TW202317551A - Compound, composition, host material, electron barrier material and organic light emitting element - Google Patents

Abstract

An organic light emitting element which uses a compound represented by the general formula has high thermal stability and excellent light emission characteristics. Each of R1 to R7 represents a hydrogen atom, a deuterium atom, an alkyl group or an aryl group; and at least one of R1 to R4 represents an aryl group. Each of R8 to R19 represents a hydrogen atom, a deuterium atom or an alkyl group.

Description

Compound, composition, host material, electron barrier material and organic light-emitting device

The present invention relates to a compound useful as a host material, a composition using the compound, and an organic light-emitting device.

Actively conducting research to improve the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, various studies have been conducted to improve luminous efficiency by newly developing and combining electron transport materials, hole transport materials, luminescent materials, and host materials constituting organic electroluminescent devices. Among them, the development and utilization of organic electroluminescent elements using delayed fluorescent materials has attracted attention (see Non-Patent Document 1).

The delayed fluorescent material is a material that emits fluorescence when returning from the excited singlet state to the ground state after an inverse intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence from this pathway is observed more delayed than that from the excited singlet state directly from the ground state (normal fluorescence), and is therefore called delayed fluorescence. Among them, for example, in the case of exciting a luminescent compound by injecting carriers, the generation probability of an excited singlet state and an excited triplet state is statistically 25%:75%, so it is only determined by the fluorescence from the directly generated excited singlet state. There is a limit to improving luminous efficiency. On the other hand, in the delayed fluorescent material, in addition to the excited singlet state, the excited triplet state can also be used in fluorescent light through the above-mentioned inverse intersystem crossing path. Therefore, compared with ordinary fluorescent materials, Higher luminous efficiency can be obtained. The delayed fluorescent material with this characteristic is usually used together with the host material in the light-emitting layer of the organic electroluminescent element, which actually helps to improve the luminous efficiency.

[Non-Patent Document 1] Uoyama et al, Nature, 492, 234-238 (2012)

As the host material combined with the delayed fluorescent material, a compound whose lowest excited singlet energy is greater than that of the delayed fluorescent material is selected. However, even if a host material used in combination with a conventional fluorescent material that does not radiate delayed fluorescence is directly combined with a delayed fluorescent material, sufficiently high light-emitting performance cannot be achieved for practical use. In particular, there is room for improvement in the light-emitting performance of an organic electroluminescent device using a delayed fluorescent material when driven at a high temperature. Therefore, the inventors of the present invention have studied for the purpose of improving the light-emitting performance during high-temperature driving and improving the thermal stability in an organic light-emitting device using a delayed fluorescent material.

As a result of painstaking research, the present inventors found that as long as a compound with a specific structure and a delayed fluorescent material are used in combination in an organic light-emitting device, even under high-temperature driving, high luminous efficiency and low-voltage driving can be maintained. . This invention was made based on this knowledge, Specifically, it has the following structures.

[在通式（1）中，R ¹～R ⁷分別獨立地表示氫原子、氘原子、可以被氘化的烷基或者經取代或未經取代的芳基，R ¹～R ⁴中的至少一個為經取代或未經取代的芳基。R ⁸～R ¹⁹分別獨立地表示氫原子、氘原子或可以被氘化的烷基。] [2]如[1]所述之化合物，其中，R ¹～R ⁴中的僅一個為經取代或未經取代的芳基。 [3]如[1]或[2]所述之化合物，其中，R ²為經取代或未經取代的芳基。 [4]如[1]至[3]之任一項所述之化合物，其中，R ⁴為經取代或未經取代的芳基。 [5]如[1]至[4]之任一項所述之化合物，其中，前述經取代或未經取代的芳基為經取代或未經取代的苯基。 [6]如[1]至[5]之任一項所述之化合物，其中，前述經取代或未經取代的芳基為經取代或未經取代的二苯并呋喃基或者經取代或未經取代的二苯并噻吩基。 [7]如[1]至[6]之任一項所述之化合物，其中，R ⁵～R ¹¹分別獨立地為氫原子或氘原子。 [8]如[1]至[7]之任一項所述之化合物，其中，R ¹²～R ¹⁹分別獨立地為氫原子或氘原子。 [9]如[1]至[8]之任一項所述之化合物，其中，R ¹～R ⁴中的至少一個包含氘原子。 [10]如[1]至[9]之任一項所述之化合物，其中，R ¹²～R ¹⁹中的至少一個包含氘原子。 [11]一種主體材料，其係包含[1]至[10]之任一項所述之化合物。 [12]如[10]所述之主體材料，其係用於與延遲螢光材料一起使用。 [13]如[11]所述之主體材料，其係用於與下述通式（G）所表示之化合物一起使用。 通式（G） [化學式2]

[在通式（G）中，X ¹及X ²中的一者為氮原子，另一者為硼原子。R ¹～R ²⁶、A ¹、A ²分別獨立地表示氫原子、氘原子或取代基。R ¹和R ²、R ²和R ³、R ³和R ⁴、R ⁴和R ⁵、R ⁵和R ⁶、R ⁶和R ⁷、R ⁷和R ⁸、R ⁸和R ⁹、R ⁹和R ¹⁰、R ¹⁰和R ¹¹、R ¹¹和R ¹²、R ¹³和R ¹⁴、R ¹⁴和R ¹⁵、R ¹⁵和R ¹⁶、R ¹⁶和R ¹⁷、R ¹⁷和R ¹⁸、R ¹⁸和R ¹⁹、R ¹⁹和R ²⁰、R ²⁰和R ²¹、R ²¹和R ²²、R ²²和R ²³、R ²³和R ²⁴、R ²⁴和R ²⁵、R ²⁵和R ²⁶可以彼此鍵結而形成環狀結構。其中，在X ¹為氮原子時，R ¹⁷和R ¹⁸彼此鍵結而形成單鍵以形成吡咯環，在X ²為氮原子時，R ²¹和R ²²彼此鍵結而形成單鍵以形成吡咯環。] 在本發明的一態樣中，在X ¹為氮原子，R ⁷和R ⁸及R ²¹和R ²²經由氮原子鍵結而形成6員環，R ¹⁷和R ¹⁸彼此鍵結而形成單鍵時，R ¹～R ⁶中的至少一個為經取代或未經取代的芳基或者R ¹和R ²、R ²和R ³、R ³和R ⁴、R ⁴和R ⁵、R ⁵和R ⁶中的任一個彼此鍵結而形成芳香環或雜芳環。在本發明的一態樣中，在X ¹為硼原子，X ²為氮原子，R ⁷和R ⁸、R ¹⁷和R ¹⁸彼此鍵結而形成包含硼原子之環狀結構之情況下，該環狀結構為5～7員環，在為6員環之情況下，R ⁷和R ⁸、R ¹⁷和R ¹⁸彼此鍵結而形成-B（R ³²）-、-CO-、-CS-或-N（R ²⁷）-。R ²⁷表示氫原子、氘原子或取代基。 [14]一種電子障壁材料，其係包含[1]至[10]之任一項所述之化合物。 [15]如[14]所述之電子障壁材料，其係用於與延遲螢光材料組合使用。 [16]如[14]所述之電子障壁材料，其係用於與上述通式（G）所表示之化合物組合使用。 [17]一種組成物，其係在[1]至[10]之任一項所述之化合物中摻雜了延遲螢光材料。 [18]如[17]所述之組成物，其係膜狀。 [19]如[17]或[18]所述之組成物，其中，前述延遲螢光材料為具有取代為苯環之氰基的數量為一個之氰基苯結構之化合物。 [20]如[17]或[18]所述之組成物，其中，前述延遲螢光材料為具有取代為苯環之氰基的數量為兩個之二氰基苯結構之化合物。 [21]如[17]或[18]所述之組成物，其中，前述延遲螢光材料為下述通式（E）所表示之化合物。 通式（E） [化學式3]

[在通式（E）中，R ¹～R ⁴分別獨立地表示氫原子、氘原子、經取代或未經取代的烷基、經取代或未經取代的芳基或者供體基團。又，R ¹～R ⁴中的兩個以上為供體基團，該兩個以上的供體基團中的至少一個為經取代之環縮合咔唑-9-基。X ¹～X ³分別獨立地表示N或C（R），但是X ¹～X ³中的至少一個為N。R表示氫原子、氘原子或取代基。Ar ¹及Ar ²分別獨立地表示經取代或未經取代的芳基。L ¹表示單鍵或2價的連接基。] [22]如[17]至[21]之任一項所述之組成物，其係進一步包含最低激發單重態能量低於前述主體材料及前述延遲螢光材料的螢光性化合物。 [23]如[17]至[22]之任一項所述之組成物，其中，前述延遲螢光材料或前述螢光性化合物為上述通式（G）所表示之化合物。 [24]一種有機發光元件，其係具有由[17]至[23]之任一項所述之組成物組成之層。 [25]如[24]所述之有機發光元件，其中，前述層僅由選自包括碳原子、氫原子、氮原子、氧原子、硫原子、硼原子及鹵素原子之群組中的原子組成。 [26]如[24]所述之有機發光元件，其中，前述層僅由選自包括碳原子、氫原子、氮原子、氧原子及硫原子之群組中的原子組成。 [27]如[24]至[26]之任一項所述之有機發光元件，其係有機電致發光元件。 [28]如[24]至[27]之任一項所述之有機發光元件，其中，前述組成物不包含前述螢光性化合物，來自前述元件的發光的最大成分為來自前述延遲螢光材料的發光。 [29]如[24]至[27]之任一項所述之有機發光元件，其中，前述組成物包含前述螢光性化合物，來自前述元件的發光的最大成分為來自前述螢光性化合物的發光。 [發明效果] [1] A compound represented by the following general formula (1). [chemical formula 1]

[In the general formula (1), R ¹ to R ⁷ independently represent a hydrogen atom, a deuterium atom, an alkyl group that may be deuterated, or a substituted or unsubstituted aryl group, and at least one of R ¹ to R ⁴ One is substituted or unsubstituted aryl. R ⁸ to R ¹⁹ each independently represent a hydrogen atom, a deuterium atom, or an alkyl group that may be deuterated. ] [2] The compound according to [1], wherein only one of R ¹ to R ⁴ is a substituted or unsubstituted aryl group. [3] The compound according to [1] or [2], wherein R ² is a substituted or unsubstituted aryl group. [4] The compound according to any one of [1] to [3], wherein R ⁴ is a substituted or unsubstituted aryl group. [5] The compound according to any one of [1] to [4], wherein the substituted or unsubstituted aryl group is a substituted or unsubstituted phenyl group. [6] The compound according to any one of [1] to [5], wherein the aforementioned substituted or unsubstituted aryl is substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted Substituted dibenzothienyl. [7] The compound according to any one of [1] to [6], wherein R ⁵ to R ¹¹ are each independently a hydrogen atom or a deuterium atom. [8] The compound according to any one of [1] to [7], wherein R ¹² to R ¹⁹ are each independently a hydrogen atom or a deuterium atom. [9] The compound according to any one of [1] to [8], wherein at least one of R ¹ to R ⁴ contains a deuterium atom. [10] The compound according to any one of [1] to [9], wherein at least one of R ¹² to R ¹⁹ contains a deuterium atom. [11] A host material comprising the compound described in any one of [1] to [10]. [12] The host material according to [10], which is used together with a delayed fluorescent material. [13] The host material according to [11], which is used together with a compound represented by the following general formula (G). General formula (G) [Chemical formula 2]

[In the general formula (G), one of X ¹ and X ² is a nitrogen atom, and the other is a boron atom. R ¹ to R ²⁶ , A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. R ¹ and R ² , R 2 and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , ^{R 9} and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R 14 , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 17 and} R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R 21 and R 22 , R ²² and R ²³ , R ²³ and R ²⁴ , ^{R 24 and} R ^{25 ,} R ²⁵ and R ²⁶ may be bonded to each other to form a ring shape structure. Wherein, when X ¹ is a nitrogen atom, R ¹⁷ and R ¹⁸ are bonded to each other to form a single bond to form a pyrrole ring, and when X ² is a nitrogen atom, R ²¹ and R ²² are bonded to each other to form a single bond to form a pyrrole ring ring. ] In one aspect of the present invention, X ¹ is a nitrogen atom, R ⁷ and R ⁸ and R ²¹ and R ²² are bonded via nitrogen atoms to form a 6-membered ring, R ¹⁷ and R ¹⁸ are bonded to each other to form a single When a bond is used, at least one of R ¹ to R ⁶ is a substituted or unsubstituted aryl group or R ¹ and R 2 , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ^{5 and} Any one of R ⁶ is bonded to each other to form an aromatic ring or a heteroaromatic ring. In one aspect of the present invention, when X ¹ is a boron atom, X ² is a nitrogen atom, and R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ are bonded to each other to form a ring structure containing a boron atom, the The ring structure is a 5-7-membered ring. In the case of a 6-membered ring, R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ are bonded to each other to form -B(R ³² )-, -CO-, -CS- or -N( ^R27 )-. R ²⁷ represents a hydrogen atom, a deuterium atom or a substituent. [14] An electron barrier material comprising the compound described in any one of [1] to [10]. [15] The electron barrier material as described in [14], which is used in combination with a delayed fluorescent material. [16] The electron barrier material as described in [14], which is used in combination with the compound represented by the above general formula (G). [17] A composition in which a retarded fluorescent material is doped into the compound described in any one of [1] to [10]. [18] The composition according to [17], which is membranous. [19] The composition according to [17] or [18], wherein the retarded fluorescent material is a compound having a cyanobenzene structure in which one cyano group is substituted with a benzene ring. [20] The composition according to [17] or [18], wherein the retarded fluorescent material is a compound having a dicyanobenzene structure in which two cyano groups are substituted with benzene rings. [21] The composition according to [17] or [18], wherein the delayed fluorescent material is a compound represented by the following general formula (E). General formula (E) [Chemical formula 3]

[In general formula (E), R ¹ to R ⁴ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. Also, two or more of R ¹ to R ⁴ are donor groups, and at least one of the two or more donor groups is a substituted ring-condensed carbazol-9-yl group. X ¹ to X ³ each independently represent N or C (R), but at least one of X ¹ to X ³ is N. R represents a hydrogen atom, a deuterium atom or a substituent. Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group. L ¹ represents a single bond or a divalent linking group. [22] The composition according to any one of [17] to [21], which further includes a fluorescent compound having a lower minimum excited singlet energy than the host material and the delayed fluorescent material. [23] The composition according to any one of [17] to [22], wherein the delayed fluorescent material or the fluorescent compound is a compound represented by the above general formula (G). [24] An organic light-emitting device having a layer composed of the composition described in any one of [17] to [23]. [25] The organic light-emitting device according to [24], wherein the layer is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms . [26] The organic light-emitting device according to [24], wherein the layer is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. [27] The organic light-emitting device according to any one of [24] to [26], which is an organic electroluminescent device. [28] The organic light-emitting device according to any one of [24] to [27], wherein the composition does not contain the fluorescent compound, and the largest component of light emission from the device is derived from the retarded fluorescent material. glowing. [29] The organic light-emitting device according to any one of [24] to [27], wherein the composition contains the fluorescent compound, and the largest component of light emitted from the device is derived from the fluorescent compound. glow. [Invention effect]

It is possible to provide an organic light-emitting device capable of maintaining high luminous efficiency and low-voltage driving even under high-temperature driving, as long as the compound of the present invention is used in the organic light-emitting device. Also, an organic light-emitting device using the compound of the present invention exhibits excellent light-emitting characteristics.

In the following, the contents of the present invention will be described in detail. The description of the constituent requirements described below may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiment or specific examples. In addition, in this specification, using the numerical range represented by "-" means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, the isotope type of the hydrogen atom present in the molecule of the compound used in the present invention is not particularly limited.

(Compound Represented by General Formula (1)) In the present invention, a compound represented by the following general formula (1) is used. [chemical formula 4]

In the general formula (1), R ¹ to R ⁷ independently represent a hydrogen atom, a deuterium atom, an alkyl group that may be deuterated or a substituted or unsubstituted aryl group, and at least one of R ¹ to R ⁴ is a substituted or unsubstituted aryl group. R ⁸ to R ¹⁹ each independently represent a hydrogen atom, a deuterium atom, or an alkyl group that may be deuterated.

The "alkyl" in the present invention may be any of linear, branched and cyclic. In addition, two or more types of linear moieties, cyclic moieties, and branched moieties may be present in admixture. The carbon number of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, n-pentyl, isopentyl, n-hexyl, cyclopentyl, and base, cyclohexyl, cycloheptyl. In one aspect of the present invention, the carbon number of the alkyl group is 1-4. In one aspect of the invention, the alkyl group is methyl. In one aspect of the invention, the alkyl group is isopropyl. In one aspect of the invention, the alkyl group is tertiary butyl. When a plurality of alkyl groups exist in the molecule represented by the general formula (1), these alkyl groups may be the same as or different from each other. In one aspect of the present invention, the alkyl groups in the molecules represented by the general formula (1) are all the same. The number of alkyl groups in the molecule represented by the general formula (1) can be zero or more, one or more, two or more, four or more, and eight or more. The number of alkyl groups in the molecule represented by general formula (1) may be 20 or less, 10 or less, 5 or less, or 3 or less. The number of alkyl groups in the molecule represented by general formula (1) may be zero. Furthermore, the number of alkyl groups mentioned here also includes the number of alkyl groups substituted with aryl groups. The "alkyl group that may be deuterated" in the present invention means that at least one of the hydrogen atoms of the alkyl group may be replaced by a deuterium atom. All hydrogen atoms of the alkyl group may be substituted with deuterium atoms. For example, methyl groups that can be deuterated include _CH3 , _CDH2 , _CD2H , _CD3 . The "alkyl group that may be deuterated" is preferably an alkyl group that is not deuterated at all or an alkyl group in which all hydrogen atoms are replaced with deuterium atoms. In one aspect of the present invention, as the "alkyl group that may be deuterated", an alkyl group that is not deuterated at all is selected. In one aspect of the present invention, as the "alkyl group that may be deuterated", an alkyl group in which all hydrogen atoms are replaced with deuterium atoms is selected. In one aspect of the present invention, the "alkyl group that may be deuterated" is undeuterated methyl [-CH ₃ ], undeuterated ethyl [-CH 2 CH 3 ], undeuterated ethyl [-CH ₂ CH ₃ ], undeuterated Isopropyl [-CH(CH ₃ ) ₂ ], undeuterated tertiary butyl [-C(CH ₃ ) ₃ ] or methyl [-CD ₃ ] with all hydrogen atoms deuterated. In one aspect of the present invention, the "alkyl group that may be deuterated" is undeuterated methyl group [-CH ₃ ] or methyl group [-CD ₃ ] with all hydrogen atoms deuterated. In one aspect of the present invention, there is an alkyl group in which at least one hydrogen atom is replaced by a deuterium atom in the molecule represented by the general formula (1).

The "aryl group" that can be used for R ¹ to R ⁷ may be a single ring or a condensed ring formed by condensing two or more rings. When monocyclic, aryl is phenyl. In the case of a condensed ring, the aryl group is a group obtained by further condensing a phenyl group with one or more rings. The ring condensed with the phenyl group may be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, and may also be a ring formed by such condensation. Preferred are aromatic hydrocarbon rings and aromatic heterocyclic rings. A benzene ring is mentioned as an aromatic hydrocarbon ring. The benzene ring can be further condensed with other benzene rings, and can also be condensed with heterocycles such as pyridine rings. The aromatic heterocycle means an aromatic ring containing heteroatoms as ring skeleton constituent atoms, preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring can be used. In one aspect of the present invention, as the aromatic heterocycle, a furan ring, a thiophene ring, and a pyrrole ring can be used, and a furan ring and a thiophene ring can be preferably used. In a preferred aspect of the present invention, the condensed ring is the furan ring of benzofuran, the thiophene ring of benzothiophene, the pyrrole ring of indole, more preferably the furan ring of benzofuran, the thiophene ring of benzothiophene Thiophene ring. Upon condensation with the furan ring of benzofuran, the aryl group becomes a dibenzofuranyl group. Upon condensation with the thiophene ring of benzothiophene, the aryl group becomes a dibenzothienyl group. Furthermore, the ring condensed with the phenyl group may be a cyclopentadiene ring, a cyclopentene ring, a cyclohexadiene ring, a cyclohexene ring, or the like. When the aryl group is a condensed ring, the number of rings constituting the condensed ring is preferably 2 to 6, for example, can be selected from 2 to 4 rings. Specific examples of the ring constituting the aryl group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylenyl ring, a dibenzofuran ring, and a dibenzothiophene ring. Specific examples of the aryl group include phenyl, naphthalene-1-yl, naphthalene-2-yl, anthracene-1-yl, anthracene-2-yl, and anthracene-9-yl. Further, other specific examples of the aryl group include dibenzofuran-1-yl, dibenzofuran-2-yl, dibenzofuran-3-yl, and dibenzofuran-4-yl. Furthermore, other specific examples of the aryl group include dibenzothiophen-1-yl, dibenzothiophen-2-yl, dibenzothiophen-3-yl, and dibenzothiophen-4-yl. In one aspect of the present invention, the aryl group is dibenzofuran-1-yl or dibenzothiophen-1-yl. In one aspect of the present invention, the aryl group is dibenzofuran-2-yl or dibenzothiophen-2-yl. In one aspect of the present invention, the aryl group is dibenzofuran-3-yl or dibenzothiophen-3-yl. In one aspect of the present invention, the aryl group is dibenzofuran-4-yl or dibenzothiophen-4-yl. These groups mentioned as specific examples may be substituted.

The substituent of the aryl group may be selected from the following substituent group A, may be selected from the following substituent group B, may be selected from the following substituent group C, or may be Those selected from the following substituent group D may also be those selected from the following substituent group E. In this specification, "substituent group A" means selected from the group consisting of deuterium atom, hydroxyl group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (for example, carbon number 1 to 40), Alkoxy (for example, carbon number 1-40), alkylthio group (for example, carbon number 1-40), aryl group (for example, carbon number 6-30), aryloxy group (for example, carbon number 6-30) , arylthio group (for example, with 6 to 30 carbon atoms), heteroaryl group (for example, with 5 to 30 atoms in the ring skeleton), heteroaryloxy group (for example, with 5 to 30 atoms in the ring skeleton), heteroarylthio Group (for example, the number of atoms in the ring skeleton is 5 to 30), acyl group (for example, the number of carbons 1 to 40), alkenyl (for example, the number of carbons 1 to 40), alkynyl (for example, the number of carbons 1 to 40), Alkoxycarbonyl (for example, with 1 to 40 carbons), aryloxycarbonyl (for example, with 1 to 40 carbons), heteroaryloxycarbonyl (for example, with 1 to 40 carbons), silyl (for example, with 1 to 40 carbons) 40 trialkylsilyl group) and a group obtained by combining two or more groups in the group of nitro. In this specification, "substituent group B" means selected from groups including deuterium atoms, alkyl groups (for example, with 1 to 40 carbons), alkoxy groups (for example, with 1 to 40 carbons), aryl groups (for example, with carbon numbers 6-30), aryloxy group (for example, 6-30 carbon atoms), heteroaryl group (for example, 5-30 ring skeleton atoms), heteroaryloxy group (for example, 5-30 ring skeleton atoms) . One group or a group obtained by combining two or more of the group of diarylamine groups (for example, having 0 to 20 carbon atoms). In this specification, "substituent group C" represents a group consisting of deuterium atom, alkyl (for example, carbon number 1-20), aryl group (for example, carbon number 6-22), heteroaryl group (for example, ring skeleton Constituting one group or a group obtained by combining two or more of the group consisting of 5 to 20 atoms), diarylamine group (for example, carbon number 12 to 20). In this specification, "substituent group D" means selected from the group consisting of deuterium atom, alkyl group (for example, carbon number 1-20), aryl group (for example, carbon number 6-22) and heteroaryl group (for example, ring skeleton Constituting one group or a group obtained by combining two or more of the group of 5 to 20 atoms. In this specification, "substituent group E" represents a group selected from the group consisting of a deuterium atom, an alkyl group (for example, with 1 to 20 carbons) and an aryl group (for example, with 6 to 22 carbons) or A group obtained by combining two or more.

In one aspect of the present invention, the aryl groups that can be adopted by R ¹ to R ⁷ are substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted Dibenzothienyl. In one aspect of the present invention, the aryl groups that can be used by R ¹ to R ⁷ are phenyl groups that may be substituted by one or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups, for example, A phenyl group which may be substituted with one or more groups selected from the group consisting of a deuterium atom and a phenyl group. In one aspect of the present invention, the aryl groups that R ¹ to R ⁷ can adopt are dibenzofuranyl groups that may be substituted with one or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. , such as a dibenzofuryl group which may be substituted with a deuterium atom. In one aspect of the present invention, the aryl groups that R ¹ to R ⁷ can adopt are dibenzothienyl groups that may be substituted with one or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups. , such as a dibenzothienyl group which may be substituted with a deuterium atom. In one aspect of the present invention, at least one of R ¹ to R ⁴ contains a deuterium atom. Among R ¹ to R ⁷ of the general formula (1), the number of substituted or unsubstituted aryl groups is 1 to 4, preferably one or two, for example one. In one aspect of the present invention, the number of substituted or unsubstituted aryl groups among R ¹ to R ⁴ is one or two, for example one, for example two. In one aspect of the present invention, the number of substituted or unsubstituted aryl groups among R ⁵ to R ⁷ is zero or one, such as zero, such as one. In one aspect of the invention, at least R ¹ is substituted or unsubstituted aryl. In one aspect of the invention, at least R ² is substituted or unsubstituted aryl. In one aspect of the invention, at least R ³ is substituted or unsubstituted aryl. In one aspect of the invention, at least R ⁴ is substituted or unsubstituted aryl. In one aspect of the invention, at least R ⁵ is substituted or unsubstituted aryl. In one aspect of the invention, at least R ⁶ is substituted or unsubstituted aryl. In one aspect of the invention, at least R ⁷ is substituted or unsubstituted aryl. In one aspect of the invention, only ^R is substituted or unsubstituted aryl. In one aspect of the invention, only R ² is substituted or unsubstituted aryl. In one aspect of the invention, only ^R3 is substituted or unsubstituted aryl. In one aspect of the invention, only ^R4 is substituted or unsubstituted aryl. In one aspect of the present invention, except for substituted or unsubstituted aryl groups, R ¹ to R ⁷ are all hydrogen atoms or deuterium atoms, for example, all are hydrogen atoms.

Specific examples of substituted or unsubstituted aryl groups that can be used for R ¹ to R ⁷ in the general formula (1) are given below. However, the structures that can be adopted in the present invention are not limitedly interpreted by these specific examples. In the following specific examples, * represents the bonding position of the benzene ring bonded to R ¹ to R ⁷ of the general formula (1). In the present invention, methyl is not expressed as CH ₃ and description is omitted. For example, Ar2-Ar7 are substituted by methyl, Ar8 and Ar9 are substituted by isopropyl, Ar10 and Ar11 are substituted by tertiary butyl. [chemical formula 5]

Those in which all the hydrogen atoms present in the alkyl groups of Ar2 to Ar11 are substituted with deuterium atoms are exemplified here as Ar2(d) to Ar11(d), respectively. Those in which all the hydrogen atoms of Ar1 to Ar21 are substituted with deuterium atoms are exemplified here as Ar1(D) to Ar21(D), respectively.

R ⁸ to R ¹¹ in the general formula (1) each independently represent a hydrogen atom, a deuterium atom, or an alkyl group that may be deuterated. For the description and specific examples of the alkyl group, reference can be made to the corresponding description of R ¹ to R ⁷ . In one aspect of the present invention, R ⁸ to R ¹¹ are each independently a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ⁸ to R ¹¹ are hydrogen atoms. Specific examples of the methylphenylene groups to which R ⁸ to R ¹¹ in the general formula (1) are bonded are given below. However, the structures that can be adopted in the present invention are not limitedly interpreted by these specific examples. In the following specific examples, one of * represents a bonded position to the nitrogen atom of carbazole of the general formula (1), and the other represents a bonded position to dibenzofuran. In the present invention, methyl is not expressed as CH ₃ and description is omitted. For example, L2-L6 are each substituted with methyl, L7 is substituted with ethyl, and L8 is substituted with isopropyl. In addition, t-Bu represents a tertiary butyl group, and D represents a deuterium atom. [chemical formula 6]

Those in which all hydrogen atoms present in the alkyl groups of L2 to L8 are substituted with deuterium atoms are exemplified here as L2(d) to L8(d), respectively. Those in which all the hydrogen atoms in L1 to L14 are substituted with deuterium atoms are exemplified here as L1(D) to L14(D), respectively.

R ¹² to R ¹⁹ in the general formula (1) each independently represent a hydrogen atom, a deuterium atom, or an alkyl group that may be deuterated. For the description and specific examples of the alkyl group, reference can be made to the corresponding description of R ¹ to R ⁷ . In one aspect of the present invention, R ¹² to R ¹⁹ are each independently a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ¹² to R ¹⁹ are hydrogen atoms. Specific examples of the carbazol-9-yl group to which R ¹² to R ¹⁹ in the general formula (1) are bonded are given below. However, the structures that can be adopted in the present invention are not limitedly interpreted by these specific examples. In the following specific examples, * represents the bonding position with the methylene group of the general formula (1). In the present invention, methyl is not expressed as CH ₃ and description is omitted. For example, Cz2-Cz5 are respectively substituted with methyl, Cz6 is substituted with ethyl, Cz7 is substituted with isopropyl, and Cz8 is substituted with tertiary butyl. [chemical formula 7]

Those in which all hydrogen atoms present in the alkyl groups of Cz2 to Cz8 are substituted with deuterium atoms are exemplified here as Cz2(d) to Cz8(d), respectively. Those in which all the hydrogen atoms of Cz1 to Cz8 were substituted with deuterium atoms are exemplified here as Cz1(D) to Cz8(D), respectively.

In one aspect of the present invention, R ⁵ to R ¹⁹ of the general formula (1) are each independently a hydrogen atom or a deuterium atom, for example, all are hydrogen atoms. In one aspect of the present invention, R ¹ to R ⁴ and R ⁵ to R ¹⁹ other than the substituted or unsubstituted aryl group are each independently a hydrogen atom or a deuterium atom, for example, all are hydrogen atoms. In one aspect of the present invention, R ² is a substituted or unsubstituted aryl group, R ¹ and R ³ to R ¹⁹ are each independently a hydrogen atom or a deuterium atom, for example, all are hydrogen atoms. In one aspect of the present invention, R ⁴ is a substituted or unsubstituted aryl group, R ¹ to R ³ and R ⁵ to R ¹⁹ are each independently a hydrogen atom or a deuterium atom, for example, all are hydrogen atoms. In one aspect of the present invention, at least one of R ¹ to R ⁴ (for example, one, for example only R ² , for example only R ⁴ ) is a phenyl group that may be substituted by a deuterium atom, or a phenyl group that may be substituted by a deuterium atom The dibenzofuryl group or the dibenzothienyl group which may be substituted with a deuterium atom, and the other R ¹ to R ⁴ and R ⁵ to R ¹⁹ are each independently a hydrogen atom or a deuterium atom, for example, all are hydrogen atoms.

In one aspect of the present invention, the compound of the general formula (1) is represented by the following general formula (2). However, for the description and preferred ranges of R ¹ , R ³ to R ¹⁹ , reference can be made to the corresponding description of the general formula (1). Ar is a substituted or unsubstituted aryl group, and the corresponding description of the general formula (1) can be referred to. [chemical formula 8]

In one aspect of the present invention, the compound of the general formula (1) is represented by the following general formula (3). However, for the description and preferred ranges of R ¹ to R ³ and R ⁵ to R ¹⁹ , reference can be made to the corresponding description of the general formula (1). Ar is a substituted or unsubstituted aryl group, and the corresponding description of the general formula (1) can be referred to. [chemical formula 9]

Specific examples of the compound represented by the general formula (1) are given below, but compounds usable in the present invention are not limitedly interpreted by these specific examples. In the following, each compound is identified by specifying Ar in each structure. [chemical formula 10]

As a preferable group of the compound represented by General formula (1), the group which consists of the following compounds is mentioned. [chemical formula 11]

The compound represented by the general formula (1) is used as a host material for doping a light-emitting material. In particular, it is used as a host material for doping delayed fluorescent materials. The material to be doped may be not only one kind, but also plural kinds. The doping material is selected from those whose lowest excited singlet energy is lower than that of the compound represented by the general formula (1). The doped material is preferably a retarded fluorescent material described later. The compound represented by the general formula (1) is also used as a carrier barrier material, for example as an electron barrier material. In organic light-emitting elements such as an organic electroluminescent element, it can be effectively used in a barrier layer (for example, an electron barrier layer). In this case, it is preferable to use a compound represented by the general formula (1) as an electron barrier material in combination with a delayed fluorescent material. In particular, it is preferably used in combination with a compound represented by the general formula (E) described below or a compound represented by the general formula (G) described below. The "combined use" mentioned here means simultaneous use in one device, and includes, for example, the case where a retarded fluorescent material is included in the light emitting layer and the compound represented by the general formula (1) is included in the electron barrier layer.

(Delayed Fluorescent Material) The compound represented by the general formula (1) is used as a host material for use with a delayed fluorescent material. The "delayed fluorescent material" referred to herein is an organic compound that undergoes an inverse intersystem transition from an excited triplet state to an excited singlet state in an excited state, and radiates when returning from the excited singlet state to the ground state delayed fluorescence. In the present invention, when the luminescence lifetime is measured with a fluorescence lifetime measurement system (stripe photography system manufactured by Hamamatsu Photonics KK, etc.), those whose luminescence lifetime is 100 ns (nanosecond) or more are observed are called delayed fluorescent materials . When the compound represented by the general formula (1) and the delayed fluorescent material are used in combination, the delayed fluorescent material receives energy from the compound represented by the general formula (1) in the excited singlet state and transitions to the excited singlet state. Also, the delayed fluorescent material can receive energy from the compound represented by the general formula (1) in the excited triplet state and transition to the excited triplet state. The difference between the excited singlet state energy and the excited triplet state energy (ΔE _ST ) of the delayed fluorescent material is small, so the delayed fluorescent material in the excited triplet state is easy to reverse the intersystem transition to the delayed fluorescent material in the excited singlet state. The excited singlet delayed fluorescent material generated through these pathways contributes to light emission.

The difference ΔE _ST between the lowest excited singlet energy of the delayed fluorescent material and the lowest excited triplet energy of 77K is preferably 0.3eV or less, more preferably 0.25eV or less, more preferably 0.2eV or less, and more preferably 0.15eV or less 0.1 eV or less is still more preferable, 0.07 eV or less is still more preferable, 0.05 eV or less is still more preferable, 0.03 eV or less is still more preferable, 0.01 eV or less is especially preferable. When ΔE _ST is small, the inverse intersystem transition from the excited singlet state to the excited triplet state is easily performed by absorbing thermal energy, and thus functions as a heat-activated delayed fluorescent material. The heat-activated delayed fluorescent material can absorb the heat emitted by the device and relatively easily transition from the excited triplet state inversely to the excited singlet state, and contribute the energy efficiency of the excited triplet state to light emission.

The lowest excited singlet energy (E _S1 ) and the lowest excited triplet energy (E _T1 ) of the compounds in the present invention are values obtained by the following procedure. ΔE _ST is a value obtained by calculating E _S1 -E _T1 . (1) Minimum excited singlet energy ( _ES1 ) Prepare a thin film or toluene solution (concentration: 10 ^-5 mol/L) of the compound to be measured as a sample. The fluorescence spectrum of this sample was measured at normal temperature (300K). In the fluorescence spectrum, the vertical axis represents luminescence, and the horizontal axis represents wavelength. A tangent line is drawn with respect to the rising of the short-wave side of the emission spectrum, and the wavelength value λedge [nm] of the intersection point of the tangent line and the horizontal axis is obtained. Let the value obtained by converting this wavelength value into an energy value by the conversion formula shown below be E _S1 . Conversion formula: E _S1 [eV]=1239.85/λedge Regarding the measurement of the emission spectrum in the examples described later, an LED light source (manufactured by Thorlabs, Inc., M300L4) was used as the excitation light source, and a detector (manufactured by Hamamatsu Photonics KK, PMA-12 multi-channel spectrometer C10027-01) to carry out. (2) Minimum excited triplet energy (E _T1 ) Cool the same sample as used in the measurement of the lowest excited singlet energy (E _S1 ) to 77[K] with liquid nitrogen, and emit excitation light (300nm ) is irradiated onto the sample for phosphorescence measurement, and the phosphorescence is measured using a detector. The luminescence after 100 milliseconds after irradiation with excitation light was defined as the phosphorescence spectrum. A tangent line is drawn with respect to the rising of the short-wavelength side of the phosphorescence spectrum, and the wavelength value λedge [nm] of the intersection point of the tangent line and the horizontal axis is obtained. Let the value obtained by converting this wavelength value into an energy value by the conversion formula shown below be E _T1 . Conversion formula: E _T1 [eV]=1239.85/λedge The tangent line to the rise on the short-wavelength side of the phosphorescence spectrum is drawn as follows. When moving from the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum on the spectral curve, a tangent line at each point on the curve toward the long-wavelength side is considered. The tangent line increases in slope as the curve rises (ie, as the vertical axis increases). A tangent line drawn at a point where the value of the slope takes a maximum value is defined as a tangent line with respect to the rise of the short-wavelength side of the phosphorescence spectrum. Furthermore, the maximum point of the peak intensity having 10% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the maximum value on the shortest wavelength side is the point where the value of the slope takes the maximum value. The tangent line drawn above is set as a tangent line with respect to the rise of the short-wavelength side of the phosphorescence spectrum.

In a preferred aspect of the present invention, a compound having a cyanobenzene structure (cyanobenzene derivative) having one cyano group substituted with a benzene ring is used as the retarded fluorescent material. In another preferred aspect of the present invention, a compound having a dicyanobenzene structure (dicyanobenzene derivative) having two cyano groups substituted with benzene rings is used as a delayed fluorescent material. In another preferred aspect of the present invention, a compound (azabenzene derivative) having a ring skeleton of a benzene ring in which at least one of the carbon atoms is substituted with a nitrogen atom is used as a delayed fluorescence Material.

在通式（4）中，R ²¹～R ²³中的一個表示氰基或下述通式（5）所表示之基團，R ²¹～R ²³的其餘兩個和R ²⁴及R ²⁵中的至少一個表示下述通式（6）所表示之基團，R ²¹～R ²⁵的其餘部分表示氫原子或取代基（其中，在此所述之取代基不是氰基、下述通式（5）所表示之基團、下述通式（6）所表示之基團）。 [化學式13]

在通式（5）中，L ¹表示單鍵或2價的連接基，R ³¹及R ³²分別獨立地表示氫原子或取代基，*表示鍵結位置。 [化學式14]

在通式（6）中，L ²表示單鍵或2價的連接基，R ³³及R ³⁴分別獨立地表示氫原子或取代基，*表示鍵結位置。 In a preferred aspect of the present invention, a compound represented by the following general formula (4) is used as a delayed fluorescent material. [chemical formula 12]

In general formula (4), one of R ²¹ to R ²³ represents a cyano group or a group represented by the following general formula (5), the other two of R ²¹ to R ²³ and R ²⁴ and R ²⁵ At least one represents a group represented by the following general formula (6), and the rest of R ²¹ to R ²⁵ represent hydrogen atoms or substituents (wherein, the substituents described here are not cyano, the following general formula (5 ), a group represented by the following general formula (6)). [chemical formula 13]

In the general formula (5), L ¹ represents a single bond or a divalent linking group, R ³¹ and R ³² each independently represent a hydrogen atom or a substituent, and * represents a bonding position. [chemical formula 14]

In the general formula (6), L ² represents a single bond or a divalent linking group, R ³³ and R ³⁴ each independently represent a hydrogen atom or a substituent, and * represents a bonding position.

In a preferred aspect of the present invention, R ²² is cyano. In a preferred aspect of the present invention, R ²² is a group represented by general formula (5). In one aspect of the present invention, R ²¹ is a cyano group or a group represented by general formula (5). In one aspect of the present invention, R ²³ is a cyano group or a group represented by general formula (5). In one aspect of the present invention, one of R ²¹ to R ²³ is cyano. In one aspect of the present invention, one of R ²¹ to R ²³ is a group represented by general formula (5).

In a preferred aspect of the present invention, L ¹ in the general formula (5) is a single bond. In one aspect of the present invention, ^L is a divalent linking group, preferably a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, more preferably a substituted or The unsubstituted arylylene group is more preferably a substituted or unsubstituted 1,4-phenylene group (as a substituent, for example, an alkyl group having 1 to 3 carbon atoms). In one aspect of the present invention, R ³¹ and R ³² in the general formula (5) are independently selected from groups including alkyl (for example, 1-40 carbons), aryl (for example, 6-30 carbons ), heteroaryl (for example, ring skeleton with 5-30 atoms), alkenyl (for example, carbon number 1-40) and alkynyl (for example, carbon number 1-40) group or two Groups obtained by combining the above groups (hereinafter, these groups are referred to as "groups of substituent group A"). In a preferred aspect of the present invention, R ³¹ and R ³² are independently substituted or unsubstituted aryl groups (for example, with 6 to 30 carbon atoms). As substituents for the aryl groups, there are A radical of substituent group A. In a preferred aspect of the present invention, R ³¹ and R ³² are the same.

In a preferred aspect of the present invention, L ² in the general formula (6) is a single bond. In one aspect of the present invention, ^L is a divalent linking group, preferably a substituted or unsubstituted arylylene or a substituted or unsubstituted heteroarylylene, more preferably a substituted or The unsubstituted arylylene group is more preferably a substituted or unsubstituted 1,4-phenylene group (as a substituent, for example, an alkyl group having 1 to 3 carbon atoms). In one aspect of the present invention, R ³³ and R ³⁴ in general formula (6) independently represent substituted or unsubstituted alkyl (for example, carbon number 1-40), substituted or unsubstituted Alkenyl (for example, 1 to 40 carbons), substituted or unsubstituted aryl (for example, 6 to 30 carbons) or substituted or unsubstituted heteroaryl (for example, 5 to 30 carbons ). Examples of substituents for the alkyl, alkenyl, aryl, and heteroaryl groups described here include hydroxyl, halogen atoms (for example, fluorine, chlorine, bromine, and iodine atoms), alkyl (for example, carbon number 1-40), alkoxy group (for example, carbon number 1-40), alkylthio group (for example, carbon number 1-40), aryl group (for example, carbon number 6-30), aryloxy group (for example, carbon number 6-30), arylthio group (for example, carbon number 6-30), heteroaryl group (for example, ring skeleton composition atom number 5-30), heteroaryloxy group (for example, ring skeleton composition 5-30 atoms), heteroarylthio group (for example, 5-30 atoms in the ring skeleton), acyl group (for example, 1-40 carbon atoms), alkenyl group (for example, 1-40 carbon atoms), alkynyl group (for example, carbon number 1-40), alkoxycarbonyl group (for example, carbon number 1-40), aryloxycarbonyl group (for example, carbon number 1-40), heteroaryloxycarbonyl group (for example, carbon number 1-40), A silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms), a nitro group, and a cyano group, or a group obtained by combining two or more (hereinafter, the Such groups are referred to as "groups of substituent group B"). R ³³ and R ³⁴ may be bonded to each other via a single bond or a linker to form a ring structure. In particular, when R ³³ and R ³⁴ are aryl groups, it is preferable to bond each other via a single bond or a linker to form a ring structure. Examples of the linking group described here include -O-, -S-, -N(R ³⁵ )-, -C(R ³⁶ )(R ³⁷ )-, -C(=O)-, -O -, -S-, -N(R ³⁵ )-, -C(R ³⁶ )(R ³⁷ )- are preferred, and -O-, -S-, -N(R ³⁵ )- are more preferred. R ³⁵ to R ³⁷ each independently represent a hydrogen atom or a substituent. As a substituent, the group of the above-mentioned substituent group A or the group of the following substituent group B can be selected, preferably selected from the group consisting of an alkyl group with 1 to 10 carbons and an aryl group with 6 to 14 carbons. A group in a group or a group obtained by combining two or more groups.

The group represented by the general formula (6) is preferably a group represented by the following general formula (7). [chemical formula 15]

L ¹¹ in the general formula (7) represents a single bond or a divalent linking group. For the description and preferred range of ^L11 , the description and preferred range of ^L2 above can be referred to. R ⁴¹ to R ⁴⁸ in the general formula (7) each independently represent a hydrogen atom or a substituent. R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a ring structure . The cyclic structure formed by bonding with each other may be an aromatic ring or an aliphatic ring, and may include heteroatoms, and the cyclic structure may be a condensed ring of two or more rings. As the hetero atom mentioned here, one selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom is preferable. Examples of the formed ring structure include a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrimidine ring, a pyrrole ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an imidazoline ring, and a pyrazole ring. , isoxazole ring, thiazole ring, isothiazole ring, cyclohexadiene ring, cyclohexene ring, cyclopentadiene ring, cycloheptatriene ring, cycloheptadiene ring, cycloheptene ring, furan ring, Thiophene ring, sidine ring, quinoline ring, quinoline ring, etc. For example, a ring formed by condensing a plurality of rings such as a phenanthrene ring or a biterphenylene ring may be formed. The number of rings included in the group represented by the general formula (7) may be selected within a range of 3 to 5, or may be selected within a range of 5 to 7. The substituents that can be used for R ⁴¹ to R ⁴⁸ include the above substituent group B, preferably an unsubstituted alkyl group having 1 to 10 carbons or an unsubstituted alkyl group having 1 to 10 carbons. An aryl group having 6 to 10 carbon atoms substituted by a substituted alkyl group. In a preferred aspect of the present invention, R ⁴¹ -R ⁴⁸ are hydrogen atoms or unsubstituted alkyl groups with 1-10 carbons. In a preferred aspect of the present invention, R ⁴¹ -R ⁴⁸ are hydrogen atoms or unsubstituted aryl groups with 6-10 carbons. In a preferred aspect of the present invention, R ⁴¹ to R ⁴⁸ are all hydrogen atoms. In the general formula (7), * represents a bonding position.

In a preferred aspect of the present invention, azabenzene derivatives are used as delayed fluorescent materials. In a preferred aspect of the present invention, the azabenzene derivative has an azabenzene structure in which three of the carbon atoms are substituted with nitrogen atoms in the ring skeleton of the benzene ring. For example, azabenzene derivatives having a 1,3,5-trismazonium structure can be preferably selected. In a preferred aspect of the present invention, the azabenzene derivative has a ring skeleton of a benzene ring to form an azabenzene structure in which two of the carbon atoms are substituted with nitrogen atoms. For example, azabenzene derivatives having a pyrimidine structure, a pyrimidine structure, and a pyrimidine structure can be mentioned, and azabenzene derivatives having a pyrimidine structure can be preferably selected. In one aspect of the present invention, the azabenzene derivative has a pyridine structure in which one of the carbon atoms is substituted with a nitrogen atom in the ring skeleton of the benzene ring.

在通式（8）中，Y ¹、Y ²及Y ³表示至少一個為氮原子且其餘部分為次甲基。在本發明的一態樣中，Y ¹為氮原子且Y ²及Y ³為次甲基。較佳為，Y ¹及Y ²為氮原子且Y ³為次甲基。更佳為，Y ¹～Y ³均為氮原子。 在通式（8）中，Z ¹～Z ³分別獨立地表示氫原子或取代基，但是至少一個為供體基團的取代基。供體基團的取代基表示哈米特的σp值為負的基團。較佳為，Z ¹～Z ³中的至少一個為包含二芳基胺基結構（與氮原子鍵結之兩個芳基可以彼此鍵結）之基團，更佳為上述通式（6）所表示之基團，例如為上述通式（7）所表示之基團。在本發明的一態樣中，Z ¹～Z ³中的僅一個為通式（6）或（7）所表示之基團。在本發明的一態樣中，Z ¹～Z ³中的僅兩個分別獨立地為通式（6）或（7）所表示之基團。在本發明的一態樣中，Z ¹～Z ³均分別獨立地為通式（6）或（7）所表示之基團。關於通式（6）及通式（7）的詳細內容和較佳範圍，能夠參照上述對應之記載。不是通式（6）及通式（7）所表示之基團的其餘的Z ¹～Z ³為經取代或未經取代的芳基（例如，碳數6～40、較佳為6～20）為較佳，作為在此所述之芳基的取代基，可以例示出選自包括芳基（例如，碳數6～20、較佳為6～14）及烷基（例如，碳數1～20、較佳為1～6）之群組中的一個基團或兩個以上組合而獲得之基團。在本發明的一態樣中，通式（8）不包含氰基。 In a preferred aspect of the present invention, a compound represented by the following general formula (8) is used as a delayed fluorescent material. [chemical formula 16]

In the general formula (8), Y ¹ , Y ² and Y ³ represent that at least one is a nitrogen atom and the rest are methine groups. In one aspect of the invention, Y ¹ is a nitrogen atom and Y ² and Y ³ are methine. Preferably, Y ¹ and Y ² are nitrogen atoms and Y ³ is a methine group. More preferably, Y ¹ to Y ³ are all nitrogen atoms. In the general formula (8), Z ¹ to Z ³ each independently represent a hydrogen atom or a substituent, but at least one is a substituent of a donor group. The substituent of the donor group represents a group having a negative Hammett's σp value. Preferably, at least one of Z ¹ to Z ³ is a group containing a diarylamine structure (two aryl groups bonded to nitrogen atoms can be bonded to each other), more preferably the above general formula (6) The group represented is, for example, a group represented by the above general formula (7). In one aspect of the present invention, only one of Z ¹ to Z ³ is a group represented by general formula (6) or (7). In one aspect of the present invention, only two of Z ¹ to Z ³ are independently groups represented by general formula (6) or (7). In one aspect of the present invention, Z ¹ to Z ³ are each independently a group represented by general formula (6) or (7). For details and preferred ranges of the general formula (6) and the general formula (7), reference can be made to the corresponding description above. The remaining Z ¹ to Z ³ other than the groups represented by general formula (6) and general formula (7) are substituted or unsubstituted aryl groups (for example, carbon number 6-40, preferably 6-20 ) is preferred. As the substituent for the aryl group described here, examples include aryl (for example, carbon number 6 to 20, preferably 6 to 14) and alkyl (for example, carbon number 1 ～20, preferably 1～6) one group or a combination of two or more groups. In one aspect of the present invention, the general formula (8) does not contain a cyano group.

在通式（9）中，Ar ¹形成可以取代為下述A ¹及D ¹的環狀結構，並且表示苯環、萘環、蒽環或菲環。Ar ²、Ar ³可以分別形成環狀結構，在形成環狀結構之情況下，表示苯環、萘環、吡啶環或經氰基取代之苯環。m1表示0～2中的任一個整數，m2表示0～1中的任一個整數。A ¹表示氰基、苯基、嘧啶基、三唑基或苯甲腈基。D ¹表示經取代或未經取代的5H-吲哚并[3,2,1-de]啡𠯤-5-基或者不包含萘結構的經取代或未經取代的雜環縮合咔唑基，在通式（9）中存在複數個D ¹之情況下，它們可以相同，亦可以不同。又，D ¹的取代基可以彼此鍵結而形成環狀結構。 In a preferred aspect of the present invention, a compound represented by the following general formula (9) is used as a delayed fluorescent material. [chemical formula 17]

In the general formula (9), Ar ¹ forms a ring structure which may be substituted with the following A ¹ and D ¹ , and represents a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. Ar ² and Ar ³ may each form a ring structure, and when they form a ring structure, they represent a benzene ring, a naphthalene ring, a pyridine ring, or a cyano-substituted benzene ring. m1 represents any integer of 0-2, and m2 represents any integer of 0-1. A ¹ represents a cyano group, a phenyl group, a pyrimidinyl group, a triazolyl group or a benzonitrile group. D ¹ represents a substituted or unsubstituted 5H-indolo[3,2,1-de]indole-5-yl or a substituted or unsubstituted heterocyclic condensed carbazolyl group that does not contain a naphthalene structure, When a plurality of D ¹ exist in the general formula (9), they may be the same or different. In addition, the substituents of ^D1 may be bonded to each other to form a ring structure.

In the following, preferred compounds that can be used as delayed fluorescent materials are listed, but the delayed fluorescent materials that can be used in the present invention are not limitedly interpreted by these specific examples. [chemical formula 18]

In a preferred aspect of the present invention, a compound represented by the following general formula (E) is used as a delayed fluorescent material. The general formula (E) includes the above-mentioned TADF3 or TADF72. general formula (E) [chemical formula 19]

In the general formula (E), R ¹ to R ⁴ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. Also, two or more of R ¹ to R ⁴ are donor groups, and at least one of the two or more donor groups is a substituted ring-condensed carbazol-9-yl group. X ¹ to X ³ each independently represent N or C (R), but at least one of X ¹ to X ³ is N. R represents a hydrogen atom, a deuterium atom or a substituent. Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group. L ¹ represents a single bond or a divalent linking group.

In one aspect of the present invention, at least one of R ¹ to R ⁴ is a hydrogen atom or a deuterium atom. In a preferred aspect of the present invention, only one of R ¹ -R ⁴ is a hydrogen atom or a deuterium atom. In a preferred aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ² is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ³ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ⁴ is a hydrogen atom or a deuterium atom. In a preferred aspect of the present invention, only R ¹ is a hydrogen atom or a deuterium atom. In one aspect of the invention, only R ² is a hydrogen atom or a deuterium atom. In one aspect of the invention, only ^R3 is a hydrogen atom or a deuterium atom. In one aspect of the invention, only R ⁴ is a hydrogen atom or a deuterium atom. In one aspect of the invention, R ¹ is substituted or unsubstituted alkyl. In one aspect of the invention, R ² is substituted or unsubstituted alkyl. In one aspect of the invention, R ³ is substituted or unsubstituted alkyl. In one aspect of the invention, R ⁴ is substituted or unsubstituted alkyl. In one aspect of the invention, R ¹ is substituted or unsubstituted aryl. In one aspect of the invention, R ² is substituted or unsubstituted aryl. In a preferred aspect of the present invention, R ³ is substituted or unsubstituted aryl. In one aspect of the invention, R ⁴ is substituted or unsubstituted aryl.

In a preferred aspect of the present invention, two of R ¹ to R ⁴ are donor groups, one is a hydrogen atom or a deuterium atom, and one is a substituted or unsubstituted aryl group. More preferably, two of R ¹ to R ⁴ are substituted ring-condensed carbazol-9-yl groups, one is a hydrogen atom or a deuterium atom, and one is an unsubstituted aryl group. More preferably, two of R ¹ to R ⁴ are ring-condensed carbazol-9-yl groups substituted by alkyl or aryl groups, one is a hydrogen atom or a deuterium atom, and one is an unsubstituted phenyl group. In one aspect of the present invention, three of R ¹ to R ⁴ are donor groups, and one is a hydrogen atom or a deuterium atom. In one aspect of the present invention, three of R ¹ to R ⁴ are donor groups, and one is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). In one aspect of the present invention, three of R ¹ to R ⁴ are ring-condensed carbazol-9-yl groups substituted by alkyl or aryl groups, and one is a hydrogen atom or a deuterium atom. In one aspect of the present invention, three of R ¹ to R ⁴ are ring-condensed carbazol-9-yl substituted by alkyl or aryl, and one is substituted or unsubstituted aryl (preferably for unsubstituted aryl). In one aspect of the present invention, R ¹ to R ⁴ are all donor groups. In one aspect of the present invention, R ¹ to R ⁴ are all ring-condensed carbazol-9-yl groups substituted by alkyl or aryl groups.

In one aspect of the invention, R ¹ and R ² are donor groups. In one aspect of the invention, R ¹ and R ³ are donor groups. In one aspect of the invention, R ¹ and R ⁴ are donor groups. In one aspect of the invention, R ² and R ³ are donor groups. In one aspect of the invention, ^R3 and ^R4 are donor groups. In one aspect of the invention, R ¹ and R ² and R ³ are donor groups. In one aspect of the invention, R ¹ and R ² and R ⁴ are donor groups. In one aspect of the invention, R ¹ and R ³ and R ⁴ are donor groups. In one aspect of the invention, R ² and R ³ and R ⁴ are donor groups. In a preferred aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, R ² and R ⁴ are donor groups (preferably ring-condensed carbazole-9- group), R ³ is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). In one aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, R ² and R ⁴ are donor groups (preferably ring-condensed carbazol-9-yl substituted by alkyl or aryl), R ³ is a substituted or unsubstituted alkyl group (preferably an unsubstituted alkyl group). In one aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, R ² and R ⁴ are donor groups (preferably ring-condensed carbazol-9-yl substituted by alkyl or aryl), R ³ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ¹ is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group), R ² and R ⁴ are donor groups (preferably an alkyl group Or aryl-substituted ring condensation carbazol-9-yl), R ³ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, and R ² to R ⁴ are donor groups. In one aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, and R ² to R ⁴ are ring-condensed carbazol-9-yl groups substituted by alkyl or aryl groups. In one aspect of the present invention, R ¹ is a hydrogen atom or a deuterium atom, R ² and R ⁴ are ring-condensed carbazol-9-yls substituted by alkyl or aryl groups, and R ³ is other donor groups. In a preferred aspect of the present invention, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ are not bonded to each other to form a ring structure.

In a preferred aspect of the present invention, the compound represented by the general formula (E) is selected from the following compound groups. Compounds can be selected from Group 1, Group 2, Group 3, Group 4, Group 5, Group 6, or Choose from Group 7, choose from Group 8, choose from Group 9, choose from Group 10, choose from Group 11, choose from Group 12, or choose from Group 13Make a selection. [chemical formula 20]

In the present invention, in addition to the above, a known delayed fluorescent material and a compound represented by the general formula (1) can also be used in appropriate combination. In addition, even unknown delayed fluorescent materials can be used. Examples of delayed fluorescent materials include paragraphs 0008 to 0048 and paragraphs 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, and paragraphs 0007 to 0033 of WO2013/011955. paragraphs and 0059-0066, paragraphs 0008-0071 and 0118-0133 of WO2013/081088, paragraphs 0009-0046 and 0093-0134 of JP-A-2013-256490, JP-A-2013-116975 0008-0020 and 0038-0040 of WO2013/133359, 0007-0032 and 0079-0084 of WO2013/133359, 0008-0054 and 0101-0121 of WO2013/161437, JP-A-2014-9352 Paragraphs 0007-0041 and 0060-0069 of the communique, paragraphs 0008-0048 and 0067-0076 of the Japanese Patent Application Publication No. 2014-9224, paragraphs 0013-0025 of the Japanese Patent Application Publication No. 2017-119663, Japanese Patent Application Publication No. 2017- Paragraphs 0013-0026 of JP-A-119664, paragraphs 0012-0025 of JP-A-2017-222623, paragraphs 0010-0050 of JP-A-2017-226838, paragraphs 0012-0043 of JP-A-2018-100411 , Compounds included in the general formula described in paragraphs 0016 to 0044 of WO2018/047853, especially exemplary compounds and radiation-delayed fluorescence. In addition, JP-A-2013-253121, WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895, WO2014/126200, WO2014/136758, WO2014/133121, WO2014/136860, WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580, WO2014/203840, WO2015/002 Bulletin No. 213, WO2015/ 016200, WO2015/019725, WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537, WO2015/080183, JP-A-2015-129240 Bulletin, WO2015 /129714 Gazette, WO2015/129715 Gazette, WO2015/133501 Gazette, WO2015/136880 Gazette, WO2015/137244 Gazette, WO2015/137202 Gazette, WO2015/137136 Gazette, WO2015/146541 Gazette 、WO2015/159541 The luminescent material described in the Publication No. 1 and radiated delayed fluorescence. In addition, the above-mentioned gazette described in this paragraph is incorporated here as a part of this specification.

It is preferable that the delayed fluorescent material used in the present invention does not contain metal atoms. For example, as the delayed fluorescent 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 the delayed fluorescent 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 fluorescent material, a compound composed of carbon atoms, hydrogen atoms, and nitrogen atoms can be selected.

In addition, unless otherwise specified, the alkyl group, alkenyl group, aryl group, heteroaryl group, etc. in this specification represent the following content. "Alkyl" may be linear, branched, or cyclic. In addition, two or more types of linear moieties, cyclic moieties, and branched moieties may be present in admixture. The carbon number of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, n-pentyl, isopentyl, n-hexyl, isohexyl , 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, cyclopentyl, cyclohexyl, cycloheptyl. The alkyl group of the substituent may be further substituted with an aryl group. Regarding the alkyl part of "alkoxy", "alkylthio", "acyl" and "alkoxycarbonyl", the description of "alkyl" mentioned here can also be referred to. "Alkenyl" may be linear, branched, or cyclic. In addition, two or more types of linear moieties, cyclic moieties, and branched moieties may be present in admixture. The carbon number of the alkenyl group can be, for example, 2 or more, 4 or more. In addition, the carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of alkenyl include vinyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, 2-ethenyl Hexenyl. The alkenyl group of the substituent may be further substituted with a substituent. "Aryl" and "heteroaryl" may be a single ring or may be a condensed ring formed by condensing two or more rings. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example. Specific examples of the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a biphenylene ring, a quinoline ring, a pyridine ring, a quinoline ring, Hedidine ring. Specific examples of aryl or heteroaryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridyl, 3-pyridine Base, 4-pyridyl. The "aryl" and "heteroaryl" can be those in which the valences in the descriptions of the aryl and heteroaryl are replaced with 2. Regarding the aryl moiety of "aryloxy", "arylthio", and "aryloxycarbonyl", the description of "aryl" mentioned here can also be referred to. Regarding the heteroaryl moiety of "heteroaryloxy", "heteroarylthio", and "heteroaryloxycarbonyl", reference can also be made to the description of "heteroaryl" mentioned here.

(composition) The composition of the present invention includes a compound represented by general formula (1) and a delayed fluorescent material. In one aspect of the present invention, the composition consists of only one or more compounds represented by the general formula (1) and one or more delayed fluorescent materials. In one aspect of the present invention, the composition consists of only one compound represented by general formula (1) and one delayed fluorescent material. In one aspect of the present invention, the composition contains the third component in addition to the compound represented by the general formula (1) and the delayed fluorescent material. The third component mentioned here is not a compound represented by the general formula (1), nor is it a retarded fluorescent material. The 3rd component may contain only 1 type, and may contain 2 or more types. The content of the third component in the composition can be selected within the range of 30% by weight or less, or can be selected within the range of 10% by weight or less, or can be selected within the range of 1% by weight or less. Select within the range of 0.1% by weight or less. In one aspect of the present invention, the third component does not emit light. In one aspect of the present invention, the third component emits fluorescent light. In a preferred aspect of the present invention, the largest component of the luminescence from the composition of the present invention is fluorescence (including delayed fluorescence). In the composition of the present invention, the content of the compound represented by the general formula (1) is higher than that of the delayed fluorescent material on a weight basis. The content of the compound represented by the general formula (1) can be selected within the range of 3 weight times or more of the content of the retarded fluorescent material, or can be selected within the range of 10 weight times or more, or can be selected at 100 weight times or more It can be selected within the range of 1000 times by weight or more, and for example, it can be selected within the range of 10000 times by weight or less. In the composition of the present invention, it is preferable to select a delayed fluorescent material having an excited singlet energy smaller than that of the compound represented by the general formula (1). The difference in excited singlet energy may be 0.1 eV or more, 0.3 eV or more, or 0.5 eV or more, and may be 2 eV or less, 1.5 eV or less, or 1.0 eV or less. It is preferable that the composition of the present invention does not contain metal elements. In one aspect of the present invention, the composition of the present invention consists only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms and halogen atoms. In one aspect of the present invention, the composition of the present invention consists only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

Also, in one aspect of the present invention, the compound represented by the general formula (1) is used as a host material for use with a delayed fluorescent material and a fluorescent compound. Therefore, in one aspect of the present invention, the composition of the present invention contains a fluorescent compound in addition to the compound represented by the general formula (1) and the delayed fluorescent material.

It is preferable that the lowest excited singlet energy ( _ES1 ) of the fluorescent compound is smaller than that of the compound represented by the general formula (1) and the delayed fluorescent material. The fluorescent compound receives energy from the compound represented by the general formula (1) in the excited singlet state and the delayed fluorescent material, and the delayed fluorescent material in which the excited triplet state undergoes inverse intersystem transition to the excited singlet state and transitions to the singlet state Fluorescent emission upon return to the ground state in the excited state. The fluorescent compound is not particularly limited as long as it receives energy from the compound represented by the general formula (1) and the delayed fluorescent material and can radiate fluorescent light. The light emission may be fluorescent or delayed fluorescent. Light. Among them, it is preferable that the luminescent material used as a fluorescent compound radiates fluorescence when returning from the lowest excited singlet state energy level to the ground state energy level. Two or more kinds of fluorescent compounds can be used. For example, a desired color can be emitted by simultaneously using two or more fluorescent compounds having different emission colors. As the fluorescent compound, anthracene derivatives, pyrene derivatives, pyrene derivatives, pyrene derivatives, perylene derivatives, pyrene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, and pyrene derivatives can be used. Derivatives, stilbene derivatives, stilbene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives , quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julonidine derivatives, thiazole derivatives, derivatives with metals (Al, Zn) Compounds with multiple resonance effects, such as compounds with boron-containing polycyclic aromatic skeletons, such as diazaboronaphthoanthracene, etc. These exemplary skeletons may or may not have a substituent. Also, these exemplary skeletons may be combined with each other.

As a specific example of a fluorescent compound, the compound mentioned as a specific example of a delayed fluorescent material is mentioned. At this time, the composition of the present invention contains two or more delayed fluorescent materials, but the one with the higher lowest excited singlet energy functions as an auxiliary dopant, and the one with the lower lowest excited singlet energy acts as the main fluorescent material that emits light. Sexual compounds play a role. The compound used as a fluorescent compound preferably has a PL emission quantum yield of 60% or more, more preferably 80% or more. Also, the compound used as a fluorescent compound preferably exhibits a transient fluorescence lifetime of 50 ns or less, more preferably 20 ns or less. The instantaneous fluorescence lifetime in this case refers to the luminescence lifetime of the fastest-decaying component among a plurality of exponentially decaying components observed when measuring the luminescence lifetime of a compound showing thermally active delayed fluorescence. Also, the compound used as the third compound preferably has a fluorescence radiation velocity from the lowest excited singlet state (S1) to the ground state greater than an intersystem crossing velocity from S1 to the lowest excited triplet state (T1). For the calculation method of the rate constant of the compound, it is possible to refer to the known literature related to thermally active delayed fluorescent materials (H. Uoyama, et al., Nature 492 , 234 (2012) or K. Masui, et al., Org . Electron. 14 , 2721, (2013) et al).

In the following, preferable compounds that can be used as the fluorescent compound used together with the delayed fluorescent material are listed, but the fluorescent compound that can be used in the present invention is not limitedly interpreted by these specific examples.

[chemical formula 21]

Moreover, the compounds described in paragraphs 0220 to 0239 of WO2015/022974 can also be particularly preferably used as the fluorescent compound of the present invention.

In a preferred aspect of the present invention, a compound represented by the following general formula (G) is used in the light-emitting layer. The compound represented by the general formula (G) is preferably used as a fluorescent compound used in combination with a delayed fluorescent material (auxiliary dopant). The fluorescent compound described here is a concept including both a fluorescent compound with radiation-delayed fluorescence and a fluorescent compound without radiation-delayed fluorescence, but a fluorescent compound with radiation-delayed fluorescence is preferred . The compound represented by the general formula (G) can be used as an auxiliary dopant. General formula (G) [Chemical formula 22]

In the general formula (G), one of X ¹ and X ² is a nitrogen atom, and the other is a boron atom. In one aspect of the present invention, X ¹ is a nitrogen atom, and X ² is a boron atom. At this time, ^R17 and ^R18 are bonded to each other to form a single bond to form a pyrrole ring. In another aspect of the present invention, X ¹ is a boron atom, and X ² is a nitrogen atom. At this time, ^R21 and ^R22 are bonded to each other to form a single bond to form a pyrrole ring.

In the general formula (G), R ¹ to R ²⁶ , A ¹ , and A ² each independently represent a hydrogen atom, a deuterium atom, or a substituent. R ¹ and R ² , R 2 and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , ^{R 9} and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R 14 , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 17 and} R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R 21 and R 22 , R ²² and R ²³ , R ²³ and R ²⁴ , ^{R 24 and} R ^{25 ,} R ²⁵ and R ²⁶ may be bonded to each other to form a ring shape structure. The ring structure formed by bonding R ⁷ and R ⁸ contains a boron atom and four carbon atoms as ring skeleton constituent atoms. When X ¹ is a boron atom, the ring structure formed by bonding R ¹⁷ and R ¹⁸ includes a boron atom and four carbon atoms as ring skeleton constituent atoms. When X ¹ is a nitrogen atom, the ring structure is limited to a pyrrole ring. When X ² is a boron atom, the ring structure formed by bonding R ²¹ and R ²² includes a boron atom and four carbon atoms as ring skeleton constituent atoms. When X ² is a nitrogen atom, the ring structure is limited to a pyrrole ring. When R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ , R ²¹ and R ²² are bonded to each other to form a ring structure containing boron atoms, the ring structure is preferably a 5-7-membered ring, 5 or 6-membered A ring is more preferred, and a 6-membered ring is further preferred. When R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ , R ²¹ and R ²² are bonded to each other, they are bonded to each other to form a single bond, -O-, -S-, -N(R ²⁷ )-, -C( R ²⁸ )(R ²⁹ )-, -Si(R ³⁰ )(R ³¹ )-, -B(R ³² )-, -CO-, -CS- are preferred, forming -O-, -S- or - N(R ²⁷ )- is more preferred, and -N(R ²⁷ )- is further preferred. Wherein, R ²⁷ to R ³² each independently represent a hydrogen atom, a deuterium atom or a substituent. As a substituent, a group selected from any of the substituent groups A to E described below can be used, but a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Substituted heteroaryl is preferred, and R ²⁷ is particularly preferred as substituted or unsubstituted aryl. When R ²⁷ to R ³² are substituents, R ²⁷ to R ³² in the ring formed by bonding R ⁷ and R ⁸ to each other may bond to at least one of R ⁶ and R ⁹ to further form a ring structure , R ¹⁷ and R ¹⁸ are bonded to each other and R ²⁷ to R ³² in the ring formed by bonding to each other may bond to at least one of R ¹⁶ and R ¹⁹ to further form a ring structure, and R ²¹ and R ²² are bonded to each other to form a ring structure R ²⁷ to R ³² in the formed ring may be bonded to at least one of R ²⁰ and R ²³ to further form a ring structure. In one aspect of the present invention, only one group of R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ , R ²¹ and R ²² are bonded to each other. In one aspect of the present invention, only two groups of R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ , R ²¹ and R ²² are bonded to each other. In one aspect of the present invention, R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ , R ²¹ and R ²² are all bonded to each other.

R ¹ and R ² , R 2 and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ⁹ and R ¹⁰ , ^{R 10} and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , R ¹⁴ and R 15 , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁸ and R ¹⁹ , ^{R 19 and} R ²⁰ , R ²⁰ and R ²¹ , R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ are bonded to each other to form a ring structure that may be an aromatic ring or an aliphatic ring, and may contain hetero In the case of atoms, other rings having one or more rings may be condensed. As the hetero atom mentioned here, one selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom is preferable. Examples of the formed ring structure include a benzene ring, a pyridine ring, a pyridine ring, a pyrimidine ring, a pyridine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, and a furan ring. , Thiophene ring, azole ring, isoxazole ring, thiazole ring, isothiazole ring, cyclohexadiene ring, cyclohexene ring, cyclopentene ring, cycloheptatriene ring, cycloheptadiene ring, cycloheptadiene ring An alkene ring and a ring formed by further condensation of one or more rings selected from the group including these rings. In a preferred aspect of the present invention, the ring structure is a substituted or unsubstituted benzene ring (rings may also be condensed), such as a benzene ring that may be substituted by an alkyl or aryl group. In a preferred aspect of the present invention, the ring structure is a substituted or unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran and a thiophene ring of benzothiophene. R ¹ and R ² , R 2 and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ⁹ and R ¹⁰ , ^{R 10} and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , R ¹⁴ and R 15 , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , R ¹⁸ and R ¹⁹ , ^{R 19 and} R ²⁰ , R ²⁰ and R ²¹ , R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ are bonded to each other to form a ring structure. The number of combinations may be 0, for example, may be 1 to 6 any of the . For example, any one of 1 to 4 may be used, and 1, 2, or 3 or 4 may be selected. In one aspect of the present invention, one group selected from R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ are bonded to each other to form a ring structure. In one aspect of the present invention, R ⁵ and R ⁶ are bonded to each other to form a ring structure. In one aspect of the present invention, one group selected from R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , and R ¹¹ and R ¹² are bonded to each other to form a ring structure. In one aspect of the present invention, R ¹ and R ² , R ¹³ and R ¹⁴ are all bonded to each other to form a ring structure. In one aspect of the present invention, a group selected from R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ are bonded to each other to form a ring structure, and R ⁵ and R ⁶ are bonded to each other to form a ring structure. In one aspect of the present invention, R ⁵ and R ⁶ , R ¹⁹ and R ²⁰ are all bonded to each other to form a ring structure.

R ¹ to R ²⁶ that are not bonded to adjacent R ⁿ (n=1 to 26) are hydrogen atoms, deuterium atoms or substituents. As a substituent, a group selected from any one of substituent groups A to E described below can be used. Preferred substituents for R ¹ to R ²⁶ are substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, for example, the substituents can be Substituted or unsubstituted aryl, for example the substituent may also be substituted or unsubstituted alkyl. The substituents of the alkyl, aryl, and heteroaryl groups described here can also be selected from any one of the substituent groups A to E, but are preferably selected from groups including alkyl, aryl, and One or more groups in the group of heteroaryl groups, more preferably groups of substituent group E, may also be unsubstituted. In a preferred aspect of the present invention, at least one of R ¹ to R ⁶ is a substituent, preferably a substituent group E group. For example, at least one of R ² to R ⁶ is a substituent, preferably a substituent group E group. For example, at least one of R ⁵ and R ⁶ is a substituent, preferably a group of substituent group E. In a preferred aspect of the present invention, at least one of R ³ and R ⁶ is a substituent, more preferably both are substituents, and are preferably a group of substituent group E. In a preferred aspect of the present invention, when X ¹ is a nitrogen atom, at least one of R ¹⁵ and R ²⁰ is a substituent, more preferably both are substituents, and preferably a group of substituents E group. At this time, R ¹⁷ and R ¹⁸ are bonded to each other to form a single bond. In a preferred aspect of the present invention, when X ² is a nitrogen atom, at least one of R ¹⁹ and R ²⁴ is a substituent, more preferably both are substituents, and preferably a group of substituents E group. At this time, ^R21 and ^R22 are bonded to each other to form a single bond. In one aspect of the present invention, at least one of R ⁸ and R ¹² is a substituent, preferably both are substituents. In one aspect of the present invention, R ⁸ , R ¹⁰ and R ¹² are substituents. As substituents for R ⁸ to R ¹² , unsubstituted alkyl groups are preferred. In particular, R ⁸ and R ¹² 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, further preferably 3 or 4 alkyl groups ) is preferable since the orientation becomes high when it is formed into a film. Among them, R ⁸ and R ¹² are substituents (preferably an alkyl group, more preferably an alkyl group with 2 or more carbons, more preferably an alkyl group with 3 or more carbons, even more preferably an alkyl group with 3 to 8 carbons An alkyl group, particularly preferably an alkyl group of 3 or 4) and at least one of R ¹ to R ⁶ is a substituent (preferably a group of substituent group E) is particularly preferred. When ^X1 is a boron atom, at least one of ^R13 and ^R17 is a substituent, preferably both are substituents. In one aspect of the present invention, when X ¹ is a boron atom, R ¹³ , R ¹⁵ and R ¹⁷ are substituents. When X ¹ is a boron atom, unsubstituted alkyl groups are preferred as substituents for R ¹³ to R ¹⁷ . When X ² is a boron atom, at least one of R ²² and R ²⁶ is a substituent, preferably both are substituents. In one aspect of the present invention, when X ² is a boron atom, R ²² , R ²⁴ and R ²⁶ are substituents. When X ² is a boron atom, unsubstituted alkyl groups are preferred as substituents for R ²² to R ²⁶ . Specific examples of the group bonded to the boron atom represented by B in the general formula (G) or the boron atom represented by ^X1 or ^X2 are given below. Among them, the groups bonded to boron atoms that can be used in the present invention are not limitedly interpreted by the following specific examples. In addition, in this specification, the representation of CH ₃ is omitted for the methyl group. * Indicates bond position. [chemical formula 23]

Specific examples of R ¹ to R ²⁶ in the general formula (G) are given below. R ¹ to R ⁷ and R ¹³ to R ²¹ when X ¹ is a nitrogen atom, and R ¹⁸ to R ²⁶ when X ² is a nitrogen atom are preferably Z1 to Z9, and R ⁸ to R ¹² and X ¹ are R ²² to R ²⁶ in the case of a nitrogen atom, and R ¹³ to R ¹⁷ in the case of a nitrogen atom when X ² is a nitrogen atom, Z1 to Z7 are preferred. Among them, the groups bonded to boron atoms that can be used in the present invention are not limitedly interpreted by the following specific examples. D represents a deuterium atom. * Indicates bond position. [chemical formula 24]

^A1 and ^A2 are a hydrogen atom, a deuterium atom or a substituent. As a substituent, a group selected from any one of substituent groups A to E described below can be used. In a preferred aspect of the present invention, A ¹ and A ² 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 may be a substituent. Also, ^A1 and ^A2 may each independently be a substituent. A preferred substituent that ^A1 and ^A2 can adopt is an acceptor group. The acceptor group is a group with a positive Hammett's σp value. The acceptable acceptor groups for A ¹ and A ² are more preferably groups whose Hammett's σp value is greater than 0.2. As groups having a Hammett's σp value greater than 0.2, cyano groups, aryl groups substituted by at least cyano groups, groups containing fluorine atoms, substituted or unsubstituted groups containing nitrogen atoms as ring skeleton constituent atoms, The heteroaryl. The at least cyano-substituted aryl group described herein may be substituted with substituents other than cyano (eg, alkyl or aryl), but may also be an aryl group substituted only with cyano. Preferably, the aryl group substituted with at least cyano group is phenyl group substituted with at least cyano group. The number of substitutions of the cyano group is preferably one or two, for example, one or two. Examples of the group containing a fluorine atom include a fluorine atom, a fluorinated alkyl group, a fluorine atom, or an aryl group substituted with at least a fluorinated alkyl group. The fluorinated alkyl group is preferably a perfluoroalkyl group, preferably having 1-6 carbon atoms, more preferably 1-3 carbon atoms. In addition, the heteroaryl group containing a nitrogen atom as a ring skeleton constituting atom may be a single ring or a condensed ring formed by condensing two or more rings. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, for example, can be selected from 2 to 4 or set to two. Specific examples of the ring constituting the heteroaryl group include a pyridine ring, a pyrimidine ring, a pyridine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoline ring, a quinoline ring, and a quinoline ring. A phenidine ring other than a phenoline ring and a quinoline ring. The ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent. As the substituent, for example, one group selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group or a combination of two or more groups may be mentioned. group. As the acceptor group that ^A1 and ^A2 can adopt, a cyano group is particularly preferable. In one aspect of the present invention, at least one of ^A1 and ^A2 is an acceptor group. In one aspect of the invention, only one of ^A1 and ^A2 is an acceptor group. In one aspect of the present invention, both ^A1 and ^A2 are the same acceptor group. In one aspect of the invention, A ¹ and A ² are different acceptor groups from each other. In one aspect of the present invention, A ¹ and A ² are cyano groups. In one aspect of the present invention, A ¹ and A ² are halogen atoms, such as bromine atoms.

Specific examples of acceptor groups that can be used in the present invention are shown below. Among them, the acceptor groups that can be used in the present invention are not limitedly interpreted by the following specific examples. In this specification, the representation of CH ₃ is omitted for the methyl group. Therefore, for example, A15 represents a group containing two 4-methylphenyl groups. Also, "D" represents a deuterium atom. * Indicates bond position. [chemical formula 25]

Furthermore, when ^X1 is a nitrogen atom, ^R7 and ^R8 are bonded via a nitrogen atom to form a 6-membered ring, ^R21 and ^R22 are bonded via a nitrogen atom to form a 6-membered ring, and ^R17 and ^R18 are bonded to each other When forming a single bond, at least one ^of R ¹ to R ⁶ is a substituted or unsubstituted aryl group or R ¹ and R ² , R ² and R 3 , R ³ and R ⁴ , R ⁴ and R ⁵ , Any one of R ^{and R} is bonded to each other to form an aromatic ring (substituted or unsubstituted benzene ring that can be condensed) or a heteroaromatic ring (preferably substituted or unsubstituted benzo that can be condensed) furan ring of furan, thiophene ring of substituted or unsubstituted benzothiophene which can be condensed). In addition, when X ¹ is a boron atom, X ² is a nitrogen atom, and R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ are bonded to each other to form a ring structure containing a boron atom, the ring structure is 5 to 7 In the case of a 6-membered ring, R ⁷ and R ⁸ , R ¹⁷ and R ¹⁸ are bonded to each other to form -B(R ³² )-, -CO-, -CS- or -N(R ²⁷ ) -. R ²⁷ preferably represents a hydrogen atom, a deuterium atom or a substituent.

When X ¹ of the general formula (G) is a nitrogen atom, the compound of the present invention has the following skeleton (1a). When X ² in the general formula (G) is a nitrogen atom, the compound of the present invention has the following skeleton (1b). [chemical formula 26]

Each hydrogen atom in the skeleton (1a) and (1b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted together with adjacent hydrogen atoms as a linking group to form a ring structure. For details, the description of R ¹ to R ²⁶ , A ¹ , and A ² corresponding to the general formula (G) can be referred to. It can be exemplified that the phenyl group bonded to the boron atom in the skeleton (1a) and (1b) is all substituted with mesityl, 2,6-diisopropylphenyl or 2,4,6- Triisopropylphenyl compounds, etc. In one aspect of the present invention, each hydrogen atom in the skeleton (1a) and (1b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (1a), compounds represented by the following general formula (1a) can be exemplified. General formula (1a) [Chemical formula 27]

In the general formula (1a), Ar ¹ to Ar ⁴ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. R ⁴¹ and R ⁴² independently represent a substituted or unsubstituted alkyl group, m1 and m2 independently represent an integer of 0 to 5, n1 and n3 independently represent an integer of 0 to 4, n2 and n4 independently ground represents an integer of 0 to 3. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. It is preferable that at least one of n1 to n4 is 1 or more, and m1 and m2 are each independently any integer of 1 to 5. In one aspect of the present invention, n1-n4 each independently represent an integer of 0-2. In a preferred aspect of the present invention, at least one of n1-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 aspect of the present invention, n1 and n3 are 1 or 2 independently, and n2 and n4 are 0. In one aspect of the present invention, n2 and n4 are 1 or 2 independently, and n1 and n3 are 0. In one aspect of the present invention, n1-n4 are 1 or 2 each independently. In one aspect of the present invention, n1 and n3 are equal, and n2 and n4 are equal. In an aspect of the present invention, n1 and n3 are 1, and n2 and n4 are 0. In an aspect of the present invention, n1 and n3 are 0, and n2 and n4 are 1. In one aspect of the present invention, n1˜n4 are all 1. The bonding positions of Ar ¹ to Ar ⁴ may be at least one of the 3 and 6 positions of the carbazole ring, or at least one of the 2 and 7 positions, or at least one of the 1 and 8 positions, or It is at least one of 4 and 5 digits. The bonding positions of Ar ¹ to Ar ⁴ may be both the 3 and 6 positions of the carbazole ring, may also be both the 2 and 7 positions, may also be both the 1 and 8 positions, or may be the 4, 8 positions. 5 bits for both. For example, at least one of 3 and 6 bits may be preferably selected, or both 3 and 6 bits may be further preferably selected. In a preferred aspect of the present invention, Ar ¹ to Ar ⁴ are all the same group. In a preferred aspect of the present invention, Ar ¹ to Ar ⁴ are independently substituted or unsubstituted aryl, more preferably substituted or unsubstituted phenyl or naphthyl, further preferably is a substituted or unsubstituted phenyl group. As the substituent, a group selected from any one of substituent groups A to E described below can be mentioned, but an unsubstituted phenyl group is also preferable. Preferable specific examples of Ar ¹ to Ar ⁴ include phenyl, o-biphenyl, m-biphenyl, p-biphenyl, and terphenyl. In one aspect of the present invention, m1 and m2 are each independently 0. In one aspect of the present invention, m1 and m2 are each independently any integer of 1-5. In one aspect of the invention, m1 and m2 are equal. In one aspect of the present invention, R ⁴¹ and R ⁴² are alkyl groups having 1 to 6 carbons, for example, can be selected from alkyl groups having 1 to 3 carbons or methyl groups. Regarding the substitution position of the alkyl group, the carbon atom bonded to the boron atom can be set as the 1st position, and examples include only the 2nd position, only the 3rd position, only the 4th position, the 3rd and 5th positions, the 2nd and 4th positions, and the 2nd positions. And 6 bits, 2 bits, 4 bits, 6 bits, etc., at least 2 bits are better, and at least 2 bits and 6 bits are more preferable. For descriptions and preferred ranges of ^A1 and ^A2 , reference can be made to the corresponding description of the general formula (G).

Specific examples of the compound represented by the general formula (1a) are given below. The compounds of the general formula (1a) that can be used in the present invention are not limitedly interpreted by the following group of specific examples. For example, a group including compounds other than the compound in the middle of the following column 4 and the middle compound in the following eighth column can be mentioned as a preferable group. [chemical formula 28]

Another specific example of the compound represented by the general formula (1a) is given below. The compounds of the general formula (1a) that can be used in the present invention are not limitedly interpreted by the following group of specific examples. [chemical formula 29]

As a preferable group of compounds having a skeleton (1b), compounds represented by the following general formula (1b) can be exemplified. General formula (1b) [Chemical formula 30]

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

Specific examples of the compound represented by the general formula (1b) are given below. The compounds of the general formula (1b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 31]

When R ⁷ and R ⁸ of the general formula (G) are bonded to each other to form N-Ph, when X ¹ is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (2a), when X ² is a nitrogen atom , the compound of the present invention has, for example, the following skeleton (2b). Ph is phenyl. Skeleton (2a) [Chemical Formula 32]

Each hydrogen atom in the skeleton (2a) and (2b) may be replaced by a deuterium atom or a substituent. In addition, it may be substituted with an adjacent hydrogen atom as a linking group to form a ring structure. For details, the description of R ¹ to R ²⁶ , A ¹ , and A ² corresponding to the general formula (G) can be referred to. At least one hydrogen atom in the benzene ring constituting the partial structure of the carbazole included in the skeleton (2a) is substituted with a substituted or unsubstituted aryl group. In one aspect of the present invention, each hydrogen atom in the skeleton (2a) and (2b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (2a), compounds represented by the following general formula (2a) can be exemplified. General formula (2a) [Chemical formula 33]

In the general formula (2a), Ar ⁹ to Ar ¹⁴ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n9, n11, n12, and n14 each independently represent an integer of 0-4, and n10 and n13 each independently represent an integer of 0-2. However, at least one of n9, n10, n12, and n13 is 1 or more. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n9-n14 each independently represent an integer of 0-2. In one aspect of the present invention, at least one of n9 to n14 is 1 or more, for example, n9 and n12 can be 1 or more, or n10 and n13 can be 1 or more. In a preferred aspect of the present invention, at least one of n9, n10, n12, and n13 is 1 or more. In one aspect of the present invention, n9 and n12 are 1 or 2 independently, and n10, n11, n13, and n14 are 0. In one aspect of the present invention, n10 and n13 are 1 or 2 independently, and n9, n11, n12, and n14 are 0. In one aspect of the present invention, n9 and n12 are 1 or 2 independently, n10 and n13 are 1 or 2 independently, and n11 and n14 are 0. In one aspect of the present invention, n9˜n14 are all 1. The bonding positions of Ar ⁹ to Ar ¹⁴ can be set at the 3rd and 6th positions of the carbazole ring or other positions. In a preferred aspect of the present invention, Ar ⁹ to Ar ¹⁴ are all the same group. For preferred groups of Ar ⁹ to Ar ¹⁴ , reference can be made to the corresponding descriptions of Ar ¹ to Ar ⁴ . For descriptions and preferred ranges of ^A1 and ^A2 , reference can be made to the corresponding description of the general formula (G).

Specific examples of the compound represented by the general formula (2a) are given below. The compounds of the general formula (2a) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 34]

As a preferable group of compounds having a skeleton (2b), compounds represented by the following general formula (2b) can be exemplified. General formula (2b) [Chemical formula 35]

In the general formula (2b), Ar ¹⁵ to Ar ²⁰ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n15, n17, n18, and n20 each independently represent an integer of 0-4, and n16 and n19 each independently represent an integer of 0-2. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of Ar ¹⁵ to Ar ²⁰ , n15 to n20, A ¹ , and A ² , the descriptions of Ar ⁹ to Ar ¹⁴ , n9 to n14, A ¹ , and A ² in the general formula (2a) can be referred to sequentially.

Specific examples of the compound represented by the general formula (2b) are given below. The compounds of the general formula (2b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 36]

When R ⁷ and R ⁸ of the general formula (G) are bonded to each other to form a single bond, when X ¹ is a nitrogen atom, the compound of the present invention has, for example, the following skeleton (3a), when X ² is a nitrogen atom, The compound of the present invention has, for example, the following skeleton (3b). [chemical formula 37]

Each hydrogen atom in the skeleton (3a) and (3b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with an adjacent hydrogen atom as a linking group to form a ring structure. For details, the description of R ¹ to R ²⁶ , A ¹ , and A ² corresponding to the general formula (G) can be referred to. In one aspect of the present invention, each hydrogen atom in the skeleton (3a) and (3b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (3a), compounds represented by the following general formula (3a) can be exemplified. General formula (3a) [Chemical formula 38]

In the general formula (3a), Ar ²¹ to Ar ²⁶ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n21, n23, n24, and n26 each independently represent an integer of 0-4, and n22 and n25 each independently represent an integer of 0-2. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of Ar ²¹ to Ar ²⁵ and n21 to n25, the descriptions of Ar ⁹ to Ar ¹⁴ , n9 to n14, A ¹ and A ² in the general formula (2a) can be referred to.

Specific examples of the compound represented by the general formula (3a) are given below. The compounds of the general formula (3a) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 39]

As a preferable group of compounds having a skeleton (3b), compounds represented by the following general formula (3b) can be exemplified. General formula (3b) [Chemical formula 40]

In the general formula (3b), Ar ²⁷ to Ar ³² independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n27, n29, n30, and n32 each independently represent an integer of 0-4, and n28 and n31 each independently represent an integer of 0-2. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of Ar ²⁷ to Ar ³² , n27 to n32, A ¹ , and A ² , the descriptions of Ar ¹⁵ to Ar ²⁰ , n15 to n20, A ¹ , and A ² in the general formula (2b) can be referred to sequentially.

Specific examples of the compound represented by the general formula (3b) are given below. The compounds of the general formula (3b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 41]

In a preferred aspect of the present invention, a compound in which the two benzene rings constituting the partial structure of the carbazole present in the general formula (G) are condensed with other rings is selected. Among them, a compound condensed with a benzofuran ring, a compound condensed with a benzothiophene ring, and a compound condensed with a benzene ring can be particularly preferably selected. In the following, specific examples will be given to describe such ring-condensed compounds.

Preferable examples include compounds in which the benzene ring to which boron atoms are not directly bonded among the two benzene rings constituting the carbazole partial structure present in the general formula (G) is condensed with a benzofuran ring or a benzothiophene ring. Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b). [chemical formula 42]

In skeletons (4a) and (4b), Y ¹ to Y ⁴ each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). The two hydrogen atoms mentioned here represent a state in which two benzene rings bonded to a boron atom are not connected to each other. It is preferable that ^Y1 and ^Y2 are the same and ^Y3 and ^Y4 are the same, but they may be different from each other. In one aspect of the present invention, Y ¹ to Y ⁴ are single bonds. In one aspect of the present invention, Y ¹ to Y ⁴ are N(R ²⁷ ). R ²⁷ represents a hydrogen atom, a deuterium atom or a substituent. Z ¹ to Z ⁴ each independently represent an oxygen atom or a sulfur atom. It is preferable that Z ¹ and Z ² are the same and Z ³ and Z ⁴ are the same, but they may be different from each other. In one aspect of the present invention, Z ¹ to Z ⁴ are oxygen atoms. At this time, the furan ring of benzofuran is condensed with the benzene ring constituting the partial structure of carbazole in (4a) and (4b). The orientation of the condensed furan ring is not limited. In one aspect of the present invention, Z ¹ to Z ⁴ are sulfur atoms. At this time, the thiophene ring of benzothiophene is condensed with the benzene ring constituting the partial structure of carbazole in (4a) and (4b). The orientation of the condensed thiophene rings is not limited. Each hydrogen atom in the skeleton (4a) and (4b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with an adjacent hydrogen atom as a linking group to form a ring structure. For details, the description of R ¹ to R ²⁶ , A ¹ , and A ² corresponding to the general formula (G) can be referred to. In one aspect of the present invention, each hydrogen atom in the skeleton (4a) and (4b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (4a), compounds represented by the following general formula (4a) can be exemplified. X in the specific examples is an oxygen atom or a sulfur atom, and compounds in which X is an oxygen atom and compounds in which X is a sulfur atom are disclosed, respectively. X in specific examples of compounds represented by other general formulas below also has the same meaning. General formula (4a) [Chemical formula 43]

In the general formula (4a), Ar ⁵¹ and Ar ⁵² independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkyl, for example, A substituted or unsubstituted aryl group is preferably selected. R ⁵¹ and R ⁵² each independently represent a substituted or unsubstituted alkyl group. m51 and m52 each independently represent the integer of 0-4. n51 and n52 each independently represent the integer of 0-2. Y ¹ to Y ⁴ each 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 each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n51 and n52 are the same number. For example, n51 and n52 can be 0, and n51 and n52 can be 1. In one aspect of the present invention, m51 and m52 are the same number. In one aspect of the present invention, m51 and m52 are integers of 0-3. For example, m51 and m52 can be 0, m51 and m52 can be 1, m51 and m52 can be 2, and m51 and m52 can be 3. For preferred groups of Ar ⁵¹ , Ar ⁵² , R ⁵¹ , R ⁵² , A ¹ , and A ² , reference can be made to Ar ¹ to Ar ⁴ , R ⁴¹ to R ⁴² , A ¹ , and A ² of the general formula (1a). corresponding records.

Specific examples of the compound represented by the general formula (4a) are given below. The compounds of general formula (4a) that can be used in the present invention are not limitedly interpreted by the following group of specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 44]

Another specific example of the compound represented by the general formula (4a) is given below. The compounds of general formula (4a) that can be used in the present invention are not limitedly interpreted by the following group of specific examples. [chemical formula 45]

As a preferable group of compounds having a skeleton (4b), compounds represented by the following general formula (4b) can be exemplified. General formula (4b) [Chemical formula 46]

In the 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, A substituted or unsubstituted aryl group is preferably selected. R ⁵³ and R ⁵⁴ each independently represent a substituted or unsubstituted alkyl group. m53 and m54 each independently represent the integer of 0-4. n53 and n54 each independently represent the integer of 0-2. Y ³ and Y ⁴ each 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 each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of Ar ⁵³ , Ar ⁵⁴ , R ⁵³ , R ⁵⁴ , m53, m54, n53, n54, A ¹ , and A ² , refer to Ar ⁵¹ , Ar ⁵² , R ⁵¹ , R ⁵² , Description of m51, m52, n51, n52, A ¹ , A ² .

Specific examples of the compound represented by the general formula (4b) are given below. The compounds of the general formula (4b) that can be used in the present invention are not limitedly interpreted by the following specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 47]

Preferable examples include compounds in which the boron atoms of the two benzene rings constituting the carbazole partial structure present in the general formula (G) are directly bonded to each other and condensed with a benzofuran ring or a benzothiophene ring. Examples of such compounds include compounds having the following skeleton (5a) and compounds having the following skeleton (5b). [chemical formula 48]

In skeletons (5a) and (5b), Y ⁵ to Y ⁸ each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). Z ⁵ to Z ⁸ each independently represent an oxygen atom or a sulfur atom. For details of Y ⁵ to Y ⁸ and Z ⁵ to Z ⁸ , refer to the corresponding descriptions of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in the skeleton (5a) and (5b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (5a), compounds represented by the following general formula (5a) can be exemplified. General formula (5a) [Chemical formula 49]

In the 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, A substituted or unsubstituted aryl group is preferably selected. R ⁵⁵ and R ⁵⁶ each independently represent a substituted or unsubstituted alkyl group. m55 and m56 each independently represent the integer of 0-4. n55 and n56 each independently represent the integer of 0-4. Y ⁵ and Y ⁶ each 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 each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n55 and n56 are integers of 0-2. For example, n55 and n56 can be 0, and n55 and n56 can be 1. In one aspect of the present invention, m51 and m52 are the same number. For details of m55 and m56, the descriptions of m51 and m52 in the general formula (4a) can be referred to. For preferred groups of Ar ⁵⁵ , Ar ⁵⁶ , R ⁵⁵ , R ⁵⁶ , A ¹ , and A ² , refer to Ar ¹ , Ar ³ , R ⁴¹ , R ⁴² , A ¹ , and A ² of general formula (1a). corresponding records.

Specific examples of the compound represented by the general formula (5a) are given below. The compounds of the general formula (5a) that can be used in the present invention are not limitedly interpreted by the following set of specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 50]

Another specific example of the compound represented by the general formula (5a) is given below. The compounds of the general formula (5a) that can be used in the present invention are not limitedly interpreted by the following set of specific examples. [chemical formula 51]

As a preferable group of compounds having a skeleton (5b), compounds represented by the following general formula (5b) can be exemplified. General formula (5b) [Chemical formula 52]

In the 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, A substituted or unsubstituted aryl group is preferably selected. R ⁵⁷ and R ⁵⁸ each independently represent a substituted or unsubstituted alkyl group. m57 and m58 each independently represent an integer of 0-4. n57 and n58 each independently represent an integer of 0-4. Y ⁷ and Y ⁸ each 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 each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of Ar ⁵⁷ , Ar ⁵⁸ , R ⁵⁷ , R ⁵⁸ , m57, m58, n57, n58, A ¹ , and A ² , refer to Ar ⁵⁵ , Ar ⁵⁶ , R ⁵⁵ , R ⁵⁶ , Description of m55, m56, n55, n56, A ¹ , A ² .

Specific examples of the compound represented by the general formula (5b) are given below. The compounds of the general formula (5b) that can be used in the present invention are not limitedly interpreted by the following set of specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 53]

Another specific example of the compound represented by the general formula (5b) is given below. The compounds of the general formula (5b) that can be used in the present invention are not limitedly interpreted by the following set of specific examples. [chemical formula 54]

Preferable examples include compounds in which both of the two benzene rings constituting the carbazole partial structure present in the general formula (G) are condensed with a benzofuran ring or a benzothiophene ring. Examples of such compounds include compounds having the following skeleton (6a) and compounds having the following skeleton (6b). [chemical formula 55]

In skeletons (6a) and (6b), Y ⁹ to Y ¹² each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). Z ⁹ to Z ¹⁶ each independently represent an oxygen atom or a sulfur atom. Z ⁹ to Z ¹⁶ are preferably the same, but may be different. In one aspect of the present invention, Z ⁹ to Z ¹⁶ are oxygen atoms. In one aspect of the present invention, Z ⁹ to Z ¹⁶ are sulfur atoms. For details of Y ⁹ to Y ¹² , reference can be made to the corresponding description of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in the skeleton (6a) and (6b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (6a), compounds represented by the following general formula (6a) can be exemplified. General formula (6a) [Chemical formula 56]

In the general formula (6a), R ⁵⁹ and R ⁶⁰ each independently represent a substituted or unsubstituted alkyl group. m59 and m60 each independently represent an integer of 0-4. Y ⁹ and Y ¹⁰ each 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 ⁹ to Z ¹² each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of R ⁵⁹ , R ⁶⁰ , m59, m60, Z ⁹ to Z ¹² , A ¹ , and A ² , refer to R ⁵⁵ , R ⁵⁶ , m55, m56, A ¹ , A ² and Description of Z ⁹ to Z ¹² in skeleton (6a).

Specific examples of the compound represented by the general formula (6a) are given below. The compounds of the general formula (6a) that can be used in the present invention are not limitedly interpreted by the following specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 57]

As a preferable group of compounds having a skeleton (6b), compounds represented by the following general formula (6b) can be exemplified. General formula (6b) [Chemical formula 58]

In the general formula (6b), R ⁶¹ and R ⁶² each independently represent a substituted or unsubstituted alkyl group. m61 and m60 each independently represent an integer of 0-4. Y ¹¹ and Y ¹² each 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 ¹³ to Z ¹⁶ each independently represent an oxygen atom or a sulfur atom. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of R ⁶¹ , R ⁶² , m61, m62, Z ¹³ to Z ¹⁶ , A ¹ , and A ² , refer to R ⁵⁹ , R ⁶⁰ , m59, m60, A ¹ , A ² and Description of Z ¹³ to Z ¹⁶ in skeleton (6b).

Specific examples of the compound represented by the general formula (6b) are given below. The compounds of the general formula (6b) that can be used in the present invention are not limitedly interpreted by the following specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 59]

Preferable examples include compounds in which benzene rings in which boron atoms are not directly bonded among the two benzene rings constituting the carbazole partial structure present in the general formula (G) 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 60]

In skeletons (7a) and (7b), Y ²¹ to Y ²⁴ each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). For details of Y ²¹ to Y ²⁴ , reference can be made to the description of Y ¹ to Y ⁴ in skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in the skeleton (7a) and (7b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (7a), compounds represented by the following general formula (7a) can be exemplified. General formula (7a) [Chemical formula 61]

In the general formula (7a), Ar ⁷¹ to Ar ⁷⁴ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n71 and n73 each independently represent the integer of 0-2. n72 and n74 each independently represent the integer of 0-4. Y ²¹ and Y ²² each 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 each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n71˜n74 are integers of 0˜2. In one aspect of the present invention, n71 and n73 are the same number, and n72 and n74 are the same number. n71 to n74 may be the same number. For example, n71 to n74 may be 0. All of n71˜n74 can be 1. Also, for example, n71 and n73 may be 0, and n72 and n74 may be 1. For preferred groups of Ar ⁷¹ to Ar ⁷⁴ , A ¹ , and A ² , reference can be made to the corresponding descriptions of Ar ¹ to Ar ⁴ , A ¹ , and A ² in the general formula (1a).

Specific examples of the compound represented by the general formula (7a) are given below. The compounds of the general formula (7a) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 62]

As a preferable group of compounds having a skeleton (7b), compounds represented by the following general formula (7b) can be exemplified. General formula (7b) [Chemical formula 63]

In the general formula (7b), Ar ⁷⁵ to Ar ⁷⁸ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n75 and n77 represent the integer of 0-2 each independently. n76 and n78 each independently represent the integer of 0-4. Y ²³ and Y ²⁴ each 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, descriptions of n71 to n74 of the general formula (7a) can be referred to in order. For preferred groups of Ar ⁷⁵ to Ar ⁷⁸ , reference can be made to the corresponding descriptions of Ar ¹ to Ar ⁴ in the general formula (1a).

Specific examples of the compound represented by the general formula (7b) are given below. The compounds of the general formula (7b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 64]

Preferable examples include compounds in which the boron atoms of the two benzene rings constituting the carbazole partial structure present in the general formula (G) are directly bonded to the benzene ring and the benzene ring is condensed. Examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b). [chemical formula 65]

In skeletons (8a) and (8b), Y ²⁵ to Y ²⁸ each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). For details of Y ²⁵ to Y ²⁸ , reference can be made to the corresponding description of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in the skeleton (8a) and (8b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (8a), compounds represented by the following general formula (8a) can be exemplified. General formula (8a) [Chemical formula 66]

In the 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, A substituted or unsubstituted aryl group is preferably selected. R ⁷¹ and R ⁷² each independently represent a substituted or unsubstituted alkyl group. m71 and m72 each independently represent the integer of 0-4. n79 and n80 each independently represent the integer of 0-4. Y ²⁵ and Y ²⁶ each 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 each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n79 and n80 are integers of 0-2. In one aspect of the present invention, n79 and n80 are the same number, for example both can be 0 or both can be 1. In one aspect of the present invention, m71 and m72 are integers of 0-2. In one aspect of the present invention, m71 and m72 are the same number, for example both can be 0 or both can be 1. For preferred groups of Ar ⁷⁹ , Ar ⁸⁰ , R ⁷¹ , R ⁷² , A ¹ , and A ² , refer to Ar ¹ , Ar ³ , R ⁴¹ , R ⁴² , A ¹ , and A ² of general formula (1a). corresponding records.

Specific examples of the compound represented by the general formula (8a) are given below. The compounds of the general formula (8a) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 67]

As a preferable group of compounds having a skeleton (8b), compounds represented by the following general formula (8b) can be exemplified. General formula (8b) [Chemical formula 68]

In the 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, A substituted or unsubstituted aryl group is preferably selected. R ⁷³ and R ⁷⁴ each independently represent a substituted or unsubstituted alkyl group. m73 and m74 each independently represent the integer of 0-4. n81 and n82 each independently represent the integer of 0-4. Y ²⁷ and Y ²⁸ each 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 each independently represent a hydrogen atom, a deuterium atom or a substituent. For detailed descriptions of m73, m74, n81, and n82, descriptions of m71, m72, n79, and n80 of the general formula (8a) can be referred to. For preferred groups of Ar ⁸¹ , Ar ⁸² , R ⁷³ , R ⁷⁴ , A ¹ , and A ² , refer to Ar ¹ , Ar ³ , R ⁴¹ , R ⁴² , A ¹ , and A ² of general formula (1a). corresponding records.

Specific examples of the compound represented by the general formula (8b) are given below. The compounds of the general formula (8b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 69]

Preferable examples include compounds in which both of the two benzene rings constituting the carbazole partial structure present in the general formula (G) are condensed with the benzene rings. Examples of such compounds include compounds having the following skeleton (9a) and compounds having the following skeleton (9b). [chemical formula 70]

In skeletons (9a) and (9b), Y ²⁹ to Y ³² each independently represent two hydrogen atoms, a single bond or N(R ²⁷ ). For details of Y ²⁹ to Y ³² , reference can be made to the corresponding description of skeletons (4a) and (4b). In one aspect of the present invention, each hydrogen atom in the skeleton (9a) and (9b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (9a), compounds represented by the following general formula (9a) can be exemplified. general formula (9a) [chemical formula 71]

In the general formula (9a), R ⁷⁵ and R ⁷⁶ each independently represent a substituted or unsubstituted alkyl group. m75 and m76 each independently represent the integer of 0-4. Y ²⁹ and Y ³⁰ each 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 each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of R ⁷⁵ , R ⁷⁶ , m75, m76, A ¹ , and A ² , reference can be made to the description of R ⁷¹ , R ⁷² , m71, m72, A ¹ , and A ² in the general formula (8a).

Specific examples of the compound represented by the general formula (9a) are given below. The compounds of the general formula (9a) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 72]

As a preferable group of compounds having a skeleton (9b), compounds represented by the following general formula (9b) can be exemplified. General formula (9b) [Chemical formula 73]

In the general formula (9b), R ⁷⁷ and R ⁷⁸ each independently represent a substituted or unsubstituted alkyl group. m77 and m78 each independently represent the integer of 0-4. Y ³¹ and Y ³² each 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 each independently represent a hydrogen atom, a deuterium atom or a substituent. For details of R ⁷⁷ , R ⁷⁸ , m77, m78, A ¹ , and A ² , reference can be made to the description of R ⁷¹ , R ⁷² , m71, m72, A ¹ , and A ² in the general formula (8a).

Specific examples of the compound represented by the general formula (9b) are given below. The compounds of the general formula (9b) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 74]

As the compound represented by the general formula (G), a compound containing four or more carbazole moiety structures in the molecule is also preferable. As an example of such a compound, the compound which has the following skeleton (10) can be illustrated. Skeleton (10) [Chemical Formula 75]

Each hydrogen atom in the skeleton (10) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted together with adjacent hydrogen atoms as a linking group to form a ring structure. For details, the description of R ¹ to R ²⁶ , A ¹ , and A ² corresponding to the general formula (G) can be referred to. At least one hydrogen atom in the benzene ring constituting the partial structure of carbazole included in the skeleton (10) is substituted with a substituted or unsubstituted aryl group. In one aspect of the present invention, each hydrogen atom in the skeleton (10) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having the skeleton (10), compounds represented by the following general formula (10) can be exemplified. general formula (10) [chemical formula 76]

In the general formula (10), Ar ⁹¹ to Ar ⁹⁴ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. n91 and n93 each independently represent an integer of 0 to 4, and n92 and n94 each independently represent an integer of 0 to 3. α ring, β ring, γ ring, δ ring can be substituted, at least one ring is substituted by substituted or unsubstituted aryl, or condensed with substituted benzene ring, or substituted or unsubstituted benzene The furan ring of a furan or the thiophene ring of a substituted or unsubstituted thiophene is condensed. A ¹ and A ² each independently represent a hydrogen atom, a deuterium atom or a substituent. In one aspect of the present invention, n91˜n94 are integers of 0˜2. In one aspect of the present invention, n91 and n93 are the same number, and n92 and n94 are the same number. All of n91 to n94 may be the same number, for example, all may be 0 or all may be 1. For preferred groups of Ar ⁹¹ to Ar ⁹⁴ , reference can be made to the corresponding descriptions of Ar ¹ to Ar ⁴ in the general formula (1a). In one aspect of the present invention, the α ring and the γ ring have the same substituent or have the same condensed structure, and the β ring and the δ ring have the same substituent or have the same condensed structure. In one aspect of the invention, both the β and δ rings are substituted with substituted or unsubstituted aryl groups, or condensed with optionally substituted benzene rings, or substituted or unsubstituted benzofuran Furan ring or thiophene ring condensation of substituted or unsubstituted thiophene. In one aspect of the invention, both the alpha and gamma rings are substituted with substituted or unsubstituted aryl groups, or condensed with optionally substituted benzene rings, or substituted or unsubstituted benzofuran Furan ring or thiophene ring condensation of substituted or unsubstituted thiophene. In one aspect 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 substituted benzene rings, or substituted or unsubstituted The furan rings of substituted benzofurans or the thiophene rings of substituted or unsubstituted thiophenes are condensed. For descriptions and preferred ranges of ^A1 and ^A2 , reference can be made to the corresponding description of the general formula (G).

Specific examples of the compound represented by the general formula (10) are given below. The compounds of the general formula (10) that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 77]

The compound represented by the general formula (G) may have no symmetry in the skeleton. For example, it may be a compound having an asymmetric skeleton such as the following skeleton (11a) or the following skeleton (11b). [chemical formula 78]

In skeletons (11a) and (11b), Z ¹⁷ and Z ¹⁸ each independently represent an oxygen atom or a sulfur atom. In one aspect of the present invention, each hydrogen atom in the skeleton (11a) and (11b) may not be substituted with adjacent hydrogen atoms as a linking group to form a ring structure.

As a preferable group of compounds having a skeleton (11a), compounds represented by the following general formula (11a) can be exemplified. General formula (11a) [Chemical formula 79]

In the general formula (11a), Ar ⁸³ to Ar ⁸⁵ independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, for example, A substituted or unsubstituted aryl group is preferably selected. R ⁸³ and R ⁸⁴ each independently represent a substituted or unsubstituted alkyl group. Z ¹⁷ represents an oxygen atom or a sulfur atom. m83 and m84 each independently represent the integer of 0-5. n83 represents an integer of 0 to 4, and n84 and n85 represent an integer of 0 to 3 each independently. For details and preferred ranges of Ar ⁸³ to Ar ⁸⁵ , R ⁸³ , R ⁸⁴ , m83, m84, n83 to n85, refer to Ar ¹ , Ar ² , Ar ⁴ , R ⁴¹ , and R ⁴² in general formula (1a). , m1, m2, n1, n2, n4 records.

Specific examples of the compound represented by the general formula (11a) are given below. The compounds of the general formula (11a) that can be used in the present invention are not limitedly interpreted by the following specific examples. In the following specific examples, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are respectively disclosed. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 80]

As a preferable group of compounds having a skeleton (11b), compounds represented by the following general formula (11b) can be exemplified. General formula (11b) [Chemical formula 81]

In the general formula (11b), Ar ⁸⁶ to Ar ⁸⁸ independently represent substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkyl, for example, A substituted or unsubstituted aryl group is preferably selected. R ⁸⁶ and R ⁸⁷ each independently represent a substituted or unsubstituted alkyl group. Z ¹⁸ represents an oxygen atom or a sulfur atom. m86 and m87 each independently represent the integer of 0-5. n86 represents an integer of 0 to 4, and n87 and n88 represent an integer of 0 to 3 each independently. For details and preferred ranges of Ar ⁸⁶ to Ar ⁸⁸ , R ⁸⁶ , R ⁸⁷ , m86, m87, n86 to n88, refer to Ar ¹ , Ar ² , Ar ⁴ , R ⁴¹ , and R ⁴² in general formula (1a). , m1, m2, n1, n2, n4 records.

Specific examples of the compound represented by the general formula (11b) are given below. The compounds of the general formula (11b) that can be used in the present invention are not limitedly interpreted by the following specific examples. In the following specific examples, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are respectively disclosed. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 82]

As the compound represented by the general formula (G), a compound in which R ⁵ is a donor group can be preferably used. The compound in which R ⁵ is a donor group tends to have a high molar extinction coefficient and a high luminous efficiency. For example, compared with compounds in which R ³ is a donor group, it exhibits excellent luminescence characteristics. In a preferred aspect of the present invention, R ³ is not a donor group. In a preferred aspect of the present invention, among R ¹ to R ⁷ , only R ⁵ is a donor group or neither of them is a donor group (especially, a donor group whose σp value is -0.2 or less) . The donor group is a group with a negative Hammett's σp value. The σp value of the donor group of R ⁵ is preferably -0.2 or less, for example, -0.4 or less, for example, -0.6 or less. As a preferable donor group, a substituted amino group can be mentioned, preferably a substituted or unsubstituted diarylamine group. The aryl group may be a single ring or a condensed ring formed by condensing two or more rings. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, for example, can be selected from 2 to 4 or set to two. The two aryl groups constituting the diarylamino group may be the same or different. Also, two aryl groups may be connected by a single bond or a linking group. As the substituted or unsubstituted diarylamino group, a substituted or unsubstituted diphenylamino group is preferred. A substituted or unsubstituted carbazol-9-yl in which two phenyl groups are bonded by a single bond may be used, or a substituted or unsubstituted dicarbazol-9-yl group in which two phenyl groups are not bonded by a single bond may be used. Anilino. When any one of R ¹ to R ⁷ in the general formula (G) is a substituted amino group, at least R ⁵ is preferably a substituted amino group, and more preferably only R ⁵ is a substituted amino group. In one aspect of the invention, ^R3 is not a substituted amine. When R ⁵ is a donor group and X ¹ is a nitrogen atom, R ¹⁶ or R ¹⁹ is preferably a donor group, more preferably R ¹⁹ is a donor group. At this time, other R ¹ to R ²⁶ can be hydrogen atoms or deuterium atoms, for example, at least one of R ³ , R ⁶ , R ¹⁵ , and R ²⁰ can be a substituent (preferably substituted or unsubstituted alkyl or substituted or unsubstituted aryl) and others are hydrogen or deuterium atoms. When R ⁵ is a donor group and X ¹ is a boron atom, R ²⁰ or R ²³ is preferably a donor group, more preferably R ²⁰ is a donor group. At this time, other R ¹ to R ²⁶ can be hydrogen atoms or deuterium atoms, for example, at least one of R ³ , R ⁶ , R ¹⁹ , and R ²⁴ can be a substituent (preferably substituted or unsubstituted alkyl or substituted or unsubstituted aryl) and others are hydrogen or deuterium atoms. As a preferable group of compounds in which R ⁵ is a donor group, compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b) can be exemplified. General formula (12a) [Chemical formula 83]

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

Specific examples of the compounds represented by the general formula (12a) and the general formula (12b) are given below. However, the compounds of general formula (12a) and general formula (12b) that can be used in the present invention are not limitedly interpreted by the following specific examples. In the following specific examples, the structure of each compound is specified by identifying R, Ar and X in the formulas F1 to F56 in the table. R is selected from A to D described below, Ar is selected from a to d described below, and X is selected from α to γ. For example, the compound No. 1 in the table is a compound having a structure in which R is A and Ar is a in formula F1.

[化學式85]

[化學式86]

[化學式87]

[化學式88]

[化學式89]

[表1]

[chemical formula 84]

[chemical formula 85]

[chemical formula 86]

[chemical formula 87]

[chemical formula 88]

[chemical formula 89]

[Table 1]

[chemical formula 90]

In one aspect of the present invention, the aforementioned skeletons (1a) to (12b) are skeletons that are not further condensed with other rings. In one aspect of the present invention, the aforementioned skeletons (1a) to (12b) are skeletons that can be further condensed with other rings. Regarding the other rings described here, reference can be made to the aforementioned R ¹ and R ² , R ² and R ³ , R ³ and R 4 , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , ^{R 8} and R ⁹ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R 12 , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 18 and} R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ²² and R 23 , R ²³ and R ²⁴ , R ²⁴ and ^{R 25 , and R 25 and R 26} are bonded to form ring structures.

In one aspect of the present invention, A ¹ and A ² of the general formula (G) are acceptor groups. For example, a compound having an acceptor group at the positions of ^A1 and ^A2 and having any one of skeletons (1a) to (12b) can be mentioned. For the description and specific examples of the acceptor group, the description and specific examples of the acceptor groups of ^A1 and ^A2 of the general formula (G) above can be referred to. Specific examples of compounds in which ^A1 and ^A2 are acceptor groups are given below. The compounds in which A ¹ and A ² are acceptor groups that can be used in the present invention are not limitedly interpreted by the following specific examples. In the following specific examples, both ^A1 and ^A2 have the structure "A", and the structure of each compound is confirmed by determining the "A" alone. [chemical formula 91]

In one aspect of the present invention, a compound having a rotationally symmetrical structure is selected as the compound represented by the general formula (G). In one aspect of the present invention, a compound having a line-symmetric structure is selected as the compound represented by the general formula (G). In one aspect of the present invention, a compound having an asymmetric structure is selected as the compound represented by the general formula (G). Specific examples of compounds having an asymmetric skeleton are given below. A compound having an asymmetric skeleton or a compound having an asymmetric structure that can be used in the present invention is not limitedly interpreted by the following specific examples. Regarding specific examples containing X, a compound in which all X in the molecule are oxygen atoms and a compound in which all X in the molecule are sulfur atoms are disclosed, respectively. A compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used. [chemical formula 92]

Specific examples of compounds having a symmetrical skeleton but having an asymmetric structure due to asymmetric bonding of substituents are given below. Compounds having an asymmetric structure that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 93]

In one aspect of the present invention, R ³ of the general formula (G) is not a diarylamine group (two aryl groups constituting the diarylamine group may be bonded to each other). In a preferred aspect of the present invention, R ³ in the general formula (G) is a hydrogen atom, a deuterium atom or an acceptor group (not a donor group). In one aspect of the present invention, at least one of n1 to n4 in the general formula (1a) is 1 or more. In a preferred aspect of the present invention, at least one of m1 and m2 in the general formula (1a) is 1 or more. In a further preferred aspect of the present invention, at least one of n1 to n4 in the general formula (1a) is 1 or more, and at least one of m1 and m2 in the general formula (1a) is 1 or more. In one aspect of the present invention, at least one of n5 to n8 of the general formula (1b) is 1 or more. In a preferred aspect of the present invention, at least one of m3 and m4 in the general formula (1b) is 1 or more. In a further preferred aspect of the present invention, at least one of n5 to n8 in the general formula (1b) is 1 or more, and at least one of m3 and m4 in the 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, at least one of R ⁴¹ and R ⁴² and at least one of R ⁴³ and R ⁴⁴ may be substituted by a deuterium atom The alkyl group is preferably, for example, R ⁴¹ to R ⁴⁴ are all alkyl groups that may be substituted with deuterium atoms. When at least one of n1 to n4 is 1 or more, and at least one of n5 to n8 is 1 or more, at least one of Ar ¹ to Ar ⁴ and at least one of Ar ⁵ to Ar ⁸ can be deuterium atom or An aryl group substituted with an alkyl group is preferred, for example, Ar ¹ to Ar ⁸ are all aryl groups that may be substituted by a deuterium atom or an alkyl group. In one aspect of the present invention, when X ¹ in the general formula (G) is a boron atom and R ⁸ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ , and R ¹⁷ are alkyl (or methyl), R At least one of ¹ to R ⁷ , R ¹⁸ to R ²⁰ , and R ²³ to R ²⁶ is a substituent, preferably a group of substituent group E, such as an aryl group that may be substituted with a deuterium atom or an alkyl group. In one aspect of the present invention, when X ² in the general formula (G) is a boron atom and R ⁸ , R ¹⁰ , R ¹² , R ²² , R ²⁴ , and R ²⁶ are alkyl (or methyl), R At least one of ¹ to R ⁷ , R ¹³ to R ¹⁶ , and R ¹⁹ to R ²¹ is a substituent, preferably a group of substituent group E, such as an aryl group that may be substituted with a deuterium atom or an alkyl group. In one aspect of the present invention, X ¹ in the general formula (G) is a boron atom and any combination of R ⁸ and R ⁹ , R ⁹ and R ¹⁰ and R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ When any of the groups are bonded to each other to form an aromatic ring (or benzene ring), at least one of R ¹ to R ⁷ , R ¹⁸ to R ²⁰ , and R ²³ to R ²⁶ is a substituent, preferably a group of substituents The group of E is, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. In one aspect of the present invention, X ² in the general formula (G) is a boron atom and any combination of R ⁸ and R ⁹ , R ⁹ and R ¹⁰ and R ²² and R ²³ , R ²³ and R ²⁴ When any of the groups are bonded to each other to form an aromatic ring (or benzene ring), at least one of R ¹ to R ⁷ , R ¹³ to R ¹⁶ , and R ¹⁹ to R ²¹ is a substituent, preferably a group of substituents The group of E is, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. In one aspect of the present invention, R ⁹ and R ¹¹ of the general formula (G) are neither cyano nor alkyl. That is, R ⁹ and R ¹¹ are a hydrogen atom, a deuterium atom, or a substituent other than a cyano group and an alkyl group. In one aspect of the present invention, R ⁹ and R ¹¹ of the general formula (G) are neither cyano nor tertiary butyl. In a preferred aspect of the present invention, at least one of R ⁸ to R ¹² in the general formula (G) is a substituent. In one aspect of the present invention, R ³ of the general formula (G) is not a substituted amino group or an aryl group. In one aspect of the present invention, R ³ of the general formula (G) is not a substituted amino group or a phenyl group. In one aspect of the present invention, R ³ in the general formula (G) is not dimethylamino, diphenylamino, or phenyl. In a preferred aspect of the present invention, at least one of R ¹ to R ²⁶ in the general formula (G) is a substituent, more preferably at least one of R ¹ to R ²⁶ is an alkyl group, such as carbon Alkyl groups with numbers 1 to 4.

In addition, in one aspect of the present invention, the compound represented by the general formula (1) can be used together with other host materials as a light-emitting layer (composition) including a plurality of host materials. That is, in one aspect of the present invention, the composition of the present invention contains a plurality of host materials including the compound represented by the general formula (1). In the composition of the present invention, a plurality of compounds represented by the general formula (1) may be used, or a compound represented by the general formula (1) and a host material not represented by the general formula (1) may be used in combination. In the following, preferred compounds that can be used as the second host material used together with the compound represented by the general formula (1) are listed, but the second host material that can be used in the present invention is not limited by these specific examples explanatory.

[chemical formula 94]

The form of the composition of the present invention is not particularly limited. In a particularly preferred aspect of the present invention, the composition of the present invention is in the form of a film. A film composed of the composition of the present invention can be formed by a wet process or a dry process. In the wet process, a solution obtained by dissolving the composition of the present invention is applied on a surface, and a light-emitting layer is formed after removing the solvent. Examples of the wet process include spin coating, slit coating, inkjet (spray coating), gravure printing, offset printing, and flexographic printing, but are not limited thereto. In the wet step, an appropriate organic solvent is selected and used, which is capable of dissolving the composition of the present invention. In a certain embodiment, a substituent (for example, an alkyl group) that improves solubility in an organic solvent can be introduced into the compound contained in the composition of the present invention. As a dry step, a vacuum evaporation method can be preferably employed. In the case of using the vacuum deposition method, each compound constituting the composition of the present invention may be co-deposited from a separate deposition source, or may be co-deposited from a single deposition source in which all compounds are mixed. In the case of using a single vapor deposition source, mixed powder mixed with compound powder may be used, a compression molded product in which the mixed powder is compressed may be used, or a compound obtained by heating, melting and mixing each compound and then cooling may be used. mixture. In a certain embodiment, by performing co-evaporation under the condition that the vapor deposition rates (weight loss rates) of the plurality of compounds contained in a single vapor deposition source are the same or almost the same, it is possible to form a A film in which the composition ratio of the plurality of compounds included corresponds to the composition ratio. A film having a desired composition ratio can be easily formed by mixing a plurality of compounds in the same composition ratio as that of the film to be formed as a vapor deposition source. In a certain embodiment, it is possible to determine the temperature at which the respective compounds to be co-deposited have the same weight loss rate, and use this temperature as the temperature at the time of co-deposition. When forming a film by vapor deposition, the molecular weight of each compound constituting the composition is preferably 1500 or less, more preferably 1200 or less, still more preferably 1000 or less, and still more preferably 900 or less. The lower limit of the molecular weight may be 450, 500 or 600, for example.

(Organic Light Emitting Device) By forming a light-emitting layer composed of the composition of the present invention, excellent organic light-emitting elements such as organic photoluminescence elements (organic PL elements) and organic electroluminescence elements (organic EL elements) can be provided. The organic light-emitting device of the present invention is a fluorescent light-emitting device, and the largest component of the luminescence from the device is fluorescence (fluorescence referred to herein includes delayed fluorescence). The thickness of the light-emitting layer can be, for example, 1 to 15 nm, 2 to 10 nm, or 3 to 7 nm. An organic photoluminescent device has a structure in which at least a light emitting layer is formed on a substrate. In addition, the organic electroluminescent device has at least an anode, a cathode, and a structure in which an organic layer is formed between the anode and the cathode. The organic layer includes at least a light-emitting layer, and may be formed of only the light-emitting layer, or may have one or more organic layers in addition to the light-emitting layer. Examples of such another organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an exciton barrier layer. The hole transport layer can be a hole injection transport layer with a hole injection function, and the electron transport layer can be an electron injection transport layer with an electron injection function. A specific structural example of an organic electroluminescence element is shown in FIG. 1 . In FIG. 1, 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transport layer, 5 denotes a light-emitting layer, 6 denotes an electron transport layer, and 7 denotes a cathode. When the organic light-emitting device of the present invention is a multi-wavelength light-emitting type organic light-emitting device, light emission with the shortest wavelength can include delayed fluorescence. In addition, it is also possible to assume that the light emission with the shortest wavelength does not include delayed fluorescence. When the organic light-emitting element using the composition of the present invention is excited by thermal or electronic mechanisms, it can be used in the ultraviolet region, blue, green, yellow, orange, and red regions of the visible spectrum (such as 420-500nm, 500-600nm or 600-700nm) or emit light in the near-infrared region. For example, an organic light emitting element can emit light in a red or orange region (for example, 620˜780 nm). For example, an organic light emitting element can emit light in an orange or yellow region (for example, 570-620 nm). For example, an organic light emitting element can emit light in a green region (for example, 490 to 575 nm). For example, an organic light emitting element can emit light in a blue region (for example, 400 to 490 nm). For example, an organic light-emitting element can emit light in an ultraviolet spectral region (eg, 280-400 nm). For example, an organic light-emitting element can emit light in an infrared spectral region (for example, 780 nm to 2 μm). It is preferable that the largest component of the light emission from the organic light-emitting device using the composition of the present invention is the light emission from the delayed fluorescent material contained in the composition of the present invention. The luminescence from the compound represented by general formula (1) is preferably less than 10% of the luminescence from the organic light-emitting element, for example, it can be less than 1%, less than 0.1%, less than 0.01% and below the detection limit. The light emission from the delayed fluorescent material may be, for example, more than 50%, more than 90%, or more than 99% of the light emission from the organic light emitting element. When the layer (light-emitting layer) containing the composition of the present invention contains a fluorescent material as the third component, the largest component of light emission from the organic light-emitting element may be light emission from the fluorescent material. In this case, the light emission from the light emitting material may be, for example, more than 50%, more than 90%, or more than 99% of the light emission from the organic light emitting element.

In the following, each layer other than each member and the light-emitting layer of the organic electroluminescence element will be described.

Substrate: In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, and the substrate is not particularly limited, as long as it is generally used in organic electroluminescent elements, such as glass, transparent plastic, quartz and Any material formed from silicon will suffice.

Anode: In some embodiments, the anode of the organic electroluminescent device is made of 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 more). In some embodiments, the aforementioned metal is Au. In some embodiments, the conductive transparent material can be selected from CuI, indium tin oxide (ITO), SnO ₂ and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film such as IDIXO (In ₂ O ₃ —ZnO) is used. In some embodiments, the aforementioned anode is a thin film. In some embodiments, the aforementioned thin film is fabricated by evaporation or sputtering. In some embodiments, the aforementioned film is patterned by photolithography. In some embodiments, if the pattern does not require high precision (for example, above about 100 μm), the pattern can be formed by evaporating or sputtering the electrode material using a mask with a better shape. In some embodiments, when a coating material such as an organic conductive compound can be coated, a wet film forming method such as a printing method or a coating method can be used. In some embodiments, the anode has a transmittance greater than 10% when radiated light passes through the anode, and the anode has a sheet resistance per unit area of several hundred ohms or less. In some embodiments, the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

Cathode: In some embodiments, the cathode is made of electrode materials such as metals (below 4eV) with low work function (called electron injection metals), alloys, conductive compounds or combinations thereof. In some embodiments, the aforementioned electrode material can be selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-alumina (Al ₂ O ₃ ) Mixture, indium, lithium-aluminum mixture and rare earth elements for selection. In some embodiments, a mixture of an electron-injecting metal and a stable metal having a higher work function than the electron-injecting metal, that is, a second metal, may be used. In some embodiments, the aforementioned mixture can be selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-alumina (Al ₂ O ₃ ) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the aforementioned mixture improves electron injection properties and resistance to oxidation. In some embodiments, the cathode is fabricated by forming the electrode material into a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the cathode has a thickness of 10 nm˜5 μm. In some embodiments, the aforementioned cathode has a thickness of 50-200 nm. In some embodiments, any one of the anode and the cathode of the organic electroluminescence element is transparent or translucent to transmit radiated light. In some embodiments, a transparent or translucent electroluminescent element enhances the brightness of light radiation. In some embodiments, the transparent or translucent cathode is formed by forming the cathode from the conductive, transparent material described for the anode. In some embodiments, the element contains an anode and a cathode, but both are transparent or translucent.

Inject layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the aforementioned injection layer reduces the driving voltage and enhances the brightness of light radiation. 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 the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, no injection layer is present. Examples of preferable compounds that can be used as hole injection materials are given below.

[chemical formula 95]

Next, examples of preferable compounds that can be used as electron injection materials are given. [chemical formula 96]

Barrier layer: The barrier layer is a layer capable of preventing charges (electrons or holes) and/or excitons existing in the light emitting layer from diffusing to the outside of the light emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole-transport layer to prevent electrons from passing through the light-emitting layer to the hole-transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron-transport layer to prevent holes from passing through the light-emitting layer to the electron-transport layer. In some embodiments, the barrier layer prevents excitons from diffusing to the outside of the light emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. The term "electron barrier layer" or "exciton barrier layer" used in this specification includes the layer which has both the function of an electron barrier layer and the function of an exciton barrier layer.

Hole barrier layer: The hole barrier layer functions as an electron transport layer. In some embodiments, the hole barrier layer prevents holes from reaching the electron transport layer during transport of electrons. In some embodiments, the hole barrier layer increases the probability of rebonding of electrons and holes in the light-emitting layer. Materials used in the hole barrier layer may be the same materials as described for the electron transport layer. Examples of preferable compounds that can be used in the hole barrier layer are given below.

[chemical formula 97]

Electron barrier layer: The electron barrier layer transports holes. In some embodiments, the electron barrier layer prevents electrons from reaching the hole transport layer during transport of holes. In some embodiments, the electron barrier layer increases the probability of rebonding of electrons and holes in the light-emitting layer. Materials used in the electron barrier layer may be the same materials as described for the hole transport layer. Specific examples of preferable compounds that can be used as electron barrier materials are given below.

[chemical formula 98]

Exciton barrier layer: The exciton barrier layer prevents excitons generated by rebonding of holes and electrons in the light emitting layer from diffusing to the electron transport layer. In some embodiments, the exciton barrier layer can effectively confine excitons in the light emitting layer. In some embodiments, the light radiation efficiency of the device is increased. In some embodiments, the exciton barrier layer is adjacent to the light emitting layer on either of the anode side and the cathode side and adjacent to the light emitting layers on both sides thereof. In some embodiments, when the exciton barrier layer is present on the anode side, the layer may be present between the hole transport layer and the light emitting layer adjacent to the light emitting layer. In some embodiments, when the exciton barrier layer is present on the cathode side, the layer may be present between the light emitting layer and the cathode and adjacent to the light emitting layer. In some embodiments, a hole injection layer, an electron barrier layer, or the same layer is present between the anode and the exciton barrier layer adjacent to the light emitting layer on the anode side. In some embodiments, a hole injection layer, an electron barrier layer, a hole barrier layer, or the same layer is present between the cathode and the exciton barrier layer adjacent to the light emitting layer on the cathode side. In some embodiments, the exciton barrier layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy, respectively, of the light-emitting material.

Hole transport layer: The hole transport layer contains a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has a plurality of layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron barrier properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention are not limited, but include triazole derivatives, oxadiazole inducers, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives substances, polyaryl alkanes inducers, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl Anthracene inducers, stilone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer 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 styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferable compounds that can be used as a hole transport material are given below.

[chemical formula 99]

Electron transport layer: The electron transport layer contains an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has a plurality of layers. In some embodiments, the electron transport material only needs to have a 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 the electron transport layer that can be used in the present invention are not limited, but include nitro-substituted stilbene derivatives, dibenzoquinone derivatives, thiopyran derivatives, carbodiimides, and tertiaryl methane (fluorenylidene methane) derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, oxazole derivatives, 𠯤 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 polymeric material. Specific examples of preferable compounds that can be used as electron transport materials are given below.

[chemical formula 100]

Furthermore, examples of preferable compounds as materials that can be added to each organic layer are given. For example, it is conceivable to add it as a stabilizing material.

[chemical formula 101]

Preferable materials that can be used in organic electroluminescent elements are specifically exemplified, but materials that can be used in the present invention are not limitedly interpreted by the following exemplary compounds. Moreover, even if it is a compound illustrated as the material which has a specific function, it can also be converted into the material which has other functions.

device: In some embodiments, a light emitting layer is incorporated into a device. For example, devices include OLED valves, OLED lamps, monitors for televisions, monitors for computers, mobile phones, and tablets, but are not limited thereto. In some embodiments, an electronic device includes an OLED having at least one organic layer including 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 photoactive 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 a hole transport material. Examples of the aforementioned devices include organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), and organic light-emitting transistors. (O-LET), organic solar cell (O-SC), organic optical detection device, organic photoreceptor, organic field-quencher (O-FQD), light-emitting electrochemical cell (LEC) or organic mine Diode (O-laser).

Valve or Lamp: In some embodiments, an electronic device includes an OLED having at least one organic layer including 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, a device includes an array comprising a combination of OLEDs. In some embodiments, the aforementioned combination of OLEDs is a combination of three colors (eg, RGB). In some embodiments, the aforementioned combination of OLEDs is a combination of colors that are neither red nor green nor blue (eg, orange and yellow-green). In some embodiments, the aforementioned combination of OLEDs is a combination of two colors, four colors or more. In some embodiments, the device is an OLED lamp having: A circuit board having a first surface having a mounting surface and a second surface opposite to the first surface, and defining at least one opening; At least one OLED, which is at least one OLED on the aforementioned installation surface, the at least one OLED includes at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode, and has a light-emitting structure; Housings for circuit boards; and At least one connector is arranged at the end of the aforementioned casing, and the aforementioned casing and the aforementioned connector are divided into packages suitable for being installed on lighting equipment. In some embodiments, the aforementioned OLED lamp has a plurality of OLEDs, and the plurality of OLEDs are mounted on a circuit board to radiate light in a plurality of directions. In some embodiments, a portion of the light emitted in the first direction is polarized to radiate in the second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

Monitor or screen: In some embodiments, the emissive layers of the present invention can be used in screens or displays. In some embodiments, the compound of the present invention is not limited, but is deposited on the 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 in double-sided etching to provide pixels with unique aspect ratios. The aforementioned screen (and, also called mask) can be used in the manufacturing steps of OLED displays. By designing corresponding artwork patterns, it is possible to arrange very steep narrow connecting rods between pixels in the vertical direction and arrange large-scale inclined openings in the horizontal direction. Thereby, while optimizing the chemical vapor deposition on the TFT backplane, it is possible to form a fine pattern of pixels required for a high-resolution display. By patterning the inside of the pixel, it is possible to form three-dimensional pixel openings with various aspect ratios in the horizontal direction and the vertical direction. Furthermore, the use of imaged "stripes" or halftone circles in the pixel area protects etching in specific areas until those specific patterns are undercut and removed from the substrate. At this time, all pixel regions are processed at the same etching rate, but their depths vary according to the halftone pattern. By changing the size and interval of the halftone pattern, it is possible to perform etching with various protection ratios in the pixel, and to perform partial deep etching required for forming steep vertical inclinations. The preferred material for the evaporation mask is Invar. Because steel is a thin sheet metal alloy grown by cold rolling in steel mills. Insteel cannot be electrodeposited onto the rotating mandrel as a nickel mask. A suitable and low-cost method for forming an open area in a mask for evaporation is a method based on wet chemical etching. In some embodiments, the screen or display pattern is a matrix of pixels on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (eg, 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.

Manufacturing method of the device: With regard to OLED displays, a large-scale motherboard is usually formed, and then the motherboard is diced in unit panel units to manufacture. Generally, each unit panel on a motherboard is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and coating a planarization film on the aforementioned TFT to sequentially A pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer are formed over time, and cut from the aforementioned motherboard. With regard to OLED displays, a large-scale motherboard is usually formed, and then the motherboard is diced in unit panel units to manufacture. Generally, each unit panel on a motherboard is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and coating a planarization film on the aforementioned TFT to sequentially A pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer are formed over time, and cut from the aforementioned motherboard.

In other aspects of the present invention, a method of manufacturing an organic light emitting diode (OLED) display is provided, the method comprising: A step of forming a barrier layer on the base substrate of the motherboard; A step of forming a plurality of display units in units of unit panels on the aforementioned barrier layer; A step of forming an encapsulation layer on each of the display units of the aforementioned unit panel; and A 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 end of the barrier layer is covered by an organic thin film formed of polyimide or acrylic. In some embodiments, the organic film-assisted master 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 thin-film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film. The planarization film is formed of the same material and formed simultaneously with the formation of the aforementioned planarization film. In some embodiments, the aforementioned light-emitting unit is connected to the TFT layer through a passivation layer, a 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 with the display unit, nor is it connected with the encapsulation layer.

Each of the aforementioned organic thin film and planarization film may contain any one of polyimide and acrylic. In some embodiments, the aforementioned barrier layer may be an inorganic thin film. In some embodiments, the aforementioned base substrate may be formed of polyimide. The aforementioned method may also include the step of mounting a carrier substrate formed of a glass material on the other surface of the base substrate formed of polyimide before forming the barrier layer on one surface of the base substrate formed of polyimide and A step of separating the aforementioned carrier substrate from the base substrate before cutting the interface portion. 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, the planarization film is formed of polyimide or acrylic, similarly to the organic thin film formed at the end of the barrier layer. In some embodiments, the planarization film and the organic thin film are formed at the same time when the OLED display is manufactured. In some embodiments, the aforementioned organic thin film may be formed at the end of the barrier layer, whereby a part of the organic thin film is in direct contact with the base substrate, while the remaining part of the organic thin film surrounds the end of the barrier layer, contact with the barrier layer.

In some embodiments, the aforementioned light emitting layer has a pixel electrode, a counter electrode, and an organic light emitting layer arranged between the pixel electrode and the counter electrode. In some embodiments, the aforementioned pixel electrodes are connected to the source/drain electrodes of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, whereby the organic light emitting layer radiates light to form an image. Hereinafter, an image forming unit having a TFT layer and a light emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display unit and prevents the penetration of external moisture can be formed as a thin-film encapsulation structure in which organic thin films and inorganic thin films are alternately laminated. In some embodiments, the aforementioned encapsulation layer has a film-like encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic thin film coated on the interface portion is arranged at a distance from each of the plurality of display units. In some embodiments, the organic thin film is formed in such a manner that a part of the organic thin film is in direct contact with the base substrate, and the rest of the organic thin film is in contact with the barrier layer while surrounding the end of the barrier layer.

In one aspect, the OLED display is flexible and uses a flexible base substrate formed of polyimide. In some embodiments, the aforementioned base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated. In some embodiments, the barrier layer is formed on the surface of the base substrate opposite to the carrier substrate. In one embodiment, the aforementioned barrier layer is patterned according to the size of each unit panel. For example, while the base substrate is formed on all surfaces of the mother board, the barrier layer is formed according to the size of each unit panel, whereby grooves are formed on the interface portion between the barrier layers of the unit panels. Each unit panel can be cut along the aforementioned groove.

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, at least a part of the organic thin film is formed in the groove, and the groove does not penetrate into the base substrate middle. In some embodiments, the TFT layer of each unit panel is formed, and a passivation layer as an inorganic thin film and a planarization film as an organic thin film are disposed on the TFT layer to cover the TFT layer. For example, at the same time as the planarization film made of polyimide or acrylic is formed, the grooves in the interface portion are covered with, for example, an organic thin film made of polyimide or acrylic. This prevents cracks from being generated by absorbing the impact generated to the organic thin film when each unit panel is cut along the groove on the interface portion. That is, in the case where all the barrier layers are fully exposed due to no organic thin film, when each unit panel is cut along the groove on the interface portion, the impact generated is transmitted to the barrier layer, whereby the risk of cracking increases . However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb the impact that can be transmitted to the barrier layer without the organic film, so that each unit panel can be soft-cut to prevent damage to the barrier layer cracks in the layer. In one embodiment, the organic thin film and the planarizing film covering the groove in the interface portion are arranged at intervals from each other. For example, in the case where the organic thin film and the planarizing film are connected to each other as a single layer, external moisture may infiltrate into the display unit through the remaining part of the planarizing film and the organic thin film, so the organic thin film and the planarizing film are separated from each other. They are arranged at intervals so that the organic thin film and the display unit are arranged at intervals.

In some embodiments, the display unit is formed by forming a light emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thereby, after the master is completely manufactured, the carrier base material carrying the base base material is separated from the base base material. In some embodiments, when the carrier substrate is irradiated with a laser beam, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the motherboard is cut in unit panel units. In some embodiments, the mother board is cut along the interface between the unit panels using a cutter. In some embodiments, the grooves of the motherboard along the dicing interface are covered with an organic film so that the organic film absorbs shock during dicing. In some embodiments, cracks can be prevented from being generated in the barrier layer during dicing. In some embodiments, the aforementioned method reduces the defective rate of the product and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic thin film coated on the end of the barrier layer . [Example]

Hereinafter, the characteristics of the present invention will be described in more detail with reference to synthesis examples and examples. Materials, processing contents, processing procedures, and the like shown below can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention should not be limitedly interpreted by the specific examples shown below. In addition, regarding the evaluation of the emission characteristics, a source meter (manufactured by TEKTRONIX, INC.: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies Japan, Ltd.: E5273A), and an optical power meter measuring device (manufactured by Newport Corporation: E5273A) were used. 1930C), an optical spectrometer (Ocean Photonics.: USB2000), a spectroradiometer (TOPCON CORPORATION: SR-3), and a streak camera (C4334, Hamamatsu Photonics K.K.). Compounds contained in the general formula (1) were synthesized in the following synthesis examples.

(Synthesis Example 1) Synthesis of Compound 3a [Chemical Formula 102]

2-Bromo-8-phenyldibenzofuran (4.83g, 15.1mmol), 3-(9H-carbazol-9-yl)phenylboronic acid (5.21g, 18.2mmol), tetrakistriphenylphosphine palladium (0) (1.74g, 1.51mmol), potassium carbonate (6.27g, 45.4mmol) were dissolved in a mixed solution of tetrahydrofuran and water (100/50ml), and stirred at 75°C for 12 hours. The reaction solution was cooled to room temperature, chloroform was added, and the organic layer was washed twice with water, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane: chloroform = 8:2), thereby obtaining compound 3a as a white solid. (2.53g, 34%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.25 (s, 1H), 8.19-8.16 (m, 3H), 7.91 (s, 1H), 7.83-7.63 (m, 8H), 7.58 (d, J = 8Hz, 1H), 7.54-7.41 (m, 6H), 7.39-7.29 (m, 3H). MS (ASAP): 486.25 (M+H ⁺ ). Calcd. for C ₃₆ H ₂₃ NO: 485.18.

(Synthesis Example 2) Synthesis of Compound 3l [Chemical Formula 103]

Under nitrogen atmosphere, 4-biphenylboronic acid (2.53g, 12.8mmol), 2,8-dibromodibenzofuran (5.00g, 15.3mmol), tetrakistriphenylphosphine palladium (0) (0.74g, 0.640mmol), potassium carbonate (3.53g, 25.6mmol) were dissolved in a mixed solution of tetrahydrofuran and water (120/60ml), and stirred at 90°C for 16 hours. The reaction solution was cooled to room temperature, chloroform was added, and the organic layer was washed twice with water, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane: chloroform = 7:3) to obtain 2-[1,1′-biphenyl]-4-yl- 8-Bromodibenzofuran. (3.91g, 77%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.16-8.13 (m, 2H), 7.79-7.71 (m, 5H), 7.69-7.62 (m, 3H), 7.58 (dd, J = 8.8Hz, 2.0Hz , 1H), 7.50-7.46 (m, 3H), 7.38 (t, J =7.2Hz, 1H). MS (ASAP): 398.97 (M+H ⁺ ). Calcd for C ₂₄ H ₁₅ BrO: 398.03.

[chemical formula 104]

Under nitrogen atmosphere, 2-[1,1′-biphenyl]-4-yl-8-bromodibenzofuran (2.00g, 5.01mmol), 3-(9H-carbazol-9-yl)benzene Boronic acid (1.73g, 6.01mmol), tetrakistriphenylphosphine palladium (0) (0.58g, 0.501mmol), potassium carbonate (2.08g, 15.0mmol) were dissolved in a mixed solution of tetrahydrofuran and water (60/30ml) , and stirred at 75°C for 21 hours. The reaction solution was cooled to room temperature, chloroform was added, and the organic layer was washed twice with water, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane: chloroform = 7:3). Further recrystallization (toluene/acetonitrile) was carried out to obtain Compound 31 as a white solid. (2.05g, 73%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.27 (d, J = 1.6Hz, 1H), 8.23 (d, J = 2.0Hz, 1H), 8.18 (d, J = 7.6Hz, 2H), 7.92 ( t, J = 2.0Hz, 1H), 7.83-7.75 (m, 5H), 7.73-7.65 (m, 7H), 7.59 (m, 1H), 7.53-7.42 (m, 6H), 7.37 (t, J = 7.6Hz, 1H), 7.31 (t, J =8.0Hz, 2H). MS (ASAP): 562.11 (M+H ⁺ ). Calcd for C ₄₂ H ₂₇ NO: 561.21.

(Synthesis Example 3) Synthesis of Compound 3m [Chemical Formula 105]

Under nitrogen atmosphere, 2-[1,1′-biphenyl]-3-yl-8-bromodibenzofuran (2.67g, 6.69mmol), 3-(9H-carbazol-9-yl)benzene Boronic acid (2.31g, 8.03mmol), tetrakistriphenylphosphine palladium (0) (0.77g, 0.669mmol), potassium carbonate (2.77g, 20.1mmol) were dissolved in a mixed solution of tetrahydrofuran and water (50/25ml) , and stirred at 75°C for 18 hours. The reaction solution was cooled to room temperature, chloroform was added, and the organic layer was washed twice with water, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane: chloroform = 7:3), thereby obtaining compound 3m as a white solid. (2.34g, 63%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.27 (d, J = 1.2Hz, 1H), 8.24 (d, J = 1.6Hz, 1H), 8.18 (d, J = 8.0Hz, 2H), 7.83- 7.64 (m, 9H), 7.62-7.41 (m, 9H), 7.38 (t, J =7.2Hz, 1H), 7.31 (t, J =7.2Hz, 2H). MS (ASAP): 562.24 (M+H ⁺ ). Calcd for C ₄₂ H ₂₇ NO:561.21.

(Synthesis Example 4) Synthesis of Compound 3p [Chemical Formula 106]

2-Bromo-2,2'-dibenzofuran (1.5g, 3.63mmol), 3-(9H-carbazol-9-yl)phenylboronic acid (1.15g, 3.99mmol), tetrakistriphenylphosphine Palladium(0) (0.209g, 0.182mmol) and potassium carbonate (1.51g, 10.9mmol) were dissolved in a mixed solution of tetrahydrofuran and water (50/25ml), and stirred at 75°C for 12 hours. The reaction solution was cooled to room temperature, chloroform was added, and the organic layer was washed twice with water, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane: chloroform = 8:2). The obtained solid was recrystallized (toluene/methanol) to obtain Compound 3p as a white solid. (1.23g, 59%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.29 (s, 1H), 8.26 (s, 1H), 8.21 (s, 1H), 8.18 (d, J = 8Hz, 2H), 8.01 (d, J = 8Hz, 1H), 7.92 (s, 1H), 7.84-7.58 (m, 10H), 7.54-7.42 (m, 5H), 7.38-7.29 (m, 3H). MS (ASAP): 575.13 (M+H ⁺ ）. Calcd. for C ₄₂ H ₂₅ NO ₂ :575.19.

(Synthesis Example 5) Synthesis of Compound 7m [Chemical Formula 107]

Under nitrogen atmosphere, 2-[1,1′-biphenyl]-3-yl-8-(3-bromophenyl)dibenzofuran (2.3g, 4.84mmol), carbazole-1,2, 3,4,5,6,7,8-d8 (0.85g, 4.84mmol), tris(dibenzylideneacetone)dipalladium(0) (0.44g, 0.484mmol), tri-tertiary butylphosphine tetra Fluoborate (0.28g, 0.968mmol) and sodium tert-butoxide (0.93g, 9.68mmol) were added to 30ml of toluene and refluxed for 24 hours. The reaction solution was cooled to room temperature, and chloroform was added. The obtained organic layer was washed with water twice, and dried over magnesium sulfate to remove the solvent. The obtained solid was purified by silica gel column chromatography (developing solvent: dichloromethane/n-hexane=1:1). Further, recrystallization (toluene/methanol) was performed to obtain Compound 7m (1.47 g, 53%) as a white solid. ¹ H NMR (400MHz, CDCl ₃ , δ): 8.27 (s, 1H), 8.24 (s, 1H), 7.92 (s, 1H), 7.89 (s, 1H), 7.83-7.65 (m, 9H), 7.63 -7.55 (m, 3H), 7.47 (t, J =8Hz, 2H), 7.39 (t, J =8Hz, 1H). MS (ASAP): 570.34 (M+H ⁺ ). Calcd for C ₄₂ H ₁₉ D ₈ NO:569.26.

(Example 1) The following thin films were laminated at a vacuum degree of 5.0×10 ^-5 Pa on a glass substrate on which an anode composed of indium tin oxide (ITO) with a film thickness of 100 nm was formed by the vacuum evaporation method to produce organic electroluminescent elements. Firstly, HATCN with a thickness of 10nm is formed on ITO, NPD with a thickness of 30nm is formed thereon, and EBL1 with a thickness of 10nm is formed thereon. Next, the delayed fluorescent material (TADF21) and the compound 3a were co-deposited from different deposition sources to form a layer with a thickness of 40 nm, which was used as a light emitting layer. At this time, the content of the delayed fluorescent material was set to 35% by mass, and the content of the compound 3a was set to 65% by mass. Next, after forming SF3-TRZ to a thickness of 10 nm, Liq and SF3-TRZ were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. The contents of Liq and SF3-TRZ in this layer were set to 30% by mass and 70% by mass, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescent element. This element is referred to as an EL element 1 . Also, an EL element 2 was fabricated using compound 3p instead of compound 3a. Also, a comparative EL element 1 was fabricated using comparative compound 1 instead of compound 3a. Each of the produced organic electroluminescent devices was made to emit light at a current density of 6.3 mA/cm ² in an environment of 20° C. As a result, all of the devices showed good performance. Next, the EL element 1 and the comparative EL element 1 were made to emit light at a current density of 6.3 mA/cm ² in an environment of 100°C. The external quantum efficiency (EQE) and driving voltage after 1 hour were measured. As a result, EL element 1 did not change at all even after 1 hour, but the external quantum efficiency of EL element 1 decreased by 1.1%, and the driving voltage increased. up to 0.22V. Even after the same test was performed in an environment of 60° C. or 80° C., the external quantum efficiency and driving voltage of the EL element 1 did not change at all after 1 hour. Thereby, it was confirmed that in the device using the compound represented by the general formula (1), the thermal stability of the device is high, and the light emitting performance is stable even in a high-temperature environment.

(Example 2) The following thin films were laminated at a vacuum degree of 5.0×10 ^-5 Pa on a glass substrate on which an anode composed of indium tin oxide (ITO) with a film thickness of 100 nm was formed by the vacuum evaporation method to produce organic electroluminescent elements. First, HATCN with a thickness of 10nm is formed on ITO, NPD with a thickness of 30nm is formed on it, and TrisPCz with a thickness of 10nm is formed thereon. Next, the luminescent material (G1), delayed fluorescent material (TADF21), and compound 31 were co-evaporated from different deposition sources to form a layer with a thickness of 40 nm, which was used as a luminescent layer. At this time, the content of the luminescent material was 1.4% by mass, the content of the delayed fluorescent material was 35.0% by mass, and the content of Compound 31 was 63.6% by mass. Next, after forming SF3-TRZ to a thickness of 10 nm, Liq and SF3-TRZ were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. The contents of Liq and SF3-TRZ in this layer were set to 30% by mass and 70% by mass, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescent element. This element is referred to as the EL element 3 . Also, EL elements 4 and 5 were fabricated using compounds 3m and 7m instead of compound 31. Electricity was applied to each of the produced organic electroluminescence elements, and as a result, delayed fluorescence from the light-emitting material (G1) was observed. The fabricated organic electroluminescent element was driven at 6.3mA/cm ² at 20°C, and the external quantum efficiency (EQE) and initial driving voltage were measured. Also, each organic electroluminescence element was driven at a current density of 12.6 mA/cm ² , and the time until the emission intensity became 95% of that at the start of driving was measured (LT95). The measurement results are shown in Table 2. EQE and LT95 in Table 2 are shown as relative values when LT95 of the EL element 3 is set to 1, and the driving voltage is shown as a relative value with the EL element 3 as a reference (0). The measurement results show that, even when the host material, delayed fluorescent material and fluorescent material are used in the light-emitting layer, the luminous efficiency of the device using the compound represented by the general formula (1) as the host material is high, and the driving voltage Average low, component life is long.

[Table 2] Part number Electron barrier material EQE (%) Driving voltage (V) LT95 EL element 3 Compound 3l 1 0 1 EL element 4 Compound 3m 1.08 times 0.06 1.1 times EL element 5 Compound 7m 1.03 times 0.05 1.2 times

(Example 3) The following thin films were laminated at a vacuum degree of 5.0×10 ^-5 Pa on a glass substrate on which an anode composed of indium tin oxide (ITO) with a film thickness of 100 nm was formed by the vacuum evaporation method to produce organic electroluminescent elements. Firstly, HATCN with a thickness of 10 nm was formed on ITO, NPD with a thickness of 30 nm was formed on it, and then compound 3l was formed with a thickness of 10 nm on it. Next, the luminescent material (G2), delayed fluorescent material (TADF72), and comparative compound A were co-evaporated from different deposition sources to form a layer with a thickness of 40 nm, which was used as a luminescent layer. At this time, the content of the luminescent material was 0.8% by mass, the content of the delayed fluorescent material was 35.0% by mass, and the content of Compound 31 was 64.2% by mass. Next, after forming SF3-TRZ to a thickness of 10 nm, Liq and SF3-TRZ were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. The contents of Liq and SF3-TRZ in this layer were set to 30% by mass and 70% by mass, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescent element. This element is referred to as an EL element 6 . Also, an EL element 7 was fabricated using Compound 7m instead of Compound 3l. As a result of energizing each produced organic electroluminescence element, delayed fluorescence from the light-emitting material (G2) was observed. The fabricated organic electroluminescent element was driven at 6.3mA/cm ² at 20°C, and the external quantum efficiency (EQE) and initial driving voltage were measured. Also, each organic electroluminescence element was driven at a current density of 12.6 mA/cm ² , and the time until the emission intensity became 95% of that at the start of driving was measured (LT95). The measurement results are shown in Table 3. EQE and LT95 in Table 3 are shown as relative values when LT95 of the EL element 6 is set to 1, and the driving voltage is shown as a relative value with the EL element 6 as a reference (0). The measurement results show that the components using the compound represented by the general formula (1) as the electron barrier material have high luminous efficiency, low driving voltage and long service life of the components.

[table 3] Part number Electron barrier material EQE (%) Driving voltage (V) LT95 EL element 6 Compound 3l 1 0 1 EL element 7 Compound 7m 0.88 times 0.09 1.5 times [chemical formula 108]

1: Substrate 2: anode 3: Hole injection layer 4: Hole transport layer 5: Luminous layer 6: Electron transport layer 7: Cathode

FIG. 1 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescence device.

1: Substrate

2: anode

3: Hole injection layer

4: Hole transport layer

5: Luminous layer

6: Electron transport layer

7: Cathode

Claims (29)

A compound represented by the following general formula (1), [Chemical Formula 1]

In the general formula (1), R ¹ to R ⁷ independently represent a hydrogen atom, a deuterium atom, an alkyl group that may be deuterated or a substituted or unsubstituted aryl group, and at least one of R ¹ to R ⁴ is a substituted or unsubstituted aryl group, and each of R ⁸ to R ¹⁹ independently represents a hydrogen atom, a deuterium atom, or an alkyl group that may be deuterated. The compound according to claim 1, wherein only one of R ¹ to R ⁴ is substituted or unsubstituted aryl. The compound as claimed in claim 1, wherein R ² is substituted or unsubstituted aryl. The compound as claimed in claim 1, wherein R ⁴ is substituted or unsubstituted aryl. The compound as described in claim 1, wherein The aforementioned substituted or unsubstituted aryl group is a substituted or unsubstituted phenyl group. The compound as described in claim 1, wherein The aforementioned substituted or unsubstituted aryl group is a substituted or unsubstituted dibenzofuryl group or a substituted or unsubstituted dibenzothienyl group. The compound according to any one of claim 1 to claim 6, wherein R ⁵ to R ¹¹ are each independently a hydrogen atom or a deuterium atom. The compound according to any one of claim 1 to claim 6, wherein R ¹² to R ¹⁹ are each independently a hydrogen atom or a deuterium atom. The compound according to any one of claim 1 to claim 6, wherein at least one of R ¹ to R ⁴ contains a deuterium atom. The compound according to any one of claim 1 to claim 6, wherein at least one of R ¹² to R ¹⁹ contains a deuterium atom. A use of the compound described in any one of claim 1 to claim 10 as a host material. The use as a host material as described in claim 11 is used together with a delayed fluorescent material. The use as the host material as described in claim 11 is used together with the compound represented by the following general formula (G), general formula (G) [chemical formula 2]

In the general formula (G), one of X ¹ and X ² is a nitrogen atom, the other is a boron atom, and R ¹ to R ²⁶ , A ¹ , and A ² independently represent a hydrogen atom, a deuterium atom or a substituted R ¹ and R ² , R ² and R ³ , R 3 and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and ^{R 9 ,} R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R 14 , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 17 and} R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ^{21 and R 22 , R 22 and} R ²³ , R ²³ and R ²⁴ , ^{R 24 and} R ²⁵ , R ²⁵ and R ²⁶ may be bonded to each other and A ring structure is formed in which, when ^X1 is a nitrogen atom, ^R17 and ^R18 are bonded to each other to form a single bond to form a pyrrole ring, and when ^X2 is a nitrogen atom, ^R21 and ^R22 are bonded to each other to form single bond to form the pyrrole ring. A use of the compound described in any one of claim 1 to claim 10 as an electron barrier material. The use as an electron barrier material as described in Claim 14 is used in combination with a delayed fluorescent material. The use as an electron barrier material as described in Claim 14, which is used in combination with a compound represented by the following general formula (G), general formula (G) [chemical formula 3]

In the general formula (G), one of X ¹ and X ² is a nitrogen atom, the other is a boron atom, and R ¹ to R ²⁶ , A ¹ , and A ² independently represent a hydrogen atom, a deuterium atom or a substituted R ¹ and R ² , R ² and R ³ , R 3 and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and ^{R 9 ,} R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R 14 , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 17 and} R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ^{21 and R 22 , R 22 and} R ²³ , R ²³ and R ²⁴ , ^{R 24 and} R ²⁵ , R ²⁵ and R ²⁶ may be bonded to each other and A ring structure is formed in which, when ^X1 is a nitrogen atom, ^R17 and ^R18 are bonded to each other to form a single bond to form a pyrrole ring, and when ^X2 is a nitrogen atom, ^R21 and ^R22 are bonded to each other to form single bond to form the pyrrole ring. A composition, which is doped with a delayed fluorescent material in the compound described in any one of claim 1 to claim 10. The composition as described in claim 17, which is in the form of a film. The composition as described in claim 17, wherein The aforementioned retarded fluorescent material is a compound having a cyanobenzene structure in which one cyano group is substituted with a benzene ring. The composition as described in claim 17, wherein The aforementioned retarded fluorescent material is a compound having a dicyanobenzene structure in which two cyano groups are substituted with benzene rings. The composition as described in Claim 17, wherein the aforementioned delayed fluorescent material is a compound represented by the following general formula (E), general formula (E) [chemical formula 4]

In the general formula (E), R ¹ to R ⁴ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a donor group, and, Two or more of R ¹ to R ⁴ are donor groups, at least one of the two or more donor groups is a substituted ring-condensed carbazol-9-yl group, and X ¹ to X ³ are independently represents N or C (R), but at least one of X ¹ to X ³ is N, R represents a hydrogen atom, a deuterium atom or a substituent, and Ar ¹ and Ar ² independently represent substituted or unsubstituted aryl groups , L ¹ represents a single bond or a divalent linking group. The composition according to claim 17, further comprising a fluorescent compound having a lowest excited singlet energy lower than that of the host material and the delayed fluorescent material. The composition as described in any one of claim 17 to claim 22, wherein the aforementioned delayed fluorescent material or the aforementioned fluorescent compound is a compound represented by the following general formula (G), general formula (G) [chemical formula 5]

In the general formula (G), one of X ¹ and X ² is a nitrogen atom, the other is a boron atom, and R ¹ to R ²⁶ , A ¹ , and A ² independently represent a hydrogen atom, a deuterium atom or a substituted R ¹ and R ² , R ² and R ³ , R 3 and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁸ and ^{R 9 ,} R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹³ and R 14 , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , R ¹⁶ and R ¹⁷ , ^{R 17 and} R ¹⁸ , R ¹⁸ and R ¹⁹ , R ¹⁹ and R ²⁰ , R ²⁰ and R ²¹ , R ^{21 and R 22 , R 22 and} R ²³ , R ²³ and R ²⁴ , ^{R 24 and} R ²⁵ , R ²⁵ and R ²⁶ may be bonded to each other and A ring structure is formed in which, when ^X1 is a nitrogen atom, ^R17 and ^R18 are bonded to each other to form a single bond to form a pyrrole ring, and when ^X2 is a nitrogen atom, ^R21 and ^R22 are bonded to each other to form single bond to form the pyrrole ring. An organic light-emitting device having a layer composed of the composition described in any one of claim 17 to claim 23. The organic light-emitting device as claimed in claim 24, wherein The foregoing layer is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms. The organic light-emitting device as claimed in claim 24, wherein The foregoing layer is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. The organic light-emitting device according to any one of claim 24 to claim 26, which is an organic electroluminescent device. The organic light-emitting device according to any one of claim 24 to claim 26, wherein The composition does not contain the fluorescent compound, and the largest component of the light emission from the device is light emission from the delayed fluorescent material. The organic light-emitting device according to any one of claim 24 to claim 26, wherein The composition includes the fluorescent compound, and the largest component of the luminescence from the device is the luminescence from the fluorescent compound.

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