Compound, light-emitting material, delayed fluorescent body, and organic light-emitting element

Abstract

To provide a compound with excellent light-emitting characteristics.SOLUTION: A compound of the general formula in the figure is provided. In the formula, R1 is H or D; one of R2 and R3 is a triazinyl group or the like substituted with Ar3 and Ar4; two of R4, R5 and the other of R2 and R3 are donor groups, and the remaining one of them is an aryl group; and Ar1 to Ar4 are each an aryl or heteroaryl group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound having a skeleton in which a triazine ring and a benzene ring are bonded, and a light-emitting material and a delayed fluorescent material using the compound. The present invention also relates to an organic light-emitting device such as an organic electroluminescence device using the compound. [Background technology]

[0002] Organic light-emitting elements are light-emitting elements using organic materials, and have been attracting attention in recent years because they can be manufactured by coating and do not use rare elements. Among them, organic electroluminescence elements (organic EL elements) have the advantage that they can be made into lightweight and flexible elements because they emit light by themselves and do not require a backlight. They also have the characteristics of fast response and high visibility, and are expected to be next-generation light sources. For this reason, research on the development of materials useful for organic light-emitting elements, including organic electroluminescence elements, is being actively carried out. In particular, research on light-emitting materials is being actively conducted. Fluorescent materials, phosphorescent materials, and fluorescent materials have long been known as light-emitting materials, but fluorescent materials have the problem of low luminous efficiency, and phosphorescent materials have the problem of being expensive and difficult to emit deep blue light because they contain rare metals. In recent years, delayed fluorescent materials have been developed as light-emitting materials that address these issues.

[0003] A delayed fluorescent material is a material that emits fluorescence when it returns from an excited singlet state to a ground state after reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state. Fluorescence by such a route is observed later than fluorescence from an excited singlet state directly generated from a ground state (normal fluorescence), and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency only by fluorescence from an excited singlet state directly generated. On the other hand, in a delayed fluorescent material, not only an excited singlet state but also an excited triplet state can be used for fluorescence emission by a route via the above-mentioned reverse intersystem crossing, and therefore a higher luminous efficiency can be obtained than that of a normal fluorescent material.

[0004] Since this principle was clarified, various delayed fluorescent materials have been discovered through various researches. Many of these materials include compounds in which a donor group and an acceptor group are substituted on a benzene ring. For example, it has been proposed to use a compound having a skeleton in which a carbazol-9-yl group, which is a donor group, and a cyano group and a substituted triazinyl group, which are acceptor groups, are substituted on a benzene ring in an organic light-emitting element (see Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2019 / 191665A1 Summary of the Invention [Problem to be solved by the invention]

[0006] Even if a material emits delayed fluorescence, one that has extremely good properties and has no practical problems has not yet been provided. Therefore, if a delayed fluorescent material with even better properties could be provided, it would be even more useful. However, the improvement of delayed fluorescent materials is still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful luminescent material.

[0007] Under such circumstances, the present inventors have conducted extensive research with the aim of providing a compound more useful as a delayed fluorescent material for a light-emitting device. They have then conducted intensive research with the aim of deriving and generalizing a general formula for a compound more useful as a delayed fluorescent material, and using such a compound in an organic light-emitting device. [Means for solving the problem]

[0008] As a result of intensive research to achieve the above object, the present inventors have found that a compound having a structure that satisfies certain conditions is useful as a light-emitting material and makes it possible to provide an excellent organic light-emitting device. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] A compound represented by the following general formula (1): [ka] [In the general formula (1), R 1 R represents a hydrogen atom or a deuterium atom. 2 and R 3 One of the groups is represented by the following general formula (2), R 2 and R 3 and R 4 and R 5 Two of the groups selected from the group consisting of are donor groups, and the remaining one is a substituted or unsubstituted aryl group. 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. [ka] In the general formula (2), X 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of the groups is N. R represents a hydrogen atom, a deuterium atom, or a substituent. Ar 3 and Ar 4 Each of L independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 represents a single bond or a divalent linking group. * represents the bonding position.] [2] R 2 is a group represented by general formula (2). [3] R 3 is a group represented by general formula (2). [4] Ar 1 ~Ar 4 The compound according to any one of [1] to [3], wherein one or more of the groups represented by the formula (I) are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups). [5] Ar 1 ~Ar 4 is a heteroaryl group having a 5-membered ring bonded to a nitrogen atom. [6] The compound according to any one of [1] to [5], wherein the donor group is a substituted or unsubstituted carbazol-9-yl group. [7] The compound according to any one of [1] to [6], wherein the donor group is a donor group having a fused ring structure with four or more rings. [8] R 5

[0026] The compound according to any one of [1] to [7], wherein [9] R 4 is a substituted or unsubstituted aryl group.

[10] The compound according to any one of [1] to [9], wherein the substituted or unsubstituted aryl group is an unsubstituted aryl group or an aryl group substituted with an aryl group.

[11] X 1 ~X3 The compound according to any one of [1] to

[10] , wherein

[12] L 1

[0026] The compound according to any one of [1] to

[11] , wherein

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

[12] , wherein

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

[13] , which has at least one deuterium atom.

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

[14] .

[16] A delayed fluorescent material comprising the compound according to any one of [1] to

[14] .

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

[14] and a host material or a dopant material in the same layer.

[18] The organic light-emitting device according to

[17] , wherein the layer contains the dopant material.

[19] The organic light-emitting device according to

[17] or

[18] , wherein the amount of light emitted from the dopant material is greater than the amount of light emitted from the compound.

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

[16] to

[19] , wherein the layer contains the host material.

[21] The organic light-emitting device according to

[20] , wherein the host material is a compound represented by the following general formula (4): [ka] [In the general formula (4), X 11 is O, S, N(R A ) or C(R B )(R C ) stands for A 11 and A 12 R are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring, and these rings may be further condensed with other rings or may be substituted. 111 ~R 114 , R B , R CR each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. 115 R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond to L. A represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond to L. 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 , R B and R C may be bonded to each other to form a cyclic structure. n represents an integer of either 3 or 4. L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group formed by bonding two or more of these.]

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

[16] to

[21] , wherein the amount of light emitted from the compound is the largest among the materials contained in the layer.

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

[16] to

[22] , which emits delayed fluorescence. Effect of the Invention

[0009] The compound and the organic light-emitting device of the present invention exhibit excellent light-emitting properties. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "~" means a range including the numerical values ​​before and after "~" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( 2 In the chemical structural formulas of this specification, hydrogen atoms are represented as H or are omitted. For example, when the atom bonded to the ring-structuring carbon atom of a benzene ring is omitted, H is assumed to be bonded to the ring-structuring carbon atom at the omitted position. In this specification, the term "substituent" means an atom or atomic group other than hydrogen atoms and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0011] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described. [ka]

[0012] In the general formula (1), R 1 R represents a hydrogen atom or a deuterium atom. 2 and R 3 One of the groups is represented by the following general formula (2), R 2 and R 3 and R 4 and R 5 Two of the groups selected from the group consisting of are donor groups, and the remaining one is a substituted or unsubstituted aryl group. 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. In one aspect of the invention, R 1is a hydrogen atom. In one embodiment of the present invention, R 1 is a deuterium atom. In one aspect of the invention, R 2 is a group represented by the following general formula (2), and R 3 and R 4 and R 5 In one embodiment of the present invention, two of R are donor groups and the remaining one is a substituted or unsubstituted aryl group. 2 is a group represented by the following general formula (2), and R 3 and R 5 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 is a group represented by the following general formula (2), and R 4 and R 5 is a donor group, and R 3 is a substituted or unsubstituted aryl group. In one aspect of the invention, R 3 is a group represented by the following general formula (2), and R 2 and R 4 and R 5 In one embodiment of the present invention, two of R are donor groups and the remaining one is a substituted or unsubstituted aryl group. 3 is a group represented by the following general formula (2), and R 2 and R 5 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 3 is a group represented by the following general formula (2), and R 4 and R 5 is a donor group, and R 2 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 3 is a group represented by the following general formula (2), and R 2 and R 4 is a donor group, and R 5 is a substituted or unsubstituted aryl group. The two donor groups present in the general formula (1) may be the same or different.

[0013] R2 ~R 5 , Ar 1 and Ar 2 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 fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one aspect of the invention, the aryl group is unsubstituted. In the following, R 2 ~R 5 , Ar 1 and Ar 2 Specific examples of substituted or unsubstituted aryl groups that can be used are given below. However, the aryl groups that can be used in the present invention should not be construed as being limited to the following specific examples. In the following specific examples, * indicates a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups. [ka] JPEG2024148114000006.jpg206167JPEG2024148114000007.jpg148164

[0014] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar25 are substituted with deuterium atoms are exemplified here as Ar45 to Ar69, in that order. In one aspect of the invention, R 2 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar1 to Ar69. 2 ~R 5 The aryl group of R can be Ar or Ar. 2 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to Ar55. 2 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 2 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar21 to Ar25 and Ar65 to Ar69. 2 ~R 5 The aryl group which can be taken is selected from the group consisting of Ar1, Ar12 to Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar67. In one aspect of the present invention, Ar 1 or Ar 2 The aryl group that can be taken by Ar is selected from the group consisting of Ar1 to Ar69. 1 or Ar 2 The aryl group of Ar can be Ar or Ar. 1 or Ar 2 The aryl group that can be taken by Ar is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to Ar55. 1 or Ar 2 The aryl group that R can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 2 ~R 5The aryl group which can be taken is selected from the group consisting of Ar1, Ar12 to Ar14, Ar36 to Ar38, Ar45, and Ar56 to Ar58.

[0015] R in general formula (1) 2 ~R 5 Two of the R 2 ~R 5 The donor groups which may be used do not include substituted or unsubstituted aryl groups. The "donor group" can be selected from groups with a negative Hammett σp value. The "acceptor group" can be selected from groups with a positive Hammett σp value. The Hammett σp value was proposed by LP Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following formula holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp In the above formula, k0 is the rate constant of a benzene derivative having no substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative having no substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett's σp value" in the present invention and the numerical values ​​of each substituent, the description of the σp value in Hansch, C. et.al., Chem. Rev., 91, 165-195 (1991) can be referred to.

[0016] R 2 ~R 5 The donor group that can be used has a σp of preferably −0.3 or less, more preferably −0.5 or less, and even more preferably −0.7 or less. For example, it may be selected from the range of −0.9 or less, or from the range of −1.1 or less.

[0017] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.The two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0018] R 2 ~R 5 The donor group which can be taken is preferably a group represented by the following general formula (a). [ka]

[0019] In the general formula (a), Z 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N. Z 5 represents C or N, and Ar 5 R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. 14 and R 15 , R 15 and R 16 , R 16 and R 17may be bonded to each other to form a cyclic structure.

[0020] Z 1 ~Z 4 Among these, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one embodiment of the present invention, Z 1 ~Z 4 In one embodiment of the present invention, the number of N is 1. 1 ~Z 4 Of these, the number of N is 0. R 14 ~R 17 each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. 14 ~R 17 When two or more of R represent substituents, those two or more substituents may be the same or different. 14 ~R 17 Of these, 0 to 2 are preferably substituents. For example, one may be a substituent, or none may be a substituent (R 14 ~R 17 may be a hydrogen atom or a deuterium atom). R 14 and R 15 , R 15 and R 16 , R 16 and R 17may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring in which these are condensed. An aromatic ring or a heteroaromatic ring is preferable. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. The heteroaromatic ring means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. Benzofuran, benzothiophene, and indole may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of the substituent groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 In one embodiment of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 are not bonded to each other to form a ring structure.

[0021] In the general formula (a), Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. 5 is C and Ar 5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. 5 is N, and Ar 5 is a substituted or unsubstituted heteroaromatic ring. Ar 5 An example of the aromatic ring that can be used is a benzene ring. The benzene ring may be further condensed with another benzene ring or may be condensed with a heterocycle such as a pyridine ring. 5 The heteroaromatic ring that can be adopted by Z is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, the heteroaromatic ring can be a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring. In one embodiment of the present invention, Z 5 is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. 5 is N, and the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.

[0022] Z in general formula (a) 5When is C, it is preferably a group represented by the following general formula (b). [ka]

[0023] In the general formula (b), Z 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N, Z 6 is CR 18 or N, Z 7 is CR 19 or N, Z 8 is CR 20 or N, Z 9 is CR 21 or N. 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 may be bonded to each other to form a cyclic structure. Z in general formula (b) 1 ~Z 4 , R 14 ~R 17 For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. 6 ~Z 9 , R 18 ~R 21 is Z in general formula (a) 1 ~Z 4 , R 14 ~R 17 These correspond in order to Z in general formula (a). 1 ~Z 4 , R 14 ~R 17Please refer to the explanation in the following. In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 Among these, the number of N is preferably 0 to 2, and more preferably 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 In a preferred embodiment of the present invention, the number of N is 1. 1 ~Z 4 , Z 6 ~Z 9 Among these, the number of N is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0024] R 2 ~R 5 The donor group that R can adopt is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. In addition, the two benzene rings constituting the carbazol-9-yl group may further be condensed with one or more rings. In a preferred embodiment of the present invention, R 2 ~R 5 The donor group which may be taken is a carbazol-9-yl group which may be substituted with a group selected from the substituent group E and which may have one or more condensed rings. When a carbazol-9-yl group which does not have a condensed ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2-7 positions, more preferably at least one of the 3-position or the 6-position, and further preferably the 3-position and the 6-position.

[0025] In one aspect of the invention, R 2 ~R 5The donor group R can take is a carbazol-9-yl group having one or more fused rings, which will be referred to below as a "ring-fused carbazol-9-yl group." 2 ~R 5 The ring-fused carbazol-9-yl group may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from the substituent group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted with an aryl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.

[0026] The total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0027] The ring-fused carbazole-9-yl group is a group bonded by a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may be a ring further fused with these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferable. An example of the aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be further fused with another benzene ring, or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the aromatic heterocycle. In one embodiment of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from the substituent group E (excluding the case where only a deuterium atom is used), and more preferably bonded to an aryl group which may be substituted with an alkyl group or an aryl group. In the present invention, it is preferable to adopt a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms is fused. Among them, a carbazol-9-yl group in which a benzofuro structure is fused, a carbazol-9-yl group in which a benzothieno structure is fused, or a carbazol-9-yl group in which an indolo structure is fused can be preferably adopted. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group in which a benzofuro structure is fused, for example, two or more. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group condensed with a benzothieno structure, for example, has two or more carbazol-9-yl groups.

[0028] As the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group can be used. In addition, as the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used. In addition, as the ring-fused carbazol-9-yl group, a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group can also be used.

[0029] The number of substituents when the ring-fused carbazol-9-yl group is substituted is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or may be, for example, 2. In a preferred embodiment of the present invention, either the 3-position or the 6-position of the ring-fused carbazol-9-yl group is substituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring as viewed from the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring as viewed from the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has a substituent at all of the substitutable para-positions of the benzene ring as viewed from the heteroatom present in the ring-fused carbazol-9-yl group.

[0030] In the following, R in general formula (1) 2 ~R 5 Specific examples of the donor group that can be used are shown below. However, the donor group that can be used in the present invention should not be construed as being limited to the following specific examples. First, specific examples of substituted or unsubstituted carbazol-9-yl groups in which the donor group has a three-ring condensed ring structure are given below. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents the bond position. Methyl groups are not shown, so for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD3. Also, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom. [ka] JPEG2024148114000011.jpg232170JPEG2024148114000012.jpg245170JPEG2024148114000013.jpg108170

[0031] D55 to D85 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D1 to D31 with deuterium atoms.

[0032] Next, specific examples of the donor group having a condensed ring structure of four or more rings are given below. [ka] JPEG2024148114000015.jpg251170JPEG2024148114000016.jpg252170JPEG2024148114000017.jpg242170JPEG2024148114000018.jpg212170JPEG2024148114000019.jpg214170JPEG2024148114000020.jpg215170JPEG2024148114000021.jpg230166JPEG2024148114000022.jpg252170JPEG2024148114000023.jpg223170JPEG2024148114000024.jpg235170JPEG2024148114000025.jpg248170JPEG2024148114000026.jpg217170JPEG2024148114000027.jpg245165JPEG2024148114000028.jpg228170JPEG2024148114000029.jpg197170JPEG2024148114000030.jpg244170JPEG2024148114000031.jpg227170JPEG2024148114000032.jpg211170JPEG2024148114000033.jpg248168JPEG2024148114000034.jpg224170JPEG2024148114000035.jpg205170JPEG2024148114000036.jpg250170JPEG2024148114000037.jpg244170JPEG2024148114000038.jpg214170JPEG2024148114000039.jpg193170JPEG2024148114000040.jpg242170JPEG2024148114000041.jpg218169JPEG2024148114000042.jpg238170JPEG2024148114000043.jpg232170JPEG2024148114000044.jpg210170JPEG2024148114000045.jpg244170JPEG2024148114000046.jpg239170JPEG2024148114000047.jpg234170JPEG2024148114000048.jpg218170JPEG2024148114000049.jpg241170.

[0033] D704 to D1082 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D86 to D456 and D696 to 703 with deuterium atoms. In one aspect of the invention, R 2 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D1082. 2 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D85. 2 ~R 5 The donor group that can be taken by R is selected from the group consisting of D86 to D1082. 2 ~R 5 The donor group that can be taken by R is selected from the group consisting of D86 to D695 and D704 to D1074. 2 ~R 5 The donor group which can be taken is selected from the group consisting of D696 to D703 and D1075 to D1082.

[0034] In one aspect of the invention, at least R 2 is a donor group. In one embodiment of the present invention, at least R 3 is a donor group. In one embodiment of the present invention, at least R 4 is a donor group. In one embodiment of the present invention, at least R 5 is a donor group. In one embodiment of the present invention, R 3 and R 5 is a donor group. In one embodiment of the present invention, R 4 and R 5 is a donor group. In one embodiment of the present invention, R 2 and R 5 is a donor group. In one embodiment of the present invention, R 2 and R 4 is a donor group. In one embodiment of the present invention, R 2 and R 5is a donor group.

[0035] Ar in general formula (1) 1 and Ar 2 The heteroaryl 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 fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a pyridine ring, a pyrimidine ring, and a pyrrole ring, and these rings may be further fused with another ring. Specific examples of the heteroaryl group include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a carbazol-1-yl group, a carbazol-2-yl group, a carbazol-3-yl group, and a carbazol-4-yl group. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within the range of 5 to 16 or 5 to 12. In one aspect of the present invention, Ar 1 and Ar 2 is a substituted or unsubstituted aryl group.

[0036] In the general formula (1), R 2 or R 3 is a group represented by the following general formula (2). 4 , R 5 can also be a group represented by the following general formula (2). [ka]

[0037] In the general formula (2), X 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of the groups is N. R represents a hydrogen atom, a deuterium atom, or a substituent. Ar 3 and Ar 4 Each of L independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.1 represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. * represents the bonding position.

[0038] L in general formula (2) 1 represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L 1 is a single bond. In one embodiment of the present invention, L 1 is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L 1 is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group is as defined above for R 2 ~R 5 Refer to the description and preferred range of the aryl group in the description section of "1. Heteroarylene group" can be exemplified by a linking group in which at least one of the ring skeleton carbon atoms constituting an arylene group is substituted with a nitrogen atom. In the following, L 1 However, the following are specific examples of L that can be used in the present invention. 1 is not to be construed as being limited by these specific examples. In the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are substituted with a methyl group. * indicates a bond position. L1 is a single bond.

[0039] [ka]

[0040] All hydrogen atoms in L2 to L13 are replaced with deuterium atoms, and L14 to L25 are disclosed as such. 1 is selected from the group consisting of L1 to L25. In one embodiment of the present invention, L 1 is selected from the group consisting of L1 to L7 and L14 to L19. 1is selected from the group consisting of L1, L8 to L13, and L20 to L25. 1 is selected from the group consisting of L2 to L25.

[0041] X in general formula (2) 1 ~X 3 Each independently represents N or C(R). 1 ~X 3 At least one of is N. R represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. In a preferred embodiment of the present invention, X 1 ~X 3 is N. In one embodiment of the present invention, X 1 and X 3 is N and X 2 is C(R). In one embodiment of the present invention, X 1 and X 2 is N and X 3 is C(R). In one embodiment of the present invention, X 1 is N and X 2 and X 3 is C(R). In one embodiment of the present invention, X 2 is N and X 1 and X 3 is C(R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, R is a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group.

[0042] Ar in general formula (2) 3 and Ar 4 Specific examples and preferred ranges of Ar 1 and Ar 2 In one embodiment of the present invention, Ar 1 and Ar 3In a preferred embodiment of the present invention, Ar 1 and Ar 3 are identical, and Ar 2 and Ar 4 In one aspect of the present invention, Ar 1 ~Ar 4 are identical.

[0043] In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 In one embodiment of the present invention, X 1 ~X 3 is N and L 1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (for example, L2, for example, L6). In one aspect of the invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 3 and Ar 4 In one aspect of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 3 and Ar 4 Each of X is independently a substituted or unsubstituted aryl group. 1 ~X 3 is N and L 1 is a single bond, and Ar 3 and Ar 4 are each independently a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, and more preferably a substituted or unsubstituted carbazol-9-yl group. 1 ~X 3 is N and L 1 is a single bond, and Ar 3is a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, more preferably a substituted or unsubstituted carbazol-9-yl group; Ar 4 is a substituted or unsubstituted aryl group.

[0044] In a preferred embodiment of the present invention, R 2 In a preferred embodiment of the present invention, only R 3 In one embodiment of the present invention, R 3 , R 4 , R 5 One of the R 2 In one embodiment of the present invention, R 2 , R 4 , R 5 One of them and R 3 are each independently a group represented by general formula (2).

[0045] In a preferred embodiment of the present invention, R 2 ~R 5 At least one of the donor groups has a condensed ring structure of four or more rings. The "donor group having a condensed ring structure of four or more rings" here means a donor group that has a condensed ring structure of four or more rings and is bonded to one of the ring skeleton constituent atoms of the condensed ring structure. The one atom is preferably a carbon atom or a nitrogen atom, and more preferably a nitrogen atom. The donor group here means a group with a negative Hammett σp value. The donor group having a fused ring structure of 4 or more rings preferably has a fused ring structure of 5 or more rings, and more preferably has a fused ring structure of 5 to 7 rings. For example, there can be mentioned those having a fused ring structure of 5 rings and those having a fused ring structure of 7 rings.

[0046] The donor group having a fused ring structure of 4 or more rings is preferably a ring-fused carbazol-9-yl group. Specific examples include D86 to D1141. In particular, a group having a structure represented by the following general formula (3) is preferred. [ka]

[0047] In the general formula (3), X is O, S or NR 14 Represents R 11 ~R 13 Each independently represents a deuterium atom or a substituent. 14 R represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group. 11 Fellow, R 12 Fellow, R 13 may be bonded to each other to form a cyclic structure. n11 and n13 each independently represent an integer of 0 to 4; n12 represents an integer of 0 to 2.

[0048] In the general formula (3), X is O, S or NR 14 Represents R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group. Here, the aryl group as a substituent of the aryl group and the alkyl group can be selected, for example, from aryl groups having 6 to 22 carbon atoms, and the alkyl group as a substituent of the alkyl group and the aryl group can be selected, for example, from alkyl groups having 1 to 20 carbon atoms. In a preferred embodiment of the present invention, X is O. In a preferred embodiment of the present invention, X is NR 14 For example, NR 14 R 14is an aryl group (e.g., having 6 to 22 carbon atoms). The aryl group may be unsubstituted or may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms). X may be an oxygen atom or a sulfur atom. In general formula (3), the two bonds of one of the benzene rings of the carbazole ring are bonded to adjacent positions of the benzene ring to form a fused ring structure between the carbazole ring and a hetero fused ring containing X. For example, when X is O, a benzofurocarbazole ring is formed as the fused ring structure, and when X is S, a benzothienocarbazole ring is formed as the fused ring structure, and when X is NR 14 In the case where the bond positions of the two bonds are the 1st and 2nd positions, the 2nd and 3rd positions, or the 3rd and 4th positions of the carbazole ring, an indolocarbazole ring is formed as a condensed ring structure. The positions to which the two bonds are bonded may be the 1st and 2nd positions, the 2nd and 3rd positions, or the 3rd and 4th positions. When the bond positions of the two bonds are the 1st and 2nd positions, the bond position of X may be the 1st or 2nd position, when the bond positions of the two bonds are the 2nd and 3rd positions, the bond position of X may be the 2nd or 3rd position, when the bond positions of the two bonds are the 3rd and 4th positions, the bond position of X may be the 3rd or 4th position. In formula (3), * represents a bonding position. In the general formula (3), R 11 ~R 13 Each independently represents a deuterium atom or a substituent. 11 Fellow, R 12 Fellow, R 13 may be bonded to each other to form a ring structure, 11 R 12 ~R 14 does not bond with any of R to form a ring structure, 12 R 13 , R 14 does not bond with any of R to form a ring structure, 13 R 14and do not bond to each other to form a cyclic structure. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2. When n11 is 2 or more, two or more R 11 may be the same or different. When n13 is 2 or more, two or more R 13 may be the same or different. When n12 is 2, two R 12 may be the same or different. n11 and n13 may be any number of 0, 1, 2, 3, or 4, and n12 may be any number of 0, 1, or 2. When n11 is 1, R 11 may be a deuterium atom or a substituent. When n11 is 2 or more, two or more R 11 may all be deuterium atoms or all be substituents, or some of them may be deuterium atoms and the rest may be substituents. When n13 is 1, R 13 may be a deuterium atom or a substituent. When n13 is 2 or more, 2 or more R 13 may all be deuterium atoms or all be substituents, or some of them may be deuterium atoms and the rest may be substituents. When n12 is 1, R 12 may be a deuterium atom or a substituent. When n12 is 2, two R 12 may both be deuterium atoms or both be substituents, or one of the two may be a deuterium atom and the other a substituent.

[0049] In one aspect of the invention, R 2 ~R 5Among these, two donor groups are each a donor group having a condensed ring structure of four or more rings, and more preferably a donor group represented by general formula (3). The two donor groups may be the same or different, but are preferably the same. In one embodiment of the present invention, at least R 2 In one embodiment of the present invention, at least R 3 In one embodiment of the present invention, at least R 4 In one embodiment of the present invention, at least R 5 In one embodiment of the present invention, R 3 and R 5 In one embodiment of the present invention, R 4 and R 5 In one embodiment of the present invention, R 2 and R 5 In one embodiment of the present invention, R 2 and R 4 In one embodiment of the present invention, R 3 and R 4 is a donor group having a condensed ring structure of four or more rings.

[0050] In a preferred embodiment of the present invention, Ar 1 ~Ar 4 At least one of the heteroaryl groups is a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing six-membered ring groups). The substituted or unsubstituted heteroaryl group (excluding nitrogen-containing six-membered ring groups) is Ar 1 ~Ar 4There may be only one, two, three or all of the above. When there are two or more, they may be the same or different, but it is preferable that they are the same. The substituted or unsubstituted heteroaryl group (excluding the nitrogen-containing 6-membered ring group) is preferably a heteroaryl group bonded at a nitrogen atom, which is one of the ring skeleton constituent atoms, and is preferably a heteroaryl group having a 5-membered ring bonded at a nitrogen atom (a group bonded at the nitrogen atom of a pyrrole ring, which may be substituted and is preferably a condensed ring), and is more preferably a substituted or unsubstituted carbazol-9-yl group. In a preferred embodiment of the present invention, the carbazol-9-yl group may be substituted with an alkyl group or an aryl group which may be substituted with a group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or may be substituted with a deuterium atom. For an explanation and details of the carbazol-9-yl group, see R 2 ~R 5 The description of the carbazol-9-yl group which can be taken, the description of the ring-fused carbazol-9-yl group, and specific examples D1 to D1141 can be referred to.

[0051] Ar in general formula (1) 1 ~Ar 4 is a phenyl group optionally substituted with an alkyl group, R 2 ~R 5 At least one of R is preferably a donor group having a condensed ring structure of four or more rings. 2 ~R 5 It is more preferable that two of the groups be donor groups each having a condensed ring structure with four or more rings. In a preferred embodiment of the present invention, Ar 1 ~Ar 4 At least one of R is a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), or 2 ~R 5 At least one of the groups is a donor group having a condensed ring structure of four or more rings.

[0052] The compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.

[0053] In the present specification, the term "substituent group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 ring skeleton atoms), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. In this specification, "substituent group B" means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). In this specification, the term "substituent group C" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms). As used herein, the term "substituent group E" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.

[0054] Specific examples of the compound represented by general formula (1) are shown in the following Tables 1 to 4. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R 3 ~R 5The structure of each compound is shown individually by specifying each compound. 2 is a group represented by general formula (2), Ar 1 and Ar 3 is a perdeuterated carbazol-9-yl group (D55), and Ar 2 and Ar 4 is a perdeuterated phenyl group (Ar45), and X 1 ~X 3 is a nitrogen atom (N), and L 1 is a single bond (L1), and R 1 is a hydrogen atom, and R 3 ~R 5 The structures in which is a group specified in Table 1 are shown individually as the structures of compounds 1 to 170. [ka] [Table 1]

[0055] In Table 2, multiple compounds are listed in each row. 3 ~R 5 The structures of compounds 1 to 149316 are shown by displaying them together. For example, in the column of compounds 1 to 170 in Table 2, R 4 is fixed to Ar1 (phenyl group), and R 3 and R 5 In other words, the row of compounds 1 to 170 in Table 2 collectively shows compounds 1 to 170 specified in Table 1. In addition, in the row of compounds 171 to 1082 in Table 2, R 4 is fixed at Ar1, and R 3 and R 5 In the same manner, in the column of compounds 1083 to 2164 in Table 2, R 4 is fixed at Ar2, and R 3 and R 5The compounds D1 to D1082 that are the same are designated as compounds 1083 to 2164, respectively. Compounds 2165 to 149316 in Table 2 are also identified in the same manner. [Table 2] JPEG2024148114000056.jpg255142JPEG2024148114000057.jpg89170

[0056] Next, specific examples of compounds having a structure represented by the following general formula (1b) are shown in Table 3. In Table 3, the structure of each compound is shown in the same manner as in Table 2. [ka] [Table 3] JPEG2024148114000060.jpg253170JPEG2024148114000061.jpg255137JPEG2024148114000062.jpg125170

[0057] In Tables 1 to 3, Ar in general formula (1) 1 and Ar 3 is a perdeuterated carbazol-9-yl group (D55), and Ar 2 and Ar 4 The structures of compounds 1 to 373290 were identified as those in which Ar is a perdeuterated phenyl group (Ar45). Table 4 shows the structure of each of compounds 1 to 373290. 1 ~Ar 4 The compounds in which the Ar was changed as shown in Table 4 are displayed in order in the form of a table. In Table 4, compounds 1 to 373290 are also displayed in the first row in order to make the correspondence easier to understand. In the second row of Table 4, the Ar of compounds 1 to 362104 is displayed in the second row. 1 and Ar 3 The compounds in which both are D1 are designated as compounds 1(1) to 373290(1), respectively. For example, compound 1(1) is 1 and Ar 3Compound 2(1) is a compound having a structure in which Ar of Compound 2 is substituted with D1. 1 and Ar 3 Compound 373290(1) shows a compound having a structure in which Ar is substituted with D1. 1 and Ar 3 The third row of Table 4 shows compounds having a structure in which Ar is substituted with D1. 1 and Ar 3 The compounds in which both are D7 are named compounds 1(2) to 373290(2), respectively. 1 and Ar 3 , Ar 2 and Ar 4 The compounds are specified in Table 4 in order. 1 ~X 3 are all nitrogen atoms (N), and L 1 is a single bond (L1), and R 1 is a hydrogen atom. Ar 1 and Ar 3 are identical, and Ar 2 and Ar 4 are identical. [Table 4] JPEG2024148114000064.jpg255159

[0058] All compounds identified by numbers in Tables 1 to 4 are considered to be individually disclosed. In addition, when rotamers exist among the specific examples of the compounds, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification. In one aspect of the invention, the compound is selected from the group of compounds identified in Table 4.

[0059] An example of a preferred compound group represented by the general formula (1) is given below. [ka]

[0060] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by deposition, for example, the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by the general formula (1) has the advantage that it is easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method to, and is easy to purify to increase the purity.

[0061] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and the polymer may be polymerized to obtain a polymer, which may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, which may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled together to obtain a dimer or trimer, which may be used as a light-emitting material.

[0062] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas. [ka]

[0063] In the above general formula, Q represents a group containing a structure represented by general formula (1), L 1 and L 2 represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. The linking group is -X 11 -L 11 In this case, it is preferable that X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. 11 represents a linking group, which is preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represents a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and further preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L 1 and L 2 The linking group represented by the following formula can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0064] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0065] A polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group. [ka]

[0066] The polymer containing the structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type or of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples of repeating units include those derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene.

[0067] For uses of the compound represented by general formula (1), reference can be made to

[0058] to

[0059] ,

[0061] , and

[0063] of WO2022 / 168956A1, which is incorporated herein by reference as part of this specification.

[0068] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by the general formula (1) include novel compounds. The compound represented by the general formula (1) can be synthesized by combining known reactions. 2 ~R 5 Two of the groups are donor groups, and for example, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is a donor group can be synthesized by reacting a precursor in which the donor group is a fluorine atom with a substituted or unsubstituted carbazole. For details of the reaction conditions, refer to the synthesis examples described later.

[0069] [Organic light-emitting element] The organic light-emitting device of the present invention contains a compound represented by general formula (1) and a host material or a dopant material in the same layer. The same layer is preferably an emission layer. In one embodiment of the present invention, the compound represented by general formula (1) and a host material are contained in the same layer. The host material is used at a higher concentration than the compound represented by general formula (1), and preferably has a higher minimum excited singlet energy than the compound represented by general formula (1). In one embodiment of the present invention, the compound represented by general formula (1) and a dopant material are contained in the same layer. The dopant material is used at a lower concentration than the compound represented by general formula (1), and preferably has a lower minimum excited singlet energy than the compound represented by general formula (1). In one embodiment, the compound represented by formula (1) functions as a light-emitting material in an organic light-emitting device. In one embodiment, the compound represented by formula (1) functions as a light-emitting material that emits delayed fluorescence in an organic light-emitting device. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near infrared region when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., from about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) are capable of emitting light in the blue region of the visible spectrum (e.g., from about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet region of the spectrum (eg, 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0070] When forming layers of an organic light-emitting device, a film forming technique can be used. In an embodiment, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In an embodiment, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In an embodiment, the film containing the compound of the present invention can be formed by a dry process. In an embodiment, the dry process can be a vacuum deposition method, but is not limited thereto. When the vacuum deposition method is adopted, the compounds constituting the film may be co-deposited from individual deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed. When a single deposition source is used, a mixed powder in which powders of the compounds are mixed may be used, or a compression molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used. In an embodiment, a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed by performing co-deposition under conditions in which the deposition rates (weight reduction rates) of the multiple compounds contained in a single deposition source are the same or almost the same. If the multiple compounds are mixed in the same composition ratio as the composition ratio of the film to be formed and used as the deposition source, a film having a desired composition ratio can be easily formed. In an embodiment, a temperature at which each compound to be co-deposited has the same weight reduction rate can be specified, and the temperature can be used as the temperature during co-deposition.

[0071] In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level and is included between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least a light-emitting layer. In some embodiments, the organic layer includes only a light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with a hole injection function, and the electron transport layer may be an electron injection transport layer with an electron injection function.

[0072] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, the light-emitting layer includes a light-emitting material that is a dopant material and a host material. In some embodiments, the light-emitting material is a compound represented by general formula (1). In some embodiments, in order to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet excitons and triplet excitons generated in the light-emitting material are trapped in the light-emitting material. In some embodiments, a host material is used in the light-emitting layer in addition to the light-emitting material. 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, at least one of which is higher than those of the light-emitting material of the present invention. In some embodiments, the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are trapped in the molecules of the light-emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently trapped to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently trapped, although a high light emission efficiency is still obtained, i.e., a host material that can achieve a high light emission efficiency can be used in the present invention without any particular limitation. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0073] (Dopant materials) When the compound represented by the general formula (1) is used as a host material or an assist dopant, various compounds can be adopted as a light-emitting material (preferably a fluorescent material) which is a dopant material. As such light-emitting materials, anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), and the like can be used. These exemplary skeletons may or may not have a substituent. These exemplary skeletons may be combined with each other. Examples of dopant materials (light-emitting materials) that can be used in combination with the compound represented by formula (1) are given below.

[0074] [ka] JPEG2024148114000070.jpg223165JPEG2024148114000071.jpg255168

[0075] In addition to the above, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be used as light-emitting materials used together with the assist dopant having a structure represented by general formula (1).

[0076] In one embodiment, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between the lowest excited singlet energy level and the lowest excited triplet energy level of 77K. STis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecule in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In an embodiment, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecule, and 0.1 to 30 wt % of the second TADF molecule. In one embodiment, the composition in the light-emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule. In one embodiment, the light emission quantum yield φPL1(A) by light excitation of the co-deposited film of the first TADF molecule and the host material (the concentration of the first TADF molecule in this co-deposited film is A% by weight) and the light emission quantum yield φPL2(A) by light excitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-deposited film is A% by weight) satisfy the relational expression φPL1(A)>φPL2(A). In one embodiment, the light emission quantum yield φPL2(B) by light excitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-deposited film is B% by weight) and the light emission quantum yield φPL2(100) by light excitation of the single film of the second TADF molecule satisfy the relational expression φPL2(B)>φPL2(100). In some embodiments, the light-emitting layer can contain three structurally different TADF molecules. The compound of the present invention can be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be made of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescent material.Preferred delayed fluorescent materials include those described in paragraphs 0008-0048 and 0095-0133 of WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. JP 2013-256490 A, paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040; WO 2013 / 133359 A, paragraphs 0007 to 0032 and 0079 to 0084; WO 2013 / 161437 A, paragraph 0 JP 2014-9352 A, paragraphs 0007-0041 and 0060-0069, JP 2014-9224 A, paragraphs 0008-0048 and 0067-0076, JP 2017-119663 A, paragraphs 0013-0025, JP 2017-119664 A, paragraphs 0013-0026, JP 2017-119664 A, The compounds included in the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly the example compounds, which are capable of emitting delayed fluorescence, are included.In addition, the following publications are included herein: JP2013-253121A, WO2013 / 133359A, WO2014 / 034535A, WO2014 / 115743A, WO2014 / 122895A, WO2014 / 126200A, WO2014 / 136758A, WO2014 / 133121A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714A, WO2015 / 129715A, WO2015 / 13350 The luminescent materials described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, which are capable of emitting delayed fluorescence, can be preferably used. Note that the above publications described in this paragraph are hereby incorporated by reference as part of this specification.

[0077] (Host material) When the compound represented by formula (1) is used together with a host material, the amount of the compound represented by formula (1) is 0.1% by weight or more. In an embodiment, when a host material is used, the amount of the compound represented by formula (1) as the light-emitting material contained in the light-emitting layer is 1% by weight or more. In an embodiment, when a host material is used, the amount of the compound represented by formula (1) as the light-emitting material contained in the light-emitting layer is 50% by weight or less. In an embodiment, when a host material is used, the amount of the compound represented by formula (1) as the light-emitting material contained in the light-emitting layer is 20% by weight or less. In an embodiment, when a host material is used, the amount of the compound represented by formula (1) as the light-emitting material contained in the light-emitting layer is 10% by weight or less. In some embodiments, the host material of the light-emitting layer is an organic compound that has hole transport and electron transport functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0078] In some embodiments, the host material is selected from the group consisting of: [ka] JPEG2024148114000073.jpg255168

[0079] In a preferred embodiment of the present invention, the host material used together with the compound represented by general formula (1) is a compound having a structure represented by the following general formula (4). [ka]

[0080] In the general formula (4), X 11 is O, S, N(R A ) or C(R B )(R C In one aspect of the present invention, X 11 is O, S or N(R AIn one aspect of the present invention, X 11 is O or S. In one embodiment of the present invention, X 11 is N(R A In one aspect of the present invention, X 11 is O. In one embodiment of the present invention, X 11 is S. X 11 is O, S or C(R B )(R C ), then L is (R 115 )n is bonded to the benzene ring to which X 11 N(R A ), then L is (R 115 )n is attached to the benzene ring or X 11 The bond extending from L to the right is represented by (R 115 )n is attached to the benzene ring to which it is attached, or X 11 When N, X 11 (i.e. N).

[0081] In the general formula (4), A 11 and A 12 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, and these rings may be further condensed with other rings or may be substituted. 11 is a benzene ring. In a preferred embodiment of the present invention, A 12 is a benzene ring. In a further preferred embodiment of the present invention, A 11 and A 12 are both benzene rings. 11 and A 12 At least one of A is a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring. 11 and A 12 At least one of A is a furan ring. 11 and A 12 At least one of A is a thiol ring. 11 and A 12At least one of A is a pyrrole ring. 11 and A 12 At least one of these is a cyclopentadiene ring. The benzene ring, furan ring, thiol ring, pyrrole ring and cyclopentadiene ring may further be condensed with another ring. The condensed ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring and an aliphatic heterocycle, and may be a ring in which two or more of these are condensed. An aromatic hydrocarbon ring, an aromatic heterocycle, or a ring in which two or more of these are condensed is preferable. An example of the aromatic hydrocarbon ring is a benzene ring. The aromatic heterocycle means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocycle. The aliphatic hydrocarbon ring is preferably a hydrocarbon ring that does not exhibit aromaticity, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. For example, a cyclopentadiene ring can be adopted. The aliphatic heterocycle means a ring that contains a heteroatom as a ring skeleton-constituting atom and does not exhibit aromaticity, and is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, A 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed. 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed. 11 is a benzene ring, and the furan ring of benzofuran or the thiophene ring of benzothiophene is condensed to the benzene ring. 11 is fused to the furan ring of the benzofuran. 11is fused to the thiophene ring of the benzothiophene. 12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed. 12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed. 12 is a benzene ring, and the furan ring of benzofuran or the thiophene ring of benzothiophene is condensed to the benzene ring. 12 is fused to the furan ring of the benzofuran. 12 is condensed with the thiophene ring of benzothiophene. A 11 Or A 12 The hydrogen atoms of the rings constituting the ring may be substituted with deuterium atoms or substituents. The substituents can be selected from any of the substituent groups A to E, for example, from the substituent group E. In one embodiment of the present invention, A 11 Or A 12 The ring constituting A may be substituted with one atom or group, or a combination of two or more atoms selected from the group consisting of a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, and a cyano group. 11 Or A 12 The ring constituting A may be substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. 11 Or A 12 At least one of the rings constituting A is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. 11 Or A 12 When a pyrrole ring is included as a ring constituting the ring, it is preferable that a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group is bonded to a nitrogen atom constituting the ring skeleton of the pyrrole ring (the same applies to the nitrogen atom of the indole ring described below).11 Or A 12 When two or more hydrogen atoms of the ring constituting the formula (I) are replaced, they may be replaced by the same atom or group or by different atoms or groups.

[0082] In the general formula (4), R 111 ~R 114 , R B , R C R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. 115 R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond to L (i.e., a single bond to L). A represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L (i.e., a single bond to L). For the aryl group, the heteroaryl group, and the alkyl group, the above explanations of "aryl group", "heteroaryl group", and "alkyl group" can be referred to. The number of carbon atoms of the aryl group is preferably 6 to 14, and examples thereof include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. The heteroaryl group is preferably composed of a 5-membered or 6-membered ring, and examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a dibenzofuryl group, and a dibenzothienyl group. The number of carbon atoms of the alkyl group is preferably 1 to 6, and examples thereof include a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group. These aryl groups, heteroaryl groups, and alkyl groups may be substituted, and when substituted, they are preferably substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, and more preferably substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group. 112is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. 111 ~R 114 are each independently a hydrogen atom or a deuterium atom. R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 , R B and R C may be bonded to each other to form a cyclic structure. The cyclic structure referred to here is as defined above in A 11 and A 12 In one embodiment of the present invention, R 111 and R 112 , R 112 and R 113 , R 113 and R 114 are bonded together to form a benzofuran ring (fused with a furan ring), a benzothiophene ring (fused with a thiophene ring), or an indole ring (fused with a pyrrole ring).

[0083] In one embodiment of the present invention, the group bonded to L from the left in general formula (4) is a substituted or unsubstituted carbazol-9-yl group. For example, it is a carbazol-9-yl group in which at least one (preferably both) of the 3-position and the 6-position is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination of these groups. It may also be an unsubstituted carbazol-9-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (4) is a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (4) is a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (4) is a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the right in general formula (4) may also be any of the groups exemplified above as the group bonded to L from the left, provided that the group is not an unsubstituted carbazol-9-yl group.

[0084] In the following, specific examples of groups that can be used as the group bonded to the left of L in general formula (4) are given. However, the groups that can be used in the present invention are not limited to these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, Z2 and Z3 are substituted with methyl groups. * indicates the bonding position to L. [ka] JPEG2024148114000076.jpg226170JPEG2024148114000077.jpg211170JPEG2024148114000078.jpg235170JPEG2024148114000079.jpg215170 JPEG2024148114000080.jpg221170JPEG2024148114000081.jpg212170JPEG2024148114000082.jpg237170JPEG2024148114000083.jpg131170

[0085] In addition to the above specific examples, groups in which all hydrogen atoms of the alkyl groups Z2, Z3, Z5, Z7 to Z12, Z87 to Z104, and Z179 to Z196 are replaced with deuterium atoms are exemplified here as Z2(m), Z3(m), Z5(m), Z7(m) to Z12(m), Z87(m) to Z104(m), and Z179(m) to Z196(m), respectively. Also, groups in which the phenyl groups (CH) of Z4 to Z6, Z19 to Z86, and Z111 to Z178 are replaced with deuterated C6D5 are exemplified here as Z4(p) to Z6(p), Z19(p) to Z86(p), and Z111(p) to Z178(p), respectively. Furthermore, groups in which all hydrogen atoms in Z1 to Z196 are deuterated are exemplified here as Z1(D) to Z196(D), respectively.

[0086] In general formula (4), specific examples of the group that can be bonded to the right of L include the above Z2 to Z196 and their deuterium atom-substituted derivatives, as well as the specific examples shown below. However, the groups that can be employed in the present invention are not limited to these specific examples. Note that in the following specific examples, methyl groups are omitted. * indicates the bonding position to L. [ka] JPEG2024148114000085.jpg230170JPEG2024148114000086.jpg246170JPEG2024148114000087.jpg243170JPEG2024148114000088.jpg102170

[0087] In addition to the above specific examples, groups in which the methyl groups (CH3) of X31 to X33 and X64 to X79 are replaced with deuterated CD3 are exemplified here as X31(m) to X33(m) and X64(m) to X79(m), respectively. Groups in which the phenyl groups (CH5) of X5 to X21, X38 to X54 and X68 to X70 are replaced with deuterated C6D5 are exemplified here as X5(p) to X21(p), X38(p) to X54(p) and X68(p) to X70(p), respectively. Furthermore, groups in which all hydrogen atoms of X1 to X79 are deuterated are exemplified here as X1(D) to X79(D), respectively.

[0088] In the general formula (4), n represents an integer of 3 or 4. 11 is O, S or C(R B )(R C ), then L is (R 115 )n is bonded to the benzene ring to which it is attached, so n is 3. X 11 N(R A ) and L is (R 115 ) n is bonded to the benzene ring to which it is attached, n is 3, and X 11 N(R A ) where L is X 11When R is bonded to N, n is 4. 115 may be the same or different from each other.

[0089] L in the general formula (4) represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group to which two or more of these are bonded. For the aryl structure of the arylene group and the heteroaryl structure of the heteroarylene group, the above explanations of "aryl group" and "heteroaryl group" can be referred to. The arylene group and the heteroarylene group may be substituted, and if substituted, they are preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, or a group combining two or more of these, and more preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group, or a group combining two or more of these. If substituted, they are preferably methyl, ethyl, isopropyl, tert-butyl, phenyl, or deuterated versions thereof. In one embodiment of the present invention, L is an unsubstituted arylene group. Specific examples of L are given below. However, L that can be adopted in the present invention is not limited to these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates a bond position. L1 is a single bond.

[0090] [ka]

[0091] In one embodiment of the present invention, the group bonded from the left of L in general formula (4) is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 1). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z12 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 2). In one embodiment of the present invention, the group bonded from the left of L is selected from Z13 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 3). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X66 and their deuterated forms (embodiment 4). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X33 and their deuterated forms (Aspect 5). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X21, X31 to X33 and their deuterated forms (Aspect 6). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X22 to X30 and their deuterated forms (Aspect 7). In one embodiment of the invention, in embodiment 1, L is L1. In one embodiment of the invention, in embodiment 2, L is L1. In one embodiment of the invention, in embodiment 3, L is L1. In one embodiment of the invention, in embodiment 4, L is L1. In one embodiment of the invention, in embodiment 5, L is L1. In one embodiment of the invention, in embodiment 6, L is L1. In one embodiment of the invention, in embodiment 7, L is L1. In one embodiment of the invention, in embodiment 1, L is L6. In one embodiment of the invention, in embodiment 2, L is L6. In one embodiment of the invention, in embodiment 3, L is L6. In one embodiment of the invention, in embodiment 4, L is L6. In one embodiment of the invention, in embodiment 5, L is L6. In one embodiment of the invention, in embodiment 6, L is L6. In one embodiment of the invention, in embodiment 7, L is L6. In one embodiment of the invention, in embodiment 1, L is L14. In one embodiment of the invention, in embodiment 2, L is L14. In one embodiment of the invention, in embodiment 3, L is L14. In one embodiment of the invention, in embodiment 4, L is L14. In one embodiment of the invention, in embodiment 5, L is L14. In one embodiment of the invention, in embodiment 6, L is L14. In one embodiment of the invention, in embodiment 7, L is L14. In one embodiment of the invention, in embodiment 1, L is L16. In one embodiment of the invention, in embodiment 2, L is L16. In one embodiment of the invention, in embodiment 3, L is L16. In one embodiment of the invention, in embodiment 4, L is L16. In one embodiment of the invention, in embodiment 5, L is L16. In one embodiment of the invention, in embodiment 6, L is L16. In one embodiment of the invention, in embodiment 7, L is L16.

[0092] Specific examples of the compound represented by general formula (4) are shown below. However, the compound represented by general formula (4) that can be used in the present invention is not limited to the following specific examples.

[0093] [ka]

[0094] In addition to the above specific examples, compounds in which all hydrogen atoms in the substituted or unsubstituted carbazol-9-yl groups in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(d) to H13(d), respectively. Compounds in which all hydrogen atoms in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(D) to H13(D), respectively.

[0095] The molecular weight of the compound represented by general formula (4), for example, when it is intended to form an organic layer containing the compound represented by general formula (4) into a film by a vapor deposition method and use it, is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 800 or less, and may be, for example, 600 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (4).

[0096] The compound represented by the general formula (4) is preferably one having a smaller dipole moment because the orientation of the film formed therefrom is higher. The dipole moment is preferably smaller than 2.3, more preferably smaller than 2.0, even more preferably smaller than 1.7, and even more preferably smaller than 1.4.

[0097] As the compound represented by the general formula (4), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected. For example, as the compound represented by the general formula (4), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as the compound represented by the general formula (4), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms can be selected. For example, as the compound represented by the general formula (4), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms can be selected.

[0098] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0099] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0100] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering. In some embodiments, the film is patterned by a photolithographic method. In some embodiments, if the pattern does not need to be highly accurate (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering on the electrode material. In some embodiments, when a coating material, such as an organic conductive compound, can be applied, a wet film formation method, such as a printing method or a coating method, is used. In some embodiments, the anode has a transmittance of more than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0101] cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, one of the anode and cathode of the organic electroluminescent device is transparent or semi-transparent to transmit emitted light. In some embodiments, a transparent or semi-transparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.

[0102] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are given below.

[0103] [ka]

[0104] Next, preferred examples of compounds that can be used as the electron injection material will be given. [ka]

[0105] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the term "electron barrier layer" or "exciton barrier layer" includes layers that have both the functions of an electron barrier layer and of an exciton barrier layer.

[0106] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.

[0107] [ka]

[0108] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.

[0109] [ka] JPEG2024148114000095.jpg46170

[0110] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0111] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.

[0112] [ka]

[0113] Electron transport layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0114] [ka]

[0115] In addition, examples of compounds that can be added to each organic layer are given below, which may be used as stabilizing materials, for example.

[0116] [ka]

[0117] Although the preferred materials that can be used in the organic electroluminescence element are specifically exemplified, the materials that can be used in the present invention are not limited to the following exemplified compounds. In addition, even if a compound is exemplified as a material having a specific function, it can be diverted to a material having other functions.

[0118] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions may be useful for facilitating charge or energy transfer within the device and / or as hole transport materials, such as organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0119] Bulb or Lamp: In some embodiments, the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device comprises: a circuit board having a first side having a mounting surface and an opposing second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light comprises a plurality of OLEDs mounted on a circuit board such that light is emitted in a plurality of directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0120] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful in two-sided etching to provide pixels of unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of an OLED display. The corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction. This allows for the fine patterning of pixels required for high resolution displays while optimizing chemical vapor deposition onto the TFT backplane. The internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold rolled into long thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable and low-cost method for forming open areas in the deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0121] How the device is manufactured: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0122] In another aspect of the invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in the form of a cell panel; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be cut softly into cell panels. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed at the same time as the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to the display unit or the encapsulation layer.

[0123] Each of the organic film and the planarization film may include one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide prior to forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate prior to cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer for covering the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0124] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source / drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is disposed at an interval with each of the plurality of display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.

[0125] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, a barrier layer is formed on a 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, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0126] In some embodiments, the method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on the TFT layer to cover the TFT layer. At the same time as the planarization film, which is made of, for example, polyimide or acrylic, is formed, the groove of the interface is covered with an organic film, which is made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the groove at the interface by having the organic film absorb the impact that occurs. That is, if all the barrier layers are completely exposed without the organic film, when each cell panel is cut along the groove at the interface, the impact that occurs will be transmitted to the barrier layer, thereby increasing the risk of cracks. However, in one embodiment, the groove of the interface between the barrier layers is covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel can be cut softly and prevent cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface are spaced apart from each other. For example, when the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining part of the organic film, so the organic film and the planarization film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0127] In some embodiments, the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, the barrier layer is prevented from cracking during cutting. In some embodiments, the methods reduce product defect rates and stabilize product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. EXAMPLES

[0128] The characteristics of the present invention will be described in more detail below with reference to synthesis examples and examples. The materials, processing contents, processing procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The evaluation of the emission characteristics was performed using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics C4334).

[0129] (Synthesis Examples 1 to 3) Synthesis of Compounds P1, P2, and P3 Compound j [ka]

[0130] Phenyl-d5-boronic acid (6.2 g, 48.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.4 g, 2.0 mmol), and potassium carbonate (29.0 g, 210 mmol) were added to a mixed solution of 1,5-dibromo-2,4-difluoro-3-iodobenzene (15.8 g, 39.9 mmol) in toluene (100 mL) and ion-exchanged water (30 mL), and the mixture was stirred at 100°C for 23 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, saturated saline was added, and the organic and aqueous phases were separated. After the aqueous phase was extracted with toluene, the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (hexane) to obtain 9.0 g (25.5 mmol, 64% yield) of compound j as a white solid. 1 H-NMR (400 MHz, CDCl3): δ 7.77 (t, J=6.8 Hz, 1H). ASAP MS Spectral Analysis: C 12 HD5Br2F2: Calculated 350.91, Observed 350.93 [M]

[0131] Compound k [ka]

[0132] A reaction mixture of compound j (2.1 g, 5.98 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.30 mmol), potassium acetate (4.1 g, 42.0 mmol), bis(pinacolato)diboron (7.1 g, 27.9 mmol), and 1,4-dioxane (60 mL) was stirred at 110° C. for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica gel. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica gel. The resulting solid was washed with hexane to obtain 1.84 g (4.11 mmol, 69% yield) of compound k as a white solid. 1 H-NMR (400 MHz, CDCl3): δ 8.11 (t, J=7.2 Hz, 1H), 1.36 (s, 24H).

[0133] Compound m [ka]

[0134] Compound k (8.00 g, 17.89 mmol) was dissolved in tetrahydrofuran (THF, 138 mL) and ion-exchanged water (46 mL), and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (4.35 g, 35.78 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.63 g, 0.89 mmol), and sodium carbonate (9.48 g, 89.46 mmol) were added and stirred at 75 ° C for 16 hours. The reaction vessel was cooled to room temperature, and the obtained gray solid was filtered. The solid was washed with ion-exchanged water, methanol, and THF. The collected solid was stirred in hot toluene, and the solid was filtered and washed with toluene to obtain 4.1 g (6.05 mmol, yield 34%) of black solid compound m. ASAP MS Spectral Analysis: C 42 HD 25 F2N6: Calculated value 677, Observed value 678 [M+H + ]

[0135] Compound P1 [ka]

[0136] 9H-carbazole (0.80 g, 4.79 mmol) and potassium carbonate (0.93 g, 6.71 mmol) were added to a mixture of compound m (1.30 g, 1.92 mmol) and N,N-dimethylformamide (DMF, 50 mL), and the mixture was stirred at 150°C for 3 hours. The reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate. The filtrate was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol. The crude product was purified by column chromatography (toluene / hexane = 3:1), and the solid was reprecipitated with ethyl acetate / hexane to obtain 1.60 g (1.65 mmol, yield 85.8%) of pale green compound P1. ASAP MS Spectral Analysis: C 66 H 17 D 25 N8: 972 theoretical value, 973 observed value [M+H + ]

[0137] Compound P2 [ka]

[0138] Carbazole-1,2,3,4,5,6,7,8-d8 (0.84 g, 4.79 mmol) and potassium carbonate (0.93 g, 6.71 mmol) were added to a mixture of compound m (1.30 g, 1.92 mmol) and DMF (50 mL), and the mixture was stirred at 150 ° C for 3 hours. The reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate. The filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol. The crude product obtained was purified by column chromatography (toluene / hexane = 3:1), and the solid obtained was reprecipitated with ethyl acetate / hexane to obtain 1.50 g (1.52 mmol, yield 79.1%) of pale green compound P2. ASAP MS Spectral Analysis: C66 HD 41 N8: Theoretical value 988, Observed value 989 [M+H + ]

[0139] Compound P3 [ka]

[0140] Under a nitrogen stream, potassium carbonate (1.07 g, 7.74 mmol) was added to a solution of compound m (1.75 g, 2.58 mmol) and 5H-benzofuro[3,2-c]carbazole (1.60 g, 6.22 mmol) in N-methyl-2-pyrrolidone (NMP, 90 mL), and the mixture was stirred at 120° C. for 18 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried over magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator, purified by column chromatography (toluene:hexane = 1:1), washed with methanol, and recrystallized (toluene) to obtain a yellow compound P3 (0.80 g, 0.69 mmol, yield 27%). 1 H-NMR (400 MHz, CDCl3): δ 9.51 (s, 1H), 7.57 (d, J=7.2Hz, 2H), 7.94-7.87 (m, 4H), 7.62 (d, J=7.2Hz, 2H), 7.38-7.24 (m, 12H).

[0141] (Synthesis Example 4) Synthesis of Compound P4 Compound n [ka]

[0142] Compound k (1.81 g, 4.05 mmol) was dissolved in THF (30 mL) and ion-exchanged water (10 mL), and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3.05 g, 8.25 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.15 g, 0.21 mmol), and sodium carbonate (2.20 g, 20.8 mmol) were added and stirred at 75 ° C for 16 hours. The reaction vessel was cooled to room temperature, and the obtained gray solid was filtered. The solid was washed with ion-exchanged water, methanol, and THF. The collected solid was stirred in hot toluene, and the solid was filtered and washed with toluene to obtain 3.30 g (3.82 mmol, yield 94%) of black solid compound n. ASAP MS Spectral Analysis: C 54 HD 31 F2N8: Calculated value 861.47, Observed value 862..72 [M+H + ]

[0143] Compound P4 [ka]

[0144] Carbazole-1,2,3,4,5,6,7,8-d8 (1.28 g, 7.30 mmol) and potassium carbonate (1.37 g, 9.91 mmol) were added to a mixture of compound n (2.85 g, 3.30 mmol) and DMF (65 mL), and the mixture was stirred at 150 ° C for 3 hours. The reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate. The filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol. The crude product obtained was purified by column chromatography (toluene / hexane = 3: 1), and the solid obtained was reprecipitated with ethyl acetate / hexane, to obtain 2.13 g (1.81 mmol, yield 55%) of pale green compound P4. 1 H-NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H). ASAP MS Spectral Analysis: C 78HD 47 N 10 : Theoretical value 1171.70, Observed value 1172.15 [M+H + ]

[0145] (Synthesis Example 5) Synthesis of Compound P5 Compound p [ka]

[0146] Under a nitrogen atmosphere, a 2.3 M solution of n-butyllithium in cyclohexane (21 mL, 48.3 mmol) was slowly added dropwise to a solution of 5'-bromo-1,1':3',1''-terphenyl-2,2'',3,3'',4,4'',5,5'',6,6''-d10 (12.0 g, 37.6 mmol) in THF (75 mL) at -78 °C. After stirring for 80 minutes, triisopropyl borate (12.8 mL, 56.4 mmol) was added and the reactor was heated to room temperature. After stirring for 2 hours, the mixture was cooled to 0 °C and 4N aqueous hydrochloric acid (70 mL) was added. After stirring for 30 minutes at room temperature, the organic phase and the aqueous phase were separated. The aqueous phase was extracted with diethyl ether, and the combined organic phase was washed with ion-exchanged water and saturated saline. The organic phase was concentrated, and the resulting white solid was washed with hexane to obtain 9.30 g (32.7 mmol, yield 87%) of a white compound p. 1 H-NMR (400 MHz, DMSO-d6): δ 8.26 (brs, 2H), 8.08 (d, J=1.6 Hz, 2H), 7.92-7.93 (m, 1H).

[0147] Compound q [ka]

[0148] Compound p (4.0 g, 14.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.46 g, 0.64 mmol), and potassium carbonate (3.60 g, 26.0 mmol) were added to a mixed solution of 1,5-dibromo-2,4-difluoro-3-iodobenzene (5.1 g, 13.0 mmol) in toluene (30 mL) and ion-exchanged water (10 mL), and the mixture was stirred at 100 ° C for 15 hours. The reaction solution was cooled to room temperature, saturated saline was added, and the organic phase and the aqueous phase were separated. After the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (hexane / ethyl acetate = 40: 1) and (hexane / methylene chloride = 10: 1), and the obtained white solid was washed with hexane to obtain 4.84 g (9.48 mmol, yield 73%) of compound q. 1 H-NMR (400 MHz, CDCl3): δ 7.88 (t, J=2.0 Hz, 1H), 7.81 (t, J=6.8 Hz, 1H), 7.62 (q, J=2.0 Hz, 2H). ASAP MS Spectral Analysis: C 24 H4D 10 Br2F2: Calculated 508.00, Observed 509.03 [M+H + ]

[0149] Compound r [ka]

[0150] A reaction mixture of compound q (4.8 g, 9.40 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.36 g, 0.50 mmol), potassium acetate (6.5 g, 66.2 mmol), bis(pinacolato)diboron (12.1 g, 47.6 mmol), and 1,4-dioxane (100 mL) was stirred at 110° C. for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica gel. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica gel. The resulting solid was washed with hexane to obtain 5.00 g (8.27 mmol, 88% yield) of compound r as a yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 8.15 (t, J=6.8 Hz, 1H), 7.79-7.80 (m, 1H), 7.66 (brs, 2H), 1.26 (s, 24H). ASAP MS Spectral Analysis: C 36 H 28 D 10 B2F2O4: Calculated 604.37, Observed 605.47 [M+H + ]

[0151] Compounds [ka]

[0152] Compound r (4.98 g, 8.24 mmol) was dissolved in THF (60 mL) and ion-exchanged water (20 mL), and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.10 g, 16.5 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.29 g, 0.41 mmol), and sodium carbonate (4.37 g, 41.2 mmol) were added and stirred at 75 ° C for 20 hours. The reaction vessel was cooled to room temperature, and the obtained gray solid was filtered. The solid was washed with THF and ion-exchanged water. The collected solid was stirred in hot toluene, and the solid was filtered, washed with toluene, and dried to obtain 7.98 g (7.83 mmol, yield 95%) of compound s as a gray solid. ASAP MS Spectral Analysis: C 66 H4D 36 F2N8: Calculated value 1018.56, Observed value 1019.83 [M+H + ]

[0153] Compound P5 [ka]

[0154] Carbazole-1,2,3,4,5,6,7,8-d8 (1.16 g, 6.61 mmol) and potassium carbonate (1.24 g, 8.97 mmol) were added to a mixture of compound s (3.06 g, 3.00 mmol) and DMF (60 mL), and the mixture was stirred at 150 ° C for 3 hours. The reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate. The filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol. The crude product obtained was purified by column chromatography (toluene / hexane = 1:1 to 2:1), and the solid obtained was reprecipitated with ethyl acetate / hexane to obtain 1.47 g (1.10 mmol, yield 37%) of green compound P5. 1H-NMR (400 MHz, DMSO-d6): δ 9.40 (s, 1H), 7.14 (d, J=1.6 Hz, 2H), 7.07 (d, J=1.6 Hz, 1H). ASAP MS Spectral Analysis: C 90 H4D 52 N 10 : Theoretical value 1328.80, Observed value 1329.84 [M+H + ]

[0155] (Example 1) Preparation and evaluation of thin films Vacuum deposition on a quartz substrate at a vacuum level of 1×10 -3 Compound P1 was evaporated under conditions of less than 1 Pa to form a neat thin film of compound P1 with a thickness of 100 nm. Separately, a quartz substrate was vacuum-deposited at a vacuum level of 1×10 -3 Compounds P1 and PyD2Cz were evaporated from different evaporation sources under conditions of less than Pa, and a doped thin film with a thickness of 100 nm and a concentration of compound P1 of 20 wt % was formed. Neat thin films and doped thin films were formed in the same manner using Compound P2, Compound P4, Comparative Compound A, Comparative Compound B, and Comparative Compound C instead of Compound P1. The photoluminescence of each doped thin film formed was analyzed when 302 nm excitation light was irradiated, and the emission peak wavelength (λmax), photoluminescence quantum yield (PLQY), and the lifetime of the delayed fluorescence component (τ2) were measured. In addition, the HOMO energy and LUMO energy were also measured using each neat thin film formed. The results are shown in the table below. A neat thin film of compound P5 was formed in the same manner and measured, and the HOMO energy of compound P5 was 6.13 eV and the LUMO energy was 3.45 eV. It was confirmed that the compound represented by the general formula (1) has high luminescence efficiency, short delayed fluorescence lifetime, and favorable luminescence characteristics. 1 ~Ar 4 It has also been confirmed that compounds in which at least one of the groups is a heteroaryl group exhibit particularly excellent luminescence properties. [Table 5]

[0156] (Example 2) Preparation and evaluation of thin films Vacuum deposition on a quartz substrate at a vacuum level of 1×10 -3 Compounds P1 and H1 were evaporated from different evaporation sources under conditions of less than 1 Pa, and a doped thin film with a concentration of compound P1 of 30 wt % was formed to a thickness of 100 nm. Doped thin films were formed in the same manner except that compound P2, compound P4, and compound P5 were used instead of compound P1. The photoluminescence of each doped thin film was analyzed by irradiating it with 302 nm excitation light, and the lifetime (τ2) of the delayed fluorescence component and the degree of orientation (S value) were measured. The degree of orientation was measured using the method described in Scientific Reports 2017, The results are shown in the table below. It was confirmed that the compound represented by the general formula (1) has a short delayed fluorescence lifetime and exhibits good orientation. In addition, the compound P4 and compound P5, which are Ar 1 ~Ar 4 It has also been confirmed that compounds in which at least one of the groups is a heteroaryl group have a particularly short delayed fluorescence lifetime and exhibit excellent alignment properties. [Table 6]

[0157] (Example 3) Preparation and evaluation of organic electroluminescence device Each thin film was deposited on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm by vacuum deposition at a vacuum degree of 5.0 × 10 -5Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, TrisPCz was further formed thereon to a thickness of 10 nm, and H1 was formed thereon to a thickness of 5 nm. Next, H1 and compound P1 were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm to serve as an emitting layer. The concentration of H1 in the emitting layer was 70 mass %, and the concentration of compound P1 was 30 mass %. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30 mass % and 70 mass %, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, to form an organic electroluminescence element. Doped thin films were formed in the same manner except that Compounds P2, P4, P5, Comparative Compound B, and Comparative Compound C were used instead of Compound P1. When each organic electroluminescence device was driven, blue delayed fluorescence was observed. 2 The external quantum efficiency (EQE) and the time until the luminous intensity reached 95% at the start of driving (LT95) were measured when the organic electroluminescence element was driven at 1000 rpm. The results are shown in the table below. LT95 is shown as a relative value, with the value for the organic electroluminescence element using comparative compound B taken as 1. It was confirmed that the organic light-emitting element using the compound represented by general formula (1) has high luminous efficiency and a long element life. In addition, when the organic electroluminescence element using the compound P4 or P5 is used in the presence of Ar 1 ~Ar 4 It has also been confirmed that an organic light-emitting device using a compound in which at least one of the groups is a heteroaryl group has particularly good luminous efficiency and device life. [Table 7]

[0158] [ka] [ka] [Industrial Applicability]

[0159] The compound represented by the general formula (1) and the organic light-emitting device using the compound have good light-emitting properties, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 [In general formula (1), R １ represents a hydrogen atom or a deuterium atom; R2 is a group represented by the following general formula (2); R3 and R ５ are each independently a substituted or unsubstituted carbazol-9-yl group, R ４ is a substituted or unsubstituted aryl group. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group. 【Chemistry 2】 In the general formula (2), X １ ~X ３ Each independently represents N or C(R), but X １ ~X ３ At least one of Ar is N. R represents a hydrogen atom, a deuterium atom, or a substituent. ３ and Ar ４ each independently represents a substituted or unsubstituted aryl group. １ represents a single bond or a divalent linking group. * represents the bonding position. The compound represented by general formula (1) has at least one deuterium atom.

2. The compound according to claim 1 , wherein the substituted or unsubstituted aryl group is an unsubstituted aryl group or an aryl group substituted with an aryl group.

3. X １ ~X ３ The compound of claim 1 , wherein is N.

4. L １ The compound of claim 1 , wherein is a single bond.

5. R １ The compound according to claim 1 , wherein is a hydrogen atom.

6. A light-emitting material comprising the compound according to any one of claims 1 to 5.

7. A delayed fluorescent material of the compound according to any one of claims 1 to 5.

8. An organic light-emitting device comprising the compound according to any one of claims 1 to 5 and a host material or a dopant material in the same layer.

9. The organic light-emitting device of claim 8 , wherein the layer comprises the dopant material.

10. The organic light-emitting device according to claim 8 , wherein the amount of light emitted from the dopant material is greater than the amount of light emitted from the compound.

11. The organic light-emitting device of claim 8 , wherein the layer comprises the host material.

12. The organic light-emitting device according to claim 11 , wherein the host material is a compound represented by the following general formula (4): 【Transformation 3】 [In the general formula (4), X １１ is O, S, N (R Ａ ) or C(R Ｂ ) (R Ｃ ) represents. １１ and A １２ R are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring, and these rings may be further condensed with other rings or may be substituted. １１１ ~R １１４ , R Ｂ , R Ｃ R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. １１５ R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond to L. Ａ represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond to L. １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , two adjacent R １１５ , R Ｂ and R Ｃ may be bonded to each other to form a cyclic structure. n represents an integer of 3 or 4. L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group formed by bonding two or more of these.

13. The organic light-emitting device according to claim 11 , wherein the compound emits the greatest amount of light among the materials contained in the layer.

14. The organic light-emitting device according to claim 8 , which emits delayed fluorescence.

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