Electron barrier material, organic semiconductor element and compound

Abstract

This compound represented by a general formula is useful as an electron barrier material. R1 through R5 are a deuterium atom, a substituent other than a cyano group; n1, n3, n5 are 0-4; n2 is 0-3; n4 is 0-2; X is O or S; and Ar is a monocyclic arylene group or a monocyclic heteroarylene group.

Description

Electron barrier material, organic semiconductor device and compound

[0001] The present invention relates to a compound useful as an electron blocking material and an organic semiconductor device using the compound.

[0002] Research into improving the performance of organic semiconductor devices such as organic electroluminescence devices (organic EL devices) is actively being conducted. For example, to improve the device life and driving voltage of organic electroluminescence devices, it is desirable to improve the functionality of materials involved in charge transport, such as electron transport materials, hole transport materials, electron blocking materials, and hole blocking materials, and development and improvement of these materials is also being promoted. For example, an electron blocking material is a material for the electron blocking layer that is provided between the light-emitting layer and the hole transport layer and functions to prevent electrons present in the light-emitting layer from escaping from the light-emitting layer to the hole transport layer and to transport holes from the hole transport layer to the light-emitting layer. The use of an excellent electron blocking material improves the probability of recombination of electrons and holes in the light-emitting layer, ultimately leading to an extension of the device life. Various compounds have been proposed as electron blocking materials, and for example, Patent Document 1 proposes a compound having the following structure:

[0003]

[0004] WO2010 / 140482

[0005] However, organic electroluminescence devices using the above-mentioned compounds as electron-blocking materials have room for improvement in terms of device life. Therefore, the present inventors have conducted extensive research to provide an electron-blocking material that can extend the device life when used in organic electroluminescence devices.

[0006] As a result of extensive research, the present inventors have found that compounds having a specific structure function as excellent electron-blocking materials. The present invention has been provided based on this finding, and specifically has the following configurations: [1] An electron-blocking material containing a compound represented by the following general formula (1): [In the formula, R １ ~R ５ R each independently represents a deuterium atom or a substituent not containing a cyano group.１ ~R ５ is another R １ ~R ５ Alternatively, the group does not bond with Ar to form a cyclic structure, but the adjacent R ３ may bond to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2. X represents an oxygen atom or a sulfur atom. Ar represents a monocyclic arylene group or a monocyclic heteroarylene group, and the monocyclic arylene group and the monocyclic heteroarylene group may be substituted with a deuterium atom or a substituent not containing a cyano group.] [2] The electron-barrier material according to [1], wherein the compound has a structure represented by the following general formula (2A): [In the formula, R １ ~R ６ R each independently represents a deuterium atom or a substituent not containing a cyano group. １ ~R ６ is another R １ ~R ６ Although they do not bond to form a ring structure, adjacent R ３ may bond to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. X represents an oxygen atom or a sulfur atom.] [3] The electron-barrier material according to [1], wherein the compound has a structure represented by the following general formula (2B): [In the formula, R １ ~R ６ R each independently represents a deuterium atom or a substituent not containing a cyano group. １ ~R ６ is another R １ ~R ６ Although they do not bond to form a ring structure, adjacent R ３may be bonded to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. X represents an oxygen atom or a sulfur atom.] [4] The electron-barrier material according to [1], wherein the compound has a structure represented by the following general formula (3): [In the formula, R １ ~R ６ R each independently represents a deuterium atom or a substituent not containing a cyano group. １ ~R ６ is another R １ ~R ６ Although they do not bond to form a ring structure, adjacent R ３ may bond with each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. However, n1 + n3 + n4 + n5 is 1 or more. R １ and R ３ ~R ５ One or two of these represent an optionally deuterated alkyl group or a phenyl group optionally substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom.] [5] The electron-blocking material according to any one of [2] to [4], wherein n1, n2, and n6 are 0. [6] The electron-blocking material according to any one of [1] to [5], wherein n3 to n5 are each independently 0 or 1. [7] The electron-blocking material according to [1], having any one of the following structures: [8] The electron-blocking material according to any one of [1] to [7], which is used in combination with a compound represented by the following general formula (G): [In general formula (G), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other as a single bond to form a pyrrole ring.] In one embodiment of the present invention, X １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ In one embodiment of the present invention, any of X １ is a boron atom, and X ２ is a nitrogen atom, and R ７ and R ８ , R １７ and R １８ are bonded to each other to form a cyclic structure containing a boron atom, the cyclic structure is a 5- to 7-membered ring, and when it is a 6-membered ring, R ７ and R ８ , R １７ and R １８ are bonded to each other to form -B(R ３２ )-, -CO-, -CS- or -N(R ２７ )- is formed. ２７represents a hydrogen atom, a deuterium atom, or a substituent. [9] An organic semiconductor device comprising the electron blocking material according to any one of [1] to [7].

[10] The organic semiconductor device according to [9], which is an organic electroluminescence device having an anode, a cathode, and at least two organic layers between the anode and the cathode, the organic layers including an electron blocking layer containing the electron blocking material and an emitting layer.

[11] The organic semiconductor device according to

[10] , wherein the emitting layer contains a host material and a delayed fluorescent material.

[12] The organic semiconductor device according to

[10] , wherein the emitting layer contains a host material, a delayed fluorescent material, and a fluorescent material, and the amount of light emitted from the device is the largest from the fluorescent material.

[13] The organic semiconductor device according to any one of

[10] to

[12] , wherein the emitting layer is adjacent to the electron blocking layer.

[14] The organic semiconductor device according to any one of

[10] to

[13] , wherein the emitting layer contains a compound represented by general formula (G).

[15] The organic semiconductor device according to any one of

[10] to

[14] , wherein the light-emitting layer contains a compound represented by the following general formula (4): [In general formula (4), R ２１ ~R ２３ one of the groups represents a cyano group or a group represented by the following general formula (5), and R ２１ ~R ２３ The remaining two and R ２４ and R ２５ At least one of R represents a group represented by the following general formula (6): ２１ ~R ２５ The remainder represents a hydrogen atom or a substituent (provided that the substituent referred to here is not a cyano group, a group represented by the following general formula (5), or a group represented by the following general formula (6)). [In the general formula (5), L １ represents a single bond or a divalent linking group, R ３１ and R ３２ each independently represents a hydrogen atom or a substituent, and * represents a bonding position. [In general formula (6), L ２ represents a single bond or a divalent linking group, R ３３ and R ３４each independently represents a hydrogen atom or a substituent, and * represents a bonding position.]

[16] A compound represented by the general formula (3), provided that when n3 + n4 + n5 is 0, R １ is not an unsubstituted phenyl group.

[0007] The compound represented by general formula (1) is useful as an electron blocking material and can be effectively used in organic semiconductor devices. For example, by using the compound of the present invention in the electron blocking layer of an organic electroluminescence device, the device life can be extended.

[0008] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this application, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, in this application, "consisting of" means that the compound consists only of what is described before "consisting of" and does not include anything else. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２ H, deuterium (D). In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted location. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the expressions "substituted or unsubstituted" and "optionally substituted" mean that a hydrogen atom may be substituted with a deuterium atom or a substituent. In addition, "transparent" in the present invention refers to a visible light transmittance of 50% or more, preferably 80% or more, more preferably 90% or more, and even more preferably 99% or more. Visible light transmittance can be measured using an ultraviolet-visible spectrophotometer.

[0009] (Compound Represented by General Formula (1)) In the present invention, a compound represented by the following general formula (1) is used.

[0010] In general formula (1), R １ ~R ５ Each independently represents a deuterium atom or a substituent not containing a cyano group. １ ~R ５ In a preferred embodiment of the present invention, the substituents R １ ~R ５ In a preferred embodiment of the present invention, the substituents R １ ~R ５ In one embodiment of the present invention, the substituents R １ ~R ５ In one embodiment of the present invention, the substituents R １ ~R ５Each of the substituents independently has a Hammett σp value in the range of -0.3 or more and less than 0. Here, the "Hammett σp value" was proposed by L. P. Hammett and quantifies the influence of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is a constant (σp) specific to a substituent in a para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of a benzene derivative without a substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative without a substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" and the numerical values ​​of each substituent in the present invention, the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991) can be referred to. A group with a negative Hammett σp value tends to exhibit electron donating properties (donor properties), and a group with a positive Hammett σp value tends to exhibit electron withdrawing properties (acceptor properties). In one embodiment of the present invention, R １ ~R ５ are each independently a substituent having no unshared electron pair. １ ~R ５ are each independently a substituent having no π electrons.

[0011] In one aspect of the present invention, R １ ~R ５ are each independently one group or a combination of two or more groups selected from the group consisting of alkyl groups and aryl groups (for example, having 6 to 30 carbon atoms).

[0012] In one aspect of the present invention, R １ ~R ５ are each independently an alkyl group having 1 to 30 carbon atoms which may be substituted with an aryl group having 6 to 20 carbon atoms. １ ~R ５are each independently an aryl group having 6 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 30 carbon atoms. １ ~R ５ are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms. １ ~R ５ are each independently an unsubstituted aryl group having 6 to 20 carbon atoms.

[0013] R １ ~R ５ is another R １ ~R ５ Alternatively, the group does not bond with Ar to form a cyclic structure, but the adjacent R ３ may bond to each other to form a benzofuro skeleton or a benzothieno skeleton. Therefore, the dibenzofuran (three-ring structure) on the left side of general formula (1) is not fused with any further rings to form a structure of four or more rings. Furthermore, the benzofurocarbazole (five-ring structure), benzothienocarbazole (five-ring structure), bisbenzofurocarbazole (seven-ring structure), bisbenzothienocarbazole (seven-ring structure), etc. on the right side of general formula (1) are not fused with any further rings. It is preferable that the structure on the right side of general formula (1) is a five-ring structure. That is, in a preferred embodiment of the present invention, R ３ They do not bond to each other to form a ring structure.

[0014] In general formula (1), n1, n3, and n5 each independently represent an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2. In one embodiment of the present invention, n1 to n5 each independently represent an integer of 0 to 2. In one embodiment of the present invention, n1 is 0. In one embodiment of the present invention, n2 is 0. In one embodiment of the present invention, n3 is 0 or 1. In one embodiment of the present invention, n4 is 0 or 1. In one embodiment of the present invention, n5 is 0 or 1. In a preferred embodiment of the present invention, n3 + n4 + n5 is 1 or more. In a preferred embodiment of the present invention, n3 + n4 + n5 is 1. In a preferred embodiment of the present invention, n3 + n4 + n5 is 2. In a preferred embodiment of the present invention, n1, n2, n4, and n5 are 0, and n3 is 1. In a preferred embodiment of the present invention, n1 to n3 and n5 are 0, and n4 is 1. In a preferred embodiment of the present invention, n1 to n4 are 0, and n5 is 1. In a preferred embodiment of the present invention, n1, n2, and n4 are 0, and n3 and n5 are 1. In a preferred embodiment of the present invention, n1, n2, and n5 are 0, and n3 and n4 are 1.

[0015] In general formula (1), X represents an oxygen atom or a sulfur atom. In one embodiment of the present invention, X is a sulfur atom. In a preferred embodiment of the present invention, X is an oxygen atom. In general formula (1), a single bond extends downward and to the left from the ortho position of the benzene ring bonded to the right of X. This single bond may be bonded to any of positions 1 to 4 of the carbazole structure located to the right of Ar in general formula (1). Furthermore, X may also be bonded to any of positions 1 to 4 of the carbazole structure located to the right of Ar in general formula (1). However, the single bond and X are bonded to adjacent carbon atoms constituting the skeleton of the carbazole structure. Therefore, when the single bond is bonded to position 2, X is bonded to position 1 or 3. When the single bond is bonded to position 3, X is bonded to position 2 or 4. When the single bond is bonded to position 1, X is bonded to position 2. When the single bond is bonded to position 4, X is bonded to position 3. In general formula (1), X is written above the single bond, but general formula (1) also includes the structure of the following general formula (1′) in which the single bond is located below X.

[0016] As the benzofurocarbazol-9-yl group bonded to Ar in general formula (1), a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be used. Alternatively, a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be used. Alternatively, a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be used. As the benzothienocarbazol-9-yl group bonded to Ar in general formula (1), a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be used. A substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be employed. A substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be employed. A substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be employed. A substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be employed. A substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be employed. As the bisbenzofurocarbazol-9-yl group bonded to Ar in general formula (1), a substituted or unsubstituted bisbenzofuro[2,3-a:2',3'-f]carbazol-9-yl group can also be employed. A substituted or unsubstituted bisbenzofuro[3,2-a:3',2'-f]carbazol-9-yl group can also be employed. Alternatively, a substituted or unsubstituted bisbenzofuro[2,3-b:2',3'-e]carbazol-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzofuro[3,2-b:3',2'-e]carbazol-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzofuro[2,3-c:2',3'-d]carbazol-9-yl group can be used.A substituted or unsubstituted bisbenzofuro[3,2-c:3',2'-d]carbazol-9-yl group can also be used. As the bisbenzothienocarbazol-9-yl group bonded to Ar in general formula (1), a substituted or unsubstituted bisbenzothieno[2,3-a:2',3'-f]carbazol-9-yl group can also be used. A substituted or unsubstituted bisbenzothieno[3,2-a:3',2'-f]carbazol-9-yl group can also be used. A substituted or unsubstituted bisbenzothieno[2,3-b:2',3'-e]carbazol-9-yl group can also be used. A substituted or unsubstituted bisbenzothieno[3,2-b:3',2'-e]carbazol-9-yl group can also be used. Alternatively, a substituted or unsubstituted bisbenzothieno[2,3-c:2',3'-d]carbazol-9-yl group or a substituted or unsubstituted bisbenzothieno[3,2-c:3',2'-d]carbazol-9-yl group may be employed.

[0017] Specific examples of the substituted or unsubstituted benzofurocarbazol-9-yl group and the substituted or unsubstituted benzothienocarbazol-9-yl group bonded to Ar in general formula (1) are shown below. However, the structures that can be employed in the present invention are not limited to these specific examples. In this application, * indicates the bonding position. Ph indicates an unsubstituted phenyl group. In addition, in this application, a methyl group is represented by CH ３ Instead of writing it as CH, like the bottom left of D7. ３ The notation is omitted.

[0018] Compounds in which all hydrogen atoms of the above D1 to D64 have been replaced with deuterium atoms are exemplified herein as D1(D) to D64(D). Compounds in which only hydrogen atoms bonded to the alkyl groups of the above D7 to D18 and D37 to D48 have been replaced with deuterium atoms are exemplified herein as D7(R) to D18(R) and D37(R) to D48(R). Compounds in which only hydrogen atoms bonded to the phenyl groups of the above D19 to D30 and D49 to D60 have been replaced with deuterium atoms are exemplified herein as D19(Ph) to D30(Ph) and D49(Ph) to D60(Ph). In a preferred embodiment of the present invention, the substituted or unsubstituted benzofurocarbazol-9-yl group and the substituted or unsubstituted benzothienocarbazol-9-yl group bonded to Ar in general formula (1) are selected from D1 to D60, D1(D) to D60(D), D7(R) to D18(R), D37(R) to D48(R), D19(Ph) to D30(Ph), and D49(Ph) to D60(Ph), more preferably selected from D1 to D30, D1(D) to D30(D), D7(R) to D18(R), and D19(Ph) to D30(Ph). In a preferred embodiment of the present invention, the amine is selected from D7 to D30, D37 to D60, D7(D) to D30(D), D37(D) to D60(D), D7(R) to D18(R), D37(R) to D48(R), D19(Ph) to D30(Ph), and D49(Ph) to D60(Ph), more preferably from D19 to D30, D49 to D60, D19(D) to D30(D), D49(D) to D60(D), D19(Ph) to D30(Ph), and D49(Ph) to D60(Ph), and even more preferably from D19 to D30, D19(D) to D30(D), and D19(Ph) to D30(Ph).

[0019] In general formula (1), Ar represents a monocyclic arylene group or a monocyclic heteroarylene group. The monocyclic arylene group here refers to a non-fused phenylene group. Furthermore, the monocyclic heteroarylene group refers to an aromatic ring group having a non-fused single ring structure and containing a heteroatom as a ring skeleton-constituting atom. The monocyclic heteroarylene group preferably has 5 to 7 ring skeleton-constituting atoms, more preferably 5 or 6, and for example, a monocyclic heteroarylene group having 6 ring skeleton-constituting atoms can be used. Examples of heteroatoms constituting the ring skeleton of the monocyclic heteroarylene group include a nitrogen atom, an oxygen atom, and a sulfur atom, with a nitrogen atom being preferred. Examples of rings constituting the monocyclic heteroarylene group include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring. When the carbazole represented on the right side of general formula (1) is bonded to the 1-position of the monocyclic ring constituting Ar, the dibenzofuran represented on the left side of general formula (1) may be bonded to any position of the monocyclic ring constituting Ar. Preferably, dibenzofuran is bonded to the 3- or 4-position of the monocyclic ring constituting Ar. Particularly preferred is when dibenzofuran is bonded to the 3-position of the monocyclic ring constituting Ar (for example, when Ar is a substituted or unsubstituted 1,3-phenylene group), which is superior to when dibenzofuran is bonded to the 2- or 4-position.

[0020] The monocyclic arylene group and monocyclic heteroarylene group that Ar can take may each be substituted with a substituent that does not contain a deuterium atom or a cyano group. In a preferred embodiment of the present invention, a substituent having a Hammett σp value in the range of -0.3 to 0.3 is selected as the substituent. For details of the substituent having a Hammett σp value in the range of -0.3 to 0.3 and the preferred range, etc., see R １ ~R ５In one embodiment of the present invention, a group not having an unshared electron pair is selected as the substituent. In one embodiment of the present invention, a group not having π electrons is selected as the substituent. In a preferred embodiment of the present invention, one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms) and aryl groups (e.g., having 6 to 30 carbon atoms) is selected as the substituent. In a preferred embodiment of the present invention, an alkyl group having 1 to 30 carbon atoms is selected as the substituent. For the description and preferred range of the alkyl group, see R １ ~R ５ In a preferred embodiment of the present invention, Ar is a phenylene group optionally substituted with 1 to 4 alkyl groups having 1 to 20 carbon atoms, or a monocyclic heteroarylene group optionally substituted with 1 to 3 alkyl groups having 1 to 20 carbon atoms. In a preferred embodiment of the present invention, Ar is an unsubstituted phenylene group or an unsubstituted monocyclic heteroarylene group.

[0021] Specific examples of Ar in general formula (1) are shown below, but the structures that can be employed in the present invention should not be construed as being limited by these specific examples. t-Bu represents a tert-butyl group, and Ph represents an unsubstituted phenyl group.

[0022] Ar1(D) to Ar15(D) are examples of compounds in which all hydrogen atoms in Ar1 to Ar15 have been replaced with deuterium atoms. Ar2(R) to Ar9(R) are examples of compounds in which only the hydrogen atoms bonded to the alkyl groups in Ar2 to Ar9 have been replaced with deuterium atoms. Ar10(Ph) is an example of compounds in which only the hydrogen atoms bonded to the phenyl group in Ar10 have been replaced with deuterium atoms. In a preferred embodiment of the present invention, Ar in general formula (1) is selected from Ar1 to Ar9, Ar1(D) to Ar9(D), and Ar2(R) to Ar9(R), more preferably selected from Ar1 to Ar9. In a preferred embodiment of the present invention, Ar in general formula (1) is Ar1 or Ar1(D), more preferably Ar1.

[0023] The dibenzofuran depicted on the left side of general formula (1) may be bonded to Ar at any of the 1st to 4th positions. In a preferred embodiment of the present invention, the dibenzofuran is bonded to Ar at the 2nd position. In one embodiment of the present invention, the dibenzofuran is bonded to Ar at the 1st position. In one embodiment of the present invention, the dibenzofuran is bonded to Ar at the 3rd position. In one embodiment of the present invention, the dibenzofuran is bonded to Ar at the 4th position. The 1st to 4th positions of the dibenzofuran are as follows:

[0024] Specific examples of the dibenzofuryl group bonded to Ar in general formula (1) are shown below, but the structures that can be employed in the present invention are not to be construed as being limited by these specific examples.

[0025] Examples of compounds in which all hydrogen atoms of B1 to B12 have been replaced with deuterium atoms are exemplified herein as B1(D) to B12(D). Examples of compounds in which only the hydrogen atoms bonded to the alkyl groups of B2, B5, B8, and B11 have been replaced with deuterium atoms are exemplified herein as B2(R), B5(R), B8(R), and B11(R). Examples of compounds in which only the hydrogen atoms bonded to the phenyl groups of B3, B6, B9, and B12 have been replaced with deuterium atoms are exemplified herein as B3(Ph), B6(Ph), B9(Ph), and B12(Ph). In a preferred embodiment of the present invention, the dibenzofuryl group bonded to Ar in general formula (1) is selected from B1 to B3, B1(D) to B3(D), B2(R), and B3(Ph), more preferably selected from B1 to B3. In one embodiment of the present invention, the dibenzofuryl group bonded to Ar in general formula (1) is selected from B1, B4, B7, B10, B1(D), B4(D), B7(D), and B10(D), more preferably selected from B1, B4, B7, and B10.

[0026] The "alkyl group" in this application may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched moieties may be present in combination. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. In one embodiment of the present invention, the alkyl group has 1 to 4 carbon atoms. In one embodiment of the present invention, the alkyl group is a methyl group. In one embodiment of the present invention, the alkyl group is an isopropyl group. In one embodiment of the present invention, the alkyl group is a tert-butyl group. When multiple alkyl groups are present in the molecule represented by general formula (1), these alkyl groups may be the same or different. In one embodiment of the present invention, all alkyl groups in a molecule represented by general formula (1) are the same. The number of alkyl groups in a molecule represented by general formula (1) can be 0 or more, 1 or more, 2 or more, 4 or more, or 8 or more. The number of alkyl groups in a molecule represented by general formula (1) may be 20 or less, 10 or less, 5 or less, or 3 or less. The number of alkyl groups in a molecule represented by general formula (1) may be 0. Note that the number of alkyl groups here includes the number of alkyl groups substituted on the phenyl group. In this application, a "phenyl group optionally substituted with an alkyl group" means that at least one of the five hydrogen atoms present on the phenyl group may be substituted with an alkyl group. In one embodiment of the present invention, the phenyl group is substituted with 0 to 3 alkyl groups. For example, it is substituted with 0 to 2 alkyl groups. In one embodiment of the present invention, the phenyl group is not substituted with an alkyl group. The alkyl group substituted on the phenyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.Examples include a 4-methylphenyl group, a 3-methylphenyl group, a 3,5-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,3,4,5,6-heptamethylphenyl group, a 4-isopropylphenyl group, a 3-isopropylphenyl group, a 3,5-diisopropylphenyl group, a 4-tert-butylphenyl group, a 3-tert-butylphenyl group, and a 3,5-ditert-butylphenyl group. Further examples include groups in which all hydrogen atoms present in the alkyl substituents of these specific examples are substituted with deuterium atoms. Furthermore, examples include groups in which all hydrogen atoms present in these specific examples are substituted with deuterium atoms. In the present application, an "optionally deuterated alkyl group" means that at least one hydrogen atom of the alkyl group may be substituted with a deuterium atom. All hydrogen atoms of the alkyl group may be substituted with deuterium atoms. For example, an optionally deuterated methyl group includes CH. ３ , CDH ２ , CDs ２ H, CD ３ The "optionally deuterated alkyl group" is preferably an alkyl group that is not deuterated at all or an alkyl group in which all hydrogen atoms are substituted with deuterium atoms. In one embodiment of the present invention, an alkyl group that is not deuterated at all is selected as the "optionally deuterated alkyl group". In one embodiment of the present invention, an alkyl group in which all hydrogen atoms are substituted with deuterium atoms is selected as the "optionally deuterated alkyl group".

[0027] No cyano group is present in general formula (1). In a preferred embodiment of the present invention, general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In a preferred embodiment of the present invention, general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. The molecular weight of the compound represented by general formula (1) is 499 or more and preferably 700 or less, more preferably 600 or less, and may be, for example, 550 or less, or may be 530 or less.

[0028] A preferred example of the compound represented by general formula (1) is a compound represented by the following general formula (2A).

[0029] A preferred example of the compound represented by general formula (1) is a compound represented by the following general formula (2B).

[0030] R in general formula (2A) and general formula (2B) １ ~R ５ , n1 to n5, and X, the corresponding definitions and explanations of general formula (1) can be referred to. ６ The definition and explanation of R in general formula (1) １ ~R ５ The definitions and explanations of the formulas can be referred to. In the formulas (2A) and (2B), n6 is an integer of 0 to 3. n6 can be selected within the range of 0 to 2, or can be 0 or 1, and is preferably 0. In the formulas (2A) and (2B), n1 to n6 can each independently be selected within the range of 0 to 2, or can be 0 or 1. All of n1 to n6 may be 0. Particularly preferred among the structures represented by the formulas (2A) and (2B) are those in which (R ６ ) ｎ６ is a structure in which the phenylene group to which is bonded is a 1,3-phenylene group (metaphenylene group).

[0031] As a compound represented by general formula (1), a compound represented by the following general formula (3) can be particularly preferably exemplified.

[0032] In general formula (3), R １ ~R ６ R each independently represents a deuterium atom or a substituent not containing a cyano group. １ ~R ６ is another R １ ~R ６ Although they do not bond to form a ring structure, adjacent R ３may bond with each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. However, n1 + n3 + n4 + n5 is 1 or more. R １ and R ３ ~R ５ One or two of the R in the general formula (3) represent an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom. １ ~R ６ , n1 to n6 are defined and explained in R １ ~R ６ , n1 to n6 can be referred to in the definitions and explanations, but in general formula (3), n1 + n3 + n4 + n5 is 1 or more, and R １ and R ３ ~R ５ The only difference is that one or two of R represents an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom (hereinafter referred to as "phenyl group A"). １ and R ３ ~R ５ In one aspect of the invention, no more than three of R １ is a phenyl group A. In one aspect of the invention, only one R ３ is a phenyl group A. In one aspect of the invention, only one R ４ is a phenyl group A. In one aspect of the invention, only one R ５ is a phenyl group A. In one aspect of the invention, only one R ３ and one R ４ is a phenyl group A. In one aspect of the invention, only one R ３ and one R ５ is a phenyl group A. In one aspect of the invention, only one R ４ and one R ５ is a phenyl group A. In the present invention, two R ３ Only, two R ４Only one or two R ５ Only n may be a phenyl group A. When n3 + n4 + n5 is 0, R １ is preferably not an unsubstituted phenyl group. ３ ~R ５ At least one of R is a phenyl group A, and n3 + n4 + n5 is 1 or more. ３ ~R ５ At least one of the phenyl groups A is bonded to a meta position (the second position of the carbazole ring) with respect to the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole. ３ ~R ５ At least one of the phenyl groups A is bonded to the para position (the 3rd position of the carbazole ring) with respect to the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole. ３ ~R ５ The phenyl group A in R is bonded only to the meta position (the second position of the carbazole ring) as viewed from the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole. ３ ~R ５ The phenyl group A in R is bonded only to the para position (the 3rd position of the carbazole ring) with respect to the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole. ３ ~R ５ The phenyl group A in R is bonded only to the para position with respect to the bonding position of the oxygen atom constituting the ring skeleton of the benzofuro structure or the sulfur atom constituting the ring skeleton of the benzothieno structure. ３ ~R ５One phenyl group A is bonded at the para position relative to the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole, and the other is bonded at the para position relative to the bonding position of the oxygen atom constituting the ring skeleton of the benzofuro structure or the sulfur atom constituting the ring skeleton of the benzothieno structure. In one embodiment of the present invention, the phenyl group A is a phenyl group optionally substituted with an alkyl group which may be deuterated. In a preferred embodiment of the present invention, the phenyl group A is a phenyl group optionally substituted with a deuterium atom. In a particularly preferred embodiment of the present invention, the phenyl group A is an unsubstituted phenyl group. In general formula (3), n3 + n4 + n5 is an integer of 1 to 10, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, and even more preferably an integer of 1 to 4. In a preferred embodiment of the present invention, n3 + n4 + n5 is 1. In a preferred embodiment of the present invention, n3 + n4 + n5 is 2.

[0033] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. Using a coating method, it is possible to form a film even from compounds with relatively large molecular weights. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0034] The compound represented by general formula (1) preferably does not contain a metal atom or a boron atom. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, nitrogen, and oxygen atoms.

[0035] Specific examples of the compound represented by general formula (1) are listed below, but the compounds that can be used in the present invention should not be construed as being limited to these specific examples. Note that D in P6 to P14 represents a deuterium atom.

[0036] The following compounds can also be used as the compound represented by general formula (1).

[0037] The following compounds can also be used as the compound represented by general formula (1).

[0038] The following compounds can also be used as the compound represented by general formula (1).

[0039] The following compounds can also be used as the compound represented by general formula (1).

[0040] The following compounds can also be used as the compound represented by general formula (1).

[0041] The following compounds can also be used as the compound represented by general formula (1).

[0042] The following compounds can also be used as the compound represented by general formula (1).

[0043]

[0044] Compounds 1a to 47n in which all hydrogen atoms have been replaced with deuterium atoms are exemplified here as Compounds 1a(D) to 47n(D). Compounds 1a to 21d in which only the hydrogen atoms bonded to the phenyl groups have been replaced with deuterium atoms are exemplified here as Compounds 1a(Ph) to 21d(Ph). In the present invention, Compounds 1a to 21d can be cited as more preferred compounds than Compounds 22 and 23. In one aspect of the present invention, Compound na (n is an integer of 1 to 21, and Compound na herein refers to the group consisting of Compounds 1a, 2a, 3a, ... 21a) is selected. In a preferred aspect of the present invention, Compound nb (n is an integer of 1 to 21) is selected. In one aspect of the present invention, Compound nc (n is an integer of 1 to 21) is selected. In one aspect of the present invention, Compound nd (n is an integer of 1 to 21) is selected. In one aspect of the present invention, Compound nd is selected from Compounds 1a to 5d. In one aspect of the present invention, the compound is selected from compounds 7a to 9d. In one aspect of the present invention, the compound is selected from compounds 10a to 12d. In one aspect of the present invention, the compound is selected from compounds 13a to 15d. In one aspect of the present invention, the compound is selected from compounds 16a to 18d. In one aspect of the present invention, the compound is selected from compounds 19a to 21d. Furthermore, in the present invention, compounds 24a to 47n can be mentioned as more preferred compounds than compound 23, and compounds 24a to 27n can be mentioned as even more preferred compounds. In one aspect of the present invention, the compound is selected from compounds 24a to 24n. In one aspect of the present invention, the compound is selected from compounds 25a to 25n. In one aspect of the present invention, the compound is selected from compounds 26a to 26n. In one aspect of the present invention, the compound is selected from compounds 27a to 27n. In one aspect of the present invention, the compound is selected from 24a, 25a, 26a, 27a, 24f, 25f, 26f, and 27f.

[0045] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0046] This specification also discloses a compound represented by the following general formula (A) as a compound useful as an electron blocking material or a host material.

[0047] In general formula (A), X １ represents an oxygen atom or a sulfur atom. ２ is an oxygen atom, a sulfur atom, N(R ７ ) or C(R ８ ) (R ９ ) represents. １ ~R ６ Each independently represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in combination of two or more thereof. １ R is an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a combination of two or more groups. １ ~R ６ is another R １ ~R ６ Although they do not bond to form a ring structure, adjacent R ３ may bond with each other to form a benzofuro skeleton or a benzothieno skeleton. n1 represents an integer of 1 to 4, n3, n5, and n6 each independently represent an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2. In general formula (A), (R ５ ) ｎ５ and a benzene ring to which (R ４ ) ｎ４ The benzene ring to which is bonded is a single bond and X ２ However, the left-right positional relationship of these two bonds may be reversed. That is, in the above general formula (A), the single bond is on the left side, and X ２ The linking group via is shown on the right, but the single bond is on the right, X ２ The general formula (A) also includes a structure in which the linking group via

[0048] In a preferred embodiment of the present invention, X １ and X ２ In one aspect of the present invention, X１ and X ２ In a preferred embodiment of the present invention, X １ and X ２ are both oxygen atoms. In one aspect of the present invention, X １ and X ２ In one embodiment of the present invention, X １ is an oxygen atom, and X ２ is a sulfur atom. １ is a sulfur atom, and X ２ is an oxygen atom. In one aspect of the present invention, X １ is an oxygen atom, and X ２ is N (R ７ In one aspect of the present invention, X １ is an oxygen atom, and X ２ is C(R ８ ) (R ９ In a preferred embodiment of the present invention, X １ is an oxygen atom. In a preferred embodiment of the present invention, X ２ is an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0049] R １ ~R ６ are each independently one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group combining two or more thereof, and are preferably a deuterium atom, an alkyl group optionally substituted with a deuterium atom, or an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group combining two or more thereof. In one preferred embodiment of the present invention, R １ ~R ６are each independently a deuterium atom, or an aryl group which may be substituted with one atom or group selected from the group consisting of deuterium atoms and aryl groups, or a group in combination of two or more thereof. The number of carbon atoms in the alkyl group in the explanation of general formula (1) can be selected within the range of usually 1 to 40, preferably 1 to 15, more preferably 1 to 6, for example 1 to 3. The number of carbon atoms in the aryl group can be selected within the range of usually 6 to 30, preferably 6 to 18, more preferably 6 to 14, for example 6 to 10. In one embodiment of the present invention, R ３ In one embodiment of the present invention, R ３ They bond to each other to form a benzothieno skeleton. The benzofuro skeleton or the benzothieno skeleton may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in combination of two or more thereof. In one embodiment of the present invention, R ３ They do not bond to each other to form a ring structure.

[0050] At least one R １ is an aryl group optionally substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, more preferably a phenyl group optionally substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, and even more preferably a phenyl group optionally substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom and a phenyl group. In one embodiment of the present invention, such R １ is an unsubstituted aryl group or an aryl group in which all hydrogen atoms are substituted with deuterium atoms, and is preferably an unsubstituted phenyl group or a phenyl group in which all hydrogen atoms are substituted with deuterium atoms. １ In one embodiment of the present invention, only one of the two R １is an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a combination of two or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group. １ Specific examples of groups that can be taken by R include P1 to P14 above. １ is not to be construed as being limited by these specific examples. ５ ) ｎ５ When the group bonded to the right side of the benzene ring to which is bonded [the pentacyclic group on the right side of general formula (A)] is a benzofuro[3,2-a]carbazolyl group, R １ is not an unsubstituted phenyl group.

[0051] Among the compounds represented by general formula (A), for example, a compound represented by the following general formula (A1) can be preferably used.

[0052] In general formula (A1), X １ , X ２ , R １ ~R ６ , n1 to n6, the corresponding descriptions in the general formula (A) above can be referred to.

[0053] [Organic Semiconductor Device] The compound represented by general formula (1) can be preferably applied to an organic semiconductor device. For example, a CMOS (complementary metal oxide semiconductor) can be fabricated using the compound represented by general formula (1). In an embodiment of the present disclosure, an organic optical device such as an organic electroluminescence device or a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using the compound represented by general formula (1). In particular, the compound represented by general formula (1) of the present invention can be used in an organic light-emitting device such as an organic electroluminescence device (organic EL device). In particular, the compound represented by general formula (1) of the present invention can be effectively used as an electron-blocking material for an organic light-emitting device. In particular, the use of the compound represented by general formula (1) of the present invention in an electron-blocking layer can extend the device life.

[0054] An organic electroluminescent element has a structure including at least an anode, a cathode, and an organic layer formed between the anode and the cathode. The organic layer includes at least an emitting layer, and preferably includes one or more organic layers (particularly an electron blocking layer) in addition to the emitting layer. Examples of organic layers constituting an organic electroluminescent element include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, an exciton blocking layer, and a base layer for the emitting layer. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. Below, each component and each layer of the organic electroluminescent element will be described. Note that the description of the substrate and the emitting layer also applies to the substrate and the emitting layer of an organic photoluminescent element.

[0055] (Electron Blocking Layer) In a preferred embodiment of the present invention, the compound represented by general formula (1) is used in the electron blocking layer of an organic electroluminescent device. The electron blocking layer may contain only the compound represented by general formula (1), or may also contain compounds other than the compound represented by general formula (1). The concentration of the compound represented by general formula (1) in the electron blocking layer is preferably 50% by weight or more, more preferably 90% by weight or more, for example, 99% by weight or more, or even 99.9% by weight or more. The thickness of the electron blocking layer is preferably 1 nm or more, more preferably 3 nm or more, and can be, for example, 5 nm or more, or, for example, 10 nm or more. The thickness of the electron blocking layer is preferably less than 30 nm, more preferably less than 20 nm, and can be, for example, 15 nm or less. The thickness of the electron blocking layer is preferably smaller than the thickness of the light-emitting layer. The thickness of the electron blocking layer is preferably half or less, more preferably one-third or less, and can be, for example, one-quarter or less, of the thickness of the light-emitting layer. Furthermore, it is preferably 1 / 20 or more, and can be, for example, 1 / 10 or more, or 1 / 6 or more. The electron blocking layer containing the compound represented by general formula (1) is preferably provided between the light-emitting layer and the anode. In one embodiment of the present invention, the light-emitting layer and the electron blocking layer are stacked so as to be in direct contact with each other. In one embodiment of the present invention, the present invention includes a stacked structure in which, from the anode side, an electron blocking layer containing the compound represented by general formula (1), an underlayer, and a light-emitting layer are stacked in this order. The electron blocking layer and the underlayer are stacked so as to be in direct contact with each other, and the underlayer and the light-emitting layer are stacked so as to be in direct contact with each other, but the electron blocking layer and the light-emitting layer are not in contact with each other.

[0056] (Underlayer) The underlayer is formed for purposes such as improving the alignment of the light-emitting layer, and is a layer containing a hole-transporting material. In one embodiment of the present invention, the underlayer contains a compound having a common partial structure with the compound contained in the light-emitting layer. The common partial structure here means that the compound has a common partial structure consisting of 12 or more atoms other than hydrogen atoms and deuterium atoms. Preferably, the compound has a common partial structure consisting of 16 or more atoms other than hydrogen atoms and deuterium atoms. For example, the compound may have a common partial structure consisting of 20 or more atoms other than hydrogen atoms and deuterium atoms. In one embodiment of the present invention, the underlayer contains the same compound as the compound contained in the light-emitting layer. In one embodiment of the present invention, the underlayer contains only the same compound as the compound contained in the light-emitting layer. In one embodiment of the present invention, the underlayer contains the same compound as the host material contained in the light-emitting layer. The thickness of the underlayer is preferably 1 nm or more, more preferably 3 nm or more, and can be, for example, 5 nm or more. The thickness of the adjacent layer is preferably less than 30 nm, more preferably less than 20 nm, and can be, for example, 10 nm or less, or 7 nm or less. The thickness of the underlayer is preferably smaller than that of the light-emitting layer. The thickness of the underlayer is preferably equal to or less than half of the thickness of the light-emitting layer, more preferably equal to or less than one-third, and can be, for example, equal to or less than one-quarter. Also, it is preferably equal to or more than one-twentieth, and can be, for example, equal to or more than one-tenth. The thickness of the underlayer is preferably smaller than that of the electron blocking layer. The thickness of the underlayer can be, for example, equal to or less than three-quarters, for example, equal to or less than two-thirds, or for example, equal to or less than one-half of the thickness of the electron blocking layer. Also, it is preferably equal to or more than one-twentieth, and can be, for example, equal to or more than one-tenth, or for example, equal to or more than one-quarter.

[0057] (Light-emitting layer) The light-emitting layer emits light after excitons are generated by the recombination of holes and electrons injected from the anode and cathode, respectively. The light-emitting layer contains at least a light-emitting material. In order for an organic electroluminescent device to achieve high light-emitting efficiency, it is important to confine the singlet and triplet excitons of the light-emitting material within the light-emitting material. Therefore, it is preferable to use a host material in addition to the light-emitting material in the light-emitting layer. As the host material, an organic compound having a higher excited singlet energy than the light-emitting material of the present invention can be used, and it is preferable to use an organic compound having a higher excited singlet energy and a higher excited triplet energy than the light-emitting material. The use of a host material makes it possible to confine the singlet and triplet excitons generated in the light-emitting material within the molecules of the light-emitting material, thereby fully utilizing its light-emitting efficiency. However, high light-emitting efficiency may be achieved even if singlet and triplet excitons cannot be sufficiently confined. Therefore, any host material that can achieve high light-emitting efficiency can be used in the present invention without any particular restrictions. In the organic electroluminescence device of the present invention, the maximum amount of light emitted from the device is light emitted from the light-emitting material contained in the light-emitting layer. This light emission includes fluorescent light and may also include delayed fluorescence. However, light emission from the host material may be present in part or in part of the light emission. When a host material is used, the concentration of the light-emitting material in the light-emitting layer is preferably 0.1 wt % or more, more preferably 1 wt % or more, and preferably 50 wt % or less, more preferably 20 wt % or less, and even more preferably 10 wt % or less.

[0058] An assist dopant may be used in the emitting layer. In this case, the emitting layer is composed of a host material, an assist dopant, and an emitting material. Here, the host material has a higher lowest excited singlet energy level than the assist dopant, and the emitting material has a lower lowest excited singlet energy level than the assist dopant. In the present invention, it is particularly preferable to use a delayed fluorescent material as the assist dopant. Delayed fluorescence is fluorescence emitted when an excited compound undergoes reverse intersystem crossing from an excited triplet state to an excited singlet state and then returns to the ground state from that excited singlet state. This fluorescence is observed later than the fluorescence (prompt fluorescence) from the excited singlet state resulting from a direct transition from the ground state. In the present invention, when the luminescence transient decay curve of a thin film containing the target compound is measured at 300 K, if a luminescent component with a long luminescence lifetime (delayed fluorescence) is observed in addition to a luminescent component with a short luminescence lifetime (prompt fluorescence), the target compound is considered to be a delayed fluorescent material. The delayed fluorescent material is preferably a thermally activated delayed fluorescent material capable of undergoing reverse intersystem crossing upon absorption of thermal energy. The thermal activation of a delayed fluorescent material can be confirmed by the fact that the luminescence lifetime, determined by measuring the luminescence transient decay curve, increases depending on the measurement temperature. By using a delayed fluorescent material as an assist dopant, the energy of the excited singlet state generated by direct transition from the ground state in the assist dopant and the excited singlet energy due to reverse intersystem crossing are efficiently transferred to the luminescent material, thereby effectively assisting the luminescence of the luminescent material. When the luminescent layer is composed of a host material, an assist dopant, and a luminescent material, the concentration of the assist dopant in the luminescent layer is preferably lower than the content of the host material. Specifically, when the total weight of the content of the host material, the content of the assist dopant, and the content of the luminescent material is taken as 100% by weight, the content of the host material is preferably 15% by weight or more and 99.9% by weight or less, the content of the assist dopant is preferably 5.0% by weight or more and 50% by weight or less, and the content of the luminescent material is preferably 0.5% by weight or more and 5.0% by weight or less. In one embodiment of the present invention, the light-emitting layer does not contain an inorganic compound or a metal atom.In one embodiment of the present invention, no phosphorescence is observed from the light-emitting layer at 300K.

[0059] The host material used in the light-emitting layer is preferably an organic compound that has hole-transporting and electron-transporting capabilities, prevents the emission wavelength from shifting to longer wavelengths, and has a high glass transition temperature. In one embodiment of the present invention, a compound containing a carbazole structure can be preferably selected as the host material. In a preferred embodiment of the present invention, the host material contains two or more structures selected from the group consisting of a carbazole structure, a dibenzofuran structure, and a dibenzothiophene structure. For example, a compound containing two structures or a compound containing three structures can be selected. In a preferred embodiment of the present invention, the host material can be selected as a compound containing a 1,3-phenylene structure. In a preferred embodiment of the present invention, the host material can be selected as a compound containing a biphenylene structure. In a preferred embodiment of the present invention, the host material can be selected as a compound containing 5 to 8 benzene rings in the molecule. For example, a compound containing 5, 6, or 7 benzene rings can be selected. Preferred compounds that can be used as the host material are listed below, but the host materials that can be employed in the present invention should not be construed as being limited by the specific examples below.

[0060] In the light-emitting layer, a delayed fluorescent material can be used as the light-emitting material or the assist dopant. Different delayed fluorescent materials can be used as the light-emitting material and the assist dopant. When the emission lifetime is measured using a fluorescence lifetime measurement system (such as a streak camera system manufactured by Hamamatsu Photonics), fluorescence with an emission lifetime of 100 ns (nanoseconds) or more is usually observed. The delayed fluorescent material has a difference ΔE between the lowest excited singlet energy and the lowest excited triplet energy at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. ＳＴ If the δ is small, reverse intersystem crossing from the excited singlet state to the excited triplet state is easily achieved by absorbing thermal energy, and the material functions as a thermally activated delayed fluorescent material. Thermally activated delayed fluorescent materials absorb heat emitted by a device and relatively easily undergo reverse intersystem crossing from the excited triplet state to the excited singlet state, allowing the excited triplet energy to efficiently contribute to light emission.

[0061] In the present invention, the lowest excited singlet energy (E Ｓ１ ) and the lowest excited triplet energy (E Ｔ１ ) is a value determined by the following procedure. ＳＴ is E Ｓ１ -E Ｔ１ (1) The lowest excited singlet energy (E Ｓ１ ) Thin film or toluene solution of the compound to be measured (concentration 10 －５ A sample is prepared by preparing a solution of 1000 mol / L. The fluorescence spectrum of this sample is measured at room temperature (300K). The fluorescence spectrum has the vertical axis representing emission and the horizontal axis representing wavelength. A tangent line is drawn to the rising edge of the short wavelength side of this emission spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is determined. This wavelength value is converted to an energy value using the following conversion formula, and the value is called E Ｓ１ Conversion formula: E Ｓ１ [eV] = 1239.85 / λedge. The emission spectra in the examples described below were measured using an LED light source (Thorlabs, M300L4) as the excitation light source and a detector (Hamamatsu Photonics, PMA-12 multichannel spectrometer C10027-01). (2) Lowest excited triplet energy (E Ｔ１ ) lowest excited singlet energy (E Ｓ１The same sample used in the measurement of ) is cooled to 77 [K] with liquid nitrogen, and the sample for phosphorescence measurement is irradiated with excitation light (300 nm), and the phosphorescence is measured using a detector. The emission from 100 milliseconds after irradiation with excitation light is taken as the phosphorescence spectrum. A tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is determined. This wavelength value is converted to an energy value using the following conversion formula, and the value E Ｔ１ Conversion formula: E Ｔ１ [eV] = 1239.85 / λedge A 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 among the spectral maxima, consider a 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 maximum is defined as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points having peak intensities that are 10% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is maximum and is closest to the shortest wavelength maximum is defined as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.

[0062] It is preferable that the delayed fluorescent material does not contain metal atoms. For example, a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected as the delayed fluorescent material. For example, a compound consisting of carbon atoms, hydrogen atoms, and nitrogen atoms may be selected as the delayed fluorescent material. Typical delayed fluorescent materials include compounds having a structure in which one to two acceptor groups and at least one donor group are bonded to a benzene ring. Preferred examples of the acceptor group include groups containing a heteroaryl ring containing a nitrogen atom as a ring skeleton-constituting atom, such as a cyano group or a triazinyl ring. Preferred examples of the donor group include a substituted or unsubstituted carbazol-9-yl group. Examples of such compounds include a compound in which three or more substituted or unsubstituted carbazol-9-yl groups are bonded to the benzene ring, and a compound in which each of the five-membered ring moieties of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, or a substituted or unsubstituted silaindene ring is condensed to at least one of the two benzene rings constituting the carbazol-9-yl group.

[0063] In a preferred embodiment of the present invention, a compound represented by the following general formula (4) is used as the delayed fluorescent material. In general formula (4), R ２１ ~R ２３ one of the groups represents a cyano group or a group represented by the following general formula (5), and R ２１ ~R ２３ The remaining two and R ２４ and R ２５ At least one of R represents a group represented by the following general formula (6): ２１ ~R ２５ The remainder represents a hydrogen atom or a substituent (however, the substituent here does not represent a cyano group, a group represented by the following general formula (5), or a group represented by the following general formula (6)). In general formula (5), L １ represents a single bond or a divalent linking group, R ３１ and R ３２each independently represents a hydrogen atom or a substituent, and * represents the bonding position. In general formula (6), L ２ represents a single bond or a divalent linking group, R ３３ and R ３４ each independently represents a hydrogen atom or a substituent, and * represents the bonding position.

[0064] In a preferred embodiment of the present invention, R ２２ is a cyano group. In a preferred embodiment of the present invention, R ２２ is a group represented by general formula (5). ２１ is a cyano group or a group represented by general formula (5). ２３ is a cyano group or a group represented by general formula (5). ２１ ~R ２３ In one embodiment of the present invention, one of R ２１ ~R ２３ One of the groups is a group represented by general formula (5).

[0065] In a preferred embodiment of the present invention, L in general formula (5) １ is a single bond. In one aspect of the present invention, L １ is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group, and even more preferably a substituted or unsubstituted 1,4-phenylene group (with, for example, an alkyl group having 1 to 3 carbon atoms as the substituent). In one embodiment of the present invention, R ３１ and R ３２ are each independently one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), and alkynyl groups (e.g., having 1 to 40 carbon atoms) (hereinafter, these groups are referred to as "groups of substituent group A"). In a preferred embodiment of the present invention, R ３１ and R ３２are each independently a substituted or unsubstituted aryl group (e.g., having 6 to 30 carbon atoms), and examples of the substituent of the aryl group include the groups in Substituent Group A. In a preferred embodiment of the present invention, R ３１ and R ３２ are identical.

[0066] In a preferred embodiment of the present invention, L in general formula (6) ２ is a single bond. In one aspect of the present invention, L ２ is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group, and even more preferably a substituted or unsubstituted 1,4-phenylene group (with, for example, an alkyl group having 1 to 3 carbon atoms as the substituent). In one embodiment of the present invention, R ３３ and R ３４each independently represents a substituted or unsubstituted alkyl group (e.g., having 1 to 40 carbon atoms), a substituted or unsubstituted alkenyl group (e.g., having 1 to 40 carbon atoms), a substituted or unsubstituted aryl group (e.g., having 6 to 30 carbon atoms), or a substituted or unsubstituted heteroaryl group (e.g., having 5 to 30 carbon atoms). Examples of the substituents on the alkyl group, alkenyl group, aryl group, and heteroaryl group mentioned here include a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 atoms constituting the ring skeleton), a heteroaryloxy group (e.g., having 5 to 30 atoms constituting the ring skeleton), and a heteroarylthi group. Examples of the substituents include one or a combination of two or more groups selected from the group consisting of an aryl group (e.g., 5 to 30 atoms constituting the ring skeleton), an acyl group (e.g., 1 to 40 carbon atoms), an alkenyl group (e.g., 1 to 40 carbon atoms), an alkynyl group (e.g., 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., 1 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), a nitro group, and a cyano group (hereinafter, these groups are referred to as "groups of substituent group B"). ３３ and R ３４ may be bonded to each other via a single bond or a linking group to form a cyclic structure. ３３ and R ３４ are aryl groups, they are preferably bonded to each other via a single bond or a linking group to form a cyclic structure. The linking group here includes -O-, -S-, -N(R ３５ ) -, -C(R ３６ ) (R ３７ )-, -C(=O)-, and -O-, -S-, -N(R ３５ ) -, -C(R ３６ ) (R ３７ )- is preferred, and —O—, —S—, —N(R ３５ )- is more preferred.３５ ~R ３７ each independently represents a hydrogen atom or a substituent. The substituent may be selected from the groups in the above-mentioned Substituent Group A or the groups in the below-mentioned Substituent Group B, and is preferably one group or a combination of two or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and aryl groups having 6 to 14 carbon atoms.

[0067] The group represented by general formula (6) is preferably a group represented by the following general formula (7).

[0068] L in general formula (7) １１ represents a single bond or a divalent linking group. １１ For the description and preferred range of ２ The description and preferred range of R in general formula (7) can be referred to. ４１ ~R ４８ R each independently represents a hydrogen atom or a substituent. ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ , R ４４ and R ４５ , R ４５ and R ４６ , R ４６ and R ４７ , R ４７ and R ４８may be bonded to each other to form a cyclic structure. The cyclic structure formed by bonding to each other may be an aromatic ring or an aliphatic ring, may contain a heteroatom, and may further be a fused ring of two or more rings. The heteroatom referred to here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an imidazoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptaene ring, a furan ring, a thiophene ring, a naphthyridine ring, a quinoxaline ring, and a quinoline ring. For example, a ring formed by condensing multiple rings, such as a phenanthrene ring or a triphenylene ring, may be formed. The number of rings contained in the group represented by general formula (7) may be selected from the range of 3 to 5, or may be selected from the range of 5 to 7. ４１ ~R ４８ Examples of the substituent that R may have include the groups in the above-mentioned substituent group B, and preferably an unsubstituted alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms which may be substituted with an unsubstituted alkyl group having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R ４１ ~R ４８ is a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R ４１ ~R ４８ is a hydrogen atom or an unsubstituted aryl group having 6 to 10 carbon atoms. ４１ ~R ４８ are all hydrogen atoms. In general formula (7), * represents a bonding position.

[0069] In a preferred embodiment of the present invention, an azabenzene derivative is used as the delayed fluorescent material. In a preferred embodiment of the present invention, the azabenzene derivative has an azabenzene structure in which three of the carbon atoms constituting the ring skeleton of the benzene ring are substituted with nitrogen atoms. For example, an azabenzene derivative having a 1,3,5-triazine structure can be preferably selected. In a preferred embodiment of the present invention, the azabenzene derivative has an azabenzene structure in which two of the carbon atoms constituting the ring skeleton of the benzene ring are substituted with nitrogen atoms. For example, azabenzene derivatives having a pyridazine structure, pyrimidine structure, or pyrazine structure can be mentioned, and an azabenzene derivative having a pyrimidine structure can be preferably selected. In one embodiment of the present invention, the azabenzene derivative has a pyridine structure in which one of the carbon atoms constituting the ring skeleton of the benzene ring is substituted with a nitrogen atom.

[0070] In a preferred embodiment of the present invention, a compound represented by the following general formula (8) is used as the delayed fluorescent material. In the general formula (8), Y １ , Y ２ and Y ３ In one embodiment of the present invention, Y １ is a nitrogen atom, and Y ２ and Y ３ is a methine group. １ and Y ２ is a nitrogen atom, and Y ３ is a methine group. １ ~Y ３ In general formula (8), all of Z １ ~Z ３ Each of Z independently represents a hydrogen atom or a substituent, and at least one of them is a donor substituent. A donor substituent refers to a group having a negative Hammett σp value. １ ~Z ３ At least one of Z is a group containing a diarylamino structure (two aryl groups bonded to a nitrogen atom may be bonded to each other), more preferably a group represented by the above general formula (6), for example a group represented by the above general formula (7). １ ~Z３ In one embodiment of the present invention, only one of Z is a group represented by general formula (6) or (7). １ ~Z ３ In one embodiment of the present invention, only two of Z are independently a group represented by general formula (6) or (7). １ ~Z ３ are each independently a group represented by general formula (6) or (7). For details and preferred ranges of general formula (6) and general formula (7), reference can be made to the corresponding descriptions above. The remaining Z which are not a group represented by general formula (6) or general formula (7) １ ~Z ３ is preferably a substituted or unsubstituted aryl group (e.g., having 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms), and examples of the substituent of the aryl group herein include one group selected from the group consisting of aryl groups (e.g., having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms) and alkyl groups (e.g., having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms), or a group consisting of a combination of two or more groups. In one embodiment of the present invention, general formula (8) does not contain a cyano group.

[0071] In a preferred embodiment of the present invention, a compound represented by the following general formula (9) is used as the delayed fluorescent material. In the general formula (9), Ar 1 is the following A １ and D １ Ar forms a cyclic structure which may be substituted by Ar and represents a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. ２ , Ar ３ may each form a cyclic structure, and when a cyclic structure is formed, it represents a benzene ring, a naphthalene ring, a pyridine ring, or a benzene ring substituted with a cyano group. m1 represents an integer of 0 to 2, and m2 represents an integer of 0 to 1. A １ represents a cyano group, a phenyl group, a pyrimidyl group, a triazyl group, or a benzonitrile group. １ represents a substituted or unsubstituted 5H-indolo[3,2,1-de]phenazin-5-yl group, or a substituted or unsubstituted heterocyclic fused carbazolyl group not containing a naphthalene structure, and１ When present, they may be the same or different. １ The substituents may be bonded to each other to form a ring structure.

[0072] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E1):

[0073] In general formula (E1), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of the C-R groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent.１ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0074] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E2).

[0075] In general formula (E2), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R１６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0076] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E3).

[0077] In formula (E3), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0078] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E4).

[0079] In formula (E4), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３, Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0080] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E5).

[0081] In general formula (E5), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R ２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0082] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E6).

[0083] In general formula (E6), R ２０１ ~R ２２１ R each independently represents a hydrogen atom, a deuterium atom, or a substituent, and preferably represents a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or a group in which an alkyl group and an aryl group are bonded. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R ２０６ , R ２０６ and R ２０７ , R ２０７ and R ２０８ , R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１ At least one pair of R is bonded to each other to form a benzofuro structure or a benzothieno structure. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R２０６ , R ２０６ and R ２０７ , R ２０７ and R ２０８ and one or two of R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１ One or two of the groups bond together to form a benzofuro structure or a benzothieno structure. ２０３ and R ２０４ are bonded to each other to form a benzofuro or benzothieno structure, and even more preferably R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure. Particularly preferably, R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure, and R ２０６ and R ２１９ is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group). ２０１ ~R ２０８ , R ２１４ ~R ２２１ may each independently be a deuterium atom, but may each independently be a hydrogen atom ( １ H), i.e., R ２０１ ~R ２０８ , R ２１４ ~R ２２１ contains an atom with one proton, the atom is limited to a deuterium atom.

[0084] Furthermore, compounds represented by general formula (1) described in the specifications of Japanese Patent Application Nos. 2021-103698, 2021-103699, 2021-103700, 2021-081332, 2021-103701, 2021-151805, and 2021-188860 can be used as delayed fluorescent materials. These descriptions of general formula (1) and specific compounds are herein cited as part of this specification.

[0085] Preferred compounds that can be used as delayed fluorescent materials are listed below: In the structural formulas of the following exemplary compounds, t-Bu represents a tertiary butyl group (tert-butyl group).

[0086] Compounds in which all hydrogen atoms in the above compounds T1 to T151 are substituted with deuterium atoms are exemplified here as T1(D) to T151(D). Compounds in which all hydrogen atoms in the substituted or unsubstituted carbazol-9-yl groups (including those further fused with a ring) present in the above compounds T1 to T151 are substituted with deuterium atoms are exemplified here as T1(d) to T151(d).

[0087] In addition to the above, known delayed fluorescent materials can be used in appropriate combination. Even unknown delayed fluorescent materials can be used. Examples of delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraphs 0008 to 007 of WO2013 / 081088. 1 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraphs 0008 to 0032 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017- JP-A-2017-226838, paragraphs 0010 to 0050, JP-A-2018-100411, paragraphs 0012 to 0043, and WO 2018 / 047853, paragraphs 0016 to 0044. Compounds encompassed by the general formulas described in paragraphs 0012 to 0025, particularly exemplary compounds, which emit delayed fluorescence can be mentioned.Also, Japanese Patent Application Laid-Open No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 00858 0 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 133 It is also possible to employ luminescent materials that emit delayed fluorescence, such as those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0088] When a delayed fluorescent material is used as an assist dopant in the light-emitting layer, a compound having a lower minimum excited singlet energy than the assist dopant is used as the light-emitting material. Examples of light-emitting materials used in combination with the assist dopant include compounds having a multiple resonance effect of boron atoms and nitrogen atoms, and compounds containing a fused aromatic ring structure such as anthracene, pyrene, and perylene. The delayed fluorescent materials exemplified above can also be used. In a preferred embodiment of the present invention, a compound represented by the following general formula (F1) is used as the light-emitting material used in combination with the assist dopant. General formula (F1)

[0089] In the above general formula (F1), Ar １~Ar ３ are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted, or the rings may be fused. When a hydrogen atom is substituted, it is preferably substituted with one group or a combination of two or more groups selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group. When the rings are fused, it is preferably fused with a benzene ring or a heteroaromatic ring (for example, a furan ring, a thiophene ring, a pyrrole ring, etc.). R ａ and R ａ R' each independently represents a substituent, and is preferably one group or a combination of two or more groups selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group. ａ and Ar １ , Ar １ and Ar ２ , Ar ２ and R ａ ', R ａ ' and Ar ３ , Ar ３ and R ａ may be bonded to each other to form a cyclic structure.

[0090] The compound represented by the general formula (F1) preferably contains at least one carbazole structure. For example, one of the benzene rings constituting the carbazole structure is Ar １ and one of the benzene rings constituting the carbazole structure may be represented by Ar ２ and one of the benzene rings constituting the carbazole structure may be represented by Ar ３ In addition, Ar may be a ring represented by the formula: １ ~Ar ３ A carbazolyl group may be bonded to one or more of the following. For example, Ar ３ A substituted or unsubstituted carbazol-9-yl group may be bonded to the ring represented by the formula:

[0091] Ar １ ~Ar ３ Ar may have a fused aromatic ring structure such as anthracene, pyrene, or perylene bonded thereto.１ ~Ar ３ The ring represented by R may be one of the rings constituting a fused aromatic ring structure. ａ and R ａ At least one of the groups may be a group having a fused aromatic ring structure.

[0092] A compound may contain a plurality of skeletons represented by general formula (F1). For example, the compound may have a structure in which skeletons represented by general formula (F1) are bonded to each other via a single bond or a linking group. Furthermore, the skeleton represented by general formula (F1) may further have a structure exhibiting a multiple resonance effect in which benzene rings are linked to each other via a boron atom, a nitrogen atom, an oxygen atom, or a sulfur atom.

[0093] In a preferred embodiment of the present invention, a compound containing a BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) structure is used as the light-emitting material used in combination with the assist dopant. For example, a compound represented by the following general formula (F2) is used.

[0094] In general formula (F2), R １ ~R ７ are each independently a hydrogen atom, a deuterium atom, or a substituent. １ ~R ７ At least one of the above is preferably a group represented by the following general formula (F3): In general formula (F3), R １１ ~R １５ Each independently represents a hydrogen atom, a deuterium atom or a substituent, and * represents a bonding position. １ ~R ７ In a preferred embodiment of the present invention, the number of R １ ~R ７ In a preferred embodiment of the present invention, at least one of R １ , R３ , R ５ , R ７ is a group represented by general formula (F3). In a preferred embodiment of the present invention, R １ , R ３ , R ４ , R ５ , R ７ In a preferred embodiment of the present invention, only R １ , R ３ , R ４ , R ５ , R ７ is a group represented by general formula (F3), and R ２ and R ４ is a hydrogen atom, a deuterium atom, an unsubstituted alkyl group (e.g., having 1 to 10 carbon atoms), or an unsubstituted aryl group (e.g., having 6 to 14 carbon atoms). １ ~R ７ In a preferred embodiment of the present invention, all of R １ and R ７ In a preferred embodiment of the present invention, R ３ and R ５ In a preferred embodiment of the present invention, R ２ and R ６ In a preferred embodiment of the present invention, R １ and R ７ are identical, and R ３ and R ５ are the same and R １ and R ３ In a preferred embodiment of the present invention, R １ , R ３ , R ５ , R ７ In a preferred embodiment of the present invention, R １ and R ４ and R ７ are identical, and R ３ or R ５ In a preferred embodiment of the present invention, R ３ and R ４ and R ５ are identical, and R １ or R ７In a preferred embodiment of the present invention, R １ , R ３ , R ５ , R ７ are all R ４ is different.

[0095] R in general formula (F3) １１ ~R １５ The substituents that may be taken by may be selected, for example, from the following Substituent Group A, from the following Substituent Group B, from the following Substituent Group C, or from the following Substituent Group D. When a substituted amino group is selected as the substituent, a di-substituted amino group is preferred, and the two substituents on the amino group are preferably each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group (a diarylamino group) is particularly preferred. The substituents that may be taken by the two aryl groups of the diarylamino group may be selected, for example, from the following Substituent Group A, from the following Substituent Group B, from the following Substituent Group C, or from the following Substituent Group D. The two aryl groups of the diarylamino group may be bonded to each other via a single bond or a linking group, and the linking group referred to here is represented by R ３３ and R ３４ The explanation of the linking group in the above formula (9) can be referred to. A specific example of the diarylamino group is a substituted or unsubstituted carbazol-9-yl group. Examples of the substituted or unsubstituted carbazol-9-yl group include L １１ In a preferred embodiment of the present invention, R in general formula (F3) is a single bond. １３ is the only substituent, and R １１ , R １２ , R １４ , R １５ In a preferred embodiment of the present invention, R in general formula (F3) is a hydrogen atom. １１ is the only substituent, and R １２ , R １３ , R １４ , R １５In a preferred embodiment of the present invention, R in general formula (F3) is a hydrogen atom. １１ and R １３ is the only substituent, and R １２ , R １４ , R １５ is a hydrogen atom. １ ~R ７ Among these, R of general formula (F3) １１ ~R １５ may contain a group in which all of R are hydrogen atoms (i.e., a phenyl group). ２ , R ４ , R ６ may be a phenyl group.

[0096] In general formula (F2), R ８ and R ９ are each independently one group or a combination of two or more groups selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), and a cyano group. In a preferred embodiment of the present invention, R ８ and R ９ In a preferred embodiment of the present invention, R ８ and R ９ is a halogen atom, and is particularly preferably a fluorine atom.

[0097] In one embodiment of the present invention, R １ ~R ９ The total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present in R in general formula (F2) is preferably 3 or more, and for example, a compound having 3 or 4 groups can be used. １ ~R ７ The total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present in R is preferably three or more, and for example, a compound having three or four groups may be employed.８ and R ９ In general formula (F2), an alkoxy group, an aryloxy group, or an amino group may not be present. １ , R ３ , R ４ , R ５ , R ７ The total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present in R is preferably three or more, and for example, a compound having three or four groups may be employed. ２ , R ６ , R ８ , R ９ In a preferred embodiment of the present invention, R has three or more substituted or unsubstituted alkoxy groups. In a preferred embodiment of the present invention, R has four or more substituted or unsubstituted alkoxy groups. In a preferred embodiment of the present invention, R has one or more substituted or unsubstituted alkoxy groups and two or more substituted or unsubstituted aryloxy groups. In a preferred embodiment of the present invention, R has two or more substituted or unsubstituted alkoxy groups and one or more substituted or unsubstituted amino groups. In a preferred embodiment of the present invention, R １ , R ４ , R ７ In a preferred embodiment of the present invention, R １ , R ４ , R ７ Each of these groups contains a substituted or unsubstituted alkoxy group.

[0098] In one embodiment of the present invention, R １ ~R ９The total number of substituents having a Hammett σp value of less than -0.2 present in general formula (F2) is three or more. Examples of substituents having a Hammett σp value of less than -0.2 include a methoxy group (-0.27), an ethoxy group (-0.24), an n-propoxy group (-0.25), an isopropoxy group (-0.45), and an n-butoxy group (-0.32). On the other hand, a fluorine atom (0.06), a methyl group (-0.17), an ethyl group (-0.15), a tert-butyl group (-0.20), an n-hexyl group (-0.15), a cyclohexyl group (-0.15), and the like are not substituents having a Hammett σp value of less than -0.2. In one embodiment of the present invention, １ ~R ９ It is possible to adopt a compound having three or four substituents each having a Hammett's σp value of less than −0.2 in the general formula (F2). １ ~R ７ Preferably, the number of substituents present in R having a Hammett's σp value of less than −0.2 is three or more, and for example, a compound having three or four substituents can be used. ８ and R ９ In general formula (F2), R may not have a substituent with a Hammett σp value of less than −0.2. １ , R ３ , R ４ , R ５ , R ７ The number of substituents having a Hammett's σp value of less than −0.2 present in R is preferably three or more, and for example, a compound having three or four substituents can be used. ２ , R ６ , R ８ , R ９ In a preferred embodiment of the present invention, R １ , R ４ , R ７ Each of these groups has a substituent with a Hammett σp value of less than −0.2.

[0099] In the present invention, a compound containing a carbazole structure may be selected as the light-emitting material used in combination with the assist dopant, or a compound containing no carbazole structure, dibenzofuran structure, or dibenzothiophene structure may be selected as the light-emitting material used in combination with the assist dopant.

[0100] Preferred compounds that can be used as luminescent materials in combination with an assist dopant are listed below. However, the luminescent materials that can be used in combination with an assist dopant in the present invention should not be construed as being limited by the specific examples below. In the structural formulas of the following exemplary compounds, t-Bu represents a tertiary butyl group (tert-butyl group).

[0101] Derivatives of the above-exemplified compounds include compounds in which at least one hydrogen atom is substituted with a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, or a diarylamino group. In addition, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be preferably used as light-emitting materials to be used in combination with an assist dopant.

[0102] In a preferred embodiment of the present invention, a compound represented by the following general formula (G) is used in the light-emitting layer. The compound represented by general formula (G) is preferably employed as a light-emitting material used in combination with an assist dopant. The compound represented by general formula (G) may be employed as an assist dopant. General formula (G)

[0103] In general formula (G), X １ and X ２ In one embodiment of the present invention, X is a nitrogen atom and the other is a boron atom. １ is a nitrogen atom, and X ２ is a boron atom. In this case, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring. １ is a boron atom, and X２ is a nitrogen atom. In this case, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring.

[0104] In general formula (G), R １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. ７ and R ８The ring structure formed by the bonding of R contains a boron atom and four carbon atoms as ring skeleton constituent atoms. １７ and R １８ The cyclic structure formed by bonding is X １ When X is a boron atom, the ring skeleton contains the boron atom and four carbon atoms. １ When R is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. ２１ and R ２２ The cyclic structure formed by bonding is X ２ When X is a boron atom, the ring skeleton contains the boron atom and four carbon atoms. ２ When R is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ When R are bonded to each other to form a cyclic structure containing a boron atom, the cyclic structure is preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring. ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ When they are bonded to each other, they are bonded to each other to form a single bond, —O—, —S—, —N(R ２７ ) -, -C(R ２８ ) (R ２９ ) -, -Si(R ３０ ) (R ３１ ) -, -B(R ３２ )-, -CO-, -CS-, and preferably forms -O-, -S- or -N(R ２７ )-, and more preferably -N(R ２７ )-, where R ２７ ~R ３２ Each of R independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be a group selected from any of the substituent groups A to E described below, but is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and particularly preferably R２７ is preferably a substituted or unsubstituted aryl group. ２７ ~R ３２ is a substituent, R ７ and R ８ R in the ring formed by bonding together ２７ ~R ３２ is R ６ and R ９ may further bond to at least one of the following to form a cyclic structure; １７ and R １８ R in the ring formed by bonding together ２７ ~R ３２ is R １６ and R １９ may further bond to at least one of the following to form a cyclic structure; ２１ and R ２２ R in the ring formed by bonding together ２７ ~R ３２ is R ２０ and R ２３ In one embodiment of the present invention, R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ In one aspect of the present invention, only one pair of R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ In one aspect of the present invention, only two pairs of R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ All of these are connected to each other.

[0105] R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６The cyclic structure formed by bonding together may be an aromatic ring or an aliphatic ring, may contain a heteroatom, and may further be fused with one or more other rings. The heteroatom referred to here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptene ring, and a ring further fused with one or more rings selected from the group consisting of these rings. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring (which may be further fused with a ring), for example, a benzene ring optionally substituted with an alkyl group or an aryl group. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted heteroaromatic ring, and is preferably a furan ring of benzofuran or a thiophene ring of benzothiophene. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ The number of combinations that are bonded to each other to form a cyclic structure may be 0, or may be, for example, any of 1 to 6. For example, it may be any of 1 to 4, and 1, 2, 3, or 4 may be selected. In one embodiment of the present invention, R １ and R ２ , R ２ and R ３ , R ３ and R ４ In one embodiment of the present invention, a pair of R ５ and R ６ are bonded to each other to form a ring structure. ９ and R １０ , R １０ and R １１ , R １１ and R １２ In one embodiment of the present invention, a pair of R １ and R ２ , R １３ and R １４ are bonded to each other to form a cyclic structure. １ and R ２ , R ２ and R ３ , R ３ and R ４ are bonded to each other to form a cyclic structure, and R ５ and R ６ are bonded to each other to form a ring structure. ５ and R ６ , R １９ and R ２０ are all bonded to each other to form a ring structure.

[0106] Adjacent Rｎ (n=1 to 26) and R １ ~R ２６ is a hydrogen atom, a deuterium atom, or a substituent. As the substituent, a group selected from any one of the substituent groups A to E described below can be used. １ ~R ２６ Preferred substituents that R may have are substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups. For example, the substituent may be a substituted or unsubstituted aryl group, or for example, the substituent may be a substituted or unsubstituted alkyl group. The substituents of the alkyl group, aryl group, and heteroaryl group mentioned here can also be groups selected from any of substituent groups A to E, but are preferably one or more groups selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, and are more preferably groups of substituent group E, which may be unsubstituted. In one preferred embodiment of the present invention, R １ ~R ６ At least one of R is a substituent, preferably a group of the substituent group E. For example, R ２ ~R ６ At least one of R is a substituent, preferably a group of the substituent group E. For example, R ５ and R ６ In a preferred embodiment of the present invention, at least one of R ３ and R ６ In a preferred embodiment of the present invention, at least one of X is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. １ is a nitrogen atom, R １５ and R ２０ At least one of R is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. １７ and R １８ In a preferred embodiment of the present invention, X ２ is a nitrogen atom, R １９ and R ２４At least one of R is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. ２１ and R ２２ are bonded to each other to form a single bond. ８ and R １２ In one embodiment of the present invention, at least one of R ８ , R １０ and R １２ is a substituent. ８ ~R １２ The substituent of R is preferably an unsubstituted alkyl group. ８ and R １２ is an alkyl group having 2 or more carbon atoms (preferably an alkyl group having 3 or more carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms, and even more preferably an alkyl group having 3 or 4 carbon atoms), the orientation becomes high when made into a film, which is preferable. ８ and R １２ is a substituent (preferably an alkyl group, more preferably an alkyl group having 2 or more carbon atoms, even more preferably an alkyl group having 3 or more carbon atoms, still more preferably an alkyl group having 3 to 8 carbon atoms, particularly preferably an alkyl group having 3 or 4 carbon atoms), and R １ ~R ６ It is particularly preferred that at least one of X is a substituent (preferably a group of the substituent group E). １ is a boron atom, R １３ and R １７ In one aspect of the present invention, at least one of X is a substituent, and preferably both are substituents. １ is a boron atom, R １３ , R １５ and R １７ is a substituent. １ is a boron atom, R １３ ~R １７ The substituent of X is preferably an unsubstituted alkyl group. ２ is a boron atom, R ２２ and R ２６ In one aspect of the present invention, at least one of X is a substituent, and preferably both are substituents.２ is a boron atom, R ２２ , R ２４ and R ２６ is a substituent. ２ is a boron atom, R ２２ ~R ２６ The substituent of is preferably an unsubstituted alkyl group. １ or X ２ Specific examples of the group bonded to a boron atom represented by are listed below. However, the groups bonded to a boron atom that can be employed in the present invention are not limited to the following specific examples. In this specification, a methyl group is represented by CH ３ * indicates a bond position.

[0107] In the following, R in general formula (G) １ ~R ２６ Here are some specific examples: １ ~R ７ , X １ is a nitrogen atom, R １３ ~R ２１ , X ２ is a nitrogen atom, R １８ ~R ２６ is preferably Z1 to Z9, and R ８ ~R １２ , X １ is a nitrogen atom, R ２２ ~R ２６ , X ２ is a nitrogen atom, R １３ ~R １７ As the groups, Z1 to Z7 are preferred. However, the groups bonded to boron atoms that can be employed in the present invention should not be construed as being limited by the following specific examples. D represents a deuterium atom. * represents the bonding position.

[0108] A １ and A ２ is a hydrogen atom, a deuterium atom or a substituent. As the substituent, a group selected from any one of the substituent groups A to E described below can be used. In a preferred embodiment of the present invention, A １ and A ２are each independently a hydrogen atom or a deuterium atom. １ and A ２ is a hydrogen atom. For example, A １ and A ２ is a deuterium atom. １ and A ２ One of A may be a substituent. １ and A ２ may each independently be a substituent. １ and A ２ A preferred substituent that can be taken by A is an acceptor group. The acceptor group is a group having a positive Hammett σp value. １ and A ２The acceptor group that can be adopted is more preferably a group having a Hammett σp value of greater than 0.2. Examples of groups having a Hammett σp value of greater than 0.2 include a cyano group, an aryl group substituted with at least a cyano group, a group containing a fluorine atom, and a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom. The aryl group substituted with at least a cyano group may be substituted with a substituent other than a cyano group (e.g., an alkyl group or an aryl group), or may be an aryl group substituted only with a cyano group. The aryl group substituted with at least a cyano group is preferably a phenyl group substituted with at least a cyano group. The number of cyano group substitutions is preferably 1 or 2, for example, it may be 1 or 2. Examples of groups containing fluorine atoms include fluorine atoms, fluorinated alkyl groups, and aryl groups substituted with at least a fluorine atom or a fluorinated alkyl group. The fluorinated alkyl group is preferably a perfluoroalkyl group, preferably having 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. Furthermore, a heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after fusion is preferably 2 to 6, and can be selected from 2 to 4, or can be 2. Specific examples of rings constituting a heteroaryl group include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a naphthyridine ring other than a quinazoline ring or a quinoxaline ring. The ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent, and examples of the substituent include one group selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group, or a group formed by combining two or more of these groups. A １ and A ２ A particularly preferred acceptor group is a cyano group. １ and A ２ In one embodiment of the present invention, at least one of A is an acceptor group. １ and A２ In one aspect of the present invention, only one of A is an acceptor group. １ and A ２ In one aspect of the present invention, both A and A are the same acceptor group. １ and A ２ are different acceptor groups. １ and A ２ is a cyano group. １ and A ２ is a halogen atom, for example a bromine atom.

[0109] Specific examples of the acceptor group that can be used in the present invention are shown below. However, the acceptor group that can be used in the present invention is not limited to the following specific examples. In this specification, a methyl group is represented by CH ３ The symbols are omitted. For example, A15 indicates a group containing two 4-methylphenyl groups. "D" represents a deuterium atom. * indicates the bonding position.

[0110] In addition, X １ is a nitrogen atom, and R ７ and R ８ are bonded via a nitrogen atom to form a 6-membered ring, and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６are bonded to each other to form an aromatic ring (a substituted or unsubstituted benzene ring which may be fused) or a heteroaromatic ring (preferably a furan ring of a substituted or unsubstituted benzofuran which may be fused, or a thiophene ring of a substituted or unsubstituted benzothiophene which may be fused). １ is a boron atom, and X ２ is a nitrogen atom, and R ７ and R ８ , R １７ and R １８ are bonded to each other to form a cyclic structure containing a boron atom, the cyclic structure is a 5- to 7-membered ring, and when it is a 6-membered ring, R ７ and R ８ , R １７ and R １８ are bonded to each other to form -B(R ３２ )-, -CO-, -CS- or -N(R ２７ )- is formed. ２７ preferably represents a hydrogen atom, a deuterium atom or a substituent.

[0111] X in general formula (G) １ When X in general formula (G) is a nitrogen atom, the compound of the present invention has the following skeleton (1a): ２ When is a nitrogen atom, the compound of the present invention has the following skeleton (1b):

[0112] Each hydrogen atom in the skeletons (1a) and (1b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (G). １ ~R ２６ , A １ , A ２ can be referred to. Examples include compounds in which the phenyl groups bonded to the boron atoms in skeletons (1a) and (1b) are all substituted with mesityl groups, 2,6-diisopropylphenyl groups, or 2,4,6-triisopropylphenyl groups. In one embodiment of the present invention, each hydrogen atom in skeletons (1a) and (1b) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0113] A preferred group of compounds having the skeleton (1a) includes compounds represented by the following general formula (1a):

[0114] In the general formula (1a), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ４１ and R ４２ each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represents an integer of 0 to 5, n1 and n3 each independently represents an integer of 0 to 4, and n2 and n4 each independently represents an integer of 0 to 3. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. It is preferred that at least one of n1 to n4 is 1 or greater, and that m1 and m2 are each independently an integer from 1 to 5. In one embodiment of the present invention, n1 to n4 each independently represent an integer from 0 to 2. In a preferred embodiment of the present invention, at least one of n1 to n4 is 1 or greater, preferably at least one of n1 and n2 is 1 or greater, and at least one of n3 and n4 is 1 or greater. In one embodiment of the present invention, n1 and n3 are each independently 1 or 2, and n2 and n4 are 0. In one embodiment of the present invention, n2 and n4 are each independently 1 or 2, and n1 and n3 are 0. In one embodiment of the present invention, n1 to n4 are each independently 1 or 2. In one embodiment of the present invention, n1 and n3 are equal, and n2 and n4 are equal. In one embodiment of the present invention, n1 and n3 are 1, and n2 and n4 are 0. In one embodiment of the present invention, n1 and n3 are 0, and n2 and n4 are 1. In one embodiment of the present invention, n1 to n4 are all 1. Ar １ ~Ar ４ The bonding position of Ar may be at least one of the 3- and 6-positions, at least one of the 2- and 7-positions, at least one of the 1- and 8-positions, or at least one of the 4- and 5-positions of the carbazole ring.１ ~Ar ４ The bonding positions of Ar may be both the 3- and 6-positions, both the 2- and 7-positions, both the 1- and 8-positions, or both the 4- and 5-positions of the carbazole ring. For example, at least one of the 3- and 6-positions can be preferably selected, or both the 3- and 6-positions can be more preferably selected. In a preferred embodiment of the present invention, Ar １ ~Ar ４ In a preferred embodiment of the present invention, Ar １ ~Ar ４ are each independently a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group or naphthyl group, and even more preferably a substituted or unsubstituted phenyl group. Examples of the substituent include a group selected from any of the substituent groups A to E described below, but an unsubstituted phenyl group is also preferred. Ar １ ~Ar ４ Preferred specific examples of R include a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, and a terphenyl group. In one embodiment of the present invention, m1 and m2 each independently represent 0. In one embodiment of the present invention, m1 and m2 each independently represent an integer of 1 to 5. In one embodiment of the present invention, m1 and m2 are equal. In one embodiment of the present invention, R ４１ and R ４２ is an alkyl group having 1 to 6 carbon atoms, and can be selected from alkyl groups having 1 to 3 carbon atoms, for example, or a methyl group. The substitution positions of the alkyl group can be, with the carbon atom bonded to the boron atom being the 1st position, the 2nd position only, the 3rd position only, the 4th position only, the 3rd and 5th positions, the 2nd and 4th positions, the 2nd and 6th positions, or the 2nd, 4th and 6th positions, and the like, with at least the 2nd position being preferred, and at least the 2nd and 6th positions being more preferred. A １ and A ２ For the explanation and preferred range of , the corresponding description of general formula (G) can be referred to.

[0115] Specific examples of compounds represented by general formula (1a) are listed below. The compounds of general formula (1a) that can be used in the present invention are not limited to the specific examples listed below. For example, a preferred group can be the group consisting of the remaining compounds excluding the compound in the center of the fourth row and the compound in the center of the eighth row listed below.

[0116] Another group of specific examples of the compound represented by general formula (1a) is shown below. The compounds of general formula (1a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0117] A preferred group of compounds having the skeleton (1b) includes compounds represented by the following general formula (1b):

[0118] In general formula (1b), Ar ５ ~Ar ８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ４３ and R ４４ each independently represents a substituted or unsubstituted alkyl group. m3 and m4 each independently represent an integer of 0 to 5, n6 and n8 each independently represent an integer of 0 to 3, and n5 and n7 each independently represent an integer of 0 to 4. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５ ~Ar ８ , R ４３ and R ４４ , m3 and m4, n5 to n8, A １ , A ２For details, see Ar in general formula (1a). １ ~Ar ４ , R ４１ and R ４２ , m1 and m2, n1 to n4, A １ , A ２ It is preferable that at least one of n5 to n8 is 1 or more, and m3 and m4 each independently represent an integer of 1 to 5.

[0119] Specific examples of the compound represented by general formula (1b) are listed below. The compounds of general formula (1b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0120] R in general formula (G) ７ and R ８ When these are bonded together to form N-Ph, the compounds of the present invention are １ is a nitrogen atom, the following skeleton (2a) is obtained, for example, ２ When is a nitrogen atom, for example, it has the following skeleton (2b): Ph is a phenyl group. Skeleton (2a)

[0121] Each hydrogen atom in the skeletons (2a) and (2b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (G). １ ~R ２６ , A １ , A ２ can be referred to. At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in the skeleton (2a) is substituted with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeletons (2a) and (2b) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0122] A preferred group of compounds having the skeleton (2a) includes compounds represented by the following general formula (2a):

[0123] In the general formula (2a), Ar ９ ~Ar １４ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n9, n11, n12, and n14 each independently represent an integer of 0 to 4, and n10 and n13 each independently represent an integer of 0 to 2. However, at least one of n9, n10, n12, and n13 is 1 or greater. A １ , A ２ each independently represent a hydrogen atom, a deuterium atom, or a substituent. In one aspect of the present invention, n9 to n14 each independently represent an integer of 0 to 2. In one aspect of the present invention, at least one of n9 to n14 is 1 or greater; for example, n9 and n12 can be 1 or greater, or n10 and n13 can be 1 or greater. In a preferred aspect of the present invention, at least one of n9, n10, n12, and n13 is 1 or greater. In one aspect of the present invention, n9 and n12 are each independently 1 or 2, and n10, n11, n13, and n14 are 0. In one aspect of the present invention, n10 and n13 are each independently 1 or 2, and n9, n11, n12, and n14 are 0. In one aspect of the present invention, n9 and n12 are each independently 1 or 2, n10 and n13 are each independently 1 or 2, and n11 and n14 are 0. In one embodiment of the present invention, n9 to n14 are all 1. ９ ~Ar １４ The bonding positions of Ar may be the 3- and 6-positions of the carbazole ring or other positions. ９ ~Ar １４ are all the same group. ９ ~Ar １４ For preferred groups, Ar １ ~Ar ４ Reference can be made to the corresponding description in １ and A ２ For the explanation and preferred range of , the corresponding description of general formula (G) can be referred to.

[0124] Specific examples of the compound represented by general formula (2a) are listed below. The compounds of general formula (2a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0125] A preferred group of compounds having the skeleton (2b) includes compounds represented by the following general formula (2b):

[0126] In the general formula (2b), Ar １５ ~Ar ２０ Each of n15, n17, n18, and n20 independently represents an integer of 0 to 4, and each of n16 and n19 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １５ ~Ar ２０ , n15-n20, A １ , A ２ For details, see Ar in general formula (2a). ９ ~Ar １４ , n9 to n14, A １ , A ２ The following descriptions can be referred to in order.

[0127] Specific examples of the compound represented by general formula (2b) are listed below. The compounds of general formula (2b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0128] R in general formula (G) ７ and R ８ are bonded to each other to form a single bond, the compounds of the present invention are １ is a nitrogen atom, the following skeleton (3a) is obtained, and X ２ When is a nitrogen atom, for example, it has the following skeleton (3b).

[0129] Each hydrogen atom in the skeletons (3a) and (3b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (G). １ ~R ２６ , A １ , A ２ In one embodiment of the present invention, each hydrogen atom in the skeletons (3a) and (3b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0130] A preferred group of compounds having the skeleton (3a) includes compounds represented by the following general formula (3a):

[0131] In the general formula (3a), Ar ２１ ~Ar ２６ Each of n21, n23, n24, and n26 independently represents an integer of 0 to 4, and each of n22 and n25 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２１ ~Ar ２５ , n21 to n25 are each independently selected from the group consisting of Ar in general formula (2a) and Ar in general formula (2a). ９ ~Ar １４ , n9 to n14, A １ , A ２ The description can be referred to.

[0132] Specific examples of the compound represented by general formula (3a) are listed below. The compounds of general formula (3a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0133] A preferred group of compounds having the skeleton (3b) includes compounds represented by the following general formula (3b):

[0134] In the general formula (3b), Ar ２７ ~Ar ３２ Each of n27, n29, n30, and n32 independently represents an integer of 0 to 4, and each of n28 and n31 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２７ ~Ar ３２ , n27-n32, A １ , A ２ For details, see Ar in general formula (2b). １５ ~Ar ２０ , n15-n20, A １ , A ２ The following descriptions can be referred to in order.

[0135] Specific examples of the compound represented by general formula (3b) are listed below. The compounds of general formula (3b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0136] In a preferred embodiment of the present invention, a compound in which another ring is fused to the two benzene rings constituting the carbazole moiety present in general formula (G) is selected. Among these, a compound in which a benzofuran ring is fused, a compound in which a benzothiophene ring is fused, or a compound in which a benzene ring is fused can be particularly preferably selected. Below, these ring-fused compounds will be described with specific examples.

[0137] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is condensed with the benzene ring, of the two benzene rings constituting the carbazole partial structure present in general formula (G), to which the boron atom is not directly bonded. Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b).

[0138] In skeletons (4a) and (4b), Y １ ~Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ The two hydrogen atoms here indicate that the two benzene rings bonded to the boron atom are not linked to each other. １ and Y ２ are the same, and Y ３ and Y ４ are preferably the same, but may be different. １ ~Y ４ is a single bond. In one aspect of the present invention, Y １ ~Y ４ is N(R ２７ ) R ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ ~Z ４ each independently represents an oxygen atom or a sulfur atom. １ and Z ２ are the same, and Z ３ and Z ４ are preferably the same, but may be different. １ ~Z ４ is an oxygen atom. In this case, the furan ring of benzofuran is fused to the benzene ring constituting the carbazole partial structure in (4a) and (4b). The orientation of the fused furan ring is not limited. In one embodiment of the present invention, Z １ ~Z ４ is a sulfur atom. In this case, the thiophene ring of benzothiophene is fused to the benzene ring constituting the carbazole partial structure in (4a) and (4b). The orientation of the fused thiophene ring is not limited. Each hydrogen atom in the skeletons (4a) and (4b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (G). １ ~R ２６ , A １ , A ２In one embodiment of the present invention, each hydrogen atom in the skeletons (4a) and (4b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0139] As a preferred group of compounds having the skeleton (4a), compounds represented by the following general formula (4a) can be exemplified. X in the specific examples is an oxygen atom or a sulfur atom, and compounds in which X is an oxygen atom and compounds in which X is a sulfur atom are respectively disclosed. X in the specific examples of compounds represented by other general formulas below also has the same meaning. General formula (4a)

[0140] In the general formula (4a), Ar ５１ and Ar ５２ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５１ and R ５２ Each of m51 and m52 independently represents an integer of 0 to 4. Each of n51 and n52 independently represents an integer of 0 to 2. Y １ ~Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ ~Z ４ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n51 and n52 are the same number. For example, n51 and n52 may be 0, or n51 and n52 may be 1. In one embodiment of the present invention, m51 and m52 are the same number. In one embodiment of the present invention, m51 and m52 are integers of 0 to 3. For example, m51 and m52 may be 0, m51 and m52 may be 1, m51 and m52 may be 2, or m51 and m52 may be 3. Ar ５１ , Ar ５２ , R５１ , R ５２ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ , R ４１ ~R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0141] Specific examples of compounds represented by general formula (4a) are listed below. The compounds of general formula (4a) that can be used in the present invention are not limited to the following group of specific examples. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0142] Another group of specific examples of the compound represented by general formula (4a) is shown below. The compounds of general formula (4a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0143] A preferred group of compounds having the skeleton (4b) includes compounds represented by the following general formula (4b):

[0144] In the general formula (4b), Ar ５３ and Ar ５４ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５３ and R ５４Each of m53 and m54 independently represents an integer of 0 to 4. Each of n53 and n54 independently represents an integer of 0 to 2. Y ３ and Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ３ and Z ４ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５３ , Ar ５４ , R ５３ , R ５４ , m53, m54, n53, n54, A １ , A ２ For details, see Ar in general formula (4a). ５１ , Ar ５２ , R ５１ , R ５２ , m51, m52, n51, n52, A １ , A ２ The description can be referred to.

[0145] Specific examples of compounds represented by general formula (4b) are listed below. The compounds of general formula (4b) that can be used in the present invention are not limited to the specific examples below. Specific examples containing X are considered to disclose compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0146] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is condensed with the benzene ring directly bonded to a boron atom, out of the two benzene rings constituting the carbazole partial structure present in general formula (G). Examples of such compounds include a compound having the following skeleton (5a) and a compound having the following skeleton (5b).

[0147] In skeletons (5a) and (5b), Y ５ ~Y ８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Z. ５ ~Z ８ Each independently represents an oxygen atom or a sulfur atom. ５ ~Y ８ , Z ５ ~Z ８ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (5a) and (5b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0148] A preferred group of compounds having the skeleton (5a) includes compounds represented by the following general formula (5a):

[0149] In the general formula (5a), Ar ５５ and Ar ５６ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５５ and R ５６ Each of m55 and m56 independently represents an integer of 0 to 4. Each of n55 and n56 independently represents an integer of 0 to 4. Y ５ and Y ６ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ５ and Z ６ each independently represents an oxygen atom or a sulfur atom. １ , A ２each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n55 and n56 are integers of 0 to 2. For example, n55 and n56 may be 0, or n55 and n56 may be 1. In one embodiment of the present invention, m51 and m52 are the same number. For details of m55 and m56, please refer to the description of m51 and m52 in general formula (4a). Ar ５５ , Ar ５６ , R ５５ , R ５６ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0150] Specific examples of compounds represented by general formula (5a) are listed below. Compounds of general formula (5a) that can be used in the present invention are not limited to the following group of specific examples. Specific examples containing X are considered to disclose compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0151] Another group of specific examples of the compound represented by general formula (5a) is shown below. The compounds of general formula (5a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0152] A preferred group of compounds having the skeleton (5b) includes compounds represented by the following general formula (5b):

[0153] In the general formula (5b), Ar ５７ and Ar ５８R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５７ and R ５８ Each of m57 and m58 independently represents an integer of 0 to 4. Each of n57 and n58 independently represents an integer of 0 to 4. Y ７ and Y ８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ７ and Z ８ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５７ , Ar ５８ , R ５７ , R ５８ , m57, m58, n57, n58, A １ , A ２ For details, see Ar in general formula (5a). ５５ , Ar ５６ , R ５５ , R ５６ , m55, m56, n55, n56, A １ , A ２ The following description can be referred to.

[0154] Specific examples of compounds represented by general formula (5b) are listed below. The compounds of general formula (5b) that can be used in the present invention are not limited to the following group of specific examples. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0155] Another group of specific examples of the compound represented by general formula (5b) is shown below. The compounds of general formula (5b) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0156] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is fused to both of the two benzene rings constituting the carbazole moiety present in general formula (G). Examples of such compounds include a compound having the following skeleton (6a) and a compound having the following skeleton (6b).

[0157] In skeletons (6a) and (6b), Y ９ ~Y １２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Z. ９ ~Z １６ each independently represents an oxygen atom or a sulfur atom. ９ ~Z １６ are preferably the same, but may be different. ９ ~Z １６ is an oxygen atom. In one aspect of the present invention, Z ９ ~Z １６ is a sulfur atom. ９ ~Y １２ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (6a) and (6b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0158] A preferred group of compounds having the skeleton (6a) includes compounds represented by the following general formula (6a):

[0159] In general formula (6a), R ５９ and R ６０ Each of m59 and m60 independently represents an integer of 0 to 4. Y ９ and Y１０ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ９ ~Z １２ each independently represents an oxygen atom or a sulfur atom. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５９ , R ６０ , m59, m60, Z ９ ~Z １２ , A １ , A ２ For details, see R in general formula (5a). ５５ , R ５６ , m55, m56, A １ , A ２ and Z in skeleton (6a) ９ ~Z １２ The following description can be referred to.

[0160] Specific examples of compounds represented by general formula (6a) are listed below. The compounds of general formula (6a) that can be used in the present invention are not limited to the specific examples below. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0161] A preferred group of compounds having the skeleton (6b) includes compounds represented by the following general formula (6b):

[0162] In general formula (6b), R ６１ and R ６２ Each of m61 and m60 independently represents an integer of 0 to 4. Y １１ and Y １２are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １３ ~Z １６ each independently represents an oxygen atom or a sulfur atom. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ６１ , R ６２ , m61, m62, Z １３ ~Z １６ , A １ , A ２ For details, see R in general formula (6a). ５９ , R ６０ , m59, m60, A １ , A ２ and Z in skeleton (6b) １３ ~Z １６ The description can be referred to.

[0163] Specific examples of compounds represented by general formula (6b) are listed below. The compounds of general formula (6b) that can be used in the present invention are not limited to the specific examples below. Regarding specific examples containing X, compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0164] Preferred examples of such compounds include compounds in which a benzene ring is fused to the benzene ring to which a boron atom is not directly bonded, out of the two benzene rings constituting the carbazole partial structure present in general formula (G). Examples of such compounds include a compound having the following skeleton (7a) and a compound having the following skeleton (7b).

[0165] In skeletons (7a) and (7b), Y ２１ ~Y ２４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y.２１ ~Y ２４ For details, see Y in skeletons (4a) and (4b). １ ~Y ４ In one embodiment of the present invention, each hydrogen atom in the skeletons (7a) and (7b) is substituted with a linking group together with the adjacent hydrogen atom to form a ring structure.

[0166] A preferred group of compounds having the skeleton (7a) includes compounds represented by the following general formula (7a):

[0167] In the general formula (7a), Ar ７１ ~Ar ７４ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n71 and n73 each independently represent an integer of 0 to 2. n72 and n74 each independently represent an integer of 0 to 4. Y ２１ and Y ２２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n71 to n74 are integers of 0 to 2. In one embodiment of the present invention, n71 and n73 are the same number, and n72 and n74 are the same number. n71 to n74 may be the same number. For example, n71 to n74 may be 0. All of n71 to n74 may be 1. Also, for example, n71 and n73 may be 0, and n72 and n74 may be 1. Ar ７１ ~Ar ７４ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ , A １ , A ２ Reference can be made to the corresponding description in

[0168] Specific examples of the compound represented by general formula (7a) are listed below. The compounds of general formula (7a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0169] A preferred group of compounds having the skeleton (7b) includes compounds represented by the following general formula (7b):

[0170] In the general formula (7b), Ar ７５ ~Ar ７８ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n75 and n77 each independently represent an integer of 0 to 2. n76 and n78 each independently represent an integer of 0 to 4. Y ２３ and Y ２４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed description of n75 to n78, please refer to the descriptions of n71 to n74 in general formula (7a) in order. ７５ ~Ar ７８ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ Reference can be made to the corresponding description in

[0171] Specific examples of the compound represented by general formula (7b) are listed below. The compounds of general formula (7b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0172] Preferred examples of such compounds include compounds in which a benzene ring is fused to the benzene ring directly bonded to a boron atom, out of the two benzene rings constituting the carbazole partial structure present in general formula (G). Examples of such compounds include a compound having the following skeleton (8a) and a compound having the following skeleton (8b).

[0173] In skeletons (8a) and (8b), Y ２５ ~Y ２８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y. ２５ ~Y ２８ For details of the skeletons (4a) and (4b), please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (8a) and (8b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0174] A preferred group of compounds having the skeleton (8a) includes compounds represented by the following general formula (8a):

[0175] In the general formula (8a), Ar ７９ and Ar ８０ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ７１ and R ７２ Each of m71 and m72 independently represents an integer of 0 to 4. Each of n79 and n80 independently represents an integer of 0 to 4. Y ２５ and Y ２６ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n79 and n80 are integers of 0 to 2. In one embodiment of the present invention, n79 and n80 are the same number, and for example, both may be 0 or both may be 1. In one embodiment of the present invention, m71 and m72 are integers of 0 to 2. In one embodiment of the present invention, m71 and m72 are the same number, and for example, both may be 0 or both may be 1. Ar ７９ , Ar ８０ , R７１ , R ７２ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0176] Specific examples of the compound represented by general formula (8a) are listed below. The compounds of general formula (8a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0177] A preferred group of compounds having the skeleton (8b) includes compounds represented by the following general formula (8b):

[0178] In the general formula (8b), Ar ８１ and Ar ８２ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ７３ and R ７４ Each of m73 and m74 independently represents an integer of 0 to 4. Each of n81 and n82 independently represents an integer of 0 to 4. Y ２７ and Y ２８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ Each of m73, m74, n81, and n82 independently represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed description of m73, m74, n81, and n82, please refer to the descriptions of m71, m72, n79, and n80 in general formula (8a). Ar ８１ , Ar ８２ , R ７３ , R ７４ , A １ , A２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0179] Specific examples of the compound represented by general formula (8b) are listed below. The compounds of general formula (8b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0180] Preferred examples of such compounds include compounds having a benzene ring fused to both of the two benzene rings constituting the carbazole moiety present in general formula (G). Examples of such compounds include a compound having the following skeleton (9a) and a compound having the following skeleton (9b).

[0181] In skeletons (9a) and (9b), Y ２９ ~Y ３２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y. ２９ ~Y ３２ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (9a) and (9b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0182] A preferred group of compounds having the skeleton (9a) includes compounds represented by the following general formula (9a):

[0183] In general formula (9a), R ７５ and R ７６ Each of m75 and m76 independently represents an integer of 0 to 4. Y ２９ and Y ３０ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ７５ , R ７６ , m75, m76, A １ , A ２ For details, see R in general formula (8a). ７１ , R ７２ , m71, m72, A １ , A ２ The following description can be referred to.

[0184] Specific examples of the compound represented by general formula (9a) are listed below. The compounds of general formula (9a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0185] A preferred group of compounds having the skeleton (9b) includes compounds represented by the following general formula (9b):

[0186] In general formula (9b), R ７７ and R ７８ Each of m77 and m78 independently represents an integer of 0 to 4. Y ３１ and Y ３２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ７７ , R ７８ , m77, m78, A １ , A ２ For details, see R in general formula (8a). ７１ , R ７２ , m71, m72, A １ , A ２ The following description can be referred to.

[0187] Specific examples of the compound represented by general formula (9b) are listed below. The compounds of general formula (9b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0188] Compounds represented by general formula (G) are also preferably compounds containing four or more carbazole moieties in the molecule. Examples of such compounds include compounds having the following skeleton (10):

[0189] Each hydrogen atom in the skeleton (10) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (G). １ ~R ２６ , A １ , A ２ can be referred to. At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in the skeleton (10) is substituted with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeleton (10) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0190] A preferred group of compounds having the skeleton (10) includes compounds represented by the following general formula (10):

[0191] In the general formula (10), Ar ９１ ~Ar ９４each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n91 and n93 each independently represent an integer of 0 to 4, and n92 and n94 each independently represent an integer of 0 to 3. The α ring, β ring, γ ring, and δ ring may be substituted, and at least one ring is substituted with a substituted or unsubstituted aryl group, or is fused with an optionally substituted benzene ring, or is fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n91 to n94 are integers of 0 to 2. In one embodiment of the present invention, n91 and n93 are the same number, and n92 and n94 are the same number. n91 to n94 may all be the same number, for example, all may be 0 or all may be 1. Ar ９１ ~Ar ９４ As for the preferred group, Ar in general formula (1a) １ ~Ar ４Reference can be made to the corresponding description in the above. In one embodiment of the present invention, the α-ring and the γ-ring have the same substituent or the same fused structure, and the β-ring and the δ-ring have the same substituent or the same fused structure. In one embodiment of the present invention, the β-ring and the δ-ring are both substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. In one embodiment of the present invention, the α-ring and the γ-ring are both substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. In one embodiment of the present invention, all of the α-ring, the β-ring, the γ-ring, and the δ-ring are substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. A １ and A ２ For the explanation and preferred range of , the corresponding description of general formula (G) can be referred to.

[0192] Specific examples of the compound represented by general formula (10) are given below. The compounds of general formula (10) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0193] The compound represented by general formula (G) may have an asymmetric skeleton, for example, a compound having an asymmetric skeleton such as the following skeleton (11a) or skeleton (11b).

[0194] In the skeletons (11a) and (11b), Z １７ and Z １８ each independently represents an oxygen atom or a sulfur atom. In one embodiment of the present invention, each hydrogen atom in the skeletons (11a) and (11b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0195] A preferred group of compounds having the skeleton (11a) includes compounds represented by the following general formula (11a):

[0196] In the general formula (11a), Ar ８３ ~Ar ８５ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ８３ and R ８４ Each of Z independently represents a substituted or unsubstituted alkyl group. １７ represents an oxygen atom or a sulfur atom. m83 and m84 each independently represent an integer of 0 to 5. n83 represents an integer of 0 to 4, and n84 and n85 each independently represent an integer of 0 to 3. Ar ８３ ~Ar ８５ , R ８３ , R ８４ For detailed explanations and preferred ranges of m83, m84, and n83 to n85, see Ar １ , Ar ２ , Ar ４ , R ４１ , R ４２ , m1, m2, n1, n2, and n4.

[0197] Specific examples of the compound represented by general formula (11a) are given below. The compounds of general formula (11a) that can be used in the present invention are not limited to the following specific examples. In the following specific examples, a compound in which all X's in the molecule are oxygen atoms and a compound in which all X's in the molecule are sulfur atoms are respectively disclosed. A compound in which some of the X's in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0198] A preferred group of compounds having the skeleton (11b) includes compounds represented by the following general formula (11b):

[0199] In the general formula (11b), Ar ８６ ~Ar ８８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ８６ and R ８７ Each of Z independently represents a substituted or unsubstituted alkyl group. １８ represents an oxygen atom or a sulfur atom. m86 and m87 each independently represent an integer of 0 to 5. n86 represents an integer of 0 to 4, and n87 and n88 each independently represent an integer of 0 to 3. Ar ８６ ~Ar ８８ , R ８６ , R ８７ For detailed explanations and preferred ranges of m86, m87, and n86 to n88, see Ar １ , Ar ２ , Ar ４ , R ４１ , R ４２ , m1, m2, n1, n2, and n4.

[0200] Specific examples of the compound represented by general formula (11b) are listed below. The compounds of general formula (11b) that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are respectively disclosed. A compound in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0201] As the compound represented by general formula (G), R ５ A compound in which R is a donor group can be preferably used. ５ A compound in which R is a donor group tends to have a high molar absorption coefficient and high luminous efficiency. ３ In a preferred embodiment of the present invention, R ３ is not a donor group. In a preferred embodiment of the present invention, R １ ~R７ Among them, R ５ Only R is a donor group, or none of R is a donor group (particularly a donor group with a σp value of −0.2 or less). A donor group is a group with a negative Hammett σp value. ５ The donor group preferably has a σp value of −0.2 or less, for example, −0.4 or less, or for example, −0.6 or less. A preferred donor group is a substituted amino group, preferably a substituted or unsubstituted diarylamino group. The aryl group may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after condensation is preferably 2 to 6, for example, selected from 2 to 4, or may be 2. The two aryl groups constituting the diarylamino group may be the same or different. Furthermore, the two aryl groups may be linked by a single bond or a linking group. A preferred substituted or unsubstituted diarylamino group is a substituted or unsubstituted diphenylamino group. A substituted or unsubstituted carbazol-9-yl group in which two phenyl groups are bonded by a single bond may be used, or a substituted or unsubstituted diphenylamino group in which two phenyl groups are not bonded by a single bond may be used. R in general formula (G) １ ~R ７ When any of R is a substituted amino group, at least R ５ is preferably a substituted amino group, and R ５ More preferably, only R is a substituted amino group. ３ is not a substituted amino group. ５ is a donor group, and X １ is a nitrogen atom, R １６ or R １９ is preferably a donor group, and R １９ is more preferably a donor group. １ ~R ２６ may be, for example, all hydrogen atoms or all deuterium atoms, or, for example, R ３ , R ６ , R １５ , R ２０At least one of R may be a substituent (preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group), and the others may be hydrogen atoms or deuterium atoms. ５ is a donor group, and X １ is a boron atom, R ２０ or R ２３ is preferably a donor group, and R ２０ is more preferably a donor group. １ ~R ２６ may be, for example, all hydrogen atoms or all deuterium atoms, or, for example, R ３ , R ６ , R １９ , R ２４ At least one of R may be a substituent (preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group), and the others may be hydrogen atoms or deuterium atoms. ５ As a preferred group of compounds in which is a donor group, there can be mentioned compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b):

[0202] In the general formula (12a) and the general formula (12b), Ar １ ~Ar ８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group can be preferably selected. ５ represents a donor group. ４１ ~R ４４ each independently represents a substituted or unsubstituted alkyl group. m1 to m4 each independently represents an integer of 0 to 5. n1, n3, n5, and n7 each independently represent an integer of 0 to 4, n4 and n8 each independently represent an integer of 0 to 3, and n2' and n6' each independently represent an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ ~Ar ８ , R４１ ~R ４４ , m1-m4, n1, n3-n5, n7, n8, A １ , A ２ For details of the formula (1a) and the formula (1b), the corresponding descriptions can be referred to. However, Ar bonded to adjacent carbon atoms １ Ar bonded to adjacent carbon atoms ３ Ar bonded to adjacent carbon atoms ５ Ar bonded to adjacent carbon atoms ７ They may be bonded to each other to form a ring structure, preferably a benzofuran (fused with a furan ring) or a benzothiophene (fused with a thiophene ring).

[0203] Specific examples of compounds represented by general formula (12a) and general formula (12b) are listed below. However, the compounds of general formula (12a) and general formula (12b) that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, the structure of each compound is defined by specifying R, Ar, and X in formulas F1 to F56 in the table. R is selected from A to D listed below, Ar is selected from a to d listed below, and X is selected from α to γ. For example, compound No. 1 in the table is a compound having a structure in which R is A and Ar is a in formula F1.

[0204]

[0205]

[0206] In one embodiment of the present invention, the above skeletons (1a) to (12b) are skeletons to which no other ring is further fused. In another embodiment of the present invention, the above skeletons (1a) to (12b) are skeletons to which another ring may be further fused. The other rings referred to here are those defined by the above R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ The description of the cyclic structure formed by bonding together can be referred to.

[0207] In one embodiment of the present invention, A of general formula (G) １ and A ２ is an acceptor group. For example, A １ and A ２ is an acceptor group, and examples thereof include compounds having any of the skeletons (1a) to (12b). For details and specific examples of the acceptor group, see A in the above general formula (G). １ and A２ The explanation and specific examples of the acceptor group in the above can be referred to. １ and A ２ Specific examples of compounds in which A is an acceptor group are as follows: １ and A ２ The compounds in which A is an acceptor group are not to be construed as being limited by the following specific examples. １ and A ２ have a structure in which both are "A", and the structure of each compound is specified by individually specifying the "A".

[0208] In one embodiment of the present invention, a compound having a rotationally symmetric structure is selected as the compound represented by general formula (G). In one embodiment of the present invention, a compound having an axisymmetric structure is selected as the compound represented by general formula (G). In one embodiment of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (G). Specific examples of compounds having an asymmetric skeleton are listed below. Compounds having an asymmetric skeleton or compounds having an asymmetric structure that can be used in the present invention should not be construed as being limited by the specific examples below. As specific examples containing X, compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are respectively disclosed. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0209] Specific examples of compounds that have a symmetrical skeleton but have an asymmetrical structure due to asymmetrically bonded substituents are given below. The compounds having an asymmetrical structure that can be used in the present invention should not be construed as being limited by the following specific examples.

[0210] In one embodiment of the present invention, R ３ is not a diarylamino group (two aryl groups constituting the diarylamino group may be bonded to each other). In a preferred embodiment of the present invention, R ３ is a hydrogen atom, a deuterium atom, or an acceptor group (not a donor group). In one embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or greater. In a preferred embodiment of the present invention, at least one of m1 and m2 in general formula (1a) is 1 or greater. In a further preferred embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or greater, and at least one of m1 and m2 in general formula (1a) is 1 or greater. In one embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or greater. In a preferred embodiment of the present invention, at least one of m3 and m4 in general formula (1b) is 1 or greater. In a further preferred embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or greater, and at least one of m3 and m4 in general formula (1a) is 1 or greater. When at least one of m1 and m2 is 1 or more, and at least one of m3 and m4 is 1 or more, R ４１ and R ４２ At least one of and R ４３ and R ４４ At least one of R is preferably an alkyl group optionally substituted with a deuterium atom, for example, R ４１ ~R ４４ When at least one of n1 to n4 is 1 or more and at least one of n5 to n8 is 1 or more, Ar １ ~Ar ４ and Ar ５ ~Ar ８ At least one of the groups is preferably an aryl group which may be substituted with a deuterium atom or an alkyl group, for example, Ar １ ~Ar ８ In one embodiment of the present invention, all of X in general formula (G) are aryl groups which may be substituted with a deuterium atom or an alkyl group. １is a boron atom and R ８ , R １０ , R １２ , R １３ , R １５ , R １７ is an alkyl group (or a methyl group), R １ ~R ７ , R １８ ~R ２０ , R ２３ ~R ２６ At least one of X in general formula (G) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. ２ is a boron atom and R ８ , R １０ , R １２ , R ２２ , R ２４ , R ２６ is an alkyl group (or a methyl group), R １ ~R ７ , R １３ ~R １６ , R １９ ~R ２１ At least one of X in general formula (G) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. １ is a boron atom, and R ８ and R ９ , R ９ and R １０ and R １５ and R １６ , R １６ and R １７ When any pair of these is bonded to each other to form an aromatic ring (or a benzene ring), R １ ~R ７ , R １８ ~R ２０ , R ２３ ~R ２６ At least one of X in general formula (G) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. ２ is a boron atom, and R ８ and R９ , R ９ and R １０ and R ２２ and R ２３ , R ２３ and R ２４ When any pair of these is bonded to each other to form an aromatic ring (or a benzene ring), R １ ~R ７ , R １３ ~R １６ , R １９ ~R ２１ At least one of R in general formula (G) is a substituent, preferably a group in the substituent group E, for example, an aryl group optionally substituted with a deuterium atom or an alkyl group. ９ and R １１ is neither a cyano group nor an alkyl group. ９ and R １１ is a hydrogen atom, a deuterium atom, or a substituent other than a cyano group and an alkyl group. ９ and R １１ is neither a cyano group nor a tert-butyl group. ８ ~R １２ In one embodiment of the present invention, at least one of R in general formula (G) is a substituent. ３ is not a substituted amino group or an aryl group. ３ is not a substituted amino group or a phenyl group. ３ is not a dimethylamino group, a diphenylamino group, or a phenyl group. １ ~R ２６ At least one of R is a substituent, and more preferably R １ ~R ２６ At least one of the groups is an alkyl group, for example, an alkyl group having 1 to 4 carbon atoms.

[0211] (Substrate) In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, and the substrate is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0212] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0213] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O ３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0214] Injection Layer The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, the injection layer is present. In some embodiments, the injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials.

[0215]

[0216] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0217] (Barrier Layer) A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the term "electron blocking layer" or "exciton blocking layer" includes a layer that has both the functions of an electron blocking layer and an exciton blocking layer.

[0218] (Hole Blocking Layer) The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material used for the hole blocking layer may be the same material as described above for the electron transporting layer. Below are examples of preferred compounds that can be used for the hole blocking layer.

[0219]

[0220] (Exciton Blocking Layer) The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0221] (Hole Transport Layer) The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0222]

[0223] Electron Transport Layer The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0224]

[0225] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0226]

[0227] While specific examples of preferred materials that can be used in organic electroluminescent devices have been given, the materials that can be used in the present invention are not limited to the exemplified compounds. Furthermore, even compounds exemplified as materials having specific functions can be used as materials having other functions. Each organic layer of an organic electroluminescent device can be formed by a wet process. In the wet process, a solution containing a composition containing compounds constituting the organic layer is applied to a surface, and a layer is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the compounds constituting the organic layer is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compounds constituting the organic layer. In some embodiments, the organic layer can be formed by a dry process. In some embodiments, the dry process can be a vacuum deposition method, but is not limited to this. When using vacuum deposition, the compounds constituting the organic layer may be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When using a single deposition source, a mixed powder of compound powders may be used, a compressed compact of the mixed powder may be used, or a mixture of the compounds may be used by heating, melting, and cooling the mixture. In some embodiments, co-deposition is performed under conditions where the deposition rates (weight loss rates) of the multiple compounds contained in a single deposition source are identical or nearly identical, thereby forming an organic layer having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the organic layer to be formed as a deposition source, an organic layer having the desired composition ratio can be easily formed. In some embodiments, the temperature at which the weight loss rate of each co-deposited compound is the same can be identified, and that temperature can be used as the temperature during co-deposition.

[0228] Devices. In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0229] Bulb or Lamp In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0230] Displays or Screens In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0231] [Device Manufacturing Method] OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0232] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0233] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0234] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0235] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0236] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0237] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0238] The features of the present invention will be explained in more detail below with reference to synthesis examples and working examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334 model).

[0239] (Synthesis Example 1) Synthesis of Compound 1b

[0240] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (2 g, 6.19 mmol), 3-phenyl-12H-benzofuro[2,3-a]carbazole (2.06 g, 6.19 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.57 g, 0.62 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.36 g, 1.24 mmol), and sodium tert-butoxide (1.19 g, 12.4 mmol) were added to 45 mL of toluene and refluxed for 24 hours. The reaction solution was cooled to room temperature, and chloroform was added. The resulting organic layer was washed twice with water, dried over magnesium sulfate, and the solvent was removed. The resulting solid was purified by silica gel column chromatography (developing solvent: chloroform / n-hexane = 5:5). Further recrystallization (toluene / methanol) yielded compound 1b (1.74 g, 49%) as a white solid. 1 H NMR (400MHz, CDCl3, δ): 8.43 (s, 1H), 8.32 (s, 1H), 8.11 (d, J = 8 Hz, 1H), 8.07 (m, 2H), 7.94-7.82 (m, 4H), 7.77-7.68 (m, 6H), 7.65 (d, J = 8 Hz, 1H), 7.58 (d, J= 8 Hz, 1H), 7.55-7.31 (m, 8H). MS (ASAP): 576.12 (M+H + ). Calcd for C 42 H 25 NO2: 575.91.

[0241] (Synthesis Example 2) Synthesis of Compound 2b

[0242] N-Bromosuccinimide (13.8 g, 77.7 mmol) was added to a chloroform solution (900 mL) of 12H-benzofuro[2,3-a]carbazole (20.0 g, 77.7 mmol) under a nitrogen atmosphere and ice bath, and the mixture was allowed to warm to room temperature and stirred for 14 hours. After removing the solvent, the mixture was washed with methanol. The resulting solid was dissolved in heated toluene and filtered through a Buchner funnel lined with Celite / silica gel / Celite. After removing the solvent from the filtrate, the mixture was recrystallized from toluene and chlorobenzene, respectively, to obtain Intermediate M1 (15.9 g, 61%) as a white solid. 1 H-NMR (400 MHz, CDCl3, δ): 8.63 (d, J=6.8 Hz, 1H), 8.52 (br, 1H), 8.19 (s, 1H), 8.11 (d, J = 7.6 Hz, 1H), 7.67 (d, J = 7.6 Hz, 1H), 7.57-7.43 (m, 4H), 7.31 (t, J = 7.2 Hz, 1H) MS (ASAP): 335.96 (M+H + ). Calcd for C 18 H 10 BrNO: 334.99

[0243]

[0244] Under a nitrogen atmosphere, a solution of intermediate M1 (15.8 g, 46.9 mmol), phenylboronic acid (6.8 g, 56.3 mmol), tripotassium phosphate (19.9 g, 93.9 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.7 g, 2.3 mmol) in 1,4-dioxane (470 mL) / ultrapure water (150 mL) was stirred at 100°C for 15 hours. After removing the dioxane, the solid precipitated in the water was filtered. The resulting solid was dissolved in heated toluene and filtered through a Buchner funnel lined with Celite / silica gel / Celite. The solvent was removed from the filtrate, and the product was recrystallized from toluene and chlorobenzene, respectively, to obtain intermediate M2 (10.8 g, 69%). 1H-NMR (400 MHz, CDCl3, δ): 8.54 (s, 1H), 8.13 (d, J = 6.8 Hz, 1H), 7.93 (s, 1H), 7.72 (dt, J = 6.8 Hz, 2 Hz 2H), 7.65 (d, J = 8.4 Hz, 1H), 7.59-7.46 (m, 6H), 7.41 (td, J = 7.8 Hz, 1.2 Hz, 1H), 7.30 (td, J = 7.6 Hz, 1.2 Hz, 1H), 7.16 (td, J= 7.6 Hz, 1.2 Hz, 1H) MS (ASAP): 334.44 (M+H + ). Calcd for C 24 H 15 NO: 333.12

[0245]

[0246] Under a nitrogen atmosphere, a toluene solution (240 mL) of 2-(3-bromophenyl)dibenzofuran (10.6 g, 32.7 mmol), intermediate M2 (10.9 g, 32.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.0 g, 3.2 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.9 g, 6.5 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) was stirred at 130°C for 14 hours. Toluene was added to the reaction solution, and the mixture was filtered through a Buchner funnel lined with Celite / silica gel / Celite. After removing the solvent, the mixture was washed with ethyl acetate and filtered to obtain a brown solid. The resulting solid was recrystallized from chlorobenzene and toluene to obtain compound 2b (12.4 g, 65%). 1H NMR (400MHz, CDCl3, δ): 8.32 (d, J = 2.0 Hz, 1H), 8.22 (d, J = 8.0 Hz, 1H), 8.07 (d, J = 1.7 Hz, 1H), 8.04 (s, 1H), 7.89-7.83 (m, 3H), 7.78-7.73 (m, 4H), 7.66 (d, J = 8.4 Hz, 2H), 7.61-7.57 (m, 3H), 7.54-7.44 (m, 5H), 7.38-7.30 (m, 3H), 7.17-7.13 (td, J= 7.4 Hz, 1.2 Hz, 1H) MS (ASAP): 576.37 (M+H + ). Calcd for C 42 H 25 NO2: 575.19.

[0247] (Synthesis Example 3) Synthesis of Compound 6b

[0248] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (1.78 g, 5.5 mmol), 2-phenyl-12H-benzofuro[2,3-a]carbazole (2.2 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (5.03 g, 0.55 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.319 g, 1.1 mmol), and sodium tert-butoxide (1.59 g, 16.5 mmol) were added to 50 mL of toluene and refluxed for 24 hours. The reaction solution was cooled to room temperature, and chloroform was added. The resulting organic layer was washed twice with water, dried over magnesium sulfate, and the solvent was removed. The resulting solid was purified by silica gel column chromatography (developing solvent: chloroform / n-hexane = 3:7). Further recrystallization (toluene / methanol) afforded compound 6b (2.24 g, 77%) as a white solid. 1H NMR (400MHz, CDCl3, δ): 8.32 (d, J = 2 Hz, 1H), 8.28 (d, J = 8 Hz, 1H), 8.18 (d, J = 8 Hz, 1H), 8.09-8.06 (m, 2H), 7.93 (d, J = 8 Hz, 1H), 7.88-7.82 (m, 3H), 7.79-7.75 (m, 2H), 7.71-7.58 (m, 5H), 7.54-7.31 (m, 10H). MS (ASAP): 576.33 (M+H + ). Calcd for C 42 H 25 NO2: 575.91.

[0249] (Synthesis Example 4) Synthesis of Compound 19b

[0250] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (0.97 g, 3 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (1 g, 3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.27 g, 0.3 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.17 g, 0.6 mmol), and sodium tert-butoxide (0.58 g, 6 mmol) were added to 15 mL of toluene and refluxed for 24 hours. The reaction solution was cooled to room temperature, and chloroform was added. The resulting organic layer was washed twice with water, dried over magnesium sulfate, and the solvent was removed. The resulting solid was purified by silica gel column chromatography (developing solvent: chloroform / n-hexane = 2:8). Further recrystallization (toluene / methanol) afforded compound 19b (1.09 g, 63%) as a white solid. 1 H NMR (400MHz, CDCl3, δ): 8.81 (s, 1H), 8.24 (s, 1H), 8.02-7.97 (m, 4H), 7.88-7.72 (m, 7H), 7.69-7.33 (m, 12H). MS (ASAP): 575.21(M+H) + ). Calcd for C 42 H 25 NO2: 575.91.

[0251] (Example 1) On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, the following thin films were deposited by vacuum deposition at a vacuum degree of 5.0 × 10 －５ An organic electroluminescence device was fabricated by laminating the layers at 100 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, and compound 1b was further formed thereon to a thickness of 10 nm. Next, the host material (H1) and the delayed fluorescent material (T132) were co-deposited from different evaporation sources to form a 40 nm thick layer as an emitting layer. At this time, the content of the host material was 65% by mass, and the content of the delayed fluorescent material was 35% by mass. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The contents of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, and an organic electroluminescence device was fabricated. This element was designated EL element 1. Furthermore, organic electroluminescence elements were fabricated by the same procedure except that compounds 6b, 19b, and 22 were used instead of compound 1b, and were designated EL elements 2 to 4, respectively. Furthermore, organic electroluminescence elements were fabricated by the same procedure except that comparative compound A and comparative compound B were used instead of compound 1b, and were designated comparative EL element 1 and comparative EL element 2, respectively. When a current was applied to each of the fabricated organic electroluminescence elements, delayed fluorescence derived from the delayed fluorescence material (T132) was observed. Each organic electroluminescence element was subjected to a current density of 12.6 mA / cm ２ The device was driven at 400 V, and the time (LT95) until the luminous intensity reached 95% of that at the start of driving was measured. The measurement results are shown in Table 2. The LT95 in Table 2 is shown as a relative value when the LT95 of Comparative EL Device 2 is set to 1. The measurement results show that the device lifetime is significantly longer when the compound represented by general formula (1) is used as the electron-blocking material than when Comparative Compound A or Comparative Compound B, which have conventionally been used as electron-blocking materials, are used.

[0252]

[0253] (Example 2) An organic electroluminescence element was fabricated by the same procedure as in Example 1, except that the emitting layer in Example 1 was replaced with a 40 nm thick emitting layer in which the host material (H1), the delayed fluorescent material (T132), and the fluorescent material (E1) were co-deposited from different evaporation sources, with the contents being 64.2 mass%, 35.0 mass%, and 0.8 mass%, respectively. This element was designated EL element 5. Organic electroluminescence elements fabricated by the same procedure, except that compounds 2b and 19b were used instead of compound 1b, were designated EL elements 6 and 7, respectively. When electricity was applied to each of the fabricated organic electroluminescence elements, delayed fluorescence derived from the fluorescent material (E1) was observed. The fabricated organic electroluminescence elements were subjected to a current of 6.3 mA / cm ２ The external quantum efficiency (EQE) and initial driving voltage were measured by driving each organic electroluminescence device at a current density of 12.6 mA / cm ２ The EL element was driven at 100 V, and the time (LT95) until the luminous intensity reached 95% of that at the start of driving was measured. The measurement results are shown in Table 3. The EQE and LT95 in Table 3 are shown as relative values ​​when the LT95 of EL element 7 is set to 1, and the driving voltage is shown as a relative value when EL element 7 is set to the reference (0). The measurement results show that even when a host material, a delayed fluorescent material, and a fluorescent material are used in the emitting layer, all of the elements using the compound represented by general formula (1) as the electron blocking material have high luminous efficiency, low driving voltage, and long element life.

[0254]

[0255] (Example 3) An organic electroluminescence element was fabricated by the same procedure as in Example 1, except that the emitting layer in Example 1 was replaced with a 40 nm thick emitting layer in which the host material (H1) and the delayed fluorescent material (T136) were co-deposited from different evaporation sources and the contents were 65% by mass and 35% by mass, respectively. This element was designated EL element 8. An organic electroluminescence element was fabricated by the same procedure except that compound 2b was used instead of compound 1b, and was designated EL element 9. When a current was applied to each of the fabricated organic electroluminescence elements, delayed fluorescence derived from the delayed fluorescent material (T136) was observed. The fabricated organic electroluminescence elements were powered at 6.3 mA / cm ２ The external quantum efficiency (EQE) and initial driving voltage were measured by driving each organic electroluminescence device at a current density of 12.6 mA / cm. ２ The EL element was driven at 100 Hz, and the time (LT95) until the luminous intensity reached 95% of that at the start of driving was measured. The measurement results are shown in Table 4. The EQE and LT95 in Table 4 are shown as relative values ​​when the LT95 of EL element 9 is set to 1, and the driving voltage is shown as a relative value when EL element 9 is set to the reference (0). The measurement results show that even when a delayed fluorescent material different from that in Example 1 was used, all of the elements using the compound represented by general formula (1) as the electron blocking material had high luminous efficiency, low driving voltage, and long element life.

[0256]

[0257] Example 4 On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, the following thin films were deposited by vacuum deposition at a vacuum degree of 5.0×10 －５An organic electroluminescence device was fabricated by laminating the layers at 1000 Pa. First, HAT-CN was formed to a thickness of 60 nm on ITO, TrsPCz was formed to a thickness of 30 nm on top of that, and PYD2Cz was formed to a thickness of 5 nm on top of that. Next, a host material (reference compound a) and a delayed fluorescent material (T3) were co-deposited from different evaporation sources to form a 30 nm thick layer as an emitting layer. At this time, the content of the host material was 70% by mass, and the content of the delayed fluorescent material was 30% by mass. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The contents of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby preparing an organic electroluminescence device. This device was designated Reference EL Device 1. The prepared organic electroluminescence device was subjected to a current flow of 2 mA / cm. ２ The external quantum efficiency (EQE) was measured by driving the device at 2 mA / cm and showed a high value of 21.9%. This indicates that Reference Compound a is an excellent material as a host material. Meanwhile, an organic electroluminescence device was fabricated using the same procedure except that Compound 1a was used instead of PYD2Cz, and this was designated Reference EL Device 2. The fabricated organic electroluminescence device was driven at 2 mA / cm and the external quantum efficiency (EQE) was measured. This indicates that Reference Compound a is an excellent material as a host material. ２ The external quantum efficiency (EQE) was measured by driving the device at 1000 V, and the result was a decrease to 17.1%. This indicates that Reference Compound a is not suitable as an electron-blocking material. The above results indicate that even useful host materials are not useful as electron-blocking materials, suggesting that it is not easy to find useful electron-blocking materials.

[0258] The compound represented by general formula (1) is useful as an electron blocking material and can be used in organic semiconductor devices. When the compound of the present invention is used in the electron blocking layer of an organic electroluminescence device, the device life can be extended. Therefore, the present invention has high industrial applicability.

Claims

1. An electron blocking material comprising a compound represented by the following general formula (1): 【Chemistry 1】 [In the formula, R １ R 2 , R 4 and R 5 each independently represent one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group combining two or more of these. R 3 represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group having 6 to 10 carbon atoms, or a group combining two or more of these. R １ ~R ５ is another R １ ~R ５ Alternatively, the Ar group does not bond to form a ring structure, but the adjacent R ３ may be bonded to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2. X represents an oxygen atom or a sulfur atom. Ar represents a monocyclic arylene group or a monocyclic heteroarylene group, and the monocyclic arylene group and the monocyclic heteroarylene group may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group combining two or more of them. In the general formula (1), the dibenzofuran is bonded to Ar at the 2-position.]

2. The electron blocking material according to claim 1 , wherein the compound has a structure represented by the following general formula (2B): 【Chemistry 2】 [In the formula, R １ R 2 , R 4 , R 5 and R 6 each independently represent one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group consisting of two or more of them. R 3 represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group having 6 to 10 carbon atoms, or a group consisting of two or more of them. R １ ~R ６ is another R １ ~R ６ Although it does not form a ring structure by bonding with adjacent R ３ may be bonded to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. X represents an oxygen atom or a sulfur atom.]

3. The electron blocking material according to claim 1 , wherein the compound has a structure represented by the following general formula (3): 【Chemistry 3】 [In the formula, R １ R 2 , R 4 , R 5 and R 6 each independently represent one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group consisting of two or more of them. R 3 represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group having 6 to 10 carbon atoms, or a group consisting of two or more of them. R １ ~R ６ is another R １ ~R ６ Although it does not form a ring structure by bonding with adjacent R ３ may be bonded to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. However, n1+n3+n4+n5 is 1 or more. R １ and R ３ ~R ５ One or two of the above represent an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom. The dibenzofuran in the general formula (3) is bonded at the 2-position to the benzene ring to which (R 6 ) n6 is bonded.]

4. The electron blocking material of claim 2 , wherein n1, n2, and n6 are 0.

5. 2. The electron blocking material of claim 1, wherein n3 to n5 are each independently 0 or 1.

6. 2. The electron blocking material of claim 1 having any of the following structures: 【Chemistry 4】

7. 2. The electron blocking material according to claim 1 for use in combination with a compound represented by the following general formula (G): General formula (G) 【Chemistry 5】 [In the general formula (G), X １ and X ２ is a nitrogen atom and the other is a boron atom. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring.

8. An organic semiconductor device comprising the electron blocking material according to any one of claims 1 to 6.

9. 9. The organic semiconductor device according to claim 8, wherein the organic semiconductor device is an organic electroluminescence device having an anode, a cathode, and at least two organic layers including an electron blocking layer containing the electron blocking material and an emitting layer between the anode and the cathode.

10. The organic semiconductor device according to claim 9 , wherein the light-emitting layer comprises a host material and a delayed fluorescent material.

11. The organic semiconductor device according to claim 9 , wherein the light-emitting layer contains a host material, a delayed fluorescent material, and a fluorescent material, and the amount of light emitted from the device is greatest from the fluorescent material.

12. The organic semiconductor device according to claim 9 , wherein the light-emitting layer is adjacent to the electron blocking layer.

13. The organic semiconductor device according to claim 9 , wherein the light-emitting layer contains a compound represented by the following general formula (G): General formula (G) 【Chemistry 6】 [In the general formula (G), X １ and X ２ is a nitrogen atom and the other is a boron atom. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring.

14. The organic semiconductor device according to claim 9 , wherein the light-emitting layer contains a compound represented by the following general formula (4): 【Chemistry 7】 [In the general formula (4), R ２１ ~R ２３ one of them represents a cyano group or a group represented by the following general formula (5), R ２１ ~R ２３ The remaining two and R ２４ and R ２５ At least one of R represents a group represented by the following general formula (6): ２１ ~R ２５ the remainder represents a hydrogen atom or a substituent (provided that the substituent referred to here is not a cyano group, a group represented by the following general formula (5), or a group represented by the following general formula (6)). 【Chemistry 8】 [In the general formula (5), L １ represents a single bond or a divalent linking group; R ３１ and R ３２ each independently represents a hydrogen atom or a substituent, and * represents a bonding position. 【Chemistry 9】 [In the general formula (6), L ２ represents a single bond or a divalent linking group; R ３３ and R ３４ each independently represents a hydrogen atom or a substituent, and * represents a bonding position.

15. A compound represented by the following general formula (3): 【Chemistry 10】 [In the formula, R １ R 2 , R 4 , R 5 and R 6 each independently represent one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group consisting of two or more of them. R 3 represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group having 6 to 10 carbon atoms, or a group consisting of two or more of them. R １ ~R ５ is another R １ ~R ６ Although it does not form a ring structure by bonding with adjacent R ３ may be bonded to each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent an integer of 0 to 4, n2 and n6 each independently represent an integer of 0 to 3, and n4 represents an integer of 0 to 2. However, n1+n3+n4+n5 is 1 or more. R １ and R ３ ~R ５ One or two of the groups represent an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom. However, when n3+n4+n5 is 0, R １ is not an unsubstituted phenyl group. The dibenzofuran in general formula (3) is bonded at the 2-position to the benzene ring to which (R 6 ) n6 is bonded.]

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