atoms; an unsubstituted alkyl group having 1 to 6 carbon atoms, or An unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms is preferred.

[0088] The compound according to this embodiment is preferably a delayed fluorescent compound.

[0089] Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if it is possible to reduce the energy transfer rate, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, Figure 10.38 in the document explains the mechanism of delayed fluorescence generation. The compound according to this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0090] In general, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0091] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a method of exciting a sample with a pulsed laser and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF materials is classified into emission components from singlet excitons generated during the first PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long life span. Thus, there is a large time difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, it is possible to obtain the emission intensity derived from delayed fluorescence.

[0092] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 1. An example of a method for measuring transient PL using Figure 1 and an analysis of the behavior of delayed fluorescence will be described.

[0093] 1 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG.

[0094] The sample accommodated in the sample chamber 102 is obtained by forming a thin film, in which a doping material is doped at a concentration of 12 mass % relative to a matrix material, on a quartz substrate.

[0095] A pulsed laser is irradiated from a pulsed laser unit 101 to a thin film sample accommodated in a sample chamber 102 to excite the doping material. Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103 to form a two-dimensional image in a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. By cutting out this two-dimensional image at a predetermined time axis, an emission spectrum can be obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cutting out the two-dimensional image at the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.

[0096] For example, the following reference compound H1 was used as the matrix material, and the following reference compound D1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurement was performed.

[0097] [ka]

[0098] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following reference compound H2 as a matrix material and the above-mentioned reference compound D1 as a doping material.

[0099] FIG. 2 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0100] [ka]

[0101] As described above, the transient PL measurement can provide an emission decay curve with the emission intensity on the vertical axis and the time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence that decays slowly to the intensity of the fluorescence that decays quickly is somewhat large.

[0102] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0103] The amount and ratio of prompt luminescence and delayed luminescence can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG.

[0104] In addition, a sample prepared by the following method is used to measure the delayed fluorescence of the compound according to this embodiment. For example, the compound according to this embodiment is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. In addition, in order to prevent quenching due to oxygen, the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. The total fluorescence quantum yield is calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0105] The amount and ratio of prompt luminescence and delayed luminescence can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the compound to be measured is X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratios of prompt luminescence and delayed luminescence of compounds other than the compounds according to this embodiment in this specification are measured in the same manner as the amounts and ratios of prompt luminescence and delayed luminescence of the compounds according to this embodiment.

[0106] ΔST In this embodiment, the lowest excited singlet energy S1 and the energy gap T at 77 [K] 77K Difference between (S1-T 77K ) is defined as ΔST.

[0107] The lowest excited singlet energy S1 (M1) of the compound according to this embodiment and the energy gap T at 77 [K] of the compound according to this embodiment 77K The difference ΔST(M1) from (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 relationship of the following formula (10), (11), (12), or (13). ΔST(M1)=S1(M1)-T 77K (M1)<0.3eV …(number 10) ΔST(M1)=S1(M1)-T 77K (M1)<0.2 eV …(Equation 11) ΔST(M1)=S1(M1)-T 77K (M1)<0.1eV …(Equation 12) ΔST(M1)=S1(M1)-T 77K (M1)<0.01eV…(Equation 13)

[0108] Relationship between triplet energy and energy gap at 77[K] Here, a relationship between the triplet energy and the energy gap at 77 [K] will be described. In this embodiment, the energy gap at 77 [K] is different from the triplet energy that is usually defined. The triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent and the horizontal axis. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state are mixed. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the light emission is from, but it is basically considered that the triplet energy value is dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish the difference in the strict sense, the value measured as follows is referred to as the energy gap T 77KThe compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent and the horizontal axis is determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let us assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0109] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using a spectrofluorometer body, model F-4500, manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0110] Lowest excited singlet energy S1 The method for measuring the lowest excited singlet energy S1 using a solution (sometimes referred to as a solution method) includes the following method. Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell, then measure the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) at room temperature (300 K). Draw a tangent to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0111] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0112] Method for producing the compound according to this embodiment The compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by following the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0113] Specific examples of compounds according to this embodiment Specific examples of the compound according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is omitted.

[0114]

change

[0115]

change

[0116]

change

[0117]

change

[0118]

change

[0119]

change

[0120]

change

[0121]

change

[0122]

change

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132]

change

[0133]

change

[0134]

change

[0135]

change

[0136]

change

[0137]

change

[0138]

change

[0139]

change

[0140]

change

[0141]

change

[0142]

change

[0143]

change

[0144]

change

[0145]

change

[0146]

change

[0147]

change

[0148]

change

[0149]

change

[0150]

change

[0151]

change

[0152]

change

[0153]

change

[0154]

change

[0155]

change

[0156]

change

[0157]

change

[0158]

change

[0159]

change

[0160]

change

[0161]

change

[0162]

change

[0163]

change

[0164]

change

[0165]

change

[0166]

change

[0167] [ka]

[0168] [ka]

[0169] [ka]

[0170] [ka]

[0171] According to this embodiment, a compound with high PLQY can be provided. The method for measuring PLQY will be explained in the Examples section below.

[0172] Second Embodiment (Materials for organic electroluminescence devices) The material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment. One aspect of the material for organic electroluminescence devices includes only the compound according to the first embodiment, and another aspect of the material for organic electroluminescence devices includes the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the organic electroluminescence device material of the present embodiment, the compound according to the first embodiment is preferably a host material. In this case, the material for organic electroluminescence devices may contain the compound according to the first embodiment as a host material and other compounds such as a dopant material. In the material for an organic electroluminescence device of this embodiment, the compound according to the first embodiment is preferably a delayed fluorescent material.

[0173] Third Embodiment [Organic electroluminescence element] The organic EL element according to this embodiment will be described. The organic EL element according to the present embodiment includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer includes a plurality of layers made of an organic compound stacked together. The organic layer may further include an inorganic compound.

[0174] In the organic EL device according to this embodiment, the organic layer contains the compound according to the first embodiment.

[0175] The organic EL element according to this embodiment has a first organic layer as an organic layer.

[0176] In the organic EL device of the present embodiment, at least one of the organic layers is preferably an emitting layer. In the present embodiment, it is preferable that the emitting layer contains the compound according to the first embodiment.

[0177] The organic layer may be, for example, composed of one light-emitting layer, or may include a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, and may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.

[0178] In one embodiment, the first organic layer as an emitting layer may include a metal complex. In one embodiment, it is also preferable that the first organic layer serving as the light-emitting layer does not contain a metal complex. In one embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material). In one embodiment, the light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.

[0179] FIG. 3 shows a schematic configuration of one example of the organic EL element according to this embodiment. 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 configured by laminating a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.

[0180] (Light Emitting Layer) In this embodiment, the first organic layer is an emitting layer. The first organic layer as an emitting layer contains a first compound and a second compound. The first compound in the first organic layer is preferably the compound according to the first embodiment. In this embodiment, the first compound is preferably a host material (sometimes called a matrix material), and the second compound is preferably a dopant material (sometimes called a guest material, emitter, or luminescent material). In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0181] <First compound> The first compound is a compound according to a first embodiment. The first compound is preferably a delayed fluorescent compound.

[0182] <Second Compound> The second compound is preferably a fluorescent compound that does not exhibit delayed fluorescence.

[0183] The second compound according to the present embodiment may be a fluorescent material.Specific examples of the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0184] In this embodiment, the second compound is preferably a compound represented by the following general formula (2).

[0185] [ka]

[0186] 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 are each 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 and R 25 and R 26 any one or more of the pairs of Y and R as Substituents 21 ~R 26 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Halogen atoms, Carboxy group, a substituted or unsubstituted ester group; a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, Nitro group, Cyano group, a substituted or unsubstituted silyl group, and selected from the group consisting of substituted or unsubstituted siloxanyl groups; Z 21 and Z 22 are each independently a substituent or Z 21 and Z 22 are bonded together to form a ring, Z as a Substituent 21 and Z 22 are each independently Halogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and The aryloxy group is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

[0187] When the second compound is a fluorescent compound, the second compound preferably exhibits emission having a main peak wavelength of 400 nm or more and 700 nm or less. In this specification, the main peak wavelength is the wavelength at which the compound to be measured is 10 -6 Moles / L > 10 -5 This refers to the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of mol / L or less. The measurement device used is a spectrofluorophotometer (Hitachi High-Tech Science, F-7000).

[0188] The second compound preferably exhibits red or green emission. In this specification, red emission refers to emission whose main peak wavelength in the fluorescence spectrum is within the range of 600 nm or more and 660 nm or less. 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 further preferably 610 nm or more and 630 nm or less. In this specification, green emission refers to emission having a main peak wavelength in the fluorescence spectrum within the range of 500 nm or more and 560 nm or less. 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 further preferably 510 nm or more and 530 nm or less. In this specification, blue emission refers to emission having a main peak wavelength in the fluorescence spectrum within the range of 430 nm or more and 480 nm or less. 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.

[0189] Method for producing the second compound The second compound can be prepared by a known method.

[0190] -Specific example of the second compound Specific examples of the second compound according to this embodiment are shown below. Note that the second compound in the present invention is not limited to these specific examples. The coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be represented in various ways, such as a solid line, a dashed line, an arrow, or omitted. In this specification, it is represented by a solid line, a dashed line, or omitted.

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] <Relationship between the first compound and the second compound in the light-emitting layer> In the organic EL device of this embodiment, it is preferable that the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3). S1(M1)>S1(M2)…(Math 3)

[0199] Energy gap T at 77[K] of the first compound 77K (M1) is the energy gap T at 77[K] of the second compound 77K It is preferable that the value is larger than (M2). In other words, it is preferable that the relationship of the following formula (5) is satisfied. T 77K (M1)>T 77K (M2) …(Number 5)

[0200] When the organic EL device of this embodiment is caused to emit light, it is preferable that the second compound mainly emits light in the light-emitting layer.

[0201] TADF mechanism FIG. 4 is a diagram showing an example of the relationship between the energy levels of the second compound M2 and the first compound M1 in the light-emitting layer. In FIG. 4, 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. The dashed arrow from S1(M1) to S1(M2) in FIG. 4 represents a Forster type energy transfer from the lowest excited singlet state of the first compound M1 to the second compound M2. As shown in FIG. 4, when a compound with a small ΔST(M1) is used as the first compound M1, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) by thermal energy. Then, Förster 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 the internal efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0202] The organic EL element of this embodiment preferably emits red or green light. When the organic EL element of the present 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. When the organic EL element of the present 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. When 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.

[0203] The main peak wavelength of the light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the main peak wavelength (unit: nm).

[0204] Thickness of the light-emitting layer The thickness of the light-emitting layer in the organic EL device of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. When the thickness is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity are easily facilitated, and when the thickness is 50 nm or less, an increase in the driving voltage is easily suppressed.

[0205] Compound content in the light-emitting layer The contents of the first compound and the second compound in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably from 10% to 80% by mass, more preferably from 10% to 60% by mass, and even more preferably from 20% to 60% by mass. The content of the first compound may be from 90% to 99.9% by mass, from 95% to 99.9% by mass, or from 99% to 99.9% by mass. The content of the second compound is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass. In this embodiment, the light-emitting layer may contain materials other than the first compound and the second compound. The light-emitting layer may contain only one type of the first compound or two or more types thereof.The light-emitting layer may contain only one type of the second compound or two or more types thereof.

[0206] (substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate can also be used. A flexible substrate is a substrate that can be bent (flexible), and examples of such substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. An inorganic deposition film can also be used.

[0207] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. 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 metal materials (e.g., titanium nitride), etc. These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less. In addition, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method by using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide at 0.1 mass % or more and 1 mass % or less. In addition, it may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like. Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so that materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating and inkjet methods can be used.

[0208] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0209] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. In addition, examples of materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1, Other examples of aromatic amine compounds include 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. For example, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.

[0210] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly those that have a hole mobility of 10-6cm2 / Vs or more. The hole transport layer may be made of carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other substances may be used as long as they have a higher hole transporting property than an electron transporting property. Note that the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0211] (electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used as low molecular weight organic compounds. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(pt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances mentioned here are mainly 10 -6 cm 2The electron transport layer is a material having an electron mobility of 1 / Vs or more. Note that, as long as the material has a higher electron transporting property than a hole transporting property, any material other than the above may be used as the electron transport layer. The electron transport layer may be a single layer or a layer in which two or more layers made of the above materials are stacked. The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0212] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), or compounds thereof can be used. In addition, a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0213] (Layer formation method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but may be any known method, such as a dry film formation method, such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method, such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0214] (Film thickness) The film thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. In general, however, if the film thickness is too thin, defects such as pinholes are likely to occur, whereas if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness is usually preferably in the range of several nm to 1 μm.

[0215] The organic EL element according to the third embodiment includes, in an emitting layer, the compound of the first embodiment as a first compound, and a second compound having a minimum excited singlet energy smaller than that of the first compound. Since the organic EL element according to the third embodiment contains the compound according to the first embodiment (first compound) having a high PLQY, a high-performance organic EL element can be provided according to the third embodiment. Examples of the performance of the organic EL element include luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0216] Fourth Embodiment The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be given the same reference numerals or names, and the description will be omitted or simplified. In the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0217] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a third compound, but other points are the same as those of the third embodiment. That is, in the fourth embodiment, the light-emitting layer serving as the first organic layer contains a first compound, a second compound, and a third compound. In this embodiment, the first compound is preferably a host material and the second compound is preferably a dopant material.

[0218] <Third compound> The third compound may be a compound exhibiting delayed fluorescence or a compound exhibiting no delayed fluorescence.

[0219] The third compound is not particularly limited, but is preferably a compound other than an amine compound. For example, the third compound may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0220] The third compound is also preferably a compound containing at least one of a partial structure represented by the following general formula (31), a partial structure represented by the following general formula (32), a partial structure represented by the following general formula (33A), and a partial structure represented by the following general formula (34B) in one molecule.

[0221] [ka]

[0222] In the general formula (31), Y 31 ~Y 36 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, However, Y 31 ~Y 36 at least one of the carbon atoms is bonded to another atom in the molecule of the third compound, In the general formula (32), Y 41 ~Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, However, Y 41 ~Y 48 at least one of the carbon atoms is bonded to another atom in the molecule of the third compound, X 30 is a nitrogen atom, or an oxygen atom, or a sulfur atom that is bonded to another atom in the molecule of the third compound. In the general formulae (33A) and (34A), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0223] In the general formula (32), Y 41 ~Y 48 It is also preferred that at least two of the carbon atoms are carbon atoms bonded to other atoms in the molecule of the third compound, and a ring structure containing the carbon atoms is constructed. For example, the partial structure represented by the general formula (32) is preferably any partial structure selected from the group consisting of partial structures represented by the following general formulae (321), (322), (323), (324), (325), and (326).

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] In the general formulae (321) to (326), X 30 are each independently a nitrogen atom, an oxygen atom, or a sulfur atom bonded to another atom in a molecule of a third compound, Y 41 ~Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, X 31 are each independently a nitrogen atom, an oxygen atom, a sulfur atom, or a carbon atom that is bonded to another atom in the molecule of the third compound, Y 61 ~Y 64 are each independently a nitrogen atom or a carbon atom that is bonded to another atom in the molecule of the third compound. In this embodiment, the third compound preferably has a partial structure represented by the general formula (323) among the general formulae (321) to (326).

[0228] The partial structure represented by the general formula (31) is preferably contained in the third compound as at least one group selected from the group consisting of a group represented by the following general formula (33) and a group represented by the following general formula (34): It is also preferable that the third compound has at least one of the partial structures represented by the following general formula (33) and the following general formula (34). Since the bonding sites are located in the meta positions as in the partial structures represented by the following general formula (33) and the following general formula (34), the energy gap T 77K (M3) can be kept high.

[0229] [ka]

[0230] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 each independently represents a nitrogen atom or CR 31 It is. In the general formula (34), Y 32 , Y 34 , and Y 36 each independently represents a nitrogen atom or CR 31 It is. In the general formulae (33) and (34), R 31 are each independently a hydrogen atom or a substituent, R as a Substituent 31 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, Halogen atoms, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of: However, the above R 31 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the above formula (I) is preferably a non-condensed ring. In the general formula (33) and the general formula (34), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0231] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 are each independently 31 Preferably, R 31 are either identical to or different from each other. In addition, in the general formula (34), Y 32 , Y 34 , and Y 36 are each independently 31 Preferably, R 31 are either identical to or different from each other.

[0232] The substituted germanium group is -Ge(R 301 )3. 301 are each independently a substituent. 301 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 301 are the same or different from each other.

[0233] The partial structure represented by the general formula (32) is preferably contained in the third compound as at least any one group selected from the group consisting of groups represented by the following general formulae (35) to (39) and the following general formula (30a):

[0234] [ka]

[0235] [ka]

[0236] [ka]

[0237] In the general formula (35), Y 41 or Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formulas (36) and (37), Y 41 ~Y 45 , Y 47 , and Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 , and Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (39), Y 42 ~Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (30a), Y 42 ~Y 47 each independently represents a nitrogen atom or CR 32 It is. In the general formulae (35) to (39) and (30a), R 32 are each independently a hydrogen atom or a substituent, R as a Substituent 32 teeth, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, Halogen atoms, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of Multiple R 32 are the same or different from each other. In the general formulae (37) to (39) and (30a), X 30 is NR 33 , an oxygen atom, or a sulfur atom; R 33 teeth, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, fluorine atom, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of Multiple R 33 are the same or different from each other. However, the above R 33 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the above formula (I) is preferably a non-condensed ring. In the general formulae (35) to (39) and (30a), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0238] In the general formula (35), Y 41 ~Y 48 are each independently 32 In the general formula (36) and the general formula (37), Y 41 ~Y 45 ,Y 47 , and Y 48 are each independently 32 In the general formula (38), Y 41 ,Y 42 ,Y 44 ,Y 45 ,Y 47 , and Y 48 are each independently 32 In the general formula (39), Y 42 ~Y 48 are each independently 32 In the general formula (30a), Y 42 ~Y 47 are each independently 32 Preferably, R 32 are the same or different from each other.

[0239] In the third compound, X 30is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

[0240] In the third compound, R 31 , and R 32 are each independently a hydrogen atom or a substituent, and R 31 and R as a substituent 32 R is preferably any group 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 aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. 31 , and R 32 is more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. 31 and R as a substituent 32 When is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group is preferably a non-condensed ring.

[0241] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[0242] Method for producing the third compound The third compound can be produced by, for example, the methods described in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650, etc. In addition, the third compound can be produced by, for example, using a known alternative reaction and raw materials suited to the target product.

[0243] Examples of the substituent in the third compound are as follows, but the present invention is not limited to these examples.

[0244] Specific examples of aryl groups (sometimes referred to as aromatic hydrocarbon groups) include phenyl groups, tolyl groups, xylyl groups, naphthyl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, benzo[c]phenanthryl groups, benzo[g]chrysenyl groups, benzanthryl groups, triphenylenyl groups, fluorenyl groups, 9,9-dimethylfluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, and fluoranthenyl groups, and preferred examples include phenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, naphthyl groups, triphenylenyl groups, and fluorenyl groups. Examples of the aryl group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group. As the specific examples indicate, aryl groups include both fused and non-fused aryl groups. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a triphenylenyl group, or a fluorenyl group.

[0245] Specific examples of heteroaryl groups (which may be referred to as heterocyclic groups, heteroaromatic ring groups, or aromatic heterocyclic groups) include a pyrrolyl group, a pyrazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a pyridyl group, a triazinyl group, an indolyl group, an isoindolyl group, an imidazolyl group, a benzimidazolyl group, an indazolyl group, an imidazo[1,2-a]pyridinyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, an azadibenzofuranyl group, a thiophenyl group, a benzothienyl group, a dibenzothienyl group, an azadibenzothienyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinol ... Examples of such groups include a nazolinyl group, a naphthyridinyl group, a carbazolyl group, an azacarbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an oxazolyl group, an oxadiazolyl group, a furazanyl group, a benzoxazolyl group, a thienyl group, a thiazolyl group, a thiadiazolyl group, a benzthiazolyl group, a triazolyl group, and a tetrazolyl group. Preferred examples of such groups include a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothienyl group. The heteroaryl group is preferably a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, or an azadibenzothienyl group, and more preferably a dibenzofuranyl group, a dibenzothienyl group, an azadibenzofuranyl group, or an azadibenzothienyl group.

[0246] In the third compound, the substituted silyl group is also preferably selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group. Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group. Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group. Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tritolylsilyl group.

[0247] In the third compound, the substituted phosphine oxide group is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include a diphenylphosphine oxide group and a ditolylphosphine oxide group.

[0248] In the third compound, examples of the substituted carboxy group include a benzoyloxy group.

[0249] Specific examples of the third compound Specific examples of the third compound according to this embodiment are shown below. Note that the third compound in the present invention is not limited to these specific examples.

[0250] [ka]

[0251] [ka]

[0252] [ka]

[0253] [ka]

[0254] <Relationship between the first compound, the second compound, and the third compound in the light-emitting layer> In the organic EL device of this embodiment, it is preferable that the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M1) (Number 2)

[0255] Energy gap T at 77[K] for the third compound 77K (M3) is the energy gap T of the first compound at 77[K] 77K It is preferable that it is larger than (M1). Energy gap T at 77[K] for the third compound 77K (M3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (M2).

[0256] It is preferable that the lowest excited singlet energy S1(M1) of the first compound, the lowest excited singlet energy S1(M2) of the second compound, and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2A). S1(M3)>S1(M1)>S1(M2)…(Number 2A)

[0257] Energy gap T of the first compound at 77[K] 77K (M1) and the energy gap T at 77[K] of the second compound 77K (M2) and the energy gap T at 77[K] of the third compound 77K It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical formula 2B). T 77K (M3)>T 77K (M1)>T 77K (M2) …(Number 2B)

[0258] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer. The organic EL element of this embodiment preferably emits red or green light, similarly to the organic EL element of the third embodiment. The main peak wavelength of the light emitted from the organic EL element can be measured in the same manner as in the organic EL element of the third embodiment.

[0259] Compound content in the light-emitting layer The contents of the first compound, the second compound, and the third compound in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass. The content of the second compound is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass. The content of the third compound is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of the first compound or may contain two or more types. The light-emitting layer may contain only one type of the second compound or may contain two or more types. The light-emitting layer may contain only one type of the third compound or may contain two or more types.

[0260] FIG. 5 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-emitting layer. In FIG. 5, 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. The dashed arrow from S1(M1) to S1(M2) in FIG. 5 represents the Förster type energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound. As shown in Figure 5, when a compound with a small 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) by thermal energy. Then, Förster type energy transfer occurs from the lowest excited singlet state S1(M1) of the first compound to 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 the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0261] The organic EL element according to the fourth embodiment includes, in an emitting layer, the compound of the first embodiment as a first compound, a second compound having a lower minimum excited singlet energy than the first compound, and a third compound having a higher minimum excited singlet energy than the first compound. Since the organic EL element according to the fourth embodiment contains the compound according to the first embodiment (first compound) having high PLQY, according to the fourth embodiment, a high-performance organic EL element can be provided. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0262] Fifth Embodiment The configuration of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third or fourth embodiment will be given the same reference numerals or names, and the description will be omitted or simplified. In the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third or fourth embodiment can be used.

[0263] The organic EL element according to the fifth embodiment differs from the organic EL element according to the third or fourth embodiment in that the light-emitting layer contains the first compound and the third compound but does not contain the second compound, and is otherwise similar to the organic EL element according to the third or fourth embodiment. That is, in the fifth embodiment, the light-emitting layer serving as the first organic layer contains a first compound and a third compound. In this embodiment, the third compound is preferably a host material, and the first compound is preferably a dopant material. In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0264] <First compound> The first compound is a compound according to a first embodiment. The first compound is preferably a delayed fluorescent compound.

[0265] <Third compound> The third compound is the same as the third compound described in the fourth embodiment.

[0266] <Relationship between the first compound and the third compound in the light-emitting layer> In the organic EL device of this embodiment, it is preferable that the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M1) (Number 2)

[0267] Energy gap T at 77[K] for the third compound 77K (M3) is the energy gap T of the first compound at 77[K] 77K It is preferable that it is larger than (M1).

[0268] FIG. 6 is a diagram for explaining the principle of light emission according to an embodiment of the present invention. In Figure 6, 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. As shown in FIG. 6, when a compound with a small ΔST(M1) is used as the first compound, the lowest excited triplet state T1(M1) of the first compound can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) by thermal energy. By utilizing the reverse intersystem crossing that occurs in this first compound, for example, luminescence as shown in the following (i) or (ii) can be observed. (i) When the light-emitting layer does not contain a fluorescent dopant having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M1) of the first compound, light emission from the lowest excited singlet state S1(M1) of the first compound can be observed. (ii) When the emitting layer contains a fluorescent dopant (in the third or fourth embodiment, a fluorescent second compound) whose lowest excited singlet state S1 is smaller than the lowest excited singlet state S1 (M1) of the first compound, light emission from the fluorescent dopant can be observed. In the organic EL element of this embodiment, the light emission shown in (i) above can be observed. In the organic EL element of the third or fourth embodiment described above, the light emission shown in (ii) above can be observed.

[0269] Compound content in the light-emitting layer The contents of the first compound and the third compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, even 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. The content of the third compound is preferably 10% by mass or more and 90% by mass or less. The upper limit of the total content of the first compound and the third compound in the light-emitting layer is 100% by mass. The light-emitting layer may contain only one type of the first compound or two or more types thereof.The light-emitting layer may contain only one type of the third compound or two or more types thereof.

[0270] Since the organic EL element according to the fifth embodiment contains the compound according to the first embodiment (first compound) having high PLQY, according to the fifth embodiment, a high-performance organic EL element can be provided. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0271] Sixth Embodiment (electronic equipment) The electronic device according to the present embodiment is equipped with any of the organic EL elements according to the above-mentioned embodiments. Examples of the electronic device include display devices and light-emitting devices. Examples of the display device include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lamps.

[0272] [Other explanations] In this specification, Rx and Ry are bonded to each other to form a ring means, for example, that Rx and Ry contain a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom, and an atom contained in Rx (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom) and an atom contained in Ry (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom) are bonded via a single bond, a double bond, a triple bond, or a divalent linking group to form a ring having 5 or more ring-forming atoms (specifically, a heterocyclic ring or an aromatic hydrocarbon ring). x is a number, a letter, or a combination of a number and a letter. y is a number, a letter, or a combination of a number and a letter. The divalent linking group is not particularly limited, and examples thereof include -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa-, and groups formed by combining two or more of these linking groups. Specific examples of the heterocycle include the ring structures (heterocycles) obtained by removing a bond from the "heteroaryl group Sub2" exemplified in the "Explanation of each substituent in the general formula" described below. These heterocycles may have a substituent. Specific examples of the aromatic hydrocarbon ring include the ring structures (aromatic hydrocarbon rings) obtained by removing a bond from the "aryl group Sub1" exemplified in the "Explanation of each substituent in the general formula" described below. These aromatic hydrocarbon rings may have a substituent. Examples of Ra include a substituted or unsubstituted alkyl group Sub3 having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group Sub1 having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group Sub2 having 5 to 30 ring atoms, which are exemplified in the "Explanation of each substituent in the general formula" described later. For example, when Rx and Ry are bonded to each other to form a ring, it means that in the molecular structure represented by the following general formula (E1), an atom included in Rx1 and an atom included in Ry1 form a ring (ring structure) E represented by general formula (E2); in the molecular structure represented by general formula (F1), an atom included in Rx1 and an atom included in Ry1 form a ring F represented by general formula (F2); in the molecular structure represented by general formula (G1), an atom included in Rx1 and an atom included in Ry1 form a ring G represented by general formula (G2); in the molecular structure represented by general formula (H1), an atom included in Rx1 and an atom included in Ry1 form a ring H represented by general formula (H2); in the molecular structure represented by general formula (I1), an atom included in Rx1 and an atom included in Ry1 form a ring I represented by general formula (I2). In the general formulae (E1) to (I1), * each independently represents a bonding position with other atoms in one molecule. The two * in the general formula (E1) correspond to the two * in the general formula (E2), the two * in the general formula (F1) correspond to the two * in the general formula (F2), the two * in the general formula (G1) correspond to the two * in the general formula (G2), the two * in the general formula (H1) correspond to the two * in the general formula (H2), and the two * in the general formula (I1) correspond to the two * in the general formula (I2).

[0273] [ka]

[0274] [ka]

[0275] In the molecular structures represented by the general formulae (E2) to (I2), E to I each represent a ring structure (a ring having 5 or more ring atoms). In the general formulae (E2) to (I2), * each independently represents a bonding position to other atoms in one molecule. The two * in the general formula (E2) correspond to the two * in the general formula (E1), respectively. Similarly, the two * in the general formulae (F2) to (I2) correspond to the two * in the general formulae (F1) to (I1), respectively.

[0276] For example, in general formula (E1), when Rx1 and Ry1 are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted benzene ring, the molecular structure represented by general formula (E1) becomes a molecular structure represented by the following general formula (E3), where the two * in general formula (E3) each independently correspond to the two * in general formula (E2) and general formula (E1). For example, in general formula (E1), when Rx1 and Ry1 are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted pyrrole ring, the molecular structure represented by general formula (E1) becomes a molecular structure represented by the following general formula (E4). Here, the two * in general formula (E4) each independently correspond to the two * in general formula (E2) and general formula (E1). In general formulas (E3) and (E4), * each independently represent a bonding position to another atom in one molecule.

[0277] [ka]

[0278] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridinyl group has 5 ring carbon atoms, and a furanyl group has 4 ring carbon atoms. In addition, when a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms. In addition, when a fluorene ring is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring carbon atoms.

[0279] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). Atoms that do not constitute a ring, and atoms contained in the substituent when the ring is substituted with a substituent, are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, a pyridine ring has 6 ring-forming atoms, a quinazoline ring has 10 ring-forming atoms, and a furan ring has 5 ring-forming atoms. The hydrogen atoms and atoms constituting the substituents bonded to the carbon atoms of the pyridine ring and the quinazoline ring are not included in the number of ring-forming atoms. In addition, when a fluorene ring is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

[0280] Explanation of each substituent in the general formula (explanation of each substituent) Next, each of the substituents in the general formulae in this specification will be described.

[0281] An aryl group (sometimes referred to as an aromatic hydrocarbon group) in this specification is, for example, an aryl group Sub1. The aryl group Sub1 preferably has 6 to 30 ring carbon atoms, more preferably 6 to 20 ring carbon atoms, further preferably 6 to 14 ring carbon atoms, and even more preferably 6 to 12 ring carbon atoms. The aryl group Sub1 in this specification is, for example, at least one group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, a benzo[a]anthryl group, a benzo[c]phenanthryl group, a triphenylenyl group, a benzo[k]fluoranthenyl group, a benzo[g]chrysenyl group, a benzo[b]triphenylenyl group, a picenyl group, and a perylenyl group.

[0282] Among the above aryl groups Sub1, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl and fluorenyl groups are preferred. As for the 1-fluorenyl, 2-fluorenyl, 3-fluorenyl and 4-fluorenyl groups, it is preferred that the carbon atom at the 9th position is substituted with a substituted or unsubstituted alkyl group Sub3 or a substituted or unsubstituted aryl group Sub1 as described later in this specification.

[0283] The heteroaryl group (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) in this specification is, for example, a heterocyclic group Sub2. The heterocyclic group Sub2 is a group containing, as a heteroatom, at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, a selenium atom, and a germanium atom. The heterocyclic group Sub2 is preferably a group containing, as a heteroatom, at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen. The heterocyclic group Sub2 preferably has 5 to 30 ring atoms, more preferably 5 to 20, and even more preferably 5 to 14 ring atoms.

[0284] In the present specification, the heterocyclic group Sub2 is, for example, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolinyl group, a naphthyridinyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, a benzimidazolyl group, an indazolyl group, an imidazopyridinyl group, a benztriazolyl group, a carbazolyl group, a furyl group, a thienyl group, an oxy group, At least one group selected from the group consisting of an azolyl group, a thiazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a piperidinyl group, a pyrrolidinyl group, a piperazinyl group, a morpholyl group, a phenazinyl group, a phenothiazinyl group, and a phenoxazinyl group.

[0285] Among the heterocyclic groups Sub2, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, and 9-carbazolyl are even more preferred. In the 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, and 4-carbazolyl groups, 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 defined herein.

[0286] In addition, in this specification, the heterocyclic group Sub2 may be, for example, a group derived from a partial structure represented by the following general formulae (XY-1) to (XY-18).

[0287] [ka]

[0288] [ka]

[0289] [ka]

[0290] In the general formulae (XY-1) to (XY-18), X A and Y A are each independently a heteroatom, and are preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. The partial structures represented by the general formulae (XY-1) to (XY-18) have a bond at any position to form a heterocyclic group, and this heterocyclic group may have a substituent.

[0291] In this specification, the heterocyclic group Sub2 may be, for example, a group represented by the following general formulae (XY-19) to (XY-22). The position of the bond may also be changed appropriately.

[0292] [ka]

[0293] In this specification, the alkyl group may be any of a straight-chain alkyl group, a branched-chain alkyl group, and a cyclic alkyl group. An alkyl group herein is, for example, the alkyl group Sub3. The linear alkyl group in this specification is, for example, the linear alkyl group Sub 31 It is. In the present specification, the branched alkyl group is, for example, the branched alkyl group Sub 32 It is. The cyclic alkyl group in this specification is, for example, the cyclic alkyl group Sub 33 (Cycloalkyl group Sub 331(sometimes referred to as "the Japan-U.S. Trademark Office"). The alkyl group Sub3 may be, for example, a straight-chain alkyl group Sub 31 , branched alkyl group Sub 32 , and the cyclic alkyl group Sub 33 and at least one group selected from the group consisting of: The linear alkyl group Sub 31 or a branched alkyl group Sub 32 The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and even more preferably 1 to 6. The cycloalkyl groups Sub 331 The number of ring carbon atoms of the cycloalkyl group Sub is preferably 3 to 30, more preferably 3 to 20, even more preferably 3 to 10, and even more preferably 5 to 8. 331 It is also preferable that the ring-forming carbon atoms number is 3 to 6.

[0294] The linear alkyl group Sub 31 or a branched alkyl group Sub 32 is, for example, at least one group selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl group, an amyl group, an isoamyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl group.

[0295] The above straight chain alkyl group Sub 31 or a branched alkyl group Sub 32As the alkyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an amyl group, an isoamyl group, and a neopentyl group are even more preferred.

[0296] The cyclic alkyl group Sub 33 is, for example, the cycloalkyl group Sub 331 It is.

[0297] The cycloalkyl groups Sub 331 is, for example, at least one group selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. 331 Among these, a cyclopentyl group and a cyclohexyl group are even more preferred.

[0298] A halogenated alkyl group in this specification is, for example, a halogenated alkyl group Sub4, which is, for example, an alkyl group Sub3 substituted with one or more halogen atoms, preferably fluorine atoms.

[0299] In this specification, the halogenated alkyl group Sub4 is, for example, at least one group selected from the group consisting of a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.

[0300] The substituted silyl group in this specification is, for example, a substituted silyl group Sub5, and the substituted silyl group Sub5 is, for example, an alkylsilyl group Sub 51 and the arylsilyl group Sub 52 and at least one group selected from the group consisting of:

[0301] The alkylsilyl group Sub 51is, for example, a trialkylsilyl group Sub having the above alkyl group Sub3. 511 It is. Trialkylsilyl group Sub 511 is, for example, at least one group selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a tri-n-butylsilyl group, a tri-n-octylsilyl group, a triisobutylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, a dimethyl-n-propylsilyl group, a dimethyl-n-butylsilyl group, a dimethyl-t-butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. 511 The three alkyl groups Sub3 in the formula may be the same or different.

[0302] The arylsilyl group Sub 52 is, for example, a dialkylarylsilyl group Sub 521 , alkyldiarylsilyl group Sub 522 , and the triarylsilyl group Sub 523 and at least one group selected from the group consisting of:

[0303] Dialkylarylsilyl group Sub 521 is, for example, a dialkylarylsilyl group having two of the above alkyl groups Sub3 and one of the above aryl groups Sub1. 521 The number of carbon atoms is preferably 8 to 30.

[0304] Alkyldiarylsilyl group Sub 522 is, for example, an alkyldiarylsilyl group having one of the above alkyl groups Sub3 and two of the above aryl groups Sub1. 522 The number of carbon atoms is preferably 13 to 30.

[0305] Triarylsilyl group Sub 523is, for example, a triarylsilyl group having three of the above aryl groups Sub1. 523 The number of carbon atoms is preferably 18 to 30.

[0306] The substituted or unsubstituted alkylsulfonyl group in this specification is, for example, an alkylsulfonyl group Sub6, and the alkylsulfonyl group Sub6 is -SO2R w It is expressed as -SO2R w R in w represents the above-mentioned substituted or unsubstituted alkyl group Sub3.

[0307] An aralkyl group (sometimes referred to as an arylalkyl group) in this specification is, for example, an aralkyl group Sub7. The aryl group in the aralkyl group Sub7 includes, for example, at least one of the above aryl group Sub1 and the above heteroaryl group Sub2.

[0308] In the present specification, the aralkyl group Sub7 is preferably a group having an aryl group Sub1, and is represented as -Z3-Z4. Z3 is, for example, an alkylene group corresponding to the above alkyl group Sub3. Z4 is, for example, the above aryl group Sub1. In the aralkyl group Sub7, the aryl portion preferably has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl portion preferably has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6). This aralkyl group Sub7 is, for example, at least one group selected from the group consisting of benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0309] The alkoxy group in this specification is, for example, the alkoxy group Sub8, which is represented as -OZ1. This Z1 is, for example, the above alkyl group Sub3. The alkoxy group Sub8 preferably has 1-30 carbon atoms, and more preferably has 1-20 carbon atoms. The alkoxy group Sub8 is, for example, at least one group selected from the group consisting of a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.

[0310] A halogenated alkoxy group in this specification is, for example, a halogenated alkoxy group Sub9, which is, for example, an alkoxy group in which the above alkoxy group Sub8 is substituted with one or more halogen atoms, preferably fluorine atoms.

[0311] The aryloxy group (sometimes referred to as an arylalkoxy group) in this specification is, for example, an arylalkoxy group Sub 10 The arylalkoxy group Sub 10 The aryl group in the formula (I) includes at least one of an aryl group Sub1 and a heteroaryl group Sub2.

[0312] The arylalkoxy group Sub 10 is represented as -OZ2. Z2 is, for example, an aryl group Sub1 or a heteroaryl group Sub2. An arylalkoxy group Sub 10 The number of ring carbon atoms of this arylalkoxy group Sub is preferably 6 to 30, and more preferably 6 to 20. 10 Examples of the aryl group include a phenoxy group.

[0313] The substituted amino group in this specification is, for example, the substituted amino group Sub 11 and the substituted amino group Sub 11 is, for example, an arylamino group Sub 111 and alkylamino groups Sub 112and at least one group selected from the group consisting of: Arylamino GroupsSub 111 -NHR V1 , or -N(R V1 )2. This R V1 is, for example, an aryl group Sub1. V1 )2 in two R V1 are the same or different. Alkylamino group Sub 112 -NHR V2 , or -N(R V2 )2. This R V2 is, for example, the alkyl group Sub3. V2 )2 in two R V2 are the same or different.

[0314] The alkenyl group in this specification is, for example, the alkenyl group Sub 12 and the alkenyl group Sub 12 is either a straight chain or a branched chain, and is, for example, at least one group selected from the group consisting of a vinyl group, a propenyl group, a butenyl group, an oleyl group, an eicosapentaenyl group, a docosahexaenyl group, a styryl group, a 2,2-diphenylvinyl group, a 1,2,2-triphenylvinyl group, and a 2-phenyl-2-propenyl group.

[0315] The alkynyl group in this specification is, for example, the alkynyl group Sub 13 and the alkynyl group Sub 13 may be either a straight chain or a branched chain, and is, for example, at least one group selected from the group consisting of ethynyl, propynyl, and 2-phenylethynyl.

[0316] The alkylthio group in this specification is, for example, the alkylthio group Sub 14 It is. Alkylthio group Sub 14 -SR V3 This R V3is, for example, the alkyl group Sub3. 14 The carbon number of the group is preferably 1 to 30, and more preferably 1 to 20. The arylthio group in this specification is, for example, the arylthio group Sub 15 It is. Arylthio group Sub 15 -SR V4 This R V4 is, for example, an aryl group Sub1. 15 The ring-forming carbon atoms are preferably 6 to 30, and more preferably 6 to 20.

[0317] In this specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferred.

[0318] The substituted phosphino group in this specification is, for example, the substituted phosphino group Sub 16 and the substituted phosphino group Sub 16 is, for example, a phenylphosphanyl group.

[0319] The arylcarbonyl group in this specification is, for example, the arylcarbonyl group Sub 17 and the arylcarbonyl group Sub 17 is represented as -COY'. This Y' is, for example, an aryl group Sub1. In the present specification, the arylcarbonyl group Sub 17 is, for example, at least one group selected from the group consisting of a phenylcarbonyl group, a diphenylcarbonyl group, a naphthylcarbonyl group, and a triphenylcarbonyl group.

[0320] The acyl group in this specification is, for example, the acyl group Sub 18 and the acyl group Sub 18 is represented as -COR'. This R' is, for example, an alkyl group Sub3. In this specification, the acyl group Sub 18is, for example, at least one group selected from the group consisting of an acetyl group and a propionyl group.

[0321] Substituted phosphoryl groups herein include, for example, the substituted phosphoryl group Sub 19 and a substituted phosphoryl group Sub 19 is represented by the following general formula (P).

[0322] [ka]

[0323] In the general formula (P), Ar P1 and Ar P2 is any substituent selected from the group consisting of the alkyl group Sub3 and the aryl group Sub1.

[0324] The ester group in this specification is, for example, the ester group Sub 20 and the ester group Sub 20 is, for example, at least one group selected from the group consisting of an alkyl ester group and an aryl ester group. The alkyl ester group in this specification is, for example, the alkyl ester group Sub 201 and the alkyl ester group Sub 201 is -C(=O)OR E It is expressed as R E is, for example, the above-mentioned substituted or unsubstituted alkyl group Sub3 (preferably having 1 to 10 carbon atoms). The aryl ester group in this specification is, for example, the aryl ester group Sub 202 and the aryl ester group Sub 202 is -C(=O)OR Ar It is expressed as R Ar is, for example, the above substituted or unsubstituted aryl group Sub1.

[0325] The siloxanyl group in this specification is, for example, the siloxanyl group Sub 21and the siloxanyl group Sub 21 is a silicon compound group via an ether bond. 21 is, for example, a trimethylsiloxanyl group.

[0326] In this specification, a carbamoyl group is represented by -CONH2. The substituted carbamoyl group in this specification is, for example, the carbamoyl group Sub 22 and the carbamoyl group Sub 22 -CONH-Ar C , or -CONH-R C It is expressed as Ar C is, for example, at least one group selected from the group consisting of the substituted or unsubstituted aryl group Sub1 (preferably having 6 to 10 ring carbon atoms) and the heteroaryl group Sub2 (preferably having 5 to 14 ring atoms). C may be a group formed by bonding an aryl group Sub1 and a heteroaryl group Sub2. R C is, for example, the above-mentioned substituted or unsubstituted alkyl group Sub3 (preferably having 1 to 6 carbon atoms).

[0327] In the present specification, the term "ring carbon atom" refers to a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. The term "ring atom" refers to a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

[0328] In this specification, unless specified as "protium atom" or "deuterium atom", "hydrogen atom" includes isotopes having different numbers of neutrons, i.e., protium, deuterium, and tritium.

[0329] In the present specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0330] Hereinafter, the alkyl group Sub3 is the straight-chain alkyl group Sub described in "Description of each substituent". 31 , branched alkyl group Sub 32 , and the cyclic alkyl group Sub 33 The term "N" means any one or more groups represented by the formula: Similarly, the substituted silyl group Sub5 is an alkylsilyl group Sub 51 and the arylsilyl group Sub 52 The term "N" means any one or more groups represented by the formula: Similarly, the substituted amino group Sub 11 The arylamino group Sub 111 and alkylamino groups Sub 112 The term "N" means any one or more groups represented by the formula:

[0331] In the present specification, examples of the substituent in the case of "substituted or unsubstituted" include the substituent R F1 and the substituent R F1 are aryl groups Sub1, heteroaryl groups Sub2, alkyl groups Sub3, halogenated alkyl groups Sub4, substituted silyl groups Sub5, alkylsulfonyl groups Sub6, aralkyl groups Sub7, alkoxy groups Sub8, halogenated alkoxy groups Sub9, arylalkoxy groups Sub 10 , substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16 , arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 , a carbamoyl group Sub 22 , an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxy group, a thiol group, a nitro group, and a carboxy group.

[0332] In the present specification, the substituent R in the case of "substituted or unsubstituted" F1 is a diarylboron group (Ar B1 Ar B2 B-) may be used. B1 and Ar B2 Examples of Ar include the aryl group Sub1 described above. B1 Ar B2 B-Ar B1 and Ar B2 are the same or different.

[0333] Substituent R F1 Specific examples and preferred groups of the substituents are those in the "Description of Each Substituent" (e.g., aryl group Sub1, heteroaryl group Sub2, alkyl group Sub3, halogenated alkyl group Sub4, substituted silyl group Sub5, alkylsulfonyl group Sub6, aralkyl group Sub7, alkoxy group Sub8, halogenated alkoxy group Sub9, arylalkoxy group Sub 10 , substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16 , arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 and the carbamoyl group Sub 22 Specific examples and preferred groups of the same as those of the above-mentioned aryl group are mentioned.

[0334] Substituent R in the case of "substituted or unsubstituted" F1 are aryl groups Sub1, heteroaryl groups Sub2, alkyl groups Sub3, halogenated alkyl groups Sub4, substituted silyl groups Sub5, alkylsulfonyl groups Sub6, aralkyl groups Sub7, alkoxy groups Sub8, halogenated alkoxy groups Sub9, arylalkoxy groups Sub 10, substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16 , arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 , a carbamoyl group 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 hydroxy group, a thiol group, a nitro group, and a carboxy group (hereinafter, referred to as the substituent R F2 These substituents R F2 may be bonded to each other to form a ring.

[0335] In the case of "substituted or unsubstituted", "unsubstituted" means the above-mentioned substituent R F1 This means that the ring is not substituted with a hydrogen atom and has a hydrogen atom bonded thereto.

[0336] In the present specification, the "number of carbon atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having a carbon number of XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and represents the number of carbon atoms when the ZZ group is substituted. F1 The number of carbon atoms is not included.

[0337] In the present specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and the number of substituents R F1 The number of atoms is not included.

[0338] The same applies to the term "substituted or unsubstituted" in the compounds or partial structures thereof described in this specification.

[0339] In this specification, when substituents are bonded to each other to form a ring, the ring structure is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.

[0340] In this specification, examples of the aromatic hydrocarbon group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-mentioned monovalent aryl group Sub1. In this specification, examples of the heterocyclic group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-mentioned monovalent heteroaryl group Sub2.

[0341] In this specification, a numerical range expressed using "AA to BB" means a range including the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0342] [Modification of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0343] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated. When the organic EL element has multiple light-emitting layers, at least one of the light-emitting layers may satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to a ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0344] In addition, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a blocking layer is disposed in contact with the light-emitting layer on the cathode side, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. In addition, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.). The light emitting layer and the barrier layer are preferably in contact with each other.

[0345] In addition, the specific structure and shape in carrying out the present invention may be other structures and shapes within the scope of the invention in which the object of the present invention can be achieved. EXAMPLES

[0346] EXAMPLES Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.

[0347] <Compound> The structures of the compounds represented by formula (1) according to Examples 1 to 16 or Synthesis Examples 1 to 10 are shown below.

[0348] [ka]

[0349] [ka]

[0350] [ka]

[0351] [ka]

[0352] The structures of the comparative compounds according to Comparative Examples 1 to 4 are shown below.

[0353] [ka]

[0354] The structures of the compounds used in the production of the organic EL devices according to Examples 10 to 16 and Comparative Examples 3 and 4 are shown below.

[0355] [ka]

[0356] [ka]

[0357] [ka]

[0358] [ka]

[0359] <Compound evaluation>

[0360] (Preparation of toluene solution) Compound A1 was dissolved in toluene to a concentration of 5 μmol / L to prepare a toluene solution of compound A1. Thereafter, the prepared solution was bubbled with nitrogen for 5 minutes and sealed to prevent mixing with outside air. For each of the compounds A2, A3, A4, A5, A6, A7, A8, A9, Ref-1 and Ref-2, a toluene solution was prepared in the same manner as for the compound A1. Then, the prepared solution was bubbled with nitrogen for 5 minutes and sealed to prevent the inclusion of outside air.

[0361] (Measurement of fluorescence quantum yield (PLQY)) For each of the prepared toluene solutions of compounds A1, A2, A3, A4, A5, A6, A7, A8, A9, Ref-1 and Ref-2, the PLQY was measured using an absolute PL (photoluminescence) quantum yield measurement device Quantaurus-QY (manufactured by Hamamatsu Photonics K.K.). The measurement results of 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. In Table 1, the PLQY values ​​are shown relative to the PLQY value of Comparative Example 1, which is set to 100. In Table 2, the PLQY values ​​are shown relative to the PLQY value of Comparative Example 2, which is set to 100. Specifically, the values ​​are calculated by the following formula. (PLQY relative value in Table 1) = {(PLQY absolute value of each Example or Comparative Example compound in Table 1) / (PLQY absolute value of comparative compound Ref-1)} × 100 (PLQY relative value in Table 2) = {(PLQY absolute value of each Example or Comparative Example compound in Table 2) / (PLQY absolute value of comparative compound Ref-2)} × 100

[0362] (Main peak wavelength of compound) A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the fluorescence spectrum (vertical axis: fluorescence emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the fluorescence spectrum was measured using a Hitachi spectrophotometer (device name: F-7000). Note that the fluorescence spectrum measuring device is not limited to the device used here. In the fluorescence spectrum, the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum was taken as the main peak wavelength. The measurement results of 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.

[0363] (Thermal activated delayed fluorescence) Delayed fluorescence of compound A1 The delayed fluorescence was confirmed by measuring the transient PL using the apparatus shown in Figure 1. Compound A1 was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption. In order to prevent quenching by oxygen, the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to prepare an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound A1, there are prompt luminescence (instantaneous luminescence) which is observed immediately from the excited state, and delayed luminescence (delayed luminescence) which is not observed immediately after the excitation and is observed later. In this embodiment, delayed fluorescent luminescence means that the amount of delayed luminescence (delayed luminescence) is 5% or more relative to the amount of prompt luminescence (instantaneous luminescence). Specifically, when the amount of prompt luminescence (instantaneous luminescence) is X P and the amount of delay light emission is X D When X D / X P This means that the value is 0.05 or more. The amount and ratio of prompt luminescence and delayed luminescence can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. It was confirmed that the amount of delayed luminescence (delayed luminescence) of compound A1 was 5% or more relative to the amount of prompt luminescence (prompt luminescence). Specifically, for compound A1, X D / X P It was confirmed that the value was 0.05 or higher. In the table, the notation ">0.05" means X D / X P This indicates that the value was greater than 0.05.

[0364] ·Delayed fluorescence of compounds A2 to A9, comparative compound Ref-1 and comparative compound Ref-2 The delayed fluorescence properties of compounds A2 to A9, comparative compounds Ref-1 and Ref-2 were confirmed in the same manner as above, except that compounds A2 to A9, comparative compounds Ref-1 and Ref-2 were used instead of compound A1. For compounds A2 to A9, comparative compound Ref-1 and comparative compound Ref-2, X D / X P The values ​​were all above 0.05.

[0365] (Singlet energy S1) The singlet energies S1 of the compounds A1 to A9, the comparative compounds Ref-1 and Ref-2 were measured by the above-mentioned solution method. The measurement results are shown in Tables 1 and 2.

[0366] (ΔST) T of compounds A1 to A9, comparative compound Ref-1 and comparative compound Ref-2 77K The T of Compounds A1 to A9, Comparative Compound Ref-1, and Comparative Compound Ref-2 were measured. 77K is the energy gap T 77K The measurement was performed according to the method described above. The above singlet energy S1 value and T 77KThe ΔST value of each compound is shown in Tables 1 and 2. In the tables, the notation "<0.01" indicates that the ΔST was less than 0.01 eV.

[0367] [Table 1]

[0368] [Table 2]

[0369] As shown in Table 1, compounds A1 to A4 represented by general formula (1) showed improved PLQY compared to comparative compound Ref-1 having the same paradicyanobenzene skeleton. As shown in Table 2, compounds A5 to A9 represented by general formula (1) showed improved PLQY compared to comparative compound Ref-2 having the same metadicyanobenzene skeleton.

[0370] <Fabrication of organic EL elements> An organic EL device was prepared as follows and evaluated.

[0371] Example 10 A 25mm x 75mm x 1.1mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the transparent electrode lines after cleaning was mounted on the substrate holder of a vacuum deposition apparatus, and the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The concentration of the compound HT-1 in the hole injection layer was 97% by mass, and the concentration of the compound HA was 3% by mass. Next, the compound HT-1 was deposited on this hole injection layer to form a first hole transport layer having a thickness of 110 nm. Next, the compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, the compound CBP was evaporated onto the second hole transport layer to form an electron blocking layer having a thickness of 5 nm. Next, on the electron blocking layer, the compounds Matrix-1 and Matrix-2 as the third compound and the compound A5 as the first compound were co-deposited to form a light-emitting layer having a thickness of 25 nm. The concentration of the compound Matrix-1 in the light-emitting layer was 25% by mass, the concentration of the compound Matrix-2 was 25% by mass, and the concentration of the compound A5 was 50% by mass. Next, the compound ET-1 was evaporated onto this light-emitting layer to form a hole-blocking layer having a thickness of 5 nm. Next, compound ET-2 was deposited on this hole blocking layer to form an electron transport layer having a thickness of 50 nm. Next, lithium fluoride (LiF) was evaporated onto this electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injecting electrode to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 10 is roughly shown as follows. 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) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the percentages (97%:3%) indicate the ratios (mass%) of compound HT-1 and compound HA in the hole injection layer, and the percentages (25%:25%:50%) indicate the ratios (mass%) of compound Matrix-1, compound Matrix-2, and compound A5 in the light-emitting layer. The same notation is used hereinafter.

[0372] (Examples 11 to 13) The organic EL devices of Examples 11 to 13 were prepared in the same manner as in Example 10, except that the first compound in the light-emitting layer in Example 10 was changed to the first compound shown in Table 3.

[0373] Comparative Example 3 The organic EL device of Comparative Example 3 was prepared in the same manner as in Example 10, except that the first compound in the light-emitting layer in Example 10 was changed to the first compound shown in Table 3.

[0374] Example 14 The organic EL device of Example 14 was produced in the same manner as in Example 10, except that the light-emitting layer in Example 10 was changed as follows. The light-emitting layer of the organic EL device of Example 14 was formed by co-evaporating compounds Matrix-1 and Matrix-2 as the third compound, compound A5 as the first compound, and compound GD as the second compound, as shown in Table 4. The concentration of compound Matrix-1 in the light-emitting layer was 24.5% by mass, the concentration of compound Matrix-2 was 24.5% by mass, the concentration of compound A5 was 50% by mass, and the concentration of compound GD was 1% by mass.

[0375] (Examples 15 to 16) The organic EL devices of Examples 15 and 16 were prepared in the same manner as in Example 14, except that the first compound in the light-emitting layer in Example 14 was changed to the first compound shown in Table 4.

[0376] Comparative Example 4 The organic EL device of Comparative Example 4 was prepared in the same manner as in Example 14, except that the first compound in the light-emitting layer in Example 14 was changed to the first compound shown in Table 4.

[0377] <Evaluation of organic EL elements> Driving voltage Current density is 10mA / cm 2 The voltage (unit: V) was measured when a current was passed between the anode and cathode so that

[0378] Table 3 shows the relative values ​​of the driving voltages of the organic EL elements of Examples 10 to 13 or Comparative Example 3 to the driving voltage of the organic EL element of Comparative Example 3, where the driving voltage of the organic EL element of Comparative Example 3 is taken as 1.00. Driving voltage (relative value)=[driving voltage of organic EL element of Examples 10 to 13 or Comparative Example 3] / [driving voltage of organic EL element of Comparative Example 3]

[0379] [Table 3]

[0380] Table 4 shows the relative values ​​of the driving voltages of the organic EL elements of Examples 14 to 16 or Comparative Example 4 to the driving voltage of the organic EL element of Comparative Example 4, where the driving voltage of the organic EL element of Comparative Example 4 is taken as 1.00. Driving voltage (relative value)=[driving voltage of organic EL element of Examples 14 to 16 or Comparative Example 4] / [driving voltage of organic EL element of Comparative Example 4]

[0381] [Table 4]

[0382] As is clear from Tables 3 and 4, the organic EL element using the compound represented by the general formula (1) had a lower driving voltage than the organic EL element using the comparative compound Ref-2 having the same metadicyanobenzene skeleton.

[0383] <Modifications of the embodiment> In Examples 10 to 13 shown in Table 3, two compounds, Compound Matrix-1 and Compound Matrix-2, are used as the third compound, but as a modification of these Examples, for example, an organic EL device using only Compound Matrix-1 as the third compound can be produced. When such a modification is made to Examples 10 to 13, the compounds in the light-emitting layer are as shown in Table 5 below.

[0384] [Table 5]

[0385] <Synthesis of Compounds>

[0386] Synthesis Example 1 The synthesis method of compound A1 is described below.

[0387] [ka]

[0388] 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 placed in a 500 mL eggplant flask and heated and stirred at 170°C. After heating and stirring for 4 hours, the material in the eggplant flask was heated to 175°C, stirred for another hour, and then cooled to room temperature. After cooling, 200 mL of water was added to the eggplant flask, and the precipitated solid was removed by celite filtration. The filtrate was extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated saline. The washed organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after the reduced pressure removal was isolated and purified by silica gel column chromatography to obtain 1,4-dichloro-2,5-difluorobenzene (4.11 g, 22.5 mmol). NMP is the abbreviation for N-methyl-2-pyrrolidone.

[0389] In a nitrogen atmosphere, 1,4-dichloro-2,5-difluorobenzene (4.11 g, 22.5 mmol), chlorotrimethylsilane (6.3 mL, 50 mmol), and THF (25 mL) were placed in a 200 mL three-neck flask. The materials in the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and then all of the prepared LDA was added dropwise. The solution obtained by adding all of the LDA dropwise was stirred at room temperature for 2 hours. After stirring, water (10 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, dried with magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 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. Chlorotrimethylsilane may be abbreviated as TMSCl. LDA is an abbreviation for Lithium Diisopropyl Amide.

[0390] In a nitrogen atmosphere, 2,5-dichloro-3,6-difluoro-1,4-phenylenebistrimethylsilane (6.61 g, 20.2 mmol) and dichloromethane (100 mL) were placed in a 500 mL eggplant flask. Iodine monochloride (2.5 mL) was added dropwise at room temperature, and then the mixture was stirred at 40°C. Every 2 hours, iodine monochloride (0.5 mL) was added dropwise to the reaction system, and a total of 4.5 mL of iodine monochloride was added. After all the monochloride elements were added dropwise, the mixture was stirred for another 1 hour and 30 minutes, and then returned to room temperature. Next, a saturated aqueous solution of sodium thiosulfate (20 mL) was added to the eggplant flask, and the organic layer was extracted with dichloromethane, the extracted organic layer was washed with water and saline, the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated with a rotary evaporator. The compound obtained after concentration 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 the abbreviation for dichloromethane.

[0391] In a 5mL vial, 1,4-dichloro-2,5-difluoro-3,6-diiodobenzene (435mg, 1.0mmol), copper cyanide (360mg, 4.0mmol), and DMF (5mL) were placed and heated and stirred at 150°C. After 1 hour and 30 minutes, the reaction solution was cooled to room temperature and poured into 10mL of ammonia water. Next, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and saline, and the washed organic layer was dried with magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after the removal under reduced pressure was purified by silica gel column chromatography to obtain 1,4-dicyano-2,5-dichloro-3,6-difluorobenzene (160mg). DMF is an abbreviation for N,N-dimethylformamide.

[0392] [ka]

[0393] 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 placed in a 500 mL three-neck flask and stirred at 80° C. for 4 hours. After stirring, the reaction solution was allowed to cool to room temperature, and the organic layer was extracted with toluene, the extracted organic layer was washed with water and saline, and the washed organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain 3',6'-difluoro-[1,1':4',1''-terphenyl]-2',5'-dicarbonitrile (18.8 g, 59.6 mmol). The structure of the purified compound was identified by ASAP / MS. ASAP / MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0394] [ka]

[0395] In a nitrogen atmosphere, 12H-benzo[4,5]thieno[2,3-a]carbazole (2.87 g, 110.5 mmol) and DMF (30 mL) were placed in a 200 mL flask. After cooling the flask to 0°C, sodium hydride (0.44 g, 10.5 mmol) was added and stirred for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1''-terphenyl]-2',5'-dicarbonitrile (1.58 g, 5.0 mmol) was added to the flask, and the mixture was 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 obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography, and then suspended and washed with methanol and dimethoxyethane to obtain the target compound A1 (2.82 g, 3.43 mmol). The structure of compound A1 was identified by LC / MS, which stands for Liquid Chromatography-Mass spectrometry.

[0396] Synthesis Example 2 The synthesis method of compound A2 is described below.

[0397] [ka]

[0398] In a nitrogen atmosphere, 12H-benzofluoro[2,3-a]carbazole (2.70 g, 10.5 mmol) and DMF (30 mL) were placed in a 300 mL flask. After cooling the flask to 0°C, sodium hydride (0.44 g, 10.5 mmol) was added and stirred for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1''-terphenyl]-2',5'-dicarbonitrile (1.58 g, 5.0 mmol) was added to the flask, 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 obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography, and then suspended and washed 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.

[0399] Synthesis Example 3 The synthesis method of compound A3 is described below.

[0400] [ka]

[0401] In a nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (2.87 g, 10.5 mmol) and DMF (52 mL) were placed in a 300 mL flask. After cooling the flask to 0°C, sodium hydride (0.44 g, 10.5 mmol) was added and stirred for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1''-terphenyl]-2',5'-dicarbonitrile (1.58 g, 5.0 mmol) was added to the flask, 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 obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography, and then suspended and washed 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.

[0402] Synthesis Example 4 The synthesis method of compound A4 is described below.

[0403] [ka]

[0404] Under a nitrogen atmosphere, tetrafluoroterephthalonitrile (25 g, 125 mmol), 1,4-dioxane 625 mL, and water 400 mL were placed in a 2000 mL three-neck flask. Next, 13 mL of 30% by mass ammonia water was placed in the three-neck flask and heated and stirred at 80° C. for 10 hours. After heating and stirring, the temperature was returned to room temperature (25° C.). The solvent was removed using an evaporator, and the obtained solid was purified by silica gel column chromatography to obtain 24 g of a white solid. This white solid was analyzed by GC-MS (Gas Chromatograph Mass Spectometer) and identified as compound M41 (yield 98%).

[0405] In a nitrogen atmosphere, compound M41 (10 g, 51 mmol), iodine (26 g, 102 mmol) and acetonitrile 100 mL were placed in a 200 mL three-neck flask. Next, tert-butyl nitrite (t-BuONO) (10 g, 102 mmol) was placed in the three-neck flask and stirred at 25° C. for 8 hours. After stirring, 50 mL of saturated aqueous sodium hydrogen sulfite solution was added to the reaction solution to extract the organic layer. The solvent was removed from the resulting solution using a rotary evaporator, and the solid was purified by silica gel column chromatography to obtain 8.4 g of a white solid. This white solid was analyzed by GC-MS and identified as compound M42 (yield 54%).

[0406] [ka]

[0407] Under a nitrogen atmosphere, the compound M42 (8.4 g, 27 mmol), tributylphenyltin (10 g, 27 mmol), toluene (90 mL), and Pd(PPh3)4 (1.6 g, 1.4 mmol) were added, and the mixture was heated under reflux and stirred for 8 hours. After the reaction was completed, the reaction solution was purified by silica gel column chromatography to obtain 5.2 g of a white solid, which was identified as compound M43 (yield 75%) by GC-MS analysis.

[0408] [ka]

[0409] Under a nitrogen atmosphere, 12H-Benzofuro[2,3-a]carbazole (1.74 g, 6.78 mmol), sodium hydride (0.27 g, 6.78 mmol) and 30 mL of DMF were placed in a 200 mL three-neck flask and stirred at room temperature (25° C.) for 30 minutes. Next, compound M43 (0.5 g, 1.94 mmol) was placed in the three-neck flask and stirred at 80° C. for 4 hours. The reaction mixture was then added to 50 mL of saturated aqueous ammonium chloride solution, and the precipitated solid was purified by silica gel column chromatography to obtain 1.0 g of a yellow solid. This yellow solid was analyzed by ASAP-MS and identified as compound A4 (yield 55%). ASAP-MS is synonymous with ASAP / MS.

[0410] Synthesis Example 5 The synthesis method of compound A5 is described below.

[0411] [ka]

[0412] In a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (50 g, 184 mmol), chlorotrimethylsilane (60 g, 552 mmol), and THF (200 mL) were placed in a 1000 mL three-neck flask. The materials in the three-neck flask were cooled to -78 ° C in a dry ice / acetone bath, and then 230 ml of lithium diisopropylamide (2 M, THF solution) was added dropwise. The mixture was stirred at -78 ° C for 2 hours, then returned to room temperature and stirred for another 2 hours. After stirring, water (200 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained intermediate a (73 g, 175 mmol, yield 95%) was used in the next reaction without purification. Chlorotrimethylsilane may be abbreviated as TMS-Cl. In the chemical formula of intermediate a, TMS is a trimethylsilyl group, and LDA is an abbreviation for lithium diisopropyl amide.

[0413] Under a nitrogen atmosphere, intermediate a (73 g, 175 mmol) and dichloromethane (200 mL) were placed in a 1000 mL eggplant 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 returned to room temperature, saturated aqueous sodium hydrogen sulfite solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and saline, the washed organic layer was dried over magnesium sulfate, and the dried organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate b (65 g, 124 mmol, yield 71%).

[0414] 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 placed in a 500 mL three-neck flask and stirred at 80° C. for 4 hours. After stirring, the reaction solution was allowed to cool to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, and the washed organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate c (10 g, 24 mmol, yield 56%). The structure of the purified compound was identified by ASAP / MS. ASAP / MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0415] Under a nitrogen atmosphere, intermediate c (10 g, 24 mmol), copper cyanide (10.6 g, 118 mmol), and DMF (15 mL) were placed in a 200 mL three-neck flask and heated and stirred at 150 ° C for 8 hours. After stirring, the mixture was cooled to room temperature, and the reaction solution was poured into 10 mL of ammonia water. Next, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and saline, and the washed organic layer was dried with magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after the reduced pressure removal was purified by silica gel column chromatography to obtain intermediate d (5.8 g, 18.34 mmol, yield 78%). DMF is an abbreviation for N,N-dimethylformamide.

[0416] Under a nitrogen atmosphere, intermediate d (1.0 g, 3.2 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (1.9 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol) and 30 mL of DMF were placed in a 100 mL three-neck flask and stirred at 120° C. for 6 hours. After stirring, the precipitated solid was filtered 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.

[0417] Synthesis Example 6 The synthesis method of compound A6 is described below.

[0418] [ka]

[0419] 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 placed in a 500 mL three-neck flask and stirred at 80 ° C for 6 hours. After stirring, the reaction solution was allowed to cool to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, and the washed organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate e (12.6 g, 29 mmol, yield 51%). The structure of the purified compound was identified by ASAP / MS.

[0420] Under a nitrogen atmosphere, intermediate e (12.6 g, 29 mmol), copper cyanide (13 g, 145 mmol), and DMF (20 mL) were placed in a 200 mL three-neck flask and heated and stirred at 150 ° C for 8 hours. After stirring, the mixture was cooled to room temperature and the reaction solution was poured into 10 mL of ammonia water. Next, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and saline, and the washed organic layer was dried with magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after removal under reduced pressure was purified by silica gel column chromatography to obtain intermediate f (6.2 g, 19.1 mmol, yield 66%).

[0421] Under a nitrogen atmosphere, intermediate f (1.5 g, 4.6 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (2.8 g, 10.1 mmol), potassium carbonate (1.9 g, 13.8 mmol) and 30 mL of DMF were placed in a 100 mL three-neck flask and stirred at 120°C for 6 hours. After stirring, the precipitated solid was filtered 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.

[0422] Synthesis Example 7 The synthesis method of compound A7 is described below.

[0423] [ka]

[0424] Under a nitrogen atmosphere, 4-bromodibenzothiophene (13.2 g, 50 mmol), 2-chloro-4,5-dimethylaniline (9.4 g, 60 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.45 g, 0.5 mmol), tri-tert-butylphosphonium 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-neck flask, and 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 obtain intermediate g (15 g, 44.5 mmol, yield 89%). The purified compound was identified as intermediate g by GC-MS analysis.

[0425] 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-neck 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 obtain intermediate h (12 g, 40.5 mmol, 91% yield). The purified compound was identified as intermediate h by GC-MS analysis.

[0426] Under a nitrogen atmosphere, intermediate d (1.0 g, 3.2 mmol), intermediate h (2.1 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol) and 30 mL of DMF were placed in a 100 mL three-neck flask and stirred at 120° C. for 4 hours. The precipitated solid was collected by filtration and purified by silica gel column chromatography to obtain compound A7 (1.5 g, 1.7 mmol, yield 54%). The obtained compound was identified as compound A7 by ASAP-MS analysis.

[0427] Synthesis Example 8 The synthesis method of compound A8 is described below.

[0428] [ka]

[0429] In a nitrogen atmosphere, 3-bromodibenzothiophene (26.3 g, 100 mmol), chlorotrimethylsilane (33 g, 300 mmol), and THF (150 mL) were placed in a 500 mL three-neck flask. The materials in the three-neck flask were cooled to -78 ° C in a dry ice / acetone bath, and then 125 mL of lithium diisopropylamide (2 M, THF solution) was added dropwise. The mixture was stirred at -78 ° C for 2 hours, then returned to room temperature and stirred for another 2 hours. After stirring, water (100 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, followed by 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 returned to room temperature, saturated aqueous sodium hydrogen sulfite solution (100 mL) was added, the organic layer was extracted with dichloromethane, the extracted organic layer was washed with water and saline, the washed organic layer was dried over magnesium sulfate, and the dried organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate i (28 g, 72 mmol, yield 72%).

[0430] Under a nitrogen atmosphere, 4-bromodibenzothiophene (13.2 g, 50 mmol), copper (I) oxide (0.1 g, 0.66 mmol), aqueous ammonia (100 ml, 30%) and NMP (N-methylpyrrolidone) (100 ml) were placed in a 500 ml three-neck flask and stirred at 80° C. for 12 hours. After stirring, the mixture was returned to room temperature, and the organic layer was extracted with 100 ml of ion-exchanged water and diethyl ether. The organic layer extracted was washed with water and saline, and the washed organic layer was dried over magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate j (9.0 g, 45 mmol, yield 90%).

[0431] Under a nitrogen atmosphere, intermediate i (17.5 g, 45 mmol), intermediate j (9.0 g, 45 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.8 g, 0.9 mmol), Xantphos (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-neck flask, heated and stirred at 100 ° C for 8 hours, and cooled to room temperature (25 ° C) after stirring. The reaction solution was purified by silica gel column chromatography to obtain intermediate k (9.5 g, 20.7 mmol, yield 46%). The purified compound was identified as intermediate k by GC-MS analysis.

[0432] 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-neck flask, and the mixture was stirred at 160°C for 10 hours, and then cooled to room temperature (25°C). The precipitated solid was collected by filtration and washed with acetone to obtain intermediate L (6.9 g, 18.2 mmol, 88% yield). The compound after washing was identified as intermediate L by GC-MS analysis.

[0433] 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 placed in a 100 mL three-neck flask and stirred at 140° C. for 4 hours. After stirring, the precipitated solid was filtered and purified by silica gel column chromatography to obtain compound A8 (2.3 g, 2.2 mmol, yield 69%). The obtained compound was identified as compound A8 by ASAP-MS analysis.

[0434] Synthesis Example 9 The synthesis method of compound A9 is described below.

[0435] [ka]

[0436] In a nitrogen atmosphere, 2,4,6-trifluoro-1,1'-biphenyl (10g, 48mmol), chlorotrimethylsilane (17g, 144mmol), and THF (50mL) were placed in a 200mL three-neck flask. The materials in the three-neck flask were cooled to -78°C in a dry ice / acetone bath, and then 60mL of lithium diisopropylamide (2M, THF solution) was added dropwise. The mixture was stirred at -78°C for 2 hours, then returned to room temperature and stirred for another 2 hours. After stirring, water (50mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained intermediate n (15g, 44mmol, 92% yield) was used in the next reaction without purification. Chlorotrimethylsilane may be abbreviated as TMS-Cl. In the chemical formula of intermediate n, TMS is a trimethylsilyl group, and LDA is an abbreviation for lithium diisopropyl amide.

[0437] Under a nitrogen atmosphere, intermediate n (15 g, 44 mmol) and dichloromethane (100 mL) were placed in a 500 mL eggplant 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 returned to room temperature, saturated aqueous sodium hydrogen sulfite solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and saline, the washed organic layer was dried over magnesium sulfate, and the dried organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate o (10 g, 121 mmol, yield 48%).

[0438] 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 placed in a 200 mL three-neck flask and heated and stirred at 150 ° C for 8 hours. After stirring, the mixture was cooled to room temperature and the reaction solution was poured into 30 mL of ammonia water. Next, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and saline, and the washed organic layer was dried with magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after removal under reduced pressure was purified by silica gel column chromatography to obtain intermediate p (1.8 g, 7.1 mmol, yield 34%).

[0439] In a nitrogen atmosphere, 12H-[1]Benzothieno[2,3-a]carbazole (3.0 g, 11 mmol) and DMF (20 mL) were placed in 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 mixture was warmed to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain compound A9 (1.6 g, 1.60 mmol, 50% yield). The obtained compound was identified as compound A9 by ASAP-MS analysis.

[0440] Synthesis Example 10 The synthesis method of compound A10 is described below.

[0441] [ka]

[0442] In 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 of xylene were placed in a 300 ml three-neck flask and stirred at 150°C for 10 hours. After stirring, the reaction solution was allowed to cool to room temperature, and the organic layer was extracted with ethyl acetate, the extracted organic layer was washed with water and saline, and the washed organic layer was concentrated with a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate m (7.2 g, 23 mmol, yield 37%). The structure of the purified compound was identified as intermediate m by ASAP / MS. ASAP / MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry. P(Cy)3 is an abbreviation for tricyclohexylphosphine.

[0443] In a nitrogen atmosphere, 12H-[1]Benzothieno[2,3-a]carbazole (3.0 g, 11 mmol) and DMF (20 mL) were placed in 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 mixture was warmed to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain compound A10 (2.6 g, 3.16 mmol, 71% yield). The obtained compound was identified as compound A10 by ASAP-MS analysis.

[0444] (Comparative Synthesis Example 1) The synthesis method of the comparative compound Ref-1 is described below.

[0445] [ka]

[0446] In a nitrogen atmosphere, 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole (2.97 g, 10.5 mmol) and DMF (30 mL) were placed in a 300 mL flask. After cooling the flask to 0°C, sodium hydride (0.44 g, 10.5 mmol) was added and stirred for 10 minutes. After stirring, 3',6'-difluoro-[1,1':4',1''-terphenyl]-2',5'-dicarbonitrile (1.58 g, 5.0 mmol) was added to the flask, 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 obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography, and then suspended and washed 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.

[0447] (Comparative Synthesis Example 2) The synthesis method of the comparative compound Ref-2 is described below.

[0448] [ka]

[0449] 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 placed in a 200 mL flask. After cooling the flask to 0°C, sodium hydride (0.28 g, 7.1 mmol) was added and stirred for 30 minutes. After stirring, intermediate d (1.00 g, 3.2 mmol) was added to the flask, and the mixture was warmed to room temperature and stirred for 2 hours. After stirring, 20 mL each of water and methanol were added to the flask, and the obtained solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain comparative compound Ref-2 (0.9 g, 1.00 mmol, yield 34%). The obtained compound was identified as comparative compound Ref-2 by ASAP-MS analysis. [Explanation of symbols]

[0450] Reference Signs List 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 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): However, 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, D's are the same or different, Each R is independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms, With the proviso that at least one R is a substituent, At least one R 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, R's are the same or different, The sum of the number of R substituents and the number of groups represented by the following general formula (12) or (13) is 3 or 4. 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 (R in the general formula (11) １ ~R ８ each independently represents a hydrogen atom, a halogen atom, or a substituent, R in the general formula (12) １１ ~R １８ are each 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 set of １７ and R １８ any one or more of the pairs of R in the general formula (13) １１１ ~R １１８ are each 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 set of １１７ and R １１８ any one or more of the pairs of R as a Substituent １ ~R ８ , R as a substituent １１ ~R １８ and R as a substituent １１１ ~R １１８ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, In the general formula (12) and the general formula (13), A, B, and C each independently represent a ring structure selected from the group consisting of ring structures represented by the following general formula (14), general formula (15), and general formula (16), The ring structure A, the ring structure B and the ring structure C are condensed with an 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, the ring structures A are the same or different from each other, When px is 2, 3 or 4, the multiple ring structures B are the same or different from each other, When py is 2, 3 or 4, the ring structures C are the same or different from each other, provided that at least one D is a group represented by the general formula (12) in which p is 2, 3, or 4, and which contains, as the ring structure A, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), or is a group represented by the general formula (13) in which at least one of px and py is 2, 3, or 4, and which contains, as the ring structure B or ring structure C, any ring structure selected from the group consisting of ring structures represented by the following general formulae (15) and (16), In the general formulas (11) to (13), * indicates the bonding position to the benzene ring in the general formula (1). 【Chemistry 5】 (In the general formula (14), R １９ and R ２０ are each independently a hydrogen atom, a halogen atom or a substituent, or R １９ and R ２０ are bonded to each other to form a ring, In the general formula (15) and the general formula (16), X １ and X ２ are each independently NR １２０ , a sulfur atom, or an oxygen atom; R １２０ is a hydrogen atom, a halogen atom or a substitution, R as a Substituent １９ , R ２０ and R １２０ each independently represents R as a substituent １ ~R ８ (Same meaning as above.)

2. the sum of the number of R which is a substituent and the number of groups represented by the general formula (12) or (13) is 4; The compound of claim 1.

3. The compound represented by the general formula (1) is represented by the following general formula (110), general formula (120) or general formula (130): A compound according to claim 1 or claim 2. 【Chemistry 6】 (In the general formula (110), general formula (120), and general formula (130), D, m, R, and n are respectively defined as D, m, R, and n in the general formula (1).)

4. 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): A compound according to any one of claims 1 to 3. 【Chemistry 7】 (In the general formulae (111) and (112), D １１ is a group represented by the general formula (12) or (13), R １２１ ~R １２３ are each independently defined as R in the general formula (1), provided that R １２１ ~R １２３ At least one of the substituents is a substituent. １２１ ~R １２３ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 8】 (In the general formulae (113) to (116), D １１ and D. １２ Each independently has the same meaning as D in the general formula (1), provided that D １１ and D. １２ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ and R １２２ are each independently defined as R in the general formula (1), provided that R １２１ and R １２２ At least one of the substituents is a substituent, １２１ and R １２２ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 9】 (In the general formulae (117) and (118), D １１ ~D １３ Each independently has the same meaning as D in the general formula (1), provided that D １１ ~D １３ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ is a substituent, and R as a substituent １２１ has the same meaning as R as the substituent in the general formula (1).

5. 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): A compound according to any one of claims 1 to 3. 【Chemistry 10】 (In the general formulae (121) to (123), D １１ is a group represented by the general formula (12) or (13), R １２１ ~R １２３ are each independently defined as R in the general formula (1), provided that R １２１ ~R １２３ At least one of the substituents is a substituent. １２１ ~R １２３ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 11】 (In the general formulae (124) to (126), D １１ and D. １２ Each independently has the same meaning as D in the general formula (1), provided that D １１ and D. １２ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ and R １２２ are each independently defined as R in the general formula (1), provided that R １２１ and R １２２ At least one of the substituents is a substituent, １２１ and R １２２ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 12】 (In the general formulae (127) to (129), D １１ ~D １３ Each independently has the same meaning as D in the general formula (1), provided that D １１ ~D １３ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ is a substituent, and R as a substituent １２１ has the same meaning as R as the substituent in the general formula (1).

6. 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): A compound according to any one of claims 1 to 3. 【Chemistry 13】 (In the general formula (131), D １１ is a group represented by the general formula (12) or (13), R １２１ ~R １２３ are each independently defined as R in the general formula (1), provided that R １２１ ~R １２３ At least one of the substituents is a substituent, １２１ ~R １２３ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 14】 (In the general formulae (132) to (134), D １１ and D. １２ Each independently has the same meaning as D in the general formula (1), provided that D １１ and D. １２ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ and R １２２ are each independently defined as R in the general formula (1), provided that R １２１ and R １２２ At least one of the substituents is a substituent. １２１ and R １２２ has the same meaning as R as the substituent in the general formula (1). 【Chemistry 15】 (In the general formula (135), D １１ ~D １３ Each independently has the same meaning as D in the general formula (1), provided that D １１ ~D １３ At least one of the groups is a group represented by general formula (12) or general formula (13), R １２１ is a substituent, and R as a substituent １２１ has the same meaning as R as the substituent in the general formula (1).

7. 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 set of １７ and R １８ None of the pairs are 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 set of １１７ and R １１８ None of the pairs of A compound according to any one of claims 1 to 6.

8. Having at least one group represented by the general formula (12), A compound according to any one of claims 1 to 7.

9. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E) and (12F): A compound according to any one of claims 1 to 8. 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R １１ ~R １８ each independently represents R in the general formula (12). １１ ~R １８ is synonymous with R １９ and R ２０ each independently represents R in the general formula (14). １９ and R ２０ is synonymous with X １ is X in the general formula (15). １ is synonymous with In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), * indicates the bonding position with the benzene ring in the general formula (1).

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

11. X １ is an oxygen atom or a sulfur atom; A compound according to any one of claims 1 to 10.

12. R as a Substituent １ ~R ８ , R as a substituent １１ ~R １８ and R as a substituent １１１ ~R １１８ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; A compound according to any one of claims 1 to 11.

13. R as a Substituent １ ~R ８ , R as a substituent １１ ~R １８ and R as a substituent １１１ ~R １１８ are each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; 13. A compound according to any one of claims 1 to 12.

14. R as a Substituent １ ~R ８ , R as a substituent １１ ~R １８ and R as a substituent １１１ ~R １１８ are each independently an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms; A compound according to any one of claims 1 to 11.

15. R as a Substituent １ ~R ８ , R as a substituent １１ ~R １８ and R as a substituent １１１ ~R １１８ are each independently an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; A compound according to any one of claims 1 to 11.

16. Each R is independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; 16. A compound according to any one of claims 1 to 15.

17. Each R is independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heteroaryl group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms; an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted arylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms; 16. A compound according to any one of claims 1 to 15.

18. Each R is independently a hydrogen atom, a halogen atom, or a substituent; Each R as a substituent is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heteroaryl group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; 16. A compound according to any one of claims 1 to 15.

19. Contains a compound according to any one of claims 1 to 18 Materials for organic electroluminescence devices.

20. An anode, a cathode, and an organic layer; The organic layer comprises a compound according to any one of claims 1 to 18 as a first compound. Organic electroluminescent element.

21. The organic electroluminescence device according to claim 20, The organic layer has at least one light-emitting layer, the light-emitting layer comprises the first compound; Organic electroluminescent element.

22. 22. An electronic device comprising the organic electroluminescence element according to claim 20 or 21.

Images