TW202313931A - Electron barrier material, organic semiconductor element and compound - Google Patents

Abstract

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

Description

Electron barrier materials, organic semiconductor elements and compounds

The present invention relates to a compound useful as an electron barrier material and an organic semiconductor device using the compound.

We are actively conducting research to improve the performance of organic semiconductor devices such as organic electroluminescent devices (organic EL devices). For example, in order to improve the device life and driving voltage of organic electroluminescent elements, it is desired to improve the functions of materials related to charge transport such as electron transport materials, hole transport materials, electron barrier materials, and hole barrier materials. Development or improvement of other materials. For example, the electron barrier material is a material that is provided between the light-emitting layer and the hole transport layer to prevent electrons present in the light-emitting layer from dropping from the light-emitting layer to the hole transport layer, and undertakes hole transport from the hole transport layer The material of the electron barrier layer to the function of the light-emitting layer. As long as an excellent electron barrier material is used, the recombination probability of electrons and holes in the light-emitting layer will be increased, and the lifetime of the device will be prolonged. Conventionally, various compounds have been proposed as electron barrier materials. For example, Patent Document 1 proposes a compound having the following structure.

[chemical formula 1]

[Patent Document 1] WO2010/140482

However, there is room for improvement in the lifetime of an organic electroluminescent device using the above compound as an electron barrier material. Therefore, the inventors of the present invention have earnestly studied to provide an electron barrier material capable of prolonging the device life when used in an organic electroluminescence device.

[式中，R ¹～R ⁵分別獨立地表示氘原子或不包含氰基的取代基。R ¹～R ⁵不與其他R ¹～R ⁵或Ar鍵結而形成環狀結構，但是相鄰之R ³彼此可以相互鍵結而形成苯并氟骨架或苯并噻吩并骨架。n1、n3、n5分別獨立地表示0～4中的任一個整數，n2表示0～3中的任一個整數，n4表示0～2中的任一個整數。X表示氧原子或硫原子。Ar表示單環伸芳基或單環雜伸芳基，前述單環伸芳基及前述單環雜伸芳基可以經氘原子或不包含氰基的取代基取代。] [2]如[1]所述之電子障壁材料，其中，前述化合物具有下述通式（2A）所表示之結構。 [化學式3]

[式中，R ¹～R ⁶分別獨立地表示氘原子或不包含氰基的取代基。R ¹～R ⁶不與其他R ¹～R ⁶鍵結而形成環狀結構，但是相鄰之R ³彼此可以相互鍵結而形成苯并氟骨架或苯并噻吩并骨架。n1、n3、n5分別獨立地表示0～4中的任一個整數，n2、n6分別獨立地表示0～3中的任一個整數，n4表示0～2中的任一個整數。X表示氧原子或硫原子。] [3]如[1]所述之電子障壁材料，其中，前述化合物具有下述通式（2B）所表示之結構。 [化學式4]

[式中，R ¹～R ⁶分別獨立地表示氘原子或不包含氰基的取代基。R ¹～R ⁶不與其他R ¹～R ⁶鍵結而形成環狀結構，但是相鄰之R ³彼此可以相互鍵結而形成苯并氟骨架或苯并噻吩并骨架。n1、n3、n5分別獨立地表示0～4中的任一個整數，n2、n6分別獨立地表示0～3中的任一個整數，n4表示0～2中的任一個整數。X表示氧原子或硫原子。] [4]如[1]所述之電子障壁材料，其中，前述化合物具有下述通式（3）所表示之結構。 [化學式5]

[式中，R ¹～R ⁶分別獨立地表示氘原子或不包含氰基的取代基。R ¹～R ⁶不與其他R ¹～R ⁶鍵結而形成環狀結構，但是相鄰之R ³彼此可以相互鍵結而形成苯并氟骨架或苯并噻吩并骨架。n1、n3、n5分別獨立地表示0～4中的任一個整數，n2、n6分別獨立地表示0～3中的任一個整數，n4表示0～2中的任一個整數。其中，n1+n3+n4+n5為1以上。R ¹及R ³～R ⁵中的一個或兩個表示可以被氘化的烷基或可以經氘原子取代的苯基。X表示氧原子或硫原子。] [5]如[2]至[4]之任一項所述之電子障壁材料，其中，n1、n2、n6為0。 [6]如[1]至[5]之任一項所述之電子障壁材料，其中，n3～n5分別獨立地為0或1。 [7]如[1]所述之電子障壁材料，其係具有下述中的任一個結構。 [化學式6]

[8]如[1]至[7]之任一項所述之電子障壁材料，其係用於與下述通式（G）所表示之化合物組合使用。 通式（G） [化學式7]

[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。 [9]一種有機半導體元件，其係包含[1]至[7]之任一項所述之電子障壁材料。 [10]如[9]所述之有機半導體元件，其中，前述有機半導體元件為有機電致發光元件，該有機電致發光元件具有陽極、陰極及在前述陽極與前述陰極之間包括包含前述電子障壁材料之電子障壁層和發光層之至少兩層有機層。 [11]如[10]所述之有機半導體元件，其中，前述發光層包含主體材料和延遲螢光材料。 [12]如[10]所述之有機半導體元件，其中，前述發光層包含主體材料、延遲螢光材料及螢光發光材料，來自元件的發光中來自前述螢光發光材料的發光量最大。 [13]如[10]至[12]之任一項所述之有機半導體元件，其中，前述發光層與前述電子障壁層相鄰。 [14]如[10]至[13]之任一項所述之有機半導體元件，其中，前述發光層包含前述通式（G）所表示之化合物。 [15]如[10]至[14]之任一項所述之有機半導體元件，其中，前述發光層包含下述通式（4）所表示之化合物。 [化學式8]

[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9]

[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10]

[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。] [16]一種化合物，其係由前述通式（3）表示，其中，在n3+n4+n5為0時，R ¹不是未經取代的苯基。 [發明效果] As a result of painstaking studies, the present inventors discovered that a compound having a specific structure functions as an excellent electron barrier material. This invention was made based on this knowledge, Specifically, it has the following structures. [1] An electron barrier material comprising a compound represented by the following general formula (1). [chemical formula 2]

[wherein, R ¹ to R ⁵ each independently represent a deuterium atom or a substituent not containing a cyano group. R ¹ to R ⁵ are not bonded to other R ¹ to R ⁵ or Ar to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent any integer of 0-4, n2 represents any integer of 0-3, and n4 represents any integer of 0-2. X represents an oxygen atom or a sulfur atom. Ar represents a monocyclic arylylene group or a monocyclic heteroarylylene group, and the aforementioned monocyclic arylylene group and the aforementioned monocyclic heteroarylylene group may be substituted by a deuterium atom or a substituent not containing a cyano group. ] [2] The electron barrier material according to [1], wherein the compound has a structure represented by the following general formula (2A). [chemical formula 3]

[wherein, R ¹ to R ⁶ each independently represent a deuterium atom or a substituent not containing a cyano group. R ¹ to R ⁶ are not bonded to other R ¹ to R ⁶ to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent any integer of 0-4, n2 and n6 each independently represent any integer of 0-3, and n4 represents any integer of 0-2. X represents an oxygen atom or a sulfur atom. ] [3] The electron barrier material according to [1], wherein the compound has a structure represented by the following general formula (2B). [chemical formula 4]

[wherein, R ¹ to R ⁶ each independently represent a deuterium atom or a substituent not containing a cyano group. R ¹ to R ⁶ are not bonded to other R ¹ to R ⁶ to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent any integer of 0-4, n2 and n6 each independently represent any integer of 0-3, and n4 represents any integer of 0-2. X represents an oxygen atom or a sulfur atom. ] [4] The electron barrier material according to [1], wherein the compound has a structure represented by the following general formula (3). [chemical formula 5]

[wherein, R ¹ to R ⁶ each independently represent a deuterium atom or a substituent not containing a cyano group. R ¹ to R ⁶ are not bonded to other R ¹ to R ⁶ to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent any integer of 0-4, n2 and n6 each independently represent any integer of 0-3, and n4 represents any integer of 0-2. However, n1+n3+n4+n5 is 1 or more. One or both of R ¹ and R ³ to R ⁵ represent an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom. [5] The electron barrier material according to any one of [2] to [4], wherein n1, n2, and n6 are 0. [6] The electron barrier material according to any one of [1] to [5], wherein n3 to n5 are each independently 0 or 1. [7] The electron barrier material according to [1], which has any one of the following structures. [chemical formula 6]

[8] The electron barrier material according to any one of [1] to [7], which is used in combination with a compound represented by the following general formula (G). General formula (G) [Chemical formula 7]

[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(R ²⁷ )-. R ²⁷ represents a hydrogen atom, a deuterium atom or a substituent. [9] An organic semiconductor device comprising the electron barrier material described in any one of [1] to [7]. [10] The organic semiconductor element as described in [9], wherein the organic semiconductor element is an organic electroluminescence element, and the organic electroluminescence element has an anode, a cathode, and an electrode containing the electrons between the anode and the cathode. The electron barrier layer of the barrier material and at least two organic layers of the light emitting layer. [11] The organic semiconductor device according to [10], wherein the light emitting layer includes a host material and a delayed fluorescent material. [12] The organic semiconductor device according to [10], wherein the light-emitting layer includes a host material, a delayed fluorescent material, and a fluorescent light-emitting material, and the amount of light emitted from the fluorescent light-emitting material is the largest among the light emitted from the device. [13] The organic semiconductor device according to any one of [10] to [12], wherein the light emitting layer is adjacent to the electron barrier layer. [14] The organic semiconductor device according to any one of [10] to [13], wherein the light-emitting layer contains the compound represented by the general formula (G). [15] The organic semiconductor device according to any one of [10] to [14], wherein the light-emitting layer contains a compound represented by the following general formula (4). [chemical formula 8]

[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), and the remaining two of R ²¹ to R ²³ and R ²⁴ and R ²⁵ At least one of R ²¹ to R 25 represents a group represented by the following general formula (6), and the rest of R 21 to R ²⁵ represent a hydrogen atom or a substituent (wherein, the substituent described here is not a cyano group, the following general formula ( 5) the group represented by, the group represented by the following general formula (6)). ] [chemical formula 9]

[In 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 10]

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

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

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 invention, 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, in the present invention, "consisting of -" means consisting of only those described above "consisting of -" and does not include other things. Also, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention can be substituted with deuterium atoms ( ² H, deuterium D). In the chemical structural formulas in this specification, a hydrogen atom is represented by H or omitted. For example, when an atom that is bonded to a carbon atom of the ring skeleton of a benzene ring is omitted, it is assumed that the H at the omitted site is bonded to a carbon atom of the ring skeleton. In this specification, the term "substituent" means an atom or an atom group other than a hydrogen atom and a deuterium atom. On the other hand, the expression "substituted or unsubstituted" and "may be substituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent. Also, "transparent" in the present invention means that the transmittance of visible light is 50% or more, preferably 80% or more, more preferably 90% or more, still more preferably 99% or more. The transmittance of visible light can be measured with an ultraviolet-visible spectrophotometer.

(Compound Represented by General Formula (1)) In the present invention, a compound represented by the following general formula (1) is used. [chemical formula 11]

In the general formula (1), R ¹ to R ⁵ each independently represent a deuterium atom or a substituent not containing a cyano group. In one aspect of the present invention, the substituents of R ¹ to R ⁵ are each independently a substituent whose Hammett's σp value is in the range of -0.3 to 0.3. In a preferred aspect of the present invention, the substituents of R ¹ to R ⁵ are each independently a substituent whose Hammett's σp value is in the range of -0.2 to 0.2. In a preferred aspect of the present invention, the substituents of R ¹ to R ⁵ are independently substituents with a Hammett's σp value in the range of -0.1 to 0.1. In one aspect of the present invention, the substituents of R ¹ to R ⁵ are each independently a substituent with a Hammett's σp value in the range of greater than 0 and less than 0.3. In one aspect of the present invention, the substituents of R ¹ to R ⁵ are each independently a substituent whose Hammett's σp value is in the range of -0.3 or more and less than 0. Among them, "Hammett's σp value" is proposed by LP Hammett, and is a quantification of the effect of substituents on the reaction rate or equilibrium of the para-substituted benzene derivative. Specifically, it is the following formula established between the substituents in the p-substituted benzene derivatives and the reaction rate constant or equilibrium constant: log(k/k ₀ )=ρσp or log(K/K ₀ )=ρσp A constant (σp) specific to the substituent in . In the above formula, k ₀ represents the rate constant of benzene derivatives without substituents, k represents the rate constant of benzene derivatives substituted by substituents, K ₀ represents the equilibrium constant of benzene derivatives without substituents, K represents an equilibrium constant of a benzene derivative substituted by a substituent, and ρ represents a reaction constant determined by the type and conditions of the reaction. For the description of "Hammett's σp value" in the present invention and the numerical value of each substituent, refer to the σp value of Hansch, C.et.al., Chem.Rev., 91, 165-195 (1991) related records. There is a tendency that a group having a negative Hammett's σp value exhibits electron donating property (donating property) and a group having a positive Hammett's σp value exhibits electron withdrawing property (accepting property). In one aspect of the present invention, R ¹ to R ⁵ are each independently a substituent having no lone electron pair. In one aspect of the present invention, R ¹ to R ⁵ are each independently a substituent without π electrons.

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

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

R ¹ to R ⁵ are not bonded to other R ¹ to R ⁵ or Ar to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. Therefore, the dibenzofuran (three-ring structure) on the left side in the general formula (1) becomes a structure of four or more rings without further ring-condensation. Also, benzofluorocarbazole (5-ring structure), benzothienocarbazole (5-ring structure), bisbenzofluorocarbazole (7-ring structure), and bisbenzothiophene on the right side of the general formula (1) And carbazole (7-ring structure), etc. will not be further condensed with the ring. Furthermore, it is preferable that the structure on the right side of the general formula (1) is a 5-ring structure. That is, in a preferred aspect of the present invention, R ³ are not bonded to each other to form a ring structure.

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

In the general formula (1), X represents an oxygen atom or a sulfur atom. In one aspect of the present invention, X is a sulfur atom. In a preferred aspect of the present invention, X is an oxygen atom. In the general formula (1), the single bond extends in the lower left direction from the ortho position of the benzene ring bonded to the right side of X. This single bond may be bonded to any one of the 1-4 positions of the carbazole structure located on the right side of Ar in the general formula (1). In addition, X may be bonded to any one of the 1-4 positions of the carbazole structure located on the right side of Ar in the general formula (1). Wherein, the single bond and X are respectively bonded to adjacent carbon atoms of the skeleton constituting the carbazole structure. Therefore, when a single bond is bonded at 2-position, X is bonded at 1-position or 3-position. When a single bond is bonded at the 3rd position, X is bonded at the 2nd or 4th position. When a single bond is bonded at 1 position, X is bonded at 2 positions. When a single bond is bonded at 4-position, X is bonded at 3-position. In the general formula (1), X is described above the single bond, but the general formula (1) also includes the structure of the following general formula (1′) in which the single bond is located below the X. [chemical formula 12]

As the benzofluorocarbazol-9-yl group bonded to Ar of the general formula (1), substituted or unsubstituted benzofluoro[2,3-a]carbazol-9-yl groups can be used. Also, a substituted or unsubstituted benzofluoro[3,2-a]carbazol-9-yl group can also be used. In addition, substituted or unsubstituted benzofluoro[2,3-b]carbazol-9-yl groups can also be used. In addition, substituted or unsubstituted benzofluoro[3,2-b]carbazol-9-yl groups can also be used. In addition, substituted or unsubstituted benzofluoro[2,3-c]carbazol-9-yl groups can also be used. In addition, substituted or unsubstituted benzofluoro[3,2-c]carbazol-9-yl groups can also be used. As the benzothienocarbazol-9-yl group bonded to Ar of the general formula (1), a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be used. In addition, a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be used. As the bisbenzofluorocarbazol-9-yl group bonded to Ar of the general formula (1), substituted or unsubstituted bisbenzofluoro[2,3-a:2',3'-f ]carbazol-9-yl. Also, a substituted or unsubstituted bisbenzofluoro[3,2-a:3',2'-f]carbazol-9-yl group can also be used. Also, a substituted or unsubstituted bisbenzofluoro[2,3-b:2',3'-e]carbazol-9-yl group can also be used. Also, substituted or unsubstituted bisbenzofluoro[3,2-b:3',2'-e]carbazol-9-yl can also be used. Also, a substituted or unsubstituted bisbenzofluoro[2,3-c:2',3'-d]carbazol-9-yl group can also be used. Also, substituted or unsubstituted bisbenzofluoro[3,2-c:3',2'-d]carbazol-9-yl can also be used. As the bisbenzothienocarbazol-9-yl group bonded to Ar of the general formula (1), substituted or unsubstituted bisbenzothieno[2,3-a:2',3' -f]carbazol-9-yl. In addition, a substituted or unsubstituted bisbenzothieno[3,2-a:3',2'-f]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted bisbenzothieno[2,3-b:2',3'-e]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted bisbenzothieno[3,2-b:3',2'-e]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted bisbenzothieno[2,3-c:2',3'-d]carbazol-9-yl group can also be used. In addition, a substituted or unsubstituted bisbenzothieno[3,2-c:3',2'-d]carbazol-9-yl group can also be used.

Specific examples of substituted or unsubstituted benzofluorocarbazol-9-yl and substituted or unsubstituted benzothienocarbazol-9-yl bonded to Ar of the general formula (1) are illustrated in the following. However, the structures that can be adopted in the present invention are not limitedly interpreted by these specific examples. In the present invention, * represents a bonding position. Ph represents unsubstituted phenyl. Also, in the present invention, the methyl group is not expressed as CH ₃ and the expression of CH ₃ is omitted as in the lower left of D7. [chemical formula 13]

Those in which all the hydrogen atoms in D1 to D64 are replaced with deuterium atoms are exemplified here as D1(D) to D64(D). In addition, those in which only the hydrogen atoms bonded to the alkyl groups of D7-D18 and D37-D48 above are replaced with deuterium atoms are exemplified in the form of D7(R)-D18(R), D37(R)-D48(R) here. Furthermore, those in which only the hydrogen atoms bonded to the phenyl groups of D19 to D30 and D49 to D60 are replaced with deuterium atoms are exemplified in the form of D19 (Ph) to D30 (Ph), D49 (Ph) to D60 (Ph) here. In a preferred aspect of the present invention, the substituted or unsubstituted benzofluorocarbazol-9-yl and substituted or unsubstituted benzothiophene bonded to Ar of the general formula (1) And carbazol-9-yl from D1 ~ D60, D1 (D) ~ D60 (D), D7 (R) ~ D18 (R), D37 (R) ~ D48 (R), D19 (Ph) ~ D30 (Ph ), D49(Ph)～D60(Ph), more preferably from D1～D30, D1(D)～D30(D), D7(R)～D18(R), D19(Ph)～D30(Ph ) to select. In a preferred aspect of the present invention, from D7 to D30, D37 to D60, D7 (D) to D30 (D), D37 (D) to D60 (D), D7 (R) to D18 (R) , D37(R)～D48(R), D19(Ph)～D30(Ph), D49(Ph)～D60(Ph), more preferably from D19～D30, D49～D60, D19(D)～ D30(D), D49(D)～D60(D), D19(Ph)～D30(Ph), D49(Ph)～D60(Ph) for selection, more preferably from D19～D30, D19(D) ~D30(D), D19(Ph)~D30(Ph) to select.

In the general formula (1), Ar represents a monocyclic arylylene group or a monocyclic heteroarylylene group. The monocyclic arylylene group mentioned here means a phenylene group without ring shrinkage. Also, the monocyclic heteroarylylene group means an aromatic ring group having a single ring structure without ring condensation and containing a heteroatom as a ring skeleton constituting atom. The number of atoms constituting the ring skeleton of the monocyclic heteroarylylene group is preferably 5 to 7, more preferably 5 or 6, for example, 6 atoms can be used. Examples of the heteroatom constituting the ring skeleton of the monocyclic heteroarylenyl group include nitrogen atom, oxygen atom and sulfur atom, and nitrogen atom is preferred. Examples of the ring constituting the monocyclic heteroarylenyl group include a pyridine ring, a pyridine ring, a pyrimidine ring, a pyridine ring and a tripyridine ring. When the carbazole expressed on the right side of the general formula (1) is bonded at the 1-position of the single ring constituting Ar, the dibenzofuran expressed on the left side of the general formula (1) can be in any of the single rings constituting Ar. positional bond. Preferably, dibenzofuran is bonded to the 3-position or 4-position of the monocyclic ring constituting Ar. Especially preferred is the case where dibenzofuran is bonded at the 3-position of the monocyclic ring constituting Ar (for example, the case where Ar is a substituted or unsubstituted 1,3-phenylene group), and is more effective than dibenzofuran in the The case of 2-position or 4-position bonding is more excellent.

The monocyclic arylylene and monocyclic heteroarylylene that Ar can adopt may be substituted with a deuterium atom or a substituent not containing a cyano group, respectively. In a preferred aspect of the present invention, a substituent whose Hammett's σp value is in the range of -0.3 to 0.3 is selected as the substituent. For the description and preferable range of the substituent whose Hammett's σp value is in the range of -0.3 to 0.3, the corresponding description of R ¹ to R ⁵ can be referred to. In one aspect of the present invention, a group without a lone electron pair is selected as a substituent. In one aspect of the present invention, a group without π electrons is selected as a substituent. In a preferred aspect of the present invention, one or two groups selected from the group consisting of alkyl (for example, carbon number 1-40) and aryl group (for example, carbon number 6-30) are selected Groups obtained by combining the above are used as substituents. In a preferred aspect of the present invention, an alkyl group having 1 to 30 carbons is selected as the substituent. Regarding the description and preferable range of the alkyl group, the corresponding descriptions of R ¹ to R ⁵ can be referred to. In a preferred aspect of the present invention, Ar is a phenylene group that may be substituted by 1 to 4 alkyl groups with 1 to 20 carbons or may be substituted by 1 to 3 alkyl groups with 1 to 20 carbons. Monocyclic heteroaryl. In a preferred aspect of the present invention, Ar is an unsubstituted phenylene group or an unsubstituted monocyclic heteroarylylene group.

Specific examples of Ar in the general formula (1) are shown below, but the structures that can be employed in the present invention are not limitedly interpreted by these specific examples. t-Bu represents a tertiary butyl group, and Ph represents an unsubstituted phenyl group. [chemical formula 14]

Those in which all the hydrogen atoms of Ar1 to Ar15 are replaced with deuterium atoms are exemplified here as Ar1(D) to Ar15(D). Also, those in which only hydrogen atoms bonded to the alkyl groups of Ar2 to Ar9 are substituted with deuterium atoms are exemplified here as Ar2 (R) to Ar9 (R). Furthermore, what replaced only the hydrogen atom bonded to the phenyl group of Ar10 with a deuterium atom is shown here as Ar10 (Ph). In a preferred aspect of the present invention, Ar of the general formula (1) is selected from Ar1～Ar9, Ar1(D)～Ar9(D), Ar2(R)～Ar9(R), more preferably from Ar1 to Ar9 are selected. In a preferred aspect of the present invention, Ar in the general formula (1) is Ar1 or Ar1(D), more preferably Ar1.

The dibenzofuran represented on the left side of the general formula (1) may be bonded to Ar at any one of the 1-4 positions. In a preferred aspect of the present invention, dibenzofuran is bonded to Ar at the 2-position. In one aspect of the present invention, dibenzofuran is bonded to Ar at the 1-position. In one aspect of the present invention, dibenzofuran is bonded to Ar at the 3-position. In one aspect of the present invention, dibenzofuran is bonded to Ar at the 4-position. In addition, the 1-4 positions of dibenzofuran are as follows. [chemical formula 15]

Specific examples of the dibenzofuran group bonded to Ar of the general formula (1) are shown below, but the structures that can be employed in the present invention are not limitedly interpreted by these specific examples. [chemical formula 16]

Those in which all the hydrogen atoms of B1 to B12 are replaced with deuterium atoms are exemplified here as B1(D) to B12(D). In addition, those in which only the hydrogen atoms bonded to the alkyl groups of B2, B5, B8, and B11 above are replaced with deuterium atoms are exemplified in the form of B2 (R), B5 (R), B8 (R), and B11 (R). here. Furthermore, those in which only the hydrogen atoms bonded to the phenyl groups of B3, B6, B9, and B12 are substituted with deuterium atoms are exemplified in the form of B3 (Ph), B6 (Ph), B9 (Ph), and B12 (Ph) here. In a preferred aspect of the present invention, the dibenzofuran group bonded to Ar of the general formula (1) is from B1 to B3, B1 (D) to B3 (D), B2 (R), B3 ( Ph), more preferably from B1 to B3. In one aspect of the present invention, the dibenzofuran group bonded to Ar of the general formula (1) is from B1, B4, B7, B10, B1(D), B4(D), B7(D), B10 (D) Select, more preferably select from B1, B4, B7, B10.

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, 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 phenyl groups. The "phenyl group which may be substituted with an alkyl group" in the present invention means that at least one of the five hydrogen atoms present in the phenyl group may be substituted with an alkyl group. In one aspect of the present invention, the phenyl group is substituted with 0-3 alkyl groups. For example, substituted with 0 to 2 alkyl groups. In one aspect of the invention, the phenyl groups are not substituted with alkyl groups. The carbon number of the alkyl group substituted with phenyl is preferably 1-6, more preferably 1-4. For example, 4-methylphenyl, 3-methylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2,3,4,5,6 -Heptamethylphenyl, 4-isopropylphenyl, 3-isopropylphenyl, 3,5-diisopropylphenyl, 4-tertiary butylphenyl, 3-tertiary butylphenyl group, 3,5-two tertiary butylphenyl. In addition, a group in which all hydrogen atoms present in the alkyl substituent in these specific examples are substituted with deuterium atoms can also be exemplified. Furthermore, a group in which all hydrogen atoms present in these specific examples are substituted with deuterium atoms can also be exemplified. 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 the general formula (1), no cyano group is present. In a preferred aspect of the present invention, the general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms. In a preferred aspect of the present invention, the general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms. The molecular weight of the compound represented by general formula (1) is 499 or more, Preferably it is 700 or less, More preferably, it is 600 or less, For example, it may be 550 or less, and may be 530 or less.

As a compound represented by General formula (1), the compound represented by following General formula (2A) can be illustrated preferably. [chemical formula 17]

As a compound represented by General formula (1), the compound represented by following General formula (2B) can be illustrated preferably. [chemical formula 18]

For the definitions and descriptions of R ¹ to R ⁵ , n1 to n5, and X in the general formula (2A) and the general formula (2B), reference can be made to the corresponding definitions and descriptions of the general formula (1). For the definition and description of R ⁶ in the general formula (2A) and the general formula (2B), reference can be made to the definition and description of R ¹ to R ⁵ in the general formula (1). n6 in general formula (2A) and general formula (2B) is any integer among 0-3. n6 can be selected from the range of 0 to 2 or set to 0 or 1, and 0 is also preferable. n1-n6 in general formula (2A) and general formula (2B) can each independently be selected within the range of 0-2, or can be set to 0 or 1. Also, all of n1 to n6 may be 0. In the structures represented by the general formula (2A) and the general formula (2B), it is particularly preferred that the (R ⁶ ) _n6 -bonded phenylene group in the general formula (2A) and the general formula (2B) is 1,3- The structure of phenylene (methyl phenylene).

As a compound represented by General formula (1), the compound represented by following General formula (3) can be illustrated particularly preferably. [chemical formula 19]

In the general formula (3), R ¹ to R ⁶ each independently represent a deuterium atom or a substituent not containing a cyano group. R ¹ to R ⁶ are not bonded to other R ¹ to R ⁶ to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1, n3, and n5 each independently represent any integer of 0-4, n2 and n6 each independently represent any integer of 0-3, and n4 represents any integer of 0-2. However, n1+n3+n4+n5 is 1 or more. One or both of R ¹ and R ³ to R ⁵ represent an alkyl group which may be deuterated or a phenyl group which may be substituted with a deuterium atom. X represents an oxygen atom or a sulfur atom. Regarding the definitions and descriptions of R ¹ to R ⁶ and n1 to n6 in general formula (3), you can refer to the definitions and descriptions of R ¹ to R ⁶ and n1 to n6 in general formula (2A) and general formula (2B). In the general formula (3), n1+n3+n4+n5 is 1 or more, and one or two of R ¹ and R ³ to R ⁵ represent an alkyl group that may be deuterated or a phenyl group that may be substituted by a deuterium atom (hereinafter referred to as "phenyl A") is different. In the general formula (3), three or more of R ¹ and R ³ to R ⁵ are not phenyl A. In one aspect of the invention, only one R ¹ is phenyl A. In one aspect of the invention, only one ^R3 is phenyl A. In one aspect of the invention, only one ^R4 is phenyl A. In one aspect of the invention, only one R ⁵ is phenyl A. In one aspect of the invention, only one ^R3 and one ^R4 is phenyl A. In one aspect of the invention, only one ^R3 and one ^R5 is phenyl A. In one aspect of the invention, only one ^R4 and one ^R5 is phenyl A. In the present invention, only two R ³ , only two R ⁴ or only two R ⁵ may be phenyl A. Furthermore, when n3+n4+n5 is 0, it is preferable that ^R1 is not an unsubstituted phenyl group. In one aspect of the present invention, at least one of R ³ to R ⁵ is phenyl A, and n3+n4+n5 is 1 or more. At least one of the phenyl groups A of R ³ to R ⁵ is bonded at the meta position (2-position of the carbazole ring) when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of the carbazole. In a preferred aspect of the present invention, when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole, at least one of the phenyl groups A of R ³ to R ⁵ is in the para position (carbazole ring 3 bits) bonded. In one aspect of the present invention, when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole, the phenyl groups A of R ³ to R ⁵ are bonded only at the meta position (2-position of the carbazole ring). . In a preferred aspect of the present invention, when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole, the phenyl A of R ³ to R ⁵ is only in the para position (the 3 position of the carbazole ring ) bond. In one aspect of the present invention, when viewed from the bonding position of the oxygen atom constituting the ring skeleton of the benzofluorine structure or the sulfur atom constituting the ring skeleton of the benzothieno structure, the phenyl groups of R ³ to R ⁵ A bonds only in the para position. In a preferred aspect of the present invention, when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole, one of the phenyl groups A of R ³ to R ⁵ is bonded at the para position, When observing the bonding position of the oxygen atom of the ring skeleton of the fluorine structure or the sulfur atom constituting the ring skeleton of the benzothieno structure, one of the phenyl groups A of R ³ to R ⁵ is bonded at the para position. In one aspect of the present invention, the phenyl group A is a phenyl group that may be substituted with an alkyl group that may be deuterated. In a preferred aspect of the present invention, the phenyl group A is a phenyl group that may be substituted with a deuterium atom. In a particularly preferred aspect of the present invention, phenyl A is unsubstituted phenyl. n3+n4+n5 in general formula (3) is any integer from 1 to 10, preferably any integer from 1 to 8, more preferably any integer from 1 to 6, and any integer from 1 to 4 Any integer of is further preferred. In a preferred aspect of the present invention, n3+n4+n5 is 1. In a preferred aspect of the present invention, n3+n4+n5 is 2.

For example, when the organic layer containing the compound represented by the general formula (1) is intended to be used as a film by vapor deposition, the molecular weight of the compound represented by the general formula (1) is preferably 1500 or less. 1200 or less is more preferable, 1000 or less is still more preferable, and 900 or less is still more preferable. The lower limit of the molecular weight is the molecular weight of the smallest compound of the compound group represented by the general formula (1). The compound represented by the general formula (1) can be formed into a film by a coating method regardless of the molecular weight. As long as the coating method is used, even a compound with a relatively large molecular weight can be formed into a film. The compound represented by the general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify to increase the purity.

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

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. Furthermore, D in P6 to P14 represents a deuterium atom. [chemical formula 20]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 21]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 22]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 23]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 24]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 25]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 26]

As the compound represented by the general formula (1), the following compounds can also be used. [chemical formula 27]

[chemical formula 28]

Compounds 1a to 47n in which all the hydrogen atoms are replaced by deuterium atoms are exemplified here as compounds 1a(D) to 47n(D). Compounds 1a (Ph) to 21d (Ph) in which only hydrogen atoms bonded to the phenyl groups of Compounds 1a to 21d are substituted with deuterium atoms are exemplified here. In the present invention, compounds 1a to 21d are examples of compounds more preferable than compounds 22 and 23. In one aspect of the present invention, it is selected from the compound na (n is an integer of 1 to 21, and the compound na described here represents the group consisting of compounds 1a, 2a, 3a···21a). In a preferred aspect of the present invention, it is selected from compound nb (n represents an integer of 1-21). In one aspect of the present invention, it is selected from compound nc (n represents an integer of 1 to 21). In one aspect of the present invention, it is selected from compound nd (n represents an integer of 1-21). In one aspect of the present invention, compounds 1a to 5d are selected. In one aspect of the present invention, compounds 7a to 9d are selected. In one aspect of the present invention, compounds 10a to 12d are selected. In one aspect of the present invention, compounds 13a to 15d are selected. In one aspect of the present invention, compounds 16a-18d are selected. In one aspect of the present invention, compounds 19a-21d are selected. Moreover, in the present invention, compounds 24a to 47n are mentioned as compounds more preferable than compound 23, and compounds 24a to 27n are mentioned as further preferable compounds. In one aspect of the present invention, compounds 24a-24n are selected. In one aspect of the present invention, compounds 25a-25n are selected. In one aspect of the present invention, compounds 26a-26n are selected. In one aspect of the present invention, compounds 27a-27n are selected. In one aspect of the invention, compounds 24a, 25a, 26a, 27a, 24f, 25f, 26f, 27f are selected.

In a preferred aspect of the present invention, the compound represented by the general formula (1) is selected from the following compound groups. [chemical formula 29]

In this specification, the compound represented by the following general formula (A) is also disclosed about the compound useful as an electron barrier material or a host material. [chemical formula 30]

In the general formula (A), X ¹ represents an oxygen atom or a sulfur atom. X ² represents an oxygen atom, a sulfur atom, N(R ⁷ ) or C(R ⁸ )(R ⁹ ). R ¹ to R ⁶ each independently represent one atom or group selected from the group including a deuterium atom, an alkyl group and an aryl group, or a group obtained by combining two or more. At least one R ¹ is an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group obtained by combining two or more. R ¹ to R ⁶ are not bonded to other R ¹ to R ⁶ to form a ring structure, but adjacent R ³ may bond to each other to form a benzofluoro skeleton or a benzothieno skeleton. n1 represents an integer of 1-4, n3, n5, and n6 each independently represent any integer of 0-4, n2 represents any integer of 0-3, and n4 represents any integer of 0-2. Furthermore, in the general formula (A), the (R ⁵ ) _n5 -bonded benzene ring and the (R ⁴ ) _n4 -bonded benzene ring are linked by a single bond and a linker via X ² , but The left and right positional relationship of these two keys can also be reversed. That is, in the above general ^formula (A), a single bond is shown on the left side and a linking group via X2 is shown on the right side, but a single bond is shown on the right side and a linking group via ^X2 is shown on the left side It is also included in the general formula (A).

In a preferred aspect of the present invention, ^X1 and ^X2 are the same. In one aspect of the invention, ^X1 and ^X2 are different. In a preferred aspect of the present invention, ^{both X1} and ^X2 are oxygen atoms. In one aspect of the present invention, ^{both X1} and ^X2 are sulfur atoms. In one aspect of the present invention, X ¹ is an oxygen atom, and X ² is a sulfur atom. In one aspect of the present invention, X ¹ is a sulfur atom, and X ² is an oxygen atom. In one aspect of the present invention, X ¹ is an oxygen atom, and X ² is N(R ⁷ ). In one aspect of the present invention, X ¹ is an oxygen atom, and X ² is C(R ⁸ )(R ⁹ ). In a preferred aspect of the present invention, X ¹ is an oxygen atom. In a preferred aspect of the present invention, X ² is an oxygen atom or a sulfur atom, more preferably an oxygen atom.

R ¹ to R ⁶ are each independently an atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group obtained by combining two or more, preferably a deuterium atom, which can be deuterium An atom-substituted alkyl group or an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group obtained by combining two or more. In a preferred aspect of the present invention, R ¹ to R ⁶ are each independently a deuterium atom, or can be formed by an atom or group selected from the group including a deuterium atom and an aryl group, or a combination of two or more The obtained radical substituted aryl. The carbon number of the alkyl group in the description of general formula (1) can be selected within the range of 1-40 normally, Preferably it is 1-15, More preferably, it is 1-6, For example, 1-3. The carbon number of an aryl group can be selected within the range of 6-30 normally, Preferably it is 6-18, More preferably, it is 6-14, For example, 6-10. In one aspect of the present invention, R ³ are bonded to each other to form a benzofluorine skeleton. In one aspect of the present invention, R ³ are bonded to each other to form a benzothieno skeleton. The benzofluorine skeleton or the benzothieno skeleton may be substituted with one atom or group selected from the group including a deuterium atom, an alkyl group, and an aryl group, or a group obtained by combining two or more. In one aspect of the present invention, R ³ are not bonded to each other to form a ring structure.

At least one R ¹ is an aryl group that may be substituted by an atom or group selected from the group including a deuterium atom, an alkyl group, and an aryl group, or a group obtained by combining two or more, and more preferably may be substituted by a group selected from A phenyl group substituted by one atom or group in the group including a deuterium atom, an alkyl group and an aryl group, or a group obtained by combining two or more groups, further preferably, it can be selected from the group including a deuterium atom and a phenyl group A phenyl group substituted by one atom or group in the group or a combination of two or more groups. In one aspect of the present invention, the ^R is an unsubstituted aryl group or an aryl group in which all hydrogen atoms are substituted by deuterium atoms, preferably an unsubstituted phenyl group or an aryl group in which all hydrogen atoms are substituted by deuterium atoms phenyl. In a preferred aspect of the present invention, only one ^R is a group that can be obtained through one atom or group selected from the group including deuterium atom, alkyl group and aryl group, or a combination of two or more Substituted aryl. In one aspect of the present invention, two R ¹ are aryl that may be substituted by one atom or group selected from the group consisting of deuterium atom, alkyl and aryl, or a group obtained by combining two or more base. Specific examples of the group that can be used as at least one R ¹ include the aforementioned P1 to P14. Among them, R ¹ that can be used in the present invention is not limitedly interpreted by these specific examples. Furthermore, in the general formula (A), the group [ _{the 5-} ring group on the right side of the general formula (A)] that is bonded to the benzene ring bonded to (R ⁵ ) n5 from the right side is benzofluoro[3 ,2-a] carbazolyl, R ¹ is not unsubstituted phenyl.

Among the compounds represented by the general formula (A), for example, a compound represented by the following general formula (A1) can be preferably used. [chemical formula 31]

For the definition and description of X ¹ , X ² , R ¹ to R ⁶ , and n1 to n6 in the general formula (A1), reference can be made to the corresponding description of the above general formula (A).

[Organic semiconductor device] The compound represented by the general formula (1) can be suitably used in organic semiconductor devices. For example, CMOS (Complementary Metal Oxide Semiconductor) etc. using the compound represented by the general formula (1) can be produced. In a certain embodiment of the present disclosure, organic light-emitting devices such as organic electroluminescent devices and solid-state imaging devices (for example, CMOS image sensors) can be produced using the compound represented by the general formula (1). Among them, the compound represented by the general formula (1) of the present invention can be used in organic light-emitting devices such as organic electroluminescent devices (organic EL devices). In particular, the compound represented by the general formula (1) of the present invention can be effectively used as an electron barrier material of an organic light-emitting device. In particular, the device life can be extended by using the compound represented by the general formula (1) of the present invention for the electron barrier layer.

The organic electroluminescent element 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 preferably has one or more organic layers (especially electron barrier layers) in addition to the light-emitting layer. Examples of the organic layer constituting the organic electroluminescent element 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, an exciton barrier layer, and a substrate for a light emitting layer. layers etc. 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. In the following, each member and each layer of the organic electroluminescence element will be described. Furthermore, the description of the substrate and the light-emitting layer also corresponds to the substrate and the light-emitting layer of the organic photoluminescence element.

(Electron barrier layer) In a preferred aspect of the present invention, the compound represented by the general formula (1) is used in the electron barrier layer of the organic electroluminescent device. The electron barrier layer may contain only the compound represented by General formula (1), or may contain a compound other than the compound represented by General formula (1). The concentration of the compound represented by the general formula (1) in the electron barrier layer is preferably 50% by weight or more, more preferably 90% by weight or more, for example, 99% by weight or more, or 99.9% by weight or more . The thickness of the electron barrier layer is preferably 1 nm or more, more preferably 3 nm or more, and can be, for example, 5 nm or more or, for example, 10 nm or more. The thickness of the electron barrier layer is preferably less than 30 nm, more preferably less than 20 nm, and can be, for example, 15 nm or less. The thickness of the electron barrier layer is preferably smaller than that of the light emitting layer. The thickness of the electron barrier layer is preferably 1/2 or less of the thickness of the light emitting layer, more preferably 1/3 or less, for example, can be set to 1/4 or less. Moreover, 1/20 or more is preferable, For example, it can be 1/10 or more or, for example, 1/6 or more. It is preferable that the electron barrier layer containing the compound represented by general formula (1) is provided between a light emitting layer and an anode. In one aspect of the present invention, the light emitting layer and the electron barrier layer are laminated in direct contact. One aspect of the present invention includes a laminated structure in which an electron barrier layer containing a compound represented by general formula (1), a base layer, and a light emitting layer are sequentially laminated from the anode side. The electron barrier layer and the base layer are laminated in direct contact, and the base layer and the light-emitting layer are laminated in direct contact, but the electron barrier layer and the light-emitting layer are not in contact.

(basal layer) The base layer is formed for the purpose of improving the orientation of the light-emitting layer, etc., and is a layer containing a hole-transporting material. In one aspect of the present invention, the base layer contains a compound having a common partial structure with the compound contained in the light emitting layer. The common partial structure mentioned here means that the partial structure composed of 12 or more atoms other than hydrogen atom and deuterium atom is common, and the partial structure composed of 16 or more atoms other than hydrogen atom and deuterium atom is preferably common , for example, a partial structure composed of 20 or more atoms other than hydrogen atoms and deuterium atoms may be common. In one aspect of the present invention, the base layer contains the same compound as that contained in the light emitting layer. In one aspect of the present invention, the base layer only contains the same compounds as those contained in the light-emitting layer. In one aspect of the present invention, the base layer contains the same compound as the host material contained in the light emitting layer. The thickness of the base layer is preferably at least 1 nm, more preferably at least 3 nm, and can be, for example, at least 5 nm. The thickness of the adjacent layer is preferably less than 30 nm, more preferably less than 20 nm, and can be set to, for example, 10 nm or less or 7 nm or less. The thickness of the base layer is preferably smaller than that of the light emitting layer. The thickness of the base layer is preferably 1/2 or less of the thickness of the light emitting layer, more preferably 1/3 or less, for example, can be set to 1/4 or less. Moreover, 1/20 or more is preferable, For example, it can be set as 1/10 or more. The thickness of the base layer is preferably smaller than that of the electron barrier layer. The thickness of the base layer can be, for example, 3/4 or less, for example, 2/3 or less, or, for example, 1/2 or less of the thickness of the electron barrier layer. Moreover, 1/20 or more is preferable, For example, it can be set as 1/10 or more or, for example, 1/4 or more.

(luminous layer) The light-emitting layer is a layer that emits light after generating excitons by rebonding holes and electrons injected from the anode and the cathode, respectively. The light emitting layer contains at least a light emitting material. In order for an organic electroluminescent device to exhibit high luminous efficiency, it is important to confine the singlet excitons and triplet excitons of the luminescent material to the luminescent material. Therefore, it is preferable to use a host material in addition to the light-emitting material in the light-emitting layer. As a host material, an organic compound having a higher value of excited singlet energy than the light-emitting material of the present invention can be used, and it is preferable to use an organic compound with higher values of excited singlet energy and excited triplet energy than the light-emitting material. By using a host material, the singlet excitons and triplet excitons generated in the light emitting material can be confined to the molecules of the light emitting material, and the light emitting efficiency can be fully exhibited. However, there are cases where high luminous efficiency can be obtained even if singlet excitons and triplet excitons cannot be sufficiently restricted, so as long as it is a host material that can realize high luminous efficiency, it can be used in the present invention without particular limitation. . In the organic electroluminescent device of the present invention, the largest amount of light emitted from the device is the light emitted from the light-emitting material contained in the light-emitting layer. The luminescence includes fluorescent luminescence, and may also include delayed fluorescence. However, part or part of the emitted light may be emitted from the host material. In the case of using a host material, the concentration of the luminescent material in the luminescent layer is preferably 0.1% by weight or more, more preferably 1% by weight or more, and preferably 50% by weight or less, more preferably 20% by weight or less, It is further preferably 10% by weight or less.

In the light emitting layer, an auxiliary dopant can be used. In this case, the light-emitting layer is composed of a host material, an auxiliary dopant, and a light-emitting material. Wherein, the lowest excited singlet energy level is higher than the auxiliary dopant as the host material, and the lowest excited singlet energy level is lower than the auxiliary dopant as the light emitting material. In the present invention, it is particularly preferred to use a delayed fluorescent material as the auxiliary dopant. Delayed fluorescence is fluorescence that is emitted when the excited singlet state returns to the ground state after an inverse intersystem transition from the excited triplet state to the excited singlet state occurs in a compound that has become an excited state, and is the ratio Fluorescence from the excited singlet state that transitions directly from the ground state (instant fluorescence) is more delayed than the observed fluorescence. In the present invention, when measuring the transient decay curve of luminescence at 300K for a thin film containing the target compound, a luminescence component with a long luminescence lifetime (delayed fluorescence) was observed in addition to a luminescence component with a short luminescence lifetime (instant fluorescence). In the case of light), the target compound is set as a retarded fluorescent material. The delayed fluorescent material is preferably a thermally active delayed fluorescent material capable of generating inverse intersystem crossing by absorbing thermal energy. It can be confirmed that it is a thermally active delayed fluorescent material by the fact that the luminescence lifetime obtained by measuring the transient attenuation curve of luminescence becomes longer depending on the measurement temperature. By using a delayed fluorescent material as an auxiliary dopant, in the auxiliary dopant, the energy of the excited singlet state generated by direct transition from the ground state and the energy of the excited singlet state based on the inverse inter-system crossing are efficiently transferred to the luminescent material, thereby effectively assisting the luminescence of the luminescent material. When the light-emitting layer is composed of a host material, an auxiliary dopant, and a light-emitting material, the concentration of the auxiliary dopant in the light-emitting layer is preferably smaller than that of the host material. Specifically, when the total weight of the content of the host material, the content of the auxiliary dopant, and the content of the luminescent material is taken as 100% by weight, the content of the host material is preferably 15% by weight or more and 99.9% by weight or less. The content of the auxiliary dopant is preferably not less than 5.0% by weight and not more than 50% by weight, and the content of the luminescent material is preferably not less than 0.5% by weight and not more than 5.0% by weight. In one aspect of the present invention, the light-emitting layer does not contain inorganic compounds. Also, in one aspect of the present invention, the light-emitting layer does not contain metal atoms. In one aspect of the invention, at 300K, no phosphorescence was observed from the light-emitting layer.

The host material used in the light-emitting layer has hole-transporting ability and electron-transporting ability to prevent long-wavelength emission, and an organic compound with a high glass transition temperature is preferable. In one aspect of the present invention, as the host material, a compound containing a carbazole structure can be preferably selected. In a preferred aspect of the present invention, as a host material, two or more structures selected from the group consisting of a carbazole structure, a dibenzofuran structure and a dibenzothiophene structure (for example, including two structures) or compounds with three structures. In a preferred aspect of the present invention, a compound containing a 1,3-phenylene structure can be selected as the host material. In a preferred aspect of the present invention, a compound containing a biphenylene structure can be selected as the host material. In a preferred aspect of the present invention, as the host material, a compound containing 5 to 8 benzene rings in the molecule can be selected, for example, five compounds, six compounds, or seven compounds can be selected. compound. In the following, preferred compounds that can be used as host materials are listed, but the host materials that can be used in the present invention are not limitedly interpreted by the following specific examples. [chemical formula 32]

In the light emitting layer, a delayed fluorescent material can be used as a light emitting material or an auxiliary dopant. In addition, different retarded fluorescent materials can be used as the light emitting material and the auxiliary dopant. When the luminescence lifetime is measured with a fluorescence lifetime measurement system (Hamamatsu Photonics KK's streak camera system, etc.), fluorescence with a luminescence lifetime of 100 ns (nanosecond) or more is usually observed from delayed fluorescent materials. 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 thermally activated delayed fluorescent material can absorb the heat emitted by the device and relatively easily transition from the excited triplet state to the excited singlet state, and the excited triplet state energy can be efficiently contributed 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.

Preferably, the delayed fluorescent material 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, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur 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. Typical delayed fluorescent materials include compounds having a structure in which a benzene ring is bonded to 1 to 2 acceptor groups and at least one donor group. As the acceptor group, preferably, a cyano group, a group including a heteroaryl ring including a nitrogen atom as an atom constituting a ring skeleton such as a trioxane ring can be exemplified. As the donor group, for example, a substituted or unsubstituted carbazol-9-yl group can be preferably exemplified. For example, a compound in which three or more substituted or unsubstituted carbazol-9-yl groups are bonded to the aforementioned benzene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted Each 5-membered ring part of a benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted silane indene ring and a carbazol-9-yl Compounds in which at least one of the two benzene rings is condensed, etc.

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34]

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35]

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 33]

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 the 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 mentioned here are not cyano groups, the following general formula (5 ), a group represented by the following general formula (6)). [chemical formula 34]

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 35]

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 each independently selected from the group consisting of alkyl (for example, with 1 to 40 carbons), aryl (for example, with 6 to 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), and as substituents for 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 36]

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, naridine 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 can 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 37]

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 38]

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.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E1) can also be mentioned. [chemical formula 39]

In the general formula (E1), R ¹ , R ³ to R ¹⁶ each independently represent a hydrogen atom, a deuterium atom or a substituent. ^R2 represents an acceptor group or ^R1 and ^R2 are bonded to each other to form an acceptor group or ^R2 and ^R3 are bonded to each other to form an acceptor group. 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 ⁹ and R ¹⁰ , R ¹⁰ and R 11 , R ¹¹ and R ¹² , ^{R 12} and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ may be bonded to each other to form a ring structure. X ¹ represents O or NR, and R represents a substituent. At least one of X ³ and X ⁴ among X ² to X ⁴ may be O or NR, and the rest may be O or NR, or may not be connected. When not connected, both ends independently represent a hydrogen atom, a deuterium atom or a substituent. CR ¹ , CR ³ , CR 4 , CR ⁵ , CR ^{6 , CR 7 ,} CR ⁸ , CR ⁹ , CR ¹⁰ , CR ¹¹ , CR ¹² , CR ¹³ , CR ¹⁴ , ^{CR 15 ,} CR in general formula (1) ¹⁶ can be replaced by N.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E2) can also be mentioned. [chemical formula 40]

In the general formula (E2), R ¹ and R ² independently represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R ³ ~R ¹⁶ each independently represent a hydrogen atom, a deuterium atom or a substituent. R ¹ and R ³ , R 3 and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and ^{R 7} , R ⁷ and R ⁸ , R ⁸ and R ⁹ , R ⁹ and R ² , R ² and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R 13 , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ¹⁵ and R ¹⁶ , ^{R 16 and} R ¹ may be bonded to each other and form a ring structure. CR ³ , CR ⁴ , CR ⁵ , CR 6 , CR ⁷ , CR ⁸ , CR ⁹ , CR ¹⁰ , CR ¹¹ , CR ¹² , ^{CR 13 , CR 14 , CR 15 , CR 16 in general formula (} 1) can be passed through N substituted.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E3) can also be mentioned. [chemical formula 41]

In the general formula (E3), Z ¹ and Z ² each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R ¹ to R ⁹ each independently represent a hydrogen atom, deuterium atom or 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 ⁷ and R ⁸ , R ⁸ and R ⁹ may be bonded to each other to form a ring structure . Among them, the ring formed by Z ¹ , Z ² , R ¹ and R ² bonded to each other, the ring formed by R ² and R ³ bonded to each other, the ring formed by R ⁴ and R ⁵ bonded to each other, and the ring formed by R ⁵ and At least one of the rings formed by bonding ^R to each other is the furan ring of substituted or unsubstituted benzofuran, the thiophene ring of substituted or unsubstituted benzothiophene, the substituted or unsubstituted indene ring The pyrrole ring of indole, and at least one of R ¹ to R ⁹ is a substituted or unsubstituted aryl or acceptor group or at least one of Z ¹ and Z ² has an aryl or acceptor group as ring of substituents. Of the carbon atoms constituting the benzene ring skeleton of the benzofuran ring, the benzothiophene ring, and the indole ring, substitutable carbon atoms may be substituted with nitrogen atoms. CR ¹ , CR ² , CR ³ , CR ⁴ , CR ⁵ , CR ⁶ , CR ⁷ , CR ⁸ , and CR ⁹ in the general formula (1) may be substituted with N.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E4) can also be mentioned. [chemical formula 42]

In the general formula (E4), Z ¹ represents a furan ring formed by condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by condensation of substituted or unsubstituted benzene rings, or a substituted or unsubstituted An N-substituted pyrrole ring formed by condensation of benzene rings, ^Z2 and ^Z3 independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaryl ring, ^R1 represents a hydrogen atom or a deuterium atom Or a substituent, R ² and R ³ each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z ¹ and R ¹ , R ² and Z ² , Z ² and Z ³ , and Z ³ and R ³ may be bonded to each other to form a ring structure. Among them, at least one group among R ² and Z ² , Z ² and Z ³ , and Z ³ and R ³ is bonded to each other to form a ring structure.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E5) can also be mentioned. [chemical formula 43]

In the general formula (E5), R ¹ and R ² independently represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, Z ¹ and Z ² each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaryl ring, and R ³ to R ⁹ each independently represent a hydrogen atom, a deuterium atom or a substituent. Wherein, at least one of R ¹ , R ² , Z ¹ and Z ² contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indene Indole ring. R ¹ and Z ¹ , Z ¹ and R ^{3 ,} R 3 and R ⁴ , R ⁴ and R ⁵ , R ⁵ and Z ² , Z ² and R 2 , R ² and R ⁶ , R ⁶ and R ⁷ , ^{R 7} and R ⁸ , R ⁸ and R ⁹ , R ⁹ and R ¹ may be bonded to each other to form a ring structure. Of the carbon atoms constituting the benzene ring skeleton of the benzofuran ring, the benzothiophene ring, and the indole ring, substitutable carbon atoms may be substituted with nitrogen atoms. CR ³ , CR ⁴ , CR ⁵ , CR ⁶ , CR ⁷ , CR ⁸ , and CR ⁹ in the general formula (1) may be replaced by N.

As further preferable delayed fluorescent materials, compounds represented by the following general formula (E6) can also be mentioned. [chemical formula 44]

In the general formula (E6), R ²⁰¹ to R ²²¹ independently represent a hydrogen atom, a deuterium atom or a substituent, preferably represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or an alkyl and aryl group are bonded together. into the group. R ²⁰¹ and R ²⁰² , R ²⁰² and R ²⁰³ , R ²⁰³ and R ²⁰⁴ , R ²⁰⁵ and R ²⁰⁶ , R ²⁰⁶ and R ²⁰⁷ , R ²⁰⁷ and R ^{208 , R 214 and} R 215 , R ²¹⁵ and R ²¹⁶ , ^{R 216} and at least one group of R ²¹⁷ , R ²¹⁸ and R ²¹⁹ , R ²¹⁹ and R ²²⁰ , and R ²²⁰ and R ²²¹ are bonded to each other to form a benzofluoro structure or a benzothieno structure. Preferably, one or two groups of R ²⁰¹ and R ²⁰² , R ²⁰² and R ²⁰³ , R ²⁰³ and R ²⁰⁴ , R ²⁰⁵ and R ²⁰⁶ , R ²⁰⁶ and R ²⁰⁷ , R ²⁰⁷ and R ²⁰⁸ are combined with R ²¹⁴ and One or two groups of R ²¹⁵ , R ²¹⁵ and R ²¹⁶ , R ²¹⁶ and R ²¹⁷ , R ²¹⁸ and R ²¹⁹ , R ²¹⁹ and R ²²⁰ , R ²²⁰ and R ²²¹ are bonded to each other to form a benzofluorine structure or a benzene And thieno structure. It is further preferred that R ²⁰³ and R ²⁰⁴ are bonded to each other to form a benzofluorine structure or a benzothieno structure, and it is further preferred that R ²⁰³ and R ²⁰⁴ , R ²¹⁶ and R ²¹⁷ are bonded to each other to form a benzofluorine structure Or benzothieno structure. Particularly preferably, R ²⁰³ and R ²⁰⁴ , R ²¹⁶ and R ²¹⁷ are bonded to each other to form a benzofluorine structure or a benzothieno structure, and R ²⁰⁶ and R ²¹⁹ are substituted or unsubstituted aryl groups (preferably substituted or unsubstituted phenyl, more preferably unsubstituted phenyl). The general formula (E6) includes structures in which R ²⁰¹ to R ²⁰⁸ and R ²¹⁴ to R ²²¹ may each independently be a deuterium atom instead of a hydrogen atom ( ¹ H). That is, when R ²⁰¹ to R ²⁰⁸ and R ²¹⁴ to R ²²¹ contain one atom, the atom includes a structure limited to a deuterium atom.

Furthermore, Japanese Patent No. 2021-103698, Japanese Patent No. 2021-103699, Japanese Patent No. 2021-103700, Japanese Patent No. 2021-081332, Japanese Patent No. 2021-103701, Japanese Patent No. 2021-151805, Japanese Patent No. 2021- The compound represented by the general formula (1) described in each specification of No. 188860 is used as a delayed fluorescent material. The description of these general formula (1) and a specific compound are taken in here as a part of this specification.

Preferred compounds that can be used as delayed fluorescent materials are listed below. In the following structural formulas of exemplary compounds, t-Bu represents a tertiary butyl group. [chemical formula 45]

Compounds in which all the hydrogen atoms of the above-mentioned compounds T1 to T151 are substituted with deuterium atoms are exemplified here as T1(D) to T151(D). Compounds in which all hydrogen atoms in the substituted or unsubstituted carbazol-9-yl (including ring-condensed ones) present in the above compounds T1-T151 are replaced with deuterium atoms are T1(d)-T151 The form of (d) is illustrated here.

In addition to the above, known retarded fluorescent materials 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 Japanese Patent Application Publication No. 119664, paragraphs 0012-0025 of Japanese Patent Application Publication No. 2017-222623, paragraphs 0010-0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012-0043 of Japanese Patent Application Publication No. 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.

In the light-emitting layer, in the case of using a retarded fluorescent material as the auxiliary dopant, a compound having the lowest excited singlet energy smaller than the auxiliary dopant is used as the light-emitting material. Examples of light-emitting materials used in combination with auxiliary dopants include compounds having multiple resonance effects of boron atoms and nitrogen atoms, and compounds containing condensed aromatic ring structures such as anthracene, pyrene, and perylene. In addition, the retarded fluorescent materials exemplified so far can also be used. In a preferred aspect of the present invention, a compound represented by the following general formula (F1) is used as a light-emitting material used in combination with an auxiliary dopant. General formula (F1) [Chemical formula 46]

In the above general formula (F1), Ar ¹ to Ar ³ are each independently an aromatic ring or a heteroaromatic ring, at least one hydrogen atom in these rings may be substituted, and the rings may be condensed. When a hydrogen atom is substituted, it is preferably substituted with a deuterium atom, a group selected from the group consisting of aryl, heteroaryl and alkyl, or a combination of two or more. Also, in the case of ring condensation, condensation of a benzene ring or a heteroaromatic ring (for example, furan ring, thiophene ring, pyrrole ring, etc.) is preferable. R ^a and R ^a' each independently represent a substituent, preferably a deuterium atom, one group selected from the group consisting of aryl, heteroaryl and alkyl, or a group obtained by combining two or more. R ^a and Ar ¹ , Ar ¹ and Ar ² , Ar ² and R ^a′ , R ^a′ and Ar ³ , and Ar ³ and R ^a may be bonded to each other to form a ring structure.

The compound represented by general formula (F1) preferably contains at least one carbazole structure. For example, a benzene ring constituting the carbazole structure can be represented by Ar ¹ , a benzene ring constituting the carbazole structure can be represented by Ar ² , and a benzene ring constituting the carbazole structure can be represented by Ar ³ ring. Also, the carbazolyl group may be bonded to any one or more of Ar ¹ to Ar ³ . For example, a substituted or unsubstituted carbazol-9-yl group may be bonded to the ring represented by Ar ³ .

Condensed aromatic ring structures such as anthracene, pyrene, and perylene may be bonded to Ar ¹ to Ar ³ . Also, the rings represented by Ar ¹ to Ar ³ may be one ring constituting a condensed aromatic ring structure. Furthermore, at least one of R ^a and R ^a' may be a group having a condensed aromatic ring structure.

A plurality of skeletons represented by the general formula (F1) may exist in the compound. For example, it may have a structure in which the skeletons represented by the general formula (F1) are bonded to each other via a single bond or a linking group. In addition, to the skeleton represented by the general formula (F1), a structure showing a multiple resonance effect in which benzene rings are connected to each other via a boron atom, a nitrogen atom, an oxygen atom, and a sulfur atom may be added.

In a preferred aspect of the present invention, the use contains BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene: 4,4-difluoro-4-bora-3a,4a - Compounds with the structure of bis-aza-s-indene are used as luminescent materials in combination with auxiliary dopants. For example, a compound represented by the following general formula (F2) is used. General formula (F2) [Chemical formula 47]

在通式（F3）中，R ¹¹～R ¹⁵分別獨立地表示氫原子、氘原子或取代基，*表示鍵結位置。 通式（F3）所表示之基團可以為通式（F2）的R ¹～R ⁷中的一個，亦可以為兩個，亦可以為三個。又，可以設為至少四個，例如能夠設為四個或五個。在本發明的較佳的一態樣中，R ¹～R ⁷中的一個為通式（F3）所表示之基團。在本發明的較佳的一態樣中，至少R ¹、R ³、R ⁵、R ⁷為通式（F3）所表示之基團。在本發明的較佳的一態樣中，僅R ¹、R ³、R ⁴、R ⁵、R ⁷為通式（F3）所表示之基團。在本發明的較佳的一態樣中，R ¹、R ³、R ⁴、R ⁵、R ⁷為通式（F3）所表示之基團，R ²及R ⁴為氫原子、氘原子、未經取代的烷基（例如，碳數1～10）或未經取代的芳基（例如，碳數6～14）。在本發明的一態樣中，R ¹～R ⁷均為通式（F3）所表示之基團。 在本發明的較佳的一態樣中，R ¹和R ⁷相同。在本發明的較佳的一態樣中，R ³和R ⁵相同。在本發明的較佳的一態樣中，R ²和R ⁶相同。在本發明的較佳的一態樣中，R ¹和R ⁷相同，R ³和R ⁵相同，進而R ¹和R ³彼此不同。在本發明的較佳的一態樣中，R ¹、R ³、R ⁵、R ⁷相同。在本發明的較佳的一態樣中，R ¹和R ⁴和R ⁷相同，R ³和R ⁵不同。在本發明的較佳的一態樣中，R ³和R ⁴和R ⁵相同，R ¹和R ⁷不同。在本發明的較佳的一態樣中，R ¹、R ³、R ⁵、R ⁷均與R ⁴不同。 In the general formula (F2), R ¹ to R ⁷ are each independently a hydrogen atom, a deuterium atom or a substituent. It is preferable that at least one of R ¹ to R ⁷ is a group represented by the following general formula (F3). General formula (F3) [Chemical formula 48]

In the general formula (F3), R ¹¹ to R ¹⁵ each independently represent a hydrogen atom, a deuterium atom or a substituent, and * represents a bonding position. The group represented by the general formula (F3) may be one, two or three of R ¹ to R ⁷ of the general formula (F2). Also, at least four can be used, for example, four or five can be used. In a preferred aspect of the present invention, one of R ¹ to R ⁷ is a group represented by general formula (F3). In a preferred aspect of the present invention, at least R ¹ , R ³ , R ⁵ , and R ⁷ are groups represented by general formula (F3). In a preferred aspect of the present invention, only R ¹ , R ³ , R ⁴ , R ⁵ , and R ⁷ are groups represented by general formula (F3). In a preferred aspect of the present invention, R ¹ , R ³ , R ⁴ , R ⁵ , and R ⁷ are groups represented by general formula (F3), R ² and R ⁴ are hydrogen atoms, deuterium atoms, Unsubstituted alkyl group (for example, having 1 to 10 carbon atoms) or unsubstituted aryl group (for example, having 6 to 14 carbon atoms). In one aspect of the present invention, R ¹ to R ⁷ are all groups represented by general formula (F3). In a preferred aspect of the present invention, R ¹ and R ⁷ are the same. In a preferred aspect of the present invention, ^R3 and ^R5 are the same. In a preferred aspect of the present invention, R ² and R ⁶ are the same. In a preferred aspect of the present invention, R ¹ and R ⁷ are the same, R ³ and R ⁵ are the same, and R ¹ and R ³ are different from each other. In a preferred aspect of the present invention, R ¹ , R ³ , R ⁵ , and R ⁷ are the same. In a preferred aspect of the present invention, ^R1 , ^R4 and ^R7 are the same, and ^R3 and ^R5 are different. In a preferred aspect of the present invention, ^R3 , ^R4 and ^R5 are the same, and ^R1 and ^R7 are different. In a preferred aspect of the present invention, R ¹ , R ³ , R ⁵ , and R ⁷ are all different from R ⁴ .

The substituents that can be adopted by R ¹¹ to R ¹⁵ of the general formula (F3) are, for example, selected from the following substituent group A, selected from the following substituent group B, selected from the following substituent group C, or Choose from substituent group D described below. In the case of choosing a substituted amino group as a substituent, a disubstituted amino group is preferred, as the two substituents relative to the amino group are independently substituted or unsubstituted aryl, substituted or unsubstituted A substituted heteroaryl group or a substituted or unsubstituted alkyl group is preferred, and a substituted or unsubstituted aryl group (diarylamino group) is particularly preferred. As the substituents that can be adopted by the two aryl groups in the diarylamino group, for example, it can be selected from the following substituent group A, from the following substituent group B, from the following substituent group C, or from Substituent group D described below is selected. The two aryl groups in the diarylamine group can be bonded to each other via a single bond or a linking group. For the linking group described here, reference can be made to the description of the linking group in R ³³ and R ³⁴ . As a specific example of the diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group can be used. Examples of the substituted or unsubstituted carbazol-9-yl include groups in which L ¹¹ of the above general formula (9) is a single bond. In a preferred aspect of the present invention, only R ¹³ of the general formula (F3) is a substituent, and R ¹¹ , R ¹² , R ¹⁴ , and R ¹⁵ are hydrogen atoms. In a preferred aspect of the present invention, only R ¹¹ of the general formula (F3) is a substituent, and R ¹² , R ¹³ , R ¹⁴ , and R ¹⁵ are hydrogen atoms. In a preferred aspect of the present invention, only R ¹¹ and R ¹³ of the general formula (F3) are substituents, and R ¹² , R ¹⁴ , and R ¹⁵ are hydrogen atoms. Among R ¹ to R ⁷ of the general formula (F2), a group in which all of R ¹¹ to R ¹⁵ of the general formula (F3) are hydrogen atoms (that is, a phenyl group) may be included. For example, R ² , R ⁴ , R ⁶ may be phenyl.

In the general formula (F2), R ⁸ and R ⁹ are each independently a hydrogen atom, a deuterium atom, a halogen atom, selected from the group consisting of alkyl (for example, with 1 to 40 carbons), alkoxy (for example, with 1 carbon -40), aryloxy (eg, carbon number 6-30) and cyano group, one or a combination of two or more is preferred. In a preferred embodiment of the present invention, R ⁸ and R ⁹ are the same. In a preferred embodiment of the present invention, R ⁸ and R ⁹ are halogen atoms, particularly preferably fluorine atoms.

In one aspect of ^the present invention, ^substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted The total number of substituted amino groups is preferably three or more, for example, three or four compounds can be used. More preferably, the substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group present in R ¹ to R ⁷ of the general formula (F2) The total number is preferably three or more, for example, three compounds or four compounds can be used. At this time, there may be no alkoxy group, aryloxy group, or amino group in R8 ^{and R9} . Further preferably ^, the substituted ^or unsubstituted alkoxy ^, substituted or ^{unsubstituted aryloxy} , The total number of substituted or unsubstituted amino groups is preferably three or more, for example, three compounds or four compounds can be used. In this case, R ² , R ⁶ , R ⁸ , and R ⁹ may not have an alkoxy group, an aryloxy group, or an amino group. In a preferred aspect of the present invention, there are three or more substituted or unsubstituted alkoxy groups. In a preferred aspect of the present invention, there are four or more substituted or unsubstituted alkoxy groups. In a preferred aspect of the present invention, there is one or more substituted or unsubstituted alkoxy groups and two or more substituted or unsubstituted aryloxy groups. In a preferred aspect of the present invention, there are two or more substituted or unsubstituted alkoxy groups and one or more substituted or unsubstituted amino groups. In a preferred aspect of the present invention, there are substituted or unsubstituted alkoxy groups or substituted or unsubstituted aryloxy groups in R ¹ , R ⁴ , and R ⁷ , respectively. In a preferred aspect of the present invention, there are substituted or unsubstituted alkoxy groups in R ¹ , R ⁴ , and R ⁷ respectively.

In one aspect of the present invention, the total number of substituents having a Hammett's σp value of less than -0.2 present in R ¹ to R ⁹ of the general formula (F2) is three or more. Examples of substituents whose Hammett's σp value is less than -0.2 include methoxy (-0.27), ethoxy (-0.24), n-propoxy (-0.25), isopropoxy (-0.45 ), n-butoxy (-0.32). On the other hand, fluorine atom (0.06), methyl group (-0.17), ethyl group (-0.15), tertiary butyl group (-0.20), n-hexyl group (-0.15), cyclohexyl group (-0.15), etc. are not Hami Special substituents with σp values less than -0.2. In one aspect of the present invention, a compound having three or four substituents having a Hammett's σp value of less than -0.2 present in R ¹ to R ⁹ of the general formula (F2) can be used. a compound. More preferably, the number of substituents whose Hammett's σp value is less than -0.2 present in R ¹ to R ⁷ of the general formula (F2) is preferably three or more, for example, three compounds can be used, or Four compounds can be employed. At this time, there may be no substituents whose Hammett's σp value is less than -0.2 in ^R8 and ^R9 . Further preferably, the number of substituents whose Hammett's σp value is less than -0.2 in R ¹ , R ³ , R ⁴ , R ⁵ , and R ⁷ of the general formula (F2) is preferably three or more, For example, three compounds can be used, or four compounds can be used. In this case, R ² , R ⁶ , R ⁸ , and R ⁹ may not have substituents whose Hammett's σp value is less than -0.2. In a preferred aspect of the present invention, each of R ¹ , R ⁴ , and R ⁷ has a substituent whose Hammett's σp value is less than -0.2.

In the present invention, as a light-emitting material used in combination with an auxiliary dopant, a compound containing a carbazole structure can be selected. Also, as a light-emitting material used in combination with an auxiliary dopant, a compound that does not contain any carbazole structure, dibenzofuran structure, or dibenzothiophene structure can be selected.

In the following, preferred compounds that can be used as a light-emitting material used in combination with an auxiliary dopant are listed. Wherein, the luminescent material that can be used in combination with the auxiliary dopant in the present invention is not limitedly interpreted by the following specific examples. In the following structural formulas of exemplary compounds, t-Bu represents a tertiary butyl group. [chemical formula 49]

Derivatives of the above-mentioned exemplary compounds include compounds in which at least one hydrogen atom is replaced by a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, or a diarylamino group. In addition, the compounds described in paragraphs 0220 to 0239 of WO2015/022974 can also be preferably used as a light-emitting material used in combination with an auxiliary dopant.

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 light-emitting material used in combination with an auxiliary dopant. The compound represented by the general formula (G) can be used as an auxiliary dopant. General formula (G) [Chemical formula 50]

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 . 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 51]

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 52]

^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. Ornadine rings other than line rings and quinoline rings. 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 53]

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 54]

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 the compound which has skeleton (1a), the compound represented by following general formula (1a) can be illustrated. General formula (1a) [Chemical formula 55]

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. As for 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 compound in the middle of the following column 8 can be mentioned as a preferable group. [chemical formula 56]

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 57]

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 58]

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 59]

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 60]

Each hydrogen atom in the skeleton (2a) and (2b) 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 (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 61]

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 62]

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 63]

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 in order.

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 64]

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 65]

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 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. 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 66]

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 67]

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 68]

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 69]

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. Hereinafter, such ring-condensed compounds will be described with reference to specific examples.

Preferable examples include compounds in which a benzene ring to which boron atoms are not directly bonded among 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 70]

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 71]

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 the 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 72]

Another specific example of the compound represented by the general formula (4a) is given below. The compounds of the general formula (4a) that can be used in the present invention are not limitedly interpreted by the following group of specific examples. [chemical formula 73]

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 74]

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 75]

Preferable examples include compounds in which the boron atoms of the two benzene rings constituting the partial carbazole structure present in the general formula (G) are condensed with a benzene ring directly bonded to 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 76]

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 , reference can be made 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 77]

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 78]

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 79]

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 80]

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 81]

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 82]

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 83]

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 84]

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 85]

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 86]

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 87]

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 88]

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 89]

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 90]

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 91]

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 each independently represent the integer of 0-2. 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 92]

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 and the benzene rings are condensed. Examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b). [chemical formula 93]

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 94]

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 95]

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 96]

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 97]

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 98]

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 99]

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 100]

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 101]

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 102]

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 103]

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 a skeleton (10), compounds represented by the following general formula (10) can be exemplified. General formula (10) [Chemical formula 104]

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 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 105]

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 106]

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 107]

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 108]

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 109]

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 110]

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 can be used, and a substituted or unsubstituted dicarbazol-9-yl group in which two phenyl groups are not bonded by a single bond can also 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, and R ¹⁹ is more preferably 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 may be hydrogen atoms or deuterium atoms, for example, at least one of R ³ , R ⁶ , R ¹⁹ , and R ²⁴ may 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 111]

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 record. 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113]

[化學式114]

[化學式115]

[化學式116]

[化學式117]

[表1]

[chemical formula 112]

[chemical formula 113]

[chemical formula 114]

[chemical formula 115]

[chemical formula 116]

[chemical formula 117]

[Table 1]

[chemical formula 118]

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 , R 25 and R 26 are bonded to each} other to form a ring structure description.

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 119]

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 120]

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 121]

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 of 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.

(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 an electrode material such as a metal having a low work function (4 eV or less) (called an electron injection metal), an alloy, a conductive compound, or a combination 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 electroluminescent device 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.

(injection 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 122]

Next, examples of preferable compounds that can be used as electron injection materials are given. [chemical formula 123]

(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 124]

(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 a hole injection or transport property and an electron barrier property. 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 125]

(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 126]

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 127]

Preferred materials that can be used in the organic electroluminescent element are specifically exemplified, but materials that can be used in the present invention are not limitedly interpreted by the exemplified 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. Each organic layer of the organic electroluminescence element can be formed by a wet process. In the wet process, a solution obtained by dissolving a composition including compounds constituting an organic layer is applied on a surface, and a layer is formed after the solvent is removed. 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 capable of dissolving the compounds constituting the organic layer is selected and used. In a certain embodiment, a substituent (for example, an alkyl group) that improves solubility in an organic solvent can be introduced into the compound constituting the organic layer. In a certain embodiment, the organic layer can be formed by a dry process. In a certain embodiment, a vacuum vapor deposition method can be used as a dry step, but it is not limited thereto. In the case of using the vacuum deposition method, the compound constituting the organic layer may be co-deposited from a single deposition source, or may be co-deposited from a single deposition source in which a compound is mixed. In the case of using a single vapor deposition source, a mixed powder mixed with powder of a compound may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting and cooling each compound may be used. In 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 The composition ratio of the plurality of compounds contained corresponds to the composition ratio of the organic layer. An organic layer having a desired composition ratio can be easily formed by mixing a plurality of compounds in the same composition ratio as that of the organic layer 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.

[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 further include the step of mounting a carrier substrate formed of a glass material on the other surface of the base substrate 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 disposed 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 thin film to absorb the impact that can be transmitted to the barrier layer without the organic thin film, so that each unit panel can be soft-cut to prevent damage to the barrier ribs. 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 foregoing 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.).

(Synthesis Example 1) Synthesis of Compound 1b [Chemical Formula 128]

Under nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (2g, 6.19mmol), 3-phenyl-12H-benzofluoro[2,3-a]carbazole (2.06g, 6.19 mmol), tris(dibenzylideneacetone) dipalladium (0) (0.57g, 0.62mmol), tri-tertiary butylphosphonium tetrafluoroborate (0.36g, 1.24mmol) and tertiary sodium butoxide (1.19 g, 12.4mmol) was added into 45ml 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: chloroform/n-hexane=5:5). Further recrystallization (toluene/methanol) was performed to obtain Compound 1b (1.74 g, 49) as a white solid. ¹ H NMR (400MHz, CDCl ₃ , δ): 8.43 (s, 1H), 8.32 (s, 1H), 8.11 (d, J = 8Hz, 1H), 8.07 (m, 2 H), 7.94-7.82 (m , 4H), 7.77-7.68 (m, 6H), 7.65 (d, J =8Hz, 1H), 7.58 (d, J =8Hz, 1H), 7.55-7.31 (m, 8H). MS (ASAP): 576.12 (M+H ⁺ ).Calcd for C ₄₂ H ₂₅ NO ₂ :575.91.

(Synthesis Example 2) Synthesis of Compound 2b [Chemical Formula 129]

Under nitrogen atmosphere, N-bromosuccinimide (13.8 g, 77.7mmol), returned to room temperature, and stirred for 14 hours. After removing the solvent, it was washed with methanol. The obtained solid was dissolved in heated toluene and filtered through a Buchner funnel covered with celite/silica gel/celite. After the solvent of the filtrate was removed, recrystallization was performed with toluene and chlorobenzene, respectively, to obtain white solid intermediate M1 (15.9 g, 61%). ¹ H-NMR (400MHz, CDCl ₃ , δ ): 8.63 (d, J=6.8Hz, 1H), 8.52 (br, 1H), 8.19 (s, 1H), 8.11 (d, J = 7.6Hz, 1H) , 7.67 (d, J =7.6Hz, 1H), 7.57-7.43 (m, 4H), 7.31 (t, J = 7.2Hz, 1H) MS (ASAP): 335.96 (M+H ⁺ ).Calcd for C ₁₈ H ₁₀ BrNO:334.99

[chemical formula 130]

Under nitrogen atmosphere, intermediate M1 (15.8g, 46.9mmol), phenylboronic acid (6.8g, 56.3mmol), tripotassium phosphate (19.9g, 93.9mmol), tetrakis(triphenylphosphine)palladium(0) (2.7 g, 2.3 mmol) in 1,4-dioxane (470 mL)/ultrapure water (150 mL) was stirred at 100° C. for 15 hours. After removing the dioxane, the solid precipitated in water was filtered. The obtained solid was dissolved in heated toluene and filtered through a Buchner funnel covered with celite/silica gel/celite. The solvent of the filtrate was removed, and the intermediate M2 (10.8 g, 69%) was obtained by recrystallization with toluene and chlorobenzene respectively. ¹ H-NMR (400MHz, CDCl ₃ , δ ): 8.54 (s, 1H), 8.13 (d, J =6.8Hz, 1H), 7.93 (s, 1H), 7.72 (dt, J = 6.8Hz, 2Hz2H) , 7.65 (d, J =8.4Hz, 1H), 7.59-7.46 (m, 6H), 7.41 (td, J = 7.8Hz, 1.2Hz, 1H), 7.30 (td, J = 7.6Hz, 1.2Hz, 1H ), 7.16 (td, J =7.6Hz, 1.2Hz, 1H) MS (ASAP): 334.44 (M+H ⁺ ). Calcd for C ₂₄ H ₁₅ NO: 333.12

[chemical formula 131]

Under nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (10.6g, 32.7mmol), intermediate M2 (10.9g, 32.7mmol), tris(dibenzylideneacetone)dipalladium (0 ) (3.0g, 3.2mmol), three-tertiary butylphosphonium tetrafluoroborate (1.9g, 6.5mmol), three-level sodium butoxide (6.3g, 65.6mmol) in toluene solution (240mL) at 130 ° C Stirred for 14 hours. Toluene was added to the reaction solution, and filtered with a Buchner funnel covered with diatomaceous earth/silica gel/diatomaceous earth. After removing the solvent, it was washed with ethyl acetate and filtered to obtain a brown solid. The obtained solid was recrystallized from chlorobenzene and toluene, respectively, to obtain Compound 2b (12.4 g, 65%). ¹ H NMR (400MHz, CDCl ₃ , δ): 8.32 (d, J = 2.0Hz, 1H), 8.22 (d, J = 8.0Hz, 1H), 8.07 (d, J = 1.7Hz, 1H), 8.04 ( s, 1H), 7.89-7.83 (m, 3H), 7.78-7.73 (m, 4H), 7.66 (d, J = 8.4Hz, 2H), 7.61-7.57 (m, 3H), 7.54-7.44 (m, 5H), 7.38-7.30 (m, 3H), 7.17-7.13 (td, J =7.4Hz, 1.2Hz, 1H) MS (ASAP): 576.37 (M+H ⁺ ). Calcd for C ₄₂ H ₂₅ NO ₂ : 575.19.

(Synthesis Example 3) Synthesis of Compound 6b [Chemical Formula 132]

Under nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (1.78g, 5.5mmol), 2-phenyl-12H-benzofluoro[2,3-a]carbazole (2.2g, 6.6mmol), three (dibenzylideneacetone) dipalladium (0) (5.03g, 0.55mmol), three-three-level butyl phosphorus tetrafluoroborate (0.319g, 1.1mmol) and three-level sodium butoxide ( 1.59g, 16.5mmol) was added to 50ml 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: chloroform/n-hexane=3:7). Further recrystallization (toluene/methanol) was performed to obtain compound 6b (2.24 g, 77) as a white solid. ¹ H NMR (400MHz, CDCl ₃ , δ): 8.32 (d, J = 2Hz, 1H), 8.28 (d, J = 8Hz, 1H), 8.18 (d, J = 8Hz, 1H), 8.09-8.06 (m , 2H), 7.93 (d, J = 8Hz, 1H), 7.88-7.82 (m, 3H), 7.79-7.75 (m, 2H), 7.71-7.58 (m, 5H), 7.54-7.31 (m, 10H) . MS (ASAP): 576.33 (M+H ⁺ ). Calcd for C ₄₂ H ₂₅ NO ₂ : 575.91.

(Synthesis Example 4) Synthesis of Compound 19b [Chemical Formula 133]

Under nitrogen atmosphere, 2-(3-bromophenyl)dibenzofuran (0.97g, 3mmol), 2-phenyl-5H-benzofluoro[3,2-c]carbazole (1g, 3mmol) , tris(dibenzylideneacetone) dipalladium (0) (0.27g, 0.3mmol), tri-tertiary butylphosphonium tetrafluoroborate (0.17g, 0.6mmol) and tertiary sodium butoxide (0.58g, 6mmol) was added to 15ml 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: chloroform/n-hexane=2:8). Further recrystallization (toluene/methanol) was performed to obtain Compound 19b (1.09 g, 63) as a white solid. ¹ H NMR (400MHz, CDCl ₃ , δ): 8.81 (s, 1H), 8.24 (s, 1H), 8.02-7.97 (m, 4H), 7.88-7.72 (m, 7H), 7.69-7.33 (m, 12H). MS (ASAP): 575.21 (M+H ⁺ ). Calcd for C ₄₂ H ₂₅ NO ₂ : 575.91.

(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 50 nm was formed by the vacuum evaporation method to produce organic electroluminescent elements. First, HATCN with a thickness of 10 nm was formed on ITO, NPD with a thickness of 30 nm was formed thereon, and compound 1b was formed with a thickness of 10 nm thereon. Next, the host material (H1) and the delayed fluorescent material (T132) 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 host material was set to 65% by mass, and the content of the delayed fluorescent material was set to 35% 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 . In addition, organic electroluminescent elements were produced by the same procedure except that compounds 6b, 19b, and 22 were used instead of compound 1b, and these were respectively referred to as EL elements 2 to 4. Furthermore, only the point of using Comparative Compound A and Comparative Compound B instead of Compound 1b was changed, and organic electroluminescent devices were produced by the same procedure, and these were respectively referred to as Comparative EL Device 1 and Comparative EL Device 2 . Electricity was applied to each of the produced organic electroluminescence elements, and as a result, delayed fluorescence derived from the delayed fluorescent material (T132) was observed. 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 (LT95) was measured. The measurement results are shown in Table 2. LT95 in Table 2 is shown as a relative value when LT95 of Comparative EL element 2 is set to 1. As a result of the measurement, it was found that when the compound represented by the general formula (1) was used as an electron barrier material, the device life was remarkably longer than that of Comparative Compound A or Comparative Compound B, which was conventionally used as an electron barrier material.

[Table 2] Part number Electron barrier material LT95 EL element 1 Compound 1b 2.01 times EL element 2 Compound 6b 1.77 times EL element 3 Compound 19b 1.40 times EL element 4 Compound 22 1.32 times Compare EL Elements 1 Comp A 1.23 times Compare EL Elements 2 Comp B 1

(Example 2) The light-emitting layer in Example 1 was changed to co-evaporate the host material (H1), delayed fluorescent material (T132) and fluorescent material (E1) from different evaporation sources and their contents depend on An organic electroluminescent device was fabricated by the same procedure as in Example 1 except that the light-emitting layer with a thickness of 40 nm was 64.2 mass %, 35.0 mass %, and 0.8 mass %. This element is referred to as the EL element 5 . Also, except for changing the point of using compounds 2b and 19b instead of compound 1b, organic electroluminescence elements were fabricated by the same procedure, and these were used as EL elements 6 and 7, respectively. As a result of energizing each produced organic electroluminescence element, delayed fluorescence from the fluorescent material (E1) was observed. The organic electroluminescent element was driven at 6.3mA/ ^cm2 , and the external quantum efficiency (EQE) and initial driving voltage were measured, and each organic electroluminescent element was driven at a current density of 12.6mA/ ^cm2 , and the The time until the luminous intensity becomes 95% of that at the start of driving (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 7 is set to 1, and the driving voltage is shown as a relative value with the EL element 7 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 electron barrier material is high, and the drive The voltage is low and the component life is long.

[table 3] Part number Electron barrier material EQE (%) Driving voltage (V) LT95 EL element 5 Compound 1b 0.93 times 0.06 1.2 times EL element 6 Compound 2b 0.93 times -0.09 1.2 times EL element 7 Compound 19b 1 0 1

(Example 3) The light-emitting layer in Example 1 was changed to co-evaporate the host material (H1) and delayed fluorescent material (T136) from different evaporation sources, and the contents were 65% by mass, 35% by mass, An organic electroluminescent device was produced by the same procedure as in Example 1 except that the light emitting layer had a thickness of 40 nm in mass %. This element is referred to as the EL element 8 . Also, except for changing the point of using compound 2b instead of compound 1b, organic electroluminescent elements were produced by the same procedure, and these were respectively used as EL elements 9 . Electricity was applied to each of the produced organic electroluminescence elements, and as a result, delayed fluorescence derived from the delayed fluorescent material (T136) was observed. The fabricated organic electroluminescent element was driven at 6.3mA/cm ² , 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 4. EQE and LT95 in Table 4 are shown as relative values when LT95 of the EL element 9 is set to 1, and the driving voltage is shown as a relative value with the EL element 9 as a reference (0). The measurement results show that even when a delayed fluorescent material different from that of Example 1 is used, the luminous efficiency of the device using the compound represented by the general formula (1) as the electron barrier material is high, and the driving voltage is low. Component life is long.

[Table 4] Part number Electron barrier material EQE (%) Driving voltage (V) LT95 EL element 8 Compound 1b 0.96 times -0.06 1.4 times EL element 9 Compound 2b 1 0 1

[產業上之可利用性] (Example 4) 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 50 nm was formed by vacuum evaporation to produce organic electroluminescent elements. First, HAT-CN with a thickness of 60nm was formed on ITO, TrsPCz with a thickness of 30nm was formed on it, and PYD2Cz with a thickness of 5nm was formed thereon. Next, the host material (reference compound a) and the retarded fluorescent material (T3) were co-evaporated from different deposition sources to form a layer with a thickness of 30 nm, which was used as a light-emitting layer. At this time, the content of the host material was set to 70% by mass, and the content of the delayed fluorescent material was set to 30% 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 was set as a reference EL element 1 . The produced organic electroluminescent element was driven at 2mA/cm ² , and the external quantum efficiency (EQE) was measured. As a result, it showed a high value of 21.9%. From this, it can be seen that the reference compound a is an excellent material as a host material. On the other hand, an organic electroluminescent element was produced by the same procedure except that the compound 1a was used instead of PYD2Cz, and this was used as a reference EL element 2 . The produced organic electroluminescent device was driven at 2mA/cm ² , and the external quantum efficiency (EQE) was measured. As a result, it decreased to 17.1%. Therefore, it can be seen that the reference compound a is not suitable as an electron barrier material. The above results show that even if it is a useful host material, it is useless as an electron barrier material, and it is not easy to find a useful electron barrier material. [chemical formula 134]

[Industrial availability]

The compound represented by the general formula (1) is useful as an electron barrier material and can be used in an organic semiconductor device. When the compound of the present invention is used in the electron barrier layer of an organic electroluminescence element, the lifetime of the element can be extended. Therefore, the industrial applicability of this invention is high.

Claims (16)

A use of a compound represented by the following general formula (1) as an electron barrier material, [Chemical Formula 1]

In the formula, R ¹ to R ⁵ independently represent a deuterium atom or a substituent that does not contain a cyano group, and R ¹ to R ⁵ do not bond with other R ¹ to R ⁵ or Ar to form a ring structure, but adjacent ^R3 can be bonded to each other to form a benzofluorine skeleton or a benzothieno skeleton, n1, n3, and n5 independently represent any integer from 0 to 4, n2 represents any integer from 0 to 3, and n4 Represents any integer from 0 to 2, X represents an oxygen atom or a sulfur atom, Ar represents a monocyclic aryl or a monocyclic heteroaryl, the aforementioned monocyclic aryl and the aforementioned monocyclic heteroaryl can be deuterated Atoms or substituents that do not contain cyano groups. The use as an electron barrier material as described in claim 1, wherein the aforementioned compound has a structure represented by the following general formula (2A), [chemical formula 2]

In the formula, R ¹ to R ⁶ independently represent a deuterium atom or a substituent that does not contain a cyano group, and R ¹ to R ⁶ do not bond with other R ¹ to R ⁶ to form a ring structure, but the adjacent R ³ They can be bonded to each other to form a benzofluorine skeleton or a benzothieno skeleton, n1, n3, and n5 independently represent any integer from 0 to 4, and n2 and n6 independently represent any one of 0 to 3 Integer, n4 represents any integer from 0 to 2, and X represents an oxygen atom or a sulfur atom. The use as an electron barrier material as described in claim 1, wherein the aforementioned compound has a structure represented by the following general formula (2B), [chemical formula 3]

In the formula, R ¹ to R ⁶ independently represent a deuterium atom or a substituent that does not contain a cyano group, and R ¹ to R ⁶ do not bond with other R ¹ to R ⁶ to form a ring structure, but the adjacent R ³ They can be bonded to each other to form a benzofluorine skeleton or a benzothieno skeleton, n1, n3, and n5 independently represent any integer from 0 to 4, and n2 and n6 independently represent any one of 0 to 3 Integer, n4 represents any integer from 0 to 2, and X represents an oxygen atom or a sulfur atom. The use as an electron barrier material as described in claim 1, wherein the aforementioned compound has a structure represented by the following general formula (3), [chemical formula 4]

In the formula, R ¹ to R ⁶ independently represent a deuterium atom or a substituent that does not contain a cyano group, and R ¹ to R ⁶ do not bond with other R ¹ to R ⁶ to form a ring structure, but the adjacent R ³ They can be bonded to each other to form a benzofluorine skeleton or a benzothieno skeleton, n1, n3, and n5 independently represent any integer from 0 to 4, and n2 and n6 independently represent any one of 0 to 3 Integer, n4 represents any integer from 0 to 2, wherein, n1+n3+n4+n5 is more than 1, and one or two of R ¹ and R ³ to R ⁵ represent an alkyl group that can be deuterated or can be deuterated A phenyl group substituted with a deuterium atom, X represents an oxygen atom or a sulfur atom. Use as an electron barrier material as described in Claim 2, wherein n1, n2, and n6 are 0. Use as an electron barrier material as described in Claim 1, wherein n3 to n5 are each independently 0 or 1. The use as an electron barrier material as described in claim 1, which has any one of the following structures, [chemical formula 5]

. The use as an electron barrier material as described in any one of claim 1 to claim 7, which is used in combination with a compound represented by the following general formula (G), general formula (G) [chemical formula 6]

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 semiconductor device comprising the compound described in any one of claim 1 to claim 7. The organic semiconductor device according to claim 9, wherein The aforementioned organic semiconductor element is an organic electroluminescent element, which has an anode, a cathode, and at least two organic layers comprising an electron barrier layer and a light-emitting layer comprising the aforementioned electron barrier material between the aforementioned anode and the aforementioned cathode. The organic semiconductor device according to claim 10, wherein The aforementioned light-emitting layer includes a host material and a delayed fluorescent material. The organic semiconductor device according to claim 10, wherein The light-emitting layer includes a host material, a delayed fluorescent material, and a fluorescent light-emitting material, and the amount of light emitted from the fluorescent light-emitting material is the largest among the light emitted from the device. The organic semiconductor device according to claim 10, wherein The aforementioned light emitting layer is adjacent to the aforementioned electron barrier layer. The organic semiconductor device according to any one of claim 10 to claim 13, wherein the light-emitting layer comprises a compound represented by the following general formula (G), general formula (G) [chemical formula 7]

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. The organic semiconductor device according to any one of claim 10 to claim 13, wherein the light-emitting layer comprises a compound represented by the following general formula (4), [Chemical formula 8]

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 mentioned here are not cyano groups, the following general formula (5 ), the group represented by the following general formula (6), [chemical formula 9]

In the general formula (5), L ¹ represents a single bond or a divalent linking group, R ³¹ and R ³² independently represent a hydrogen atom or a substituent, * represents a bonding position, [Chemical Formula 10]

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. A compound represented by the following general formula (3), [Chemical Formula 11]

In the formula, R ¹ to R ⁶ independently represent a deuterium atom or a substituent that does not contain a cyano group, and R ¹ to R ⁵ do not bond with other R ¹ to R ⁶ to form a ring structure, but the adjacent R ³ They can be bonded to each other to form a benzofluorine skeleton or a benzothieno skeleton, n1, n3, and n5 independently represent any integer from 0 to 4, and n2 and n6 independently represent any one of 0 to 3 Integer, n4 represents any integer from 0 to 2, wherein, n1+n3+n4+n5 is more than 1, and one or two of R ¹ and R ³ to R ⁵ represent an alkyl group that can be deuterated or can be deuterated A phenyl group substituted by a deuterium atom, X represents an oxygen atom or a sulfur atom, wherein, when n3+n4+n5 is 0, ^R1 is not an unsubstituted phenyl group.