Electron barrier materials, organic semiconductor devices, and compounds

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

[Technical Field]

[0001] This invention relates to a compound useful as an electron barrier material and an organic semiconductor device using the same compound. [Background technology]

[0002] Research is actively being conducted to improve the performance of organic semiconductor devices such as organic electroluminescent devices (organic EL devices). For example, to improve the device lifespan and driving voltage of organic electroluminescent devices, it is desirable to improve the function of charge transport-related materials such as electron transport materials, hole transport materials, electron barrier materials, and hole barrier materials. Therefore, the development and improvement of these materials are also progressing. For example, an electron barrier material is placed between the light-emitting layer and the hole transport layer. It prevents electrons present in the light-emitting layer from escaping to the hole transport layer, and also transports holes from the hole transport layer to the light-emitting layer. Using a superior electron barrier material improves the recombination probability of electrons and holes in the light-emitting layer, ultimately leading to an extension of the device's lifetime. Conventionally, various compounds have been proposed as electron barrier materials. For example, Patent Document 1 proposes a compound having the following structure.

[0003] [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] WO2010 / 140482 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] However, there is room for improvement in terms of device lifetime for organic electroluminescent devices using the above compounds as electron barrier materials. Therefore, the inventors of the present invention have intensively studied to provide an electron barrier material that can extend the device lifetime when used in organic electroluminescent devices.

Means for Solving the Problems

[0006] As a result of intensive studies, the inventors of the present invention have found that a compound having a specific structure functions as an excellent electron barrier material. The present invention is provided based on such findings, and specifically has the following configurations. [1] An electron barrier material containing a compound represented by the following general formula (1).

Chemical formula

Chemical formula

[10] The organic semiconductor element according to [9], wherein the organic semiconductor element has an anode, a cathode, and at least two organic layers between the anode and the cathode, the electron barrier layer and the electron-emitting layer comprising the electron barrier material.

[11] The organic semiconductor device according to

[10] , wherein the light-emitting layer comprises a host material and a delayed fluorescence material.

[12] The organic semiconductor device according to

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

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

[10] to

[12] , wherein the light-emitting layer is adjacent to the electron barrier layer.

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

[10] to

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

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

[10] to

[14] , wherein the light-emitting layer comprises a compound represented by the following general formula (4). [ka] [In 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 them represents a group represented by the following general formula (6), R 21 ~R 25 The remainder represents a hydrogen atom or a substituent (however, the substituent referred to here is not a cyano group, a group represented by general formula (5) below, or a group represented by general formula (6) below). [ka] [In general formula (5), L 1 represents a single bond or a divalent linking group, R 31 and R 32 Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position. [ka] [In general formula (6), L 2 represents a single bond or a divalent linking group, R 33 and R 34 Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position.

[16] The compound represented by the general formula (3) above. However, when n3+n4+n5 is 0, R 1 It is not an unsubstituted phenyl group. [Effects of the Invention]

[0007] Compounds represented by general formula (1) are useful as electron barrier materials and can be effectively used in organic semiconductor devices. For example, by using the compound of the present invention in the electron barrier layer of an organic electroluminescent device, the device lifespan can be extended. [Modes for carrying out the invention]

[0008] The contents of the present invention will be described in detail below. The descriptions of the constituent elements described below may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this application, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, in this application, "consists of" means consisting only of what is written before "consists of" and does not include anything else. Furthermore, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention are deuterium atoms ( 2 It can be substituted with H (deuterium D). In the chemical structural formulas herein, hydrogen atoms are represented as H or their representation is omitted. For example, when the representation of an atom bonded to a carbon atom in the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom in the ring skeleton where the representation is omitted. In this specification, the term "substituent" means an atom or group of atoms other than hydrogen atoms and deuterium atoms. On the other hand, the expressions "substituted or unsubstituted" and "may be substituted" mean that hydrogen atoms may be substituted with deuterium atoms or substituents. Furthermore, in this invention, "transparent" means that the transmittance of visible light is 50% or more, preferably 80% or more, more preferably 90% or more, and even more preferably 99% or more. The transmittance of visible light can be measured by an ultraviolet-visible spectrophotometer.

[0009] (Compounds represented by general formula (1)) In this invention, a compound represented by the following general formula (1) is used. [ka]

[0010] In general formula (1), R 1 ~R 5 Each of these independently represents a substituent that does not contain a deuterium atom or a cyano group. In one aspect of the present invention, R 1 ~R 5Each substituent is independently a substituent whose Hammett σp value is in the range of -0.3 to 0.3. In a preferred embodiment of the present invention, R 1 ~R 5 Each substituent is independently a substituent whose Hammett σp value is in the range of -0.2 to 0.2. In a preferred embodiment of the present invention, R 1 ~R 5 Each substituent is independently a substituent whose Hammett σp value is in the range of -0.1 to 0.1. In one aspect of the present invention, R 1 ~R 5 Each substituent is independently a substituent whose Hammett σp value is greater than 0 and within the range of 0.3 or less. In one aspect of the present invention, R 1 ~R 5 Each substituent is independently a substituent whose Hammett σp value is in the range of -0.3 or greater and less than 0. Here, "Hammett's σp value" was proposed by L.P. Hammett and quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following equation holds true between substituents and the reaction rate constant or equilibrium constant in para-substituted benzene derivatives: log(k / k0) = ρσp or log(K / K0) = ρσp This is a constant (σp) specific to the substituent in the formula. In the above formula, k0 is the rate constant of the unsubstituted benzene derivative, k is the rate constant of the substituted benzene derivative, K0 is the equilibrium constant of the unsubstituted benzene derivative, K is the equilibrium constant of the substituted benzene derivative, and ρ is the reaction constant determined by the type and conditions of the reaction. For an explanation of "Hammett's σp value" in this invention and the numerical values ​​of each substituent, refer to the description of σp value in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991). Groups with a negative Hammett's σp value tend to exhibit electron-donating properties, while groups with a positive Hammett's σp value tend to exhibit electron-withdrawing properties. In one aspect of the present invention, R 1 ~R 5Each of these substituents independently does not have a lone pair of electrons. In one aspect of the present invention, R 1 ~R 5 These substituents each independently lack π electrons.

[0011] In one aspect of the present invention, R 1 ~R 5 Each of these is independently selected from the group consisting of alkyl groups and aryl groups (e.g., groups with 6 to 30 carbon atoms), either as a single group or a combination of two or more such groups.

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

[0013] R 1 ~R 5 This is the other R 1 ~R 5 Alternatively, it does not bond with Ar to form a ring structure, but adjacent R 3 These elements may bond with each other to form a benzoflo or benzothieno skeleton. Therefore, the dibenzofuran (3-ring structure) on the left side of general formula (1) will not undergo further ring fusion to form a structure with 4 or more rings. Furthermore, the benzoflocarbazole (5-ring structure), benzothienocarbazole (5-ring structure), bisbenzoflocarbazole (7-ring structure), bisbenzothienocarbazole (7-ring structure), etc., on the right side of general formula (1) will not undergo further ring fusion. It is preferable that the structure on the right side of general formula (1) is a 5-ring structure. That is, in a preferred embodiment of the present invention, R 3 They do not combine with each other to form a ring structure.

[0014] In general formula (1), n1, n3, and n5 each independently represent an integer from 0 to 4, n2 represents an integer from 0 to 3, and n4 represents an integer from 0 to 2. In one aspect of the present invention, n1 to n5 are each independently integers from 0 to 2. In one aspect of the present invention, n1 is 0. In one aspect of the present invention, n2 is 0. In one aspect of the present invention, n3 is 0 or 1. In one aspect of the present invention, n4 is 0 or 1. In one aspect of the present invention, n5 is 0 or 1. In a preferred aspect of the present invention, n3 + n4 + n5 is 1 or greater. In a preferred aspect of the present invention, n3 + n4 + n5 is 1. In a preferred aspect of the present invention, n3 + n4 + n5 is 2. In a preferred aspect of the present invention, n1, n2, n4, and n5 are 0, and n3 is 1. In a preferred aspect of the present invention, n1 to n3 and n5 are 0, and n4 is 1. In one preferred embodiment of the present invention, n1 to n4 are 0 and n5 is 1. In one preferred embodiment of the present invention, n1, n2, and n4 are 0 and n3 and n5 are 1. In one 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 aspect of the present invention, X is a sulfur atom. In a preferred aspect 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 1-4 of the carbazole structure located to the right of Ar in general formula (1). Similarly, X may be bonded to any of positions 1-4 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 that make up the skeleton of the carbazole structure. Therefore, when the single bond is bonded at position 2, X is bonded at position 1 or 3. When the single bond is bonded at position 3, X is bonded at position 2 or 4. When the single bond is bonded at position 1, X is bonded at position 2. When the single bond is bonded at position 4, X is bonded at position 3. In general formula (1), X is written above the single bond, but general formula (1) also includes the structure of general formula (1') below, where the single bond is below X. [ka]

[0016] As the benzofurocarbazole-9-yl group bonded to the Ar in general formula (1), a substituted or unsubstituted benzofuro[2,3-a]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-a]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[2,3-b]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-b]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[2,3-c]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzofuro[3,2-c]carbazole-9-yl group can be used. As the benzothienocarbazole-9-yl group bonded to the Ar in general formula (1), a substituted or unsubstituted benzothieno[2,3-a]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzothieno[3,2-a]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzothieno[2,3-b]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzothieno[3,2-b]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzothieno[2,3-c]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted benzothieno[3,2-c]carbazole-9-yl group can be used. As the bisbenzoflocarbazole-9-yl group bonded to the Ar in general formula (1), a substituted or unsubstituted bisbenzoflo[2,3-a:2',3'-f]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzoflo[3,2-a:3',2'-f]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzoflo[2,3-b:2',3'-e]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzoflo[3,2-b:3',2'-e]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzoflo[2,3-c:2',3'-d]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzoflo[3,2-c:3',2'-d]carbazole-9-yl group can be used. As the bisbenzothienocarbazole-9-yl group bonded to the Ar in general formula (1), a substituted or unsubstituted bisbenzothieno[2,3-a:2',3'-f]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzothieno[3,2-a:3',2'-f]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzothieno[2,3-b:2',3'-e]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzothieno[3,2-b:3',2'-e]carbazole-9-yl group can be used. Alternatively, a substituted or unsubstituted bisbenzothieno[2,3-c:2',3'-d]carbazole-9-yl group can be used. Additionally, substituted or unsubstituted bisbenzothieno[3,2-c:3',2'-d]carbazole-9-yl groups can be used.

[0017] Specific examples of substituted or unsubstituted benzoflocarbazole-9-yl groups and substituted or unsubstituted benzothienocarbazole-9-yl groups bonded to Ar in general formula (1) are given below. However, the structures that can be adopted in the present invention are not limited to these specific examples. In this application, * indicates the bond position. Ph indicates an unsubstituted phenyl group. Also, in this application, the methyl group is not denoted as CH3, and the CH3 notation is omitted as shown in the lower left of D7. [ka] [ka] [ka]

[0018] Hereinafter, we exemplify the substitution of all hydrogen atoms in D1 to D64 with deuterium atoms, designating them as D1(D) to D64(D). Furthermore, hereinafter, we exemplify the substitution of only the hydrogen atoms bonded to the alkyl groups in D7 to D18 and D37 to D48 with deuterium atoms, designating them as D7(R) to D18(R) and D37(R) to D48(R). In addition, hereinafter, we exemplify the substitution of only the hydrogen atoms bonded to the phenyl groups in D19 to D30 and D49 to D60 with deuterium atoms, designating them as D19(Ph) to D30(Ph) and D49(Ph) to D60(Ph). In a preferred embodiment of the present invention, the substituted or unsubstituted benzoflocarbazole-9-yl group and the substituted or unsubstituted benzothienocarbazole-9-yl group bonded to Ar of 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), and more preferably from D1 to D30, D1(D) to D30(D), D7(R) to D18(R), and D19(Ph) to D30(Ph). In one preferred embodiment of the present invention, a selection is made 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 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. A monocyclic arylene group here means a non-fused phenylene group. A monocyclic heteroarylene group means an aromatic ring group with a non-fused single cyclic structure that includes a heteroatom as a constituent atom of the ring skeleton. The number of constituent atoms of the ring skeleton of a monocyclic heteroarylene group is preferably 5 to 7, more preferably 5 or 6, and for example, 6 can be used. Examples of heteroatoms constituting the ring skeleton of a monocyclic heteroarylene group include nitrogen atoms, oxygen atoms, and sulfur atoms, with nitrogen atoms being preferred. Examples of rings constituting a monocyclic heteroarylene group include pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, and triazine rings. When the carbazole, represented on the right side of general formula (1), is bonded to position 1 of the monoring constituting Ar, the dibenzofuran, represented on the left side of general formula (1), may be bonded to any position on the monoring constituting Ar. Preferably, the dibenzofuran is bonded to position 3 or 4 of the monoring constituting Ar. Particularly preferable is when the dibenzofuran is bonded to position 3 of the monoring constituting Ar (for example, when Ar is a substituted or unsubstituted 1,3-phenylene group), which is superior to when the dibenzofuran is bonded to position 2 or 4.

[0020] The monocyclic arylene groups and monocyclic heteroarylene groups that Ar can adopt may be substituted with a deuterium atom or a substituent that does not contain a cyano group, respectively. In one preferred embodiment of the present invention, substituents are selected in which the Hammett σp value is in the range of -0.3 to 0.3. For a description of substituents in the range of -0.3 to 0.3 Hammett σp value and preferred ranges, see R 1 ~R 5You can refer to the corresponding description. In one aspect of the present invention, a group without a lone pair of electrons is selected as the substituent. In one aspect of the present invention, a group without π electrons is selected as the substituent. In a preferred aspect of the present invention, one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., C1 to C40) and aryl groups (e.g., C6 to C30) is selected as the substituent. In a preferred aspect of the present invention, an alkyl group having C1 to C30 is selected as the substituent. For a description of alkyl groups and their preferred ranges, see R 1 ~R 5 You can refer to the corresponding explanation. In a preferred embodiment of the present invention, Ar is a phenylene group which may be substituted with 1 to 4 C1 to C20 alkyl groups, or a monocyclic heteroarylene group which may be substituted with 1 to 3 C1 to C20 alkyl groups. 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 given below, but the structures that can be adopted in the present invention are not limited by these examples. t-Bu represents a tert-butyl group, and Ph represents an unsubstituted phenyl group. [ka]

[0022] Hereinafter, Ar1(D) to Ar15(D) are shown as examples obtained by substituting all hydrogen atoms in Ar1 to Ar15 with deuterium atoms. Furthermore, hereinafter, Ar2(R) to Ar9(R) are shown as examples obtained by substituting only the hydrogen atoms bonded to the alkyl group of Ar2 to Ar9 with deuterium atoms. Furthermore, hereinafter, Ar10(Ph) is shown as an example obtained by substituting only the hydrogen atom bonded to the phenyl group of Ar10 with deuterium atoms. In one preferred embodiment of the present invention, the Ar in general formula (1) is selected from Ar1 to Ar9, Ar1(D) to Ar9(D), and Ar2(R) to Ar9(R), and more preferably from Ar1 to Ar9. In one preferred embodiment of the present invention, the Ar in general formula (1) is Ar1 or Ar1(D), and more preferably Ar1.

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

[0024] Specific examples of dibenzofuryl groups bonded to Ar in general formula (1) are given below, but the structures that can be adopted in the present invention are not limited to these specific examples. [ka]

[0025] Hereinafter, B1(D) to B12(D) are shown as examples obtained by substituting all hydrogen atoms in B1 to B12 with deuterium atoms. Furthermore, hereinafter, B2(R), B5(R), B8(R), and B11(R) are shown as examples obtained by substituting only the hydrogen atoms bonded to the alkyl groups of B2, B5, B8, and B11 with deuterium atoms. In addition, hereinafter, B3(Ph), B6(Ph), B9(Ph), and B12(Ph) are shown as examples obtained by substituting only the hydrogen atoms bonded to the phenyl groups of B3, B6, B9, and B12 with deuterium atoms. In a preferred embodiment of the present invention, the dibenzofuryl group bonded to the Ar of general formula (1) is selected from B1 to B3, B1(D) to B3(D), B2(R), and B3(Ph), and more preferably from B1 to B3. In one aspect of the present invention, the dibenzofuryl group bonded to the Ar of general formula (1) is selected from B1, B4, B7, B10, B1(D), B4(D), B7(D), and B10(D), more preferably from B1, B4, B7, and B10.

[0026] In this application, the "alkyl group" may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched portions may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group. In one aspect of the present invention, the number of carbon atoms in the alkyl group is 1 to 4. In one aspect of the present invention, the alkyl group is a methyl group. In one aspect of the present invention, the alkyl group is an isopropyl group. In one aspect of the present invention, the alkyl group is a tert-butyl group. When multiple alkyl groups exist in a molecule represented by general formula (1), these alkyl groups may be identical or different. In one aspect of the present invention, all alkyl groups in a molecule represented by general formula (1) are identical. 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 as used herein includes the number of alkyl groups substituted with phenyl groups. In this application, "a phenyl group which may be substituted with an alkyl group" means that at least one of the five hydrogen atoms present in the phenyl group may be substituted with an alkyl group. In one aspect 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 aspect of the present invention, the phenyl group is not substituted with an alkyl group. The number of carbon atoms in the alkyl group substituted on the phenyl group is preferably 1 to 6, and more preferably 1 to 4. Examples include 4-methylphenyl group, 3-methylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2,3,4,5,6-heptamethylphenyl group, 4-isopropylphenyl group, 3-isopropylphenyl group, 3,5-diisopropylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, and 3,5-ditert-butylphenyl group. Furthermore, groups in which all hydrogen atoms present in the alkyl substituents among these specific examples are substituted with deuterium atoms can also be exemplified. In this application, "a deuterated alkyl group" means that at least one of the hydrogen atoms of the alkyl group may be substituted with a deuterium atom. All of the hydrogen atoms of the alkyl group may be substituted with deuterium atoms. For example, deuterated methyl groups include CH3, CDH2, CD2H, and CD3. Preferably, the "a deuterated alkyl group" is either a completely undeuterated alkyl group or an alkyl group in which all hydrogen atoms are substituted with deuterium atoms. In one aspect of the present invention, a completely undeuterated alkyl group is selected as the "a deuterated alkyl group". In one aspect of the present invention, an alkyl group in which all hydrogen atoms are substituted with deuterium atoms is selected as the "a deuterated alkyl group".

[0027] The general formula (1) does not contain a cyano group. In a preferred embodiment of the present invention, the 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, the general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. The molecular weight of the compound represented by the general formula (1) is 499 or more, preferably 700 or less, more preferably 600 or less, and may be, for example, 550 or less, or 530 or less.

[0028] As a compound represented by general formula (1), the compound represented by the following general formula (2A) can be preferably exemplified. [ka]

[0029] As a compound represented by general formula (1), the compound represented by the following general formula (2B) can be preferably exemplified. [ka]

[0030] R in general formula (2A) and general formula (2B) 1 ~R 5 For the definitions and explanations of n1 to n5 and X, refer to the corresponding definitions and explanations in general formula (1). R in general formula (2A) and general formula (2B) 6 For the definition and explanation of R in general formula (1), see 1 ~R 5 You can refer to the definition and explanation. In general formulas (2A) and (2B), n6 is an integer between 0 and 3. n6 can be selected within the range of 0 to 2, or it can be 0 or 1, and it is also preferable that it be 0. In general formulas (2A) and (2B), n1 to n6 can each be independently selected within the range of 0 to 2, or it can be 0 or 1. Also, n1 to n6 may all be 0. Of the structures represented by general formula (2A) and general formula (2B), the most preferred is the one in general formula (2A) and general formula (2B) where (R 6 ) n6 This structure has a phenylene group to which it is bonded that is a 1,3-phenylene group (metaphenylene group).

[0031] As a compound represented by general formula (1), the compound represented by general formula (3) below can be particularly preferred as an example. [ka]

[0032] In general formula (3), R 1 ~R 6 Each of these independently represents a substituent that does not contain a deuterium atom or a cyano group. 1 ~R 6 This is the other R 1 ~R 6 Although it does not bond with adjacent R to form a ring structure, 3 These elements may combine with each other to form a benzoflo or benzothieno skeleton. n1, n3, and n5 each independently represent an integer from 0 to 4, n2 and n6 each independently represent an integer from 0 to 3, and n4 represents an integer from 0 to 2. However, n1 + n3 + n4 + n5 is greater than or equal to 1. R 1 and R 3 ~R 5 One or two of these 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. R in general formula (3) 1 ~R 6 For the definitions and explanations of n1 to n6, see R in general formulas (2A) and (2B). 1 ~R 6 You can refer to the definitions and explanations of n1~n6, but in general formula (3), n1+n3+n4+n5 is 1 or greater, R 1 and R 3 ~R 5The only difference is that one or two of them represent 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"). In general formula (3), R 1 and R 3 ~R 5 No more than three of them are phenyl groups A. In one aspect of the present invention, one R 1 Only one is a phenyl group A. In one aspect of the present invention, one R 3 Only one is a phenyl group A. In one aspect of the present invention, one R 4 Only one is a phenyl group A. In one aspect of the present invention, one R 5 Only one is a phenyl group A. In one aspect of the present invention, one R 3 and one R 4 Only one is a phenyl group A. In one aspect of the present invention, one R 3 and one R 5 Only one is a phenyl group A. In one aspect of the present invention, one R 4 and one R 5 Only this is a phenyl group A. In this invention, two R 3 Only two R 4 just or two R 5 Only phenyl group A may be present. Note that when n3+n4+n5 is 0, R 1 It is preferable that the group is not an unsubstituted phenyl group. In one aspect of the present invention, R 3 ~R 5 At least one of them is a phenyl group A, and there is at least one n3+n4+n5. 3 ~R 5 At least one of the phenyl groups A is bonded to the meta position (position 2 of the carbazole ring) relative to the bond position of the nitrogen atom constituting the carbazole ring skeleton. In a preferred embodiment of the present invention, R 3 ~R 5 At least one of the phenyl groups A is bonded at the para position (position 3 of the carbazole ring) relative to the bond position of the nitrogen atom constituting the carbazole ring skeleton. In one embodiment of the present invention, R 3 ~R 5The phenyl group A is bonded only at the meta position (position 2 of the carbazole ring) relative to the nitrogen atoms constituting the carbazole ring skeleton. In a preferred embodiment of the present invention, R 3 ~R 5 The phenyl group A is bonded only at the para position (position 3 of the carbazole ring) relative to the nitrogen atoms constituting the carbazole ring skeleton. In one embodiment of the present invention, R 3 ~R 5 The phenyl group A is bonded only at the para position relative to the oxygen atom constituting the benzoflo ring skeleton or the sulfur atom constituting the benzothieno ring skeleton. In a preferred embodiment of the present invention, R 3 ~R 5 The phenyl group A is bonded in two positions: one at the para position relative to the nitrogen atom that makes up the carbazole ring skeleton, and another at the para position relative to the oxygen atom that makes up the benzoflo ring skeleton or the sulfur atom that makes up the benzothieno ring skeleton. In one aspect of the present invention, phenyl group A is a phenyl group which may be deuterated or substituted with an alkyl group. In a preferred aspect of the present invention, phenyl group A is a phenyl group which may be substituted with a deuterium atom. In a particularly preferred aspect of the present invention, phenyl group A is an unsubstituted phenyl group. In general formula (3), n3+n4+n5 is an integer from 1 to 10, preferably an integer from 1 to 8, more preferably an integer from 1 to 6, and even more preferably an integer from 1 to 4. In one preferred embodiment of the present invention, n3+n4+n5 is 1. In one 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 the organic layer containing the compound represented by general formula (1) is intended to be used by forming a film by vapor deposition. 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). Compounds represented by general formula (1) may be deposited as films by coating methods regardless of their molecular weight. Coating methods allow for the deposition of even relatively large molecular weight compounds. Compounds represented by general formula (1) have the advantage of being readily soluble in organic solvents. Therefore, coating methods are easily applied to compounds represented by general formula (1), and their purity can be easily increased through purification.

[0034] It is preferable that the compound represented by general formula (1) does not contain metal atoms or boron atoms. For example, as the compound represented by general formula (1), 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. For example, as the compound represented by general formula (1), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as the compound represented by general formula (1), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms can be selected.

[0035] The following are specific examples of compounds represented by general formula (1), but the compounds that can be used in the present invention are not limited to these examples. Note that D in P6 to P14 represents a deuterium atom. [ka] [ka] [ka] [ka]

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

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

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

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

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

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

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

[0043] [ka]

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

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

[0046] In this specification, compounds represented by the following general formula (A) are also disclosed as compounds useful as electron barrier materials and host materials. [ka]

[0047] In general formula (A), X 1 X represents an oxygen atom or a sulfur atom. 2 It consists of an oxygen atom, a sulfur atom, and N(R) 7 ) or C(R 8 )(R 9 ) represents R 1 ~R 6 Each of these independently represents one atom or group, or a combination of two or more, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. At least one R 1 R is an aryl group which may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. 1 ~R 6 This is the other R 1 ~R 6 Although it does not bond with adjacent R to form a ring structure, 3 These elements may combine with each other to form a benzoflo or benzothieno skeleton. n1 represents an integer from 1 to 4, n3, n5, and n6 each independently represent an integer from 0 to 4, n2 represents an integer from 0 to 3, and n4 represents an integer from 0 to 2. Note that in general formula (A), (R 5 ) n5 The benzene ring to which it is bonded and (R 4 ) n4 The benzene ring to which it is bonded consists of a single bond and X 2 Although they are connected by two bonds of a linking group via X, the left-right positional relationship of these two bonds can be reversed. That is, in the general formula (A) above, the single bond is on the left, X 2The linking group via is shown on the right, but the single bond is on the right, X 2 Structures in which the linking group via is on the left side are also included in general formula (A).

[0048] In one preferred embodiment of the present invention, X 1 and X 2 They are identical. In one aspect of the present invention, X 1 and X 2 They are different. In one preferred embodiment of the present invention, X 1 and X 2 Both are oxygen atoms. In one aspect of the present invention, X 1 and X 2 Both are sulfur atoms. In one aspect of the present invention, X 1 is an oxygen atom, X 2 X is a sulfur atom. In one aspect of the present invention, X 1 This is a sulfur atom, X 2 X is an oxygen atom. In one aspect of the present invention, X 1 is an oxygen atom, X 2 N(R 7 ) In one aspect of the present invention, X 1 is an oxygen atom, X 2 is C(R 8 )(R 9 ) In one 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 Each is independently selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group consisting of two or more atoms or groups, preferably a deuterium atom, an alkyl group which may be substituted with a deuterium atom, or an aryl group which may be substituted with one or more atoms or groups which may be substituted with a group consisting of a deuterium atom, an alkyl group, and an aryl group. In a preferred embodiment of the present invention, R 1 ~R 6Each of these is an aryl group which may be independently a deuterium atom or an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom and an aryl group, or a combination of two or more groups. The number of carbon atoms in the alkyl group in the description of general formula (1) can usually be selected in the range of 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 usually be selected in the range of 6 to 30, preferably 6 to 18, more preferably 6 to 14, for example 6 to 10. In one aspect of the present invention, R 3 They bond with each other to form a benzophloen skeleton. In one aspect of the present invention, R 3 These elements bond to each other to form a benzothieno skeleton. The benzoflo skeleton and the benzothieno skeleton may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. In one aspect of the present invention, R 3 They do not combine with each other to form a ring structure.

[0050] at least one R 1 R is an aryl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of deuterium atoms, alkyl groups and aryl groups, more preferably a phenyl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of deuterium atoms, alkyl groups and aryl groups, and even more preferably a phenyl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of deuterium atoms and phenyl groups. In one aspect 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, preferably an unsubstituted phenyl group or a phenyl group in which all hydrogen atoms are substituted with deuterium atoms. In a preferred embodiment of the present invention, one R 1 Only the aryl group may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. In one aspect of the present invention, two R 1However, the aryl group may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. 1 Specific examples of the groups that can be adopted are P1 to P14 above. However, the R that can be adopted in the present invention is 1 This should not be interpreted restrictively by these specific examples. In general formula (A), (R 5 ) n5 When the group bonded to the benzene ring to which is bonded from the right side [the pentacyclic group on the right side of general formula (A)] is a benzoflo[3,2-a]carbazolyl group, R 1 It is never an unsubstituted phenyl group.

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

[0052] In general formula (A1), X 1 , X 2 , R 1 ~R 6 For the definitions and explanations of n1 to n6, please refer to the corresponding descriptions in the general formula (A) above.

[0053] [Organic semiconductor element] Compounds represented by general formula (1) can be preferably applied to organic semiconductor devices. For example, CMOS (complementary metal-oxide-semiconductor) devices can be fabricated using compounds represented by general formula (1). In some embodiments of this disclosure, organic optical devices such as organic electroluminescent devices and solid-state image sensors (e.g., CMOS image sensors) can be fabricated using compounds represented by general formula (1). In particular, the compound represented by general formula (1) of the present invention can be used in organic light-emitting devices such as organic electroluminescent devices (organic EL devices). In particular, the compound represented by general formula (1) of the present invention can be effectively used as an electron barrier material for organic light-emitting devices. In particular, by using the compound represented by general formula (1) of the present invention in the electron barrier layer, the device lifespan can be extended.

[0054] An organic electroluminescent element has a structure in which at least an anode, a cathode, and an organic layer formed between the anode and the cathode. The organic layer includes at least a light-emitting layer, and preferably has one or more organic layers (particularly an electron barrier layer) in addition to the light-emitting layer. Examples of organic layers constituting an organic electroluminescent element include a hole transport layer, a hole injection layer, an electron barrier layer, an electron injection layer, an electron transport layer, an exciton barrier layer, and a base layer for the light-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. The following describes each component and layer of an organic electroluminescent element. Note that the descriptions of the substrate and light-emitting layer also apply to the substrate and light-emitting layer of an organic photoluminescent element.

[0055] (Electron barrier layer) In a preferred embodiment of the present invention, the compound represented by general formula (1) is used in the electron barrier layer of an organic electroluminescent device. The electron barrier layer may contain only the compound represented by general formula (1), or it 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 barrier layer is preferably 50% by weight or more, more preferably 90% by weight or more, for example, 99% by weight or more, or 99.9% by weight or more. The thickness of the electron barrier layer is preferably 1 nm or more, more preferably 3 nm or more, for example, 5 nm or more, or for example, 10 nm or more. The thickness of the electron barrier layer is preferably less than 30 nm, more preferably less than 20 nm, for example, 15 nm or less. The thickness of the electron barrier layer is preferably less than the thickness of the light-emitting layer. The thickness of the electron barrier layer is preferably half or less of the thickness of the light-emitting layer, more preferably one-third or less, for example, one-quarter or less. Furthermore, it is preferable that the ratio be 1 / 20 or more, and for example, it can be 1 / 10 or more, or for example, 1 / 6 or more. The electron barrier layer containing the compound represented by general formula (1) is preferably provided between the light-emitting layer and the anode. In one aspect of the present invention, the light-emitting layer and the electron barrier layer are laminated in direct contact. One aspect of the present invention includes a laminated structure in which an electron barrier layer containing a compound represented by general formula (1), a base layer, and an emissive layer are stacked in that order from the anode side. The electron barrier layer and the base layer are stacked in direct contact, and the base layer and the emissive layer are stacked in direct contact, but the electron barrier layer and the emissive layer are not in contact.

[0056] (base layer) The base layer is formed for purposes such as improving the orientation of the light-emitting layer, and is a layer containing a hole-transporting material. In one aspect of the present invention, the base layer contains a compound having a common substructure with the compound contained in the light-emitting layer. Here, a common substructure means that the substructure consists of 12 or more atoms other than hydrogen atoms and deuterium atoms, preferably consisting of 16 or more atoms other than hydrogen atoms and deuterium atoms, and may also consist of, for example, 20 or more atoms other than hydrogen atoms and deuterium atoms. In one aspect of the present invention, the base layer contains the same compound as the compound contained in the light-emitting layer. In one aspect of the present invention, the base layer contains only the same compound as the compound contained in the light-emitting layer. In one aspect of the present invention, the base layer contains the same compound as the host material contained in the light-emitting layer. The thickness of the base layer 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 base layer is preferably less than the thickness of the light-emitting layer. The thickness of the base layer is preferably half or less of the thickness of the light-emitting layer, more preferably one-third or less, and can be, for example, one-quarter or less. It is also preferably one-twentieth or more, and can be, for example, one-tenth or more. The thickness of the base layer is preferably less than the thickness of the electron barrier layer. The thickness of the base layer can be, for example, three-quarters or less, for example two-thirds or less, or for example one-half or less of the thickness of the electron barrier layer. It is also preferably one-twentieth or more, and can be, for example one-tenth or more, or for example one-quarter or more.

[0057] (Emitting layer) The light-emitting layer is a layer that emits light after excitons are generated by the recombination of holes and electrons injected from the anode and cathode, respectively. The light-emitting layer includes at least a light-emitting material. For an organic electroluminescent element to exhibit high luminescence efficiency, it is important to confine the singlet and triplet excitons of the luminescent material within the luminescent material itself. Therefore, it is preferable to use a host material in addition to the luminescent material in the luminescent layer. As the host material, an organic compound having a singlet excitation energy higher than that of the luminescent material of the present invention can be used, and it is preferable to use an organic compound having both singlet and triplet excitation energies higher than those of the luminescent material. By using a host material, it becomes possible to confine the singlet and triplet excitons generated in the luminescent material within the molecules of the luminescent material, thereby fully maximizing its luminescence efficiency. However, even if the singlet and triplet excitons cannot be sufficiently confined, it may still be possible to obtain high luminescence efficiency, so any host material capable of achieving high luminescence efficiency can be used in the present invention without particular restrictions. In the organic electroluminescent element of the present invention, the maximum amount of light emitted from the element comes from the luminescent material contained in the luminescent layer. This light emission includes fluorescence emission and may also include delayed fluorescence. However, some or partial emission from the host material is acceptable. When a host material is used, the concentration of the light-emitting material in the light-emitting layer is preferably 0.1% by weight or more, more preferably 1% by weight or more, preferably 50% by weight or less, more preferably 20% by weight or less, and even more preferably 10% by weight or less.

[0058] An assist dopant may be used in the emissive layer. In this case, the emissive layer is composed of a host material, an assist dopant, and an emissive material. Here, the host material is one with a lower minimum excited singlet energy level than the assist dopant, and the emissive material is one with a lower minimum excited singlet energy level than the assist dopant. In the present invention, it is particularly preferable to use a delayed fluorescence material as the assist dopant. Delayed fluorescence is the fluorescence emitted when a compound in an excited state returns from the excited singlet state to the ground state after a reverse intersystem crossover occurs from the excited triplet state to the excited singlet state. It is fluorescence that is observed later than fluorescence from the excited singlet state that transitions directly from the ground state (immediate fluorescence). In the present invention, when the transient decay curve of emission is measured at 300K for a thin film containing the target compound, if a luminescence component with a long emission lifetime (delayed fluorescence) is observed in addition to a luminescence component with a short emission lifetime (immediate fluorescence), the target compound is designated as a delayed fluorescence material. The delayed fluorescence material is preferably a thermally activated delayed fluorescence material capable of inverse intersystem crossing through the absorption of thermal energy. The thermal activation of the delayed fluorescence material can be confirmed by measuring the transient decay curve of the emission, which shows that the emission lifetime increases with increasing temperature. By using the delayed fluorescence material as an assist dopant, the energy of the excited singlet state generated by a direct transition from the ground state in the assist dopant, as well as the excited singlet energy due to inverse intersystem crossing, are efficiently transferred to the luminescent material, effectively assisting the emission of light from the luminescent material. When a light-emitting layer is composed of a host material, an assist dopant, and a light-emitting material, it is preferable that the concentration of the assist dopant in the light-emitting layer is lower than the content of the host material. Specifically, when the total weight of the host material, the assist dopant, and the light-emitting material is taken as 100% by weight, it is preferable that the host material content be between 15% and 99.9% by weight, the assist dopant content be between 5.0% and 50% by weight, and the light-emitting material content be between 0.5% and 5.0% by weight. In one aspect of the present invention, the light-emitting layer does not contain inorganic compounds. Also in one aspect of the present invention, the light-emitting layer does not contain metal atoms. In one aspect of the present invention, phosphorescence is not 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 transport ability, electron transport ability, prevents the emission from becoming longer wavelengths, and has a high glass transition temperature. In one aspect of the present invention, a compound containing a carbazole structure can be preferably selected as the host material. In one preferred aspect of the present invention, the host material may contain 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 having three structures can be selected. In one preferred aspect of the present invention, a compound containing a 1,3-phenylene structure can be selected as the host material. In one preferred aspect of the present invention, a compound containing a biphenylene structure can be selected as the host material. In one preferred aspect of the present invention, a compound containing 5 to 8 benzene rings in its molecule can be selected as the host material, for example, a compound with 5 rings, a compound with 6 rings, or a compound with 7 rings can be selected. The following are some preferred compounds that can be used as host materials, but the host materials that can be used in the present invention are not limited to the following specific examples. [ka] [ka] [ka] [ka]

[0060] The light-emitting layer can use a delayed fluorescence material as either the light-emitting material or an assist dopant. Furthermore, different delayed fluorescence materials can be used as the light-emitting material and the assist dopant. When the emission lifetime is measured from the delayed fluorescence material using a fluorescence lifetime measurement system (such as the Hamamatsu Photonics Streak Camera System), fluorescence with an emission lifetime of 100 ns (nanoseconds) or more is typically observed. The delayed fluorescence material has a difference of ΔE between its lowest excitation singlet energy and its lowest excitation triplet energy at 77K. ST It is preferable that the voltage is 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. ΔE ST If the thermal energy absorption is small, the reverse intersystem crossover from the excited singlet state to the excited triplet state is more likely to occur, thus functioning as a thermally activated delayed fluorescence material. Thermally activated delayed fluorescence materials absorb the heat emitted by the device and relatively easily reverse intersystem crossover from the excited triplet state to the excited singlet state, and can efficiently contribute that excited triplet energy to luminescence.

[0061] In the present invention, the lowest excitation singlet energy (E) of the compound S1 ) and the lowest excited triplet energy (E T1 ) is the value obtained by the following procedure: ΔE ST is E S1 -E T1 This value was obtained by calculation. (1) Lowest excitation singlet energy (E S1 ) A thin film or toluene solution of the compound to be measured (concentration 10%) -5Prepare a sample (mol / L). Measure the fluorescence spectrum of this sample at room temperature (300K). The fluorescence spectrum has emission on the vertical axis and wavelength on the horizontal axis. Draw a tangent to the rising edge of the short-wave side of the emission spectrum, and determine the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis. Convert this wavelength value to an energy value using the following conversion formula: E S1 Let's assume that. Conversion formula: E S1 [eV]=1239.85 / λedge In the examples described below, the emission spectra were measured using an LED light source (Thorlabs, M300L4) as the excitation light source and a detector (Hamamatsu Photonics, PMA-12 multi-channel spectrometer C10027-01). (2) Lowest excited triplet energy (E T1 ) Lowest excitation singlet energy (E S1 The same sample used in the measurement is cooled to 77[K] with liquid nitrogen, and excitation light (300 nm) is irradiated onto the phosphorescence measurement sample. Phosphorescence is measured using a detector. The emission from 100 milliseconds after excitation light irradiation is taken as the phosphorescence spectrum. A tangent line is drawn to the rising edge of 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 E T1 Let's assume that. Conversion formula: E T1 [eV]=1239.85 / λedge The tangent to the rise 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 wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 10% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side.

[0062] It is preferable that the delayed fluorescence 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 fluorescence material. For example, a compound consisting of carbon atoms, hydrogen atoms, and nitrogen atoms may be selected as the delayed fluorescence material. Typical delayed fluorescence materials include compounds having a structure in which one or two acceptor groups and at least one donor group are bonded to a benzene ring. Preferred examples of acceptor groups include cyano groups and groups containing heteroaryl rings that include nitrogen atoms as constituent atoms of the ring skeleton, such as triazinyl rings. Preferred examples of donor groups include, for example, substituted or unsubstituted carbazole-9-yl groups. For example, examples include compounds in which three or more substituted or unsubstituted carbazole-9-yl groups are bonded to the benzene ring, and compounds in which five-membered ring portions of substituted or unsubstituted benzofuran rings, substituted or unsubstituted benzothiophene rings, substituted or unsubstituted indole rings, substituted or unsubstituted indene rings, or substituted or unsubstituted silaidene rings are fused to at least one of the two benzene rings constituting the carbazole-9-yl group.

[0063] In one preferred embodiment of the present invention, a compound represented by the following general formula (4) is used as the delayed fluorescence material. [ka] In 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 R25 At least one of them represents a group represented by the following general formula (6), R 21 ~R 25 The remainder represents a hydrogen atom or a substituent (however, the substituent referred to here is not a cyano group, a group represented by general formula (5) below, or a group represented by general formula (6) below). [ka] In general formula (5), L 1 represents a single bond or a divalent linking group, R 31 and R 32 Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position. [ka] In general formula (6), L 2 represents a single bond or a divalent linking group, R 33 and R 34 Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position.

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

[0065] In one preferred embodiment of the present invention, L in general formula (5) 1 It is a single bond. In one aspect of the present invention, L 1The linking group is a divalent 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 a substituent such as an alkyl group having 1 to 3 carbon atoms). In one aspect of the present invention, R in general formula (5) 31 and R 32 Each of these is independently one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 ring skeleton constituent atoms), alkenyl groups (e.g., 1 to 40 carbon atoms), and alkynyl groups (e.g., 1 to 40 carbon atoms) (hereinafter these groups are referred to as "substituent group A groups"). In a preferred embodiment of the present invention, R 31 and R 32 Each of these is independently a substituted or unsubstituted aryl group (e.g., having 6 to 30 carbon atoms), and examples of substituents on the aryl group include the groups of substituent group A. In a preferred embodiment of the present invention, R 31 and R 32 They are identical.

[0066] In one preferred embodiment of the present invention, L in general formula (6) 2 It is a single bond. In one aspect of the present invention, L 2 The linking group is a divalent 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 a substituent such as an alkyl group having 1 to 3 carbon atoms). In one aspect of the present invention, R in general formula (6) 33 and R 34Each of these independently represents a substituted or unsubstituted alkyl group (e.g., 1-40 carbon atoms), a substituted or unsubstituted alkenyl group (e.g., 1-40 carbon atoms), a substituted or unsubstituted aryl group (e.g., 6-30 carbon atoms), or a substituted or unsubstituted heteroaryl group (e.g., 5-30 carbon atoms). Substituents for alkyl groups, alkenyl groups, aryl groups, and heteroaryl groups as used here include hydroxyl groups, halogen atoms (e.g., fluorine, chlorine, bromine, iodine atoms), alkyl groups (e.g., 1-40 carbon atoms), alkoxy groups (e.g., 1-40 carbon atoms), alkylthio groups (e.g., 1-40 carbon atoms), aryl groups (e.g., 6-30 carbon atoms), aryloxy groups (e.g., 6-30 carbon atoms), arylthio groups (e.g., 6-30 carbon atoms), heteroaryl groups (e.g., 5-30 carbon atoms in the ring skeleton), heteroaryloxy groups (e.g., 5-30 carbon atoms in the ring skeleton), and heteroarylthio groups. Examples of groups include one or more groups selected from the group consisting of oxy groups (e.g., 5-30 atoms in the ring skeleton), acyl groups (e.g., 1-40 carbon atoms), alkenyl groups (e.g., 1-40 carbon atoms), alkynyl groups (e.g., 1-40 carbon atoms), alkoxycarbonyl groups (e.g., 1-40 carbon atoms), aryloxycarbonyl groups (e.g., 1-40 carbon atoms), heteroaryloxycarbonyl groups (e.g., 1-40 carbon atoms), silyl groups (e.g., trialkylsilyl groups with 1-40 carbon atoms), nitro groups, and cyano groups (hereinafter, these groups will be referred to as "substituent group B groups"). R 33 and R 34 These may be linked to each other by single bonds or linking groups to form a cyclic structure. In particular, R 33 and R 34 If the group is an aryl group, it is preferable that they are bonded to each other via single bonds or linking groups to form a cyclic structure. The linking groups referred to here are -O-, -S-, and -N(R 35 )-,-C(R 36 )(R 37 We can list -, -C(=O)-, -O-, -S-, -N(R 35 )-,-C(R 36 )(R 37 )- is preferred, -O-, -S-, -N(R 35)- is more preferable. R 35 ~R 37 Each of these independently represents a hydrogen atom or a substituent. The substituent can be selected from substituent group A above or from substituent group B below, and preferably is 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 the group represented by general formula (7) below. [ka]

[0068] L of general formula (7) 11 L represents a single bond or a divalent linking group. 11 For an explanation and preferred range, see L above. 2 You can refer to the explanation and preferred range. R in general formula (7) 41 ~R 48 Each of these 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 48These rings may bond to each other to form a cyclic structure. The cyclic structure formed by the bonding may be an aromatic ring or an antilipid ring, and may contain heteroatoms. Furthermore, the cyclic structure may be a fused ring of two or more rings. The heteroatoms referred to here are preferably selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. Examples of the cyclic structures formed include benzene rings, naphthalene rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, pyrrole rings, imidazole rings, pyrazole rings, imidazoline rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, cyclohexadiene rings, cyclohexene rings, cyclopentaene rings, cycloheptatriene rings, cycloheptadiene rings, cycloheptaene rings, furan rings, thiophene rings, naphthyridine rings, quinoxaline rings, and quinoline rings. For example, a ring formed by the fusion of multiple rings, such as a phenanthrene ring or a triphenylene ring, may also be formed. The number of rings included in the group represented by general formula (7) may be selected from the range of 3 to 5, or from the range of 5 to 7. R 41 ~R 48 Examples of substituents that can be adopted include the groups of substituent group B above, preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms that 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 R 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 R is a hydrogen atom or an unsubstituted aryl group having 6 to 10 carbon atoms. In a preferred embodiment of the present invention, R 41 ~R 48 It is all hydrogen atoms. In general formula (7), * represents the bond position.

[0069] In one preferred embodiment of the present invention, an azabenzene derivative is used as a delayed fluorescence material. In one 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 one 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, a pyrimidine structure, or a pyrazine structure can be cited, 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 one preferred embodiment of the present invention, a compound represented by the following general formula (8) is used as the delayed fluorescence material. [ka] In general formula (8), Y 1 , Y 2 and Y 3 Y represents at least one nitrogen atom and the rest methine groups. In one aspect of the present invention, Y 1 This is a nitrogen atom, Y 2 and Y 3 This is a methine group. Preferably Y 1 and Y 2 This is a nitrogen atom, Y 3 This is a methine group. More preferably, Y 1 ~Y 3 All of them are nitrogen atoms. In general formula (8), Z 1 ~Z 3 Each of these independently represents a hydrogen atom or substituent, but at least one is a donor substituent. A donor substituent means a group with a negative Hammett σp value. Preferably, Z 1 ~Z 3At least one of the groups is a group comprising a diarylamino structure (the two aryl groups bonded to the 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). In one aspect of the present invention, Z 1 ~Z 3 Only one of them is a group represented by general formula (6) or (7). In one aspect of the present invention, Z 1 ~Z 3 Only these two are groups that can be independently represented by general formula (6) or (7). In one aspect of the present invention, Z 1 ~Z 3 All of these are groups that can be independently represented by general formula (6) or (7). For details and preferred ranges of general formula (6) and general formula (7), refer to the corresponding descriptions above. The remaining Z are groups that are not represented by general formula (6) and general formula (7). 1 ~Z 3 The substituent is preferably a substituted or unsubstituted aryl group (for example, having 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms), and examples of substituents on the aryl group include one group or a combination of two or more groups selected from the group consisting of aryl groups (for example, having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms) and alkyl groups (for example, having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms). In one embodiment of the present invention, general formula (8) does not contain a cyano group.

[0071] In one preferred embodiment of the present invention, a compound represented by the following general formula (9) is used as the delayed fluorescence material. [ka] In general formula (9), Ar 1 This is A below 1 and D 1 It forms a cyclic structure which may be substituted with and represents a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring. 2 Ar 3Each of these may form a cyclic structure, and if 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 from 0 to 2, and m2 represents an integer from 0 to 1. A 1 D represents a cyano group, phenyl group, pyrimidyl group, triazyl group, or benzonitrile group. 1 D represents a substituted or unsubstituted 5H-indoro[3,2,1-de]phenazine-5-yl group, or a substituted or unsubstituted heterocyclic condensed carbazolyl group that does not contain a naphthalene structure, and multiple D in general formula (9) 1 If they exist, they may be the same or different. Also, D 1 The substituents may be bonded to each other to form a cyclic structure.

[0072] Further preferred delayed fluorescence materials include compounds represented by the following general formula (E1). [ka]

[0073] In general formula (E1), R 1 , R 3 ~R 16 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 2 R represents an acceptor group. 1 and R 2 Either they are bonded to each other to form an acceptor group, or R 2 and R 3 These groups 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 R12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 They may be joined to each other to form a ring 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 atoms is O or NR, and the other may be O or NR or not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. CR in general formula (1) 1 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 It may be replaced with N.

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

[0075] In general formula (E2), R 1 and R 2 Each of these 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 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 3 , R3 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 , R 16 and R 1 These may be bonded to each other to form a ring structure. CR in general formula (1) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 This can be replaced with N.

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

[0077] In general formula (E3), Z 1 and Z 2Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R 1 ~R 9 Each of these 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 They may be bonded to each other to form a ring structure. However, Z 1 , Z 2 , R 1 and R 2 A ring formed by the bonding of these elements, R 2 and R 3 A ring formed by the bonding of these elements, R 4 and R 5 A ring formed by the bonding of these elements, and R 5 and R 6 At least one of the rings formed by the bonding of these elements is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole, and R 1 ~R 9 At least one of them is a substituted or unsubstituted aryl group, or an acceptor group, or Z 1 and Z 2 At least one of the rings has an aryl group or an acceptor group as a substituent. Substitutable carbon atoms among the benzene ring skeleton constituent carbon atoms of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with nitrogen atoms. CR in general formula (1) 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR9 It may be replaced with N.

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

[0079] In general formula (E4), Z 1 This represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z 2 and Z 3 Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring, R 1 R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3 Each of these 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 They may be bonded to each other to form a ring structure. However, R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these elements are joined together to form a ring structure.

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

[0081] In general formula (E5), R 1and R 2 Each of these 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 of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R 3 ~R 9 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. However, R 1 , R 2 , Z 1 and Z 2 At least one of these includes 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 1 These may be bonded to each other to form a cyclic structure. Substitutable carbon atoms among the benzene ring skeleton constituent carbon atoms of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with nitrogen atoms. CR in general formula (1) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 It may be replaced with N.

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

[0083] In general formula (E6), R 201 ~R 221 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, preferably 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 these is bonded to each other to form a benzophlo or benzothieno structure. Preferably, R 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 One or two of the following pairs, and 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 R221 One or two of these groups are bonded together to form a benzofloe or benzothieno structure. More preferably, R 203 and R 204 These combine with each other to form a benzofloxic structure or a benzothieno structure, and more preferably R 203 and R 204 , R 216 and R 217 These are bonded to each other to form a benzofloxacin or benzothieno structure. Particularly preferred is R 203 and R 204 , R 216 and R 217 These are bonded to each other to form a benzofloxacin or benzothieno structure, 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). The general formula (E6) includes R 201 ~R 208 , R 214 ~R 221 Each of these may be an independent deuterium atom, but a hydrogen atom ( 1 It includes structures that are not H). That is, R 201 ~R 208 , R 214 ~R 221 If the structure includes an atom with one proton, that atom must be a deuterium atom.

[0084] Furthermore, compounds represented by general formula (1) as described in the specifications of Japanese Patent Applications Nos. 2021-103698, 2021-103699, 2021-103700, 2021-081332, 2021-103701, 2021-151805, and 2021-188860 can be used as delayed fluorescence materials. A description of these general formulas (1) and specific compounds are incorporated herein by reference as part of this specification.

[0085] The following are preferred compounds that can be used as delayed fluorescence materials. In the structural formulas of the following example compounds, t-Bu represents a tert-butyl group. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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

[0087] In addition to the above, other known delayed fluorescence materials can be used in appropriate combinations. Furthermore, even unknown delayed fluorescence materials can be used. As delayed fluorescence materials, paragraphs 0008-0048 and 0095-0133 of Publication No. WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of Publication No. WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of Publication No. WO2013 / 011955, and paragraphs 0008-007 of Publication No. WO2013 / 081088 Paragraphs 1 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of Japanese Patent Publication No. 2013-256490, paragraphs 0008~0020 and 0038~0040 of Japanese Patent Publication No. 2013-116975, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359, paragraph 0008~ Paragraphs 0054 and 0101-0121, paragraphs 0007-0041 and 0060-0069 of JP 2014-9352, paragraphs 0008-0048 and 0067-0076 of JP 2014-9224, paragraphs 0013-0025 of JP 2017-119663, paragraphs 0013-0026 of JP 2017-119664, JP 2017- Examples include compounds included in the general formulas described in paragraphs 0012-0025 of Japanese Patent Publication No. 222623, paragraphs 0010-0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012-0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016-0044 of Japanese Patent Application Publication No. WO2018 / 047853, particularly exemplary compounds that emit delayed fluorescence.Also, Japanese Patent Publication 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, Publications WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133 Light-emitting materials that emit delayed fluorescence, as described in Publication No. 501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, can also be used. The above publications mentioned in this paragraph are incorporated herein by reference as part of this specification.

[0088] In the light-emitting layer, when a delayed fluorescence material is used as an assist dopant, a compound with a lower minimum excitation 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 multiple resonance effects between boron and nitrogen atoms, and compounds containing condensed aromatic ring structures such as anthracene, pyrene, and perylene. The delayed fluorescence materials exemplified above can also be used. In one preferred embodiment of the present invention, a compound represented by the following general formula (F1) is used as the luminescent material to be used in combination with the assist dopant. General formula (F1) [ka]

[0089] In the above general formula (F1), Ar 1 ~Ar 3 Each of these rings is 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. If a hydrogen atom is substituted, it is preferable that it is substituted with one or more groups selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group. If the rings are fused, it is preferable that a benzene ring or a heteroaromatic ring (e.g., a furan ring, a thiophene ring, a pyrrole ring, etc.) is fused. a and R a Each of the ' represents an independent substituent, preferably one 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 These elements may be bonded to each other to form a ring structure.

[0090] Compounds represented by general formula (F1) preferably contain at least one carbazole structure. For example, if one of the benzene rings constituting the carbazole structure is Ar 1 The ring may be represented as , and one of the benzene rings constituting the carbazole structure is Ar 2 The ring may be represented as , and one of the benzene rings constituting the carbazole structure is Ar 3 It may also be a ring represented by Ar. 1 ~Ar 3 One or more of these may have a carbazolyl group attached. For example, Ar 3A substituted or unsubstituted carbazole-9-yl group may be attached to the ring represented by .

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

[0092] Multiple skeletons represented by general formula (F1) may exist in a compound. For example, skeletons represented by general formula (F1) may be linked to each other via single bonds or linking groups. Furthermore, the skeleton represented by general formula (F1) may have additional structures exhibiting multiple resonance effects, where benzene rings are linked by boron, nitrogen, oxygen, and sulfur atoms.

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

[0094] In the general formula (F2), R 1 ~R 7 Each of these is independently a hydrogen atom, a deuterium atom, or a substituent. 1 ~R 7 At least one of these is preferably a group represented by the following general formula (F3). General formula (F3) [ka] In the general formula (F3), R 11 ~R 15 Each of the symbols represents an independent hydrogen atom, a deuterium atom, or a substituent, and * represents a bond position. The group represented by general formula (F3) is R of general formula (F2). 1 ~R 7 It may be one, two, or three. It may also be at least four, for example, four or five. In one preferred embodiment of the present invention, R 1 ~R 7 One of these is a group represented by the general formula (F3). In a preferred embodiment of the present invention, at least R 1 , R 3 , R 5 , R 7 This is a group represented by the general formula (F3). In one preferred embodiment of the present invention, R 1 , R 3 , R 4 , R 5 , R 7 Only is the group represented by the general formula (F3). In one preferred embodiment of the present invention, R 1 , R 3 , R 4 , R 5 , R 7 This is a group represented by the general formula (F3), and R 2 and R 4 R 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). In one aspect of the present invention, R 1 ~R 7 All of these are groups that can be represented by the general formula (F3). In one preferred embodiment of the present invention, R 1 and R 7 They are identical. In one preferred embodiment of the present invention, R 3 and R 5 They are identical. In one preferred embodiment of the present invention, R 2 and R 6 They are identical. In one preferred embodiment of the present invention, R 1 and R 7 They are identical, R 3 and R 5They are identical, and also, R 1 and R 3 They are different from each other. In one preferred embodiment of the present invention, R 1 , R 3 , R 5 , R 7 They are identical. In one preferred embodiment of the present invention, R 1 and R 4 and R 7 They are identical, R 3 Ya R 5 This is different. In one preferred embodiment of the present invention, R 3 and R 4 and R 5 They are identical, R 1 Ya R 7 This is different. In one preferred embodiment of the present invention, R 1 , R 3 , R 5 , R 7 All of these are R 4 It is different.

[0095] R of the general formula (F3) 11 ~R 15 Possible substituents include, for example, those selected from substituent group A, substituent group B, substituent group C, or substituent group D below. When a substituted amino group is selected as the substituent, a disubstituted amino group is preferred, and the two substituents on the amino group are preferably independently substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted alkyl groups, and are particularly preferred to be substituted or unsubstituted aryl groups (diarylamino groups). Possible substituents for the two aryl groups of the diarylamino group include, for example, those selected from substituent group A, substituent group B, substituent group C, or substituent group D below. The two aryl groups of the diarylamino group may be bonded to each other by a single bond or by a linking group, and the linking group referred to here is R 33 and R 34You can refer to the explanation of the linking group in the above. As a specific example of a diarylamino group, for example, a substituted or unsubstituted carbazole-9-yl group can be used. As a substituted or unsubstituted carbazole-9-yl group, for example, L of the above general formula (9) 11 We can list groups that are single-bonded. In one preferred embodiment of the present invention, R of general formula (F3) 13 Only R is a substituent, 11 , R 12 , R 14 , R 15 is a hydrogen atom. In a preferred embodiment of the present invention, R of general formula (F3) 11 Only R is a substituent, 12 , R 13 , R 14 , R 15 is a hydrogen atom. In a preferred embodiment of the present invention, R of general formula (F3) 11 and R 13 Only R is a substituent, 12 , R 14 , R 15 It is a hydrogen atom. R of the general formula (F2) 1 ~R 7 Among them is the R of the general formula (F3) 11 ~R 15 It may also contain a group in which all atoms are hydrogen atoms (i.e., a phenyl group). For example, R 2 , R 4 , R 6 It may be a phenyl group.

[0096] In the general formula (F2), R 8 and R 9 Preferably, each of these is independently 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, or a combination of two or more such groups. In a preferred embodiment of the present invention, R 8 and R 9 They are identical. In a preferred embodiment of the present invention, R 8 and R 9This atom is a halogen atom, and is particularly preferably a fluorine atom.

[0097] In one aspect of the present invention, R of general formula (F2) 1 ~R 9 Preferably, the total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present is three or more. For example, a compound with three or four such groups may be used. More preferably, the R of general formula (F2) 1 ~R 7 Preferably, the total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present is three or more. For example, a compound with three or four such groups may be used. In this case, R 8 and R 9 The alkoxy group, aryloxy group, and amino group may not be present. More preferably, the R of general formula (F2) 1 , R 3 , R 4 , R 5 , R 7 Preferably, the total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present is three or more. For example, a compound with three or four such groups may be used. In this case, R 2 , R 6 , R 8 , R 9 Alkoxy groups, aryloxy groups, and amino groups may not be present. In one preferred embodiment of the present invention, there are three or more substituted or unsubstituted alkoxy groups. In one preferred embodiment of the present invention, there are four or more substituted or unsubstituted alkoxy groups. In one preferred embodiment of the present invention, there is one or more substituted or unsubstituted alkoxy groups and two or more substituted or unsubstituted aryloxy groups. In one preferred embodiment of the present invention, there are two or more substituted or unsubstituted alkoxy groups and one or more substituted or unsubstituted amino groups. In one preferred embodiment of the present invention, R1 , R 4 , R 7 Each of these contains a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy. In a preferred embodiment of the present invention, R 1 , R 4 , R 7 Each of these groups may have a substituted or unsubstituted alkoxy group.

[0098] In one aspect of the present invention, R of general formula (F2) 1 ~R 9 The total number of substituents present in the molecule with a Hammett σp value of less than -0.2 is three or more. Examples of substituents with a Hammett σp value of less than -0.2 include the methoxy group (-0.27), ethoxy group (-0.24), n-propoxy group (-0.25), isopropoxy group (-0.45), and n-butoxy group (-0.32). On the other hand, fluorine atoms (0.06), methyl groups (-0.17), ethyl groups (-0.15), tert-butyl groups (-0.20), n-hexyl groups (-0.15), and cyclohexyl groups (-0.15) are not substituents with a Hammett σp value of less than -0.2. In one aspect of the present invention, R of general formula (F2) 1 ~R 9 Compounds with three substituents having a Hammett σp value of less than -0.2 can be used, or compounds with four substituents can be used. More preferably, the R of general formula (F2) 1 ~R 7 It is preferable that there are three or more substituents present in the compound with a Hammett σp value of less than -0.2; for example, a compound with three substituents or a compound with four substituents can be adopted. In this case, R 8 and R 9 It is not necessary for the substituent to have a Hammett σp value of less than -0.2. More preferably, the R of general formula (F2) 1 , R 3 , R 4 , R 5 , R 7It is preferable that the number of substituents present in the compound with a Hammett σp value of less than -0.2 is three or more; for example, a compound with three substituents or a compound with four substituents can be adopted. In this case, R 2 , R 6 , R 8 , R 9 It is not necessary for there to be substituents with a Hammett σp value of less than -0.2. In one preferred embodiment of the present invention, R 1 , R 4 , R 7 Each of these substituents has 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 luminescent material used in combination with the assist dopant. Alternatively, a compound that does not contain any of the carbazole, dibenzofuran, or dibenzothiophene structures may be selected as the luminescent material used in combination with the assist dopant.

[0100] The following are preferred compounds that can be used as luminescent materials in combination with assist dopants. However, the luminescent materials that can be used in combination with assist dopants in the present invention are not limited to the following specific examples. In the structural formulas of the following exemplary compounds, t-Bu represents a tert-butyl group. [ka] [ka] [ka]

[0101] Examples of derivatives of the above exemplary 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. Furthermore, the compounds described in paragraphs 0220-0239 of Publication No. WO2015 / 022974 can also be preferably used as luminescent materials in combination with assist dopants.

[0102] In one 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 used as a light-emitting material in combination with an assist dopant. The compound represented by general formula (G) may also be used as an assist dopant. General formula (G) [ka]

[0103] In general formula (G), X 1 and X 2 In this invention, one atom is a nitrogen atom and the other is a boron atom. In one aspect of the present invention, X 1 X is a nitrogen atom, 2 This is a boron atom. At this time, R 17 and R 18 They bond to each other to form a single bond and create a pyrrole ring. In another aspect of the present invention, X 1 X is a boron atom, 2 This is a nitrogen atom. In this case, R 21 and R 22 These elements bond to each other to form a single bond, creating a pyrrole ring.

[0104] In general formula (G), R 1 ~R 26 , A 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 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 [[ID=*56]], R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 [[ID=*72]] may be bonded to each other to form a cyclic structure. R 7 and R 8 The cyclic structure formed by the bond contains a boron atom and four carbon atoms as ring skeleton constituent atoms. R 17 and R 18 [[ID=8*2]]The cyclic structure formed by the bond is such that when X 1 is a boron atom, it contains a boron atom and four carbon atoms as ring skeleton constituent atoms. When X 1 is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. R 21 and R 22 The cyclic structure formed by the bond is such that when X[[ID=9*1]] 2 is a boron atom, it contains a boron atom and four carbon atoms as ring skeleton constituent atoms. When X 2 is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. R 7 and R 8 , R 17 and R 18 , R 21 Note: There seems to be an issue with the numbering in the original text. I've marked the lines where the numbering seems inconsistent (*). Please check the original text for accuracy.and R 22 When these elements bond to each other to form a cyclic structure containing boron atoms, 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 join with each other, they form a single bond, -O-, -S-, -N(R) 27 )-,-C(R 28 )(R 29 )-,-Si(R 30 )(R 31 )-,-B(R 32 It is preferable to form -, -CO-, -CS-, -O-, -S- or -N(R 27 It is more preferable to form -N(R 27 It is even more preferable to form )-. Here, R 27 ~R 32 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. As substituents, groups selected from substituent groups A to E described below may be used, but substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups are preferred, and in particular R 27 R is preferably a substituted or unsubstituted aryl group. 27 ~R 32 When R is a substituent, 7 and R 8 R in the ring formed by the bonding of these elements 27 ~R 32 is R 6 and R 9 It may further form a ring structure by bonding with at least one of the following: 17 and R 18 R in the ring formed by the bonding of these elements 27 ~R 32 is R 16 and R 19 It may further form a ring structure by bonding with at least one of the following: 21 and R 22 R in the ring formed by the bonding of these elements27 ~R 32 is R 20 and R 23 may be combined with at least one of them to further form a cyclic structure. In one aspect of the present invention, R 7 and R 8 、R 17 and R 18 、R 21 and R 22 Only one of the groups is bonded to each other. In one aspect of the present invention, R 7 and R 8 、R 17 and R 18 、R 21 and R 22 Only two of the groups are bonded to each other. In one aspect of the present invention, R 7 and R 8 、R 17 and R 18 、R 21 and R 22 All of them are bonded 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 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 22and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 The cyclic structure formed by the bonding of these rings may be an aromatic ring or an antilipid ring, may contain a heteroatom, and may have one or more other rings fused to it. The heteroatom here is preferably selected from the group consisting of nitrogen, oxygen, and sulfur atoms. 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 in which one or more rings selected from the group consisting of these rings are further fused to it. In one preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring (which may have further ring fusions), for example, a benzene ring which may be 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, 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 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 number of combinations that are bonded to each other to form a ring structure may be 0, or it may be any of 1 to 6, for example. For example, it may be any of 1 to 4, and one can choose 1, 2, 3 or 4. In one aspect of the present invention, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 A pair selected from these is joined together to form a ring structure. In one aspect of the present invention, R 5 and R 6 These are bonded together to form a ring structure. In one aspect of the present invention, R 9 and R 10 , R 10 and R 11 , R 11 and R 12 A pair selected from these is joined together to form a ring structure. In one aspect of the present invention, R 1 and R 2 , R 13 and R 14 In one aspect of the present invention, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 A pair selected from these elements is joined to each other to form a ring structure, and furthermore, R 5 and R 6 These are bonded together to form a ring structure. In one aspect of the present invention, R 5 and R6 , R 19 and R 20 They are all connected to each other, forming a ring structure.

[0106] Adjacent R n (n=1~26) and R that are not connected to each other 1 ~R 26 This is a hydrogen atom, a deuterium atom, or a substituent. As the substituent, a group selected from any of the substituent groups A to E described below can be used. R 1 ~R 26 The preferred substituents that can be adopted 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 alkyl groups, aryl groups, and heteroaryl groups referred to here may also be groups selected from substituent groups A to E, but preferably one or more groups selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, more preferably groups from substituent group E, and may be unsubstituted. In one preferred embodiment of the present invention, R 1 ~R 6 At least one of them is a substituent, preferably a group of substituent group E. For example, R 2 ~R 6 At least one of them is a substituent, preferably a group of substituent group E. For example, R 5 and R 6 At least one of them is a substituent, preferably a group of substituent group E. In a preferred embodiment of the present invention, R 3 and R 6 At least one of them is a substituent, more preferably both are substituents, and preferably they are groups of substituent group E. In one preferred embodiment of the present invention, X 1 When R is a nitrogen atom, 15 and R 20 At least one of them is a substituent, more preferably both are substituents, and preferably they are groups of substituent group E. In this case, R 17 and R 18They are bonded to each other to form a single bond. In one preferred embodiment of the present invention, X 2 When R is a nitrogen atom, 19 and R 24 At least one of them is a substituent, more preferably both are substituents, and preferably they are groups of substituent group E. In this case, R 21 and R 22 They are bonded to each other to form a single bond. In one aspect of the present invention, R 8 and R 12 At least one of them is a substituent, preferably both are substituents. In one aspect of the present invention, R 8 , R 10 and R 12 R is a substituent. 8 ~R 12 As substituents, unsubstituted alkyl groups are preferred. In particular, R 8 and R 12 When 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 is high when it is formed into a film, which is preferable. Among them, R 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, even 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 preferable that at least one of them is a substituent (preferably a group of substituent group E). 1 When is a boron atom, R 13 and R 17 At least one of them is a substituent, preferably both are substituents. In one aspect of the present invention, X 1 When is a boron atom, R 13 , R 15 and R 17 X is a substituent. 1 When is a boron atom, R 13 ~R 17 As the substituent, an unsubstituted alkyl group is preferred. 2When is a boron atom, R 22 and R 26 At least one of them is a substituent, preferably both are substituents. In one aspect of the present invention, X 2 When is a boron atom, R 22 , R 24 and R 26 X is a substituent. 2 When is a boron atom, R 22 ~R 26 As substituents, unsubstituted alkyl groups are preferred. Boron atoms represented as B in general formula (G), or X 1 or X 2 Specific examples of groups that bond to the boron atom represented by are given below. However, the groups that bond to the boron atom that can be used in the present invention are not limited to the following specific examples. Note that in this specification, the notation CH3 is omitted for methyl groups. * indicates the bond position. [ka]

[0107] In the following, R in general formula (G) 1 ~R 26 Let's give a specific example. R 1 ~R 7 , X 1 When R is a nitrogen atom 13 ~R 21 , X 2 When R is a nitrogen atom 18 ~R 26 Z1 to Z9 are preferred, R 8 ~R 12 , X 1 When R is a nitrogen atom 22 ~R 26 , X 2 When R is a nitrogen atom 13 ~R 17 Z1 to Z7 are preferred. However, the groups that can be used in the present invention to bond to boron atoms are not limited to the following specific examples. D represents a deuterium atom. * represents a bond position. [ka]

[0108] A 1 and A 2 This is a hydrogen atom, a deuterium atom, or a substituent. As the substituent, a group selected from any of the substituent groups A to E described below can be used. In one preferred embodiment of the present invention, A 1 and A 2 Each of these is either a hydrogen atom or a deuterium atom, independently of the others. For example, A 1 and A 2 A is a hydrogen atom. For example, A 1 and A 2 It is a deuterium atom. A 1 and A 2 One of them may be a substituent. Also, A 1 and A 2 Each of these may be an independent substituent. 1 and A 2 The preferred substituents that can be adopted are acceptor groups. Acceptor groups are groups with a positive Hammett σp value. A 1 and A 2The acceptor group that can be adopted is more preferably a group with a Hammett σp value greater than 0.2. Examples of groups with a Hammett σp value greater than 0.2 include cyano groups, aryl groups substituted with at least cyano groups, groups containing a fluorine atom, and substituted or unsubstituted heteroaryl groups containing a nitrogen atom as a ring skeleton component. The aryl group substituted with at least cyano groups may be substituted with substituents other than cyano groups (e.g., alkyl groups or aryl groups), but may also be an aryl group substituted only with cyano groups. The aryl group substituted with at least cyano groups is preferably a phenyl group substituted with at least cyano groups. The number of substitutions of the cyano group is preferably 1 or 2, for example, it may be 1 or it may be 2. Examples of groups containing a fluorine atom include a fluorine atom, an alkyl fluoride, and an aryl group substituted with at least a fluorine atom or an alkyl fluoride. The alkyl fluoride is preferably a perfluoroalkyl group, and the number of carbon atoms is preferably 1 to 6, more preferably 1 to 3. Furthermore, the heteroaryl group containing a nitrogen atom as a ring skeleton component may be a monoring or a fused ring formed by the fusion of two or more rings. In the case of a fused ring, the number of rings after fusion is preferably 2 to 6, for example, selected from 2 to 4, or set to 2. Specific examples of rings constituting the heteroaryl group include pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, quinoline rings, isoquinoline rings, quinazoline rings, quinoxaline rings, and naphthyridine rings other than quinazoline and quinoxaline rings. The rings constituting the heteroaryl group may be substituted with deuterium atoms or substituents. Examples of substituents include one group selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, or groups formed by a combination of two or more such groups. 1 and A 2 A particularly preferred acceptor group is the cyano group. In one aspect of the present invention, A 1 and A 2 At least one of them is an acceptor group. In one aspect of the present invention, A1 and A 2 Only one of them is an acceptor group. In one aspect of the present invention, A 1 and A 2 Both are the same acceptor group. In one aspect of the present invention, A 1 and A 2 These are different acceptor groups. In one aspect of the present invention, A 1 and A 2 A is a cyano group. In one aspect of the present invention, A 1 and A 2 These are halogen atoms, such as bromine atoms.

[0109] Specific examples of acceptor groups that can be used in the present invention are shown below. However, the acceptor groups that can be used in the present invention are not limited to the following examples. In this specification, the notation CH3 is omitted for methyl groups. Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups. Also, "D" represents a deuterium atom. * represents a bond position. [ka] [ka]

[0110] Note X 1 is a nitrogen atom, and R 7 and R 8 The nitrogen atoms bond to form a 6-membered ring, R 21 and R 22 The nitrogen atoms bond to form a 6-membered ring, R 17 and R 18 When R is bonded to each other to form a single bond, 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4and R 5 , R 5 and R 6 One of these rings is bonded to another to form an aromatic ring (a fused or substituted or unsubstituted benzene ring) or a heteroaromatic ring (preferably a fused or substituted or unsubstituted furan ring of benzofuran, or a fused or substituted or unsubstituted thiophene ring of benzothiophene). Also, X 1 X is a boron atom, 2 is a nitrogen atom, and R 7 and R 8 , R 17 and R 18 When these atoms are bonded to each other to form a cyclic structure containing boron atoms, the cyclic structure is a 5- to 7-membered ring, and if it is a 6-membered ring, then R 7 and R 8 , R 17 and R 18 They combine with each other to form -B(R 32 )-, -CO-, -CS- or -N(R 27 )- forms. R 27 Preferably, represents a hydrogen atom, a deuterium atom, or a substituent.

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

[0112] Each hydrogen atom in skeletons (1a) and (1b) may be substituted with a deuterium atom or a substituent. Alternatively, it may be substituted with adjacent hydrogen atoms to form a linking group, creating a cyclic structure. For details, see the corresponding R of general formula (G). 1 ~R 26 , A 1 , A 2You can refer to the description. Examples include compounds in which the phenyl groups bonded to the boron atom in skeletons (1a) and (1b) are both substituted with a mesityl group, a 2,6-diisopropylphenyl group, or a 2,4,6-triisopropylphenyl group. In one aspect of the present invention, each hydrogen atom in skeletons (1a) and (1b) is not substituted with an adjacent hydrogen atom to form a linking group and thus does not form a cyclic structure.

[0113] As a preferred group of compounds having the skeleton (1a), examples include compounds represented by the following general formula (1a). General formula (1a) [ka]

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

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

[0116] The following are specific examples of another group of compounds represented by general formula (1a). The compounds of general formula (1a) that can be used in the present invention are not limited to the following group of specific examples. [ka] [ka] [ka] [ka] [ka]

[0117] As a preferred group of compounds having the skeleton (1b), examples include compounds represented by the following general formula (1b). General formula (1b) [ka]

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

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

[0120] R in general formula (G) 7 and R 8 When these combine with each other to form N-Ph, the compound of the present invention is X 1 When is a nitrogen atom, for example, it has the following skeleton (2a), X 2 When is a nitrogen atom, it has, for example, the following skeleton (2b). Ph is a phenyl group. Skeleton (2a) [ka]

[0121] Each hydrogen atom in skeletons (2a) and (2b) may be substituted with a deuterium atom or a substituent. Alternatively, it may be substituted with adjacent hydrogen atoms to form a linking group, creating a cyclic structure. For details, see the corresponding R of general formula (G). 1 ~R 26 , A 1 , A 2You can refer to the description. At least one hydrogen atom of the benzene ring constituting the carbazole substructure contained in skeleton (2a) is substituted with a substituted or unsubstituted aryl group. In one aspect of the present invention, each hydrogen atom in skeletons (2a) and (2b) is not substituted with an adjacent hydrogen atom to form a linking group to form a cyclic structure.

[0122] As a preferred group of compounds having the skeleton (2a), examples include compounds represented by the following general formula (2a). General formula (2a) [ka]

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

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

[0125] As a preferred group of compounds having the skeleton (2b), examples include compounds represented by the following general formula (2b). General formula (2b) [ka]

[0126] In general formula (2b), Ar 15 ~Ar 20 Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferred. n15, n17, n18, and n20 each independently represent an integer from 0 to 4, and n16 and n19 each independently represent an integer from 0 to 2. A 1 , A 2 Each of these 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~n14, A 1 , A 2 You can refer to the descriptions in order.

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

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

[0129] Each hydrogen atom in skeletons (3a) and (3b) may be substituted with a deuterium atom or a substituent. Alternatively, it may be substituted with adjacent hydrogen atoms to form a linking group, creating a cyclic structure. For details, see the corresponding R of general formula (G). 1 ~R 26 , A 1 , A 2 You can refer to the description. In one aspect of the present invention, each hydrogen atom in skeletons (3a) and (3b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.

[0130] As a preferred group of compounds having the skeleton (3a), examples include compounds represented by the following general formula (3a). General formula (3a) [ka]

[0131] In general formula (3a), Ar 21 ~Ar 26 Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferably selected. n21, n23, n24, and n26 each independently represent an integer from 0 to 4, and n22 and n25 each independently represent an integer from 0 to 2. A 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 21 ~Ar 25 For details on n21~n25, see Ar in general formula (2a) 9 ~Ar 14 n9~n14, A 1 , A 2 You can refer to the description.

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

[0133] As a preferred group of compounds having the skeleton (3b), examples include compounds represented by the following general formula (3b). General formula (3b) [ka]

[0134] In general formula (3b), Ar 27 ~Ar 32 Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferred. n27, n29, n30, and n32 each independently represent an integer from 0 to 4, and n28 and n31 each independently represent an integer from 0 to 2. 1 , A 2 Each of these 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 You can refer to the descriptions in order.

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

[0136] In one preferred embodiment of the present invention, a compound is selected in which another ring is fused to two benzene rings constituting the carbazole substructure present in general formula (G). Among these, compounds in which a benfuran ring is fused, compounds in which a benzothiophene ring is fused, and compounds in which a benzene ring is fused are particularly preferred. These compounds in which the rings are fused will be described below with specific examples.

[0137] A preferred example is a compound in which a benzofuran ring or a benzothiophene ring is fused to the benzene ring that does not have a boron atom directly bonded to it, among the two benzene rings constituting the carbazole substructure present in general formula (G). Examples of such compounds include a compound having the following skeleton (4a) and a compound having the following skeleton (4b). [ka]

[0138] In the skeleton (4a) and (4b), Y 1 ~Y 4 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 This represents a state where the two hydrogen atoms, which are bonded to the boron atom, are not connected to each other. 1 and Y 2 They are the same, Y 3 and Y 4 It is preferable that they are the same, but they may be different. In one aspect of the present invention, Y 1 ~Y 4 is a single bond. In one aspect of the present invention, Y 1 ~Y 4 is N(R 27 ) is R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 1 ~Z 4 Each of these independently represents either an oxygen atom or a sulfur atom. 1 and Z 2 They are the same, Z 3 and Z 4It is preferable that they are the same, but they may be different. In one aspect of the present invention, Z 1 ~Z 4 is an oxygen atom. In this case, the furan ring of benzofuran is fused to the benzene ring that constitutes the carbazole substructure in (4a) and (4b). The orientation of the fused furan ring is not restricted. In one aspect 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 that constitutes the carbazole substructure in (4a) and (4b). The orientation of the fused thiophene ring is not restricted. Each hydrogen atom in skeletons (4a) and (4b) may be substituted with a deuterium atom or a substituent. Alternatively, it may be substituted with adjacent hydrogen atoms to form a linking group, creating a cyclic structure. For details, see the corresponding R of general formula (G). 1 ~R 26 , A 1 , A 2 You can refer to the description. In one aspect of the present invention, each hydrogen atom in skeletons (4a) and (4b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.

[0139] As a preferred group of compounds having the skeleton (4a), examples include compounds represented by the following general formula (4a). In the specific examples, X is either an oxygen atom or a sulfur atom, and compounds where X is an oxygen atom and compounds where X is a sulfur atom are disclosed, respectively. The same meaning applies to X in the specific examples of other compounds represented by the following general formulas. General formula (4a) [ka]

[0140] In general formula (4a), Ar 51 and Ar 52Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferably selected. 51 and R 52 Each of the following independently represents a substituted or unsubstituted alkyl group. m51 and m52 each independently represent an integer from 0 to 4. n51 and n52 each independently represent an integer from 0 to 2. Y 1 ~Y 4 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 Z represents a hydrogen atom, a deuterium atom, or a substituent. 1 ~Z 4 Each of these independently represents either an oxygen atom or a sulfur atom. 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. In one aspect 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 aspect of the present invention, m51 and m52 are the same number. In one aspect of the present invention, m51 and m52 are integers from 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. 51 Ar 52 , R 51 , R 52 , A 1 , A 2 As for the preferred group, the Ar of general formula (1a) 1 ~Ar 4 , R 41 ~R 42 , A 1 , A 2 You can refer to the corresponding description.

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

[0142] The following are specific examples of another group of compounds represented by general formula (4a). The compounds of general formula (4a) that can be used in the present invention are not limited to the following group of specific examples. [ka] [ka]

[0143] As a preferred group of compounds having the skeleton (4b), examples include compounds represented by the following general formula (4b). General formula (4b) [ka]

[0144] In general formula (4b), Ar 53 and Ar 54Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferably selected. 53 and R 54 Each of the following independently represents a substituted or unsubstituted alkyl group. m53 and m54 each independently represent an integer from 0 to 4. n53 and n54 each independently represent an integer from 0 to 2. Y 3 and Y 4 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 Z represents a hydrogen atom, a deuterium atom, or a substituent. 3 and Z 4 Each of these independently represents either an oxygen atom or a sulfur atom. 1 , A 2 Each of these 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 You can refer to the description.

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

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

[0147] In the skeleton (5a) and (5b), Y 5 ~Y 8 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents Z 5 ~Z 8 Each of these independently represents either an oxygen atom or a sulfur atom. 5 ~Y 8 , Z 5 ~Z 8 For further details, refer to the corresponding descriptions of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in skeletons (5a) and (5b) is not substituted with adjacent hydrogen atoms to form a linking group and thus does not form a cyclic structure.

[0148] As a preferred group of compounds having the skeleton (5a), examples include compounds represented by the following general formula (5a). General formula (5a) [ka]

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

[0150] Specific examples of compounds represented by general formula (5a) are given below. The compounds of general formula (5a) that can be used in the present invention are not limited to the following set of specific examples. For specific examples containing X, compounds in which all X atoms in the molecule are oxygen atoms and compounds in which all X atoms in the molecule are sulfur atoms are disclosed. Compounds in which some of the X atoms in the molecule are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka] [ka] [ka]

[0151] The following are specific examples of another group of compounds represented by general formula (5a). The compounds of general formula (5a) that can be used in the present invention are not limited to the following group of specific examples. [ka]

[0152] As a preferred group of compounds having the skeleton (5b), examples include compounds represented by the following general formula (5b). General formula (5b) [ka]

[0153] In general formula (5b), Ar 57 and Ar 58 Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferably selected. 57 and R 58 Each of the following independently represents a substituted or unsubstituted alkyl group. m57 and m58 each independently represent an integer from 0 to 4. n57 and n58 each independently represent an integer from 0 to 4. Y 7 and Y 8 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 Z represents a hydrogen atom, a deuterium atom, or a substituent. 7 and Z 8Each of these independently represents either an oxygen atom or a sulfur atom. 1 , A 2 Each of these 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 You can refer to the description.

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

[0155] The following are specific examples of another group of compounds represented by general formula (5b). The compounds of general formula (5b) that can be used in the present invention are not limited to the following specific examples. [ka] [ka]

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

[0157] In the skeleton (6a) and (6b), Y 9 ~Y 12 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents Z 9 ~Z 16 Each of these independently represents either an oxygen atom or a sulfur atom. 9 ~Z 16 It is preferable that they be the same, but they may be different. In one aspect of the present invention, Z 9 ~Z 16 is an oxygen atom. In one aspect of the present invention, Z 9 ~Z 16 This is a sulfur atom. 9 ~Y 12 For further details, refer to the corresponding descriptions of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in skeletons (6a) and (6b) is not substituted with adjacent hydrogen atoms to form a linking group and thus does not form a cyclic structure.

[0158] As a preferred group of compounds having the skeleton (6a), examples include compounds represented by the following general formula (6a). General formula (6a) [ka]

[0159] In general formula (6a), R 59 and R 60 Each of these independently represents a substituted or unsubstituted alkyl group. m59 and m60 each independently represent an integer from 0 to 4. 9and Y 10 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 Z represents a hydrogen atom, a deuterium atom, or a substituent. 9 ~Z 12 Each of these independently represents either an oxygen atom or a sulfur atom. 1 , A 2 Each of these 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 the skeleton (6a) 9 ~Z 12 You can refer to the description.

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

[0161] As a preferred group of compounds having the skeleton (6b), examples include compounds represented by the following general formula (6b). General formula (6b) [ka]

[0162] In general formula (6b), R 61 and R 62 Each of these independently represents a substituted or unsubstituted alkyl group. m61 and m60 each independently represent an integer from 0 to 4. 11 and Y 12 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 Z represents a hydrogen atom, a deuterium atom, or a substituent. 13 ~Z 16 Each of these independently represents either an oxygen atom or a sulfur atom. 1 , A 2 Each of these 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 the skeleton (6b) 13 ~Z 16 You can refer to the description.

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

[0164] A preferred example is a compound in which a benzene ring is fused to the benzene ring that does not have a boron atom directly bonded to it, among the two benzene rings that constitute the carbazole substructure 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). [ka]

[0165] In the skeleton (7a) and (7b), Y 21 ~Y 24 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents Y 21 ~Y 24 For details, see the Y of the skeleton (4a) and (4b) 1 ~Y 4 You can refer to the description. In one aspect of the present invention, each hydrogen atom in skeletons (7a) and (7b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.

[0166] As a preferred group of compounds having the skeleton (7a), examples include compounds represented by the following general formula (7a). General formula (7a) [ka]

[0167] In general formula (7a), Ar 71 ~Ar 74Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted aryl group can be preferred. n71 and n73 each independently represent an integer from 0 to 2. n72 and n74 each independently represent an integer from 0 to 4. Y 21 and Y 22 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 A represents a hydrogen atom, a deuterium atom, or a substituent. 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. In one aspect of the present invention, n71 to n74 are integers between 0 and 2. In one aspect of the present invention, n71 and n73 are the same number, and n72 and n74 are the same number. n71 to n74 may also be the same number. For example, n71 to n74 may all be 0. n71 to n74 may all be 1. Also, for example n71 and n73 may be 0, and n72 and n74 may be 1. 71 ~Ar 74 , A 1 , A 2 As for the preferred group, the Ar of general formula (1a) 1 ~Ar 4 , A 1 , A 2 You can refer to the corresponding description.

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

[0169] As a preferred group of compounds having the skeleton (7b), examples include compounds represented by the following general formula (7b). General formula (7b) [ka]

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

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

[0172] A preferred example is a compound in which a benzene ring is fused to the benzene ring to which a boron atom is directly bonded, among the two benzene rings that constitute the carbazole substructure 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). [ka]

[0173] In the skeleton (8a) and (8b), Y 25 ~Y 28 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents Y 25 ~Y 28 For further details, refer to the corresponding descriptions of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in skeletons (8a) and (8b) is not substituted with adjacent hydrogen atoms to form a linking group to form a cyclic structure.

[0174] As a preferred group of compounds having the skeleton (8a), examples include compounds represented by the following general formula (8a). General formula (8a) [ka]

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

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

[0177] As a preferred group of compounds having the skeleton (8b), examples include compounds represented by the following general formula (8b). General formula (8b) [ka]

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

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

[0180] Compounds in which benzene rings are fused to both of the two benzene rings constituting the carbazole substructure present in general formula (G) are preferred. Examples of such compounds include the compound having the following skeleton (9a) and the compound having the following skeleton (9b). [ka]

[0181] In the skeleton (9a) and (9b), Y 29 ~Y 32 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents Y 29 ~Y 32 For further details, refer to the corresponding descriptions of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in skeletons (9a) and (9b) is not substituted with adjacent hydrogen atoms to form a linking group and thus does not form a cyclic structure.

[0182] As a preferred group of compounds having the skeleton (9a), examples include compounds represented by the following general formula (9a). General formula (9a) [ka]

[0183] In general formula (9a), R 75 and R 76 Each of these independently represents a substituted or unsubstituted alkyl group. m75 and m76 each independently represent an integer from 0 to 4. Y 29 and Y 30 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 A represents a hydrogen atom, a deuterium atom, or a substituent. 1 , A 2 Each of these 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 You can refer to the description.

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

[0185] As a preferred group of compounds having the skeleton (9b), examples include compounds represented by the following general formula (9b). General formula (9b) [ka]

[0186] In general formula (9b), R 77 and R 78 Each of these independently represents a substituted or unsubstituted alkyl group. m77 and m78 each independently represent an integer from 0 to 4. Y 31 and Y 32 Each of these consists of two hydrogen atoms, bonded together by a single bond or N(R) 27 ) represents R 27 A represents a hydrogen atom, a deuterium atom, or a substituent. 1 , A 2 Each of these 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 You can refer to the description.

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

[0188] Compounds represented by general formula (G) that contain four or more carbazole substructures within the molecule are also preferred. Examples of such compounds include those having the following skeleton (10). Skeleton (10) [ka]

[0189] Each hydrogen atom in skeleton (10) may be substituted with a deuterium atom or a substituent. Alternatively, it may be substituted with adjacent hydrogen atoms to form a linking group, creating a cyclic structure. For details, see the corresponding R in general formula (G). 1 ~R 26 , A 1 , A 2 You can refer to the description. At least one hydrogen atom of the benzene ring constituting the carbazole substructure contained in the skeleton (10) is substituted with a substituted or unsubstituted aryl group. In one aspect of the present invention, each hydrogen atom in the skeleton (10) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.

[0190] As a preferred group of compounds having a skeleton (10), examples include compounds represented by the following general formula (10). General formula (10) [ka]

[0191] In 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, for example, a substituted or unsubstituted aryl group can be preferred. n91 and n93 each independently represent an integer from 0 to 4, and n92 and n94 each independently represent an integer from 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. 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. In one aspect of the present invention, n91 to n94 are integers between 0 and 2. In one aspect 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, they may all be 0 or they may all be 1. 91 ~Ar 94 As for the preferred group, the Ar of general formula (1a) 1 ~Ar 4You can refer to the corresponding description. In one aspect of the present invention, the α-ring and γ-ring have the same substituent or the same condensation structure, and the β-ring and δ-ring have the same substituent or the same condensation structure. In one aspect of the present invention, both the β-ring and δ-ring are substituted with substituted or unsubstituted aryl groups, or are fused with an optionally substituted benzene ring, or are fused with a substituted or unsubstituted furan ring of benzofuran or a substituted or unsubstituted thiophene ring of thiophene. In one aspect of the present invention, both the α-ring and γ-ring are substituted with substituted or unsubstituted aryl groups, or are fused with an optionally substituted benzene ring, or are fused with a substituted or unsubstituted furan ring of benzofuran or a substituted or unsubstituted thiophene ring of thiophene. In one aspect of the present invention, all of the α-ring, β-ring, γ-ring, and δ-ring are substituted with substituted or unsubstituted aryl groups, or are fused with an optionally substituted benzene ring, or are fused with a substituted or unsubstituted furan ring of benzofuran or a substituted or unsubstituted thiophene ring of thiophene. A 1 and A 2 For an explanation and preferred range, refer to the corresponding description in general formula (G).

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

[0193] Compounds represented by general formula (G) may have a symmetry skeleton. For example, they may be compounds having an asymmetric skeleton such as the following skeletons (11a) or (11b). [ka]

[0194] In the skeleton (11a) and (11b), Z 17 and Z 18 Each of these independently represents either an oxygen atom or a sulfur atom. In one aspect of the present invention, each hydrogen atom in the skeleton (11a) and (11b) is not substituted with an adjacent hydrogen atom to form a linking group and thus does not form a cyclic structure.

[0195] As a preferred group of compounds having the skeleton (11a), examples include compounds represented by the following general formula (11a). General formula (11a) [ka]

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

[0197] Specific examples of compounds 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, compounds in which all X atoms in the molecule are oxygen atoms and compounds in which all X atoms in the molecule are sulfur atoms are disclosed, respectively. Compounds in which some of the X atoms in the molecule are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0198] As a preferred group of compounds having the skeleton (11b), examples include compounds represented by the following general formula (11b). General formula (11b) [ka]

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

[0200] Specific examples of compounds represented by general formula (11b) are given below. The compounds of general formula (11b) that can be used in the present invention are not limited to the following specific examples. In the following specific examples, compounds in which all X atoms in the molecule are oxygen atoms and compounds in which all X atoms in the molecule are sulfur atoms are disclosed, respectively. Compounds in which some of the X atoms in the molecule are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0201] As a compound represented by general formula (G), R 5 Compounds in which the donor group is preferably used. 5 Compounds in which R is the donor group tend to have a high molar extinction coefficient and high luminescence efficiency. For example, R 3 It exhibits superior luminescence properties compared to compounds in which R is a donor group. In one preferred embodiment of the present invention, R 3 is not a donor group. In one preferred embodiment of the present invention, R 1 ~R 7 Among them, R 5 Only one of them is a donor group, or none of them are donor groups (especially donor groups with a σp value of -0.2 or less). A donor group is a group with a negative Hammett σp value. R 5The donor group preferably has a σp value of -0.2 or less, for example, it may be -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 monoring or a fused ring formed by the fusion of two or more rings. In the case of a fused ring, the number of rings after fusion is preferably 2 to 6, for example, it can be selected from 2 to 4, or set to 2. The two aryl groups constituting the diarylamino group may be the same or different. Also, 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 carbazole-9-yl group in which two phenyl groups are linked by a single bond may be used, or a substituted or unsubstituted diphenylamino group in which two phenyl groups are not linked by a single bond may be used. R of general formula (G) 1 ~R 7 When any of the groups is a substituted amino group, at least R 5 It is preferable that R is a substituted amino group. 5 It is more preferable that only R is a substituted amino group. In one aspect of the present invention, 3 It is not a substituted amino group. R 5 X is a donor group, 1 When R is a nitrogen atom, 16 or R 19 It is preferable that R is a donor group. 19 It is more preferable that the donor group is. In this case, other R 1 ~R 26 For example, all of them could be hydrogen atoms or deuterium atoms, or for example, R 3 , R 6 , R 15 , R 20 At least one of the atoms 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. R 5X is a donor group, 1 When is a boron atom, R 20 or R 23 It is preferable that R is a donor group. 20 It is more preferable that the donor group is. In this case, other R 1 ~R 26 For example, all of them could be hydrogen atoms or deuterium atoms, or for example, R 3 , R 6 , R 19 , R 24 At least one of the atoms 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. R 5 As a preferred group of compounds in which is a donor group, examples include the compounds represented by the following general formula (12a) and the compounds represented by the following general formula (12b). General formula (12a) [ka]

[0202] In general formulas (12a) and (12b), Ar 1 ~Ar 8 Each of these independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group. For example, a substituted or unsubstituted alkyl group may be preferred, or a substituted or unsubstituted aryl group may be preferred. 5 R represents the donor group. 41 ~R 44 Each of these independently represents a substituted or unsubstituted alkyl group. m1 to m4 each independently represents an integer from 0 to 5. n1, n3, n5, and n7 each independently represent an integer from 0 to 4, n4 and n8 each represent an integer from 0 to 3, and n2' and n6' each represent an integer from 0 to 2. A 1 , A 2 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 ~Ar 8 , R 41~R 44 , m1~m4, n1, n3~n5, n7, n8, A 1 , A 2 For further details, refer to the corresponding descriptions of general formula (1a) and general formula (1b). However, Ar bonded to adjacent carbon atoms 1 Ar 3 Ar 5 Ar 7 These molecules may be bonded to each other to form a cyclic structure, preferably forming benzofuran (condensed at a furan ring) or benzothiophene (condensed at a thiophene ring).

[0203] Specific examples of compounds represented by general formulas (12a) and (12b) are given below. However, the compounds of general formulas (12a) and (12b) that can be used in the present invention are not limited by the following examples. In the following 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 formula F1 where R is A and Ar is a.

[0204] [ka] [ka] [ka] [ka] [ka] [ka] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9]

[0205] [ka]

[0206] In one aspect of the present invention, the above skeleton (1a) to (12b) is a skeleton in which no other rings are further fused. In one aspect of the present invention, the above skeleton (1a) to (12b) is a skeleton in which no other rings are further fused. The other rings referred to here are as described 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 You can refer to the description of the annular structure formed by the bonding of these elements together.

[0207] In one aspect of the present invention, A of general formula (G) 1 and A 2 This is an acceptor group. For example, A 1 and A 2 The position at is an acceptor group, and examples of compounds having any of the skeletons (1a) to (12b) can be given. For an explanation and specific examples of acceptor groups, see A of the general formula (G) above. 1 and A 2 You can refer to the explanation and specific examples of acceptor groups. In the following, A 1 and A 2 Specific examples of compounds in which A is an acceptor group are given. A that can be used in the present invention 1 and A 2 Compounds in which A is an acceptor group are not interpreted restrictively by the following specific examples. The following specific examples are A 1 and A 2 Both compounds have a structure in which "A" is present, and the structure of each compound is identified by individually identifying this "A". [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0208] In one aspect of the present invention, a compound having a rotationally symmetric structure is selected as the compound represented by general formula (G). In one aspect of the present invention, a compound having a lineally symmetric structure is selected as the compound represented by general formula (G). In one aspect of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (G). The following are specific examples of compounds having an asymmetric skeleton. Compounds having an asymmetric skeleton or asymmetric structure that can be used in the present invention are not limited to the following specific examples. For specific examples containing X, it is assumed that compounds in which all X atoms in the molecule are oxygen atoms and compounds in which all X atoms in the molecule are sulfur atoms are disclosed. Compounds in which some of the X atoms in the molecule are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka] [ka]

[0209] The following are specific examples of compounds that have a symmetrical skeleton but an asymmetrical structure due to the asymmetrical bonding of substituents. The compounds with asymmetrical structures that can be used in the present invention are not limited to the following examples. [ka] [ka]

[0210] In one aspect of the present invention, R of general formula (G) 3 is not a diarylamino group (the two aryl groups constituting the diarylamino group may be bonded to each other). In a preferred embodiment of the present invention, R of general formula (G) 3 This is a hydrogen atom, a deuterium atom, or an acceptor group (not a donor group). In one aspect of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or more. In a preferred aspect of the present invention, at least one of m1 and m2 in general formula (1a) is 1 or more. In a further preferred aspect of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or more, and at least one of m1 and m2 in general formula (1a) is 1 or more. In one aspect of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or more. In a preferred aspect of the present invention, at least one of m3 and m4 in general formula (1b) is 1 or more. In a further preferred aspect of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or more, and at least one of m3 and m4 in general formula (1a) is 1 or more. When at least one of the above 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 R43 and R 44 Preferably, at least one of them is an alkyl group which may be substituted with a deuterium atom, for example R 41 ~R 44 All of them are alkyl groups which may be substituted with deuterium atoms. When at least one of the above n1 to n4 is 1 or more and at least one of n5 to n8 is 1 or more, Ar 1 ~Ar 4 At least one of and Ar 5 ~Ar 8 Preferably, at least one of them is an aryl group which may be substituted with a deuterium atom or an alkyl group, for example Ar 1 ~Ar 8 All of these are aryl groups, which may be substituted with deuterium atoms or alkyl groups. In one aspect of the present invention, X of general formula (G) 1 R is a boron atom 8 , R 10 , R 12 , R 13 , R 15 , R 17 When is an alkyl group (or methyl group), R 1 ~R 7 , R 18 ~R 20 , R 23 ~R 26 At least one of them is a substituent, preferably a group of substituent group E, which may be substituted with a deuterium atom or an alkyl group, for example. In one aspect of the present invention, X of general formula (G) 2 R is a boron atom 8 , R 10 , R 12 , R 22 , R 24 , R 26 When is an alkyl group (or methyl group), R 1 ~R 7 , R 13 ~R 16 , R 19 ~R 21 At least one of the substituents is a substituent, preferably a group of substituent group E, which may be an aryl group substituted with, for example, a deuterium atom or an alkyl group. In one aspect of the present invention, X of general formula (G) 1 This is a boron atom, R 8 and R 9 , R 9 and R 10 One of the following pairs, and R 15 and R 16 , R 16 and R 17 When any one pair of these is bonded to each other to form an aromatic ring (or benzene ring), R 1 ~R 7 , R 18 ~R 20 , R 23 ~R 26 At least one of them is a substituent, preferably a group of substituent group E, which may be substituted with a deuterium atom or an alkyl group, for example. In one aspect of the present invention, X of general formula (G) 2 This is a boron atom, R 8 and R 9 , R 9 and R 10 One of the following pairs, and R 22 and R 23 , R 23 and R 24 When any one pair of these is bonded to each other to form an aromatic ring (or benzene ring), R 1 ~R 7 , R 13 ~R 16 , R 19 ~R 21 At least one of the substituents is a substituent, preferably a group of substituent group E, which may be an aryl group substituted with, for example, a deuterium atom or an alkyl group. In one aspect of the present invention, R of general formula (G) 9 and R 11 It is neither a cyano group nor an alkyl group. That is, R 9 and R 11 R is a hydrogen atom, a deuterium atom, or a substituent other than a cyano group and an alkyl group. In one aspect of the present invention, R of general formula (G) 9 and R 11 It is neither a cyano group nor a tert-butyl group. In one preferred embodiment of the present invention, R of general formula (G) 8 ~R 12At least one of them is a substituent. In one aspect of the present invention, R of general formula (G) 3 is not a substituted amino group or aryl group. In one aspect of the present invention, R of general formula (G) 3 is not a substituted amino group or a phenyl group. In one aspect of the present invention, R of general formula (G) 3 It is not a dimethylamino group, a diphenylamino group, or a phenyl group. In one preferred embodiment of the present invention, R of general formula (G) 1 ~R 26 At least one of them is a substituent, more preferably R 1 ~R 26 At least one of them is an alkyl group, for example, an alkyl group having 1 to 4 carbon atoms.

[0211] (base material) In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, which is not particularly limited and may be any of the materials commonly used in organic electroluminescent elements, such as glass, transparent plastic, quartz, and silicon.

[0212] (anode) In some embodiments, the anode of an organic electroluminescent apparatus is manufactured from a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is manufactured by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, if the pattern does not need to be highly precise (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, wet film formation methods such as printing or coating methods are used. In some embodiments, when synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms or less per unit area. 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-injection metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of the electron-injection metal and a second metal that is a stable metal having a higher work function than the electron-injection metal is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or cathode of the organic electroluminescent element is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, a transparent or translucent electroluminescent element enhances the light radiance. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with respect to the conductive transparent material described above. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[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 includes a hole injection layer and an electron injection layer. The injection layer can be located between the anode and the light-emitting layer or hole transport layer, and between the cathode and the light-emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0215] [ka]

[0216] Next, we will list some examples of preferred compounds that can be used as electron injection materials. [ka]

[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 to the outside of the light-emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole transport layer, preventing electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron transport layer, preventing holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing to the outside of the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the terms “electron barrier layer” or “exciton barrier layer” include layers that have both the functions of an electron barrier layer and an exciton barrier layer.

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

[0219] [ka]

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

[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 properties and electron barrier properties. 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, indrocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, aminosubstituted 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 porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. 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 given below.

[0222] [ka]

[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 have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier 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, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole inducer 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] [ka]

[0225] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0226] [ka]

[0227] While specific examples of preferred materials that can be used in organic electroluminescent elements have been provided, the materials that can be used in the present invention are not limited to the exemplified compounds. Furthermore, even compounds exemplified as materials with specific functions can be repurposed as materials with other functions. Each organic layer of an organic electroluminescent element can be formed by a wet process. In the wet process, a solution containing a composition comprising the compounds that make up the organic layer is applied to a surface, and the layer is formed after the solvent is removed. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the compounds that make up the organic layer is selected and used. In some embodiments, substituents (e.g., alkyl groups) that increase the solubility in the organic solvent can be introduced into the compounds that make up the organic layer. In one embodiment, the organic layer can be formed by a dry process. In another embodiment, a vacuum deposition method can be used as the dry process, but is not limited to this. When a vacuum deposition method is used, the compounds constituting the organic layer may be co-deposited from individual deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compressed molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In one embodiment, by performing co-deposition under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, an organic layer with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. By mixing multiple compounds in the same composition ratio as the composition ratio of the formed organic layer to create a deposition source, an organic layer with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound has the same weight loss rate can be identified, and that temperature can be adopted as the temperature during co-deposition.

[0228] [device] In some embodiments, the light-emitting layer is incorporated into the 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 includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the components described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the components may be useful for facilitating charge transfer or energy transfer within the device and / or as hole transport materials. Examples of such devices include 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-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0229] [Bulb or lamp] In some embodiments, the electronic device includes an OLED comprising an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, and blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is A circuit board having a first surface with a mounting surface and a second surface opposite to it, defining at least one opening, The mounting surface comprises at least one OLED having a light-emitting configuration, wherein the at least one OLED includes an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, A housing for a circuit board, An OLED light comprising at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some of the light emitted in the 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] [Display or screen] In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compound according to the present invention is deposited on a substrate using a process such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD), but is not limited. In some embodiments, the substrate is a photoplate structure useful in two-sided etching, providing pixels with a unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern allows for the arrangement of very steep, narrow tie bars between pixels in the vertical direction, as well as large, wide oblique apertures in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays, while optimizing chemical vapor deposition on a TFT backplane. Internal patterning of pixels allows for the creation of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within a pixel area protects etching in specific areas until these particular patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at a similar etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone patterns, etching with varying degrees of protection within the pixel becomes possible, enabling localized deep etching necessary to form steep vertical bevels. A preferred material for deposition masks is Invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming openings within 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, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from 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, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel.

[0232] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method being A process of forming a barrier layer on the base substrate of the mother panel, The process of forming multiple display units on the barrier layer in cell panel units, The process of forming an encapsulation layer on each of the display units of the cell panel, The process includes the step of applying an organic film to the interface portion between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edges of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in the 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 a 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, wherein the organic film coated on the interface portion is formed 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 unit is connected to the TFT layer by a passivation layer, a planarization film between them, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to the display unit or the encapsulation layer.

[0233] Each of the organic film and the planarization film may contain either polyimide or 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 the steps of attaching a carrier substrate made of glass material to another surface of the base substrate before forming a barrier layer on one surface of the polyimide 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 placed on the TFT layer for coating the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is made of polyimide or acrylic, as is the organic film formed at the edges of the barrier layer. 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 at the edges of the barrier layer, so that a portion of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges 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 the source / drain electrodes 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 having a TFT layer and a light-emitting unit will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display unit and preventing the penetration of external moisture may be formed as a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the edges of the barrier layer while also being in contact with 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 glass material, and then the carrier substrate is separated. In some embodiments, the 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 interface 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 portion, where a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, a TFT layer is formed for each cell panel, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on the TFT layer and cover the TFT layer. At the same time that a planarization film made of, for example, polyimide or acrylic is formed, the groove in the interface portion is covered with an organic film made of, for example, polyimide or acrylic. This prevents cracking by allowing the organic film to absorb the impact generated when each cell panel is cut along the groove at the interface portion. That is, if all barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the impact generated is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between barrier layers may be covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel is cut softly and cracking in the barrier layer is prevented. In one embodiment, the organic film and the planarizing film covering the grooves of the interface portion are arranged with a gap between them. For example, if the organic film and the planarizing film are connected to each other as a single layer, there is a risk that external moisture may penetrate the display unit through the remaining parts of the planarizing film and organic film. Therefore, the organic film and the planarizing film are arranged with a gap between them so that the organic film is spaced away from the display unit.

[0237] In some embodiments, the display unit is formed by the formation of a light-emitting unit, and an encapsulation layer is placed on the display unit to cover it. This separates the carrier substrate supporting the base substrate from the base substrate after the mother panel is completely manufactured. In some embodiments, when a laser beam is emitted onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficients between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface between cell panels using a cutter. In some embodiments, the grooves of the interface along which the mother panel is cut are covered with an organic film so that the organic film absorbs the impact during cutting. In some embodiments, cracking can be prevented in the barrier layer during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film coated on the edges of the barrier layer. [Examples]

[0238] The features of the present invention will be further described in detail below with reference to synthesis examples and embodiments. The materials, processing content, 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 interpreted as being limited by the specific examples shown below. The luminescence characteristics were evaluated using a source meter (Keithley Corporation: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334).

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

[0240] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (2 g, 6.19 mmol), 3-phenyl-12H-benzofl[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 (eluent: chloroform / n-hexane = 5:5). Further recrystallization (toluene / methanol) yielded compound 1b as a white solid (1.74 g, 49%). 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 [ka]

[0242] Under a nitrogen atmosphere and ice bath, N-bromosuccinimide (13.8 g, 77.7 mmol) was added to a chloroform solution (900 mL) of 12H-benzofl[2,3-a]carbazole (20.0 g, 77.7 mmol), and the mixture was stirred for 14 hours at room temperature. 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 in toluene and chlorobenzene, respectively, to obtain the white solid intermediate M1 (15.9 g, 61%). 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] [ka]

[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 water was filtered. The obtained 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, intermediate M2 (10.8 g, 69%) was obtained by recrystallization in toluene and chlorobenzene, respectively. 1 H-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] [ka]

[0246] Under a nitrogen atmosphere, a toluene solution (240 mL) containing 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. Compound 2b was obtained by recrystallization of the obtained solids with chlorobenzene and toluene, respectively (12.4 g, 65%). 1 H 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, 1.2Hz, 1H) MS (ASAP): 576.37 (M+H + Calcd for C 42 H 25 NO2: 575.19.

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

[0248] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (1.78 g, 5.5 mmol), 2-phenyl-12H-benzofl[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 (eluent: chloroform / n-hexane = 3:7). Further recrystallization (toluene / methanol) yielded compound 6b as a white solid (2.24 g, 77%). 1 H 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 [ka]

[0250] Under a nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (0.97 g, 3 mmol), 2-phenyl-5H-benzofl[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 (eluent: chloroform / n-hexane = 2:8). Further recrystallization (toluene / methanol) yielded compound 19b as a white solid (1.09 g, 63%). 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 thickness of 50 nm has been formed, the following thin films were deposited by vacuum deposition at a vacuum of 5.0 × 10⁻⁶. -5 Organic electroluminescent elements were fabricated by stacking layers of Pa. First, HAT-CN was formed to a thickness of 10 nm on ITO, then NPD was formed to a thickness of 30 nm on top of it, and compound 1b was further formed to a thickness of 10 nm on top of that. Next, a host material (H1) and a delayed fluorescence material (T132) were co-deposited from different deposition sources to form a 40 nm thick layer which served as the light-emitting layer. At this time, the host material content was 65 mass%, and the delayed fluorescence material content was 35 mass%. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different deposition sources to form a 30 nm thick layer. The Liq and SF3-TRZ content in this layer was 30 mass% and 70 mass%, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode, thereby fabricating an organic electroluminescent element. This element was designated as EL element 1. Furthermore, organic electroluminescent elements were fabricated using the same procedure as before, with the only change being the use of compounds 6b, 19b, and 22 instead of compound 1b, and these were designated as EL elements 2 to 4. Furthermore, organic electroluminescent elements were fabricated using the same procedure as before, except that comparative compounds A and B were used instead of compound 1b. These were designated as comparative EL element 1 and comparative EL element 2, respectively. When current was passed through each fabricated organic electroluminescent element, delayed fluorescence originating from the delayed fluorescence material (T132) was observed. Each organic electroluminescent element was subjected to a current density of 12.6 mA / cm². 2 The device was driven, and the time (LT95) until the luminescence intensity reached 95% of the initial level was measured. The measurement results are shown in Table 2. In Table 2, LT95 is shown as a relative value with the LT95 of comparative EL element 2 set to 1. The measurement results show that when the compound represented by general formula (1) is used as the electron barrier material, the device lifetime is significantly longer than when comparative compounds A and B, which are conventionally used as electron barrier materials.

[0252] [Table 2]

[0253] (Example 2) The only modification to Example 1 was that the light-emitting layer was replaced with a 40 nm thick light-emitting layer in which the host material (H1), delayed fluorescence material (T132), and fluorescence material (E1) were co-deposited from different deposition sources, with content amounts of 64.2% by mass, 35.0% by mass, and 0.8% by mass, respectively. Otherwise, an organic electroluminescent element was fabricated using the same procedure as in Example 1. This element was designated as EL element 5. Furthermore, organic electroluminescent elements were fabricated using the same procedure as before, with the only change being the use of compounds 2b and 19b instead of compound 1b, and these were designated as EL elements 6 and 7, respectively. When current was passed through each of the fabricated organic electroluminescent elements, delayed fluorescence originating from the fluorescent material (E1) was observed. The fabricated organic electroluminescent elements were subjected to a current of 6.3 mA / cm². 2 The external quantum efficiency (EQE) and initial drive voltage were measured by driving the device with a current density of 12.6 mA / cm². 2 The device was driven, and the time (LT95) until the luminescence intensity reached 95% of the initial level was measured. The measurement results are shown in Table 3. In Table 3, EQE and LT95 are shown as relative values ​​with LT95 of EL element 7 set to 1, and the drive voltage is shown as a relative value with EL element 7 as the reference (0). The measurement results show that even when a host material, a delayed fluorescence material, and a fluorescent material are used in the light-emitting layer, devices using the compound represented by general formula (1) as the electron barrier material all exhibit high luminescence efficiency, low drive voltage, and long device lifetime.

[0254] [Table 3]

[0255] (Example 3) The only modification to the light-emitting layer of Example 1 was that the host material (H1) and the delayed fluorescence material (T136) were co-deposited from different deposition sources, resulting in a 40 nm thick light-emitting layer with content of 65% by mass and 35% by mass, respectively. Otherwise, an organic electroluminescent element was fabricated using the same procedure as in Example 1. This element was designated as EL element 8. Furthermore, organic electroluminescent elements were fabricated using the same procedure as before, with the only change being the use of compound 2b instead of compound 1b, and these were designated as EL elements 9. When current was passed through each of the fabricated organic electroluminescent elements, delayed fluorescence originating from the delayed fluorescence material (T136) was observed. The fabricated organic electroluminescent elements were subjected to a current of 6.3 mA / cm². 2 The external quantum efficiency (EQE) and initial drive voltage were measured by driving the device with [a specific method / tool]. Furthermore, each organic electroluminescent element was driven to a current density of 12.6 mA / cm². 2 The device was driven, and the time (LT95) until the luminescence intensity reached 95% of the initial level was measured. The measurement results are shown in Table 4. In Table 4, EQE and LT95 are shown as relative values ​​with LT95 of EL element 9 set to 1, and the drive voltage is shown as a relative value with EL element 9 as the reference (0). The measurement results show that even when using a different delayed fluorescence material than in Example 1, devices using the compound represented by general formula (1) as the electron barrier material all exhibit high luminescence efficiency, low drive voltage, and long device lifetime.

[0256] [Table 4]

[0257] (Example 4) On a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm has been formed, the following thin films were deposited by vacuum deposition at a vacuum of 5.0 × 10⁻⁶. -5 Organic electroluminescent elements were fabricated by stacking layers of Pa. First, HAT-CN was formed to a thickness of 60 nm on ITO, followed by TrsPCz to a thickness of 30 nm, and then PYD2Cz to a thickness of 5 nm. Next, a host material (reference compound a) and a delayed fluorescence material (T3) were co-deposited from different deposition sources to form a 30 nm thick layer which served as the light-emitting layer. At this time, the host material content was 70 mass%, and the delayed fluorescence material content was 30 mass%. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different deposition sources to form a 30 nm thick layer. The Liq and SF3-TRZ content in this layer was 30 mass% and 70 mass%, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode, thereby fabricating an organic electroluminescent element. This element was designated as reference EL element 1. The fabricated organic electroluminescent element was measured at 2 mA / cm². 2 When driven by this system, the external quantum efficiency (EQE) was measured and showed a high value of 21.9%. This indicates that reference compound a is an excellent host material. On the other hand, an organic electroluminescent element fabricated using the same procedure as before, with the only change being the use of compound 1a instead of PYD2Cz, was designated as reference EL element 2. The fabricated organic electroluminescent element was set to 2 mA / cm². 2 When driven by this, the external quantum efficiency (EQE) was measured and it decreased to 17.1%. Therefore, it was found that reference compound a is not suitable as an electron barrier material. These results indicate that even useful host materials may not be useful as electron barrier materials, suggesting that finding useful electron barrier materials is not easy. [ka] [Industrial applicability]

[0258] Compounds represented by general formula (1) are useful as electron barrier materials and can be used in organic semiconductor devices. Using the compound of the present invention in the electron barrier layer of an organic electroluminescent device can extend the device's lifespan. Therefore, the present invention has high industrial applicability.

Claims

1. An electron barrier material comprising a compound represented by the following general formula (1), and for use in combination with a compound represented by the following general formula (G). 【Chemistry 1】 [wherein, 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 formed by combining two or more thereof. 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 formed by combining two or more thereof. R １ to R ５ do not combine with other R １ to R ５ or Ar to form a cyclic structure, but adjacent R ３ may combine with each other to form a benzofuro skeleton or a benzothieno skeleton. n1, n3, 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 formed by combining two or more thereof. The dibenzofuran in the general formula (1) is bonded to Ar at the 2-position.] General formula (G) 【Chemistry 2】 [In general formula (G), X1 is a nitrogen atom and X2 is a boron atom. R1 to R16, R19 to R26, A1, and A2 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 may be bonded to each other to form a ring structure. R17 and R18 are bonded to each other, forming a single bond and creating a pyrrole ring.

2. The electron barrier material according to claim 1, wherein the compound represented by the general formula (1) has a structure represented by the following general formula (2B). 【Transformation 3】 [In the formula, R １ , R ２ , R ４ , R ５ and R ６ Each of these independently represents one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. ３ R represents one atom or group, or a combination of two or more, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups having 6 to 10 carbon atoms. １ ~R ６ This is the other R １ ~R ６ Although it does not combine with adjacent R to form a ring structure, ３ These elements may combine with each other to form a benzoflo or benzothieno skeleton. n1, n3, and n5 each independently represent an integer from 0 to 4, n2 and n6 each independently represent an integer from 0 to 3, and n4 represents an integer from 0 to 2. X represents an oxygen atom or a sulfur atom.

3. The electron barrier material according to claim 1, wherein the compound represented by the general formula (1) has a structure represented by the following general formula (3). 【Chemistry 4】 [In the formula, R １ , R ２ , R ４ , R ５ and R ６ Each of these independently represents one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. ３ R represents one atom or group, or a combination of two or more, selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups having 6 to 10 carbon atoms. １ ~R ６ This is the other R １ ~R ６ Although it does not combine with adjacent R to form a ring structure, ３ These elements may combine with each other to form a benzoflo or benzothieno skeleton. n1, n3, and n5 each independently represent an integer from 0 to 4, n2 and n6 each independently represent an integer from 0 to 3, and n4 represents an integer from 0 to 2. However, n1 + n3 + n4 + n5 is greater than or equal to 1. R １ and R ３ ~R ５ One or two of these 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. In general formula (3), dibenzofuran is at position 2, (R ６ ) n6 bonds to the benzene ring to which it is attached.

4. The electron barrier material according to claim 2, wherein n1, n2, and n6 in the general formula (2B) are 0.

5. The electron barrier material according to claim 1, wherein n3 to n5 in the general formula (1) are each independently 0 or 1.

6. The electron barrier material according to claim 1, wherein the compound represented by general formula (1) has any of the following structures. 【Transformation 5】

7. An organic semiconductor device comprising an electron barrier material according to any one of claims 1 to 6, The organic semiconductor element is an organic electroluminescent element having an anode, a cathode, and at least two organic layers, the anode and the cathode comprising an electron barrier layer containing the electron barrier material and an emissive layer, wherein the emissive layer contains a compound represented by the following general formula (G). General formula (G) 【Transformation 6】 [In general formula (G), X1 is a nitrogen atom and X2 is a boron atom. R1 to R16, R19 to R26, A1, and A2 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 may be bonded to each other to form a ring structure. R17 and R18 are bonded to each other, forming a single bond and creating a pyrrole ring.

8. The organic semiconductor device according to claim 7, wherein the light-emitting layer comprises a host material and a delayed fluorescence material.

9. The organic semiconductor device according to claim 7, wherein the light-emitting layer includes a host material, a delayed fluorescence material, and a fluorescent light-emitting material comprising a compound represented by the general formula (G), and the amount of light emitted from the fluorescent light-emitting material is the largest amount of light emitted from the device.

10. The organic semiconductor element according to claim 7, wherein the light-emitting layer is adjacent to the electron barrier layer.

11. The organic semiconductor device according to claim 7, wherein the light-emitting layer contains a compound represented by the following general formula (4). 【Transformation 7】 [In 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 them represents a group represented by the following general formula (6), R ２１ ~R ２５ The remainder represents a hydrogen atom or a substituent (however, the substituent referred to here is not a cyano group, a group represented by general formula (5) below, or a group represented by general formula (6) below). 【Transformation 8】 [In general formula (5), L １ represents a single bond or a divalent linking group, R ３１ and R ３２ Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position. 【Chemistry 9】 [In general formula (6), L ２ represents a single bond or a divalent linking group, R ３３ and R ３４ Each of the symbols represents an independent hydrogen atom or substituent, and * represents a bond position.

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