Compound, light-emitting material, and organic light-

Abstract

To provide a compound exhibiting a multiple resonance effect and having luminescent characteristics excellent in practicality.SOLUTION: The compound is represented by general formula (1). In the formula, one of X1 and X2 is N and the other is B, and R1 to R26, A1, and A2 are H or substituents.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound having good luminescence properties. The present invention also relates to a light-emitting material and an organic light-emitting device. [Background technology]

[0002] Active research into improving the luminous efficiency of organic light-emitting devices such as organic light-emitting diodes (OLEDs) It is being carried out. For example, Non-Patent Document 1 discloses 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phena By using compounds that exhibit multiple resonance effects, such as zaborine (DABNA-1), It exhibits thermally activated delayed fluorescence due to the reverse intersystem crossing process, resulting in emission with a narrow half-width and high color purity. Such light emission can achieve high luminous efficiency. This makes them useful in display-oriented applications. In addition, Non-Patent Documents 1 and 2 report that modifying DABNA-1 increases the maximum transition rate. Adjusting energy levels such as homogeneous molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) It also promotes the fluorescence emission process and reverse intersystem crossing process that contribute to light emission, resulting in electroluminescence. It is described that the emission quantum efficiency is improved. [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] Various studies have been conducted on compounds that exhibit such multiple resonance effects. There are many unknowns regarding the relationship between the structure and the light-emitting properties. Therefore, it is necessary to provide materials with even slightly better light-emitting properties. Therefore, the present inventors investigated the relationship between the derivatives of compounds that exhibit the multiple resonance effect and their luminescence properties. We have conducted intensive research with the aim of generalizing a structure that exhibits excellent luminescence properties. [Means for solving the problem]

[0005] As a result of intensive research, the present inventors have found that certain compounds exhibiting the multiple resonance effect The present invention is based on this knowledge. This was proposed based on the above observation 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), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side R 1 ~R 26 , A 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent Represents. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R5 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 1 4 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 1 9 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 2 4 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure However, X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form single bonds, and Forming a roll ring, X 2 is a nitrogen atom, R 21 and R 22 are bonded together to form a single bond and form a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 2 1 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 are bonded to each other When a single bond is formed, R 1 ~R 6 At least one of the ants is substituted or unsubstituted. Is it a methyl 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 Noise These are bonded to each other to form an aromatic ring or a heteroaromatic ring. 1 is a boron atom So, X 2 is a nitrogen atom, and R 7 and R 8 , R 17 and R 18 are bonded to each other to form a boron atom When a cyclic structure containing is R 7 and R 8 , R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or -N(R 27 )- is formed. R 27 represents a hydrogen atom, a deuterium atom, or a substituent represent.] [2] X 1 is a nitrogen atom, and X 2 is a boron atom. [3] R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 Of Pairs 1 to 6 are bonded to each other to form a new benzofuran or benzothiophene ring. The compound according to [1] or [2], [4] R 3 and R 6 At least one of [1] to [3] is a substituent. The compound according to any one of claims 1 to 5. [5] R 3 and R 6 and [3] are both substituents. compound. [6] R 3 and R 6 The substituent represented by is selected from the group consisting of alkyl groups and aryl groups. [4] or [5], which is one group selected from the group consisting of 2 or more groups. ] The compound described in [7] R 8 and R12 are both substituents, [1] to [6] In particular, compounds of R 8 and R 12 is an alkyl group having 2 or more carbon atoms, preferably an alkyl group having 3 or more carbon atoms alkyl groups, more preferably alkyl groups having 3 to 8 carbon atoms, and even more preferably alkyl groups having 3 or 4 carbon atoms. A compound that is an alkyl group. [8] The compound according to [1], represented by the following general formula (1a): [ka] [In the general formula (1a), Ar 1 ~Ar 4 each independently represents a substituted or unsubstituted aryl R represents a group, or a substituted or unsubstituted heteroaryl group. 41 and R 42 are, respectively m1 and m2 each independently represent an integer of 0 to 5. n1 and n3 each independently represent an integer of 0 to 4, and n2 and n4 each independently represent an integer of 0 to 4. represents an integer between 0 and 3. 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent At least one of n1 to n4 is 1 or more, and m1 and m2 each independently represent 1 to 5. It is preferable that the integer is one of the following. [9] A 1 and A 2 are each independently a group having a Hammett σp value of greater than 0.2 The compound according to any one of [1] to [8].

[10] A 1 and A 2 and [9] are both cyano groups.

[11] A 1 and A 2 and [9] are both halogen atoms.

[12] The compound according to any one of [1] to

[11] , which has a rotationally symmetric structure.

[13] The compound according to [1], having any one of the following structures: [ka]

[14] A compound having any of the following structures: [ka]

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

[14] .

[16] A film containing the compound according to any one of [1] to

[14] .

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

[14] .

[18] An organic light-emitting device comprising the compound according to any one of [1] to

[14] .

[19] A device having a light-emitting layer containing a host material, a delayed fluorescent material, and the compound.

[18] The organic light-emitting element according to

[18] , wherein the compound emits the largest amount of light among the materials contained therein. child.

[20] The organic light-emitting device according to

[18] or

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

[0007] The compound of the present invention exhibits excellent light-emitting properties. The compound of the present invention can be used as a material for an organic light-emitting device. It is useful. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 2 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescence element. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described in detail below. The present invention may be based on the representative embodiments and specific examples of the present invention. The present invention is not limited to the above embodiments and specific examples. The numerical ranges expressed by "~" include the numbers before and after as the lower and upper limits. In addition, the range includes a part of the hydrogen atoms present in the molecule of the compound used in the present invention. Or all are deuterium atoms ( 2 H, deuterium D). In chemical structural formulas, hydrogen atoms are either represented as H or omitted. When the atoms bonded to the carbon atoms constituting the ring skeleton of the benzene ring are omitted, the display is omitted. In the above description, H is assumed to be bonded to a carbon atom constituting the ring skeleton. The term "substituent" means an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" refers to a group in which a hydrogen atom is replaced with a deuterium atom or a substituent. This means that the ion may be replaced.

[0010] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be explained. General formula (1) [ka]

[0011] In general formula (1), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side In one aspect of the present invention, X 1 is a nitrogen atom, and X 2 is a boron atom. Ki, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring. In one embodiment, X 1 is a boron atom, and X 2 is a nitrogen atom. In this case, R 21 and R 2 2 are bonded to each other to form a single bond to form a pyrrole ring.

[0012] In general formula (1), R 1 ~R 26 , A 1 , A 2 are each independently a hydrogen atom, a deuterium atom represents a group or substituent. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 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 R24 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure. R 7 and R 8 The ring structure formed by bonding of these atoms has a boron atom and four Contains carbon atoms. 17 and R 18 The ring structure formed by bonding is X 1 is a boron atom When X is a cyclic ring, the ring structure contains a boron atom and four carbon atoms. 1 is a nitrogen atom When R is a cyclic ring, the cyclic structure is limited to a pyrrole ring. 21 and R 22 A ring structure formed by bonding The structure is X 2 When is a boron atom, the ring skeleton consists of a boron atom and four carbon atoms. Contains X 2 When R is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded to each other to form a ring structure containing a boron atom In this case, the cyclic structure is preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring. R is more preferably a 6-membered ring, and even more preferably a 6-membered ring. 7 and R 8 , R 17 and R 18 , R 21 and R 22 When they bond to each other, they bond to each other to form a single bond, -O-, -S-, -N(R 2 7 )-, -C(R 28 )(R 29 )-, -Si(R 30 )(R 31)-, -B(R 32 ) -, -CO-, -CS-, -O-, -S- or -N(R 2 7 )-, and more preferably -N(R 27 It is more preferred to form Here, R 27 ~R 32 each independently represents a hydrogen atom, a deuterium atom, or a substituent. As the substituent, a group selected from any one of the following substituent groups A to E may be used. , a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Substituted heteroaryl groups are preferred, particularly R 27 is a substituted or unsubstituted ant R is preferably a methyl group. 27 ~R 32 When is a substituent, R 7 and R 8 But each other R in the ring formed by bonding 27 ~R 32 is R 6 and R 9 binds to at least one of may further form a cyclic structure, and R 17 and R 18 In the ring formed by bonding together RuR 27 ~R 32 is R 16 and R 19 and further form a ring structure by bonding with at least one of the You can also create R 21 and R 22 R in the ring formed by bonding together 27 ~R 32 is R 20 and R 23 may be bonded to at least one of the above to form a ring structure. In one embodiment, R 7 and R 8 , R17 and R 18 , R 21 and R 22 Only one pair of them In one aspect of the invention, R 7 and R 8 , R 17 and R 18 , R 21 and R 22 brain In one embodiment of the present invention, R 7 and R 8 , R 17 and R 18 , R 21 and R 22 All of these are connected to each other.

[0013] R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 1 5 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 2 1 , R 22 and R 23 , R23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded to each other The cyclic structure formed by the above may be an aromatic ring or an aliphatic ring, and may contain a heteroatom. The heteroatom may be a ring having one or more other rings condensed thereto. The atom is selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a pyridine ring, and a pyridazine ring. , pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring benzophenone ring, imidazoline ring, furan ring, thiophene ring, oxazole ring, isoxazole ring , thiazole ring, isothiazole ring, cyclohexadiene ring, cyclohexene ring, cyclo Pentene ring, cycloheptatriene ring, cycloheptadiene ring, cycloheptene ring, and and rings in which one or more rings selected from the group consisting of these rings are further fused. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring (or and the ring may be fused to the ring, and may be substituted with, for example, an alkyl group or an aryl group. In a preferred embodiment of the present invention, the ring structure is an optionally substituted or It is an unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran, a thiophene ring of benzothiophene, It is an off-ring. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 1 4 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 2 0 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 2 6 The number of combinations of these that are bonded to each other to form a cyclic structure may be 0. For example, it may be any one of 1 to 6. For example, it may be any one of 1 to 4, You can select 1, select 2, select 3 or 4. In an embodiment, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded to each other to form a ring In one embodiment of the present invention, R 5 and R 6 are bonded to each other to form a ring structure In one aspect of the present invention, R 9 and R 10 , R 10 and R 11 , R 11 and R 12 from A selected pair are bonded together to form a ring structure. 1 and R 2 , R 13 and R 14 are all bonded to each other to form a cyclic structure. In your opinion, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 A pair selected from the group consisting of It forms a structure and also has R 5 and R 6 are bonded to each other to form a ring structure. In one aspect of the present invention, R 5 and R 6 , R 19 and R 20 are all bonded to each other to form a ring structure It is being formed.

[0014] Adjacent R n (n=1-26) and R that are not bonded to each other 1 ~R 26 is a hydrogen atom, a heavy atom The substituent is a hydrogen atom or a substituent selected from the following substituent groups A to E. Any group selected from the group consisting of methyl, ... R 1 ~R 26 Preferred substituents that can be taken by the alkyl group include substituted or unsubstituted alkyl groups, substituted or unsubstituted alkyl groups, or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, for example, substituted The group may be a substituted or unsubstituted aryl group, for example, the substituents may be substituted or unsubstituted. The alkyl group, aryl group, and heteroaryl group may be substituted. The substituent of the group can be a group selected from any one of the substituent groups A to E. Preferably, it is one or more groups selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group. The above group is more preferably a group of the substituent group E, and may be unsubstituted. In a preferred embodiment, R 1 ~R 6 At least one of the groups is a substituent, and preferably the group E group. For example, R 2 ~R 6 At least one of the groups is a substituent, and preferably the group E groups. For example, R 5 and R 6 At least one of the groups is a substituent, and preferably a substituent. In a preferred embodiment of the present invention, R 3 and R 6 At least one of It is a substituent, more preferably both are substituents, and is preferably a group of Substituent Group E. In a preferred embodiment of the present invention, X 1 is a nitrogen atom, R 15 and R 20 Less One of the substituents is a substituent, more preferably both of the substituents are substituents, and the substituents in the substituent group E are preferably In this case, R 17 and R 18 are bonded to each other to form a single bond. In a preferred embodiment, X 2 is a nitrogen atom, R 19 and R 24 At least one of is a substituent, more preferably both are substituents, and is preferably a group of the substituent group E At this time, R 21 and R 22 are bonded to each other to form a single bond. is R 8 and R 12 At least one of the groups is a substituent, and preferably both are substituents. In one aspect of the present invention, R 8 , R10 and R 12 is a substituent. 8 ~R 12 Substitution of The group is preferably an unsubstituted alkyl group. 8 and R 12 has 2 or more carbon atoms an alkyl group (preferably an alkyl group having 3 or more carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms); When the alkyl group is an alkyl group having 3 or 4 carbon atoms, the orientation of the film is improved. This is preferable because it increases R 8 and R 12 is a substituent (preferably an alkyl group, more preferably Preferably, it is an alkyl group having 2 or more carbon atoms, more preferably an alkyl group having 3 or more carbon atoms, More preferably, it is an alkyl group having 3 to 8 carbon atoms, and particularly preferably an alkyl group having 3 or 4 carbon atoms. ) and R 1 ~R 6 At least one of the substituents (preferably the substituent group E) It is particularly preferred that X is a group. 1 is a boron atom, R 13 and R 17 few At least one of X is a substituent, and preferably both are substituents. 1 is a boron atom, R 13 , R 15 and R 17 is a substituent. X 1 is boron When it is an atom, R 13 ~R 17 The substituent of X is preferably an unsubstituted alkyl group. 2 is a boron atom, R 22 and R 26 At least one of these is a substituent, and In one embodiment of the present invention, X 2 is a boron atom, R 22 , R 24 and R 26 is a substituent. X 2 is a boron atom, R 22 ~R 26 of The substituent is preferably an unsubstituted alkyl group. Elementary atoms and X 1 or X 2 Specific examples of the group bonded to the boron atom represented by are given below. However, the groups bonded to the boron atom that can be used in the present invention are limited by the following specific examples: In this specification, the notation CH3 is omitted for the methyl group. * indicates the bond position. [ka]

[0015] In the following, R in general formula (1) 1 ~R 26 Here are some specific examples: R 1 ~R 7 , X 1 Nitrogen R when it is an elementary atom 13 ~R 21 , X 2 R when is a nitrogen atom 18 ~R 26 as Z1 to Z9 are preferred, and R 8 ~R 12 , X 1 R when is a nitrogen atom 22 ~R 26 , X 2 R when is a nitrogen atom 13 ~R 17 However, Z1 to Z7 are preferred. The groups bonded to the boron atom that can be employed in the above are construed as being limited by the following specific examples. D represents a deuterium atom. * represents a bonding position. [ka]

[0016] A 1 and A 2 is a hydrogen atom, a deuterium atom or a substituent. A group selected from any one of the above substituent groups A to E can be used. In a preferred embodiment of the present invention, A 1 and A 2 are each independently a hydrogen atom or a deuterium atom For example, A 1 and A 2 is a hydrogen atom. For example, A 1 and A 2 is deuterium It is an atom. A 1 and A 2 One of A may be a substituent. 1 and A 2 are placed independently It may be a substituent. 1 and A 2 The preferred substituents that can be taken by are acceptor groups. The acceptor group is a group having a positive Hammett σp value. The "p-value" was proposed by L.P. Hammett and is a reaction coefficient for para-substituted benzene derivatives. It quantifies the effect of substituents on the reaction rate or equilibrium. The following equation holds between the substituents in benzene derivatives and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp In the above equation, k0 is the constant (σp) specific to the substituent in is the rate constant of the benzene derivatives, k is the rate constant of the benzene derivatives substituted with substituents, and K0 is the The equilibrium constant of the unsubstituted benzene derivative is K, and the equilibrium constant of the substituted benzene derivative is K. The equilibrium constant, ρ, represents a reaction constant determined by the type and conditions of the reaction. For explanations of the "σp value of the compound" and the values ​​of each substituent, see Hansch, C. et al., Chem. Rev., 91 , 165-195 (1991) for a description of the σp value. A 1 and A 2 The acceptor group that can be taken is a group having a Hammett σp value of greater than 0.2. The group having a Hammett's σp value of more than 0.2 is preferably a cyano group. an aryl group substituted with at least a cyano group, a group containing a fluorine atom, a ring skeleton component element, Examples of the substituent include a substituted or unsubstituted heteroaryl group containing a nitrogen atom. The aryl group substituted with at least a cyano group here means an aryl group substituted with a substituent other than a cyano group ( It may be substituted with, for example, an alkyl group or an aryl group, but may be substituted only with a cyano group. The aryl group substituted with at least a cyano group may be an aryl group substituted with at least a cyano group. It is preferable that the phenyl group is substituted with at least one cyano group. is preferably 1 or 2, and may be, for example, 1 or 2. The group containing an element atom is a fluorine atom, a fluorinated alkyl group, or a fluorine atom or a fluorinated alkyl group. The fluorinated alkyl group can be substituted with at least one of the following: The alkyl group is preferably a fluoroalkyl group, and the number of carbon atoms is preferably 1 to 6. It is more preferable that the number of atoms constituting the ring skeleton is 1 to 3. The ring group may be a single ring or a fused ring in which two or more rings are fused together. In the case of a ring, the number of rings after condensation is preferably 2 to 6, for example, from 2 to 4. Specific examples of the ring constituting the heteroaryl group include: The pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, quinoline ring, isoquinolin ring, quinazoline ring, quinoxaline ring, naphthyridinyl ring other than quinazoline ring or quinoxaline ring The ring constituting the heteroaryl group can be substituted with a deuterium atom or a substituent. The substituents may be, for example, alkyl groups, aryl groups, and heteroaryl groups. a group formed by combining two or more groups selected from the group consisting of alkyl groups; A 1 and A 2 The following is a particularly preferred acceptor group: is a cyano group. In one aspect of the present invention, A 1 and A 2 At least one of the groups is an acceptor group. In one aspect of the invention, A 1 and A 2 Only one of the groups is an acceptor group. In your opinion, A 1 and A 2 In one embodiment of the present invention, both A and A are the same acceptor group. 1 and A 2 are different acceptor groups. 1 and A 2 is a cyano group. 1 and A 2 is a halogen atom, e.g. For example, a bromine atom.

[0017] Specific examples of the acceptor group that can be used in the present invention are shown below. However, the acceptor groups that can be used in the present invention are limited by the following specific examples. In this specification, the methyl group is omitted from the CH3 notation. For example, A15 indicates a group containing two 4-methylphenyl groups. "D" represents a deuterium atom. * represents a bond position. [ka] [ka]

[0018] In addition, X 1 is a nitrogen atom, and R 7 and R 8 are bonded via a nitrogen atom to form a six-membered ring and R 21 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 But each other When bonded to form a single bond, R 1 ~R 6 At least one of the following is replaced or omitted. substituted 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 or any of the aromatic rings (substituted or unsubstituted benzene rings which may be condensed) a heteroaromatic ring) or a heteroaromatic ring (preferably a substituted or unsubstituted benzophenone ring which may be condensed) furan ring of orthothiophene, thiophene of optionally fused substituted or unsubstituted benzothiophene It forms a ring. Also, X 1 is a boron atom, and X 2is a nitrogen atom, and R 7 and R 8 , R 17 and R 18 Mutually When a ring structure containing a boron atom is formed by bonding to the boron atom, the ring structure is a 5- to 7-membered ring. and when it is a six-membered ring, R 7 and R 8 , R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or -N(R 27 )- is formed. R 27 is a hydrogen atom, It preferably represents a deuterium atom or a substituent.

[0019] X in general formula (1) 1 When is a nitrogen atom, the compound of the present invention has the following skeleton (1a): X in general formula (1) 2 is a nitrogen atom, the compound of the present invention has the following skeleton (1b): It has. [ka]

[0020] Each hydrogen atom in the skeletons (1a) and (1b) is replaced by a deuterium atom or a substituent. Alternatively, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). 1 ~R 26 , A 1 , A 2 Record of The following can be seen in the skeletons (1a) and (1b): The phenyl groups are all mesityl groups, 2,6-diisopropylphenyl groups, or 2,4 , and compounds substituted with a 6-triisopropylphenyl group. In one embodiment of the present invention, each hydrogen atom in the skeletons (1a) and (1b) is connected to an adjacent hydrogen atom. The atom is not substituted with a linking group to form a ring structure.

[0021] A preferred group of compounds having the skeleton (1a) includes compounds represented by the following general formula (1a): Examples of such compounds include: General formula (1a) [ka]

[0022] In the general formula (1a), Ar 1 ~Ar 4 each independently represents a substituted or unsubstituted aryl a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group; For example, a substituted or unsubstituted aryl group can be preferably selected. 41 and R 42 m1 and m2 each independently represent a substituted or unsubstituted alkyl group. n1 and n3 each independently represent an integer of 0 to 4, and n2 and n4 each independently represents an integer of 0 to 3. 1 , A 2 are independently hydrogen atoms, heavy water At least one of n1 to n4 is 1 or more, and m1 and m Preferably, each 2 is independently an integer of 1 to 5. In one embodiment of the present invention, n1 to n4 each independently represent an integer of 0 to 2. In one embodiment, at least one of n1 to n4 is 1 or more, and preferably n1 and n2 At least one of n3 and n4 is 1 or greater, and at least one of n4 and n5 is 1 or greater. In one embodiment, n1 and n3 are each independently 1 or 2, and n2 and n4 are 0. In one embodiment of the present invention, n2 and n4 are each independently 1 or 2, and n1 and n In one embodiment of the present invention, n1 to n4 are each independently 1 or 2. In one embodiment of the present invention, n1 and n3 are equal, and n2 and n4 are equal. n3 is 1, and n2 and n4 are 0. In one embodiment of the present invention, n1 and n3 are 0, n2 and n4 are 1. In one embodiment of the present invention, n1 to n4 are all 1. Ar 1 ~ Ar 4 The bonding position may be at least one of the 3- and 6-positions of the carbazole ring. , 7 positions, or at least one of 1st and 8th positions. , and at least one of the 4 and 5 positions. 1 ~Ar 4 The bond position of It may be both the 3- and 6-positions of the ring, or both the 2- and 7-positions, or both the 1- and 8-positions. For example, at least one of the 3rd and 6th positions may be present. One of the positions can be preferably selected, or both the 3rd and 6th positions can be more preferably selected. In a preferred embodiment of the present invention, Ar 1 ~Ar 4 are all the same group In a preferred embodiment of the present invention, Ar 1 ~Ar 4 are each independently substituted or unsubstituted aryls. is preferably a substituted or unsubstituted phenyl group or naphthyl group. A substituted or unsubstituted phenyl group is more preferred. Examples of the phenyl group include a group selected from any one of groups A to E, and also include an unsubstituted phenyl group. Preferred. Ar 1 ~Ar 4Preferred specific examples of the group include a phenyl group, an o-biphenyl group, and m Examples of the phenyl group include a -biphenyl group, a p-biphenyl group, and a terphenyl group. In one embodiment of the present invention, m1 and m2 are each independently 0. In one embodiment of the present invention, m 1 and m2 each independently represent an integer of 1 to 5. In one embodiment of the present invention, m1 and In one aspect of the present invention, R 41 and R 42 is an alkyl group with 1 to 6 carbon atoms For example, alkyl groups having 1 to 3 carbon atoms or methyl groups can be selected. The substitution position of the alkyl group is determined by counting the carbon atom bonded to the boron atom as the first position. 2nd place only, 3rd place only, 4th place only, 3rd and 5th, 2nd and 4th, 2nd and 6th, 2nd and 4th and 6-positions, and at least 2-positions are preferred. It is more preferable that they are in the 1st and 6th positions. A 1 and A 2 For the explanation and preferred range of , see the corresponding description of general formula (1). It is possible.

[0023] Specific examples of the compound represented by general formula (1a) are listed below. The compounds of general formula (1a) that can be obtained are limited to the following group of specific examples. For example, a preferred group includes the compound shown in the center of the fourth row below and the compound shown in the center of the eighth row below. The group consisting of the remaining compounds excluding the compound can be mentioned. [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0024] Another group of specific examples of the compound represented by general formula (1a) will be listed below. The compounds of general formula (1a) that can be used in the present invention are limited to the following group of specific examples: It will not be interpreted. [ka] [ka] [ka] [ka] [ka]

[0025] A preferred group of compounds having the skeleton (1b) includes compounds represented by the following general formula (1b): Examples of such compounds include: General formula (1b) [ka]

[0026] In the general formula (1b), Ar 5 ~Ar 8 each independently represents a substituted or unsubstituted aryl a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group; For example, a substituted or unsubstituted aryl group can be preferably selected. 43 and R 44 m3 and m4 each independently represent a substituted or unsubstituted alkyl group. n6 and n8 each independently represent an integer of 0 to 5; n5 and n7 each independently represents an integer of 0 to 4. 1 , A 2 are independently hydrogen atoms, heavy water Represents an atom or a substituent. 5 ~Ar 8 , R 43 and R 44 , m3 and m4, n 5~n8, A 1 , A 2 For details, see Ar in general formula (1a). 1 ~Ar 4 , R 41 Oh BiR 42 , m1 and m2, n1 to n4, A 1 , A 2 Please refer to the description of At least one of n5 to n8 is 1 or more, and m3 and m4 each independently represent any one of 1 to 5. Preferably, the integer is 0.

[0027] Specific examples of the compound represented by general formula (1b) are listed below. The compounds of general formula (1b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0028] R in general formula (1) 7 and R 8 When these are bonded together to form N-Ph, the compound of the present invention is X 1 When is a nitrogen atom, for example, the following skeleton (2a) is obtained, and X 2 is a nitrogen atom It sometimes has, for example, the following skeleton (2b): Ph is a phenyl group. Skeleton (2a) [ka]

[0029] Each hydrogen atom in the skeletons (2a) and (2b) is replaced by a deuterium atom or a substituent. Alternatively, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). 1 ~R 26 , A 1 , A 2 Record of The carbazole moiety contained in the skeleton (2a) can be found in the following description. At least one hydrogen atom of the benzene ring is substituted with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeletons (2a) and (2b) is The adjacent hydrogen atoms are substituted with linking groups to form no ring structure.

[0030] A preferred group of compounds having the skeleton (2a) includes compounds represented by the following general formula (2a): Examples of such compounds include: General formula (2a) [ka]

[0031] In the general formula (2a), Ar 9 ~Ar 14 are each independently a substituted or unsubstituted aryl group. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group n9 represents a substituted or unsubstituted aryl group, for example. , n11, n12, and n14 each independently represent an integer of 0 to 4, and n10 and n13 each Each independently represents an integer of 0 to 2, provided that at least one of n9, n10, n12, and n13 One is greater than or equal to 1. A 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent. vinegar. In one embodiment of the present invention, n9 to n14 each independently represent an integer of 0 to 2. In this case, at least one of n9 to n14 is 1 or more. For example, n9 and n12 are 1 or more. or n10 and n13 can be 1 or more. In one embodiment, at least one of n9, n10, n12, and n13 is 1 or greater. In one embodiment, n9 and n12 are each independently 1 or 2, and n10, n11, n13 and n14 is 0. In one embodiment of the present invention, n10 and n13 are each independently 1 or 2. and n9, n11, n12, and n14 are 0. In one embodiment of the present invention, n9 and n1 2 each independently represents 1 or 2, n10 and n13 each independently represents 1 or 2, n11 and n14 are 0. In one embodiment of the present invention, n9 to n14 are all 1. Ar 9 ~Ar 14 The bonding positions may be the 3rd and 6th positions of the carbazole ring or other positions. In a preferred embodiment of the present invention, Ar 9 ~Ar 14 are all the same It is a group of Ar 9 ~Ar 14 For preferred groups, Ar 1 ~Ar 4 The corresponding statement of You can refer to: A1 and A 2 The description and preferred range of the general formula (1 ) can be referred to the corresponding description.

[0032] Specific examples of the compound represented by general formula (2a) are listed below. The compounds of general formula (2a) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0033] A preferred group of compounds having the skeleton (2b) includes compounds represented by the following general formula (2b): Examples of such compounds include: General formula (2b) [ka]

[0034] In the general formula (2b), Ar 15 ~Ar 20 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. 15, n17, n18, and n20 each independently represent an integer of 0 to 4, and n16 and n19 Each independently represents an integer of 0 to 2. 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or Represents a substituent. Ar 15 ~Ar 20 , n15~n20, A 1 , A 2 For more information, see Ar of general formula (2a) 9 ~Ar 14 , n9~n14, A 1 , A2 Please refer to the descriptions in order. can be done.

[0035] Specific examples of the compound represented by general formula (2b) are listed below. The compounds of general formula (2b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0036] R in general formula (1) 7 and R 8 are bonded to each other to form a single bond, the compound of the present invention is X 1 When is a nitrogen atom, for example, the following skeleton (3a) is obtained, and X 2 is a nitrogen atom For example, it has the following skeleton (3b): [ka]

[0037] Each hydrogen atom in the skeletons (3a) and (3b) is replaced by a deuterium atom or a substituent. Alternatively, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). 1 ~R 26 , A 1 , A 2 Record of In one embodiment of the present invention, the structure (3a) and the structure (3b) Each hydrogen atom is not substituted with an adjacent hydrogen atom by a linking group to form a ring structure. .

[0038] A preferred group of compounds having the skeleton (3a) includes compounds represented by the following general formula (3a): Examples of such compounds include: General formula (3a) [ka]

[0039] In the general formula (3a), Ar 21 ~Ar 26 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. 21, n23, n24, and n26 each independently represent an integer of 0 to 4, and n22 and n25 Each independently represents an integer of 0 to 2. 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or Represents a substituent. Ar 21 ~Ar 25 , n21 to n25 are represented by the general formula (2a) Ar 9 ~Ar 14 , n9~n14, A 1 , A 2 The description can be referred to.

[0040] Specific examples of the compound represented by general formula (3a) are listed below. The compounds of general formula (3a) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0041] A preferred group of compounds having the skeleton (3b) includes compounds represented by the following general formula (3b): Examples of such compounds include: General formula (3b) [ka]

[0042] In the general formula (3b), Ar 27 ~Ar 32 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. 27, n29, n30, and n32 each independently represent an integer of 0 to 4, and n28 and n31 Each independently represents an integer of 0 to 2. 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or Represents a substituent. Ar 27 ~Ar 32 , n27~n32, A 1 , A 2 For more information, see Ar of general formula (2b) 15 ~Ar 20 , n15~n20, A 1 , A 2 Please refer to the descriptions in order. It is possible.

[0043] Specific examples of the compound represented by general formula (3b) are listed below. The compounds of general formula (3b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0044] In a preferred embodiment of the present invention, the carbazole moiety present in general formula (1) is Select compounds in which two benzene rings are fused with other rings. Compounds with fused benzothiophene rings, compounds with fused benzene rings, These ring-fused compounds are particularly preferably selected. I will explain this by giving specific examples.

[0045] Of the two benzene rings constituting the carbazole moiety in general formula (1), A benzofuran ring or a benzothiophene ring is attached to a benzene ring to which no atom is directly bonded. Condensed compounds are preferred. Examples of such compounds include the following skeletons: Examples include a compound having the structure (4a) and a compound having the following structure (4b). do. [ka]

[0046] In skeletons (4a) and (4b), Y 1 ~Y 4 are each independently two hydrogen atoms, a single bond or N(R 27 ) The two hydrogen atoms in this case are the two hydrogen atoms bonded to the boron atom. This shows two benzene rings that are not linked to each other. 1 and Y 2 is the same as Y 3 and Y 4 are preferably the same, but may be different. So, Y 1 ~Y 4 is a single bond. In one aspect of the present invention, Y 1 ~Y 4 is N(R 27 ) R 27 represents a hydrogen atom, a deuterium atom or a substituent. Z 1 ~Z 4 each independently represents an oxygen atom or a sulfur atom. 1 and Z 2 are the same, and Z 3 and Z 4are preferably the same, but may be different. So Z 1 ~Z 4 is an oxygen atom. In this case, the furan ring of benzofuran is (4a) and The benzene ring in (4b) is fused to the carbazole moiety. The orientation of the furan ring is not limited. 1 ~Z 4 is a sulfur atom In this case, the thiophene ring of benzothiophene is connected to the carboxyl group in (4a) and (4b). The thiophene ring is fused to the benzene ring that constitutes the benzol substructure. There are no restrictions on the use of Each hydrogen atom in the skeletons (4a) and (4b) is replaced by a deuterium atom or a substituent. Alternatively, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). 1 ~R 26 , A 1 , A 2 Record of In one embodiment of the present invention, the structure (4a) and the structure (4b) Each hydrogen atom is not substituted with an adjacent hydrogen atom by a linking group to form a ring structure. .

[0047] A preferred group of compounds having the skeleton (4a) includes compounds represented by the following general formula (4a): In the specific examples, X is an oxygen atom or a sulfur atom, and The compounds where X is an atom and where X is a sulfur atom are also disclosed. X in the specific examples of the compounds represented by the other general formulas below has the same meaning. General formula (4a) [ka]

[0048] In the general formula (4a), Ar 51 and Ar 52 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aryl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. R 51 and R 52 Each of m51 and m52 independently represents a substituted or unsubstituted alkyl group. and m52 each independently represents an integer of 0 to 4. n51 and n52 each independently represents an integer of 0 to 2. Represents an integer. Y 1 ~Y 4 are each independently two hydrogen atoms, a single bond, or N(R 27 ) .R 27 represents a hydrogen atom, a deuterium atom or a substituent. 1 ~Z 4 are each independently oxygen A represents an atom or a sulfur atom. 1 , A 2 are each independently a hydrogen atom, a deuterium atom or a substituted Represents a group. In one embodiment of the present invention, n51 and n52 are the same number. For example, n51 and n52 are 0. In one embodiment of the present invention, m51 and m52 may be 0 or 1, and n51 and n52 may be 1. In one embodiment of the present invention, m51 and m52 are integers of 0 to 3. For example, , m51 and m52 may be 0, m51 and m52 may be 1, and m51 and m m51 and m52 may be 3. 51 , Ar 52 , R 51 , R 52 , A 1 , A 2 The preferred groups are Ar1 ~Ar 4 , R 41 ~R 42 , A 1 , A 2 Reference can be made to the corresponding description in

[0049] Specific examples of the compound represented by general formula (4a) are listed below. The compounds of general formula (4a) that can be obtained are limited to the following group of specific examples: Regarding specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and Each compound in which all X's in the molecule are sulfur atoms is also intended to be disclosed. A compound in which some of the X's are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka] [ka] [ka] [ka]

[0050] Another group of specific examples of the compound represented by general formula (4a) will be listed below. The compounds of general formula (4a) that can be used in the present invention are limited to the following group of specific examples: It will not be interpreted. [ka] [ka]

[0051] A preferred group of compounds having the skeleton (4b) includes compounds represented by the following general formula (4b): Examples of such compounds include: General formula (4b) [ka]

[0052] In the general formula (4b), Ar 53 and Ar 54 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aralkyl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. .R 53 and R 54 Each of m53 and m54 independently represents a substituted or unsubstituted alkyl group. m53 and m54 each independently represent an integer of 0 to 4. n53 and n54 each independently represent an integer of 0 to 2. Represents a number. Y 3 and Y 4 are each independently two hydrogen atoms, a single bond, or N(R 27 ) R 27 represents a hydrogen atom, a deuterium atom or a substituent. 3 and Z 4 are independent of each other represents an oxygen atom or a sulfur atom. 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or represents a substituent. 53 , Ar 54 , R 53 , R 54 , m53, m54, n53, n5 4. A 1 , A 2 For details, see Ar in general formula (4a). 51 , Ar 52 , R51 , R 5 2 , m51, m52, n51, n52, A 1 , A 2 The description can be referred to.

[0053] Specific examples of the compound represented by general formula (4b) are listed below. The compounds of general formula (4b) that can be obtained are not to be construed as being limited by the following specific examples. As for specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and compounds in which all Xs in the molecule are oxygen atoms. Each compound in which all X's are sulfur atoms is also disclosed. A compound in which some of the atoms are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0054] Of the two benzene rings constituting the carbazole moiety in general formula (1), A benzofuran or benzothiophene ring is fused to a benzene ring to which an atom is directly bonded. Examples of such compounds include the following compounds having the following skeleton: Examples include a compound having the following skeleton (5a) and a compound having the following skeleton (5b): . [ka]

[0055] In skeletons (5a) and (5b), Y 5 ~Y 8 are each independently two hydrogen atoms, a single bond or N(R 27 ) represents Z. 5 ~Z 8 each independently represents an oxygen atom or a sulfur atom Y 5~Y 8 , Z 5 ~Z 8 For details, see the corresponding notations in skeletons (4a) and (4b). In one embodiment of the present invention, the structure (5a) and the structure (5b) Each hydrogen atom is not substituted with an adjacent hydrogen atom by a linking group to form a ring structure. .

[0056] A preferred group of compounds having the skeleton (5a) includes compounds represented by the following general formula (5a): Examples of such compounds include: General formula (5a) [ka]

[0057] In the general formula (5a), Ar 55 and Ar 56 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aralkyl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. .R 55 and R 56 Each of m55 and m65 independently represents a substituted or unsubstituted alkyl group. m55 and m56 each independently represent an integer of 0 to 4. n55 and n56 each independently represent an integer of 0 to 4. Represents a number. Y 5 and Y 6 are each independently two hydrogen atoms, a single bond, or N(R 27 ) R 27 represents a hydrogen atom, a deuterium atom or a substituent. 5 and Z 6 are independent of each other represents an oxygen atom or a sulfur atom. 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or represents a substituent. In one embodiment of the present invention, n55 and n56 are integers of 0 to 2. For example, n55 and n56 may be 0, and n55 and n56 may be 1. In one embodiment of the present invention, m51 and m52 are the same number. For details about m55 and m56, see m51 and m56 in general formula (4a). Please refer to the description of m52. 55 , Ar 56 , R 55 , R 56 , A 1 , A 2 The preferred groups are Ar 1 , Ar 3 , R 41 , R 42 , A 1 , A 2 Reference can be made to the corresponding description in

[0058] Specific examples of the compound represented by general formula (5a) are listed below. The compounds of general formula (5a) that can be obtained are limited to the following group of specific examples: Regarding specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and Each compound in which all X's in the molecule are sulfur atoms is also intended to be disclosed. A compound in which some of the X's are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka] [ka] [ka]

[0059] Another group of specific examples of the compound represented by general formula (5a) will be listed below. The compounds of general formula (5a) that can be used in the present invention are limited to the following group of specific examples: It will not be interpreted. [ka]

[0060] A preferred group of compounds having the skeleton (5b) includes compounds represented by the following general formula (5b): Examples of such compounds include: General formula (5b) [ka]

[0061] In the general formula (5b), Ar 57 and Ar 58 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aralkyl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. .R 57 and R 58 Each independently represents a substituted or unsubstituted alkyl group. m57 and m58 each independently represent an integer of 0 to 4. n57 and n58 each independently represent an integer of 0 to 4. Represents a number. Y 7 and Y 8 are each independently two hydrogen atoms, a single bond, or N(R 27 ) R 27 represents a hydrogen atom, a deuterium atom or a substituent. 7 and Z 8 are independent of each other represents an oxygen atom or a sulfur atom. 1 , A 2are each independently a hydrogen atom, a deuterium atom, or represents a substituent. 57 , Ar 58 , R 57 , R 58 , m57, m58, n57, n5 8. A 1 , A 2 For details, see Ar in general formula (5a). 55 , Ar 56 , R 55 , R 5 6 , m55, m56, n55, n56, A 1 , A 2 The description can be referred to.

[0062] Specific examples of the compound represented by general formula (5b) are listed below. The compounds of general formula (5b) that can be obtained are limited to the following group of specific examples: Regarding specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and Each compound in which all X's in the molecule are sulfur atoms is also intended to be disclosed. A compound in which some of the X's are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0063] Another group of specific examples of the compound represented by general formula (5b) will be listed below. The compounds of general formula (5b) that can be used in the present invention are limited to the following group of specific examples: It will not be interpreted. [ka] [ka]

[0064] In both of the two benzene rings constituting the carbazole moiety present in general formula (1), Preferred examples include compounds in which a benzofuran ring or a benzothiophene ring is condensed. Examples of such compounds include a compound having the following skeleton (6a) and a compound having the following skeleton ( 6b) can be exemplified. [ka]

[0065] In skeletons (6a) and (6b), Y 9 ~Y 12 are each independently two hydrogen atoms, a single Bond or N(R 27 ) represents Z. 9 ~Z 16 each independently represents an oxygen atom or a sulfur atom Represents Z. 9 ~Z 16 are preferably the same, but may be different. In one embodiment, Z 9 ~Z 16 is an oxygen atom. In one embodiment of the present invention, Z 9 ~Z 16 is sulfur It is an atom. Y 9 ~Y 12 For details, see the corresponding notations in skeletons (4a) and (4b). In one embodiment of the present invention, the structure (6a) and the structure (6b) Each hydrogen atom is not substituted with an adjacent hydrogen atom by a linking group to form a ring structure. .

[0066] A preferred group of compounds having the skeleton (6a) includes compounds represented by the following general formula (6a): Examples of such compounds include: General formula (6a) [ka]

[0067] In general formula (6a), R 59 and R 60 are each independently a substituted or unsubstituted alkyl group; m59 and m60 each independently represent an integer of 0 to 4. Y 9 and Y 10 are each independently two hydrogen atoms, a single bond, or N(R 27 ) represents R 27 is a hydrogen atom, Represents a deuterium atom or a substituent. Z 9 ~Z 12 each independently represents an oxygen atom or a sulfur atom Represents. A 1 , A 2 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 59 , R 60 , m59, m60, Z 9 ~Z 12 , A 1 , A 2 For details, see general formula (5a) R 55 , R 56 , m55, m56, A 1 , A 2 and Z in skeleton (6a) 9 ~Z 12 of You can refer to the description.

[0068] Specific examples of the compound represented by general formula (6a) are listed below. The compounds of general formula (6a) that can be obtained are not to be construed as being limited by the following specific examples. As for specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and compounds in which all Xs in the molecule are oxygen atoms. Each compound in which all X's are sulfur atoms is also disclosed. A compound in which some of the atoms are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka] [ka] [ka]

[0069] A preferred group of compounds having the skeleton (6b) includes compounds represented by the following general formula (6b): Examples of such compounds include: General formula (6b) [ka]

[0070] In general formula (6b), R 61 and R 62 are each independently a substituted or unsubstituted alkyl group; m61 and m60 each independently represent an integer of 0 to 4. Y 11 and Y 1 2 are each independently two hydrogen atoms, a single bond, or N(R 27 ) represents R 27 is a hydrogen atom , represents a deuterium atom or a substituent. Z 13 ~Z 16 are each independently an oxygen atom or a sulfur atom A represents a child. 1 , A 2 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 61 , R 62 , m61, m62, Z 13 ~Z 16 , A 1 , A 2 For details, see the general formula (6 a) R 59, R 60 , m59, m60, A 1 , A 2 and Z in skeleton (6b) 13 ~ Z 16 The description can be referred to.

[0071] Specific examples of the compound represented by general formula (6b) are listed below. The compounds of general formula (6b) that can be obtained are not to be construed as being limited by the following specific examples. As for specific examples containing X, there are compounds in which all Xs in the molecule are oxygen atoms, and compounds in which all Xs in the molecule are oxygen atoms. Each compound in which all X's are sulfur atoms is also disclosed. A compound in which some of the atoms are oxygen atoms and the rest are sulfur atoms can also be used. [ka] [ka] [ka]

[0072] Of the two benzene rings constituting the carbazole moiety in general formula (1), A preferred example is a compound in which a benzene ring is condensed with a benzene ring to which no atom is directly bonded. Examples of such compounds include a compound having the following skeleton (7a): An example is a compound having the following skeleton (7b). [ka]

[0073] In skeletons (7a) and (7b), Y 21 ~Y 24 each independently represents two hydrogen atoms, Single bond or N(R27 ) Y 21 ~Y 24 For details, see the skeleton (4a) and Y in (4b) 1 ~Y 4 In one embodiment of the present invention, the backbone (7 Each hydrogen atom in a) and (7b) is replaced with a linking group together with the adjacent hydrogen atom. It does not form a ring structure.

[0074] A preferred group of compounds having the skeleton (7a) includes compounds represented by the following general formula (7a): Examples of such compounds include: General formula (7a) [ka]

[0075] In the general formula (7a), Ar 71 ~Ar 74 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n71 and n73 each independently represent an integer of 0 to 2. n72 and n74 each independently represent an integer of 0 to 2. Represents an integer between 0 and 4. 21 and Y 22 are each independently two hydrogen atoms, a single bond or N( R 27 ) represents R 27 represents a hydrogen atom, a deuterium atom or a substituent. 1 , A 2 teeth, Each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n71 to n74 are integers of 0 to 2. In one embodiment of the present invention, n 71 and n73 are the same number, and n72 and n74 are the same number. n71 to n74 are the same number For example, n71 to n74 may be 0. All of n71 to n74 may be 1. Also, for example, , n71 and n73 may be 0, and n72 and n74 may be 1. Ar 71 ~ Ar 74 , A 1 , A 2 The preferred groups are Ar 1 ~Ar 4 , A 1 , A 2 Reference can be made to the corresponding description in

[0076] Specific examples of the compound represented by general formula (7a) are listed below. The compounds of general formula (7a) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0077] A preferred group of compounds having the skeleton (7b) includes compounds represented by the following general formula (7b): Examples of such compounds include: General formula (7b) [ka]

[0078] In the general formula (7b), Ar 75 ~Ar 78 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n75 and n77 each independently represent an integer of 0 to 2. n76 and n78 each independently represent an integer of 0 to 2. Represents an integer between 0 and 4. 23and Y 24 are each independently two hydrogen atoms, a single bond or N( R 27 ) represents R 27 represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed explanation of n71 to n74 in general formula (7a), please refer to the descriptions of n71 to n74 in order. Ar 75 ~Ar 78 The preferred groups are Ar 1 ~Ar 4 Reference can be made to the corresponding description in

[0079] Specific examples of the compound represented by general formula (7b) are listed below. The compounds of general formula (7b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0080] Of the two benzene rings constituting the carbazole moiety in general formula (1), Preferred examples of the compound include a compound in which a benzene ring is condensed with a benzene ring to which an atom is directly bonded. Examples of such compounds include a compound having the following skeleton (8a) and a compound having the following skeleton (8b): Examples include compounds having the following skeleton (8b). [ka]

[0081] In skeletons (8a) and (8b), Y 25 ~Y 28 each independently represents two hydrogen atoms, Single bond or N(R 27 ) Y 25 ~Y 28 For details, see the skeleton (4a) and In one embodiment of the present invention, the skeleton (8a) and (8b), each hydrogen atom, together with the adjacent hydrogen atom, is substituted with a linking group to form a ring. No crystalline structure is formed.

[0082] A preferred group of compounds having the skeleton (8a) includes compounds represented by the following general formula (8a): Examples of such compounds include: General formula (8a) [ka]

[0083] In the general formula (8a), Ar 79 and Ar 80 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aralkyl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. .R 71 and R 72 Each of m71 and m72 independently represents a substituted or unsubstituted alkyl group. m72 and m73 each independently represent an integer of 0 to 4. n79 and n80 each independently represent an integer of 0 to 4. Represents a number. Y 25 and Y 26 are each independently two hydrogen atoms, a single bond, or N(R 27 ) Represents R 27 represents a hydrogen atom, a deuterium atom or a substituent. 1 , A 2 are independent of each other represents a hydrogen atom, a deuterium atom or a substituent. In one embodiment of the present invention, n79 and n80 are integers of 0 to 2. , n79 and n80 are the same number, and for example, they may both be 0 or both be 1. In one embodiment of the present invention, m71 and m72 are integers of 0 to 2. In one embodiment, m71 and m72 are the same number, for example, both may be 0, Both may be 1. Ar 79 , Ar 80 , R 71 , R 72 , A 1 , A 2 Preferred Regarding the Ar group of general formula (1a), 1 , Ar 3 , R 41 , R 42 , A 1 , A 2 Response The following description can be referred to.

[0084] Specific examples of the compound represented by general formula (8a) are listed below. The compounds of general formula (8a) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0085] A preferred group of compounds having the skeleton (8b) includes compounds represented by the following general formula (8b): Examples of such compounds include: General formula (8b) [ka]

[0086] In the general formula (8b), Ar 81 and Ar 82 are each independently substituted or unsubstituted an aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted aralkyl group; It represents an alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. .R73 and R 74 Each of m73 and m74 independently represents a substituted or unsubstituted alkyl group. m74 and m75 each independently represent an integer of 0 to 4. n81 and n82 each independently represent an integer of 0 to 4. Represents a number. Y 27 and Y 28 are each independently two hydrogen atoms, a single bond, or N(R 27 ) Represents R 27 represents a hydrogen atom, a deuterium atom or a substituent. 1 , A 2 are independent of each other represents a hydrogen atom, a deuterium atom or a substituent. For detailed explanation of m73, m74, n81, and n82, see m71 in general formula (8a), Please refer to the descriptions in m72, n79, and n80. 81 , Ar 82 , R 73 , R 74 , A 1 , A 2 The preferred groups are Ar 1 , Ar 3 , R 41 , R 42 , A 1 , A 2 Reference can be made to the corresponding description in

[0087] Specific examples of the compound represented by general formula (8b) are listed below. The compounds of general formula (8b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0088] In both of the two benzene rings constituting the carbazole moiety present in general formula (1), Compounds in which benzene rings are condensed are preferred. Examples of such compounds include Examples of the compound include a compound having the following skeleton (9a) and a compound having the following skeleton (9b). It is possible. [ka]

[0089] In skeletons (9a) and (9b), Y 29 ~Y 32 each independently represents two hydrogen atoms, Single bond or N(R 27 ) Y 29 ~Y 32 For details, see the skeleton (4a) and In one embodiment of the present invention, the skeleton (9a) and (9b), each hydrogen atom, together with the adjacent hydrogen atom, is substituted with a linking group to form a ring. No crystalline structure is formed.

[0090] A preferred group of compounds having the skeleton (9a) includes compounds represented by the following general formula (9a): Examples of such compounds include: General formula (9a) [ka]

[0091] In general formula (9a), R 75 and R 76 are each independently a substituted or unsubstituted alkyl group; m75 and m76 each independently represent an integer of 0 to 4. Y 29 and Y 3 0 are each independently two hydrogen atoms, a single bond, or N(R 27 ) represents R 27 is a hydrogen atom , represents a deuterium atom or a substituent. 1 , A2 are each independently a hydrogen atom, a deuterium atom, or represents a substituent. 75 , R 76 , m75, m76, A 1 , A 2 For more information, see General R in Equation (8a) 71 , R 72 , m71, m72, A 1 , A 2 You can refer to the description of do.

[0092] Specific examples of the compound represented by general formula (9a) are listed below. The compounds of general formula (9a) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka] [ka]

[0093] A preferred group of compounds having the skeleton (9b) includes compounds represented by the following general formula (9b): Examples of such compounds include: General formula (9b) [ka]

[0094] In general formula (9b), R 77 and R 78 are each independently a substituted or unsubstituted alkyl group; m77 and m78 each independently represent an integer of 0 to 4. Y 31 and Y 3 2 are each independently two hydrogen atoms, a single bond, or N(R 27 ) represents R 27 is a hydrogen atom , represents a deuterium atom or a substituent.1 , A 2 are each independently a hydrogen atom, a deuterium atom, or represents a substituent. 77 , R 78 , m77, m78, A 1 , A 2 For more information, see General R in Equation (8a) 71 , R 72 , m71, m72, A 1 , A 2 You can refer to the description of do.

[0095] Specific examples of the compound represented by general formula (9b) are listed below. The compounds of general formula (9b) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka]

[0096] The compound represented by the general formula (1) has four or more carbazole moieties in the molecule. Compounds containing the following skeleton (10) are also preferred. Examples of such things can be given. Skeleton (10) [ka]

[0097] Each hydrogen atom in the skeleton (10) may be substituted with a deuterium atom or a substituent. In addition, the adjacent hydrogen atom may be substituted with a linking group to form a cyclic structure. For details, see the corresponding R in general formula (1). 1 ~R 26 , A 1 , A 2 Please refer to the description of The benzene ring constituting the carbazole partial structure contained in the skeleton (10) can be At least one hydrogen atom is replaced with a substituted or unsubstituted aryl group. In one embodiment, each hydrogen atom in backbone (10) is linked together with an adjacent hydrogen atom to form a linking group. is substituted to form a ring structure.

[0098] A preferred group of compounds having the skeleton (10) includes compounds represented by the following general formula (10): Examples of such compounds include: General formula (10) [ka]

[0099] In the general formula (10), Ar 91 ~Ar 94 are each independently substituted or unsubstituted aryls. a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl n represents a group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n91 and n93 each independently represent an integer of 0 to 4, and n92 and n94 each independently represent an integer of 0 to 4. The α ring, β ring, γ ring and δ ring may be substituted, and may each represent an integer of 1 to 3. The ring is substituted with a substituted or unsubstituted aryl group or an optionally substituted benzoate. The benzofuran ring is fused to the benzophenone ring, or the furan ring of a substituted or unsubstituted benzofuran or a substituted or unsubstituted benzophenone ring. The thiophene ring of an unsubstituted thiophene is condensed. 1 , A 2 are each independently hydrogen represents an atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n91 to n94 are integers of 0 to 2. In one embodiment of the present invention, n 91 and n93 are the same number, and n92 and n94 are the same number. n91 to n94 are all may be the same number, for example, they may all be 0 or they may all be 1. Yes. Ar 91 ~Ar 94 The preferred groups are Ar 1 ~Ar 4 Pair of In one embodiment of the present invention, the α-ring and the γ-ring have the same substituents. or have the same fused structure, and the β ring and the δ ring have the same substituent or have the same In one embodiment of the present invention, the β ring and the δ ring are both substituted or unsubstituted. It is substituted with an aryl group, or an optionally substituted benzene ring is fused, or The furan ring of substituted or unsubstituted benzofuran or the thiophene ring of substituted or unsubstituted thiophene In one embodiment of the present invention, both the α-ring and the γ-ring are substituted or unsubstituted. It is substituted with an optionally substituted aryl group or has an optionally substituted benzene ring fused thereto. , a furan ring of a substituted or unsubstituted benzofuran, or a substituted or unsubstituted thiophene In one embodiment of the present invention, all of the α ring, β ring, γ ring, and δ ring are fused to the thiophene ring. is substituted with a substituted or unsubstituted aryl group, or an optionally substituted benzene a substituted or unsubstituted benzofuran ring or a substituted or unsubstituted benzofuran ring A is an unsubstituted thiophene with a fused thiophene ring. 1 and A 2 Description and preferred For the range, reference can be made to the corresponding description of general formula (1).

[0100] Specific examples of the compound represented by general formula (10) are listed below. The compounds of general formula (10) that can be obtained are not to be construed as being limited by the following specific examples. stomach. [ka] [ka] [ka]

[0101] The compound represented by general formula (1) may have an asymmetric skeleton. For example, compounds having an asymmetric skeleton such as the following skeleton (11a) or the following skeleton (11b) It's okay to have one. [ka]

[0102] In skeletons (11a) and (11b), Z 17 and Z 18 are each independently oxygen atoms In one embodiment of the present invention, the nuclei in the skeletons (11a) and (11b) represent a hydroxyl group or a sulfur atom. Each hydrogen atom in the alkyl group is substituted with a linking group together with the adjacent hydrogen atom to form a ring structure. stomach.

[0103] A preferred group of compounds having the skeleton (11a) is represented by the following general formula (11a): Examples of compounds that can be used include: General formula (11a) [ka]

[0104] In the general formula (11a), Ar 83 ~Ar 85 are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group; For example, a substituted or unsubstituted aryl group can be preferably selected. R 83 and R 84 Each of Z independently represents a substituted or unsubstituted alkyl group. 17 is oxygen m83 and m84 each independently represent an integer of 0 to 5. n8 3 represents an integer of 0 to 4, and n84 and n85 each independently represent an integer of 0 to 3. Ar 83 ~Ar 85 , R 83 , R 84 Detailed explanation of m83, m84, n83~n85 The preferred range is as follows: Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1, m2, n1, n2, and n4.

[0105] Specific examples of the compound represented by general formula (11a) are listed below. The compound of general formula (11a) that can be used should be construed in a limited manner based on the following specific examples. In the following specific examples, there are compounds in which all Xs in the molecule are oxygen atoms, and compounds in which all Xs in the molecule are oxygen atoms. Each compound in which all X's in the molecule are sulfur atoms is also disclosed. A compound in which some of X's are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0106] A preferred group of compounds having the skeleton (11b) is represented by the following general formula (11b): Examples of compounds that can be used include: General formula (11b) [ka]

[0107] In the general formula (11b), Ar 86 ~Ar 88 are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group; For example, a substituted or unsubstituted aryl group can be preferably selected. R 86 and R 87 Each of Z independently represents a substituted or unsubstituted alkyl group. 18 is oxygen m86 and m87 each independently represent an integer of 0 to 5. n8 6 represents an integer of 0 to 4, and n87 and n88 each independently represent an integer of 0 to 3. Ar 86 ~Ar 88 , R 86 , R 87 Detailed explanation of m86, m87, n86~n88 The preferred range is as follows: Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1, m2, n1, n2, and n4.

[0108] Specific examples of the compound represented by general formula (11b) are listed below. The compound of general formula (11b) that can be used should be construed in a limited manner based on the following specific examples. In the following specific examples, there are compounds in which all Xs in the molecule are oxygen atoms, and compounds in which all Xs in the molecule are oxygen atoms. Each compound in which all X's in the molecule are sulfur atoms is also disclosed. A compound in which some of X's are oxygen atoms and the rest are sulfur atoms can also be used. [ka]

[0109] As the compound represented by general formula (1), R 5 is preferably used as a donor group. It is possible. R 5 Compounds in which is a donor group have a high molar absorption coefficient and high luminescence efficiency. For example, R 3 exhibits superior luminescence properties compared to compounds with donor groups. In a preferred embodiment of the present invention, R 3 is not a donor group. So, R 1 ~R 7 Among them, R 5 Only one group is a donor group, or both are donor groups (especially σ The donor group is not a group with a Hammett σp value of -0.2 or less. R 5 The donor group preferably has a σp value of −0.2 or less, for example, −0 It may be -0.4 or less, for example, -0.6 or less. Examples of the amino group include substituted amino groups, and preferred are substituted or unsubstituted diaryl amino groups. The aryl group may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after condensation is preferably 2 to 6, for example For example, it can be selected from 2 to 4, or it can be 2. The two aryl groups may be the same or different. may be linked via a single bond or a linking group. A preferred group is a substituted or unsubstituted diphenylamino group. The compound employs a substituted or unsubstituted carbazol-9-yl group to which the aryl group is bonded via a single bond. or a substituted or unsubstituted diphenyl group in which two phenyl groups are not bonded by a single bond. R in general formula (1) may be an arylamino group. 1 ~R 7 One of the following is a substituted amino group: At some point, at least R 5 is preferably a substituted amino group, and R 5 Only substituted amino In one aspect of the present invention, R 3 is not a substituted amino group. R 5 is a donor group, and X 1 is a nitrogen atom, R 16 or R 19 is the donor R is preferably a functional group. 19 is more preferably a donor group. Other R 1 ~R 26 may be, for example, all hydrogen atoms or all deuterium atoms, e.g. For example, R 3 , R 6 , R 15 , R 20 At least one of the groups is a substituent (preferably substituted or unsubstituted). substituted alkyl group, or substituted or unsubstituted aryl group), and the others are hydrogen atoms or It may also be a deuterium atom. R 5 is a donor group, and X 1 is a boron atom, R 20 or R 23 Donna R is preferably a substituted or unsubstituted group. 20 is more preferably a donor group. , and other R 1 ~R 26 may be, for example, all hydrogen atoms or all deuterium atoms, For example, R 3 , R 6 , R 19 , R 24At least one of the following is a substituent (preferably substituted or unsubstituted alkyl group, or substituted or unsubstituted aryl group), and the others are hydrogen atoms or may be a deuterium atom. R 5 A preferred group of compounds in which is a donor group is represented by the following general formula (12a): and a compound represented by the following general formula (12b): General formula (12a) [ka]

[0110] In the general formula (12a) and the general formula (12b), Ar 1 ~Ar 8 are each independently substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, or substituted or unsubstituted It represents an unsubstituted or substituted alkyl group, and for example, a substituted or unsubstituted alkyl group is preferably selected. Alternatively, a substituted or unsubstituted aryl group can be preferably selected. 5 represents a donor group. 41 ~R 44 each independently represents a substituted or unsubstituted alkyl group; m1 to m4 each independently represent an integer of 0 to 5. n1, n3, n5, and n7 each independently represent an integer of 0 to 5. represents an integer of 0 to 4, n4 and n8 represent an integer of 0 to 3, and n2' and n6' represent an integer of 0 to 4. Represents an integer between 0 and 2. 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent Ar 1 ~Ar 8 , R 41 ~R 44 , m1~m4, n1, n3~n5, n7, n8, A 1 , A 2For details, see the corresponding descriptions of general formula (1a) and general formula (1b). However, Ar bonded to adjacent carbon atoms can 1 Adjacent carbon atoms Ar bonded to atom 3 Ar bonded to adjacent carbon atoms 5 What's up, next door? Ar bonded to a matching carbon atom 7 Even if they bond to each other to form a ring structure, Preferably, benzofuran (fused with a furan ring) or benzothiophene (thiophene The ring may be fused with a ring.

[0111] Specific examples of the compounds represented by general formula (12a) and general formula (12b) are given below. However, the general formula (12a) and the general formula (12b) that can be used in the present invention are The compounds of formula (I) are not to be construed as being limited by the following specific examples. The structure of each compound is defined by specifying R, Ar, and X in F1 to F56 in the table. R is selected from A to D shown below, Ar is selected from a to d shown below, and X is selected from α to For example, compound No. 1 in the table is a compound in which R is A in formula F1. , a compound having a structure in which Ar is a.

[0112] [ka] [ka] [ka] [ka] [ka] [ka] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9]

[0113] [ka]

[0114] In one embodiment of the present invention, the skeletons (1a) to (12b) are not further condensed with other rings. In one embodiment of the present invention, the skeletons (1a) to (12b) each further include another ring. The skeleton may be fused. The other rings mentioned here are the same as those described above for R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 A ring structure formed by bonding together The description can be referred to.

[0115] In one aspect of the present invention, A in general formula (1) 1 and A 2 is an acceptor group. For example, A 1 and A 2 is an acceptor group at position (1a), and has one of the skeletons (1a) to (12b). For explanations and specific examples of the acceptor group, see the above. A in general formula (1) 1 and A 2 The explanation and specific examples of the acceptor group can be referred to. In the following, A 1 and A 2Specific examples of compounds in which is an acceptor group are as follows. Can be used in A 1 and A 2 The compound in which is an acceptor group is as follows: The following examples are not to be construed as limiting. 1 and A 2 Both are "A" Each compound has a structure, and the structure of each compound is specified by individually specifying the "A". . [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0116] In one embodiment of the present invention, the compound represented by general formula (1) is a compound having a rotationally symmetric structure. In one embodiment of the present invention, a compound having a linear symmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, the compound represented by general formula (1) is selected from the group consisting of: A compound with a symmetric structure is selected. Specific examples of compounds having an asymmetric skeleton that can be used in the present invention are listed below. Compounds with symmetrical skeletons or asymmetrical structures are interpreted in a limited manner according to the following specific examples. For specific examples containing X, refer to compounds in which all Xs in the molecule are oxygen atoms. and a compound in which all Xs in the molecule are sulfur atoms, respectively. A compound in which some of the X's in the molecule are oxygen atoms and the rest are sulfur atoms can also be used. do. [ka] [ka] [ka] [ka]

[0117] The following compounds have a symmetrical skeleton but have asymmetrical substituents, resulting in an asymmetric structure: Specific examples of compounds having an asymmetric structure that can be used in the present invention are as follows: The following specific examples should not be construed as limiting. [ka] [ka]

[0118] In one aspect of the present invention, R in general formula (1) 3 is a diarylamino group (diarylamino group The two aryl groups constituting the formula (I) may be bonded to each other. In one embodiment, R in general formula (1) 3 is a hydrogen atom, a deuterium atom, or an acceptor group (not a donor group). In one embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or greater. In a preferred embodiment of the present invention, at least one of m1 and m2 in general formula (1a) is 1 or more. In a more preferred embodiment of the present invention, at least one of n1 to n4 in general formula (1a) one of m1 and m2 in the general formula (1a) is 1 or more, and at least one of m1 and m2 in the general formula (1a) is 1 That's all. In one embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or greater. In a preferred embodiment of the present invention, at least one of m3 and m4 in general formula (1b) is 1 or more. In a more preferred embodiment of the present invention, at least n5 to n8 in general formula (1b) At least one of m3 and m4 in the general formula (1a) is 1 or more. It is greater than or equal to 1. At least one of m1 and m2 is 1 or more, and at least one of m3 and m4 is 1 or more. When one is greater than or equal to 1, R 41 and R 42 At least one of and R 43 and R 44 At least The other is preferably an alkyl group optionally substituted with a deuterium atom, for example, R 41 ~R 44 All of the above n are alkyl groups which may be substituted with a deuterium atom. At least one of n1 to n4 is 1 or more, and at least one of n5 to n8 is 1 or more. One day, Ar 1 ~Ar 4 At least one of and Ar 5 ~Ar 8 At least one of the It is preferably an aryl group which may be substituted with an atom or an alkyl group, for example, Ar 1 ~Ar 8 are all aryl groups optionally substituted with a deuterium atom or an alkyl group. . In one embodiment of the present invention, X in general formula (1) 1 is a boron atom and R 8 , R 10 , R 12 , R 1 3 , R 15 , R 17 When is an alkyl group (or a methyl group), R 1 ~R 7 , R 18 ~ R 20 , R 23 ~R 26 At least one of the groups is a substituent, and is preferably a group of the substituent group E. For example, it is an aryl group which may be substituted with a deuterium atom or an alkyl group. In one embodiment, X in general formula (1) 2 is a boron atom and R 8 , R 10 , R 12 , R 22 , R2 4 , R 26 When is an alkyl group (or a methyl group), R 1 ~R 7 , R 13 ~R 16 , R 19 ~R 21 At least one of these is a substituent, preferably a group of the substituent group E, e.g. For example, it is an aryl group which may be substituted with a deuterium atom or an alkyl group. In one embodiment of the present invention, X in general formula (1) 1 is a boron atom, and R 8 and R 9 , R 9 and R 10 and one pair of R 15 and R 16 , R 16 and R 17 Any one pair of When a cyclic aromatic ring (or benzene ring) is formed, R 1 ~R 7 , R 18 ~R 20 , R 23 ~ R 26 At least one of the groups is a substituent, preferably a group of the substituent group E, for example, deuterium oxide. In one embodiment of the present invention, the aryl group is an aryl group which may be substituted with a hydrogen atom or an alkyl group. X in general formula (1) 2 is a boron atom, and R 8 and R 9 , R 9 and R 10 and one pair of R 22 and R 23 , R 23 and R 24 Any one pair of these bonds together to form an aromatic ring (or benzene ring). When forming R 1 ~R 7 , R 13 ~R 16 , R 19 ~R21 At least one of is a substituent, preferably a group of the substituent group E, and is substituted with, for example, a deuterium atom or an alkyl group. It is an optionally substituted aryl group. In one aspect of the present invention, R in general formula (1) 9 and R 11 is either a cyano group or an alkyl group. There is no R 9 and R 11 is a hydrogen atom, a deuterium atom, or a cyano group and an alkyl group. In one embodiment of the present invention, R in general formula (1) is a substituent other than a methyl group. 9 and R 11 Is, Shi It is neither an ano group nor a tert-butyl group. In a preferred embodiment of the present invention, R in general formula (1) 8 ~R 12 At least one of the groups is a substituent is. In one aspect of the present invention, R in general formula (1) 3 is not a substituted amino group or an aryl group. In one aspect of the invention, R in general formula (1) 3 is not a substituted amino group or a phenyl group. In one embodiment, R in general formula (1) 3 The amino groups are dimethylamino, diphenylamino, and phenyl. It is not a fluorine radical. In a preferred embodiment of the present invention, R in general formula (1) 1 ~R 26 At least one of the groups is a substituent and more preferably R 1 ~R 26 At least one of the groups is an alkyl group, for example, a carbon atom It is an alkyl group having 1 to 4 carbon atoms.

[0119] The molecular weight of the compound represented by the general formula (1) is, for example, If it is intended to use an organic layer formed by vapor deposition, the viscosity should be 1500 or less. It is preferable that the ratio is 1200 or less, more preferable that the ratio is 1000 or less. The lower limit of the molecular weight is preferably 900 or less, and more preferably 900 or less. The molecular weight of the smallest compound in the group of compounds represented by (1) is preferably 624 or more. The compound represented by the general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using this method, it is possible to form a film even from compounds with relatively large molecular weights. The compound represented by formula (1) has the advantage of being easily soluble in organic solvents. The compound represented by formula (1) is easy to apply a coating method and is easy to purify to increase the purity. The compound represented by general formula (1) has high orientation in the film. 1 ~R 7 , R 13 ~R 26 At least one of the groups is a substituent, and preferably R 1 ~R 7 , R 14 ~R 16 , R 19 , R 20 , R 23 ~R 26 at least one of the groups is a substituent; Preferably, the group of Substituent Group E (e.g., an alkyl group which may be substituted with a deuterium atom or an alkyl group) is When the aryl group is a hydroxyl group, the orientation in the film is particularly high. This is preferably exhibited in a film containing a compound represented by general formula (1) together with a substrate material. In addition, such high orientation allows the host material and the delayed fluorescent material acting as an assist dopant to be easily aligned. This is preferably exhibited in a film containing an optical material and a compound represented by general formula (1). By using a compound exhibiting such high orientation, it is possible to provide an organic light-emitting device with high luminous efficiency. The orientation can be evaluated by the orientation value (S value). The larger the negative value, the more The smaller the value, the higher the orientation. The orientation value (S value) is calculated based on the Scientific Report. ts 2017, 7, 8405. The orientation value of the compound represented by formula (1) is preferably less than −0.25, and more preferably less than −0.3 It is more preferable that it is less than 0, and even more preferable that it is less than -0.35, and even more preferable that it is less than -0. It is particularly preferred that it is less than 40.

[0120] By applying the present invention, a compound containing a plurality of structures represented by general formula (1) in the molecule is produced. It may also be used as a material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and then It is considered that the polymer obtained by polymerizing the polymerizable group of the above can be used as a light-emitting material. Specifically, a monomer containing a polymerizable functional group in any of the structures represented by general formula (1) can be used. Prepare a monomer and polymerize it alone or copolymerize it with other monomers. By this method, a polymer having a repeating unit can be obtained, and the polymer can be used as a light-emitting material. Alternatively, compounds represented by general formula (1) can be coupled together. It is also conceivable that dimers or trimers can be obtained by the above method and used as light-emitting materials.

[0121] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include the following general Examples of polymers include those containing a structure represented by the formula: [ka]

[0122] 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, and more preferably 1 to 20. The number of the linking groups is preferably 15, more preferably 2 to 10. 11 -L 11 - represented by Preferably, the compound has the structure: 11 represents an oxygen atom or a sulfur atom and preferably an oxygen atom. 11 represents a linking group, and It is preferably an alkylene group or a substituted or unsubstituted arylene group, and 10 substituted or unsubstituted alkylene groups or substituted or unsubstituted phenylene groups It is more preferable to have one. R 101 , R 102 , R 103 and R 104 each independently represents a substituent. represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, A substituted alkoxy group or a halogen atom is preferable, and an unsubstituted alkyl group having 1 to 3 carbon atoms is more preferable. a fluorine atom, a chlorine atom, an unsubstituted alkoxy group having 1 to 3 carbon atoms, and more preferably or 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 formula (1) is any of the structures constituting Q. Two or more linking groups can be linked to one Q to form a bridged structure. A mesh structure or a network structure may be formed.

[0123] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0124] The polymer having repeating units containing these formulas has any of the structures represented by general formula (1): A hydroxy group is introduced at one of the positions, and the following compound is reacted with it as a linker. The compound can be synthesized by introducing a polymerizable group into the compound and polymerizing the polymerizable group. [ka]

[0125] The polymer containing the structure represented by the general formula (1) in the molecule is The polymer may be a polymer consisting of only repeating units having the same structure, or a polymer consisting of repeating units having other structures. The polymer may contain a repeat unit. The repeating unit having the structure may be of a single type or of two or more types. As the repeating unit not having the structure represented by general formula (1), there are Examples of the monomers include ethylene, styrene, etc. Examples of repeating units derived from a monomer having an ethylenically unsaturated bond include Cut.

[0126] The compound represented by the general formula (1) preferably does not contain a metal atom. The group atoms do not include boron atoms. For example, the compound represented by general formula (1) is It consists of hydrogen, deuterium, nitrogen, oxygen, sulfur and boron atoms. For example, a compound having atoms selected from the group consisting of the general formula (1) As a compound represented by the formula: A compound consisting of atoms selected from the group consisting of boron atoms can be selected. For example, the compound represented by the general formula (1) may contain carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, a compound comprising atoms selected from the group consisting of sulfur atoms and boron atoms; For example, the compound represented by the general formula (1) can be a compound containing carbon atoms, hydrogen atoms, heavy water, A compound consisting of atoms selected from the group consisting of hydrogen atoms, nitrogen atoms, and boron atoms is selected. For example, the compound represented by the general formula (1) can be a compound containing carbon atoms, hydrogen atoms, , nitrogen atoms, oxygen atoms, sulfur atoms, and boron atoms. A compound that can be used in the present invention can be selected.

[0127] In this specification, the "alkyl group" may be straight-chain, branched, or cyclic. In addition, two or more of the straight chain portion, cyclic portion, and branched portion may be mixed. The carbon number of the group can be, for example, 1 or more, 2 or more, or 4 or more. The number can be 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include: The following groups are available: methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl. butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, iso Octyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group Examples of the alkyl group include a cyclobutyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group may be further substituted with an aryl group. The "alkenyl group" may be linear, branched, or cyclic. The alkenyl group may contain two or more of the cyclic and branched moieties. For example, the number of carbon atoms can be 2 or more, 4 or more, and the number of carbon atoms can be 30 or less, 20 or less, 10 or less, or 20 or less. The number of alkyl groups may be 6 or less, or 4 or less. Specific examples of the alkenyl group include an ethenyl group, n-propenyl group, isopropenyl group, n-butenyl group, isobutenyl group, n-pentenyl group hexenyl, isopentenyl, n-hexenyl, isohexenyl, 2-ethylhexenyl The alkenyl group as a substituent may be further substituted with a substituent. good. The "aryl group" and "heteroaryl group" may be a single ring or two or more rings. In the case of a fused ring, the number of fused rings is 2 to 6. It is preferable that the ring is a ring having a ring structure of 2 to 4. benzene ring, pyridine ring, pyrimidine ring, triazine ring, naphthalene ring, anthracene ring, Phenanthrene ring, triphenylene ring, quinoline ring, pyrazine ring, quinoxaline ring, naphthyl ring A tilidine ring may be mentioned, and these may be condensed rings. Specific examples of the heteroaryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1- Anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-pyridyl group, 3 The number of atoms constituting the ring skeleton of the aryl group is It is preferably 6 to 40, more preferably 6 to 20, and is within the range of 6 to 14. The ring skeleton structure of the heteroaryl group may be selected from the group consisting of 1 to 6, or from the group consisting of 6 to 10. The number of atoms is preferably 4 to 40, more preferably 5 to 20, and more preferably 5 to 1 The number of arylene groups may be selected from the range of 4 or from the range of 5 to 10. and "heteroaryl group" refers to the valence in the description of aryl and heteroaryl groups. can be read as 1 to 2.

[0128] As used herein, "substituent group A" refers to a hydroxyl group, a halogen atom (e.g., fluorine), atom, chlorine atom, bromine atom, iodine atom), alkyl group (e.g., carbon number 1 to 40), oxy group (e.g., carbon number 1 to 40), alkylthio group (e.g., carbon number 1 to 40), aryl aryl groups (e.g., carbon numbers 6 to 30), aryloxy groups (e.g., carbon numbers 6 to 30), aryl Thio groups (e.g., carbon atoms of 6 to 30), heteroaryl groups (e.g., ring atoms of 5 to 30) ), heteroaryloxy groups (e.g., rings having 5 to 30 atoms), heteroarylthio groups groups (e.g., ring skeleton atoms of 5 to 30), acyl groups (e.g., carbon atoms of 1 to 40), alkenyl groups alkyl groups (e.g., carbon numbers 1 to 40), alkynyl groups (e.g., carbon numbers 1 to 40), alkoxy groups carbonyl groups (e.g., carbon numbers 1 to 40), aryloxycarbonyl groups (e.g., carbon numbers 1 to 40), heteroaryloxycarbonyl groups (e.g., carbon number 1 to 40), silyl groups (e.g., a trialkylsilyl group having 1 to 40 carbon atoms) and a nitro group; It means a group formed by combining two or more groups. In the present specification, the term "substituent group B" refers to alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups, and the like. oxy group (e.g., carbon number 1 to 40), aryl group (e.g., carbon number 6 to 30), aryloxy group C6-30 alkyl groups, heteroaryl groups (e.g., 5-30 ring atoms) , heteroaryloxy groups (e.g., ring skeletons having 5 to 30 atoms), diarylamino groups one or more groups selected from the group consisting of groups having 0 to 20 carbon atoms It means a group formed by combining. In the present specification, the term "substituent group C" refers to alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups, and the like. aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton) and one selected from the group consisting of diarylamino groups (e.g., having 12 to 20 carbon atoms). The term "a" refers to a group or a group formed by combining two or more groups. In the present specification, the term "substituent group D" refers to alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups, and the like. Heteroaryl groups (e.g., groups with 6 to 22 carbon atoms) and heteroaryl groups (e.g., groups with 5 to 2 atoms in the ring skeleton) 0) or a group formed by combining two or more groups selected from the group consisting of Taste. In the present specification, the term "substituent group E" refers to alkyl groups (e.g., having 1 to 20 carbon atoms) and alkyl groups. one or more groups selected from the group consisting of aryl groups (e.g., having 6 to 22 carbon atoms); It means a group formed by combining. In the present specification, the substitutions described as "substituted" or "substituted or unsubstituted" are The group may be selected from, for example, Substituent Group A or Substituent Group B. The substituents may be selected from the substituent group C, or may be selected from the substituent group D, or It may be selected from group E.

[0129] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In one embodiment, the compound represented by general formula (1) can emit delayed fluorescence. It is a compound. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited in the UV region and the visible spectrum, blue, green, yellow, orange, and red Color region (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 60 It can emit light in the wavelength range of 1000 nm to about 700 nm or in the near-infrared region. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at wavelengths from about 650 nm to about 780 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at wavelengths ranging from about 620 nm to about 590 nm, about 570 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at a wavelength of approximately 510 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at wavelengths of about 475 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is Emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by can be done. In one embodiment of the present disclosure, the compound represented by general formula (1) is Emitting light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by can be done. In one embodiment of the present disclosure, an organic semiconductor device using a compound represented by general formula (1) For example, a CMOS (complementary metal oxide semiconductor) device using the compound represented by general formula (1) can be fabricated. In one embodiment of the present disclosure, a compound having the general formula The compound represented by (1) is used to produce an organic electroluminescence element or a solid-state imaging element (e.g. It is possible to fabricate organic optical devices such as CMOS image sensors.

[0130] The electronic properties of small molecule chemical libraries are quantized by known ab initio methods. For example, the basis is 6-31G* and the The three-parameter Lee-Yang-Parr hybrid functional Hartree-Fock equations using time-dependent density functional theory with functional groups (TD-DFT / B3LYP / 6-31G*) and analyzed the HOMO and and molecular fragments (portions) with a LUMO below a certain threshold. do. This allows for the HOMO energy (e.g., ionization potential) of -6.5 eV or more to be reduced. The donor moiety ("D") can be selected when a valence of 0.5 eV or less is present. The acceptor moiety ("A") is selected when there is a lower LUMO energy (e.g., electron affinity) The bridge portion ("B") can, for example, hold the acceptor and donor moieties in a specific configuration. The strong conjugation between the π-conjugated systems of the donor and acceptor moieties allows for tight confinement. Prevent duplication from occurring. In one embodiment, the compound library is screened using one or more of the following properties: can be. 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 lowest singlet excited state and the lowest triplet excited state at 77 K are Difference (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 In some embodiments, ΔE ST The value is approximately 0.09e V, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 e V, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.0 It is less than 1 eV. In some embodiments, the compound represented by formula (1) is present in an amount of more than 25%, for example about 30%, Approximately 35%, approximately 40%, approximately 45%, approximately 50%, approximately 55%, approximately 60%, approximately 65%, approximately 70%, The quantum yield may be about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0131] [Method for synthesizing the compound represented by general formula (1)] The compound represented by general formula (1) is a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by using a ring-closing reaction or a substitution reaction. It is possible.

[0132] [Constructs using compounds represented by general formula (1)] In one embodiment, the compound represented by general formula (1) is combined with the compound and dispersed therein. , covalently bonded to, coated with, carried or assimilated by the compound. used with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that associate with the compound. For example, the compound represented by the general formula (1) It can be combined with electroactive materials to form films. In some cases, the general formula The compound represented by (1) may be combined with a hole transporting polymer. The compound represented by formula (1) may be combined with an electron transport polymer. The compound represented by general formula (1) is combined with a hole transporting polymer and an electron transporting polymer. In some cases, the compound represented by general formula (1) may be used in combination with a hole transporting moiety and an electron transporting moiety. In the above embodiment, a solid polymer having both a hydroxyl group and a copolymer ... The electrons and / or holes formed in the film or layer are reacted with the compound represented by the general formula (1). The compound can be allowed to interact with the target compound.

[0133] [Film formation] In one embodiment, the film containing the compound represented by general formula (1) of the present invention is produced by a wet process. In the wet process, a solution containing the compound of the present invention is dissolved. The wet process involves applying a coating to a surface, forming a film after removing the solvent. Slit coating method, inkjet method (spray method), gravure printing method, offset printing Examples of the printing method include, but are not limited to, a wet printing method and a flexographic printing method. In this step, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected. In one embodiment, the compound contained in the composition may be one having increased solubility in an organic solvent. A substituent (for example, an alkyl group) can be introduced. In some embodiments, films comprising the compounds of the present invention can be formed by a dry process. In one embodiment, the dry process can be, but is not limited to, vacuum deposition. When using the vacuum deposition method, the compounds that make up the film must be separated into individual layers. Co-evaporation may be performed from a single evaporation source or from a single evaporation source containing a mixture of compounds. When a single evaporation source is used, a mixed powder of compound powders may be used. A compression molded body obtained by compressing the mixed powder of the above may be used, or a mixture obtained by heating and melting each compound and then cooling may be used. In some embodiments, the deposition rates of multiple compounds contained in a single deposition source may be adjusted. By performing co-evaporation under conditions where the weight loss rates are the same or almost the same, It is possible to form a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the film. If a mixture of compounds with the same composition ratio as the film to be deposited is used as the deposition source, the desired In some embodiments, a film having a composition ratio can be easily formed by co-evaporation. The temperature at which each compound loses weight at the same rate was determined and used as the temperature during co-evaporation. It can be used.

[0134] [Examples of use of the compound represented by formula (1)] The compound represented by the general formula (1) is useful as a material for organic light-emitting devices. It is preferably used for photodiodes and the like. Organic Light-Emitting Diode: One aspect of the present invention is a compound represented by general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In one embodiment, the compound of the present invention represented by general formula (1) is can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. The compound represented by the general formula (1) includes a delayed fluorescent material that emits delayed fluorescence. In one embodiment, the present invention provides a delayed fluorescent substance 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 substance. In one embodiment, the present invention relates to a compound represented by general formula (1) as a host material. and can be used with one or more luminescent materials, The material may be a fluorescent material, a phosphorescent material, or a delayed fluorescent material (TADF). The compound represented by formula (1) can also be used as a hole transport material. In this embodiment, the compound represented by general formula (1) can be used as an electron transporting material. In one embodiment, the present invention provides a method for producing delayed fluorescence from a compound represented by general formula (1). In one embodiment, an organic light-emitting device including the compound as a light-emitting material exhibits delayed fluorescence. It emits light and exhibits high light emission efficiency. In one embodiment, the light-emitting layer comprises a compound represented by general formula (1), In some embodiments, the substrate is a film-forming surface. In one embodiment, the compound represented by general formula (1) is The orientation affects the propagation direction of light emitted by the aligning compound, or In one embodiment, the compound represented by general formula (1) Aligning the propagation direction of the emitted light improves the light extraction efficiency from the light emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emissive layer. In one embodiment, the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescent device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescent device (OLED). In one embodiment, the compound represented by general formula (1) is contained in the light-emitting layer. Assisting the light emission of other light-emitting materials (as a so-called assist dopant). The compound represented by general formula (1) contained in the light-emitting layer has the lowest excited singlet energy. The lowest excited singlet energy level of the host material in the emissive layer is at the lowest excited singlet energy level. The lowest excited singlet energy level of the other light-emitting material is included in the formula (1). In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In one embodiment, the organic electroluminescent device comprises at least an anode, a cathode, and In some embodiments, the organic layer comprises at least one light-emitting layer. In some embodiments, the organic layer comprises only an emissive layer. The layer may include one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, ... Examples of the layer include an electron injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer is a hole injection transport layer having a hole injection function. The electron transport layer may be an electron injection transport layer having an electron injection function. An example of an electroluminescent device is shown in FIG.

[0135] Emitting layer: In some embodiments, the light-emitting layer receives holes and electrons injected from the anode and cathode, respectively. recombines to form excitons. In some embodiments, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. The layer comprises an emissive material and a host material. In some embodiments, the emissive material is represented by general formula (1): In some embodiments, the organic electroluminescent device and the organic In order to improve the light emission efficiency of a photoluminescent device, a singlet generated in a light-emitting material is The excitons and triplet excitons are confined within the light-emitting material. In some embodiments, the light-emitting layer In addition to the light-emitting material, a host material is used. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has an excited singlet energy and an excited triplet energy. and at least one of which is higher than those of the luminescent material of the present invention. The singlet excitons and triplet excitons generated in the light-emitting material of the present invention are In some embodiments, the singlet and triplet excitons are trapped in the molecules of the material. In some embodiments, high light emission efficiency is achieved. Although still obtainable, singlet and triplet excitons are not well confined. That is, the host material that can achieve high light emission efficiency is not particularly limited, and can be used in the present invention. In some embodiments, the light-emitting material in the light-emitting layer of the device of the present invention may be In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light comprises light emitted from a host material. In one embodiment, the emitted light is a compound represented by general formula (1) In one embodiment, the emitted light includes the emitted light from the TADF compound and the emitted light from the host material. In some embodiments, TADF is an assist dopant. The singlet energy of the emitting layer is lower than that of the host material in the emitting layer, and the singlet energy of the emitting layer is lower than that of the emitting material in the emitting layer. also has a high excited singlet energy.

[0136] When the compound represented by the general formula (1) is used as an assist dopant, the light-emitting material (preferably Various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of the materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, and pyrene derivatives. , perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, Stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, tafe Nyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacride derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives thiazole derivatives, julolidine derivatives, thiazole derivatives, derivatives containing metals (Al, Zn) These exemplary skeletons may have a substituent, or the like. In addition, these exemplary skeletons may be combined with each other. In the following, a compound in combination with an assist dopant having a structure represented by general formula (1) is Examples of light-emitting materials that can be used are as follows:

[0137] [ka] [ka] [ka] [ka]

[0138] Compounds in which all hydrogen atoms of the above-mentioned exemplary compounds are replaced with deuterium atoms can also be used as host materials. In addition, among the above exemplary compounds, those containing a carbazol-9-yl group can be In this case, a compound in which all hydrogen atoms of the carbazol-9-yl group are replaced with deuterium atoms is also available. It can be used as a steel material. In addition, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 are also The light-emitting material used together with the assist dopant having the structure represented by general formula (1) is Therefore, it can be particularly preferably employed.

[0139] In some embodiments, when a host material is used, the light-emitting material in the light-emitting layer may be a material of the present invention. The amount of the transparent compound is 0.1% by weight or more. In some embodiments, when a host material is used, In this case, the amount of the compound of the present invention contained as a light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the light-emitting material of the present invention contained in the light-emitting layer The amount of the compound is 50% by weight or less. The amount of the compound of the present invention contained as the light-emitting material in the optical layer is 20% by weight or less. In an embodiment, when a host material is used, the compound of the present invention as the light-emitting material contained in the light-emitting layer The amount of the substance is 10% by weight or less. In some embodiments, the host material of the light-emitting layer has hole-transporting and electron-transporting functionality. In some embodiments, the host material of the light-emitting layer is an organic compound that increases the wavelength of emitted light. In some embodiments, the host material of the emissive layer is an organic compound that prevents the formation of a highly vitreous It is an organic compound that has a transition temperature.

[0140] In some embodiments, the host material is selected from the group consisting of: [ka] [ka] In some embodiments, the light-emitting layer comprises two or more structurally distinct TADF molecules. For example, The excited singlet energy levels are higher in the order of the host material, the first TADF molecule, and the second TADF molecule. In this case, the light-emitting layer contains the first TADF molecule and the second TADF molecule. The second TADF molecule has both the lowest excited singlet energy level and the lowest excited triplet energy level at 77 K. Energy level difference ΔE ST is preferably 0.3 eV or less, and more preferably 0.25 eV or less. It is more preferable that the ion concentration is 0.2 eV or less, and it is more preferable that the ion concentration is 0.15 eV or less. It is more preferable that the ion concentration is 0.1 eV or less, and even more preferable that the ion concentration is 0.07 eV or less. It is even more preferable that the α-value is 0.05 eV or less, and even more preferable that the α-value is 0.05 eV or less. It is more preferable that the electron energy is 0.03 eV or less, and it is more preferable that the electron energy is 0.01 eV or less. It is particularly preferred that the concentration of the first TADF molecules in the light-emitting layer is higher than the concentration of the second TADF molecules. In addition, the concentration of the host material in the light-emitting layer is preferably large. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the host It may be greater than, less than, or the same as the concentration of the material. In terms of form, the composition in the light-emitting layer is 10 to 70% by weight of the host material and 10% by weight of the first TADF molecule. In one embodiment, the first TADF molecule may be 0.1 to 30% by weight, and the second TADF molecule may be 0.1 to 30% by weight. The composition in the light-emitting layer is 20 to 45% by weight of the host material and 50 to 75% by weight of the first TADF molecule. In one embodiment, the first TADF molecule may be 5 to 20% by weight. Co-deposited film of F molecules and host material (the concentration of the first TADF molecules in this co-deposited film = A weight The photoluminescence quantum yield φPL1(A) of 100% by photoexcitation and the co-excitation of the second TADF molecule with the host material were Light emission by photoexcitation of the evaporated film (the concentration of the second TADF molecule in this co-evaporated film = A wt%) The quantum yield φPL2(A) satisfies the relation φPL1(A)>φPL2(A). In this embodiment, a co-deposited film of the second TADF molecules and the host material (the second TADF molecules in this co-deposited film) The luminescence quantum yield φPL2(B) due to photoexcitation when the concentration of DF molecules is B% by weight, and the second TAD The luminescence quantum yield φPL2(100) due to photoexcitation of a single film of F molecules is φPL2(B)>φ In one embodiment, the light-emitting layer has three different structures. The compound of the present invention can contain a plurality of TADF molecules contained in the light-emitting layer. It may be any of the compounds. In some embodiments, the light-emitting layer comprises a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer may be made of a material selected from the group consisting of gold. In some embodiments, the light-emitting layer does not contain any carbon, hydrogen, deuterium, or nitrogen atoms. A material consisting only of atoms selected from the group consisting of oxygen atoms and sulfur atoms. Alternatively, the light-emitting layer may be made of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, or the like. The material is composed of atoms selected from the group consisting of oxygen and silicon atoms. Alternatively, the light-emitting layer may be made of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. It may also be made of a material consisting only of atoms selected from the group. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material is Preferred delayed fluorescent materials include those described in WO2013 / 154064. Paragraphs 0008-0048 and 0095-0133 of the publication, WO2013 / 011954 Paragraphs 0007-0047 and 0073-0085 of WO2013 / 01195 No. 5, paragraphs 0007-0033 and 0059-0066, WO2013 / 0810 Paragraphs 0008-0071 and 0118-0133 of Patent Publication No. 88, and JP 2013-256 Paragraphs 0009-0046 and 0093-0134 of Patent Publication No. 490, and JP-A-2013-11 No. 6975, paragraphs 0008-0020 and 0038-0040, WO2013 / 1 No. 33359, paragraphs 0007-0032 and 0079-0084, WO2013 / Paragraphs 0008-0054 and 0101-0121 of Patent Publication No. 161437, and JP 2014 -9352, paragraphs 0007 to 0041 and 0060 to 0069, JP 2014- Paragraphs 0008-0048 and 0067-0076 of Patent Publication No. 9224, and JP 2017-1 Paragraphs 0013 to 0025 of Patent Publication No. 19663, paragraphs 0013 to 0025 of Patent Publication No. 2017-119664 0013 to 0026, paragraphs 0012 to 0025 of JP 2017-222623 A, Paragraphs 0010 to 0050 of JP 2017-226838 A and JP 2018-10041 A Paragraphs 0012 to 0043 of Publication No. 1, and paragraph 0016 of Publication No. WO2018 / 047853 Compounds encompassed by the general formulas described in 1 to 44, particularly exemplary compounds, which are delayed fluorescent compounds In addition, the following are included in the patent documents disclosed in JP 2013-253121 A and W O2013 / 133359, WO2014 / 034535, WO2014 / 115743 publication, WO2014 / 122895 publication, WO2014 / 126200 No. Publication, WO2014 / 136758 Publication, WO2014 / 133121 Publication, WO 2014 / 136860, WO2014 / 196585, WO2014 / 1 89122 publication, WO2014 / 168101 publication, WO2015 / 008580 publication Publications, WO2014 / 203840, WO2015 / 002213, WO2 015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 07 2470 publication, WO2015 / 108049 publication, WO2015 / 080182 publication Patent Publication No. WO2015 / 072537, Patent Publication No. WO2015 / 080183, Patent Publication No. 20 15-129240, WO2015 / 129714, WO2015 / 129 715 publication, WO2015 / 133501 publication, WO2015 / 136880 publication , WO2015 / 137244, WO2015 / 137202, WO201 5 / 137136 publication, WO2015 / 146541 publication, WO2015 / 1595 The luminescent material described in Patent Publication No. 41, which is capable of emitting delayed fluorescence, is preferably used. It should be noted that the above publications mentioned in this paragraph are incorporated herein by reference. Quoted in.

[0141] In the following, each component of the organic electroluminescence element and each layer other than the light-emitting layer We will explain about this.

[0142] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate. The substrate is not particularly limited, and may be any substrate generally used in organic electroluminescence devices. For example, glass, transparent plastic, quartz, and silicon may be used. Either material may be used.

[0143] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, In some embodiments, the conductive material is made from a conductive compound or a combination thereof. Some metals, alloys, or conductive compounds have high work functions (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is C Selected from uI, indium tin oxide (ITO), SnO2 and ZnO. In some embodiments, a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by photolithographic methods. In some embodiments, the pattern does not need to be highly accurate (e.g., about 100 μm). In the case of a pattern having a shape suitable for deposition or sputtering onto an electrode material, In some embodiments, the coating may be formed using a mask, such as an organic conductive compound. When a coating material can be applied, wet film forming methods such as printing and coating methods are used. In some embodiments, when radiation passes through the anode, the anode is 10% The anode has a sheet resistance of less than several hundred ohms per unit area. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. Varies depending on the materials used.

[0144] cathode: In some embodiments, the cathode is a metal with a low work function (4 eV or less) (electrode The electrode is made of an electrode material such as a conductive metal (called an electron-injected metal), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium magnesium 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 and rare earth elements. In some embodiments, the electron-injecting metal and the electron-injecting gold A mixture of the metal and a second metal, which is a stable metal with a higher work function than the metal, is used. In some embodiments, the mixture is a magnesium-silver mixture, a magnesium-aluminum mixture, or a mixture of magnesium and silver. magnesium mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al 2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture provides improved electron injection properties and resistance to oxidation. In some embodiments, the cathode is formed by depositing the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode is formed by forming a In some embodiments, the cathode has a sheet resistance of several hundred ohms or less. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, an organic electroluminescent In some embodiments, either the anode or the cathode of the element is transparent or semi-transparent. In this case, transparent or semi-transparent electroluminescent elements enhance light radiance. In some embodiments, the cathode is made of a conductive, transparent material as described above for the anode. In some embodiments, the cathode is formed from a transparent or semi-transparent material. In the conventional organic light-emitting diode (OLED), the device comprises an anode and a cathode, both of which are transparent or semi-transparent.

[0145] Injection layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer is a drive In some embodiments, the injection layer is a positive electrode. The hole injection layer and the electron injection layer are disposed between the anode and the light emitting layer or the hole transport layer. and between the cathode and the light-emitting layer or the electron-transporting 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.

[0146] [ka]

[0147] Next, examples of preferred compounds that can be used as the electron injection material will be given. [ka]

[0148] Barrier layer: The blocking layer prevents the charges (electrons or holes) and / or excitons present in the light-emitting layer from In some embodiments, the electron barrier layer is a layer that can prevent the electrons from diffusing out of the It exists between the light-emitting layer and the hole-transporting layer and prevents electrons from passing through the light-emitting layer to the hole-transporting layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron-transporting layer, Blocks holes from passing through the light-emitting layer to the electron-transporting layer. The wall layers prevent excitons from diffusing outside the light-emitting layer. The electron blocking layer and the hole blocking layer constitute an exciton blocking layer. The term "layer" or "exciton blocking layer" refers to a layer that has both the functions of an electron blocking layer and an exciton blocking layer. It includes a layer that

[0149] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer. The blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material 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.

[0150] [ka]

[0151] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, the electron blocking layer The layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer comprises: The electron blocking layer is made of a material that increases the probability of recombination of electrons and holes in the light-emitting layer. It may be the same materials as those previously described for the transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0152] [ka]

[0153] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from transporting charges. In some embodiments, the exciton blocking layer is In some embodiments, this allows for efficient confinement of excitons in the In some embodiments, the exciton blocking layer is disposed on the anode side and the light emitting efficiency of the device is improved. adjacent to the light-emitting layer on either side of the cathode and on both sides thereof. When the exciton blocking layer is present on the anode side, the layer is present between the hole transport layer and the light emitting layer; In some embodiments, an exciton blocking layer is located on the cathode side. When the cathode is formed, the layer may be located between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is provided between the anode and the light-emitting layer on the anode side. In some embodiments, the hole injection layer, the electron blocking layer, A blocking layer, hole blocking layer or similar layer may be present between the cathode and an exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer is between the excited singlet energy and at least one of which includes an excited triplet energy of the light-emitting material, higher than the excited triplet energy.

[0154] 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 hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material has one of the following properties: In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials include, but are not limited to, triazole derivatives, oxadiazo azole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, Polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene derivatives Lylanthracene 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.

[0155] [ka] [ka]

[0156] 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 transports 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, carbo Diimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations 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 polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are listed below. do.

[0157] [ka]

[0158] Furthermore, examples of compounds that can be added to each organic layer include: It is conceivable to add it as a material.

[0159] [ka]

[0160] Specific examples of preferred materials that can be used in organic electroluminescence devices However, the materials that can be used in the present invention are limited to the following exemplary compounds. In addition, even if a compound is given as an example of a material having a specific function, It is also possible to use it as a material having other functions.

[0161] device: In some embodiments, the light-emitting layer is incorporated into a device. For example, the device may include , OLED bulbs, OLED lamps, TV displays, computer monitors , including but not limited to mobile phones and tablets. In some embodiments, the electronic device comprises an anode, a cathode, and a The present invention also includes an OLED having at least one organic layer including a light-emitting layer therebetween. In some embodiments, the compositions described herein can be used in OLED or optoelectronic devices. The present invention can be incorporated into various photosensitive or photoactivated devices, such as lasers. In the present invention, the composition is useful for facilitating charge or energy transfer within the device and / or can be useful as a hole transport material. Such devices include, for example, organic light-emitting diodes. Organic integrated circuits (OLEDs), organic field-effect transistors (O-FETs), Organic thin film transistor (O-TFT), organic light emitting transistor (O-LET), organic solar battery (O-SC), organic optical detector, organic photoreceptor, organic magnetic field quencher (field- quench device (O-FQD), light-emitting fuel cell (LEC) or organic laser diode Examples include O-laser.

[0162] Bulb or Lamp: In some embodiments, the electronic device comprises an anode, a cathode, and a gap between the anode and the cathode. It includes an OLED that includes at least one organic layer, including a light-emitting layer. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. The combination of LEDs is a three-color combination (e.g., RGB). , the combination of OLEDs is not red, green or blue (e.g. orange and In some embodiments, the OLED combination is a two-color, four-color, It is a combination of one or more colors. In some embodiments, the device comprises: a first surface having a mounting surface and a second surface opposite thereto, and at least one opening a circuit board defining the At least one OLED on the mounting surface, D is at least one active layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode; At least one OLED having a light-emitting configuration including an organic layer; a housing for the circuit board; At least one connector disposed at an end of the housing, wherein the casing and the connector define a package suitable for attachment to a lighting fixture; It is an OLED light with one connector and one LED. In some embodiments, the OLED light is configured to emit light in multiple directions. In some embodiments, the first direction includes a plurality of OLEDs attached to a circuit board. Some of the light emitted in the reflector is polarized and emitted in a second direction. A projector is used to polarize light emitted in a first direction.

[0163] 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 can be prepared by methods such as, but not limited to, vacuum evaporation. They are deposited onto a substrate using processes such as deposition, evaporation, or chemical vapor deposition (CVD). In one embodiment, the substrate is etched on two sides to provide pixels of unique aspect ratios. The screen (also called a mask) is a photoplate structure useful in is used in the manufacturing process of OLED displays. The design results in very steep, narrow tie bars between pixels vertically and horizontally. This allows for the placement of large, wide-area beveled apertures on the TFT backplane. While optimizing chemical vapor deposition of the This makes it possible to configure the network. Internal pixel patterning allows for three-dimensional display with various aspect ratios in both horizontal and vertical directions. It is possible to construct a 2-dimensional pixel aperture. The use of "stripes" or halftone circles undercuts these particular patterns. Etching in specific areas is prevented until the material is removed from the substrate. The cell area is etched at a similar rate, but its depth is different from the halftone pattern. By changing the size and spacing of the halftone patterns, This allows etching with different passivation rates within the filter, which is necessary to create steep vertical bevels. This allows for deep, localized etching. The preferred material for deposition masks is Invar, which is cut into long thin sheets at steel mills. Invar is a metal alloy that is cold rolled into a shape. Invar is then spun onto a mandrel as a nickel mask. It is not possible to electrodeposit it onto a suitable, low-cost material for forming open areas in a deposition mask. The first method is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel on a substrate. In some embodiments, the screen or display pattern is Lithography (e.g., photolithography and e-beam lithography) In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In a further embodiment, the screen or The display pattern is fabricated using plasma etching.

[0164] Device manufacturing method: OLED displays are generally made by forming a large mother panel, which is then The panels are manufactured by cutting them into cell panels. Usually, Each cell panel is formed on a base substrate with a thin film transistor having an active layer and source / drain electrodes. A thin film transistor (TFT) is formed, a flattening film is applied to the TFT, and pixel electrodes and light-emitting layer, counter electrode and encapsulation layer are sequentially formed and cut from the mother panel. It is formed by OLED displays are generally made by forming a large mother panel, which is then The panels are manufactured by cutting them into cell panels. Usually, Each cell panel is formed on a base substrate with a thin film transistor having an active layer and source / drain electrodes. A thin film transistor (TFT) is formed, a flattening film is applied to the TFT, and pixel electrodes and light-emitting layer, counter electrode and encapsulation layer are sequentially formed and cut from the mother panel. It is formed by

[0165] Another aspect of the present invention provides a method for manufacturing an organic light emitting diode (OLED) display. The method comprises: 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 on each of the display units of the cell panel; The degree, and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example formed of SiNx. The edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film is formed so that the mother panel can be softly cut into individual cell panels. Assist in ensuring this is done. In some embodiments, the thin film transistor (TFT) layer comprises a light-emitting layer, a gate electrode, and , and source / drain electrodes. Each of the plurality of display units has a thin film transistor. a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a thin film transistor (TFT) layer and a light-emitting unit formed on the interface portion. The film is made of the same material as the planarizing film and has the same shape as the planarizing film. In some embodiments, the light-emitting unit comprises a passivation layer and The planarization film between them and the encapsulation layer that covers and protects the light-emitting unit form the TF In some embodiments of the manufacturing method, the organic film is connected to a T layer. It is not connected to the spray unit or the encapsulation layer.

[0166] Each of the organic film and the planarizing film is made of 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. Furthermore, before forming a barrier layer on one surface of the base substrate formed of polyimide, Attaching a carrier substrate made of a glass material to another surface of the base substrate; and separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible It is a powerful display. In some embodiments, the passivation layer is disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is a passivation organic film. In some embodiments, the planarization film is an organic film formed on the planarization layer. The barrier layer is made of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film is used in the manufacture of an OLED display. and the organic film are simultaneously formed. In some embodiments, the organic film is , may be formed at the edge of the barrier layer, so that a portion of the organic film is directly connected to the base. The remaining portion of the organic film contacts the substrate and surrounds the edge of the barrier layer. Touch.

[0167] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and a and an organic light-emitting layer disposed between the electrode and the counter electrode. The pixel electrodes are connected to the source / drain electrodes of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, the pixel An appropriate voltage is applied between the cathode and counter electrodes, causing the organic light-emitting layer to emit light. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit will be referred to as an image-forming unit. The display unit is called a display unit. In some embodiments, the display unit is covered to prevent penetration of external moisture. The encapsulation layer is a thin film encapsulation layer in which organic and inorganic films are alternately laminated. In some embodiments, the encapsulation layer may be formed into a structure comprising multiple thin films. In some embodiments, the interface has a laminated thin-film encapsulation structure. The organic film is disposed at intervals with respect to each of the plurality of display units. In some embodiments, the organic film is a film in which a portion of the organic film is directly based on the base group. the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer. It is formed in the following manner.

[0168] In one embodiment, the OLED display is flexible and formed from polyimide. In some embodiments, the base substrate is a glass material. The adhesive is formed on a carrier substrate formed in step (b), and the carrier substrate is then separated. In some embodiments, the barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of the mother panel, while a barrier layer is formed on each cell. The barrier layer is formed according to the size of the cell panel, thereby reducing the interface between the barrier layers of the cell panel. A groove is formed in the groove portion of each cell panel, and each cell panel can be cut along the groove.

[0169] In some embodiments, the manufacturing method further comprises cutting along the interface. a step of forming a groove in the barrier layer and forming at least a portion of the organic film in the groove; In some embodiments, the TF of each cell panel is The T layer is formed, and the inorganic passivation layer and the organic planarization film are The TFT layer is then covered with a flat film made of, for example, polyimide or acrylic. At the same time as the protective film is formed, the grooves at the interface are filled with, for example, polyimide or The cell panels are covered with an acrylic organic film. When cutting along the grooves, the organic film absorbs the shock that occurs, preventing cracks. That is, all the barrier layers are completely exposed without any organic film. In this case, when each cell panel is cut along the groove at the interface, the resulting impact This increases the risk of cracks being transmitted to the layers. In this case, the grooves at the interface between the barrier layers are covered with an organic film, and the organic film is not present. To absorb the shock that would otherwise be transmitted to the barrier layer, each cell panel is softly cut and the barrier layer is In one embodiment, the grooves of the interface may be covered. The organic film and the planarizing film are spaced apart from each other. If the film and the planarization film are connected to each other as one layer, the planarization film External moisture will not penetrate the display unit through the film and the remaining organic film. The organic film and planarizing film must be installed in a location where the organic film is They are spaced apart from each other so as to be spaced apart from the playing units.

[0170] In some embodiments, the display unit is formed by forming a light-emitting unit. an encapsulation layer disposed on the display unit to cover the display unit; This allows the mother panel to be fully manufactured before it is placed on the carrier that carries the base substrate. The rear substrate is separated from the base substrate. When irradiated onto the base substrate, the carrier substrate is heated to a temperature equal to the thermal expansion coefficient between the carrier substrate and the base substrate. The difference separates it from the base substrate. In some embodiments, the mother panel is cut into cell panels. In an embodiment, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the mother panel is cut along an interface. The grooves in the base are covered with an organic film, which absorbs the impact during cutting. In some embodiments, the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces product defect rates and stabilizes product quality. . Another embodiment is a barrier layer formed on a base substrate and a display formed on the barrier layer. The unit, the encapsulation layer formed on the display unit, and the barrier layer are applied to the edge of the unit. and an organic film formed on the substrate.

[0171] This specification discloses at least the following inventions. [1] A compound represented by the following general formula (1): General formula (1) [ka] [In the general formula (1), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side R 1 ~R 26 , A 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent Represents. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 1 4 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 1 9 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 2 4 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure However, X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form single bonds, and Forming a roll ring, X 2 is a nitrogen atom, R 21 and R 22 are bonded together to form a single bond and form a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 2 1 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 are bonded to each other When a single bond is formed, R 1 ~R 6 At least one of the ants is substituted or unsubstituted. Is it a methyl 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 Noise are bonded to each other to form an aromatic or heteroaromatic ring. [2] The compound according to [1], wherein the compound has the following skeleton (1a) or skeleton (1b): Compound. [ka] [Each hydrogen atom in the skeletons (1a) and (1b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. It is okay.] [3] The compound according to [1], wherein the compound has the following skeleton (2a) or skeleton (2b): Compound. [ka] [Each hydrogen atom in the skeletons (2a) and (2b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. It is okay.] [4] The compound according to [1], wherein the compound has the following skeleton (3a) or skeleton (3b): Compound. [ka] [Each hydrogen atom in the skeletons (3a) and (3b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. It is okay.] [5] The compound according to [1], wherein the compound has the following skeleton (4a) or skeleton (4b): Compound. [ka] [In skeletons (4a) and (4b), Y 1 ~Y 4 are each independently two hydrogen atoms, a single bond or N(R 27 ) and Z 1 ~Z 4each independently represents an oxygen atom or a sulfur atom, , R 27 represents a hydrogen atom, a deuterium atom, or a substituent. In the skeletons (4a) and (4b), Each hydrogen atom in the group may be replaced by a deuterium atom or a substituent, or the adjacent hydrogen atoms The alkyl group may be substituted with a linking group together with the alkyl group to form a cyclic structure. [6] The compound according to [1], wherein the compound has the following skeleton (5a) or skeleton (5b): Compound. [ka] [In skeletons (5a) and (5b), Y 5 ~Y 8 are each independently two hydrogen atoms, a single bond or N(R 27 ) and Z 5 ~Z 8 each independently represents an oxygen atom or a sulfur atom, , R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Each hydrogen atom in the group may be replaced by a deuterium atom or a substituent, or the adjacent hydrogen atoms The alkyl group may be substituted with a linking group together with the alkyl group to form a cyclic structure. [7] The compound according to [1], wherein the compound has the following skeleton (6a) or skeleton (6b): Compound. [ka] [In skeletons (6a) and (6b), Y 9 ~Y 12 are each independently two hydrogen atoms, a single Bond or N(R 27 ) and Z 9 ~Z 16 each independently represents an oxygen atom or a sulfur atom represents R 27 represents a hydrogen atom, a deuterium atom, or a substituent. Skeletons (6a) and (6b) Each hydrogen atom in may be replaced by a deuterium atom or a substituent, and the adjacent hydrogen atoms The atom may be substituted with a linking group to form a cyclic structure.] [8] The compound according to [1], wherein the compound has the following skeleton (7a) or skeleton (7b): Compound. [ka] [In skeletons (7a) and (7b), Y 21 ~Y 24 each independently represents two hydrogen atoms, Single bond or N(R 27 ) and R 27 represents a hydrogen atom, a deuterium atom or a substituent. Each hydrogen atom in the skeletons (7a) and (7b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. That's fine.] [9] The compound according to [1], wherein the compound has the following skeleton (8a) or skeleton (8b): Compound. [ka] [In skeletons (8a) and (8b), Y 25 ~Y 28 each independently represents two hydrogen atoms, Single bond or N(R 27 ) and R 27 represents a hydrogen atom, a deuterium atom or a substituent. Each hydrogen atom in the skeletons (8a) and (8b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. That's fine.]

[10] The compound according to [1], wherein the compound has the following skeleton (9a) or skeleton (9b): compound. [ka] [In skeletons (9a) and (9b), Y 29 ~Y 32 each independently represents two hydrogen atoms, Single bond or N(R 27 ) and R 27 represents a hydrogen atom, a deuterium atom or a substituent. Each hydrogen atom in the skeletons (9a) and (9b) is replaced by a deuterium atom or a substituent. or may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. That's fine.]

[11] The compound according to [1], wherein the compound has the following skeleton (10): Skeleton (10) [ka] [Each hydrogen atom in the skeleton (10) may be substituted with a deuterium atom or a substituent. and the adjacent hydrogen atom may be substituted with a linking group to form a cyclic structure.]

[12] The benzene ring constituting the carbazole partial structure constituting the compound may be substituted or unsubstituted. The compound according to any one of [1] to

[11] , wherein an unsubstituted or unsubstituted aryl group is bonded to the compound. thing.

[13] The compound according to any one of [1] to

[12] , which has a rotationally symmetric structure.

[14] The compound according to any one of [1] to

[12] , which has a linear symmetric structure.

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

[14] .

[16] A film containing the compound according to any one of [1] to

[14] .

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

[14] .

[18] An organic light-emitting device comprising the compound according to any one of [1] to

[14] .

[19] The organic light-emitting device according to

[0018] , wherein the device has a layer containing the compound, the layer also containing a host material.

[20] The layer containing the compound contains a delayed fluorescent material in addition to the host material, The lowest excited singlet energy of the optical material is lower than that of the host material and higher than that of the compound;

[19] The organic light-emitting device according to

[19] .

[21] The element has a layer containing the compound, and the layer is different from the compound. The organic light-emitting device according to

[18] , further comprising a light-emitting material having a structure.

[22] The organic light-emitting device according to any one of

[0018] to

[20] , wherein the compound has the greatest amount of light emission among the materials contained in the device.

[23] The method according to

[20] , wherein the amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound. The organic light-emitting device described above.

[24] The organic light-emitting element according to any one of

[18] to

[23] , which emits delayed fluorescence. child. [Example]

[0172] The following synthesis examples and working examples will further illustrate the features of the present invention. The materials, processing contents, processing procedures, etc. may be changed 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 light emission characteristics were evaluated using a source meter (Keithley: 2400 series), Semiconductor parameter analyzer (Agilent Technologies: E5273A), optical Power meter measuring device (Newport: 1930C), optical spectrometer (Ocean Optic) A spectroradiometer (Topcon: SR-3) and a streamlined The measurement was carried out using a spectrophotometer (Hamamatsu Photonics Co., Ltd., C4334 model). High-performance UV-Vis-NIR spectrophotometer (PerkinElmer: Lambda 950) The orientation value (S value) was measured using a molecular orientation characteristic measuring device (Hamamatsu Photonics K.K.). This was performed using a ion exchanger (C14234-01).

[0173] (Synthesis Example 1) Synthesis of Compound 1 [ka]

[0174] Under a nitrogen atmosphere, carbazole (7.69 g, 46.0 mmol) was dissolved in sodium hydride (1 Add 160 mL of N,N-dimethylformamide solution of 16.16 g (29.0 mmol) of HCl. After stirring at room temperature for 30 minutes, 2,5-dibromo-1,4-difluorobenzene (5. The mixture was added with 1000g of ethanol (18.4mmol) and stirred at 60°C for 16 hours. Water was added, and the precipitated solid was filtered. The resulting solid was purified with toluene and washed with acetonitrile to obtain a white solid. Intermediate A (5.83 g, 10.3 mmol, 56% yield) was obtained. 1 HNMR (400 MHz, CDCl3, δ): 8.19 (d, J = 8.0 Hz, 4H), 8.01 (s, 2H), 7.58-7.48 (m , 4H), 7.39-7.35 (m, 4H), 7.27-7.24 (m, 4H) MS (ASAP): 567.01 (M+H + ). Calcd for. C 30 H 18 Br2N2: 565.98

[0175] [ka]

[0176] Under a nitrogen atmosphere, a solution of intermediate A (1.00 g, 1.80 mmol) in toluene (100 mL ) at -30°C, n-butyllithium (1.6 mol / L hexane solution, 4.5 mL, 7. 19 mmol) was added and stirred at room temperature for 1 hour. The reaction mixture was cooled to -30°C and the tribromide Boron (0.991 g, 3.96 mmol) was added and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-pentamethylpiperidine (0.558 g, 3.60 mmol) The mixture was added and stirred at 120°C for 17 hours. The reaction mixture was cooled to room temperature and 2-mesitylmagnesium was added. tetrahydrofuran solution, 5.4 mL, 5.40 mmol l) was added and the mixture was stirred at room temperature for 2.5 hours. The solvent of the resulting reaction mixture was evaporated, and methanol was The precipitate was filtered off after adding toluene. Compound 1 (0.258 g, 0.388 mmol) was purified with a 4:6 mixture of hexane and hexane to give an orange solid. l, yield 22%). 1 HNMR (400 MHz, CDCl3, δ): 9.26 (s, 2H), 8.52 (d, J= 6.8 Hz, 2H), 8.28-8.21 (m, 4H), 7.94-7.90 (m, 2H), 7.64-7.60 (m, 2H), 7.45-7.42 (m, 4H), 7.15-7.14 (m, 4H) , 2.56 (s, 6H), 2.16 (s, 12H) MS (ASAP): 664.23 (M + ). Calcd for. C 48 H 38 B2N2: 664.32

[0177] (Synthesis Example 2) Synthesis of Compound 2 [ka]

[0178] Under a nitrogen atmosphere, 3,6-diphenylcarbazole (3.00 g, 9.39 mmol) was dissolved in water. Sodium chloride (0.376 g, 9.39 mmol) in N,N-dimethylformamide The mixture was stirred at room temperature for 30 minutes, and then 2,5-dibromo-1,4-difluoromethane was added. Orobenzene (1.02 g, 3.76 mmol) was added and the mixture was stirred at 60°C for 14 hours. The mixture was returned to room temperature, water and methanol were added, and the precipitated solid was filtered. Dissolve in hot toluene, filter through a silica gel pad (toluene), and evaporate the solvent from the filtrate. The obtained solid was washed with acetonitrile to give intermediate B (2.36 g) as a white solid. , 2.71 mmol, 72% yield. 1 HNMR (400 MHz, CDCl3, δ): 8.46-8.44 (m, 4H), 8.10 (s, 2H), 7.79-7.75 (m, 12H), 7.54-7.49 (m, 8H), 7.41-7.35 (m, 8H) MS (ASAP): 870.20 (M + ). Calcd for. C 54 H 34 Br2N2: 870.11

[0179] [ka]

[0180] Under a nitrogen atmosphere, a solution of intermediate B (1.00 g, 1.15 mmol) in toluene (300 mL ) at -30°C, n-butyllithium (1.6 mol / L hexane solution, 2.9 mL, 4. The reaction mixture was cooled to -30°C and the tribromide was added. Boron (0.633 g, 2.53 mmol) was added and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-pentamethylpiperidine (0.357 g, 2.30 mmol) The mixture was added and stirred at 120°C for 17 hours. The reaction mixture was cooled to room temperature and 2-mesitylmagnesium was added. tetrahydrofuran solution, 3.4 mL, 3.40 mm The resulting reaction mixture was added to a silica pad (toluene) and stirred for 4 hours. The filtrate was filtered with a filtration filter, and the solvent was distilled off from the filtrate. Ethyl acetate was added to the resulting viscous mass, and the precipitate was filtered. Compound 2 (0.0710 g, 0.0732 mmol, 6% yield) was obtained as an orange solid. Ta. 1 HNMR (400 MHz, CDCl3, δ): 9.29 (s, 2H), 8.81-8.79 (m, 2H), 8.53-8.52 (m, 2H), 8.46-8.45 (m, 2H), 7.82-7.78 (m, 8H), 7.59-7.36 (m, 14H), 7.20-7.18 (m, 4H), 2.5 9 (s, 6H), 2.22 (s, 12H) MS (ASAP): 968.67 (M + ). Calcd for. C 72 H 54 B2N2: 968.45

[0181] (Synthesis Example 3) Synthesis of Compound 3 [ka]

[0182] Intermediate C Under a nitrogen atmosphere, 3,6-ditert-butyl-9H-carbazole (29.2 g, 105 mm ol), cesium carbonate (61.9 g, 190 mmol) and 2,5-dibromo-1,4-di Fluorobenzene (12.9 g, 47.5 mmol) dissolved in N,N-dimethylformamide The mixture (360 mL) was stirred at 120°C for 17 hours. The mixture was returned to room temperature, water was added, and the mixture was stirred for 17 hours. The precipitated solid was filtered, and the solid was purified by silica gel column chromatography (toluene). The purified solid was recrystallized from toluene / methanol to obtain white solid intermediate C. (17.5 g, 22.1 mmol, 47% yield) was obtained. 1 HNMR (400 MHz, CDCl3, δ): 8.2-8.17 (m, 4H), 7.93 (s, 2H), 7.55-7.52 (m, 4H), 7 .17 (d, J = 8.4 Hz, 4H), 1.49 (s, 36H) MS (ASAP): 791.47 (M+H + ). Calcd for. C 46 H 50 Br2N2: 790.23

[0183] [ka]

[0184] compound 3 Under a nitrogen atmosphere, a solution of intermediate C (2.00 g, 2.52 mmol) in toluene (100 mL ) at -30°C, n-BuLi (1.6 mol / L hexane solution, 4.7 mL, 7.56 m mol) was added and stirred at 50°C for 30 minutes. The reaction mixture was cooled to -30°C and Isopropyl alcohol (3.16 g, 12.6 mmol) was added and the mixture was stirred at room temperature for 30 minutes. , 2,2,6,6-pentamethylpiperidine (1.96 g, 12.6 mmol) was added. The mixture was stirred at 130° C. for 2 hours. 2-mesitylmagnesium bromide (1.0 25.2 mL of 25.2 mmol / L tetrahydrofuran solution was added and the mixture was cooled to room temperature. The resulting reaction mixture was evaporated, and methanol was added. The precipitate was filtered, and the solid was purified by silica gel column chromatography (toluene:hexane The resulting mixture was purified with a 1:9 ethanol / hexanes mixture to give an orange solid, compound 3 (0.292 g, 0.328 mmol, yield 1 3%) was obtained. 1 HNMR (400 MHz, CDCl3, δ): 9.11 (s, 2H), 8.58 (d, J= 2.0 Hz, 2H), 8.25 (d, J = 2.0 Hz, 2H), 8.23 ​​(d, J = 1.6 Hz, 2H), 7.75 (d, J = 9.2 Hz, 2H), 7.44-7.41 (m, 2 H), 7.17 (s, 4H), 2.60 (s, 6H), 2.16 (s, 12H), 1.53-1.51 (m, 36H) MS (ASAP): 888.85 (M + ). Calcd for. C 64 H 70 B2N2: 888.57

[0185] (Synthesis Example 4) Synthesis of Compound 4 [ka]

[0186] compound 4 Compound 3 (250 mg, 0.281 mmol) and N-bromosuccinimide were mixed under a nitrogen atmosphere. A solution of 99.6 mg (0.562 mmol) of dimethylformamide (20 ml) L) is stirred at room temperature for 16 hours. Water is added to the mixture, and the precipitated solid is filtered. This is purified by silica gel column chromatography to give compound 4 as an orange solid.

[0187] (Synthesis Example 5) Synthesis of Compound 5 [ka]

[0188] compound 5 Compound 4 (100 mg, 0.0955 mmol) was dissolved in tetrahydrofuran under a nitrogen atmosphere. n-BuLi (1.6 mol / L hexane solution, 0.13 m Add dimethylmalonate (0.201 mmol) and stir at room temperature for 30 minutes. Add 27.0 mg of benzonitrile (0.287 mmol) and stir at room temperature for 16 hours. The solvent was distilled off from the reaction mixture, and the mixture was purified by silica gel column chromatography to give a red solid compound. Obtain 5 compounds.

[0189] (Synthesis Example 6) Synthesis of Compound 6 [ka]

[0190] compound 6 Under a nitrogen atmosphere, a solution of intermediate C (2.00 g, 2.53 mmol) in toluene (100 mL ) at 0°C. The reaction mixture was cooled to 0°C and the boron tribromide (3 1.16 g, 12.6 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. Add 2,6,6-pentamethylpiperidine (1.96 g, 12.6 mmol) and 135 The mixture was stirred at 0°C for 2 hours. Lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 25.2 mL, 25 0.2 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The solvent was distilled off, methanol was added, and the precipitate was filtered. Purify with toluene / hexane (toluene:hexane = 1:49) and recrystallize with toluene / methanol Compound 6 (0.140 g, 0.328 mmol, 5% yield) was obtained as an orange solid. Ta. 1 HNMR (400 MHz, CDCl3, δ): 9.10 (s, 2H), 8.53 (d, J=1.6 Hz, 2H), 8.27 (d, J=1.6 Hz, 2H), 8.21 (d, J=1.6 Hz, 2H), 7.64 (d, J=8.8 Hz, 2H), 7.36 (dd, J=8.8, 1.6 H z, 2H), 7.27 (s, 4H), 3.17 (sept, J=6.8 Hz, 2H), 2.55 (sept, J=6.8 Hz, 4H), 1.55 (d, J=6.8 Hz, 12H), 1.48 (s, 18H), 1.47 (s, 18H), 1.06 (d, J=6.8 Hz, 12H), 1.01 (d, J=6.8 Hz, 12H). MS (MALDI): 1058.07 (M + ). Calcd for. C 76 H 96 B2N2: 1058.78

[0191] (Synthesis Example 7) Synthesis of Compounds 7 and 8 [ka]

[0192] Intermediate D Under a nitrogen atmosphere, 3-tert-butyl-9H-carbazole (1.8 g, 8.06 mmol) , potassium carbonate (1.78 g, 12.9 mmol) and 2,5-dibromo-1,4-difluoromethane Orobenzene (0.876 g, 3.22 mmol) in N,N-dimethylformamide (50 mL) was stirred at 120°C for 17 hours. The mixture was returned to room temperature, and water was added to precipitate. The solid was filtered and purified by silica gel column chromatography (chloroform:hexane). Purification with hexane (1:4) gave intermediate D (0.44 g, 0.650 mmHg). ol, yield 20%). 1 HNMR (400 MHz, CDCl3, δ): 8.2-8.18 (m, 4H), 7.97 (s, 2H), 7.56 (d, J = 8.4 Hz, 2H), 7.48 (t, J = 8.4 Hz, 2H), 7.35 (t, J = 8.4 Hz, 2H), 7.25-7.18 (m, 6H), 1.4 9 (s, 18H) MS (ASAP): 679.28 (M+H + ). Calcd for. C 38 H 34 Br2N2: 678.11 [ka]

[0193] Compound 7,8 Under a nitrogen atmosphere, a solution of intermediate D (1.90 g, 2.79 mmol) in toluene (100 mL ) at -30°C, n-BuLi (1.6 mol / L hexane solution, 5.23 mL, 8.37 The reaction mixture was cooled to -30°C and the tribromide was added. Boron (3.49 g, 14.0 mmol) was added and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-pentamethylpiperidine (2.17 g, 14.0 mmol) was added to The mixture was stirred at 135°C for 2 hours. Add 27.9 mL of 0.0 mol / L tetrahydrofuran solution (27.9 mmol) and The mixture was stirred for 17 hours while being returned to a warm temperature. The solvent in the resulting reaction mixture was distilled off, and methanol was added. The solid was purified by silica gel column chromatography (toluene:hexane). The compound was purified with a 1:9 ethanol mixture to give an orange solid, compound 7 (0.243 g, 0.313 mmol). Compound 8 (0.313 g, 0.403 mmol, yield 14%) was obtained. compound 7 1 H NMR (400 MHz, CDCl3, δ): 9.21 (s, 2H), 8.52 (dd, J = 9.5, 2.0 Hz, 2H), 8.25 (d, J = 2.0 Hz, 2H), 8.20 (dd, J = 9.5, 2.0 Hz, 2H), 7.81 (d, J = 11.5 Hz, 2H), 7.60 (t, J = 9.5 Hz, 2H), 7.44 (dd, J = 11.5, 9.0 Hz, 2H), 7.16 (s, 4H), 2.57 (s , 6H), 2.15 (s, 12H), 1.51 (s, 18H) MS (MALDI): 776.90 (M + ). Calcd for. C 56 H 54 B2N2: 776.45 compound 8 1 H NMR (400 MHz, CDCl3, δ): 9.21 (s, 1H), 9.16 (s, 1H), 8.58 (d, J = 2.0 Hz, 1H ), 8.52 (d, J = 7.6 Hz, 1H), 8.3-8.24 (m, 3H), 8.19 (d, J= 7.2 Hz, 1H), 7.92-7.8 5 (m, 1H), 7.82-7.75 (m, 1H), 7.60 (t, J= 7.2 Hz, 1H), 7.47-7.39 (m, 3H), 7.19-7 .13 (m, 4H), 2.6-2.55 (m, 6H), 2.17-2.14 (m, 12H), 1.51 (s, 18H) MS (MALDI): 776.98 (M + ). Calcd for. C 56 H 54 B2N2: 776.45

[0194] (Synthesis Example 8) Synthesis of Compound 9 [ka]

[0195] compound 9 Under a nitrogen atmosphere, a solution of intermediate A (1.00 g, 1.77 mmol) in toluene (100 mL ) at -30°C, n-BuLi (1.6 mol / L hexane solution, 3.3 mL, 5.30 m The reaction mixture was cooled to -30°C and stirred at room temperature for 30 minutes. The reaction mixture was stirred at room temperature for 30 minutes. , 2,2,6,6-pentamethylpiperidine (1.37 g, 8.83 mmol) was added. The mixture was stirred at 120° C. for 15 hours. The reaction mixture was returned to room temperature and 2,4,6-triisopropyl Magnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 17.7 mL, 17.7 mmol) was added and the mixture was stirred at 120°C for 4 hours. The mixture was filtered, and the solvent in the filtrate was evaporated. The residue was purified by silica gel column chromatography. The compound 9 (0.12%) was purified with toluene:hexane (15:85) to give an orange solid. 8 g, 0.154 mmol, 9% yield was obtained. 1 H NMR (400 MHz, CDCl3, δ): 9.31 (s, 2H), 8.49 (d, J= 7.2 Hz, 2H), 8.28 (d, J = 7.2 Hz, 2H), 8.25 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 8.4 Hz, 2H), 7.61 (t, J = 7 .6 Hz, 2H), 7.41 (t, J = 7.6 Hz, 2H), 7.38-7.33 (m, 2H), 7.28 (s, 4H), 3.16 (sep t, J = 6.8 Hz, 2H), 2.57 (sept, J = 6.8 Hz, 4H), 1.52 (d, J = 7.2 Hz, 12H), 1.09 (d, J = 6.8 Hz, 12H), 1.04 (d, J = 6.8 Hz, 12H) MS (MALDI): 832.73 (M + ). Calcd for. C 60 H 62 B2N2: 832.51

[0196] (Synthesis Example 9) Synthesis of Compound 10 [ka]

[0197] Intermediate E Under a nitrogen atmosphere, 3-tert-butyl-6-phenyl-9H-carbazole (2.70 g, 9 0.02 mmol), cesium carbonate (5.34 g, 16.4 mmol) and 2,5-dibromo -1,4-Difluorobenzene (1.11 g, 4.10 mmol) N,N-dimethyl fluoride The amide solution (50 mL) was stirred at 120° C. for 15 hours. The mixture was allowed to cool to room temperature. Water was added and the precipitated solid was filtered. This was recrystallized in toluene to give a white solid. Intermediate E (3.06 g, 3.68 mmol, 90% yield) was obtained. 1 HNMR (400 MHz, CDCl3, δ): 8.40 (d, J = 2.0 Hz, 2H), 8.23 ​​(d, J = 1.6 Hz, 2H), 8.02 (s, 2H), 7.79-7.76 (m, 4H), 7.73 (dd, J = 8.8, 1.6 Hz, 2H), 7.59 (dd, J = 8 .4, 1.6 Hz, 2H), 7.53-7.48 (m, 4H), 7.41-7.35 (m, 2H), 7.31 (d, J = 7.6 Hz, 2H), 7.23 (d, J = 8.8 Hz, 2H), 1.50 (s, 18H) MS (ASAP): 831.43 (M+H + ). Calcd for. C 50 H 42 Br2N2: 830.17 [ka]

[0198] compound 10 Under a nitrogen atmosphere, a solution of intermediate E (1.00 g, 1.21 mmol) in toluene (100 mL ) at -30°C, n-BuLi (1.6 mol / L hexane solution, 2.27 mL, 3.63 The reaction mixture was cooled to -30°C and the tribromide was added. Boron (1.52 g, 6.05 mmol) was added and the mixture was stirred at room temperature for 30 minutes. 1,2,2,6,6-pentamethylpiperidine (0.939 g, 6.05 mmol) The mixture was stirred at 135° C. for 2 hours. Sium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 12. 1 mL, 12.1 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The solvent was distilled off from the mixture, methanol was added, and the precipitate was filtered. The residue was purified by column chromatography (toluene:hexane = 1:9) and then toluene / methanol Compound 10 (0.364 g, 0.332 mmol) was obtained as an orange solid by recrystallization at 2000 K. The result was a 27% success rate. 1 H NMR (400 MHz, CDCl3, δ): 9.24-9.19 (m, 2H), 8.62-8.60 (m, 2H), 8.50-8.47 (m, 2H), 8.35-8.32 (m, 2H), 7.85-7.69 (m, 6H), 7.64-7.60 (m, 2H), 7.56-7.46 (m, 4H) , 7.45-7.35 (m, 2H), 7.31 (s, 4H), 3.23-3.16 (m, 2H), 2.65-2.56 (m, 4H), 1.60-1. 55 (m, 18H), 1.51-1.48 (m, 12H), 1.14-1.02 (m, 24H) MS (MALDI): 1098.09 (M+H + ). Calcd for. C 80 H 86 B2N2: 1096.70

[0199] (Synthesis Example 10) Synthesis of Compound 11 [ka]

[0200] compound 11 Under a nitrogen atmosphere, a solution of compound D (2.00 g, 2.12 mmol) in toluene (100 mL ) at 0°C. The reaction mixture was cooled to 0°C and stirred at 50°C for 30 minutes. 1.65 g, 10.6 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. , 6,6-pentamethylpiperidine (1.64 g, 10.6 mmol) was added and the mixture was heated at 135°C. The reaction mixture was stirred at rt for 2 hours. Bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 12.7 mL) , 12.7 mmol) was added, and the mixture was stirred for 17 hours while returning to room temperature. The solvent was distilled off, methanol was added, and the precipitate was filtered. The compound was purified by chromatography (chloroform:hexane = 5:95) to give an orange solid, Compound 11. (0.250 g, 0.265 mmol, 13% yield) MS (ASAP): 944.91 (M + ). Calcd for. C 68 H 78 B2N2: 944.64

[0201] (Synthesis Example 11) Synthesis of Compound 12 [ka]

[0202] Compound F Under a nitrogen atmosphere, 3,6-diisopropyl-9H-carbazole (10.0 g, 39.8 m mol), cesium carbonate (23.6 g, 72.3 mmol) and 2,5-dibromo-1,4 -Difluorobenzene (4.92 g, 18.1 mmol) in N,N-dimethylformamide The solution (100 mL) was stirred at 150°C for 17 hours. The mixture was allowed to cool to room temperature, and water was added. The precipitated solid was filtered and purified by silica gel column chromatography (toluene The resulting solid was recrystallized from toluene / methanol. This gave compound F (5.60 g, 7.62 mmol, yield 42%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.01 (d, J = 1.2 Hz, 4H), 7.93 (s, 2H), 7.35 (dd, J= 8.4 Hz, 1.2 Hz, 4H), 7.15 (d, J = 8.4 Hz, 4H), 3.20-3.10 (m, 4H), 1.42-1.39 (m, 24H) MS (ASAP): 735.10 (M+H + ). Calcd for. C 42 H 42 Br2N2: 734.17

[0203] [ka]

[0204] compound 12 Under a nitrogen atmosphere, a solution of compound F (3.00 g, 4.08 mmol) in toluene (150 mL ) at 0°C. The reaction mixture was cooled to 0°C and boron tribromide (5. 11 g, 20.4 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. 6,6-Pentamethylpiperidine (3.17 g, 20.4 mmol) was added and the mixture was heated at 135°C. The reaction mixture was stirred for 3 hours. romide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 40.8 mL) 40.8 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene:hexane This was purified with a toluene / methanol ratio of 5:95 and recrystallized from toluene / methanol to give compound 1, an orange solid. 2 (0.106 g, 0.106 mmol, 3% yield) was obtained. MS (ASAP): 1000.81 (M + ). Calcd for. C 72 H 86 B2N2: 1000.70

[0205] (Synthesis Example 12) Synthesis of Compound 13 [ka]

[0206] Compound G Under a nitrogen atmosphere, 3,6-dimethyl-9H-carbazole (5.00 g, 25.6 mmol) ), cesium carbonate (15.2 g, 46.6 mmol) and 2,5-dibromo-1,4-difluoromethane Fluorobenzene (3.16 g, 11.6 mmol) in N,N-dimethylformamide (50 mL) was stirred at 150°C for 17 hours. The mixture was returned to room temperature, water was added, and the mixture was precipitated. The solid was filtered and purified by silica gel column chromatography (toluene: hexachloroisothiazolinone). The resulting solid was recrystallized from o-dichlorobenzene / methanol. This gave compound G (5.48 g, 8.80 mmol, yield 76%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 7.95 (s, 2H), 7.93 (d, J = 1.2 Hz, 4H), 7.29 (dd, J = 8.4 Hz, 1.2 Hz, 4H), 7.12 (d, J = 8.4 Hz, 4H), 2.72 (s, 12H) MS (ASAP): 623.04 (M+H+ ). Calcd for. C 34 H 26 Br2N2: 622.04

[0207] [ka]

[0208] compound 13 Under a nitrogen atmosphere, a solution of compound G (2.00 g, 3.21 mmol) in toluene (200 mL ) at 0°C. l) was added and stirred at 50°C for 1 hour. The reaction mixture was cooled to 0°C and boron tribromide (4. 02g, 16.1mmol) was added and stirred at room temperature for 1 hour. 6,6-Pentamethylpiperidine (2.50 g, 16.1 mmol) was added and the mixture was heated at 135°C. The reaction mixture was stirred for 3 hours. romide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 32.1 mL) 32.1 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene:hexane This was purified with a toluene / methanol ratio of 5:95 and recrystallized from toluene / methanol to give compound 1, an orange solid. 3 (0.270 g, 0.304 mmol, 9% yield) was obtained. MS (ASAP): 888.59 (M + ). Calcd for. C 64 H 70 B2N2: 888.57

[0209] (Synthesis Example 13) Synthesis of Compound 14 [ka]

[0210] compound 14 Under a nitrogen atmosphere, a solution of compound A (2.26 g, 2.86 mmol) in toluene (100 mL ) at 0°C. l) was added and stirred at 50°C for 1 hour. The reaction mixture was cooled to 0°C and boron tribromide (3. The reaction mixture was added with 1,2,2, 6,6-Pentamethylpiperidine (2.22 g, 14.3 mmol) was added and the mixture was heated at 135°C. The mixture was stirred for 3 hours. 2,6-diisopropylphenylmagnesium bromide was added to the reaction mixture. -Lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 28.6 mL, 28. 6 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The residue was purified by silica gel column chromatography (toluene:hexane=5: 95) and recrystallized from toluene / methanol to give compound 14 (0 0.198 g, 0.203 mmol, 7% yield was obtained. MS (ASAP): 972.64 (M + ). Calcd for. C 70 H 82 B2N2: 972.67

[0211] (Synthesis Example 14) Synthesis of Compound 15 [ka]

[0212] compound 15 Under a nitrogen atmosphere, compound D (1.40 g, 1.77 mmol) was dissolved in toluene (70 mL). At 0°C, n-BuLi (1.6 mol / L hexane solution, 3.3 mL, 5.31 mmol) ) was added and stirred at 50°C for 30 minutes. The reaction mixture was cooled to 0°C and boron tribromide (2. 21 g, 8.85 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. , 6,6-pentamethylpiperidine (1.37 g, 8.85 mmol) was added and the mixture was heated at 135°C. The reaction mixture was stirred at rt for 3 hours. Lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 17.7 mL, 17 0.7 mmol) was added and the mixture was stirred for 17 hours while returning to room temperature. The residue was purified by silica gel column chromatography (toluene:hexane=5 :95) and recrystallized from toluene / methanol to give compound 15( The obtained product was 0.100 g, 0.116 mmol, 7% yield. MS (ASAP): 861.82 (M+H + ). Calcd for. C 62 H 66 B2N2: 860.54

[0213] (Synthesis Example 15) Synthesis of Compound 16 [ka]

[0214] Compound I Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (2.00 g, 5.9 8 mmol), compound H (0.74 g, 2.72 mmol), cesium carbonate (3.54 g , 10.87 mmol) in N,N-dimethylformamide (30 mL) at 140 °C The mixture was stirred for 17 hours, cooled to room temperature, and water (120 mL) was added. The precipitate was filtered and dissolved in methanol. The resulting solid was purified by silica gel column chromatography (toluene:hexane). Compound I (1.648 g, 1.83 mmol, 67%) was obtained. . 1 H-NMR (400 MHz, CDCl3, δ): 8.42 (s, 1H), 7.73 (d, J = 7.8 Hz, 2H), 7.71 (d, J = 3.2 Hz, 1H), 7.41 (q, J = 8.1 Hz, 2H), 7.35 (q, J = 7.9 Hz, 2H), 7.24-7.15 (m, 12H), 7.11 (d, J = 7.3 Hz, 10H), 7.08-7.00 (m, 7H), 6.94 (t, J = 7.1 Hz, 5H). MS (ASAP): 901.20 (M+H + ). Calcd for. C 54 H 36 Br2N4: 900.13.

[0215] [ka]

[0216] compound 16 Under a nitrogen atmosphere, a solution of compound I (0.80 g, 0.89 mmol) in toluene (40 mL ) at 0°C, n-BuLi (1.6 mol / L hexane solution, 1.63 mL, 2.67 m mol) was added and stirred at 50° C. for 30 minutes. The reaction mixture was cooled to 0° C. and boron tribromide was added. (1.13 g, 4.44 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. Add 2,2,6,6-pentamethylpiperidine (0.670 g, 4.44 mmol) The mixture was stirred at 120°C for 2 hours. 1 / L tetrahydrofuran solution, 6.0 mL, 6.00 mmol) was added and the mixture was left to cool overnight. The reaction mixture was filtered through a silica gel pad, and the filtrate was concentrated. The compound was purified by column chromatography (chloroform:hexane = 1:4) to give compound 16. (150 mg, 0.150 mmol, 17%) was obtained. 1 H-NMR (400 MHz, CDCl3, δ): 9.85 (s, 1H), 8.74 (d, J= 8.6 Hz, 2H), 8.36 (d, J = 3.4 Hz, 1H), 7.97 (d, J = 7.9 Hz, 2H), 7.80 (d, J = 7.6 Hz, 2H), 7.59 (t, J = 7 .3 Hz, 1H), 7.42-7.40 (m, 2H), 7.23-7.15 (m, 15H), 7.05-6.94 (m, 8H), 6.80 (s, 4 H), 2.36 (s, 6H), 1.97 (s, 12H). MS (ASAP): 999.52 (M+H + ). Calcd for. C 72 H 56 B2N4: 998.47. A toluene solution of the synthesized compound 16 was prepared and the molar absorption coefficient was measured. This molar extinction coefficient is R in general formula (1). 3 The photoluminescence intensity of the toluene solution was significantly higher than that of the substituted compound. The fluorescence quantum yield was measured and a high value of 94% was obtained.

[0217] (Synthesis Example 16) Synthesis of Compound 17 [ka]

[0218] Compound J 1,5-dibromo-2,4-difluorobenzene (1.30 g, 3.91 mmol), Compound J (0.53 g, 1.96 mmol), cesium carbonate (1.91 g, 5.88 mmol), ol) was dissolved in N-methyl-2-pyrrolidone (39 mL) and stirred at 140°C for 16 hours. Water (120 mL) was added to the reaction mixture, and the precipitate was filtered and washed with methanol. The obtained solid was purified by silica gel chromatography (toluene:hexane=1:2). Compound K (0.47 g, 0.53 mmol, 27%) was obtained. 1 H-NMR (400 MHz, CDCl3, δ): 8.27-8.24 (m, 4H), 7.84 (d, J= 0.9 Hz, 1H), 7.67 (t , J = 8.0 Hz, 1H), 7.62 (d, J = 7.8 Hz, 1H), 7.45-7.28 (m, 15H), 7.24-7.16 (m, 4 H), 7.08 (td, J = 4.7, 2.0 Hz, 2H), 6.86 (d, J = 7.8 Hz, 1H), 6.82 (d, J = 8.2 H z, 1H), 6.56 (dd, J = 8.2, 3.2 Hz, 2H). MS (ASAP): 895.20 (M+H + ). Calcd for. C 54 H 32 Br2N4: 894.10.

[0219] [ka]

[0220] compound 17 Under a nitrogen atmosphere, a solution of compound K (0.47 g, 0.52 mmol) in toluene (24 mL ) at 0°C, n-BuLi (1.6 mol / L hexane solution, 0.98 mL, 1.57 m mol) was added and stirred at 50° C. for 30 minutes. The reaction mixture was cooled to 0° C. and boron tribromide was added. (0.656 g, 2.62 mmol) was added to the reaction mixture and stirred at room temperature for 30 minutes. , 2,2,6,6-pentamethylpiperidine (0.407 g, 2.62 mmol) was added. The mixture was stirred at 120°C for 2 hours. 1 / L tetrahydrofuran solution (3.14 mL, 3.14 mmol) was added and the mixture was left overnight. The reaction mixture was allowed to cool, filtered through a silica gel pad, and the filtrate was concentrated. Compound 17 was purified by gel column chromatography (toluene:hexane=1:9). (68.4 mg, 0.069 mmol, 13%) was obtained. 1 H-NMR (400 MHz, CDCl3, δ): 9.96 (s, 1H), 8.82 (d, J= 8.4 Hz, 2H), 8.58 (s, 1H) , 8.30-8.25 (m, 8H), 7.72-7.68 (m, 2H), 7.64 (t, J = 7.9 Hz, 2H), 7.41-7.35 (m, 6H), 7.29 (t, J= 3.8 Hz, 4H), 7.13-7.08 (m, 2H), 6.91 (d, J = 7.5 Hz, 2H), 6.88 (s, 4H), 2.41 (s, 6H), 2.06 (s, 12H). MS (ASAP): 994.51 (M + ). Calcd for. C 72 H 52 B2N4: 994.45. The compounds synthesized in the synthesis examples were purified by sublimation before being used for the following purposes.

[0221] (Example 1) Preparation of thin film and evaluation of luminescence properties Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Compound 2 and mC BP and Compound 2 were evaporated from different evaporation sources, and a thin film with a concentration of 0.5 wt% was formed at 100 nm. It was formed to a thickness of m. Instead of compound 2, compounds 1, 7, 8, 9, and 11 were used, and the same procedure was repeated for each thin film. A membrane was obtained. When each thin film was irradiated with 300 nm excitation light, The photoluminescence quantum yield (PLQY) of each thin film was measured. The PLQY values ​​are shown in the table below. All the thin films showed high PLQY. [Table 2]

[0222] (Example 2) Preparation of thin film and evaluation of orientation Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Under conditions below Pa, Host1 and Host2 were delayed. Fluorescent material 1 and compound 6 were evaporated from different evaporation sources, and the concentration of Host 1 was 64.5 wt%. A thin film containing delayed fluorescent material 1 at a concentration of 35.0 wt % and compound 6 at a concentration of 0.5 wt % was prepared. The compound 2, 3, 7, 8, 10, and 11 were used instead of the compound 6. Each thin film was obtained in the same manner using each of the above. Separately, a vacuum of 1×10 was deposited on a quartz substrate by vacuum deposition. -3 Under conditions of less than Pa Host 1, delayed fluorescent material 2, and compound 6 were evaporated from different evaporation sources. 64.5% by weight, the concentration of delayed fluorescent material 2 was 35.0% by weight, and the concentration of compound 6 was 0.5% by weight. % thin film was formed to a thickness of 100 nm. A thin film was obtained in the same manner. Furthermore, separately from this, a vacuum of 1×10 was deposited on a quartz substrate by vacuum deposition. -3 Conditions below Pa In this condition, Host 1, delayed fluorescent material 2, and compound 6 were evaporated from different evaporation sources. The concentration of delayed fluorescent material 2 was 54.5% by weight, the concentration of delayed fluorescent material 2 was 45.0% by weight, and the concentration of compound 6 was 0. A thin film containing 5% by weight of the compound 6 was formed to a thickness of 100 nm. , 8, and 10 were used to obtain thin films in the same manner. Furthermore, separately from this, a vacuum of 1×10 was deposited on a quartz substrate by vacuum deposition. -3 Conditions below Pa In this condition, Host 1, delayed fluorescent material 3, and compound 6 were evaporated from different evaporation sources. The concentration of delayed fluorescent material 3 was 54.2% by weight, the concentration of delayed fluorescent material 3 was 45.0% by weight, and the concentration of compound 6 was 0. A thin film containing 8% by weight of the compound 6 was formed to a thickness of 100 nm. , 11 were used to obtain thin films in the same manner. For each of the prepared thin films, the orientation value (S value) of the compound represented by general formula (1) was measured. The results are shown in the table below. Compounds 2, 3, 6, 7, 8, 10, and 11 were particularly good. Good orientation was observed. [Table 3]

[0223] (Example 3) Fabrication and evaluation of organic electroluminescence device Glass with an anode made of 100 nm thick indium tin oxide (ITO) Each thin film was deposited on the substrate by vacuum deposition at a vacuum of 1 x 10 -5 First, ITO HATCN was formed on the substrate to a thickness of 10 nm, and NPD was formed on the substrate to a thickness of 30 nm. Then, EBL1 was formed to a thickness of 10 nm. Mixture 2 was co-evaporated from different evaporation sources to form a 40 nm thick light-emitting layer. The contents of delayed fluorescent material 3 and compound 2 were 54.2 wt %, 45.0 wt %, and 0.8 wt %, respectively. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-T RZ was co-evaporated from different evaporation sources to form a 30 nm thick layer. The contents of Liq and SF3-TRZ were set to 30 wt% and 70 wt%, respectively. Form a 2 nm thick film, then evaporate aluminum (Al) to a thickness of 100 nm. A cathode was formed by the above process to prepare an organic electroluminescence device. The same procedure was carried out using compounds 1, 6, 11, 13, and 15 instead of compound 2. Each organic electroluminescence device was fabricated. The change was that the emitting layer was formed from delayed fluorescent material 1 (55 wt%) and delayed fluorescent material 3 (45 wt%). An organic electroluminescence element of Comparative Example 1 was produced in the same manner, except for changing the materials. When a current was applied to each organic electroluminescence element, light emission was observed from each element. In the device using the compound represented by general formula (1), among the materials contained in the light-emitting layer, The compound represented by general formula (1) emitted the largest amount of light. 6.3mA / cm of the emission element 2 The external quantum efficiency (EQE) was measured. The values ​​are shown in the table below as relative values, with the EQE of the organic electroluminescence element of Comparative Example 1 being 1. The organic electroluminescence device using the compound of general formula (1) is The organic electroluminescence (EL) using the compound of general formula (1) showed a high EQE. The element also had good durability.

[0224] [Table 4]

[0225] (Example 4) Preparation and evaluation of organic electroluminescence devices using different delayed fluorescent materials The delayed fluorescent material 3 in the light-emitting layer of Example 3 was replaced with the delayed fluorescent material 1, and the composition of the light-emitting layer was changed to Host 1, the contents of delayed fluorescent material 1 and compound 2 are 64.5 wt%, 45.0 wt%, and 0.5 wt%, respectively. The other steps were the same as in Example 3. The device was fabricated. Instead of compound 2, compounds 5, 6, and 7 were used to prepare the respective organic electrets in the same manner. A luminescence element was fabricated. The only change was that an emitting layer consisting of delayed fluorescent material 3 (35% by weight) was formed. Similarly, an organic electroluminescence element of Comparative Example 2 was produced. When a current was applied to each organic electroluminescence element, light emission was observed from each element. In the device using the compound represented by general formula (1), among the materials contained in the light-emitting layer, The compound represented by general formula (1) emitted the largest amount of light. 6.3mA / cm of the emission element 2 The external quantum efficiency (EQE) was measured. The values ​​are shown in the table below as relative values, with the EQE of the organic electroluminescence element of Comparative Example 2 being 1. The organic electroluminescence device using the compound of general formula (1) exhibits delayed fluorescence. Even when material 1 was used instead, all of them showed high EQE. The organic electroluminescence device using the compound also had good durability.

[0226] [Table 5]

[0227] [ka] [Explanation of symbols]

[0228] 1 Base material 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1): General formula (1) 【Chemistry 1】 [In the general formula (1), X １ is a nitrogen atom, and X ２ is a boron atom. １ ~R １ ６ and R １９ ~R ２６ each independently represents a hydrogen atom, a deuterium atom, or a substituent; The substituent is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R is a group. ８ ~R １２ At least one of and R ２２ ~R ２６ At least one of R is the above-mentioned substituent. ３ and R ６ and R １５ and R ２０ of At least one of them is independently a substituted or unsubstituted alkyl group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R 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 teeth None of them are bonded to each other to form a cyclic structure. １７ and R １８ are joined together to form a single bond The bond forms a pyrrole ring. １ and A ２ are each independently a hydrogen atom or a deuterium atom However, general formula (1) does not include the following structures: 【Chemistry 2】 【Transformation 3】 【change】

2. R ３ and R ６ are each independently a substituted or unsubstituted alkyl group according to claim 1 . Compound.

3. R ３ , R ６ , R １５ , R ２０ are each independently a substituted or unsubstituted alkyl group, The compound according to claim 2.

4. R ８ and R １２ 10. The compound of claim 1, wherein each independently is said substituent.

5. R ８ , R １２ , R ２２ , R ２６ are each independently the substituent. thing.

6. R ８ ~R １２ Three or more of the above and R ２２ ~R ２６ three or more of the following are each independently the above-mentioned substituents; The compound of claim 1.

7. The compound of claim 1 having a rotationally symmetric structure.

8. A light-emitting material comprising the compound according to any one of claims 1 to 7.

9. A film comprising the compound according to any one of claims 1 to 7.

10. An organic semiconductor device comprising the compound according to any one of claims 1 to 7.

11. An organic light-emitting device comprising the compound according to any one of claims 1 to 7.

12. The device has a light-emitting layer containing a host material, a delayed fluorescent material, and the compound. The organic light-emitting device according to claim 11 , wherein the compound emits the largest amount of light among all the materials.

13. The organic light-emitting device according to claim 11, which emits delayed fluorescence.

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