Organic light-emitting elements and films

Abstract

Organic light-emitting elements comprising compounds represented by the following general formulas exhibit excellent light-emitting properties. 1. X In 2, one is N and the other is B; R 1~R 26. A 1. A 2 is H, D, or a substituent; X 11 represents O, S, etc.; A 11. A 12 represents benzene rings, furan rings, etc.; R 111~R 115 represents H, D, aryl, etc.; n represents 3 or 4; L represents single bond, extended aryl, etc.

Description

Technical Field

[0001] This invention relates to an organic light-emitting element and film with good light-emitting properties. Prior Technology

[0002] Research is underway to improve the luminous efficiency of organic light-emitting devices such as organic light-emitting diodes (OLEDs). For example, Non-Patent Document 1 describes the following: By using a compound exhibiting multiple resonance effects, such as 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (5,9-diphenyl-5H,9H-[1,4]benzozaborane[2,3,4-kl]dibenzozaborane) (DABNA-1), thermally active delayed fluorescence is achieved due to the reverse intersystem crossing process, thereby realizing luminescence with a narrow half-value width and high color purity. This luminescence achieves high luminous efficiency and is therefore useful for applications in displays. Furthermore, Non-Patent Literature 1 and Non-Patent Literature 2 describe how modifying DABNA-1 adjusts the energy levels of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and promotes fluorescence radiation processes or inverse intersystem crossing processes that facilitate luminescence, thereby improving the quantum efficiency of electroluminescence.

[0003] [Non-Patent Literature 1] Adv. Mater. 2016, 28, 2777-2781 [Non-Patent Literature 2] Angew. Chem. Int. Ed. 2018, 57, 11316-11320 Summary of the Invention

[0004] Various studies have been conducted on compounds exhibiting such multiple resonance effects, but many aspects regarding the relationship between their structure and luminescence properties remain unknown. To fabricate practical light-emitting elements, a material with at least excellent luminescence properties is needed. Furthermore, it is desirable not only to provide a material with excellent luminescence properties, but also to provide organic light-emitting elements with even better luminescence properties by selecting materials for use in combination with it. Therefore, the inventors have diligently explored ways to develop derivatives of compounds that exhibit multiple resonance effects and to provide organic light-emitting elements with superior luminescence properties by selecting materials for use in combination with them.

[0005] Through painstaking research, the inventors discovered that compounds exhibiting multiple resonance effects possess superior luminescence properties due to their specific structures. Furthermore, they found that these superior luminescence properties are further enhanced when used in combination with materials possessing specific structures. This invention is based on these insights and has the following structure.

[0006] [1] An organic light-emitting element comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2). General formula (1) [Chemical Formula 1] In general formula (1), one of X1 and X2 is a nitrogen atom and the other is a boron atom. R1~R26, A1, and A2 independently represent hydrogen atoms, deuterium atoms, or substituents, respectively. 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, R16 and R17, R17 and R18, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, R25 and R26 can bond to each other to form a ring structure. Where X1 is a nitrogen atom, R17 and R18 bond to each other to form a single bond to form a pyrrole ring; where X2 is a nitrogen atom, R21 and R22 bond to each other to form a single bond to form a pyrrole ring. Where X1 is a nitrogen atom, R7 and R8, and R21 and R22 bond to each other via nitrogen atom to form a 6-membered ring, and R17 and R18 bond to each other to form a single bond, at least one of R1 to R6 is a substituted or unsubstituted aryl group, or any one of R1 and R2, R2 and R3, R3 and R4, R4 and R5, or R5 and R6 bonds to each other to form an aromatic ring or a heteroaromatic ring. General formula (2) [Chemical Formula 2] In general formula (2), X 11 represents O, S, N (RA) or C (RB) (RC). A 11 and A 12 are independently benzene rings, furan rings, thiols, pyrrole rings or cyclopentadiene rings, which may be further condensed with other rings or may be substituted. R 111~R 114, RB, RC independently represent hydrogen atoms, deuterium atoms, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups or cyano groups, respectively. R 115 independently represents hydrogen atoms, deuterium atoms, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups, cyano groups or bonds with L. RA represents substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups or bonds with L. R 111 and R 112, R 112 and R 113, R 113 and R 114, two adjacent R 115, RB and RC can be bonded to each other to form a cyclic structure. n represents any integer from 3 to 4. L represents a single bond, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a linking group formed by two or more of these bonds. Wherein, when X 11 is N and L is bonded to N, at least one of R 115 or at least one of the groups bonded to the ring represented by A 12 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. [2] The organic light-emitting element as described in [1], wherein R3 and R6 in general formula (1) are both substituents. [3] The organic light-emitting element as described in [1] or [2], wherein R8 and R12 of general formula (1) are substituents. In particular, R8 and R12 are alkyl groups with 2 or more carbon atoms, preferably alkyl groups with 3 or more carbon atoms, more preferably alkyl groups with 3 to 8 carbon atoms, and even more preferably alkyl groups with 3 or 4 carbon atoms. [4] An organic light-emitting element as described in any one of [1] to [3], wherein X1 of the general formula (1) is a nitrogen atom and X2 is a boron atom. [5] An organic light-emitting element as described in any one of [1] to [4], wherein R7 and R8, R17 and R18 of general formula (1) are bonded to each other to form -B(R32)-, and R32 independently represents a hydrogen atom, a deuterium atom or a substituent. [6] An organic light-emitting element as described in any one of [1] to [4], wherein R7 and R8, R17 and R18 of general formula (1) are bonded to each other to form -CO-. [7] An organic light-emitting element as described in any one of [1] to [4], wherein R7 and R8, R17 and R18 of general formula (1) are bonded to each other to form -CS-. [8] An organic light-emitting element as described in any one of [1] to [4], wherein R7 and R8, R17 and R18 of general formula (1) are bonded to each other to form -N(R27)-, and R27 independently represents a hydrogen atom, a deuterium atom or a substituent. [9] An organic light-emitting element as described in any one of [1] to [8], wherein groups 1 to 6 of general formula (1) are bonded to each other to form a benzofuran ring or a benzothiophene ring.

[10] An organic light-emitting element as described in any one of [1] to [9], wherein the compound represented by general formula (1) has a rotationally symmetric structure.

[11] An organic light-emitting element as described in [1], wherein the compound represented by general formula (1) has any one of the following structures. For example, a compound may be selected from a group of nine compounds, excluding the compound on the left of the top paragraph. [Chemical Formula 3]

[12] An organic light-emitting element as described in any one of [1] to

[11] , wherein the group of general formula (2) bonded to the right side of L comprises a dibenzofuran structure.

[13] An organic light-emitting element as described in any of [1] to

[12] , wherein L in general formula (2) is methylphenyl.

[14] An organic light-emitting element as described in any of [1] to

[13] , wherein the dipole moment of the compound represented by general formula (2) is less than 2.52.

[15] A membrane comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2). General formula (1) [Chemical Formula 4] In general formula (1), one of X1 and X2 is a nitrogen atom and the other is a boron atom. R1~R26, A1, and A2 independently represent hydrogen atoms, deuterium atoms, or substituents, respectively. 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, R16 and R17, R17 and R18, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, R25 and R26 can bond to each other to form a ring structure. Where X1 is a nitrogen atom, R17 and R18 bond to each other to form a single bond to form a pyrrole ring; where X2 is a nitrogen atom, R21 and R22 bond to each other to form a single bond to form a pyrrole ring. Where X1 is a nitrogen atom, R7 and R8, and R21 and R22 bond to each other via nitrogen atom to form a 6-membered ring, and R17 and R18 bond to each other to form a single bond, at least one of R1 to R6 is a substituted or unsubstituted aryl group, or any one of R1 and R2, R2 and R3, R3 and R4, R4 and R5, or R5 and R6 bonds to each other to form an aromatic ring or a heteroaromatic ring. General formula (2) [Chemical Formula 5] In general formula (2), X represents O, S, N (RA) or C (RB) (RC). A1 and A2 are independently benzene rings, furan rings, thiols, pyrrole rings or cyclopentadiene rings, which may be further condensed with other rings or substituted. R111~R115, RB, RC independently represent hydrogen atoms, deuterium atoms, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups or cyano groups, respectively. RA represents substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups or substituted or unsubstituted alkyl groups. R111 and R112, R112 and R113, R113 and R114, two adjacent R115, RB and RC can be bonded to each other to form a cyclic structure. n represents any integer from 3 or 4. L represents a single bond, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a linking group formed by two or more of these bonds. Wherein, when X is N and L is bonded to N, at least one of R 115 or at least one of the groups bonded to the ring represented by A 2 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group.

[16] The membrane as described in

[15] , wherein the content of the compound represented by the aforementioned general formula (1) is less than that of the compound represented by the aforementioned general formula (2). [Invention Effects]

[0007] In the film of the present invention, the luminescent material exhibits excellent orientation and can be preferably used in organic light-emitting elements. Furthermore, the organic light-emitting element of the present invention exhibits excellent light-emitting characteristics. In particular, the organic light-emitting element of the present invention has high luminous efficiency and low driving voltage, thus it is superior. Implementation

[0008] The present invention will be described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. Furthermore, in this specification, the numerical range indicated by "~" represents the range of values ​​described before and after "~" as lower and upper limits. Also, some or all of the hydrogen atoms present in the molecules of the compounds used in the present invention can be replaced by deuterium atoms (2H, deuteriumD). In the chemical structural formulas of this specification, hydrogen atoms are represented by H or their representation is omitted. For example, when the atom representing a carbon atom bonded to the ring skeleton of the benzene ring is omitted, it is assumed that H forms a carbon atom bond with the ring skeleton at the omitted position. In this specification, the term "substituent" refers to an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" indicates that hydrogen atoms can be substituted by deuterium atoms or substituents.

[0009] [Compounds represented by general formula (1)] The compounds represented by the following general formula (1) will be described. General formula (1) [Chemical Formula 6]

[0010] In general formula (1), one of X1 and X2 is a nitrogen atom, and the other is a boron atom. In one embodiment of the present invention, X1 is a nitrogen atom and X2 is a boron atom. In this case, R17 and R18 are bonded to each other to form a single bond to form a pyrrole ring. In another embodiment of the present invention, X1 is a boron atom and X2 is a nitrogen atom. In this case, R21 and R22 are bonded to each other to form a single bond to form a pyrrole ring.

[0011] In general formula (1), R1~R26, A1, and A2 independently represent hydrogen atoms, deuterium atoms, or substituents, respectively. 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, R16 and R17, R17 and R18, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, R25 and R26 can bond to each other to form a ring structure. The ring structure formed by the R7 and R8 bonds contains boron atoms and four carbon atoms as the ring framework. When X1 is a boron atom, the ring structure formed by the R17 and R18 bonds contains boron atoms and four carbon atoms as the ring framework. When X1 is a nitrogen atom, the ring structure is limited to a pyrrole ring. When X2 is a boron atom, the ring structure formed by the R21 and R22 bonds contains boron atoms and four carbon atoms as the ring framework. When X2 is a nitrogen atom, the ring structure is limited to a pyrrole ring. When R7 and R8, R17 and R18, and R21 and R22 are bonded to each other to form a ring structure containing boron atoms, it is preferred that the ring structure is a 5-7 member ring, more preferably a 5 or 6 member ring, and a 6 member ring is even more preferred. When R7 and R8, R17 and R18, and R21 and R22 are bonded to each other, it is preferable that they form single bonds, -O-, -S-, -N(R27)-, -C(R28)(R29)-, -Si(R30)(R31)-, -B(R32)-, -CO-, or -CS-. Forming -O-, -S-, or -N(R27)- is more preferred, and forming -N(R27)- is even more preferred. Here, R27 to R32 independently represent a hydrogen atom, a deuterium atom, or a substituent. As a substituent, any group selected from substituent groups A to E described below can be used, but substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups are preferred, with substituted or unsubstituted aryl groups being particularly preferred for R27. When R27-R32 are substituents, R27-R32 in the ring formed by R7 and R8 bonded to each other can bond with at least one of R6 and R9 to further form a ring structure; R27-R32 in the ring formed by R17 and R18 bonded to each other can bond with at least one of R16 and R19 to further form a ring structure; R27-R32 in the ring formed by R21 and R22 bonded to each other can bond with at least one of R20 and R23 to further form a ring structure. In one embodiment of the present invention, only one set of R7 and R8, R17 and R18, and R21 and R22 are bonded to each other. In one embodiment of the present invention, only two sets of R7 and R8, R17 and R18, and R21 and R22 are bonded to each other. In another embodiment of the present invention, all of R7 and R8, R17 and R18, and R21 and R22 are bonded to each other.

[0012] The ring structure formed by the bonding of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R16 and R17, R18 and R19, R19 and R20, R20 and R21, R22 and R23, R23 and R24, R24 and R25, R25 and R26 can be aromatic rings or aliphatic rings, and can contain heteroatoms, or can be condensed with other rings with more than one ring. The heteroatoms described herein are preferably selected from the group consisting of nitrogen, oxygen, and sulfur atoms. Examples of the formed cyclic structures include benzene rings, pyridine rings, pyrazine rings, pyrimidine rings, pyrrole rings, imidazole rings, pyrazole rings, triazole rings, imidazoline rings, furan rings, thiophene rings, oxazole rings, isooxazole rings, thiazole rings, isothiazole rings, cyclohexadiene rings, cyclohexene rings, cyclopentene rings, cycloheptanetriene rings, cycloheptadiene rings, cycloheptene rings, and rings formed by further condensation of one or more rings selected from the group consisting of these rings. In a preferred embodiment of the invention, the cyclic structure is a substituted or unsubstituted benzene ring (which may also be condensed with rings), for example, a benzene ring that may be substituted with an alkyl or 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. The number of combinations of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R16 and R17, R18 and R19, R19 and R20, R20 and R21, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 that are bonded to each other to form a ring structure can be 0, or it can be any one of 1 to 6. For example, it can be any one of 1 to 4, and 1, 2, 3, or 4 can be selected. In one embodiment of the present invention, a ring structure is formed by bonding one group selected from R1 and R2, R2 and R3, and R3 and R4 together. In another embodiment of the present invention, R5 and R6 are bonded together to form a ring structure. In another embodiment of the present invention, a ring structure is formed by bonding one group selected from R9 and R10, R10 and R11, and R11 and R12 together. In another embodiment of the present invention, R1 and R2, and R13 and R14 are all bonded together to form a ring structure.In one embodiment of the present invention, one group selected from R1 and R2, R2 and R3, and R3 and R4 are bonded together to form a ring structure, and further, R5 and R6 are bonded together to form a ring structure. In another embodiment of the present invention, R5 and R6, and R19 and R20 are all bonded together to form a ring structure.

[0013] R1 to R26, which are not bonded to adjacent Rn (n=1~26), are hydrogen atoms, deuterium atoms, or substituents. As substituents, any group selected from substituent groups A to E described below can be used. Preferred substituents for R1 to R26 can be substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. For example, the substituent can be a substituted or unsubstituted aryl, or a substituted or unsubstituted alkyl. The alkyl, aryl, and heteroaryl substituents described herein can also be groups selected from any of the substituent groups A to E, but preferably one or more groups selected from the group comprising alkyl, aryl, and heteroaryl, more preferably groups from substituent group E, and can also be unsubstituted. In a preferred embodiment of the invention, at least one of R1 to R6 is a substituent, preferably a group from substituent group E. For example, at least one of R2 to R6 is a substituent, preferably a group from substituent group E. For example, at least one of R5 and R6 is a substituent, preferably a group from substituent group E. In a preferred embodiment of the present invention, at least one of R3 and R6 is a substituent, more preferably both are substituents, and preferably a group belonging to substituent group E. In a preferred embodiment of the present invention, when X1 is a nitrogen atom, at least one of R15 and R20 is a substituent, more preferably both are substituents, and preferably a group belonging to substituent group E. In this case, R17 and R18 are bonded to each other to form a single bond. In a preferred embodiment of the present invention, when X2 is a nitrogen atom, at least one of R19 and R24 is a substituent, more preferably both are substituents, and preferably a group belonging to substituent group E. In this case, R21 and R22 are bonded to each other to form a single bond. In a embodiment of the present invention, at least one of R8 and R12 is a substituent, more preferably both are substituents. In a embodiment of the present invention, R8, R10, and R12 are substituents. As substituents for R8 to R12, unsubstituted alkyl groups are preferred. In particular, when R8 and R12 are alkyl groups having 2 or more carbon atoms (preferably alkyl groups having 3 or more carbon atoms, more preferably alkyl groups having 3 to 8 carbon atoms, and even more preferably alkyl groups having 3 or 4 carbon atoms), the orientation is higher during film formation, which is therefore preferred. Specifically, it is particularly preferred when R8 and R12 are substituents (preferably alkyl groups, more preferably alkyl groups having 2 or more carbon atoms, even more preferably alkyl groups having 3 or more carbon atoms, even more preferably alkyl groups having 3 to 8 carbon atoms, and especially preferably alkyl groups having 3 or 4 carbon atoms) and at least one of R1 to R6 is a substituent (preferably a group belonging to substituent group E). When X1 is a boron atom, at least one of R13 and R17 is a substituent, preferably both. In one embodiment of the present invention, when X1 is a boron atom, R13, R15, and R17 are substituents. When X1 is a boron atom, an unsubstituted alkyl group is preferred as a substituent for R13 to R17. When X2 is a boron atom, at least one of R22 and R26 is a substituent, preferably both.In one embodiment of the present invention, when X2 is a boron atom, R22, R24, and R26 are substituents. When X2 is a boron atom, unsubstituted alkyl groups are preferred as substituents of R22 to R26. Specific examples of groups bonded to boron atoms represented as B in general formula (1) or boron atoms represented as X1 or X2 are given below. The groups bonded to boron atoms that can be used in the present invention are not to be interpreted as limitingly specific in the following examples. Furthermore, in this specification, the CH3 designation is omitted for methyl groups. * indicates the bonding position. [Chemical Formula 7]

[0014] Specific examples of R1 to R26 in general formula (1) are given below. R13 to R21 when X1 is a nitrogen atom, R18 to R26 when X2 is a nitrogen atom, and Z1 to Z9 are preferred. R22 to R26 when X1 is a nitrogen atom, and R13 to R17 when X2 is a nitrogen atom, and Z1 to Z7 are preferred. The groups that can be bonded to boron atoms in this invention are not limited to the following specific examples. D represents a deuterium atom. * indicates the bonding position. [Chemical Formula 8]

[0015] A1 and A2 are hydrogen atoms, deuterium atoms, or substituents. As substituents, any group selected from the substituent group A to E described below can be used. In a preferred embodiment of the present invention, A1 and A2 are each independently a hydrogen atom or a deuterium atom. For example, A1 and A2 are hydrogen atoms. For example, A1 and A2 are deuterium atoms. One of A1 and A2 can be a substituent. Furthermore, A1 and A2 can each be a substituent independently. The preferred substituents for A1 and A2 are acceptor groups. The acceptor group is a group with a positive Hammett σp value. Here, "Hammett's σp value" is proposed by LP Hammett and quantifies the effect of the substituent on the reaction rate or equilibrium of the para-substituted benzene derivative. Specifically, it is the following equation that holds between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k 0)=ρσp or log(K / K0)=ρσp The constant (σp) is specific to the substituents. In the above formula, k0 represents the rate constant of the unsubstituent benzene derivative, k represents the rate constant of the substituent-substituted benzene derivative, K0 represents the equilibrium constant of the unsubstituent benzene derivative, K represents the equilibrium constant of the substituent-substituted benzene derivative, and ρ represents the reaction constant determined by the type and conditions of the reaction. For explanations related to the "Hammett's σp value" in this invention and the values ​​of each substituent, refer to the records related to the σp values ​​in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). The acceptor groups that can be used in A1 and A2 are preferably groups 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 at least substituted with a cyano group, groups containing a fluorine atom, and substituted or unsubstituted heteroaryl groups containing a nitrogen atom as a ring skeleton constituent atom. The aryl group at least substituted with a cyano group described herein may be substituted with a substituent other than a cyano group (e.g., alkyl or aryl), but may also be an aryl group substituted only with a cyano group. It is preferred that the aryl group at least substituted with a cyano group be a phenyl group at least substituted with a cyano group. It is preferred that the cyano group has one or two substitutions, for example, one or two. Examples of groups containing a fluorine atom include fluorine atoms, fluorinated alkyl groups, fluorine atoms, or aryl groups at least substituted with a fluorinated alkyl group. It is preferred that the fluorinated alkyl group be a perfluoroalkyl group, and preferably have 1 to 6 carbon atoms, with 1 to 3 being more preferred. Furthermore, the heteroaryl group containing a nitrogen atom as a ring skeleton can be a monocyclic ring or a condensed ring formed by the condensation of two or more rings. In the case of a condensed ring, the number of rings after condensation is preferably 2 to 6, for example, 2 to 4 or two. Specific examples of the ring constituting the heteroaryl group include pyridine rings, pyrimidine rings, pyridine rings, triphenylamine rings, quinoline rings, isoquinoline rings, quinazoline rings, quinoline rings, and naringin rings other than quinazoline and quinoline rings. The ring constituting the heteroaryl group can be substituted with a deuterium atom or a substituent. Examples of substituents include groups selected from the group consisting of alkyl, aryl, and heteroaryl groups, or groups formed by combinations of two or more groups. A cyano group is particularly preferred as the acceptor group that can be used for A1 and A2. In one embodiment of the present invention, at least one of A1 and A2 is an acceptor group. In one embodiment of the present invention, only one of A1 and A2 is an acceptor group. In one embodiment of the present invention, A1 and A2 are the same acceptor group. In one embodiment of the present invention, A1 and A2 are different acceptor groups. In one embodiment of the present invention, A1 and A2 are cyano groups. In one embodiment of the present invention, A1 and A2 are halogen atoms, such as bromine atoms.

[0016] The following examples illustrate specific examples of acceptor groups that can be used in this invention. However, the acceptor groups that can be used in this invention are not to be interpreted as limiting by the following examples. In this specification, the methyl group is omitted from the CH3 designation. Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups. Also, "D" indicates a deuterium atom. * indicates a bond position. [Chemical Formula 9]

[0017] Furthermore, when X1 is a nitrogen atom, R7 and R8 form a 6-membered ring through nitrogen atom bonding, R21 and R22 form a 6-membered ring through nitrogen atom bonding, and R17 and R18 form a single bond with each other, at least one of R1 to R6 is a substituted or unsubstituted aryl group, or any one of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6 forms an aromatic ring (a condensable substituted or unsubstituted benzene ring) or a heteroaromatic ring (preferably a condensable substituted or unsubstituted benzofuran furan ring, or a condensable substituted or unsubstituted benzothiophene thiophene thiophene ring). Furthermore, when X1 is a boron atom, X2 is a nitrogen atom, and R7 and R8, R17 and R18 are bonded together to form a ring structure containing a boron atom, this ring structure is a 5- to 7-membered ring. In the case of a 6-membered ring, R7 and R8, R17 and R18 are bonded together to form -B(R32)-, -CO-, -CS-, or -N(R27)-. It is preferable that R27 represents a hydrogen atom, a deuterium atom, or a substituent.

[0018] When X1 in general formula (1) is a nitrogen atom, the compounds of the present invention have the following skeleton (1a). When X2 in general formula (1) is a nitrogen atom, the compounds of the present invention have the following skeleton (1b). [Chemical Formula 10]

[0019] Each hydrogen atom in the skeleton (1a) and (1b) can be replaced with a deuterium atom or a substituent. Furthermore, they can be substituted together with adjacent hydrogen atoms to form a linking group, thus forming a cyclic structure. For details, please refer to the description of R1 to R26, A1, and A2 corresponding to general formula (1). Examples include compounds in which the phenyl groups bonded to boron atoms in the skeleton (1a) and (1b) are substituted with mesityl, 2,6-diisopropylphenyl, or 2,4,6-triisopropylphenyl. In one embodiment of the present invention, each hydrogen atom in the skeleton (1a) and (1b) can form a cyclic structure without being substituted together with adjacent hydrogen atoms to form a linking group.

[0020] As a preferred group of compounds having a skeleton (1a), compounds represented by the following general formula (1a) can be exemplified. General formula (1a) [Chemical Formula 11]

[0021] In general formula (1a), Ar1 to Ar4 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, preferably substituted or unsubstituted aryl groups. R41 and R42 independently represent substituted or unsubstituted alkyl groups, 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. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. It is preferred that at least one of n1 to n4 is 1 or more, and that m1 and m2 are each an integer from 1 to 5. In one state of the present invention, n1 to n4 independently represent integers from 0 to 2. In a preferred state of the present invention, at least one of n1 to n4 is 1 or more, preferably at least one of n1 and n2 is 1 or more, and at least one of n3 and n4 is 1 or more. In one state of the present invention, n1 and n3 are independently 1 or 2, and n2 and n4 are 0. In one state of the present invention, n2 and n4 are independently 1 or 2, and n1 and n3 are 0. In one state of the present invention, n1 to n4 are independently 1 or 2. In one state of the present invention, n1 and n3 are equal, and n2 and n4 are equal. In one state of the present invention, n1 and n3 are 1, and n2 and n4 are 0. In one state of the present invention, n1 and n3 are 0, and n2 and n4 are 1. In one state of the present invention, n1 to n4 are all 1. The bonding positions of Ar1 to Ar4 can be at least one of positions 3 and 6 of the carbazole ring, at least one of positions 2 and 7, at least one of positions 1 and 8, or at least one of positions 4 and 5. The bonding positions of Ar1 to Ar4 can be both positions 3 and 6 of the carbazole ring, both positions 2 and 7, both positions 1 and 8, or both positions 4 and 5. For example, at least one of positions 3 and 6 can be preferred, or even more preferably both positions 3 and 6. In a preferred embodiment of the present invention, Ar1 to Ar4 are all the same group. In a preferred embodiment of the present invention, Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl or naphthyl group, and even more preferably a substituted or unsubstituted phenyl group. As a substituent, any group selected from the substituent group A to E described below can be mentioned, but an unsubstituted phenyl group is also preferred. Preferred examples of Ar 1 to Ar 4 include phenyl, ortho-phenyl, meta-phenyl, para-phenyl, and triphenyl. In one embodiment of the present invention, m1 and m2 are each independently 0. In one embodiment of the present invention, m1 and m2 are each independently any integer from 1 to 5. In one embodiment of the present invention, m1 and m2 are equal. In one embodiment of the present invention, R41 and R42 are alkyl groups having 1 to 6 carbon atoms, for example, alkyl groups having 1 to 3 carbon atoms can be selected, or methyl can be selected. Regarding the substitution position of the alkyl group, the carbon atom bonded to the boron atom can be set to position 1, examples include only position 2, only position 3, only position 4, positions 3 and 5, positions 2 and 4, positions 2 and 6, positions 2 and 4 and 6, etc., at least position 2 is preferred, and at least positions 2 and 6 are more preferred. For explanations and preferred ranges of A1 and A2, please refer to the corresponding records of general formula (1).

[0022] Specific examples of compounds represented by general formula (1a) are given below. The compounds of general formula (1a) that can be used in this invention are not to be limited by the specific examples given below. For example, as a preferred group, the group consisting of compounds other than those in the middle of column 4 and column 8 below can be given. [Chemical Formula 12]

[0023] Hereinafter, another set of specific examples of compounds represented by general formula (1a) are given. The compounds of general formula (1a) that can be used in this invention are not to be interpreted as limiting by the following set of specific examples. [Chemical Formula 13]

[0024] As a preferred group of compounds having a skeleton (1b), compounds represented by the following general formula (1b) can be exemplified. General formula (1b) [Chemical Formula 14]

[0025] In general formula (1b), Ar5 to Ar8 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. R43 and R44 independently represent substituted or unsubstituted alkyl groups. 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. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. For details regarding Ar5 to Ar8, R43 and R44, m3 and m4, n5 to n8, A1, and A2, refer to the descriptions of Ar1 to Ar4, R41 and R42, m1 and m2, n1 to n4, A1, and A2 in general formula (1a). It is preferable that at least one of n5 to n8 is 1 or higher, and m3 and m4 are each an independent integer from 1 to 5.

[0026] Specific examples of compounds represented by general formula (1b) are given below. The compounds of general formula (1b) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 15]

[0027] When R7 and R8 of general formula (1) are bonded to each other to form N-Ph, when X1 is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (2a), and when X2 is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (2b). Ph is phenyl. Skeleton (2a) [Chemical Formula 16]

[0028] Each hydrogen atom in the skeleton (2a) and (2b) can be replaced with a deuterium atom or a substituent. Furthermore, they can be replaced together with adjacent hydrogen atoms to form a linking group, thus forming a cyclic structure. For details, please refer to the description of R1 to R26, A1, and A2 corresponding to general formula (1). At least one hydrogen atom in the benzene ring constituting the carbazole moiety contained in the skeleton (2a) is replaced by a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeleton (2a) and (2b) can form a cyclic structure without being replaced together with adjacent hydrogen atoms to form a linking group.

[0029] As a preferred group of compounds having a skeleton (2a), compounds represented by the following general formula (2a) can be exemplified. General formula (2a) [Chemical Formula 17]

[0030] In general formula (2a), Ar9 to Ar14 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n9, n11, n12, and n14 independently represent integers from 0 to 4, and n10 and n13 independently represent integers from 0 to 2. At least one of n9, n10, n12, and n13 is 1 or more. A1 and A2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n9 to n14 each independently represent an integer from 0 to 2. In one embodiment of the present invention, at least one of n9 to n14 is 1 or more; for example, n9 and n12 can be set to 1 or more, or n10 and n13 can be set to 1 or more. In a preferred embodiment of the present invention, at least one of n9, n10, n12, and n13 is 1 or more. In one embodiment of the present invention, n9 and n12 are each independently 1 or 2, and n10, n11, n13, and n14 are 0. In one embodiment of the present invention, n10 and n13 are each independently 1 or 2, and n9, n11, n12, and n14 are 0. In one embodiment of the present invention, n9 and n12 are each independently 1 or 2, n10 and n13 are each independently 1 or 2, and n11 and n14 are 0. In one embodiment of the present invention, n9 to n14 are all 1. The bonding positions of Ar 9 to Ar 14 can be set at positions 3 and 6 of the carbazole ring, or at other positions. In a preferred embodiment of the present invention, Ar 9 to Ar 14 are all the same functional group. For the preferred functional groups of Ar 9 to Ar 14, please refer to the description of the corresponding Ar 1 to Ar 4. For the description and preferred scope of A 1 and A 2, please refer to the description of the corresponding general formula (1).

[0031] Specific examples of compounds represented by general formula (2a) are given below. The compounds of general formula (2a) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 18]

[0032] As a preferred group of compounds having a skeleton (2b), compounds represented by the following general formula (2b) can be exemplified. General formula (2b) [Chemical Formula 19]

[0033] In general formula (2b), Ar 15 to Ar 20 independently represent substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n15, n17, n18, and n20 independently represent integers from 0 to 4, and n16 and n19 independently represent integers from 0 to 2. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. For details regarding Ar 15 to Ar 20, n15 to n20, A1, and A2, refer sequentially to the descriptions of Ar 9 to Ar 14, n9 to n14, A1, and A2 in general formula (2a).

[0034] Specific examples of compounds represented by general formula (2b) are given below. The compounds of general formula (2b) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 20]

[0035] When R7 and R8 in general formula (1) are bonded to each other to form a single bond, when X1 is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (3a), and when X2 is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (3b). [Chemical Formula 21]

[0036] Each hydrogen atom in the framework (3a) and (3b) can be replaced with a deuterium atom or a substituent. Furthermore, they can be replaced together with adjacent hydrogen atoms to form a linking group, thus forming a ring structure. For details, please refer to the description of R1 to R26, A1, and A2 corresponding to general formula (1). In one embodiment of the present invention, each hydrogen atom in the framework (3a) and (3b) can form a ring structure without being replaced together with adjacent hydrogen atoms to form a linking group.

[0037] As a preferred group of compounds having a skeleton (3a), compounds represented by the following general formula (3a) can be exemplified. General formula (3a) [Chemical Formula 22]

[0038] In general formula (3a), Ar 21 to Ar 26 independently represent substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n21, n23, n24, and n26 independently represent integers from 0 to 4, and n22 and n25 independently represent integers from 0 to 2. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. For details regarding Ar 21 to Ar 25 and n21 to n25, refer to the descriptions of Ar 9 to Ar 14, n9 to n14, A1, and A2 in general formula (2a).

[0039] Specific examples of compounds represented by general formula (3a) are given below. The compounds of general formula (3a) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 23]

[0040] As a preferred group of compounds having a skeleton (3b), compounds represented by the following general formula (3b) can be exemplified. General formula (3b) [Chemical Formula 24]

[0041] In general formula (3b), Ar 27 to Ar 32 independently represent substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n27, n29, n30, and n32 independently represent integers from 0 to 4, and n28 and n31 independently represent integers from 0 to 2. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. For details regarding Ar 27 to Ar 32, n27 to n32, A1, and A2, refer sequentially to the descriptions of Ar 15 to Ar 20, n15 to n20, A1, and A2 in general formula (2b).

[0042] Specific examples of compounds represented by general formula (3b) are given below. The compounds of general formula (3b) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 25]

[0043] In a preferred embodiment of the present invention, compounds comprising the two benzene rings constituting the carbazole moiety in general formula (1) that are condensed with other rings are selected. Particularly preferred are compounds condensed with benzofuran rings, compounds condensed with benzothiophene rings, and compounds condensed with benzene rings. Specific examples of such cyclocondensed compounds are described below.

[0044] Examples of such compounds include those in general formula (1) that are formed by the condensation of benzene rings in which the boron atoms of the two benzene rings constituting the carbazole moiety are not directly bonded with each other, and benzofuran or benzothiophene rings. Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b). [Chemical Formula 26]

[0045] In the skeletons (4a) and (4b), Y1 to Y4 independently represent two hydrogen atoms, a single bond, or N(R 27). The two hydrogen atoms referred to here indicate a state where the two benzene rings bonded to the boron atom are not connected to each other. It is preferred that Y1 and Y2 are the same and Y3 and Y4 are the same, but they can also be different. In one embodiment of the present invention, Y1 to Y4 are single bonds. In another embodiment of the present invention, Y1 to Y4 are N(R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z1 to Z4 independently represent oxygen atoms or sulfur atoms. It is preferred that Z1 and Z2 are the same and Z3 and Z4 are the same, but they can also be different. In one embodiment of the present invention, Z1 to Z4 are oxygen atoms. In this case, the furan ring of benzofuran condenses with the benzene ring constituting the carbazole moiety in (4a) and (4b). The orientation of the condensed furan ring is not limited. In one embodiment of the present invention, Z1 to Z4 are sulfur atoms. In this case, the thiophene ring of benzothiophene condenses with the benzene ring constituting the carbazole moiety in (4a) and (4b). The orientation of the condensed thiophene ring is not limited. Each hydrogen atom in the framework (4a) and (4b) can be replaced with a deuterium atom or a substituent. Furthermore, they can be replaced together with adjacent hydrogen atoms to form a linking group, thus forming a ring structure. For details, please refer to the description of R1 to R26, A1, and A2 corresponding to general formula (1). In one embodiment of the present invention, each hydrogen atom in the framework (4a) and (4b) can form a ring structure without being replaced together with adjacent hydrogen atoms to form a linking group.

[0046] As a preferred group of compounds having a skeleton (4a), compounds represented by the following general formula (4a) can be exemplified. In the specific examples, X is an oxygen atom or a sulfur atom, and compounds in which X is an oxygen atom and compounds in which X is a sulfur atom are disclosed, respectively. In the specific examples of compounds represented by the other general formulas below, X also has the same meaning. General formula (4a) [Chemical Formula 27]

[0047] In general formula (4a), Ar 51 and Ar 52 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, preferably substituted or unsubstituted aryl groups. R 51 and R 52 independently represent substituted or unsubstituted alkyl groups. m 51 and m 52 independently represent integers from 0 to 4. n 51 and n 52 independently represent integers from 0 to 2. Y 1 to Y 4 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 1 to Z 4 independently represent an oxygen atom or a sulfur atom. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n51 and n52 are the same number. For example, n51 and n52 can be 0, or n51 and n52 can be 1. In one embodiment of the present invention, m51 and m52 are the same number. In one embodiment of the present invention, m51 and m52 are integers from 0 to 3. For example, m51 and m52 can be 0, m51 and m52 can be 1, m51 and m52 can be 2, or m51 and m52 can be 3. Regarding preferred groups of Ar 51, Ar 52, R 51, R 52, Al, and Al2, refer to the description of the correspondences of Ar 1 to Ar 4, R 41 to R 42, Al, and Al2 in general formula (1a).

[0048] Specific examples of compounds represented by general formula (4a) are given below. The compounds of general formula (4a) that can be used in this invention are not to be limited by the following set of specific examples. Regarding 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 a portion of X atoms in the molecule are oxygen atoms and the remainder are sulfur atoms can also be used. [Chemical Formula 28]

[0049] Hereinafter, another set of specific examples of compounds represented by general formula (4a) are given. The compounds of general formula (4a) that can be used in this invention are not to be interpreted as limiting by the following set of specific examples. [Chemical Formula 29]

[0050] As a preferred group of compounds having a skeleton (4b), compounds represented by the following general formula (4b) can be exemplified. General formula (4b) [Chemical Formula 30]

[0051] In general formula (4b), Ar 53 and Ar 54 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl, for example, preferably substituted or unsubstituted aryl. R 53 and R 54 independently represent substituted or unsubstituted alkyl. m53 and m54 independently represent integers from 0 to 4. n53 and n54 independently represent integers from 0 to 2. Y 3 and Y 4 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 3 and Z 4 independently represent an oxygen atom or a sulfur atom. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. For detailed information on Ar 53, Ar 54, R 53, R 54, m53, m54, n53, n54, A 1, and A 2, please refer to the records of Ar 51, Ar 52, R 51, R 52, m51, m52, n51, n52, A 1, and A 2 in general formula (4a).

[0052] Specific examples of compounds represented by general formula (4b) are given below. The compounds of general formula (4b) that can be used in this invention are not to be limited by the specific examples below. Specific examples involving X are disclosed in 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. Compounds in which a portion of X atoms in the molecule is oxygen atoms and the remainder is sulfur atoms can also be used. [Chemical Formula 31]

[0053] Examples of such compounds include those in general formula (1) that are formed by the condensation of a benzene ring with a benzofuran ring or a benzothiophene ring, where the boron atoms in the two benzene rings constituting the carbazole moiety are directly bonded. Examples of such compounds include compounds having the following skeleton (5a) and compounds having the following skeleton (5b). [Chemical Formula 32]

[0054] In the frameworks (5a) and (5b), Y5 to Y8 independently represent two hydrogen atoms, a single bond, or N (R 27). Z5 to Z8 independently represent an oxygen atom or a sulfur atom. For details regarding Y5 to Y8 and Z5 to Z8, please refer to the corresponding descriptions of the frameworks (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the frameworks (5a) and (5b) may form a ring structure without being substituted together with adjacent hydrogen atoms as a linking group.

[0055] As a preferred group of compounds having a skeleton (5a), compounds represented by the following general formula (5a) can be exemplified. General formula (5a) [Chemical Formula 33]

[0056] In general formula (5a), Ar 55 and Ar 56 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl, for example, preferably substituted or unsubstituted aryl. R 55 and R 56 independently represent substituted or unsubstituted alkyl. m55 and m56 independently represent integers from 0 to 4. n55 and n56 independently represent integers from 0 to 4. Y 5 and Y 6 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 5 and Z 6 independently represent an oxygen atom or a sulfur atom. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n55 and n56 are integers from 0 to 2. For example, n55 and n56 can be 0, or n55 and n56 can be 1. In one embodiment of the present invention, m51 and m52 are the same number. For details regarding m55 and m56, please refer to the description of m51 and m52 in general formula (4a). For preferred groups of Ar 55, Ar 56, R 55, R 56, Al, and Al2, please refer to the description of the corresponding groups of Ar 1, Ar 3, R 41, R 42, Al, and Al2 in general formula (1a).

[0057] Specific examples of compounds represented by general formula (5a) are given below. The compounds of general formula (5a) that can be used in this invention are not to be limited by the following set of specific examples. Regarding 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 a portion of X atoms in the molecule are oxygen atoms and the remainder are sulfur atoms can also be used. [Chemical Formula 34]

[0058] The following provides another set of specific examples of compounds represented by general formula (5a). The compounds of general formula (5a) that can be used in this invention are not to be construed as limiting the scope of the following specific examples. [Chemical Formula 35]

[0059] As a preferred group of compounds having a skeleton (5b), compounds represented by the following general formula (5b) can be exemplified. General formula (5b) [Chemical Formula 36]

[0060] In general formula (5b), Ar 57 and Ar 58 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl, for example, preferably substituted or unsubstituted aryl. R 57 and R 58 independently represent substituted or unsubstituted alkyl. m57 and m58 independently represent integers from 0 to 4. n57 and n58 independently represent integers from 0 to 4. Y 7 and Y 8 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 7 and Z 8 independently represent an oxygen atom or a sulfur atom. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. For details regarding Ar 57, Ar 58, R 57, R 58, m57, m58, n57, n58, A 1, and A 2, please refer to the records of Ar 55, Ar 56, R 55, R 56, m55, m56, n55, n56, A 1, and A 2 in general formula (5a).

[0061] Specific examples of compounds represented by general formula (5b) are given below. The compounds of general formula (5b) that can be used in this invention are not to be limited by the following set of specific examples. Regarding 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 a portion of X atoms in the molecule is oxygen atoms and the remainder is sulfur atoms can also be used. [Chemical Formula 37]

[0062] Hereinafter, another set of specific examples of compounds represented by general formula (5b) are given. The compounds of general formula (5b) that can be used in this invention are not to be interpreted as limiting by the following set of specific examples. [Chemical Formula 38]

[0063] Compounds in which the two benzene rings constituting the carbazole moiety present in general formula (1) are condensed with a benzofuran ring or a benzothiophene ring are preferably exemplified. As examples of such compounds, compounds having the following skeleton (6a) and compounds having the following skeleton (6b) can be shown. [Chemical Formula 39]

[0064] In the frameworks (6a) and (6b), Y9 to Y12 independently represent two hydrogen atoms, a single bond, or N (R 27). Z9 to Z16 independently represent an oxygen atom or a sulfur atom. It is preferred that Z9 to Z16 are the same, but they can also be different. In one embodiment of the present invention, Z9 to Z16 are oxygen atoms. In one embodiment of the present invention, Z9 to Z16 are sulfur atoms. For details regarding Y9 to Y12, please refer to the corresponding descriptions of the frameworks (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the frameworks (6a) and (6b) may not be substituted together with adjacent hydrogen atoms to form a linker and thus form a ring structure.

[0065] As a preferred group of compounds having a skeleton (6a), compounds represented by the following general formula (6a) can be exemplified. General formula (6a) [Chemical Formula 40]

[0066] In general formula (6a), R 59 and R 60 independently represent substituted or unsubstituted alkyl groups, respectively. m59 and m60 independently represent integers from 0 to 4, respectively. Y 9 and Y 10 independently represent two hydrogen atoms, a single bond, or N (R 27), respectively. R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 9 to Z 12 independently represent an oxygen atom or a sulfur atom, respectively. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent, respectively. For detailed information on R 59, R 60, m59, m60, Z 9 to Z 12, A 1, and A 2, please refer to the descriptions of R 55, R 56, m55, m56, A 1, A 2 in general formula (5a) and Z 9 to Z 12 in the skeleton (6a).

[0067] Specific examples of compounds represented by general formula (6a) are given below. The compounds of general formula (6a) that can be used in this invention are not to be limited by the specific examples below. Specific examples involving X are disclosed in 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. Compounds in which a portion of X atoms in the molecule is oxygen atoms and the remainder is sulfur atoms can also be used. [Chemical Formula 41]

[0068] As a preferred group of compounds having a skeleton (6b), compounds represented by the following general formula (6b) can be exemplified. General formula (6b) [Chemical Formula 42]

[0069] In general formula (6b), R 61 and R 62 independently represent substituted or unsubstituted alkyl groups, respectively. m61 and m60 independently represent integers from 0 to 4, respectively. Y 11 and Y 12 independently represent two hydrogen atoms, a single bond, or N (R 27), respectively. R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Z 13 to Z 16 independently represent an oxygen atom or a sulfur atom, respectively. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent, respectively. For details regarding R 61, R 62, m61, m62, Z 13 to Z 16, A 1, and A 2, refer to the descriptions of R 59, R 60, m59, m60, A 1, A 2 in general formula (6a) and Z 13 to Z 16 in the skeleton (6b).

[0070] Specific examples of compounds represented by general formula (6b) are given below. The compounds of general formula (6b) that can be used in this invention are not to be limited by the specific examples below. Specific examples involving X are disclosed in 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. Compounds in which a portion of X atoms in the molecule is oxygen atoms and the remainder is sulfur atoms can also be used. [Chemical Formula 43]

[0071] Examples of such compounds include those in general formula (1) where the boron atoms in the two benzene rings constituting the carbazole moiety are not directly bonded, and compounds that are condensed with benzene rings. Examples of such compounds include compounds having the following skeleton (7a) and compounds having the following skeleton (7b). [Chemical Formula 44]

[0072] In the frameworks (7a) and (7b), Y 21 to Y 24 independently represent two hydrogen atoms, a single bond, or N (R 27). For details regarding Y 21 to Y 24, please refer to the description of Y 1 to Y 4 in the frameworks (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the frameworks (7a) and (7b) may form a ring structure without being substituted together with adjacent hydrogen atoms as a linking group.

[0073] As a preferred group of compounds having a skeleton (7a), compounds represented by the following general formula (7a) can be exemplified. General formula (7a) [Chemical Formula 45]

[0074] In general formula (7a), Ar 71 to Ar 74 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n71 and n73 independently represent integers from 0 to 2. n72 and n74 independently represent integers from 0 to 4. Y 21 and Y 22 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one state of the present invention, n71~n74 are integers from 0 to 2. In one state of the present invention, n71 and n73 are the same number, and n72 and n74 are the same number. n71~n74 can be the same number. For example, n71~n74 can be 0. n71~n74 can all be 1. Furthermore, for example, n71 and n73 can be 0, and n72 and n74 can be 1. For preferred groups of Ar 71 to Ar 74, A 1, A 2, refer to the description of the correspondence of Ar 1 to Ar 4, A 1, A 2 in general formula (1a).

[0075] Specific examples of compounds represented by general formula (7a) are given below. The compounds of general formula (7a) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 46]

[0076] As a preferred group of compounds having a skeleton (7b), compounds represented by the following general formula (7b) can be exemplified. General formula (7b) [Chemical Formula 47]

[0077] In general formula (7b), Ar 75 to Ar 78 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. n75 and n77 independently represent integers from 0 to 2. n76 and n78 independently represent integers from 0 to 4. Y 23 and Y 24 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. For detailed descriptions of n75 to n78, refer sequentially to the descriptions of n71 to n74 in general formula (7a). For preferred groups of Ar 75 to Ar 78, refer to the corresponding descriptions of Ar 1 to Ar 4 in general formula (1a).

[0078] Specific examples of compounds represented by general formula (7b) are given below. The compounds of general formula (7b) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 48]

[0079] Examples of such compounds include those formed by the condensation of benzene rings in which boron atoms are directly bonded in the two benzene rings constituting the carbazole moiety, as described in general formula (1). Examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b). [Chemical Formula 49]

[0080] In the frameworks (8a) and (8b), Y 25 to Y 28 independently represent two hydrogen atoms, a single bond, or N (R 27). For details regarding Y 25 to Y 28, please refer to the corresponding descriptions of the frameworks (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the frameworks (8a) and (8b) may form a ring structure without being substituted together with adjacent hydrogen atoms as a linking group.

[0081] As a preferred group of compounds having a skeleton (8a), compounds represented by the following general formula (8a) can be exemplified. General formula (8a) [Chemical Formula 50]

[0082] In general formula (8a), Ar 79 and Ar 80 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl, for example, substituted or unsubstituted aryl may be preferred. R 71 and R 72 independently represent substituted or unsubstituted alkyl. m71 and m72 independently represent integers from 0 to 4. n79 and n80 independently represent integers from 0 to 4. Y 25 and Y 26 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n79 and n80 are integers from 0 to 2. In one embodiment of the present invention, n79 and n80 are the same number, for example, both can be 0 or both can be 1. In one embodiment of the present invention, m71 and m72 are integers from 0 to 2. In one embodiment of the present invention, m71 and m72 are the same number, for example, both can be 0 or both can be 1. Regarding preferred groups of Ar 79, Ar 80, R 71, R 72, Al, and Al2, refer to the description of the correspondences of Ar 1, Ar 3, R 41, R 42, Al, and Al2 in general formula (1a).

[0083] Specific examples of compounds represented by general formula (8a) are given below. The compounds of general formula (8a) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 51]

[0084] As a preferred group of compounds having a skeleton (8b), compounds represented by the following general formula (8b) can be exemplified. General formula (8b) [Chemical Formula 52]

[0085] In general formula (8b), Ar 81 and Ar 82 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl, for example, substituted or unsubstituted aryl may be preferred. R 73 and R 74 independently represent substituted or unsubstituted alkyl. m73 and m74 independently represent integers from 0 to 4. n81 and n82 independently represent integers from 0 to 4. Y 27 and Y 28 independently represent two hydrogen atoms, a single bond, or N (R 27). R 27 represents a hydrogen atom, a deuterium atom, or a substituent. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent. For detailed descriptions of m73, m74, n81, and n82, please refer to the descriptions of m71, m72, n79, and n80 in general formula (8a). For preferred groups of Ar 81, Ar 82, R 73, R 74, Al, and Al2, please refer to the descriptions of corresponding groups of Ar 1, Ar 3, R 41, R 42, Al, and Al2 in general formula (1a).

[0086] Specific examples of compounds represented by general formula (8b) are given below. The compounds of general formula (8b) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 53]

[0087] Compounds in which the two benzene rings constituting the carbazole moiety present in general formula (1) are condensed with benzene rings can be preferably exemplified. Examples of such compounds include compounds having the following skeleton (9a) and compounds having the following skeleton (9b). [Chemical Formula 54]

[0088] In the frameworks (9a) and (9b), Y 29 to Y 32 independently represent two hydrogen atoms, a single bond, or N (R 27). For details regarding Y 29 to Y 32, please refer to the corresponding descriptions of the frameworks (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the frameworks (9a) and (9b) may form a ring structure without being substituted together with adjacent hydrogen atoms as a linking group.

[0089] As a preferred group of compounds having a skeleton (9a), compounds represented by the following general formula (9a) can be exemplified. General formula (9a) [Chemical Formula 55]

[0090] In general formula (9a), R 75 and R 76 independently represent substituted or unsubstituted alkyl groups, respectively. m75 and m76 independently represent integers from 0 to 4, respectively. Y 29 and Y 30 independently represent two hydrogen atoms, a single bond, or N (R 27), respectively. R 27 represents a hydrogen atom, a deuterium atom, or a substituent. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent, respectively. For detailed information on R 75, R 76, m75, m76, A 1, and A 2, please refer to the description of R 71, R 72, m71, m72, A 1, and A 2 in general formula (8a).

[0091] Specific examples of compounds represented by general formula (9a) are given below. The compounds of general formula (9a) that can be used in this invention are not to be interpreted as limiting the scope of the specific examples given below. [Chemical Formula 56]

[0092] As a preferred group of compounds having a skeleton (9b), compounds represented by the following general formula (9b) can be exemplified. General formula (9b) [Chemical Formula 57]

[0093] In general formula (9b), R 77 and R 78 independently represent substituted or unsubstituted alkyl groups, respectively. m77 and m78 independently represent integers from 0 to 4, respectively. Y 31 and Y 32 independently represent two hydrogen atoms, a single bond, or N (R 27), respectively. R 27 represents a hydrogen atom, a deuterium atom, or a substituent. A 1 and A 2 independently represent a hydrogen atom, a deuterium atom, or a substituent, respectively. For details regarding R 77, R 78, m77, m78, A 1, and A 2, please refer to the description of R 71, R 72, m71, m72, A 1, and A 2 in general formula (8a).

[0094] Specific examples of compounds represented by general formula (9b) are given below. The compounds of general formula (9b) that can be used in this invention are not to be interpreted as limiting by the specific examples below. [Chemical Formula 58]

[0095] As a compound represented by general formula (1), it is preferable to have a compound containing four or more carbazole moieties within the molecule. As an example of such a compound, a compound having the following skeleton (10) can be shown. Skeleton (10) [Chemical Formula 59]

[0096] Each hydrogen atom in the skeleton (10) can be replaced with a deuterium atom or a substituent. Alternatively, it can be replaced together with an adjacent hydrogen atom to form a linking group, thus forming a cyclic structure. For details, refer to the descriptions of R1 to R26, A1, and A2 corresponding to general formula (1). At least one hydrogen atom in the benzene ring constituting the carbazole moiety contained in the skeleton (10) is replaced with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeleton (10) can form a cyclic structure without being replaced together with an adjacent hydrogen atom to form a linking group.

[0097] As a preferred group of compounds having a skeleton (10), compounds represented by the following general formula (10) can be exemplified. General formula (10) [Chemical Formula 60]

[0098] In general formula (10), Ar 91 to Ar 94 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, preferably substituted or unsubstituted aryl groups. n91 and n93 independently represent integers from 0 to 4, and n92 and n94 independently represent integers from 0 to 3. The α-ring, β-ring, γ-ring, and δ-ring may be substituted, with at least one ring being substituted or unsubstituted by an aryl group, or condensed with a substituted benzene ring, or condensed with the furan ring of a substituted or unsubstituted benzofuran, or the thiophene ring of a substituted or unsubstituted thiophene. A1 and A2 independently represent a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n91 to n94 are integers from 0 to 2. In one embodiment of the present invention, n91 and n93 are the same number, and n92 and n94 are the same number. n91 to n94 can all be the same number, for example, all can be 0 or all can be 1. Regarding the preferred groups of Ar 91 to Ar 94, refer to the description of the correspondence of Ar 1 to Ar 4 in general formula (1a). In one embodiment of the present invention, the α ring and γ ring have the same substituents or have the same condensation structure, and the β ring and δ ring have the same substituents or have the same condensation structure. In one embodiment of the present invention, both the β ring and δ ring are substituted with substituted or unsubstituted aryl groups, or condensed with a substituted benzene ring, or condensed with a furan ring of substituted or unsubstituted benzofuran or a thiophene ring of substituted or unsubstituted thiophene. In one embodiment of the present invention, both the α-ring and γ-ring are substituted with substituted or unsubstituted aryl groups, or condensed with a substituted benzene ring, or condensed with a furan ring of a substituted or unsubstituted benzofuran, or a thiophene ring of a substituted or unsubstituted thiophene. In one embodiment of the present invention, the α-ring, β-ring, γ-ring, and δ-ring are all substituted with substituted or unsubstituted aryl groups, or condensed with a substituted benzene ring, or condensed with a furan ring of a substituted or unsubstituted benzofuran, or a thiophene ring of a substituted or unsubstituted thiophene. For a description of A1 and A2 and preferred scope, refer to the corresponding description of general formula (1).

[0099] Specific examples of compounds represented by general formula (10) are given below. The compounds of general formula (10) that can be used in this invention are not to be interpreted as limiting the specific examples given below. [Chemical Formula 61]

[0100] The compound represented by general formula (1) may have a non-symmetrical skeleton. For example, it may be a compound having an asymmetrical skeleton as shown in (11a) or (11b) below. [Chemical Formula 62]

[0101] In the frameworks (11a) and (11b), Z 17 and Z 18 independently represent oxygen atoms or sulfur atoms, respectively. In one embodiment of the present invention, each hydrogen atom in the frameworks (11a) and (11b) may form a ring structure without being substituted together with adjacent hydrogen atoms as a linking group.

[0102] As a preferred group of compounds having a skeleton (11a), compounds represented by the following general formula (11a) can be exemplified. General formula (11a) [Chemical Formula 63]

[0103] In general formula (11a), Ar 83 to Ar 85 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. R 83 and R 84 independently represent substituted or unsubstituted alkyl groups. Z 17 represents an oxygen atom or a sulfur atom. m83 and m84 independently represent integers from 0 to 5. n83 represents an integer from 0 to 4, and n84 and n85 independently represent integers from 0 to 3. For detailed descriptions and preferred ranges of Ar 83~Ar 85, R 83, R 84, m83, m84, n83~n85, please refer to the descriptions of Ar 1, Ar 2, Ar 4, R 41, R 42, m1, m2, n1, n2, and n4 in general formula (1a).

[0104] Specific examples of compounds represented by general formula (11a) are given below. The compounds of general formula (11a) that can be used in this invention are not to be limited by the specific examples below. In the specific examples below, 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 a portion of the X atoms in the molecule are oxygen atoms and the remainder are sulfur atoms can also be used. [Chemical Formula 64]

[0105] As a preferred group of compounds having a skeleton (11b), compounds represented by the following general formula (11b) can be exemplified. General formula (11b) [Chemical Formula 65]

[0106] In general formula (11b), Ar 86 to Ar 88 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, substituted or unsubstituted aryl groups may be preferred. R 86 and R 87 independently represent substituted or unsubstituted alkyl groups. Z 18 represents an oxygen atom or a sulfur atom. m86 and m87 independently represent integers from 0 to 5. n86 represents an integer from 0 to 4, and n87 and n88 independently represent integers from 0 to 3. For detailed descriptions and preferred ranges of Ar 86~Ar 88, R 86, R 87, m86, m87, n86~n88, please refer to the records of Ar 1, Ar 2, Ar 4, R 41, R 42, m1, m2, n1, n2, n4 in general formula (1a).

[0107] Specific examples of compounds represented by general formula (11b) are given below. The compounds of general formula (11b) that can be used in this invention are not to be limited by 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 a portion of the X atoms in the molecule are oxygen atoms and the remainder are sulfur atoms can also be used. [Chemical Formula 66]

[0108] As a compound represented by general formula (1), a compound in which R5 is the donor group is preferably used. Compounds in which R5 is the donor group tend to have a high molar extinction coefficient and high luminous efficiency. For example, they exhibit superior luminescent properties compared to compounds in which R3 is the donor group. In a preferred embodiment of the present invention, R3 is not a donor group. In a preferred embodiment of the present invention, among R1 to R7, only R5 is a donor group or none of them are donor groups (especially donor groups with a σp value of -0.2 or less). The donor group is a group with a negative Hammett σp value. It is preferred that the σp value of the donor group of R5 is -0.2 or less, for example, it can be -0.4 or less, for example, it can also be -0.6 or less. As a preferred donor group, substituted amino groups can be mentioned, preferably substituted or unsubstituted diarylamino groups. The aryl group can be a monocyclic ring or a condensed ring formed by the condensation of two or more rings. In the case of a condensation ring, it is preferable that the number of rings after condensation is 2 to 6, for example, 2 to 4 or two. The two aryl groups constituting the diarylamine can be the same or different. Furthermore, the two aryl groups can be connected by a single bond or a linker. As a substituted or unsubstituted diarylamine, a substituted or unsubstituted diphenylamine is preferred. A substituted or unsubstituted carbazole-9-yl group with two phenyl groups linked by a single bond can be used, or a substituted or unsubstituted diphenylamine group with two phenyl groups not linked by a single bond can be used. When any one of R1 to R7 in general formula (1) is a substituted amino group, it is preferable that at least R5 is a substituted amino group, and it is even more preferable that only R5 is a substituted amino group. In one embodiment of the present invention, R3 is not a substituted amino group. When R5 is a donor group and X1 is a nitrogen atom, it is preferable that R16 or R19 is a donor group, with R19 being a donor group even more preferred. In this case, the other R1 to R26 can all be hydrogen or deuterium atoms, for example, at least one of R3, R6, R15, and R20 can be a substituent (preferably a substituted or unsubstituted alkyl or a substituted or unsubstituted aryl) and the others can be hydrogen or deuterium atoms. When R5 is a donor group and X1 is a boron atom, it is preferable that R20 or R23 is a donor group, with R20 being a donor group even more preferred. In this case, the other R1 to R26 can all be hydrogen or deuterium atoms, for example, at least one of R3, R6, R19, and R24 can be a substituent (preferably a substituted or unsubstituted alkyl or a substituted or unsubstituted aryl) and the others can be hydrogen or deuterium atoms. As a preferred group of compounds with R 5 as the donor group, examples can be shown of compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b). General formula (12a) [Chemical Formula 67]

[0109] In general formulas (12a) and (12b), Ar1 to Ar8 independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl groups, for example, preferably substituted or unsubstituted alkyl groups or preferably substituted or unsubstituted aryl groups. R5 represents a donor group. R41 to R44 independently represent substituted or unsubstituted alkyl groups. m1 to m4 independently represent integers from 0 to 5. n1, n3, n5, and n7 independently represent integers from 0 to 4, n4 and n8 represent integers from 0 to 3, and n2' and n6' represent integers from 0 to 2. A1 and A2 independently represent hydrogen atoms, deuterium atoms, or substituents. For details regarding Ar 1~Ar 8, R 41~R 44, m1~m4, n1, n3~n5, n7, n8, A 1, and A 2, please refer to the corresponding descriptions in general formulas (1a) and (1b). Among them, Ar 1, Ar 3, Ar 5, and Ar 7, which are bonded to adjacent carbon atoms, can bond to each other to form a cyclic structure, preferably forming benzofuran (condensed with a furan ring) or benzothiophene (condensed with a thiophene ring).

[0110] 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 this invention are not to be interpreted as limiting the scope of the following specific examples. In the following specific examples, the structures of each compound are defined by identifying R, Ar, and X in formulas F1 to F56 in the table. R is selected from A to D (described later), Ar from a to d (described later), and X from α to γ. For example, the compound No. 1 in the table is a compound having a structure in formula F1 where R is A and Ar is a.

[0111] [Chemical Formula 68] [Chemical Formula 69] [Chemical Formula 70] [Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73] [Table 1]

[0112] [Chemical Formula 74]

[0113] In one embodiment of the present invention, the skeletons (1a) to (12b) are skeletons that do not further condense with other rings. In another embodiment of the present invention, the skeletons (1a) to (12b) are skeletons that can further condense with other rings. Regarding the other rings described herein, reference can be made to the description of the ring structures formed by the bonding of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R16 and R17, R18 and R19, R19 and R20, R20 and R21, R22 and R23, R23 and R24, R24 and R25, and R25 and R26.

[0114] In one embodiment of the present invention, A1 and A2 of general formula (1) are acceptor groups. For example, compounds in which A1 and A2 are acceptor groups and have any one of the skeletons (1a) to (12b) can be cited. For a description and specific examples of the acceptor groups, please refer to the description and specific examples of the acceptor groups A1 and A2 of the above general formula (1). The following are specific examples of compounds in which A1 and A2 are acceptor groups. The compounds in which A1 and A2 are acceptor groups that can be used in this invention are not to be limited by the following specific examples. In the following specific examples, both A1 and A2 have a structure of “A”, and the structure of each compound is determined by individually identifying that “A”. [Chemical Formula 75]

[0115] In one embodiment of the present invention, a compound having a rotationally symmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, a compound having a linearly symmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (1). Specific examples of compounds having an asymmetric skeleton are given below. The compounds having an asymmetric skeleton or asymmetric structure that can be used in this invention are not to be limited by the specific examples below. Specific examples containing X include 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. Compounds in which a portion of X atoms in the molecule is oxygen atoms and the remainder is sulfur atoms can also be used. [Chemical Formula 76]

[0116] The following are specific examples of compounds that have a symmetrical skeleton but an asymmetrical structure due to asymmetrical bonding of substituents. The compounds with asymmetrical structures that can be used in this invention are not to be limited by the specific examples described below. [Chemical Formula 77]

[0117] In one embodiment of the present invention, R3 in general formula (1) is not a diarylamine (the two aryl groups constituting a diarylamine can be bonded to each other). In a preferred embodiment of the present invention, R3 in general formula (1) is a hydrogen atom, a deuterium atom, or an acceptor group (not a donor group). In one embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or more. In a preferred embodiment of the present invention, at least one of m1 and m2 in general formula (1a) is 1 or more. In a further preferred embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or more, and further at least one of m1 and m2 in general formula (1a) is 1 or more. In one embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or more. In a preferred embodiment of the present invention, at least one of m3 and m4 in general formula (1b) is 1 or more. In a further preferred embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or more, and further at least one of m3 and m4 in general formula (1a) is 1 or more. When at least one of m1 and m2 is 1 or more, and at least one of m3 and m4 is 1 or more, it is preferable that at least one of R41 and R42 and at least one of R43 and R44 are alkyl groups that can be substituted with a deuterium atom, for example, R41 to R44 are all alkyl groups that can be substituted with a deuterium atom. When at least one of n1 to n4 is 1 or more, and at least one of n5 to n8 is 1 or more, it is preferable that at least one of Ar1 to Ar4 and at least one of Ar5 to Ar8 are aryl groups that can be substituted with a deuterium atom or an alkyl group, for example, Ar1 to Ar8 are all aryl groups that can be substituted with a deuterium atom or an alkyl group. In one embodiment of the present invention, when X1 of general formula (1) is a boron atom and R8, R10, R12, R13, R15, and R17 are alkyl (or methyl), at least one of R1~R7, R18~R20, and R23~R26 is a substituent, preferably a group of substituent group E, such as an aryl group that can be substituted by a deuterium atom or an alkyl group. In one embodiment of the present invention, when X2 of general formula (1) is a boron atom and R8, R10, R12, R22, R24, and R26 are alkyl (or methyl), at least one of R1~R7, R13~R16, and R19~R21 is a substituent, preferably a group of substituent group E, such as an aryl group that can be substituted by a deuterium atom or an alkyl group. In one embodiment of the present invention, when X1 of general formula (1) is a boron atom and any one of R8 and R9, R9 and R10 is bonded to any one of R15 and R16, R16 and R17 to form an aromatic ring (or benzene ring), at least one of R1~R7, R18~R20, R23~R26 is a substituent, preferably a group of substituent group E, for example an aryl group that can be substituted by a deuterium atom or an alkyl group. In one embodiment of the present invention, when X2 of general formula (1) is a boron atom and any one of R8 and R9, R9 and R10 is bonded to any one of R22 and R23, R23 and R24 to form an aromatic ring (or benzene ring), at least one of R1 to R7, R13 to R16, R19 to R21 is a substituent, preferably a group of substituent group E, for example an aryl group that can be substituted by a deuterium atom or an alkyl group. In one embodiment of the present invention, R9 and R11 of general formula (1) are neither cyano nor alkyl. That is, R9 and R11 are hydrogen atoms, deuterium atoms, or substituents other than cyano and alkyl. In one embodiment of the present invention, R9 and R11 of general formula (1) are neither cyano nor tert-butyl. In a preferred embodiment of the present invention, at least one of R8 to R12 in general formula (1) is a substituent. In one embodiment of the present invention, R3 of general formula (1) is not a substituted amino or aryl group. In one embodiment of the present invention, R3 of general formula (1) is not a substituted amino or phenyl group. In one embodiment of the present invention, R3 of general formula (1) is not dimethylamino, diphenylamino, or phenyl. In a preferred embodiment of the present invention, at least one of R1 to R26 in general formula (1) is a substituent, and more preferably at least one of R1 to R26 is an alkyl group, for example an alkyl group having 1 to 4 carbon atoms.

[0118] For example, when intending to form an organic layer containing a compound represented by general formula (1) into a film by vapor deposition, it is preferable that the molecular weight of the compound represented by general formula (1) is 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 900 or less. The lower limit of molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). Preferably, it is 624 or more.

[0119] It is preferable that the compound represented by general formula (1) does not contain metal atoms. The metal atoms mentioned herein do not include boron atoms. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, sulfur atoms, and boron atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and boron atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, sulfur atoms, and boron atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and boron atoms can be selected. For example, as a compound represented by general formula (1), it is possible to select a compound composed of atoms selected from the group including carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms and boron atoms.

[0120] The compounds represented by general formula (1) can be synthesized by combining known reactions. For example, they can be synthesized by using ring-closing reactions or substitution reactions.

[0121] In this specification, "alkyl" can be any of the following: straight-chain, branched, or cyclic. Furthermore, two or more of the straight-chain, cyclic, and branched moieties can be mixed together. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodexyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group may be further substituted with an aryl group. The "alkenyl" group can be any of the following: linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched groups can be mixed together. The number of carbon atoms in the alkenyl group can be, for example, 2 or more, or 4 or more. Alternatively, 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 alkenyl groups include vinyl, propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl. The substituent alkenyl group can be further substituted with substituents. "Aryl" and "heteroaryl" can be monocyclic or condensed rings formed by the condensation of two or more rings. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, for example, 2 to 4. Specific examples of rings include benzene rings, pyridine rings, pyrimidine rings, triphenyl rings, naphthyl rings, anthracene rings, phenanthrene rings, biphenyl rings, quinoline rings, pyridine rings, quinoline rings, and naphthyl rings, or rings formed by the condensation of these. Specific examples of aryl or heteroaryl groups include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 2-pyridyl, 3-pyridyl, and 4-pyridyl. The number of atoms constituting the aryl ring skeleton is preferably 6 to 40, more preferably 6 to 20, and can be selected from the range of 6 to 14 or from the range of 6 to 10. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and can be selected within the range of 5 to 14 or within the range of 5 to 10. "Extensive aryl" and "heteroaryl" can be set to replace the valence number in the description of aryl and heteroaryl groups with 2 instead of 1.

[0122] In this specification, "substituent group A" indicates a group selected from hydroxyl, halogen atoms (e.g., fluorine, chlorine, bromine, iodine), alkyl (e.g., 1-40 carbon atoms), alkoxy (e.g., 1-40 carbon atoms), alkylthio (e.g., 1-40 carbon atoms), aryl (e.g., 6-30 carbon atoms), aryloxy (e.g., 6-30 carbon atoms), arylthio (e.g., 6-30 carbon atoms), heteroaryl (e.g., 5-30 ring skeleton atoms), and heteroaryloxy (e.g., 5-30 ring skeleton atoms). A group formed by combining one or more groups from the group consisting of 5 to 30 atoms, heteroarylthio (e.g., a ring skeleton consisting of 5 to 30 atoms), acetylated (e.g., 1 to 40 carbon atoms), alkenyl (e.g., 1 to 40 carbon atoms), alkoxycarbonyl (e.g., 1 to 40 carbon atoms), aryloxycarbonyl (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl (e.g., 1 to 40 carbon atoms), silyl (e.g., a trialkylsilyl group consisting of 1 to 40 carbon atoms), and nitro. In this specification, "substituent group B" means a group formed by selecting one or more groups selected from the group consisting of alkyl (e.g., 1 to 40 carbon atoms), alkoxy (e.g., 1 to 40 carbon atoms), aryl (e.g., 6 to 30 carbon atoms), aryloxy (e.g., 6 to 30 carbon atoms), heteroaryl (e.g., 5 to 30 atoms constituting the ring skeleton), heteroaryloxy (e.g., 5 to 30 atoms constituting the ring skeleton), and diarylamine (e.g., 0 to 20 carbon atoms). In this specification, "substituent group C" means a group formed by one or more groups selected from the group consisting of alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms), heteroaryl (e.g., 5 to 20 cyclic skeleton atoms), and diarylamine (e.g., 12 to 20 carbon atoms). In this specification, "substituent group D" means a group formed by one or more groups selected from the group consisting of alkyl (e.g., having 1 to 20 carbon atoms), aryl (e.g., having 6 to 22 carbon atoms), and heteroaryl (e.g., having 5 to 20 cyclic skeleton atoms). In this specification, "substituent group E" means a group formed by one or more groups selected from the group consisting of alkyl (e.g., having 1 to 20 carbon atoms) and aryl (e.g., having 6 to 22 carbon atoms). In this specification, the term "substituent" or "substituted or unsubstituted" can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0123] [Compounds represented by general formula (2)] Next, the compounds represented by the following general formula (2) will be described. General formula (2) [Chemical Formula 78]

[0124] In general formula (2), X 11 represents O, S, N(RA) or C(RB)(RC). In one embodiment of the present invention, X 11 is O, S or N(RA). In one embodiment of the present invention, X 11 is O or S. In one embodiment of the present invention, X 11 is N(RA). In one embodiment of the present invention, X 11 is O. In one embodiment of the present invention, X 11 is S. When X 11 is O, S or C(RB)(RC), L is bonded to a benzene ring bonded to (R 115)n. When X 11 is N(RA), L is bonded to a benzene ring bonded to (R 115)n or to the N bond represented by X 11. As explained herein, the bond extending to the right from L represents a benzene ring bonded to (R 115)n or, when X 11 is N, a bond to X 11 (i.e., N).

[0125] In general formula (2), A11 and A12 are independently benzene rings, furan rings, thiols, pyrrole rings, or cyclopentadiene rings, which may be further condensed with other rings or substituted. In a preferred embodiment of the present invention, A11 is a benzene ring. In a preferred embodiment of the present invention, A12 is a benzene ring. In a further preferred embodiment of the present invention, both A11 and A12 are benzene rings. In a embodiment of the present invention, at least one of A11 and A12 is a furan ring, a thiols, a pyrrole ring, or a cyclopentadiene ring. In a embodiment of the present invention, at least one of A11 and A12 is a furan ring. In a embodiment of the present invention, at least one of A11 and A12 is a thiols. In a embodiment of the present invention, at least one of A11 and A12 is a pyrrole ring. In one embodiment of the present invention, at least one of A11 and A12 is a cyclopentadiene ring. The benzene ring, furan ring, thiol ring, pyrrole ring, and cyclopentadiene ring described herein can also be condensed with other rings. The condensed ring can be any one of aromatic hydrocarbon rings, aromatic heterocycles, aliphatic hydrocarbon rings, and aliphatic heterocycles, and can also be two or more of these condensed rings. Preferably, it is an aromatic hydrocarbon ring, an aromatic heterocycle, or a ring formed by the condensation of two or more of these. Benzene rings are an example of aromatic hydrocarbon rings. Aromatic heterocycles refer to rings exhibiting aromaticity by including heteroatoms as ring backbone atoms; 5- to 7-membered rings are preferred, for example, 5-membered or 6-membered rings can be used. In one embodiment of the invention, furan rings, thiophene rings, and pyrrole rings can be used as aromatic heterocycles. Aliphatic hydrocarbon rings are preferably hydrocarbon rings that do not exhibit aromaticity; 5- to 7-membered rings are preferred, for example, 5-membered or 6-membered rings can be used. For example, cyclopentadiene rings can be used. Aliphatic heterocycles are rings that contain heteroatoms as the ring backbone and do not exhibit aromaticity. 5-7 membered rings are preferred, for example, 5-membered or 6-membered rings can be used. In one embodiment of the present invention, A11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or two or more of the like. In one embodiment of the present invention, A11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or two or more of the like. In one embodiment of the present invention, A11 is a benzene ring, and the benzene ring is condensed with the furan ring of benzofuran or the thiophene ring of benzothiophene. In one embodiment of the present invention, A11 is condensed with the furan ring of benzofuran. In one embodiment of the present invention, A11 is condensed with the thiophene ring of benzothiophene. In one embodiment of the present invention, A12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or two or more of the like. In one embodiment of the present invention, A12 is a benzene ring, and the benzene ring is further condensed with a ring formed by the condensation of a benzene ring, a furan ring, a thiol ring, or two or more of the like. In one embodiment of the present invention, A12 is a benzene ring, and the benzene ring is condensed with the furan ring of benzofuran or the thiophene ring of benzothiophene. In one embodiment of the present invention, A12 is condensed with the furan ring of benzofuran. In one embodiment of the present invention, A12 is condensed with the thiophene ring of benzothiophene. The hydrogen atoms constituting the A11 or A12 ring may be substituted with deuterium atoms or substituents. Substituents may be selected from any of the substituent groups A to E, for example, from substituent group E. In one embodiment of the invention, the A11 or A12 ring may be substituted with a group selected from one or more atoms or groups, or combinations thereof, of the group consisting of deuterium atoms, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups, and cyano groups. In one embodiment of the invention, the A11 or A12 ring may be substituted with a group consisting of deuterium atoms, alkyl groups, aryl groups, or combinations thereof. In one embodiment of the invention, at least one of the A11 or A12 rings is substituted with a group consisting of deuterium atoms, alkyl groups, aryl groups, or combinations thereof. Furthermore, when a pyrrole ring is included as a constituent ring of A11 or A12, it is preferable that the nitrogen atom in the pyrrole ring's ring skeleton is bonded to an aryl group that can be substituted by a deuterium atom, alkyl group, or aryl group (the same applies to the nitrogen atom in the indole ring described later). When two or more hydrogen atoms constituting the A11 or A12 ring are substituted, they can be substituted by the same atom or group, or they can be substituted by different atom or group.

[0126] In general formula (2), R 111~R 114, RB, and RC independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group, respectively. R 115 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond with L (i.e., a single bond with L). RA represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L (i.e., a single bond with L). For aryl, heteroaryl, and alkyl groups, refer to the above description of "aryl," "heteroaryl," and "alkyl." It is preferred that the aryl group has 6 to 14 carbon atoms, for example, phenyl, 1-naphthyl, and 2-naphthyl. The heteroaryl group is preferably composed of a 5-membered or 6-membered ring, such as 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazole-9-yl, dibenzofuranyl, and dibenzothiopheneyl. The alkyl group is preferably composed of 1 to 6 carbon atoms, such as methyl, ethyl, isopropyl, and tributyl. These aryl, heteroaryl, and alkyl groups can be substituted. In the case of substitution, substitution with a group selected from one or more atoms or groups of the group consisting of deuterium, aryl, heteroaryl, alkyl, and cyano is preferred; substitution with a group selected from one or more atoms or groups of the group consisting of deuterium, aryl, heteroaryl, and alkyl is even more preferred. In one embodiment of the invention, R 112 is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or cyano group. In one embodiment of the present invention, R 111 to R 114 are each independently a hydrogen atom or a deuterium atom. R111 and R112, R112 and R113, R113 and R114, two adjacent R115, RB and RC can bond together to form a cyclic structure. Regarding the cyclic structure described herein, refer to the description of the rings further condensed with the benzene ring in the descriptions of A11 and A12 above. In one embodiment of the invention, one group of R111 and R112, R112 and R113, and R113 and R114 bonds together to form a benzofuran ring (condensed with a furan ring), a benzothiophene ring (condensed with a thiophene ring), or an indole ring (condensed with a pyrrole ring).

[0127] In one embodiment of the present invention, the group bonded from the left side to L in general formula (2) is a substituted or unsubstituted carbazole-9-yl. For example, it is a carbazole-9-yl substituted with a group obtained by deuterium, alkyl, aryl, or a combination thereof at the 3 or 6 position (preferably both). Alternatively, it can be an unsubstituted carbazole-9-yl. In one embodiment of the present invention, the group bonded from the left side to L in general formula (2) is benzo[2,3-a]carbazole-9-yl, benzo[3,2-a]carbazole-9-yl, benzo[2,3-b]carbazole-9-yl, benzo[3,2-b]carbazole-9-yl, or benzo[2,3-c]carbazole-9-yl (these groups can be substituted, for example, unsubstituted). In one embodiment of the present invention, the group bonded from the left to L in general formula (2) is benzothieno[2,3-a]carbazole-9-yl, benzothieno[3,2-a]carbazole-9-yl, benzothieno[2,3-b]carbazole-9-yl, benzothieno[3,2-b]carbazole-9-yl, benzothieno[2,3-c]carbazole-9-yl, benzothieno[3,2-c]carbazole-9-yl (these groups may be substituted, for example, unsubstituted). In one embodiment of the present invention, the group bonded from the left to L in general formula (2) is indo[2,3-a]carbazole-9-yl, indo[3,2-a]carbazole-9-yl, indo[2,3-b]carbazole-9-yl, indo[3,2-b]carbazole-9-yl, indo[2,3-c]carbazole-9-yl, indo[3,2-c]carbazole-9-yl (these groups may be substituted, for example, unsubstituted). In one embodiment of the present invention, the group bonded from the right side to L in general formula (2) can also be the group exemplified above as the group bonded from the left side to L. However, it is not an unsubstituted carbazole-9-yl. When X 11 in general formula (2) is N and L is bonded to the N, at least one of R 115 or at least one of the groups bonded to the ring represented by A 12 is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a cyano. That is, when X 11 is N and L is bonded to the N, at least one substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a cyano exists among the groups bonded from the right side to L.

[0128] In the following examples, specific examples of groups that can be used as the group bonded from the left side of L in general formula (2) are given. However, the groups that can be used in this invention are not to be limited by these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. Therefore, for example, D2 or D3 is methylated. * indicates the bonding position with L. [Chemical Formula 79]

[0129] In addition to the specific examples mentioned above, groups in which all hydrogen atoms of the alkyl groups of D2, D3, D5, D7~D12, D87~D104, and D179~D196 are replaced with deuterium atoms are illustrated here in the form of D2(m), D3(m), D5(m), D7(m)~D12(m), D87(m)~D104(m), and D179(m)~D196(m), respectively. Furthermore, groups in which the phenyl groups of D4~D6, D19~D86, and D111~D178 are deuterated and replaced with C6D5 groups are illustrated here in the form of D4(p)~D6(p), D19(p)~D86(p), and D111(p)~D178(p), respectively. Furthermore, all hydrogen atoms of D1 to D196 that are deuterated are exemplified here in the form of D1(D) to D196(D).

[0130] Regarding specific examples of groups that can be used as the group bonded to the right side of L in general formula (2), in addition to the aforementioned D2~D196 and such deuterium-substituted derivatives, the following specific examples can be given. However, the groups that can be used in this invention are not to be interpreted as limiting by these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. * indicates the bonding position with L. [Chemical Formula 80]

[0131] In addition to the specific examples mentioned above, the deuterated CD3-substituted groups of the methyl (CH3) groups of X31~X33 and X64~X79 are illustrated here as X31(m)~X33(m) and X64(m)~X79(m), respectively. Furthermore, the deuterated C6D5-substituted groups of the phenyl (C6H5) groups of X5~X21, X38~X54, and X68~X70 are illustrated here as X5(p)~X21(p), X38(p)~X54(p), and X68(p)~X70(p), respectively. Moreover, the groups in which all hydrogen atoms of X1~X79 are deuterated are illustrated here as X1(D)~X79(D).

[0132] In general formula (2), n represents an integer of 3 or 4. When X 11 is O, S, or C(RB)(RC), L is bonded to the benzene ring of (R 115)n, so n is 3. When X 11 is N(RA) and L is bonded to the benzene ring of (R 115)n, N is 3, and when X 11 is N(RA) and L is bonded to the N represented by X 11, N is 4. The n R 115s can be the same or different from each other.

[0133] In general formula (2), L represents a single bond, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a linking group formed by two or more such bonds. The aryl structure of the aryl group and the heteroaryl structure of the heteroaryl group can be referred to the above description of "aryl" and "heteroaryl". The aryl and heteroaryl groups can be substituted. In the case of substitution, substitution with a group selected from one or more atoms or groups of the group consisting of deuterium, aryl, heteroaryl, alkyl, and cyano is preferred, and substitution with a group selected from one or more atoms or groups of the group consisting of deuterium, aryl, heteroaryl, and alkyl is even more preferred. In the case of substitution, methyl, ethyl, isopropyl, tributyl, phenyl, or deuterated forms of these are preferred. In one embodiment of the present invention, L is an unsubstituted aryl group. Specific examples of L are given below. However, the L used in this invention is not to be limited by these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are methyl-substituted. * indicates the bond position. L1 is a single bond.

[0134] [Chemical Formula 81]

[0135] In one embodiment of the present invention, the groups bonded to the left side of L in general formula (2) are selected from D1 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated forms (Concept 1). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D1 to D12 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated forms (Concept 2). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D13 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated forms (Concept 3). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D1 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X66 and their deuterated forms (Concept 4). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D1 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X33 and their deuterated forms (Concept 5). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D1 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X1 to X21, X31 to X33 and their deuterated forms (Concept 6). In one embodiment of the present invention, the groups bonded to the left side of L are selected from D1 to D196 and their deuterated forms, and the groups bonded to the right side of L are selected from X22 to X30 and their deuterated forms (Concept 7). In one embodiment of the present invention, in embodiment 1, L is L1. In one embodiment of the present invention, in embodiment 2, L is L1. In one embodiment of the present invention, in embodiment 3, L is L1. In one embodiment of the present invention, in embodiment 4, L is L1. In one embodiment of the present invention, in embodiment 5, L is L1. In one embodiment of the present invention, in embodiment 6, L is L1. In one embodiment of the present invention, in embodiment 7, L is L1. In one embodiment of the present invention, in embodiment 1, L is L6. In one embodiment of the present invention, in embodiment 2, L is L6. In one embodiment of the present invention, in embodiment 3, L is L6. In one embodiment of the present invention, in embodiment 4, L is L6. In one embodiment of the present invention, in embodiment 5, L is L6. In one embodiment of the present invention, in embodiment 6, L is L6. In one embodiment of the present invention, in embodiment 7, L is L6. In one embodiment of the present invention, in embodiment 1, L is L14. In one embodiment of the present invention, in embodiment 2, L is L14. In one embodiment of the present invention, in embodiment 3, L is L14. In one embodiment of the present invention, in embodiment 4, L is L14. In one embodiment of the present invention, in embodiment 5, L is L14. In one embodiment of the present invention, in embodiment 6, L is L14. In one embodiment of the present invention, in embodiment 7, L is L14. In one embodiment of the present invention, in embodiment 1, L is L16. In one embodiment of the present invention, in embodiment 2, L is L16. In one embodiment of the present invention, in embodiment 3, L is L16. In one embodiment of the present invention, in embodiment 4, L is L16. In one embodiment of the present invention, in embodiment 5, L is L16. In one embodiment of the present invention, in embodiment 6, L is L16. In one embodiment of the present invention, in embodiment 7, L is L16.

[0136] Specific examples of compounds represented by general formula (2) are shown below. The compounds represented by general formula (2) that can be used in this invention are not to be interpreted as limitingly specific in the following examples.

[0137] [Chemical Formula 82]

[0138] In addition to the specific examples mentioned above, compounds in which all hydrogen atoms present in the substituted or unsubstituted carbazole-9-group of H1 to H13, H18, H19, H23, H25, and H26 are substituted with deuterium atoms are illustrated here as H1(d) to H13(d), H18(d), H19(d), H23(d), H25(d), and H26(d), respectively. Furthermore, compounds in which all hydrogen atoms present in H1 to H26 are substituted with deuterium atoms are illustrated here as H1(D) to H26(D), respectively.

[0139] In one embodiment of the present invention, the compound represented by the following general formula is selected as the compound represented by general formula (2). [Chemical Formula 83]

[0140] In the above general formula, R 141 to R 147 independently represent a hydrogen atom, a deuterium atom, or a substituent, and at least one of R 141 to R 147 is a substituted or unsubstituted aryl group. Q represents a substituted or unsubstituted 12H-benzofluorocarbazole-12-ylphenyl group. In one embodiment of the present invention, R 141 to R 147 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. In another embodiment of the present invention, R 141 to R 147 are each independently a hydrogen atom, a deuterium atom, or an aryl group that can be substituted by a group selected from the group consisting of deuterium, alkyl, and aryl groups, or a combination thereof. In a preferred embodiment of the present invention, only one of R 141 to R 147 is an aryl group that can be substituted by a group selected from the group consisting of deuterium, alkyl, and aryl groups, or a combination thereof, while the remaining portions are each independently a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, one of R 141 to R 147 is selected from P1 to P14 described later. In one embodiment of the present invention, Q is a 12H-benzofluorocarbazole-12-ylphenyl group that can be substituted with a group selected from one or more atoms or groups selected from the group consisting of deuterium, alkyl, and aryl groups. In another embodiment of the present invention, Q is an unsubstituted 12H-benzofluorocarbazole-12-ylphenyl group. In a preferred embodiment of the present invention, Q is selected from Q1 to Q18 as described below. The following table shows specific examples of compounds represented by the above general formula. In Table 1, the structure of the compounds is determined by showing Q and R 141 to R 147 for each compound. For example, compound 141-1-1 is a compound with Q as Q1, R 141 as P1, and R 142 to R 147 as hydrogen atoms, and compound 141-1-2 is a compound with Q as Q1, R 141 as P2, and R 142 to R 147 as hydrogen atoms. In each section of Table 2, the 14 structures are summarized and identified in one section. For example, in the section “141-1-1 to 141-1-14” of Table 2, the compounds with Q as Q1, R 141 as P1 to P14, and R 142 to R 147 as hydrogen atoms are summarized and identified sequentially as compounds 141-1-1 to 141-1-14. The structures of compounds 141-1-1 to 141-1-14 summarized here correspond to the structures of compounds 141-1-1 to 141-1-14 identified in Table 1. For the section “141-2-1 to 141-2-14” in Table 2, compounds with Q as Q2, R 141 as P1 to P14, and R 142 to R 147 as hydrogen atoms are summarized and identified as compounds 141-2-1 to 141-2-14 in sequence. The structures of the subsequent sections are determined using the same method. Each compound identified in Table 2 is disclosed separately in this specification.

[0141] [Table 1] [Table 2]

[0142] [Chemical Formula 84] [Chemical Formula 85]

[0143] For example, when intending to form an organic layer containing a compound represented by general formula (2) into a film by vapor deposition, it is preferable that the molecular weight of the compound represented by general formula (2) is 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 800 or less, for example, 600 or less. The lower limit of molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (2).

[0144] Compounds represented by general formula (2) with smaller dipole moments exhibit higher orientation during film formation, and are therefore preferred. This tendency is particularly pronounced in the region of dipole moments between 0.9 and 2.5. A dipole moment less than 2.3 is preferred, and less than 2.0 is even more preferred; for example, selection can be made from a region less than 1.7 or less than 1.4. Alternatively, selection can be made from a region greater than 0.4 or greater than 0.9.

[0145] As a compound represented by general formula (2), it is possible to select compounds composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. For example, as a compound represented by general formula (2), it is possible to select compounds composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. For example, as a compound represented by general formula (2), it is possible to select compounds composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. For example, as a compound represented by general formula (2), it is possible to select compounds composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms.

[0146] [membrane] The membrane of the present invention comprises a compound represented by general formula (1) and a compound represented by general formula (2). The membrane of the present invention may be composed solely of compounds represented by general formula (1) and general formula (2), or may contain other materials. The membrane of the present invention may contain two or more compounds represented by general formula (1). Furthermore, the membrane of the present invention may contain two or more compounds represented by general formula (2). In one embodiment of the present invention, the membrane of the present invention contains one compound represented by general formula (1) and one compound represented by general formula (2). It is preferable that the membrane of the present invention contains more of the compound represented by general formula (2) than the compound represented by general formula (1). In one embodiment of the present invention, when the compound represented by general formula (2) is set to 100 parts by weight, the content of the compound represented by general formula (1) is 0.01 to 49 parts by weight, preferably 0.1 to 30 parts by weight, for example 1 to 20 parts by weight.

[0147] When the film of the present invention comprises materials other than those represented by general formula (1) and general formula (2) (hereinafter referred to as "other materials"), it is preferable to use, for example, a compound whose lowest excited singlet energy is greater than that of the compound represented by general formula (1) and less than that of the compound represented by general formula (2). Such a compound can be used as an auxiliary dopant. When the film of the present invention contains an auxiliary dopant, it is preferable that the auxiliary dopant is a delayed fluorescence material. It is preferable that the content of the auxiliary dopant is greater than that of the compound represented by general formula (1) and less than that of the compound represented by general formula (2). When the total amount of the auxiliary dopant, the compound represented by general formula (1) and the compound represented by general formula (2) is set to 100 parts by weight, it is preferable that the auxiliary dopant is 0.5 to 40 parts by weight, more preferably 1 to 35 parts by weight, and for example, it can be set to 5 to 30 parts by weight.

[0148] The difference ΔEST between the lowest excitation singlet energy and the lowest excitation triplet energy at 77 K in the delayed fluorescence material used in the film of the present invention is preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, further 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. If ΔEST is small, it can easily transition from the excited singlet state to the excited triplet state by absorbing thermal energy, thus functioning as a thermally activated delayed fluorescence material. Thermally activated delayed fluorescence materials can absorb the heat emitted by the device and relatively easily transition from the excited triplet state to the excited singlet state, efficiently contributing the energy of the excited triplet state to luminescence.

[0149] The lowest excited singlet energy (ES1) and lowest excited triplet energy (ET1) of the compounds in this invention are obtained by the following steps. ΔEST is the value obtained by calculating ES1-ET1. (1) Lowest excitation singlet energy (E S1) Prepare a thin film or toluene solution (concentration 10⁻⁵ mol / L) of the target compound as the sample. Measure the fluorescence spectrum of the sample at room temperature (300 K). In the fluorescence spectrum, the vertical axis is set to emission, and the horizontal axis is set to wavelength. Plot a tangent line relative to the rising short-wavelength side of the emission spectrum, and determine the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis. Convert this wavelength value to an energy value using the following conversion formula, and denote the value as E S1. Conversion formula: E S1[eV]=1239.85 / λedge Regarding the determination of the emission spectrum in the embodiments described later, an LED light source (M300L4 manufactured by Thorlabs, Inc.) was used as the excitation source, and the determination was performed using a detector (Made by Hamamatsu Photonics KK, PMA-12 multi-channel spectrometer C10027-01). (2) Minimum excited triplet energy (E T1) The same sample used in the determination of the lowest excitation singlet energy (ES1) was cooled to 77 K using liquid nitrogen. Excitation light (300 nm) was then irradiated onto the phosphorescence sample, and phosphorescence was measured using a detector. The emission 100 ms after excitation was defined as the phosphorescence spectrum. A tangent was plotted relative to the rising short-wavelength side of this phosphorescence spectrum, and the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis was determined. The value obtained by converting this wavelength value into an energy value using the following conversion formula is defined as ET1. Conversion formula: ET1[eV] = 1239.85 / λedge The rising tangent relative to the short-wavelength side of the phosphorescence spectrum is plotted as follows. As the spectral curve moves from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum within the spectral maxima, the tangents at various points on the curve towards the long-wavelength side are considered. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent plotted at the point where this slope reaches its maximum is defined as the rising tangent relative to the short-wavelength side of the phosphorescence spectrum. Furthermore, the point where the maximum peak intensity of the spectrum is less than 10% of the maximum peak intensity is not included in the maximum value of the shortest wavelength side, but is closest to the maximum value of the shortest wavelength side, is the tangent line drawn at the point where the slope value is maximized, which is set as the rising tangent line relative to the short wavelength side of the phosphorescence spectrum.

[0150] In a preferred embodiment of the present invention, a compound having a cyanobenzene structure having one cyano group substituted for a benzene ring (cyanobenzene derivative) is used as a delayed fluorescent material. In another preferred embodiment of the present invention, a compound having a dicyanobenzene structure having two cyano groups substituted for a benzene ring (dicyanobenzene derivative) is used as a delayed fluorescent material. In yet another preferred embodiment of the present invention, a compound having an azirbenzene structure having at least one nitrogen atom substituted for a benzene ring in its ring skeleton (azirbenzene derivative) is used as a delayed fluorescent material. In yet another preferred embodiment of the present invention, a compound having a diaryltriylbenzene group substituted for a benzene ring is used as a delayed fluorescent material.

[0151] The following examples illustrate delayed fluorescent materials that can be used in this invention. However, the delayed fluorescent materials that can be used in this invention are not to be interpreted as limiting by the following examples. [Chemical Formula 86]

[0152] In addition to the above, known delayed fluorescence materials can be appropriately combined with compounds represented by general formula (1) in this invention. Furthermore, even unknown delayed fluorescence materials can be used. Examples of delayed fluorescence materials include segments 0008-0048 and 0095-0133 of WO2013 / 154064, segments 0007-0047 and 0073-0085 of WO2013 / 011954, segments 0007-0033 and 0059-0066 of WO2013 / 011955, and segments 0008-0099 of WO2013 / 081088. Paragraphs 71 and 0118-0133, paragraphs 0009-0046 and 0093-0134 of Japanese Patent Application Publication No. 2013-256490, paragraphs 0008-0020 and 0038-0040 of Japanese Patent Application Publication No. 2013-116975, paragraphs 0007-0032 and 0079-0084 of WO2013 / 133359, and paragraph 00007-0032 and 0079-0084 of WO2013 / 161437. Paragraphs 08-0054 and 0101-0121, paragraphs 0007-0041 and 0060-0069 of Japanese Patent Application Publication No. 2014-9352, paragraphs 0008-0048 and 0067-0076 of Japanese Patent Application Publication No. 2014-9224, paragraphs 0013-0025 of Japanese Patent Application Publication No. 2017-119663, and paragraphs 0013-0054 of Japanese Patent Application Publication No. 2017-119664. Compounds contained in the general formulas described in paragraph 26, paragraphs 0012 to 0025 of Japanese Patent Application Publication No. 2017-222623, paragraphs 0010 to 0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, especially exemplary compounds that emit delayed fluorescence.Furthermore, Japanese Patent Application Publication Nos. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, and WO2014 / 133121 may also be adopted. Notices, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO201 Japanese Publication No. 5 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Publication No. 2015-129240, WO2015 / 129714, WO2015 / 129 The luminescent materials described in Publications No. 715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541 that emit delayed fluorescence. Furthermore, the aforementioned publications described in this paragraph are incorporated herein by reference as part of this specification.

[0153] It is preferable that the delayed fluorescence material used in this invention does not contain metal atoms. For example, as a delayed fluorescence material, a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected. For example, as a delayed fluorescence material, a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as a delayed fluorescence material, a compound composed of carbon atoms, hydrogen atoms, and nitrogen atoms can be selected.

[0154] In the film of the present invention, a luminescent material may be included as another material, which is a compound whose excitation singlet energy is lower than that represented by general formula (1) or general formula (2). In this case, the compound represented by general formula (1) functions as an auxiliary dopant, and it is preferable that the luminescent material, as another material, mainly emits light. As the luminescent material, a delayed fluorescence material may be selected. It is preferable that the content of the luminescent material is less than that of the compound represented by general formula (1) or general formula (2). When the total amount of the compound represented by general formula (1), the compound represented by general formula (2), and the luminescent material is set to 100 parts by weight, it is preferable that the content of the luminescent material is 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, and even more preferably 0.3 to 3 parts by weight. As luminescent materials, anthracene derivatives, pyrene derivatives, perylene derivatives, phosphine derivatives, fluorene derivatives, coumarin derivatives, pyran derivatives, piracene derivatives, anthryl derivatives, pyrrole methylene derivatives, biphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacrine derivatives, diazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julonidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn) can be used. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons can be combined with each other. The following examples illustrate luminescent materials that can be used in the films of the present invention. Furthermore, compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 may also be used.

[0155] [Chemical Formula 87]

[0156] The method for manufacturing the membrane of the present invention is not particularly limited. In one embodiment, the membrane of the present invention can be formed by a wet process. In the wet process, a solution obtained by dissolving the composition containing the compound of the present invention is coated on a surface, and a membrane is formed after the solvent is removed. Examples of wet processes include spin coating, slot coating, inkjet printing, gravure printing, offset printing, and flexographic printing, but are not limited to these. In the wet process, a suitable organic solvent is selected that can dissolve the composition of the membrane material, including the compound of general formula (1) and the compound of general formula (2). In one embodiment, a substituent (e.g., an alkyl group) that improves the solubility in an organic solvent is introduced into the compound contained in the composition. Furthermore, in one embodiment, a thin film containing the compound of the present invention can be formed by a dry process. In one embodiment, vacuum evaporation can be used as the dry process, but is not limited to this. In the case of vacuum evaporation, the compounds constituting the thin film can be co-deposited from a single evaporation source, or from a single evaporation source containing a mixture of compounds. When using a single evaporation source, a mixture of powders containing the compounds, a compressed molded body containing the compressed powder, or a mixture in which the compounds are heated, melted, and then cooled can be used. In one embodiment, by co-depositing under conditions where the evaporation rates (weight loss rates) of the plurality of compounds contained in a single evaporation source are consistent or nearly consistent, a film with a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the evaporation source can be formed. As long as the evaporation source is a mixture of plurality of compounds with the same composition ratio as the formed film, a film with the desired composition ratio can be easily formed. In one embodiment, the temperature at which the compounds to be co-deposited achieve the same weight loss rate can be determined and used as the temperature for co-depositing. The thickness of the film of the present invention can be appropriately determined according to the application. For example, in the case of use for light emission, it can be set in the range of 0.5 to 100 μm. The compound represented by general formula (1) of the membrane of the present invention has high orientation. This high orientation can be achieved by combining it with the compound represented by general formula (2). In particular, even higher orientation can be achieved by combining it with the compound represented by general formula (2) and a compound with a low dipole moment. The compound represented by general formula (1) is horizontally oriented along the membrane surface, thus increasing the luminous efficiency. The orientation can be evaluated by the orientation value (S value). The larger the negative value (the smaller the numerical value), the higher the orientation. The orientation value (S value) can be determined by the method described in Scientific Reports 2017, 7, 8405. It is preferred that the orientation value of the compound represented by general formula (1) in the membrane of the present invention is -0.33 or less, more preferably -0.38 or less, and even more preferably -0.41 or less. In one embodiment, the membrane of the present invention emits delayed fluorescence. In one embodiment of the present invention, when the film of the present invention is excited by a thermal or electronic mechanism, it is able to emit light in the UV region, the blue, green, yellow, orange, and red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region. In one embodiment, the membrane of the present invention does not contain any metallic elements. The metallic elements described herein do not include boron. In one embodiment, the membrane of the present invention can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, sulfur atoms, and boron atoms. Alternatively, the membrane of the present invention can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and boron atoms.

[0157] Organic light-emitting elements The organic light-emitting element of the present invention is an organic light-emitting element using the compound represented by general formula (1) and the compound represented by general formula (2). In one embodiment, the organic light-emitting element includes a light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by general formula (2) assists the light radiation of the light-emitting material represented by general formula (1). In one embodiment, the light-emitting layer is the film of the present invention described above. In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least a light-emitting layer. In one embodiment, the organic layer includes only a light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include hole transport layers, hole injection layers, electron barrier layers, hole barrier layers, electron injection layers, electron transport layers, and exciton barrier layers. In one embodiment, the hole transport layer can be a hole injection transport layer with hole injection function, and the electron transport layer can be an electron injection transport layer with electron injection function.

[0158] The following describes each layer except for the components of the organic electroluminescent element and the light-emitting layer.

[0159] Substrate: In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, which is not particularly limited, as long as any material commonly used in organic electroluminescent elements, such as glass, transparent plastic, quartz and silicon, is used.

[0160] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the aforementioned metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the aforementioned metal is Au. In some embodiments, the conductive transparent material can be 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 aforementioned anode is a thin film. In some embodiments, the aforementioned thin film is fabricated by vapor deposition or sputtering. In some embodiments, the aforementioned thin film is patterned using photolithography. In some embodiments, when high precision of the pattern is not required (e.g., approximately 100 μm or higher), the pattern can be formed by vapor deposition or sputtering of the electrode material using a mask of a preferred shape. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as printing or coating can be used. In some embodiments, the anode has a transmittance exceeding 10% when radiated light passes through it, and the anode has a sheet resistance of less than several hundred ohms 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.

[0161] cathode: In some embodiments, the cathode is made of electrode materials such as metals (below 4 eV) with low work functions (referred to as electron-injecting metals), alloys, conductive compounds, or combinations thereof. In some embodiments, the electrode material can be selected from sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, indium, lithium-aluminum mixtures, and rare earth elements. In some embodiments, a mixture of the electron-injecting metal and a stable metal, i.e., a second metal, with a work function higher than that of the electron-injecting metal can be used. In some embodiments, the mixture can be selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, lithium-aluminum mixtures, and aluminum. In some embodiments, the mixture improves electron injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of less than several hundred ohms per unit area. In some embodiments, the thickness of the aforementioned cathode is 10 nm to 5 μm. In some embodiments, the thickness of the aforementioned cathode is 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent element is transparent or translucent to allow radiated light to pass through. In some embodiments, transparent or translucent electroluminescent elements enhance the brightness of light radiation. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with a transparent material that exhibits conductivity relative to the aforementioned anode. In some embodiments, the element includes both an anode and a cathode, but both are transparent or translucent.

[0162] Injection layer: The injection layer is the layer between the electrode and the organic layer. In some embodiments, the aforementioned injection layer reduces the driving voltage and enhances the light radiation brightness. In some embodiments, the aforementioned injection layer includes a hole injection layer and an electron injection layer. The aforementioned injection layer can be disposed 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 not present. Below are examples of preferred compounds that can be used as hole injection materials.

[0163] [Chemical Formula 88]

[0164] Next, examples of preferred compounds that can be used as electron injection materials will be given. [Chemical Formula 89]

[0165] Barrier layer: A barrier layer is a layer capable of preventing the diffusion of charges (electrons or holes) and / or excitons present in the luminescent layer to the outside of the luminescent layer. In some embodiments, an electron barrier layer exists between the luminescent layer and the hole transport layer to prevent electrons from passing through the luminescent layer to reach the hole transport layer. In some embodiments, a hole barrier layer exists between the luminescent layer and the electron transport layer to prevent holes from passing through the luminescent layer to reach the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing to the outside of the luminescent layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. The terms "electron barrier layer" or "exciton barrier layer" as used in this specification include layers that have both the functions of an electron barrier layer and an exciton barrier layer.

[0166] Cavity 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 rebonding between electrons and holes in the light-emitting layer. The material used in the hole barrier layer can be the same material as that described for the electron transport layer. Below are examples of preferred compounds that can be used in hole barrier layers.

[0167] [Chemical Formula 90]

[0168] Electron barrier layer: An electron barrier layer transports holes. In some embodiments, the electron barrier layer prevents electrons from reaching the hole transport layer during hole transport. In some embodiments, the electron barrier layer increases the probability of rebonding between electrons and holes in the light-emitting layer. The material used in the electron barrier layer can be the same material as that described for the hole transport layer. Compounds that can be used as electron barrier materials can be exemplified by compounds represented by the following general formulas. [Chemical Formula 91] In the above general formula, Ar 11 to Ar 13 independently represent substituted or unsubstituted aryl groups. Examples include substituted or unsubstituted phenyl groups, substituted or unsubstituted naphth-1-yl groups, and substituted or unsubstituted naphth-2-yl groups. Substituents for the hydrogen atom of the aryl group can be selected from one or more atoms or groups selected from the group consisting of deuterium, alkyl, and aryl groups. Examples include 4-biphenyl, 3-biphenyl, and meta-triphenyl-5'-yl groups. Specific examples of compounds represented by the above general formula are shown below. [Chemical Formula 92] Below are specific examples of preferred compounds that can be used as electron barrier materials.

[0169] [Chemical Formula 93]

[0170] Exciton barrier layer: An exciton barrier layer prevents excitons generated by the rebonding of holes and electrons in the emitting layer from diffusing to the electron transport layer. In some embodiments, the exciton barrier layer effectively confines excitons in the emitting layer. In some embodiments, this improves the optical radiation efficiency of the device. In some embodiments, the exciton barrier layer is adjacent to the emitting layer on either the anode or cathode side, and to the emitting layers on both sides thereof. In some embodiments, when the exciton barrier layer is present on the anode side, it can exist between the hole transport layer and the emitting layer, and be adjacent to the emitting layer. In some embodiments, when the exciton barrier layer is present on the cathode side, it can exist between the emitting layer and the cathode, and be adjacent to the emitting layer. In some embodiments, a hole injection layer, an electron barrier layer, or the same layer exist between the anode and the exciton barrier layer adjacent to the emitting layer on the anode side. In some embodiments, a hole injection layer, an electron barrier layer, a hole barrier layer, or the same layer exist between the cathode and the exciton barrier layer adjacent to the cathode-side luminescent layer. In some embodiments, the exciton barrier layer contains 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.

[0171] Hole transport layer: The hole transport layer contains hole transport material. In some embodiments, the hole transport layer is a single layer. In other embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material possesses one of the properties of hole injection or transport 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 this invention are not limited, but examples include triazole derivatives, acediazole inducers, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane inducers, pyrazoline derivatives, pyrazolineone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, aceazole derivatives, styrene-anthracene inducers, genistein derivatives, hydrazone derivatives, styrene derivatives, silazane derivatives, aniline copolymers, and conductive polymeric oligomers (especially thiophene oligomers) or combinations thereof. In some embodiments, the hole transport material can be selected from porphyrin compounds, aromatic tertiary amine compounds, and styrene-amine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Below are specific examples of preferred compounds that can be used as hole transport materials.

[0172] [Chemical Formula 94]

[0173] Electron transport layer: The electron transport layer comprises electron transport material. In some embodiments, the electron transport layer is a single layer. In other 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 this invention are not limited, but examples include nitro-substituted thiadiazole derivatives, dibenzoquinone derivatives, thiamethane dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinone dimethane, anthrone derivatives, thiadiazole derivatives, azole derivatives, thiamethane derivatives, or combinations thereof or polymers thereof. In some embodiments, the electron transport material is a thiadiazole inducer or a quinoline 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 given below.

[0174] [Chemical Formula 95]

[0175] Furthermore, examples of preferred compounds that can be added to the various organic layers are given. For instance, they can be considered as stabilizing materials.

[0176] [Chemical Formula 96]

[0177] Preferred materials that can be used in organic electroluminescent devices are specifically illustrated, but the materials that can be used in this invention are not limited to the following exemplary compounds. Furthermore, even compounds illustrated as materials with specific functions can be adapted to materials with other functions.

[0178] device: In some embodiments, the light-emitting layer is incorporated into the device. For example, the device includes OLED valves, OLED lamps, television displays, computer monitors, mobile phones, and tablets, but is not limited to these. In some embodiments, the electronic device includes an OLED having at least one organic layer comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode. In some embodiments, the structures described in this specification can be incorporated into various photosensitive or photoactivated devices such as OLEDs or optoelectronic devices. In some embodiments, the aforementioned structures can be used to facilitate charge transfer or energy transfer within the device and / or serve as hole transport materials. Examples of such devices include, for instance, 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 detection devices, organic photosensors, organic field-quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0179] Valve or lamp: In some embodiments, the electronic device includes an OLED having at least one organic layer comprising an anode, a cathode, and 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 a combination of OLEDs. In some embodiments, the aforementioned combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the aforementioned combination of OLEDs is a combination of colors that are neither red, green, nor blue (e.g., orange and yellow-green). In some embodiments, the aforementioned combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is an OLED lamp, which has: The circuit board has a first side having a mounting surface and a second side opposite to the first side, and is divided into at least one opening; At least one OLED, which is at least one OLED on the aforementioned mounting surface, the at least one OLED includes at least one organic layer comprising an anode, a cathode and a light-emitting layer between the anode and the cathode, and has a light-emitting structure; Circuit board housing; and At least one connector is disposed at the end of the aforementioned housing, and the aforementioned housing and the aforementioned connector are configured to be mounted on a lighting device. In some embodiments, the aforementioned OLED lamp has a plurality of OLEDs mounted on a circuit board to radiate light in a plurality of directions. In some embodiments, a portion of the light emitted in a first direction is polarized and radiated in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0180] Monitor 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 of the present invention is not limited, but is deposited on a substrate using steps such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the aforementioned substrate is a photographic plate structure used in the double-sided etching of pixels with a unique aspect ratio. The aforementioned screen (and, also referred to as a mask) can be used in the manufacturing process of an OLED display. By designing a corresponding original pattern, very steep narrow connecting rods between pixels can be arranged in the vertical direction and large-scale inclined openings can be arranged in the horizontal direction. This allows for the formation of a fine pattern of pixels required for a high-resolution display while optimizing the chemical vapor deposition on the TFT backplane. By patterning the internal structure of pixels, three-dimensional pixel openings with various aspect ratios can be formed in both the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within the pixel region protects the etching of specific areas until these specific patterns are undercut and removed from the substrate. At this point, all pixel regions are processed at the same etching rate, but their depth varies depending on the halftone pattern. By changing the size and spacing of the halftone patterns, etching with varying protection rates within the pixels can be performed, enabling localized deep etching required to create steep vertical slopes. The preferred material for vapor deposition masks is inert steel. Inert steel is a thin sheet metal alloy that is cold-rolled and grown in a steel mill. Inert steel cannot be used as a nickel mask for electrodeposition onto a rotating mandrel. A suitable and low-cost method for forming opening areas within the vapor deposition mask is a wet chemical etching method. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is processed using lithography (e.g., photolithography and electron beam lithography). In some embodiments, the screen or display pattern is processed using wet chemical etching. In yet another embodiment, the screen or display pattern is processed using plasma etching.

[0181] Manufacturing method of the device: Regarding OLED displays, a large motherboard is typically formed, and then the motherboard is cut into unit panels for manufacturing. Typically, each unit panel on the motherboard is formed by: forming a thin-film transistor (TFT) with an active layer and source / drain electrodes on a substrate; coating a planarization film on the TFT to sequentially form a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer; and then cutting from the motherboard. Regarding OLED displays, a large motherboard is typically formed, and then the motherboard is cut into unit panels for manufacturing. Typically, each unit panel on the motherboard is formed by: forming a thin-film transistor (TFT) with an active layer and source / drain electrodes on a substrate; coating a planarization film on the TFT to sequentially form a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer; and then cutting from the motherboard.

[0182] In other embodiments of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising: The step of forming a barrier layer on the substrate of the motherboard; The step of forming a plurality of display units on the aforementioned barrier layer in the form of unit panel units; The steps of forming an encapsulation layer on each of the display units of the aforementioned unit panel; and The step of coating an organic thin film on the interface between the aforementioned unit panels. In some embodiments, the barrier layer is, for example, an inorganic thin film formed of SiNx, and the ends of the barrier layer are covered with an organic thin film formed of polyimide or acrylic acid. In some embodiments, the organic thin film auxiliary motherboard is soft-cut in unit panel units. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have a TFT layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film. The organic thin film coated on the aforementioned interface 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 aforementioned light-emitting unit is connected to the TFT layer via a passivation layer, the planarization film between them, and an encapsulation layer covering and protecting the light-emitting unit. In some embodiments of the aforementioned manufacturing method, the aforementioned organic thin film is not connected to the display unit, nor is it connected to the encapsulation layer.

[0183] The aforementioned organic thin film and planarization film may each comprise either polyimide or acrylic acid. In some embodiments, the aforementioned barrier layer may be an inorganic thin film. In some embodiments, the aforementioned substrate may be formed of polyimide. The aforementioned method may further include the steps of mounting a carrier substrate formed of glass material on another surface of the substrate before forming the barrier layer on one surface of the substrate formed of polyimide, and separating the aforementioned carrier substrate from the substrate before cutting along the interface. In some embodiments, the aforementioned OLED display is a flexible display. In some embodiments, the aforementioned passivation layer is an organic thin film disposed on the TFT layer to cover the TFT layer. In some embodiments, the aforementioned planarization film is an organic thin film formed on the passivation layer. In some embodiments, similar to the organic thin film formed at the end of the barrier layer, the aforementioned planarization film is formed of polyimide or acrylic acid. In some embodiments, the aforementioned planarization film and organic thin film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the aforementioned organic thin film may be formed at the end of the barrier layer, whereby a portion of the organic thin film directly contacts the substrate, while the remaining portion of the organic thin film, while surrounding the end of the barrier layer, contacts the barrier layer.

[0184] In some embodiments, the aforementioned light-emitting layer has 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 aforementioned pixel electrode is connected to the source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, thereby causing the organic light-emitting layer to radiate light and form an image. Hereinafter, the image forming unit having a TFT layer and light-emitting units 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 can be formed as a thin-film encapsulation structure consisting of alternating layers of organic and inorganic thin films. In some embodiments, the aforementioned encapsulation layer has a thin-film encapsulation structure consisting of multiple layers of thin films. In some embodiments, the organic thin film coated on the interface is spaced apart from each of the plurality of display units. In some embodiments, the aforementioned organic thin film is formed in such a manner that a portion of the organic thin film is in direct contact with the substrate, while the remaining portion of the organic thin film, while surrounding the end of the barrier layer, is in contact with the barrier layer.

[0185] In one embodiment, the OLED display is flexible and uses a soft substrate made of polyimide. In some embodiments, the aforementioned 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 on the opposite side of the carrier substrate. In one embodiment, the barrier layer is patterned according to the dimensions of each unit panel. For example, while the base substrate is formed on all surfaces of the motherboard, the barrier layer is formed according to the dimensions of each unit panel, thereby forming grooves at the interfaces between the barrier layers of the unit panels. Each unit panel can be cut along the aforementioned grooves.

[0186] In some embodiments, the aforementioned manufacturing method further includes a step of cutting along the interface, wherein a groove is formed on the barrier layer, and at least a portion of the organic thin film is formed in the groove, the groove not penetrating into the substrate. In some embodiments, the TFT layer forming each unit panel is covered by a passivation layer as an inorganic thin film and a planarization film as an organic thin film. For example, while forming a planarization film made of polyimide or acrylic, the groove at the interface is covered, for example, by an organic thin film made of polyimide or acrylic. This prevents cracking caused by absorbing the impact generated when each unit panel is cut along the groove at the interface. That is, when all barrier layers are completely exposed due to the absence of an organic thin film, the impact generated when each unit panel is cut along the groove at the interface is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic thin film to absorb impacts that could be transmitted to the barrier layers in the absence of the organic thin film. This allows for soft cutting of each unit panel to prevent cracking within the barrier layers. In another embodiment, the organic thin film covering the grooves at the interface and the planarization film are spaced apart from each other. For example, if the organic thin film and the planarization film are bonded together as a single layer, external moisture may seep into the display unit through residual portions of the planarization film and the organic thin film. Therefore, the organic thin film and the planarization film are spaced apart from each other to ensure that the organic thin film is spaced apart from the display unit.

[0187] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover it. In this way, after the motherboard is completely manufactured, the carrier substrate supporting the substrate is separated from the substrate. In some embodiments, if a laser beam is radiated onto the carrier substrate, the carrier substrate separates from the substrate due to the difference in thermal expansion coefficients between the carrier substrate and the substrate. In some embodiments, the motherboard is cut in unit panels. In some embodiments, the motherboard is cut along the interface between unit panels using a cutter. In some embodiments, the grooves along the cut interface of the motherboard are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting. In some implementations, the aforementioned methods reduce product defect rates and stabilize product quality. Other forms include OLED displays, which have a barrier layer formed on a substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic thin film coated on the ends of the barrier layer. [Example]

[0188] The features of the present invention will be further described in detail below with examples of synthesis and embodiments. Regarding the materials, processing contents, processing steps, etc., shown below, appropriate modifications can be made without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below. Furthermore, the evaluation of luminescence properties was performed using a source meter (TEKTRONIX, INC.: 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd.: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Photonics: USB2000), a spectroradiometer (TOPCON CORPORATION: SR-3), and a stripe photograph (Hamamatsu Photonics KK: C4334 type). The determination of orientation values ​​was performed using a (Hamamatsu Photonics KK molecular orientation characteristic measuring device C14234-01).

[0189] (Synthetic Example 1) Synthesis of Compound 1 [Chemical Formula 97]

[0190] Under a nitrogen stream, carbazole (7.69 g, 46.0 mmol) was added to a solution of sodium hydride (1.16 g, 29.0 mmol) in N,N-dimethylformamide (160 mL). After stirring at room temperature for 30 minutes, 2,5-dibromo-1,4-difluorobenzene (5.00 g, 18.4 mmol) was added, and the mixture was stirred at 60 °C for 16 hours. The mixture was returned to room temperature, and water was added to filter the precipitated solid. The solid was purified by silicone column chromatography (toluene), and the obtained solid was washed with acetonitrile to give intermediate A (5.83 g, 10.3 mmol, 56% yield) as a white solid. 1HNMR(400MHz, CDCl 3, δ):8.19(d, J=8.0Hz,4H),8.01(s,2H),7.58-7.48(m,4H),7.39-7.35(m,4H),7.27-7.24(m,4H) MS(ASAP):567.01(M+H +).Calcd for.C 30H 18Br 2N 2:565.98

[0191] [Chemical Formula 98]

[0192] Under a nitrogen stream, 4.5 mL of 1.6 mol / L hexane solution (7.19 mmol) was added to 100 mL of a toluene solution of intermediate A (1.00 g, 1.80 mmol) at -30 °C, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to -30 °C, and 0.991 g of boron tribromide (3.96 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (0.558 g, 3.60 mmol) was added to the reaction mixture, and the mixture was stirred at 120 °C for 17 hours. The reaction mixture was cooled to room temperature, and 5.4 mL of 2-trimethylmethylmagnesium bromide (5.40 mmol) of 1.0 mol / L tetrahydrofuran solution was added, and the mixture was stirred at room temperature for 2.5 hours. The solvent in the resulting reaction mixture was removed by distillation, and methanol was added to filter out the precipitate. The solid was purified by silicone column chromatography (toluene:hexane = 4:6) to obtain compound 1 (0.258 g, 0.388 mmol, 22% yield) as an orange solid. 1HNMR (400MHz, CDCl 3, δ): 9.26 (s, 2H), 8.52 (d, J=6.8Hz,2H),8.28-8.21(m,4H),7.94-7.90(m,2H),7.64-7.60(m,2H),7.45-7.42(m,4H),7.15-7.14(m,4H),2.56(s,6H),2.16(s,12H) MS(ASAP):664.23(M +).Calcd for.C 48H 38B 2N 2:664.32

[0193] (Synthetic Example 2) Synthesis of Compound 2 [Chemical Formula 99]

[0194] Under a nitrogen stream, 3,6-diphenylcarbazole (3.00 g, 9.39 mmol) was added to a solution of sodium hydride (0.376 g, 9.39 mmol) in N,N-dimethylformamide (70 mL). After stirring at room temperature for 30 minutes, 2,5-dibromo-1,4-difluorobenzene (1.02 g, 3.76 mmol) was added, and the mixture was stirred at 60 °C for 14 hours. The mixture was returned to room temperature, and water and methanol were added to filter the precipitated solid. The solid was dissolved in hot toluene, filtered through a silicone gel pad (toluene), and the solvent in the filtrate was removed by distillation. The obtained solid was washed with acetonitrile to give intermediate B (2.36 g, 2.71 mmol, 72% yield) as a white solid. 1HNMR (400MHz, CDCl 3, δ):8.46-8.44(m,4H),8.10(s,2H),7.79-7.75(m,12H),7.54-7.49(m,8H),7.41-7.35(m,8H) MS(ASAP):870.20(M +).Calcd for.C 54H 34Br 2N 2:870.11

[0195] [Chemical Formula 100]

[0196] Under a nitrogen stream, 2.9 mL of 1.6 mol / L hexane solution (4.60 mmol) was added to 300 mL of a toluene solution of intermediate B (1.00 g, 1.15 mmol) at -30 °C, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to -30 °C, and 0.633 g of boron tribromide (2.53 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (0.357 g, 2.30 mmol) was added to the reaction mixture, and the mixture was stirred at 120 °C for 17 hours. The reaction mixture was cooled to room temperature, and 3.4 mL of 2-trimethylmethylmagnesium bromide (3.40 mmol) of 1.0 mol / L tetrahydrofuran solution was added, and the mixture was stirred at room temperature for 4 hours. The resulting reaction mixture was filtered through a silicone mat (toluene), and the solvent in the filtrate was removed by distillation. Ethyl acetate was added to the obtained viscous body to filter the precipitate, thereby obtaining compound 2 as an orange solid (0.0710 g, 0.0732 mmol, yield 6%). 1HNMR (400MHz, CDCl 3, δ):9.29(s,2H),8.81-8.79(m,2H),8.53-8.52(m,2H),8.46-8.45(m,2H),7.82 -7.78(m,8H),7.59-7.36(m,14H),7.20-7.18(m,4H),2.59(s,6H),2.22(s,12H) MS(ASAP):968.67(M +).Calcd for.C 72H 54B 2N 2:968.45

[0197] (Synthetic Example 3) Synthesis of Compound 3 [Chemical Formula 101]

[0198] Intermediate C A solution (360 mL) of 3,6-di-tributyl-9H-carbazole (29.2 g, 105 mmol), cesium carbonate (61.9 g, 190 mmol), and 2,5-dibromo-1,4-difluorobenzene (12.9 g, 47.5 mmol) in N,N-dimethylformamide was stirred at 120 °C for 17 hours under a nitrogen atmosphere. The mixture was returned to room temperature, and water was added to filter the precipitated solid. The solid was purified by silica gel column chromatography (toluene), and recrystallized from the solid by toluene / methanol to give intermediate C (17.5 g, 22.1 mmol, 47% yield) as a white solid. 1HNMR (400MHz, CDCl 3, δ):8.2-8.17(m,4H),7.93(s,2H),7.55-7.52(m,4H),7.17(d, J=8.4Hz,4H),1.49(s,36H) MS(ASAP):791.47(M+H +).Calcd for.C 46H 50Br 2N 2:790.23

[0199] [Chemical Formula 102]

[0200] Compound 3 [] Under a nitrogen stream, n-BuLi (n-Butyllithium: n-butyllithium) (1.6 mol / L hexane solution, 4.7 mL, 7.56 mmol) was added to a toluene solution (100 mL) of intermediate C (2.00 g, 2.52 mmol) at -30 °C, and the mixture was stirred at 50 °C for 30 min. The reaction mixture was cooled to -30 °C, boron tribromide (3.16 g, 12.6 mmol) was added, and the mixture was stirred at room temperature for 30 min. 1,2,2,6,6-pentamethylpiperidine (1.96 g, 12.6 mmol) was added to the reaction mixture, and the mixture was stirred at 130 °C for 2 h. 2-Trimethylmethylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 25.2 mL, 25.2 mmol) was added to the reaction mixture, and the mixture was stirred while returning to room temperature for 17 h. The solvent in the resulting reaction mixture was removed by distillation, and methanol was added to filter out the precipitate. The solid was purified by silicone column chromatography (toluene:hexane = 1:9) to obtain compound 3 (0.292 g, 0.328 mmol, 13% yield) as an orange solid. 1HNMR (400MHz, CDCl 3, δ):9.11(s,2H),8.58(d, J=2.0Hz,2H),8.25(d, J=2.0Hz,2H),8.23(d, J=1.6Hz,2H),7.75(d, J=9.2Hz,2H),7.44-7.41(m,2H),7.17(s,4H),2.60(s,6H),2.16(s,12H),1.53-1.51(m,36H) MS(ASAP):888.85(M +).Calcd for.C 64H 70B 2N 2:888.57

[0201] (Synthetic Example 4) Synthesis of Compound 4 [Chemical Formula 103]

[0202] Compound 4 Under a nitrogen stream, a solution (20 mL) of compound 3 (250 mg, 0.281 mmol) and N-bromosuccinimide (99.6 mg, 0.562 mmol) in N,N-dimethylformamide was stirred at room temperature for 16 hours. Water was added to the mixture to filter the precipitated solid. The solid was purified by silicone column chromatography to obtain compound 4 as an orange solid.

[0203] (Synthetic Example 5) Synthesis of Compound 5 [Chemical Formula 104]

[0204] Compound 5 Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 0.13 mL, 0.201 mmol) was added to a tetrahydrofuran solution (10 mL) of compound 4 (100 mg, 0.0955 mmol) at -30 °C, and the mixture was stirred at room temperature for 30 minutes. Dimethylmalononitrile (27.0 mg, 0.287 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 16 hours. The solvent in the reaction mixture was removed by distillation, and the mixture was purified by silicone column chromatography to obtain compound 5 as a red solid.

[0205] (Synthetic Example 6) Synthesis of Compound 6 [Chemical Formula 105]

[0206] Compound 6 Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 4.7 mL, 7.56 mmol) was added to a toluene solution (100 mL) of intermediate C (2.00 g, 2.53 mmol) at 0 °C, and the mixture was stirred at 50 °C for 30 min. The reaction mixture was cooled to 0 °C, boron tribromide (3.16 g, 12.6 mmol) was added, and the mixture was stirred at room temperature for 30 min. 1,2,2,6,6-pentamethylpiperidine (1.96 g, 12.6 mmol) was added to the reaction mixture, and the mixture was stirred at 135 °C for 2 h. 2,4,6-triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 25.2 mL, 25.2 mmol) was added to the reaction mixture, and the mixture was stirred while returning to room temperature for 17 h. The solvent in the resulting reaction mixture was removed by distillation, and methanol was added to filter out the precipitate. The solid was purified by silicone column chromatography (toluene:hexane = 1:49) and recrystallized with toluene / methanol to obtain compound 6 (0.140 g, 0.328 mmol, 5% yield) as an orange solid. 1HNMR (400MHz, CDCl 3, δ): 9.10 (s, 2H), 8.53 (d, J=1.6Hz, 2H), 8.27 (d, J=1.6Hz, 2H), 8.21 (d, J=1.6Hz, 2H), 7.64 (d, J=8.8Hz, 2H), 7.36 (dd, J=8.8,1.6Hz,2H),7.27(s,4H),3.17(sept, J=6.8Hz,2H),2.55(sept, J=6.8Hz,4H),1.55(d, J=6.8Hz,12H),1.48(s,18H),1.47(s,18H),1.06(d, J=6.8Hz,12H),1.01(d, J=6.8Hz,12H). MS(MALDI):1058.07(M +).Calcd for.C 76H 96B 2N 2:1058.78

[0207] (Synthetic Example 7) Synthesis of Compounds 7 and 8 [Chemical Formula 106]

[0208] Intermediate D A solution (50 mL) of 3-tert-butyl-9H-carbazole (1.8 g, 8.06 mmol), potassium carbonate (1.78 g, 12.9 mmol), and 2,5-dibromo-1,4-difluorobenzene (0.876 g, 3.22 mmol) in N,N-dimethylformamide was stirred at 120 °C for 17 hours under a nitrogen stream. The mixture was returned to room temperature, and water was added to filter the precipitated solid. The solid was purified by silicone column chromatography (chloroform:hexane = 1:4) to give intermediate D (0.44 g, 0.650 mmol, 20% yield) as a white solid. 1HNMR(400MHz, CDCl 3, δ):8.2-8.18(m,4H),7.97(s,2H),7.56(d, J=8.4Hz,2H),7.48(t, J=8.4Hz,2H),7.35(t, J=8.4Hz,2H),7.25-7.18(m,6H),1.49(s,18H) MS(ASAP):679.28(M+H +).Calcd for.C 38H 34Br 2N 2:678.11 [Chemical Formula 107]

[0209] Compounds 7,8 Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 5.23 mL, 8.37 mmol) was added to a toluene solution (100 mL) of intermediate D (1.90 g, 2.79 mmol) at -30 °C, and the mixture was stirred at 50 °C for 30 min. The reaction mixture was cooled to -30 °C, boron tribromide (3.49 g, 14.0 mmol) was added, and the mixture was stirred at room temperature for 30 min. 1,2,2,6,6-pentamethylpiperidine (2.17 g, 14.0 mmol) was added to the reaction mixture, and the mixture was stirred at 135 °C for 2 h. 2-Mestriylmethylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 27.9 mL, 27.9 mmol) was added to the reaction mixture, and the mixture was stirred while returning to room temperature for 17 h. The solvent in the resulting reaction mixture was removed by distillation, and methanol was added to filter out the precipitate. The solid was purified by silicone column chromatography (toluene:hexane = 1:9) to obtain compound 7 (0.243 g, 0.313 mmol, yield 11%) and compound 8 (0.313 g, 0.403 mmol, yield 14%), both in orange form. Compound 7 1H NMR (400MHz, CDCl 3, δ): 9.21 (s, 2H), 8.52 (dd, J=9.5, 2.0Hz, 2H), 8.25 (d, J=2.0Hz, 2H), 8.20 (dd, J=9.5, 2.0Hz, 2H), 7.81 (d, J=11.5Hz,2H),7.60(t, J=9.5Hz,2H),7.44(dd, J=11.5,9.0Hz,2H),7.16(s,4H),2.57(s,6H),2.15(s,12H),1.51(s,18H) MS(MALDI):776.90(M +).Calcd for.C 56H 54B 2N 2:776.45 Compound 8 1H NMR (400MHz, CDCl 3, δ):9.21(s,1H),9.16(s,1H),8.58(d, J=2.0Hz,1H),8.52(d, J=7.6Hz,1H),8.3-8.24(m,3H),8.19(d, J=7.2Hz,1H),7.92-7.85(m,1H),7.82-7.75(m,1H),7.60(t, J=7.2Hz,1H),7.47-7.39(m,3H),7.19-7.13(m,4H),2.6-2.55(m,6H),2.17-2.14(m,12H),1.51(s,18H) MS(MALDI):776.98(M +).Calcd for.C 56H 54B 2N 2:776.45

[0210] (Synthetic Example 8) Synthesis of Compound 9 [Chemical Formula 108]

[0211] Compound 9 Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 3.3 mL, 5.30 mmol) was added to a toluene solution (100 mL) of intermediate A (1.00 g, 1.77 mmol) at -30 °C, and the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to -30 °C, boron tribromide (2.21 g, 8.83 mmol) was added, and the mixture was stirred at room temperature for 30 min. 1,2,2,6,6-pentamethylpiperidine (1.37 g, 8.83 mmol) was added to the reaction mixture, and the mixture was stirred at 120 °C for 15 h. The reaction mixture was returned to room temperature, and 2,4,6-triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 17.7 mL, 17.7 mmol) was added, and the mixture was stirred at 120 °C for 4 h. The resulting reaction mixture was filtered, and the solvent in the filtrate was removed by distillation. The residue was purified by silicone column chromatography (toluene:hexane = 15:85) to obtain compound 9 as an orange solid (0.128 g, 0.154 mmol, yield 9%). 1H NMR (400MHz, CDCl 3, δ): 9.31 (s, 2H), 8.49 (d, J=7.2Hz, 2H), 8.28 (d, J=7.2Hz, 2H), 8.25 (d, J=7.6Hz, 2H), 7.85 (d, J=8.4Hz, 2H), 7.61 (t, J=7.6Hz,2H),7.41(t, J=7.6Hz,2H),7.38-7.33(m,2H),7.28(s,4H),3.16(sept, J=6.8Hz,2H),2.57(sept, J=6.8Hz,4H),1.52(d, J=7.2Hz,12H),1.09(d, J=6.8Hz,12H),1.04(d, J=6.8Hz,12H) MS(MALDI):832.73(M +).Calcd for.C 60H 62B 2N 2:832.51

[0212] (Synthetic Example 9) Synthesis of Compound 10 [Chemical Formula 109]

[0213] Intermediate E A solution (50 mL) of 3-tributyl-6-phenyl-9H-carbazole (2.70 g, 9.02 mmol), cesium carbonate (5.34 g, 16.4 mmol), and 2,5-dibromo-1,4-difluorobenzene (1.11 g, 4.10 mmol) in N,N-dimethylformamide was stirred at 120 °C for 15 hours under a nitrogen atmosphere. The mixture was returned to room temperature, and water was added to filter out the precipitated solid. Recrystallization with toluene yielded intermediate E (3.06 g, 3.68 mmol, 90% yield), a white solid. 1HNMR (400MHz, CDCl 3, δ): 8.40 (d, J=2.0Hz, 2H), 8.23 ​​(d, J=1.6Hz, 2H), 8.02 (s, 2H), 7.79-7.76 (m, 4H), 7.73 (dd, J=8.8, 1.6Hz, 2H), 7.59 (dd, J=8.4,1.6Hz,2H),7.53-7.48(m,4H),7.41-7.35(m,2H),7.31(d, J=7.6Hz,2H),7.23(d, J=8.8Hz,2H),1.50(s,18H) MS(ASAP):831.43(M+H +).Calcd for.C 50H 42Br 2N 2:830.17 [Chemical Formula 110]

[0214] Compound 10 Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 2.27 mL, 3.63 mmol) was added to a toluene solution (100 mL) of intermediate E (1.00 g, 1.21 mmol) at -30 °C, and the mixture was stirred at 50 °C for 30 min. The reaction mixture was cooled to -30 °C, boron tribromide (1.52 g, 6.05 mmol) was added, and the mixture was stirred at room temperature for 30 min. 1,2,2,6,6-pentamethylpiperidine (0.939 g, 6.05 mmol) was added to the reaction mixture, and the mixture was stirred at 135 °C for 2 h. 2,4,6-triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 12.1 mL, 12.1 mmol) was added to the reaction mixture, and the mixture was stirred while returning to room temperature for 17 h. The solvent in the resulting reaction mixture was removed by distillation, and methanol was added to filter out the precipitate. The solid was purified by silicone column chromatography (toluene:hexane = 1:9) and recrystallized with toluene / methanol to obtain compound 10 (0.364 g, 0.332 mmol, yield 27%) as an orange solid. 1H NMR (400MHz, CDCl 3, δ):9.24-9.19(m,2H),8.62-8.60(m,2H),8.50-8.47(m,2H),8.35-8.32(m,2H),7.85-7.69(m,6H),7.64-7.60(m,2H),7.56-7.46(m,4 H),7.45-7.35(m,2H),7.31(s,4H),3.23-3.16(m,2H),2.65-2.56(m,4H),1.60-1.55(m,18H),1.51-1.48(m,12H),1.14-1.02(m,24H) MS(MALDI):1098.09(M+H +).Calcd for.C 80H 86B 2N 2:1096.70 Furthermore, the compounds synthesized in the synthetic examples, after sublimation purification, are used for the following purposes.

[0215] (Example 1) Fabrication of the thin film By vacuum evaporation, the luminescent materials and the host materials listed in Table 3 were deposited on a quartz substrate from different evaporation sources under vacuum conditions of less than 1×10⁻³ Pa, thereby forming a thin film with a thickness of 100 nm. The content of the luminescent material was set at 30% by mass. The results of measuring the orientation value S of the luminescent material of each formed thin film, together with the dipole moment of each luminescent material, are shown in Table 3. It was confirmed that the orientation of the luminescent material represented by general formula (1) can be improved by using the host material represented by general formula (2). Furthermore, it was also confirmed that high orientation of the luminescent material can be achieved by using a host material with a dipole moment of less than 2.52.

[0216] (Example 2) Fabrication and Evaluation of Organic Electroluminescent Element Thin films were deposited on a glass substrate with an anode consisting of a 100 nm thick indium tin oxide (ITO) layer using vacuum evaporation at a vacuum level of 1 × 10⁻⁵ Pa. First, a 5 nm thick HATCN layer was formed on the ITO, followed by a 60 nm thick NPD layer, and then a 10 nm thick EBL1 layer. Next, the luminescent materials and host materials listed in Table 3 were co-deposited from different evaporation sources to form a 35 nm thick luminescent layer. The luminescent material content was set to 30% by mass. Then, SF₃-TRZ was formed to a thickness of 10 nm, and Liq and SF₃-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The Liq and SF₃-TRZ contents in this layer were set to 30% by mass and 70% by mass, respectively. Finally, Liq was formed to a thickness of 2 nm, and aluminum (Al) was deposited to a thickness of 100 nm to form a cathode, which was then used as an organic light-emitting diode (OLED). When each organic electroluminescent element was energized, luminescence was observed in all elements. The luminescence from the luminescent material within the luminescent layer was the highest. The external quantum efficiency (EQE) and driving voltage (VINT) at 6.3 mA / cm² were measured for each organic electroluminescent element, and the results are shown in Table 3. The organic electroluminescent elements (elements 1-9) of this invention all exhibit high EQE and low driving voltage, thus demonstrating superior performance.

[0217] [Table 3] Luminescent materials Main materials dipole moment S EQE(%) V INT(V) Comparator 1 Compare compound 1 mCBP 2.52 0 12.0 4.3 Comparator 2 Compound 6 mCBP 2.52 -0.32 15.9 4.2 Comparator 3 Compound 3 mCBP 2.52 -0.32 15.9 4.2 Component 1 Compound 6 Compound H1 1.16 -0.40 17.8 3.7 Component 2 Compound 6 compound H2 2.07 -0.38 17.2 3.5 Component 3 Compound 6 compound H3 2.17 -0.35 17.6 3.6 Component 4 Compound 6 Compound H4 0.63 -0.34 16.5 3.3 Component 5 Compound 6 Compound H5 1.84 -0.39 17.7 3.7 Component 6 Compound 6 Compound H6 1.61 -0.39 17.7 3.7 Component 7 Compound 6 Compound H7 0.97 -0.39 17.6 3.7 Component 8 Compound 6 Compound H8 1.94 -0.38 17.4 3.6 Component 9 Compound 6 Compound H9 0.73 -0.33 16.3 3.7

[0218] [Chemical Formula 111] [Industrial Applicability]

[0219] In the film of this invention, the luminescent material exhibits excellent orientation and can be better used in organic light-emitting elements. Furthermore, the organic light-emitting element of this invention has a low driving voltage and high luminous efficiency, thus having high industrial applicability.

Claims

1. An organic light-emitting element comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2), wherein in general formula (1), X1 is a nitrogen atom, X2 is a boron atom, R1 to R26, A1 and A2 independently represent hydrogen atoms, deuterium atoms or substituents, and 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, R1 R16 and R17, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 can bond with each other to form a ring structure. A1 and R12, A1 and R13, A2 and R1, and A2 and R26 do not bond with each other to form a ring structure. R17 and R18 bond with each other to form a single bond, thus forming a pyrrole ring. When R7 and R8 are bonded together, a single bond is formed, -B(R32)-, -CO- or -CS-, where R32 is a hydrogen atom, a deuterium atom or a substituent. In general formula (2), X11 represents O, S or C(RB) (RC), A11 and A12 are respectively independently benzene ring, furan ring, thiol ring, pyrrole ring or cyclopentadiene ring, which may be further condensed with other rings or substituted, R111 to R114, RB, and RC respectively independently represent hydrogen atom, deuterium atom, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group or cyano group, and R115 respectively independently represent hydrogen atom, deuterium atom, Substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or cyano, R111 and R112, R112 and R113, R113 and R114, two adjacent R115, and RB and RC can bond to each other to form a cyclic structure, n represents 3, L represents a single bond, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a linking group formed by two or more of these bonds, and L is bonded to a benzene ring bonded with (R115)n.

2. The organic light-emitting element as claimed in claim 1, wherein R3 and R6 in general formula (1) are substituents.

3. The organic light-emitting element as claimed in claim 1, wherein R8 and R12 in general formula (1) are substituents.

4. The organic light-emitting element as claimed in claim 1, wherein groups 1 to 6 of general formula (1) are bonded to each other to form a benzofuran ring or a benzothiophene ring.

5. An organic light-emitting element as described in any one of claims 1 to 4, wherein the compound represented by general formula (1) has a rotationally symmetric structure.

6. The organic light-emitting element as claimed in claim 1, wherein the compound represented by general formula (1) has any one of the following structures.

7. An organic light-emitting element as claimed in any one of claims 1 to 4, wherein the group of general formula (2) bonded to the right side of L comprises a dibenzofuran structure.

8. An organic light-emitting element as described in any one of claims 1 to 4, wherein L in general formula (2) is methylphenyl.

9. An organic light-emitting element as described in any one of claims 1 to 4, wherein the dipole moment of the compound represented by general formula (2) is less than 2.

52.

10. A membrane comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2), wherein in general formula (1), X1 is a nitrogen atom, X2 is a boron atom, R1 to R26, A1 and A2 independently represent hydrogen atoms, deuterium atoms or substituents, and 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, R1 R16 and R17, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 can bond with each other to form a ring structure. A1 and R12, A1 and R13, A2 and R1, and A2 and R26 do not bond with each other to form a ring structure. R17 and R18 bond with each other to form a single bond, thus forming a pyrrole ring. When R7 and R8 are bonded together, a single bond is formed, -B(R32)-, -CO- or -CS-, where R32 is a hydrogen atom, a deuterium atom or a substituent. In general formula (2), X11 represents O, S or C(RB) (RC), A11 and A12 are respectively independently benzene ring, furan ring, thiol ring, pyrrole ring or cyclopentadiene ring, which may be further condensed with other rings or substituted, R111 to R114, RB, and RC respectively independently represent hydrogen atom, deuterium atom, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group or cyano group, and R115 respectively independently represent hydrogen atom, deuterium atom, Substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or cyano, R111 and R112, R112 and R113, R113 and R114, two adjacent R115, and RB and RC can bond to each other to form a cyclic structure, n represents 3, L represents a single bond, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a linking group formed by two or more of these bonds, and L is bonded to a benzene ring bonded with (R115)n.

11. The membrane as claimed in claim 10, wherein the content of the compound represented by the aforementioned general formula (1) is less than that of the compound represented by the aforementioned general formula (2).