Compound, light-emitting material, and organic photosemiconductor element

Abstract

To provide a compound exhibiting excellent properties that manifest a multi-resonance effect.SOLUTION: The compound represented by the general formula in the figure, where: X represents B, Al, or P; Y represents N(R), O, S, C(R)2, or Si(R)2; RA and RA' represent H, D, N(R), OH, SH, or the like; RB to RD and RB' to RD' represent H, D, an alkyl group, or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound having excellent properties, and also to a light-emitting material using the compound, and an organic optical semiconductor device such as an organic light-emitting device using the compound. [Background technology]

[0002] Organic light-emitting devices such as organic light-emitting diodes (OLEDs) are being actively researched. For example, Non-Patent Document 1 describes that by using a compound that exhibits a multiple resonance effect, such as 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (DABNA-1), thermally activated delayed fluorescence due to a reverse intersystem crossing process is exhibited, resulting in emission of a narrow half-width and high color purity. Such emission can achieve high luminous efficiency, making it useful for display-oriented applications. Furthermore, Non-Patent Documents 1 and 2 describe that by modifying DABNA-1, the energy levels of the highest accessible molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are adjusted, and the fluorescence emission process and reverse intersystem crossing process that contribute to light emission are promoted, thereby improving the electroluminescence quantum efficiency. [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Adv. Mater. 2016, 28, 2777-2781 [Non-patent document 2] Angew. Chem. Int. Ed. 2018, 57, 11316-11320 Summary of the Invention [Problem to be solved by the invention]

[0004] Although various studies have been conducted on compounds that exhibit the multiple resonance effect, there are still many unknowns regarding the relationship between their structure and properties. In order to manufacture practical light-emitting devices, it is necessary to provide materials with even slightly better properties. Therefore, the present inventors have investigated the relationship between derivatives of compounds that exhibit multiple resonance effects and their properties, and have carried out extensive research with the aim of generalizing structures that exhibit excellent properties. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have found that, among compounds that exhibit multiple resonance effects, compounds having a specific structure have excellent properties. The present invention has been proposed based on this finding and has the following configuration.

[0006] [1] A compound represented by the following general formula (1): General formula (1) [ka] [In the general formula (1), Each X represents B, Al or P. Y is N(R 14 ), O or S. A is N(R 14 ), O, S, C(R 15 )(R 16 ) or Si(R 17 )(R 18 ) R A and R A’ are each independently a hydrogen atom, a deuterium atom, or N(R 14 ), OH, SH, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may be linked to other atoms to form a fused ring. R B ~R D and R B’ ~R D’each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or forms a condensed ring by combining with other atoms. B’ and R C’ do not bond to each other to form a fused ring. R 14 ~R 18 each independently represents a hydrogen atom, a deuterium atom, or a substituent, or is linked to another atom to form a fused ring. [2] R D and R D’ is not linked to another atom to form a fused ring. [3] If Y is N(R 14 ) The compound according to [1] or [2], [4] The compound according to any one of [1] to [3], which is represented by the following general formula (1a): General formula (1a) [ka] [In the general formula (1a), Each X represents B, Al or P. A is N(R 14 ), O, S, C(R 15 )(R 16 ) or Si(R 17 )(R 18 ) Z and Z' each independently represent a single bond, C(R 15 )(R 16 ), O, S or Si(R 17 )(R 18 ) R 1 ~R 11 and R 1’ ~R 13’ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or forms a condensed ring by combining with other atoms. 12’ and R 13’ do not bond to each other to form a fused ring. R 14~R 18 each independently represents a hydrogen atom, a deuterium atom, or a substituent, or is linked to another atom to form a fused ring. [5] The compound according to any one of [1] to [4], wherein each X is B. [6] A is N(R 14 The compound according to any one of [1] to [5], wherein [7] A is C(R 15 )(R 16 The compound according to any one of [1] to [6], wherein [8] The compound according to any one of [1] to [7], wherein A is O. [9] The compound according to any one of [4] to [8], wherein Z and Z' are both single bonds.

[10] The compound according to any one of [4] to [9], wherein Z and Z' are the same.

[11] R 3 , R 7 , R 9 , R 3’ and R 6’ The compound according to any one of [4] to [9], wherein at least one of the groups is a substituted or unsubstituted alkyl group.

[12] A light-emitting material comprising the compound according to any one of [1] to

[11] .

[13] A film comprising the compound according to any one of [1] to

[11] .

[14] An organic optical semiconductor device comprising the compound according to any one of [1] to

[11] .

[15] The organic optical semiconductor element according to

[14] , which is an organic light-emitting element.

[16] The organic optical semiconductor element according to

[15] , which is an organic electroluminescence element.

[17] The organic optical semiconductor element according to

[16] , wherein the organic electroluminescence element has a layer containing the compound, and the layer also contains a host material.

[18] The organic optical semiconductor element according to

[17] , wherein the layer contains, in addition to the compound and the host material, a delayed fluorescent material having a structure outside the scope of the general formula (1), and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

[19] The organic optical semiconductor element according to

[18] , wherein the compound emits the greatest amount of light among the materials contained in the organic electroluminescence element.

[20] The organic optical semiconductor element according to

[16] , wherein the organic electroluminescence element has a layer containing the compound, and the layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

[21] The organic optical semiconductor element according to

[20] , wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

[22] The organic optical semiconductor element according to any one of

[15] to

[21] , which emits delayed fluorescence. [Effects of the Invention]

[0007] The compound of the present invention has excellent properties and can be used as a light-emitting material. The compound of the present invention can also be used to produce organic optical semiconductor devices such as organic light-emitting devices. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( 2In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom constituting the ring skeleton at the omitted position. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0009] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be explained. [ka]

[0010] In general formula (1), two X's are the same and each represents B, Al, or P. In one embodiment of the present invention, X's is B. In one embodiment of the present invention, X's is Al or P, for example, Al, for example, P. In general formula (1), two Ys are the same and both are N(R 14 ), O or S. In one aspect of the invention, Y represents N(R 14 In one aspect of the invention, X is O or S, such as O, for example S. In one embodiment of the invention, X is B and Y is N(R 14 ) In one aspect of the invention, X is B and Y is O. In one aspect of the invention, X is B and Y is S. In one aspect of the invention, X is Al and Y is N(R 14 ) In one aspect of the invention, X is Al and Y is O. In one aspect of the invention, X is Al and Y is S. In one aspect of the invention, X is P and Y is N(R 14 ) In one aspect of the invention, X is P and Y is O. In one aspect of the invention, X is P and Y is S.

[0011] A in the general formula (1) is N(R 14), O, S, C(R 15 )(R 16 ) or Si(R 17 )(R 18 In one aspect of the invention, A represents N(R 14 ). In one aspect of the invention, N is O or S. In one aspect of the invention, A is C(R 15 )(R 16 In one aspect of the invention, A is Si(R 17 )(R 18 ) In one embodiment of the present invention, X is B and Y and A are each independently N(R 14 In one embodiment of the present invention, X is B and Y is N(R 14 ) and A is O or S. In one aspect of the invention, X is B and Y is N(R 14 ), and A is C(R 15 )(R 16 In one embodiment of the present invention, X is B and Y is N(R 14 ) and A is Si(R 17 )(R 18 In one embodiment of the present invention, X is B, Y is O or S, and A is N(R 14 ) In one aspect of the invention, X is B, Y is O or S, and A is O or S. In one aspect of the invention, X is B, Y is O or S, and A is C(R 15 )(R 16 In one embodiment of the present invention, X is B, Y is O or S, and A is Si(R 17 )(R 18 In one embodiment of the present invention, X is Al or P, and Y and A are each independently N(R 14 In one embodiment of the present invention, X is Al or P and Y is N(R 14 ) and A is O or S. In one aspect of the invention, X is Al or P and Y is N(R 14 ), and A is C(R 15 )(R 16 In one embodiment of the present invention, X is Al or P and Y is N(R 14 ) and A is Si(R 17 )(R 18 )

[0012] R in general formula (1) A and R A’ are each independently a hydrogen atom, a deuterium atom, or N(R 14 ), OH, SH, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or forms a fused ring when linked to other atoms. A and R A’ are each independently N(R 14 In one aspect of the present invention, R A and R A’ are each independently O or S. In one aspect of the invention, R A and R A’ are each independently a substituted or unsubstituted alkyl group. In one aspect of the present invention, R A and R A’ are each independently a substituted or unsubstituted aryl group. A and R A’ In one aspect of the invention, R A and R A’ In one aspect of the invention, Y is N(R 14 ) and R 14 and R A , R 14’ and R A’ are bonded to each other to form a fused ring.

[0013] R in general formula (1) B ~R D and R B’ ~R D’ Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. B , R B’ , R C and R C’ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. B and three R's B’ is selected so as to have a point-symmetric structure with respect to the center of the central benzene ring of general formula (1). C’At least one of R is a substituted or unsubstituted alkyl group, for example, 2 to 4 are substituted or unsubstituted alkyl groups, for example, 2 or 3 are substituted or unsubstituted alkyl groups. C At least one of R is a substituted or unsubstituted alkyl group, for example, one is a substituted or unsubstituted alkyl group, for example, two are substituted or unsubstituted alkyl groups. D and R D’ may be the same or different, but are preferably the same. D and R D’ are each independently a hydrogen atom or a deuterium atom. R B ~R D and R B’ ~R D’ may be linked to other atoms to form a condensed ring. B’ and R C’ do not bond to each other to form a fused ring. B ~R D and R B’ ~R D’ In one embodiment of the present invention, Y is N(R 14 ) and R 14 and R D , R 14’ and R D’ are bonded to each other to form a fused ring. A and R B , R A’ and R B’ are bonded to each other to form a fused ring. C and R D , R C’ and R D’ are bonded to each other to form a fused ring. In one embodiment of the present invention, A is N(R 14 ) and R 14 and R B are bonded to each other to form a fused ring. In one embodiment of the present invention, A is N(R 14 ) and R 14 and R Care bonded to each other to form a fused ring.

[0014] R 14 ~R 18 each independently represents a hydrogen atom, a deuterium atom, or a substituent, or is linked to another atom to form a fused ring. The substituent may be selected, for example, from substitution candidate group A described below, from substitution candidate group B described below, from substitution candidate group C described below, from substitution candidate group D described below, or from substitution candidate group E described below. In one aspect of the present invention, R 14 is an alkyl group which may be substituted with a substituent selected from substitution candidate group E or a deuterium atom, or an aryl group which may be substituted with a substituent selected from substitution candidate group E or a deuterium atom. In general formula (1), R 14 If there are multiple R 14 Each one is different from the other R 14 In one aspect of the present invention, R 15 ~R 18 are each independently a hydrogen atom, a deuterium atom, an alkyl group which may be substituted with a substituent selected from substitution candidate group E or a deuterium atom, or an aryl group which may be substituted with a substituent selected from substitution candidate group E or a deuterium atom. In one embodiment of the present invention, R 15 and R 16 In one aspect of the invention, R 17 and R 18 In one aspect of the invention, R 14 may be linked to other atoms to form a condensed ring, but R 15 ~R 18 does not form a fused ring with another atom.

[0015] For details of the "fused ring" in the above explanation of general formula (1), reference can be made to the corresponding description of general formula (1a) below.

[0016] The compound represented by general formula (1) preferably has a structure represented by the following general formula (1a). General formula (1a) [ka]

[0017] In the general formula (1a), X represents B, Al, or P. In the general formula (1a), A represents N(R 14 ), O, S, C(R 15 )(R 16 ) or Si(R 17 )(R 18 For details of X and A, the corresponding descriptions in general formula (1) can be referred to.

[0018] In the general formula (1a), Z and Z′ each independently represent a single bond, C(R 15 )(R 16 ), O, S or Si(R 17 )(R 18 In a preferred embodiment of the present invention, Z and Z' are single bonds. In one embodiment of the present invention, Z and Z' each independently represent C(R 15 )(R 16 In one embodiment of the present invention, Z and Z' are each independently O or S. In one embodiment of the present invention, Z and Z' are each independently Si(R 17 )(R 18 ). In one embodiment of the invention, Z and Z' are the same. In one embodiment of the invention, Z and Z' are different. In one embodiment of the invention, Z is C(R 15 )(R 16 ) or Si(R 17 )(R 18 ) and R 15 ~R 18 and R 4 , R 15 ~R 18 and R 5 In one embodiment of the present invention, Z' is C(R 15 )(R 16 ) or Si(R 17 )(R 18 ) and R 15 ~R 18 and R 4’ , R15 ~R 18 and R 5’ In one embodiment of the present invention, Z' is C(R 15 )(R 16 ) or Si(R 17 )(R 18 ) and R 15 ~R 18 is not linked to any other atom to form a fused ring. In one aspect of the invention, X is B and A is N(R 14 ) and Z and Z' are single bonds. In one embodiment of the invention, X is B and A is N(R 14 ) and Z and Z' are O or S. In one embodiment of the invention, X is B and A is N(R 14 ), where Z and Z' are C(R 15 )(R 16 In one aspect of the invention, X is B and A is N(R 14 ), where Z and Z' are Si(R 17 )(R 18 ) In one embodiment of the present invention, X is B, A is O or S, and Z and Z' are single bonds. In one embodiment of the present invention, X is B, A is C(R 15 )(R 16 ) and Z and Z' are single bonds. In one embodiment of the present invention, X is B and A is Si(R 17 )(R 18 ) and Z and Z' are single bonds. In one embodiment of the invention, X is Al and A is N(R 14 ) and Z and Z' are single bonds. In one embodiment of the invention, X is P and A is N(R 14 ) where Z and Z' are single bonds. In general formula (1a), R 15 If there are multiple R 15 Each one is different from the other R 15 may be the same as or different from R 16 If there are multiple R 16 Each one is different from the other R 16 may be the same as or different from R 17 If there are multiple R 17Each one is different from the other R 17 may be the same as or different from R 18 If there are multiple R 18 Each one is different from the other R 18 It may be the same as or different from.

[0019] R in general formula (1a) 1 ~R 11 and R 1’ ~R 13’ Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 3 ~R 10 and R 3’ ~R 10’ At least one of R is a substituted or unsubstituted alkyl group, for example, 1 to 12 are substituted or unsubstituted alkyl groups, for example, 2 to 8 are substituted or unsubstituted alkyl groups, and 2 to 6 are substituted or unsubstituted alkyl groups. 3 , R 7 , R 9 , R 3’ and R 6’ At least one of R is a substituted or unsubstituted alkyl group, for example, 2 to 5 are substituted or unsubstituted alkyl groups, for example, 2 to 3 are substituted or unsubstituted alkyl groups, for example, 4 to 5 are substituted or unsubstituted alkyl groups. 3’ and R 6’ are each independently a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R 7’ , R 8’ , R 9’ , R 10’ and R 13’ At least one of R is a substituted or unsubstituted alkyl group, for example, 2 to 5 are substituted or unsubstituted alkyl groups, for example, 2 to 3 are substituted or unsubstituted alkyl groups, for example, 4 to 5 are substituted or unsubstituted alkyl groups. 8’ , R 10’ , R 13’are each independently a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R 7’ , R 9’ are each independently a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R 10’ , R 13’ are each independently a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R 1 ~R 11 and R 1’ ~R 13’ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. 1 ~R 11 and R 1’ ~R 13’ are each independently a hydrogen atom or a deuterium atom. 3 ~R 8 and R 3’ ~R 8’ At least one of R is a substituted or unsubstituted aryl group, for example, 1 to 6 of R are substituted or unsubstituted aryl groups. 1 , R 10 , R 11 , R 1’ , R 10’ , R 11’ are each independently a hydrogen atom or a deuterium atom.

[0020] R in general formula (1a) 1 ~R 11 and R 1’ ~R 13’ may be linked to other atoms to form a condensed ring. 12’ and R 13’ do not bond to each other to form a fused ring. For example, R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 10 and R 11 , R 11 and R 1’ , R 3’ and R 4’ , R 5’ and R6’ , R 7’ and R 8’ , R 10’ and R 11’ , R 11’ and R 1 may be bonded to each other to form a condensed ring. The "fused ring" in this specification may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring formed by condensing these. An aromatic ring or a heteroaromatic ring is preferred. An example of an aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. A hydrogen atom, a deuterium atom, or a substituent is bonded to the skeleton atom constituting the fused ring. The substituent referred to here may be substituted with a substituent or a deuterium atom selected from substitution candidate group A described below, or may be substituted with a substituent or a deuterium atom selected from substitution candidate group B described below, or may be substituted with a substituent or a deuterium atom selected from substitution candidate group C described below, or may be substituted with a substituent or a deuterium atom selected from substitution candidate group D described below, or may be substituted with a substituent or a deuterium atom selected from substitution candidate group E described below.

[0021] R in general formula (1a) 14 ~R 18 R each independently represents a hydrogen atom, a deuterium atom, or a substituent, or forms a condensed ring when linked to other atoms. 14 ~R 18 For details of the formula (1), reference can be made to the corresponding description.

[0022] Compound group 1 of the present invention includes compounds of general formula (1a) in which X is B and A is N(R 14Compound group 1 includes compound group 1a in which Z and Z' in general formula (1a) are single bonds; and compound group 1b in which Z and Z' in general formula (1a) are C(R 15 )(R 16 a compound group 1b in which Z and Z' in the general formula (1a) are O; a compound group 1c in which Z and Z' in the general formula (1a) are S; a compound group 1d in which Z and Z' in the general formula (1a) are Si(R 17 )(R 18 ) is included in the compound group 1e. For each of these compound groups 1a to 1e, there can be exemplified an embodiment in which the following additional condition is also satisfied. One of the additional conditions is that R 3 ~R 10 and R 3’ ~R 10’ At least one of R in general formula (1a) is a substituted or unsubstituted alkyl group. 3 , R 7 , R 9 , R 3’ and R 6’ At least one of R in general formula (1a) is a substituted or unsubstituted alkyl group. 7’ , R 8’ , R 9’ , R 10’ and R 13’ At least one of R in general formula (1a) is a substituted or unsubstituted alkyl group. 1 ~R 11 and R 1’ ~R 13’ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. One additional condition is that R 1 ~R 11 and R 1’ ~R 13’ are each independently a hydrogen atom or a deuterium atom. One additional condition is that R 3 ~R 8 and R 3’ ~R 8’ At least one of R in general formula (1a) is a substituted or unsubstituted aryl group. 1, R 10 , R 11 , R 1’ , R 10’ , R 11’ are each independently a hydrogen atom or a deuterium atom. One additional condition is that R 1 ~R 11 and R 1’ ~R 13’ does not form a condensed ring with other atoms. One additional condition is that R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 10 and R 11 , R 11 and R 1’ , R 3’ and R 4’ , R 5’ and R 6’ , R 7’ and R 8’ , R 10’ and R 11’ , R 11’ and R 1 At least one pair of these is bonded to each other to form a fused ring.

[0023] Compound group 2 of the present invention includes a compound group in which X in general formula (1a) is B and A is O. Compound group 2 includes compounds in general formula (1a) where Z and Z' are single bonds; and compounds in general formula (1a) where Z and Z' are C(R 15 )(R 16 a compound group 2b in which Z and Z' in the general formula (1a) are O; a compound group 2c in which Z and Z' in the general formula (1a) are S; a compound group 2d in which Z and Z' in the general formula (1a) are Si(R 17 )(R 18 For each of these compound groups 2a to 2e, there can be mentioned an embodiment in which the additional conditions described for compound groups 1a to 1e are also satisfied.

[0024] Compound group 3 of the present invention includes a compound group in which X in general formula (1a) is B and A is S. Compound group 3 includes compound group 3a in which Z and Z' in general formula (1a) are single bonds; and compound group 3b in which Z and Z' in general formula (1a) are C(R 15 )(R 16 a compound group 3b in which Z and Z' in the general formula (1a) are O; a compound group 3c in which Z and Z' in the general formula (1a) are S; a compound group 3d in which Z and Z' in the general formula (1a) are Si(R 17 )(R 18 For each of these compound groups 3a to 3e, there can be mentioned an embodiment in which the additional conditions described for compound groups 1a to 1e are also satisfied.

[0025] Compound group 4 of the present invention includes compounds of general formula (1a) in which X is B and A is C(R 15 )(R 16 Compound group 4 includes compound group 4a in which Z and Z' in general formula (1a) are single bonds; and compound group 4b in which Z and Z' in general formula (1a) are C(R 15 )(R 16 a compound group 4b in which Z and Z' in the general formula (1a) are O; a compound group 4c in which Z and Z' in the general formula (1a) are S; a compound group 4d in which Z and Z' in the general formula (1a) are Si(R 17 )(R 18 For each of these compound groups 4a to 4e, there can be mentioned an embodiment in which the additional conditions described for compound groups 1a to 1e are also satisfied.

[0026] Compound group 5 of the present invention includes compounds represented by general formula (1a) in which X is B and A is Si(R 17 )(R 18 Compound group 5 includes compound group 5a in which Z and Z' in general formula (1a) are single bonds; and compound group 5b in which Z and Z' in general formula (1a) are C(R 15 )(R 16 a compound group 5b in which Z and Z' in the general formula (1a) are O; a compound group 5c in which Z and Z' in the general formula (1a) are S; a compound group 5d in which Z and Z' in the general formula (1a) are Si(R17 )(R 18 For each of these compound groups 5a to 5e, there can be mentioned an embodiment in which the additional conditions described for compound groups 1a to 1e are also satisfied.

[0027] In compound groups 1 to 5, X is B, but when B is replaced with Al, the resulting compounds are classified as compound groups 6 to 10. In compound groups 1 to 5, X is B, but when B is replaced with P, the resulting compounds are classified as compound groups 11 to 15.

[0028] The compound represented by general formula (1) preferably does not contain a metal atom. The metal atom here does not include a boron atom. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of boron, carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In one embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of boron, carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of boron, carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of boron, carbon, hydrogen, deuterium, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound that does not contain a hydrogen atom but contains a deuterium atom.

[0029] As used herein, the term "substitution candidate group" refers to a set (group) of elements used to substitute a hydrogen atom, and may include not only substituents but also deuterium atoms. In the present specification, "substitution candidate group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryl It refers to a group consisting of a thio group (for example, having 5 to 30 atoms constituting the ring skeleton), an acyl group (for example, having 1 to 40 carbon atoms), an alkenyl group (for example, having 1 to 40 carbon atoms), an alkynyl group (for example, having 1 to 40 carbon atoms), an alkoxycarbonyl group (for example, having 1 to 40 carbon atoms), an aryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms) and a nitro group, and a group consisting of a combination of two or more atoms or substituents selected from this group. As used herein, "substitution candidate group B" refers to a group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms), and a group consisting of a combination of two or more elements (atoms or groups) selected from this group. As used herein, "substitution candidate group C" refers to a group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), and a group consisting of a combination of two or more elements selected from this group. As used herein, "substitution candidate group D" refers to a group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 atoms constituting the ring skeleton), and a group consisting of a combination of two or more elements selected from this group. As used herein, "substitution candidate group E" refers to a group consisting of a group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms), and a group consisting of a combination of two elements selected from this group. In the present specification, when "substituted or unsubstituted" or "optionally substituted" is used, the element used for substitution may be selected from replacement candidate group A, or may be selected from replacement candidate group B, or may be selected from replacement candidate group C, or may be selected from replacement candidate group D, or may be selected from replacement candidate group E, for example.

[0030] In the following, A in general formula (1) is N(R 14 Specific examples of the linking group represented by general formula (N) are shown below. General formula (N) [ka]

[0031] E in general formula (N) 1 ~E 5 each independently represents a hydrogen atom, a deuterium atom, or a substituent. * represents a bonding site. The substituent may be selected from the above substitution candidate group A, may be selected from the above substitution candidate group B, may be selected from the above substitution candidate group C, may be selected from the above substitution candidate group D, or may be selected from the above substitution candidate group E. In one aspect of the present invention, E 1 ~E 5 are each independently a hydrogen atom (H), a deuterium atom (D), or any of the following Y1 to Y5. [ka]

[0032] E 3 ~E 5 When is a hydrogen atom (H), a deuterium atom (D), or any of Y1 to Y5, the combinations are shown as Q1 to Q343 in Table 1 below. [Table 1] JPEG2025159576000008.jpg243133

[0033] Specific examples of the linking group represented by general formula (N) are shown in Table 2 below. In Table 2, E in general formula (N) 1 ~E 5 By specifying the above, the structures of N1 to N343, which are specific examples of A, are specified. [Table 2] JPEG2025159576000010.jpg236140

[0034] In Table 3 below, E in general formula (N) 1 ~E 5 By specifying the structure of N1 to N16807, which are specific examples of A, the structures of N1 to N16807 are specified. In each row of Table 3, the structures of 343 specific groups are specified together. For example, in the row of N1 to N343, 1 and E 2 is fixed to a hydrogen atom (H), and E 3 ~E 5 The combinations of Q1 to Q343 are specified as N1 to N343 in order. That is, the row of N1 to N343 shows the structures of N1 to N343 specified in Table 2 together in one row. Similarly, in the row of N344 to N686, 1 is a hydrogen atom (H), E 2 is fixed to a deuterium atom (D), and E 3 ~E 5 The combinations Q1 to Q343 are identified as N344 to N686 in order. The same process is used to identify the rows from N687 to N1029 onwards. [Table 3]

[0035] Next, A in general formula (1) is C(R 15 )(R 16 Specific examples of the linking group represented by formula (C) are shown below. General formula (C) [ka]

[0036] E in general formula (C) 1 ~E 10 Each independently represents a hydrogen atom, a deuterium atom, or a substituent. * represents a bonding site. The substituent may be selected from the above substitution candidate group A, may be selected from the above substitution candidate group B, may be selected from the above substitution candidate group C, may be selected from the above substitution candidate group D, or may be selected from the above substitution candidate group E. In one aspect of the present invention, E 1 ~E 10 are each independently a hydrogen atom (H), a deuterium atom (D), or any of the above Y1 to Y5. Specific examples of the linking group represented by general formula (C) are shown in Tables 4 and 5 below. In Table 4, E in general formula (C) 1 ~E 10 By specifying the structure of C1 to C33614, which are specific examples of A, the structures of C1 to C33614 are specified. In each row of Table 4, the structures of 343 specific groups are specified together. For example, in the row of C1 to C343, 1 and E 2 and E 6 ~E 10 is fixed to a hydrogen atom (H), and E 3 ~E 5 The combinations Q1 to Q343 are identified as C1 to C343 in order. Q1 to Q343 are combinations identified in Table 1 above. Similarly, in the row of C344 to C686, 1 and E 6 ~E 10is a hydrogen atom (H), E 2 is fixed to a deuterium atom (D), and E 3 ~E 5 The combinations Q1 to Q343 are identified as C344 to C686 in order. The same procedure is used for each row of Table 4 from C687 to C1029 onwards. In Table 5, E 1 and E 6 are identical, and E 2 and E 7 are identical, and E 3 and E 8 are identical, and E 4 and E 9 are identical, and E 5 and E 10 The linking groups of general formula (C) are identical. 6 ~E 10 are E in order. 1 ~E 5 Therefore, in Table 5, E 1 ~E 5 For example, in the section C33615 to C33957, E 1 and E 2 and E 6 and E 7 is fixed to a hydrogen atom (H), and E 3 ~E 5 The combination is Q1 to Q343, and E 8 ~E 10 are E 3 ~E 5 The same items are identified as C33615 to C33957 in order. The same method is used to identify the items C33958 to C34300 and subsequent rows of Table 5. [Table 4] [Table 5]

[0037] Next, A in general formula (1) is Si(R 17 )(R 18 Specific examples of the linking group represented by general formula (Si) are shown below. General formula (Si) [ka]

[0038] E in general formula (Si) 1 ~E 10 each independently represents a hydrogen atom, a deuterium atom, or a substituent. * represents a bonding site. The substituent may be selected from the above substitution candidate group A, may be selected from the above substitution candidate group B, may be selected from the above substitution candidate group C, may be selected from the above substitution candidate group D, or may be selected from the above substitution candidate group E. In one aspect of the present invention, E 1 ~E 10 are each independently a hydrogen atom (H), a deuterium atom (D), or any of the above Y1 to Y5. Specific examples of the linking group represented by general formula (Si) are shown in Tables 6 and 7 below. In Table 6, E in general formula (C) 1 ~E 10 By specifying the structure of Si1 to Si33614, which are specific examples of A, the structures of Si1 to Si33614 are specified. In each row of Table 6, the structures of 343 specific groups are specified together. For example, in the rows of Si1 to Si343, 1 and E 2 and E 6 ~E 10 is fixed to a hydrogen atom (H), and E 3 ~E 5 The combinations Q1 to Q343 are identified as Si1 to Si343 in order. Q1 to Q343 are the combinations identified in Table 1 above. Similarly, in the row Si344 to Si686, E 1 and E 6 ~E 10 is a hydrogen atom (H), E 2 is fixed to a deuterium atom (D), and E 3 ~E 5 The combinations Q1 to Q343 are identified as Si344 to Si686 in order. The same is true for each row in Table 6 from Si687 to Si1029 onwards. In Table 7, E 1 and E 6are identical, and E 2 and E 7 are identical, and E 3 and E 8 are identical, and E 4 and E 9 are identical, and E 5 and E 10 The linking groups of general formula (Si) are specified to be identical. 6 ~E 10 are E in order. 1 ~E 5 Therefore, in Table 7, E 1 ~E 5 For example, in the Si33615 to Si33957 stage, E 1 and E 2 and E 6 and E 7 is fixed to a hydrogen atom (H), and E 3 ~E 5 The combination is Q1 to Q343, and E 8 ~E 10 are E 3 ~E 5 The same is true for Si33958 to Si34300 and subsequent rows in Table 7. [Table 6] [Table 7]

[0039] Specific examples of the compound represented by general formula (1) are given below. Here, X, A, and R of the compound represented by the following general formula (1b) are shown. 1 ~R 11 , R 1’ ~ R 7’ , R 9’ , R 11’ , R 12’ The structure of each compound is specified by specifying the structure in Tables 8 to 12. In the tables below, H represents a hydrogen atom, and D represents a deuterium atom. For example, in the columns of Compounds B1-1 to B1-16807 in Table 8, R1 ~R 11 , R 1’ ~ R 7’ , R 9’ , R 11’ , R 12’ is fixed to a hydrogen atom (H), X is fixed to a boron atom (B), and A is N1 to N16807, are specified as Compounds B1-1 to B1-16807 in that order. The other stages are specified in the same manner. Note that the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. General formula (1b) [ka] [Table 8] [Table 9] [Table 10] [Table 11] [Table 12]

[0040] Compound B1-16808~Compound B1-285719, Compound A1-16808~Compound A1-285719, Compound P1-16808~Compound P1-285719, Compound B2-2~Compound B2-17, Compound A2 -2~Compound A2-17, Compound P2-2~Compound P2-17, Compound B3-2~Compound B3-17, Compound A3-2~Compound A3-17, Compound P3-2~Compound P3-17, Compound B4-50422~Compound B4 Compounds in which all hydrogen atoms in each of the compounds, Compound A4-50422 to Compound A4-857157, Compound P4-50422 to Compound P4-857157, Compound B5-50422 to Compound B5-857157, Compound A5-50422 to Compound A5-857157, and Compound P5-50422 to Compound P5-857157, are replaced with deuterium atoms and are designated Compounds B1-16808(D) to B1-285719(D), Compound A1-16808(D)~Compound A1-285719(D), Compound P1-16808(D)~Compound P1-285719(D), Compound B2-2(D)~Compound B2-17(D), Compound A2-2(D)~ Compound A2-17(D), Compound P2-2(D) to Compound P2-17(D), Compound B3-2(D) to Compound B3-17(D), Compound A3-2(D) to Compound A3-17(D), Compound P3-2(D) to Compound P3- 17(D), Compound B4-50422(D) ~ Compound B4-857157(D), Compound A4-50422(D) ~ Compound A4-857157(D), Compound P4-50422(D) ~ Compound P4-857157(D ), compound B5-50422(D) to compound B5-857157(D), compound A5-50422(D) to compound A5-857157(D), and compound P5-50422(D) to compound P5-857157(D).

[0041] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0042] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0043] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0044] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0045] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0046] Examples of preferred compounds represented by general formula (1) are listed below. [ka]

[0047] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by vapor deposition, the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply the coating method to, and is also easy to purify to increase its purity.

[0048] Compounds represented by general formula (1), particularly compounds represented by general formula (1a), are useful as light-emitting materials. Therefore, organic light-emitting devices can be manufactured using compounds represented by general formula (1), particularly compounds represented by general formula (1a). Organic light-emitting devices using compounds represented by general formula (1), particularly compounds represented by general formula (1a), are characterized by excellent device durability and long device life. For example, compared to organic light-emitting devices using compounds having a structure in which the pyrimidine ring in general formula (1a) is replaced with a pyrazine ring, organic light-emitting devices using compounds represented by general formula (1a) have the unexpected effect of longer device life. Furthermore, organic light-emitting devices using compounds represented by general formula (1), particularly compounds represented by general formula (1a), tend to have low initial driving voltages. Furthermore, compounds represented by general formula (1), particularly compounds represented by general formula (1a), can be effectively used in organic optical semiconductor devices.

[0049] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be pre-existed in the structure represented by general formula (1), and the polymer obtained by polymerizing the polymerizable group may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with other monomers to obtain a polymer having repeating units, and the polymer may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled to obtain dimers or trimers, and these may be used as light-emitting materials.

[0050] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas. [ka]

[0051] In the above general formula, Q represents a group containing a structure represented by general formula (1), and L 1 and L 2 represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X 11 -L 11 Preferably, X has a structure represented by the formula: 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. 11 represents a linking group, which is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represents a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and still more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L 1 and L 2 The linking group represented by the following formula can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0052] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0053] A polymer having repeating units containing these formulae can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group. [ka]

[0054] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may be of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene, can be mentioned.

[0055] In some embodiments, the compound represented by general formula (1) is a light-emitting material. Compounds represented by general formula (1) include compounds with long luminescence lifetimes. Compounds represented by general formula (1) can improve luminescence characteristics when used in organic light-emitting devices. For example, compounds represented by general formula (1) include compounds that can extend the device lifetime when used in organic light-emitting devices. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. Compounds represented by general formula (1) include compounds having a high proportion of delayed fluorescent components. For example, the compounds include compounds in which 80% or more of the total emission is the delayed fluorescent component, for example, compounds in which 90% or more of the total emission is the delayed fluorescent component. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) are capable of emitting light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0056] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, the Hartree-Fock equations can be solved using time-dependent density functional theory (TD-DFT / B3LYP / 6-31G*) with a basis set of functions known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals to screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, the donor moiety ("D") can be selected for its HOMO energy (e.g., ionization potential) of, for example, -6.5 eV or greater, and the acceptor moiety ("A") can be selected for its LUMO energy (e.g., electron affinity) of, for example, -0.5 eV or less. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that tightly restricts the acceptor and donor moieties to specific configurations. In some embodiments, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. Delta E below a certain value ST value 4. Quantum yield above a certain value 5.HOMO level 6.LUMO level In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0057] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, the compound represented by general formula (1) can be synthesized using a known coupling reaction. The compound represented by general formula (1) can also be synthesized using a known ring-closing reaction. The compound represented by general formula (1) can also be synthesized using a known substitution reaction. For details of the reaction conditions, please refer to the synthesis examples described below.

[0058] [Constructs using compounds represented by general formula (1)] In some embodiments, a compound represented by Formula (1) is used with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer. The one or more materials may be combined with, dispersed in, covalently bonded to, coated on, supported by, or associated with the compound represented by Formula (1). For example, a compound represented by Formula (1) may be combined with an electroactive material to form a film. In some cases, a compound represented by Formula (1) may be combined with a hole transporting polymer. In some cases, a compound represented by Formula (1) may be combined with an electron transporting polymer. In some cases, a compound represented by Formula (1) may be combined with a hole transporting polymer and an electron transporting polymer. In some cases, a compound represented by Formula (1) may be combined with a copolymer having both a hole transporting moiety and an electron transporting moiety. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compound represented by Formula (1).

[0059] [Film formation] In one embodiment, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing a compound represented by general formula (1) is applied to a surface, and a film is formed after removing the solvent. Wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing a compound represented by general formula (1) is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing a compound represented by general formula (1) can be formed by a dry process. In some embodiments, a vacuum deposition process can be used as the dry process, but is not limited thereto. When using a vacuum deposition process, the compounds constituting the film can be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders can be used, a compressed compact of the mixed powder can be used, or a mixture of the compounds can be used by heating, melting, and cooling the mixture. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are identical or nearly identical, thereby forming a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film with a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the deposition source as a deposition source. In some embodiments, the temperature at which each compound to be co-deposited has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0060] [Organic optical semiconductor element] By using a compound represented by general formula (1), an organic optical semiconductor device with excellent performance can be fabricated. The organic optical semiconductor device may be an organic light-emitting device that emits light, an organic light-receiving device that receives light, or a device that causes light-induced energy transfer within the device. In some embodiments of the present invention, an organic electroluminescence device can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a CMOS (complementary metal oxide semiconductor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). The compound represented by the general formula (1) is useful as a material for organic light-emitting devices, and is particularly preferably used for organic light-emitting diodes. Organic Light-Emitting Diode: One aspect of the present invention relates to the use of a compound represented by general formula (1) of the present invention as an emitting material in an organic light-emitting device. In one embodiment, the compound represented by general formula (1) of the present invention can be effectively used as an emitting material in the emitting layer of an organic light-emitting device. In one embodiment, the compound represented by general formula (1) includes a delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In one embodiment, the compound represented by general formula (1) is used for phosphorescence-sensitized fluorescence. In one embodiment, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In one embodiment, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescent material. In one embodiment, the compound represented by general formula (1) can be used as a host material and can be used together with one or more emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF materials (delayed fluorescent materials). In one embodiment, the compound represented by general formula (1) can also be used as a hole-transporting material. In one embodiment, the compound represented by general formula (1) can be used as an electron-transporting material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device including the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer comprises a compound represented by Formula (1), and the compound represented by Formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by Formula (1) relative to the film-forming surface influences or dictates the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by Formula (1) improves light extraction efficiency from the light-emitting layer. One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes an emitting layer. In one embodiment, the emitting layer includes a compound represented by general formula (1) as an emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of another emitting material included in the emitting layer (as a so-called assist dopant). The other emitting material may be a fluorescent material or a phosphorescent material. In one embodiment, the compound represented by general formula (1) included in the emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material included in the emitting layer and the lowest excited singlet energy level of the other emitting material included in the emitting layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an light-emitting layer. In some embodiments, the organic layer includes only an light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with hole injection functionality, and the electron transport layer may be an electron injection transport layer with electron injection functionality.

[0061] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has singlet and triplet excited energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. That is, any host material that can achieve high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF material and a host material are used. In some embodiments, the TADF material is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer. In one embodiment, the organic electroluminescent device has a layer containing a compound represented by general formula (1). In one embodiment, the layer also contains a host material. In one embodiment, the layer containing the compound represented by general formula (1) and the host material also contains a delayed fluorescent material having a structure outside the range of general formula (1), and the delayed fluorescent material has a lowest excited singlet energy lower than that of the host material and higher than that of the compound represented by general formula (1). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent device has a layer containing the compound represented by general formula (1) and an emitting material having a structure outside the range of general formula (1) (this layer may further contain a host material). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the emitting material having a structure outside the range of general formula (1) is maximized. In addition, in this case, in one embodiment, the amount of light emitted from the emitting material having a structure outside the range of general formula (1) is greater than the amount of light emitted from the compound of general formula (1).

[0062] When the compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. Furthermore, these exemplary skeletons may be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.

[0063] [ka] JPEG2025159576000034.jpg223159JPEG2025159576000035.jpg255169

[0064] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be used as light-emitting materials used together with the assist dopant having the structure represented by general formula (1).

[0065] Further examples of the light-emitting material include compounds represented by the following general formula (F1). General formula (F1) [ka]

[0066] In general formula (F1), R 1 , R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 2 represents an acceptor group, or R 1 and R 2 are bonded to each other to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R14 and R 15 , R 15 and R 16 may be bonded to each other to form a cyclic structure. 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of the groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0067] In one aspect of the present invention, X 2 When is O or NR, R 7 is an acceptor group or R 6 and R 7 are bonded to each other to form an acceptor group, or R 7 and R 8 are bonded to each other to form an acceptor group. 3 When is O or NR, R 10 is an acceptor group or R 9 and R 10 are bonded to each other to form an acceptor group, or R 10 and R 11 are bonded to each other to form an acceptor group. 4 When is O or NR, R 15 is an acceptor group or R14 and R 15 are bonded to each other to form an acceptor group, or R 15 and R 16 are bonded to each other to form an acceptor group. 2 is NR, R is a substituted or unsubstituted phenyl group, and R 8 In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. 3 is NR, R is a substituted or unsubstituted phenyl group, and R 9 In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. 4 is NR, R is a substituted or unsubstituted phenyl group, and R 16 In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. 1 is NR, R is a substituted or unsubstituted phenyl group, and R 1 When a carbazole ring is formed by directly bonding to the carbon atom to which the phenyl group is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is on the phenyl group). In one embodiment of the present invention, the compound is represented by the following general formula (F2). General formula (F2) [ka]

[0068] In general formula (F2), R 1 , R 3 , R 6 ~R 11 , R 14 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent.2 represents an acceptor group, or R 1 and R 2 are bonded to each other to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 14 and R 15 , R 15 and R 16 may be bonded to each other to form a cyclic structure. 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of the groups is O or NR, and the remaining groups may be O or NR or may not be linked. When they are not linked, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2 Each of the groups independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 , C.R. 3 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0069] Further examples of the light-emitting material include compounds represented by the following general formula (F3). General formula (F3) [ka]

[0070] In general formula (F3), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 1 may be bonded to each other to form a cyclic structure. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0071] In one aspect of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. 3 and R 10 are each independently a substituted amino group. 1 and R 3 , and ,R 2 and R 10 In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0072] Further examples of the light-emitting material include compounds represented by the following general formula (F4). General formula (F4) [ka]

[0073] In general formula (F4), Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 1 ~R 9 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 may be bonded to each other to form a cyclic structure, provided that Z 1 , Z 2 , R 1 and R 2 are bonded to each other to form a ring, R 2 and R 3 are bonded to each other to form a ring, R 4 and R5 The ring formed by bonding together, and R 5 and R 6 at least one of the rings formed by bonding to each other is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R 1 ~R 9 at least one of Z is a substituted or unsubstituted aryl group or an acceptor group; 1 and Z 2 At least one of the rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 1 , C.R. 2 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0074] In one aspect of the present invention, Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. 1 ~R 9 are each independently a substituted or unsubstituted aryl group or an acceptor group, or R 1 and R 2 are bonded to each other to form a ring, R 2 and R 3 are bonded to each other to form a ring, R 4 and R 5 The ring formed by bonding together, and R 5 and R 6and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. 8 is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0075] Further examples of the light-emitting material include compounds having a fused ring structure A (in which a hydrogen atom may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring. Structure α [ka]

[0076] In the structure α, X 1 and X 2 each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, and Z and X 2 may be bonded to each other to form a cyclic structure. In the fused ring structure A, the structure fused to b and X 1 , b and Z, Z and X2 may be bonded to each other to form a cyclic structure.

[0077] Further examples of the light-emitting material include compounds represented by the following general formula (F5). General formula (F5) [ka]

[0078] In general formula (F5), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0079] Further examples of the light-emitting material include compounds represented by the following general formula (F6). General formula (F6) [ka]

[0080] In general formula (F6), X 3 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 4 ~R 7 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0081] Further examples of the light-emitting material include compounds represented by the following general formula (F7). General formula (F7) [ka]

[0082] In general formula (F7), X 4 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 4a ~R 7a represents a hydrogen atom, a deuterium atom or a substituent, and R2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 , R 4a and R 5a , R 5a and R 6a , R 6a and R 7a , R 7a and R 1 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0083] Further examples of the light-emitting material include compounds represented by the following general formula (F8). General formula (F8) [ka]

[0084] In general formula (F8), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and Z 3 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 8 ~R 14 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 8 and R 9 , R9 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 Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure.

[0085] Further examples of the light-emitting material include compounds represented by the following general formula (F9). General formula (F9) [ka]

[0086] In general formula (F9), Z 1 and Z 4 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 15 ~R 17 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure.

[0087] Further examples of the light-emitting material include compounds represented by the following general formula (F10). General formula (F10) [ka]

[0088] In general formula (F10), Z 1 and Z 5 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , Z 3 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0089] Further examples of the light-emitting material include compounds represented by the following general formula (F11). General formula (F11) [ka]

[0090] In general formula (F11), Z 1represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 21 ~R 27 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 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 , R 26 and R 27 may be bonded to each other to form a cyclic structure.

[0091] Further examples of the light-emitting material include compounds represented by the following general formula (F12). General formula (F12) [ka]

[0092] In general formula (F12), Z 1 and Z 6 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 28 ~R30 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and Z 6 may be bonded to each other to form a cyclic structure.

[0093] Further examples of the light-emitting material include compounds represented by the following general formula (F13). General formula (F13) [ka]

[0094] In general formula (F13), Z 1 and Z 7 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring, and R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2and Z 7 , Z 7 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0095] Further examples of the light-emitting material include compounds represented by the following general formula (F14). General formula (F14) [ka]

[0096] In general formula (F14), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 31 ~R 44 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 may be bonded to each other to form a cyclic structure.

[0097] Further examples of the light-emitting material include compounds represented by the following general formula (F15). General formula (F15) [ka]

[0098] In general formula (F15), Z 1 and Z 8 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 51 ~R 60 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , R 60 and Z 8 may be bonded to each other to form a cyclic structure.

[0099] Further examples of the light-emitting material include compounds represented by the following general formula (F16). General formula (F16) [ka]

[0100] In general formula (F16), Z 1 , Z 8 and Z 9each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 61 ~R 66 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , R 66 and Z 8 may be bonded to each other to form a cyclic structure.

[0101] Further examples of the light-emitting material include compounds represented by the following general formula (F17). General formula (F17) [ka]

[0102] In general formula (F17), Z 1 , Z 9 and Z 10 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 67 ~R 69 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 70 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , Z 9 and R 67 , R 67 and R68 , R 68 and R 69 , R 69 and Z 10 , Z 10 and R 70 may be bonded to each other to form a cyclic structure.

[0103] Further examples of the light-emitting material include compounds represented by the following general formula (F18). General formula (F18) [ka]

[0104] (In general formula (F18), Z 1 , Z 11 and Z 12 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 72 ~R 74 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 71 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and Z 74 , R 74 and Z 12 may be bonded to each other to form a cyclic structure.

[0105] Further examples of the light-emitting material include compounds represented by the following general formula (F19). General formula (F19) [ka]

[0106] In general formula (F19), Z 1 and Z 11 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 76 ~R 82 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , R 81 and R 82 may be bonded to each other to form a cyclic structure.

[0107] Further examples of the light-emitting material include compounds represented by the following general formula (F20). General formula (F20) [ka]

[0108] In general formula (F20), X 5 represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded, and R 101 ~R 130 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 101 and R 102 , R 102and R 103 , R 103 and R 104 , R 104 and R 105 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 109 and R 110 , R 110 and R 111 , R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 114 and R 115 , R 115 and R 116 , R 116 and R 117 , R 117 and R 118 , R 118 and R 119 , R 119 and R 120 , R 120 and R 121 , R 121 and R 122 , R 122 and R 123 , R 123 and R 124 , R 124 and R 125 , R 125 and R 126 , R 126 and R 127 , R 127 and R 128 , R 128 and R 129 , R 129 and R 130 , R 130 and R 101 may be bonded to each other to form a cyclic structure.

[0109] Further examples of the light-emitting material include compounds represented by the following general formula (F21). General formula (F21) [ka]

[0110] In general formula (F21), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R 3 ~R 9 each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that R 1 , R 2 , Z 1 and Z 2 At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , Z 2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R.8 , C.R. 9 may be substituted with N.

[0111] In one aspect of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. 1 and Z 1 are bonded to each other to form a ring structure. 1 and Z 1 are bonded to each other to form a pyrrole ring.

[0112] Further examples of the light-emitting material include compounds represented by the following general formula (F22). General formula (F22) [ka]

[0113] In general formula (F22), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side. 1 ~R 26 , A 1 , A 2 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure. 1 is a nitrogen atom, R 17 and R 18 are bonded to each other as a single bond to form a pyrrole ring, and X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R18 When they are bonded to each other to form a single bond, R 1 ~R 6 At least one of R is a substituted or unsubstituted aryl group, or 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 are bonded to each other to form an aromatic hydrocarbon ring or a heteroaromatic ring. For a detailed description of the compound represented by general formula (F22), a preferred range, and specific examples thereof, see

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification.

[0114] In one embodiment, when a host material is used, the amount of the compound used in the present invention as the luminescent material contained in the luminescent layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as the luminescent material contained in the luminescent layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as the luminescent material contained in the luminescent layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as the luminescent material contained in the luminescent layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as the luminescent material contained in the luminescent layer is 10% by weight or less. In some embodiments, the host material of the light-emitting layer is an organic compound that has hole-transporting and electron-transporting functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0115] In some embodiments, the host material is selected from the group consisting of: [ka] In one embodiment, the light-emitting layer contains two or more TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are highest in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. STis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the photo-excited luminescence quantum yield φPL1(A) of a co-deposited film of the first TADF molecules and the host material (where the concentration of the first TADF molecules in the co-deposited film is A wt %) and the photo-excited luminescence quantum yield φPL2(A) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photo-excited luminescence quantum yield φPL2(B) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is B wt %) and the photo-excited luminescence quantum yield φPL2(100) of a film of the second TADF molecules alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the light-emitting layer can contain three structurally different TADF molecules. The compound of general formula (1) can be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of general formula (1), the TADF material may be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011955, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 081088, and ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of JP 2013-256490 A, paragraphs 0008~0020 and 0038~0040 of JP 2013-116975 A, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359 A, paragraph 0 of WO2013 / 161437 A 008 to 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of JP 2014-9352 A, paragraphs 0008 to 0048 and 0067 to 0076 of JP 2014-9224 A, paragraphs 0013 to 0025 of JP 2017-119663 A, paragraphs 0013 to 0026 of JP 2017-119664 A, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly exemplary compounds, that are capable of emitting delayed fluorescence are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO2013 / 133359 A, WO2014 / 034535 A, WO2014 / 115743 A, WO2014 / 122895 A, WO2014 / 126200 A, WO2014 / 136758 A, WO2014 / 133121 A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0116] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0117] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, and the substrate is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0118] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or greater). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as In2O3-ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly precise (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material, such as an organic conductive compound, can be applied, a wet film formation method, such as a printing method or a coating method, is used. In some embodiments, the anode has a transmittance of greater than 10% when emitted light passes through it, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0119] cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, one of the anode and cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode. In some embodiments, a device includes an anode and a cathode, both of which are transparent or semi-transparent.

[0120] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as hole injection materials are listed below.

[0121] [ka]

[0122] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0123] Barrier layer: A blocking layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a blocking layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functionality of an electron blocking layer and the functionality of an exciton blocking layer.

[0124] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are listed below.

[0125] [ka]

[0126] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0127] [ka] JPEG2025159576000065.jpg45170

[0128] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer may be adjacent to only one of the anode side or the cathode side of the light-emitting layer, or one exciton blocking layer may be adjacent to the anode side of the light-emitting layer and another exciton blocking layer may be adjacent to the cathode side of the light-emitting layer. In some embodiments, when the exciton blocking layer is present on the anode side, it may be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer has 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 emissive material.

[0129] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0130] [ka]

[0131] Electron transport layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0132] [ka]

[0133] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0134] [ka]

[0135] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0136] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within devices and / or as hole transport materials, such as organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0137] Bulb or Lamp: In some embodiments, the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device comprises: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0138] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition onto the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within the pixel area protects etching in specific regions until these specific patterns are undercut and removed from the substrate. At that point, all pixel areas are subjected to similar etch rates, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within the pixel, enabling the deep, localized etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar, a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable, low-cost method for forming open areas in the deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0139] Device manufacturing method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0140] In another aspect of the present invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and the edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be softly cut into individual cell panels. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed simultaneously with the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0141] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming the barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0142] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at an interval with each of the multiple display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0143] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0144] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer (an inorganic film) and a planarization film (an organic film) are disposed on and cover the TFT layer. At the same time as the planarization film (e.g., polyimide or acrylic) is formed, the grooves at the interface are covered with an organic film (e.g., polyimide or acrylic). This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impacts that may occur. That is, if all barrier layers were completely exposed without the organic film, the impacts would be transmitted to the barrier layers when each cell panel was cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impacts that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers. In one embodiment, the organic film and the planarizing film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarizing film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarizing film and the remaining portion of the organic film, so the organic film and the planarizing film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0145] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, 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 mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, this can prevent cracks from occurring in the barrier layer during cutting. In some embodiments, the method reduces product rejection rates and stabilizes product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. [Example]

[0146] The following synthesis examples and working examples will further illustrate the features of the present invention. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334).

[0147] (Synthesis Example 1) Synthesis of Compound A [ka]

[0148] Intermediate a Under a nitrogen stream, a tetrahydrofuran solution (490 mL) of 2-bromo-9H-carbazole (40 g, 162 mmol), bis(4-tert-butylphenyl)amine (50 g, 178 mmol), tris(dibenzylideneacetone)palladium (741 mg, 0.80 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.17 g, 4.05 mmol), and lithium bis(trimethylsilyl)amide (278 mL, 356 mmol) was stirred at 65 °C for 18 hours. The reaction mixture was filtered, and the filtrate was concentrated. The residue was dissolved in chloroform and filtered again. The filtrate was purified by silica gel column chromatography (ethyl acetate / hexane = 2 / 8) to give intermediate a (21.82 g, 48.8 mmol, 30% yield) as a white solid.

[0149] [ka]

[0150] Intermediate b Under a nitrogen stream, a solution of intermediate a (21.82 g, 48.8 mmol), 1,4-dibromo-2,5-difluorobenzene (12.0 g, 44.3 mmol), 3,6-di-tert-butylcarbazole (11.1 g, 39.9 mmol), and potassium phosphate (28.2 g, 133 mmol) in N,N-dimethylformamide (221 mL) was stirred at 160 °C for 16 hours. After the reaction was completed, the mixture was cooled to 0 °C, and the precipitated crystals were removed by filtration. Methanol was added to the filtrate to precipitate crystals, which were then filtered. The filtered crystals were purified by silica gel column chromatography (dichloromethane:hexane = 2:8) to obtain intermediate b (9.9 g, 10.3 mmol, 21% yield) as a white solid.

[0151] [ka]

[0152] Compound A Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 19.3 mL, 30.9 mmol) was added to a xylene solution (515 mL) of intermediate b (9.9 g, 10.3 mmol) at 60 °C and stirred for 2 hours. The reaction mixture was cooled to -80 °C, boron tribromide (2.94 mL, 30.9 mmol) was added, and the mixture was warmed to room temperature and stirred for 30 minutes. After that, N,N-diisopropylethylamine (5.37 mL, 30.9 mmol) was added and refluxed for 16 hours. The reaction mixture was cooled to room temperature, and the prepared tetrahydrofuran solution (34.3 mL) of 2,4,6-triisopropylphenylmagnesium bromide (48.4 mmol) was added and stirred for an additional 17 hours. The mixture was filtered through Celite and silica, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (dichloromethane:hexane), and the concentrated residue was dispersed in methanol and filtered to obtain a yellow solid compound A (0.3 g, 0.294 mmol, yield 3%). Compound A corresponds to compound B1-151460 in Table 8.

[0153] (Example 1) Preparation and evaluation of thin films Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Compound A was evaporated under conditions of less than 10 Pa to form a thin film consisting of only Compound A to a thickness of 100 nm, which was used as the neat thin film of Example 1. Separately, a thin film was evaporated on a quartz substrate by vacuum evaporation under conditions of a vacuum degree of 1×10 -3 Compound A and H1 were evaporated from different evaporation sources under conditions of less than Pa to form a thin film with a thickness of 100 nm and a concentration of compound A of 20 wt %. This was used as the doped thin film of Example 1. The HOMO and LUMO energies were measured using the formed neat thin film. When the formed doped thin film was irradiated with 300 nm excitation light, delayed fluorescence was observed. The results of measuring the emission peak wavelength are shown in the table below, along with the measurement results of the HOMO and LUMO energies.

[0154] [Table 13] [ka]

[0155] (Example 2) Fabrication and evaluation of organic electroluminescence device Each thin film was deposited by vacuum deposition on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 100 nm, at a vacuum of 1×10 -6 The layers were laminated using a Pa. First, HATCN was formed on ITO to a thickness of 10 nm, and NPD was formed thereon to a thickness of 30 nm. Next, TrisPCz was formed thereon to a thickness of 10 nm, and H1 was further formed thereon to a thickness of 5 nm. Next, Compound A and H1 were co-deposited from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the concentration of Compound A was 35 wt %. SF3TRZ was formed thereon to a thickness of 10 nm, and SF3TRZ and Liq were further co-deposited thereon from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the SF3TRZ:Liq (weight ratio) was 7:3. Next, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode. By the above procedure, the organic electroluminescent device of Example 1 was fabricated. When a current was applied to the fabricated organic electroluminescence device, delayed fluorescence was observed. The maximum amount of light emitted from the device was from Compound A.

[0156] (Example 3) Fabrication and evaluation of organic electroluminescence device An organic electroluminescence device was fabricated using the same procedure as in Example 2, except that the light-emitting layer in Example 2 was formed by co-evaporating TADF1, compound A, and H1 from different evaporation sources to form a light-emitting layer with a thickness of 30 nm. In Example 3, the concentration of TADF1 in the light-emitting layer was 34 wt %, the concentration of compound A was 1 wt %, and the concentration of H1 was 65 wt %. When a current was applied to the fabricated organic electroluminescence device, delayed fluorescence was observed. The maximum amount of light emitted from the device was from Compound A.

[0157] [ka] [Industrial Applicability]

[0158] By using the compound represented by general formula (1), it is possible to provide an organic optical semiconductor device such as an organic light-emitting device having good characteristics, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) 【Chemical 1】 [In general formula (1), Each X represents B, Al or P. Y is N(R １４ ), O or S. A is N(R １４ ), O, S, C(R １５ ) (R １６ ) or Si(R １７ ) (R １８ ) represents R Ａ and R Ａ’ are each independently a hydrogen atom, a deuterium atom, or N(R １４ ), OH, SH, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or forms a condensed ring when linked to other atoms. R Ｂ ~R Ｄ and R Ｂ’ ~R Ｄ’ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or is linked to other atoms to form a condensed ring. Ｂ’ and R Ｃ’ do not bond to each other to form a fused ring. R １４ ~R １８ each independently represents a hydrogen atom, a deuterium atom, or a substituent, or is linked to another atom to form a fused ring.

2. R Ｄ and R Ｄ’ The compound of claim 1 , wherein is not linked to another atom to form a fused ring.

3. Y is N(R １４ 2. The compound of claim 1, wherein

4. The compound according to claim 3, which is represented by the following general formula (1a): General formula (1a) 【Chemistry 2】 [In general formula (1a), Each X represents B, Al or P. A is N(R １４ ), O, S, C(R １５ ) (R １６ ) or Si(R １７ ) (R １８ ) represents Z and Z′ each independently represent a single bond, C(R １５ ) (R １６ ), O, S or Si(R １７ ) (R １８ ) represents R １ ~R １１ and R １’ ~R １３’ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or is linked to other atoms to form a condensed ring. １２’ and R １３’ do not bond to each other to form a fused ring. R １４ ~R １８ each independently represents a hydrogen atom, a deuterium atom, or a substituent, or is linked to another atom to form a fused ring.

5. The compound according to claim 4 , wherein each X is B.

6. A is N (R １４ 5. The compound of claim 4, wherein

7. A is C (R １５ ) (R １６ 5. The compound of claim 4, wherein

8. The compound of claim 4 wherein A is O.

9. 5. The compound of claim 4, wherein Z and Z' are both single bonds.

10. The compound of claim 4, wherein Z and Z' are the same.

11. R ３ , R ７ , R ９ , R ３’ and R ６’ The compound according to claim 1, wherein at least one of the groups is a substituted or unsubstituted alkyl group.

12. A light-emitting material comprising the compound according to any one of claims 1 to 11.

13. A film comprising a compound according to any one of claims 1 to 11.

14. An organic optical semiconductor device comprising the compound according to any one of claims 1 to 11.

15. The organic optical semiconductor device according to claim 14, which is an organic light-emitting device.

16. 16. The organic optical semiconductor device according to claim 15, which is an organic electroluminescence device.

17. 17. The organic optical semiconductor device of claim 16, wherein the organic electroluminescent device has a layer comprising the compound, the layer also comprising a host material.

18. 18. The organic optical semiconductor element according to claim 17, wherein the layer further comprises a delayed fluorescent material having a structure outside the scope of the general formula (1) in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

19. 19. The organic optical semiconductor device according to claim 18, wherein the compound emits the greatest amount of light among materials contained in the organic electroluminescence device.

20. 17. The organic optical semiconductor device according to claim 16, wherein the organic electroluminescence device has a layer containing the compound, and the layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

21. The organic optical semiconductor device according to claim 20 , wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

22. The organic optical semiconductor device according to claim 15, which emits delayed fluorescence.

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