Organic light-emitting element

Abstract

The organic light-emitting element using the compound of the following general formula has excellent light-emitting characteristics. R1 to R5 are H, D, an alkyl group, an aryl group, a donor group, a triazinyl group substituted with Ar3 and Ar4, or the like, R2 or R3 is the triazinyl group, or the like, and two or more of R1 to R5 are donor groups; and Ar1 to Ar4 are aryl groups and heteroaryl groups. In this connection, one or more of R1-R5 are donor groups having a fused ring structure having four or more rings, or one or more of Ar1-Ar4 are heteroaryl groups.

Description

Technical Field

[0001] This invention relates to organic light-emitting elements, such as organic electroluminescent elements. Background Technology

[0002] Organic light-emitting elements (OLEDs) are light-emitting devices that utilize organic materials. They can be manufactured through coating and have attracted considerable attention in recent years due to their lack of the use of rare elements. Organic electroluminescent elements (organic EL elements) are particularly noteworthy because they emit light self-emittingly and do not require backlighting, allowing for the fabrication of lightweight and flexible devices. Furthermore, they exhibit fast response and high visibility, making them a promising next-generation light source. Therefore, research is actively underway related to the development of materials useful for organic light-emitting elements, particularly organic electroluminescent elements. In particular, research on luminescent materials is currently booming. While fluorescent and phosphorescent materials have been known as luminescent materials, fluorescent materials suffer from low luminous efficiency, and phosphorescent materials are expensive due to the presence of rare metals and are difficult to emit a deep blue light. In recent years, delayed-fluorescence materials have been developed to address these issues.

[0003] Delayed fluorescence materials are those that emit fluorescence upon returning to the ground state after a reverse intersystem crossing from an excited triplet state to an excited singlet state in the excited state. The fluorescence generated via this pathway is observed later than fluorescence from an excited singlet state directly generated from the ground state (normal fluorescence), hence the name delayed fluorescence. For example, in the case of excitation of luminescent compounds via carrier injection, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%, therefore, improving luminescence efficiency solely through fluorescence from the directly generated excited singlet state is limited. On the other hand, in delayed fluorescence materials, in addition to the excited singlet state, the excited triplet state can also be utilized for fluorescence emission via the aforementioned reverse intersystem crossing pathway, thus achieving higher luminescence efficiency compared to conventional fluorescent materials.

[0004] After clarifying this principle, various delayed fluorescence materials have been discovered through various studies. Among them are compounds containing multiple benzene rings substituted with donor and acceptor groups. For example, a compound having a skeleton with a benzene ring substituted with a carbazole-9-yl group as a donor group, a cyano group as an acceptor group, and a substituted triazine group has been proposed for use in organic light-emitting elements (see Patent Document 1).

[0005] Previous technical documents

[0006] Patent documents

[0007] Patent Document 1: WO2019 / 191665A1 Summary of the Invention

[0008] The technical problem to be solved by the invention

[0009] To date, no material has been provided that, even for materials emitting delayed fluorescence, possesses extremely good properties and poses no practical problems. Therefore, it would be even more useful to provide delayed fluorescence materials with superior properties. However, improvements to delayed fluorescence materials are still in the experimental stage, and it is not easy to generalize the chemical structures of useful luminescent materials.

[0010] In this context, the inventors conducted repeated studies with the aim of providing compounds that are more useful as delayed fluorescence materials for light-emitting elements. Furthermore, they conducted in-depth studies to derive general formulas of compounds that are more useful as delayed fluorescence materials and to generalize them, and to use these compounds in organic light-emitting elements.

[0011] means for solving technical problems

[0012] As a result of in-depth research conducted to achieve the aforementioned objectives, the inventors discovered that compounds with structures satisfying specific conditions are useful as luminescent materials and can provide excellent organic light-emitting elements. The present invention is made based on this insight, and specifically, has the following structure.

[0013] [1] An organic light-emitting element comprising a compound represented by the following general formula (1) and a host material or dopant material in the same layer.

[0014] [Chemical Formula 1]

[0015] General formula (1)

[0016]

[0017] In general formula (1), R 1 ~R 5 Each of these groups independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the general formula (2) below. Furthermore, R... 2 or R 3 For the group represented by the following general formula (2), R 1 ~R 5 Two or more of them are donor groups. Ar 1 and Ar 2 Each can be used independently to represent either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0018] [Chemical Formula 2]

[0019] General formula (2)

[0020]

[0021] In general formula (2), X 1 ~X 3 Let N or C(R) represent them independently, but X 1 ~X 3 At least one of them is N. R represents a hydrogen atom, a deuterium atom, or a substituent. Ar 3 and Ar 4 Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L 1 Indicates a single bond or a divalent linker. * Indicates the bonding position.

[0022] Wherein, the compound represented by the general formula (1) is R 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings, or Ar 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups), or R 1 ~R 5 and Ar 1 ~Ar 4 Both of these conditions must be met.

[0023] [2] According to the organic light-emitting element described in [1], wherein R of the general formula (1) is... 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings.

[0024] [3] According to the organic light-emitting element described in [2], wherein,

[0025] R in the general formula (1) 1 ~R 5 One or more of them are donor groups represented by the following general formula (3).

[0026] [Chemical Formula 3]

[0027] General formula (3)

[0028]

[0029] In general formula (3), X represents O, S or NR. 14 R 11 ~R 13 Each can be used independently to represent a deuterium atom or a substituent. R 14R represents an aryl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium, alkyl, and aryl, or an alkyl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium and aryl. 11 Each other, R 12 Each other, R 13 They can be bonded together to form a ring structure. n11 and n13 independently represent any integer from 0 to 4, and n12 represents any integer from 0 to 2.

[0030] [4] According to the organic light-emitting element of [2] or [3], wherein the Ar of the general formula (1) and (2) 1 ~Ar 4 Each aryl group can be independently substituted or unsubstituted.

[0031] [5] An organic light-emitting element according to any one of [1] to [3], wherein the Ar of the general formula (1) and (2) is... 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups).

[0032] [6] According to the organic light-emitting element described in [5], wherein the Ar of the general formulas (1) and (2) is... 1 ~Ar 4 One or more of them are heteroaryl groups with a 5-membered ring bonded by a nitrogen atom.

[0033] [7] An organic light-emitting element according to any one of [1] to [6], wherein the R of the general formula (1) 2 The group represented by the general formula (2) is called the group.

[0034] [8] An organic light-emitting element according to any one of [1] to [6], wherein the R of the general formula (1) 3 The group represented by the general formula (2) is called the group.

[0035] [9] An organic light-emitting element according to any one of [1] to [8], wherein the donor group is a substituted or unsubstituted carbazole-9-yl.

[0036]

[10] An organic light-emitting element according to any one of [1] to [9], wherein the R of the general formula (1) 1 ~R 5 Three of them are donor groups.

[0037]

[11] An organic light-emitting element according to any one of [1] to

[10] , wherein X of the general formula (2) 1 ~X 3Let N be the number of elements in the array.

[0038]

[12] An organic light-emitting element according to any one of [1] to

[11] , wherein the L of the general formula (2) 1 It is a single key.

[0039]

[13] An organic light-emitting element according to any one of [1] to

[12] , wherein R of the general formula (1) 1 It is a hydrogen atom.

[0040]

[14] An organic light-emitting element according to any one of [1] to

[13] , wherein the compound has at least one deuterium atom.

[0041]

[15] An organic light-emitting element according to any one of [1] to

[14] , wherein the layer comprises the doped material.

[0042]

[16] According to the organic light-emitting element of

[15] , the amount of light emitted from the doped material is greater than the amount of light emitted from the compound.

[0043]

[17] An organic light-emitting element according to any one of [1] to

[16] , wherein the doping material is a compound represented by the following general formula (4).

[0044] [Chemical Formula 4]

[0045] General formula (4)

[0046]

[0047] In general formula (4), X 1 and X 2 One of them is a nitrogen atom and the other is a boron atom. R 1 ~R 26 A 1 A 2 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 7 and R 8 R 8 and R 9 R 9 and R 10 R10 and R 11 R 11 and R 12 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 17 and R 18 R 18 and R 19 R 19 and R 20 R 20 and R 21 R 21 and R 22 R 22 and R 23 R 23 and R 24 R 24 and R 25 R 25 and R 26 They can bond together to form a ring structure. Among them, in X... 1 When R is a nitrogen atom, 17 and R 18 They bond together to form single bonds to form a pyrrole ring, in X 2 When R is a nitrogen atom, 21 and R 22 They bond together to form single bonds, thus forming a pyrrole ring. Specifically, in X... 1 For nitrogen atoms, R 7 and R 8 and R 21 and R 22 A six-membered ring is formed through nitrogen atom bonding, R 17 and R 18 When they bond together to form a single bond, R 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 Any one of them bonds with each other to form an aromatic ring or a heteroaromatic ring. Furthermore, in X... 1 For boron atoms, X 2 For nitrogen atoms, R7 and R 8 R 17 and R 18 When they bond together to form a ring structure containing boron atoms, this ring structure is a 5- to 7-membered ring. In the case of a 6-membered ring, R 7 and R 8 R 17 and R 18 They bond together to form -B(R) 32 -, -CO-, -CS- or -N(R) 27 )-. R 27 This represents a hydrogen atom, a deuterium atom, or a substituent.

[0048]

[18] An organic light-emitting element according to any one of [1] to

[17] , wherein the layer comprises the host material.

[0049]

[19] According to the organic light-emitting element of

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

[0050]

[20] An organic light-emitting element according to any one of [1] to

[19] , wherein the host material is a compound represented by the following general formula (5).

[0051] [Chemical Formula 5]

[0052] General formula (5)

[0053]

[0054] In general formula (5), X 11 Represents O, S, N(R) A ) or C(R B (R) C A 11 and A 12 Each ring can be independently a benzene ring, furan ring, thiol ring, pyrrole ring, or cyclopentadiene ring, and these rings can be further fused with other rings or substituted. R 111 ~R 114 R B R C Each of these can independently represent 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. R 115 Each of these can independently represent 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 with L. R AThis indicates a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L. R 111 and R 112 R 112 and R 113 R 113 and R 114 2 adjacent R 115 R B and R C They can bond together to form a cyclic structure. n represents any integer from 3 to 4. L represents a single bond, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a linking group consisting of two or more of these.

[0055]

[21] The organic light-emitting element according to any one of [1] to

[20] emits delayed fluorescence.

[0056] Invention Effects

[0057] The organic light-emitting element of the present invention exhibits excellent light-emitting characteristics. Detailed Implementation

[0058] The present invention will be described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the invention, but the invention is not limited to such embodiments or specific examples. Furthermore, in this specification, the numerical range indicated by "~" represents the range of values ​​described before and after "~" as lower and upper limits. Also, in the compounds used in the present invention, some or all of the hydrogen atoms present within the molecule can be replaced by deuterium atoms (…). 2 Hydrogen atoms are substituted with H or deuterium (D). In the chemical structural formulas of this specification, the hydrogen atom is represented by H or its representation is omitted. For example, when the atom representing the carbon atom bonded to the ring skeleton of the benzene ring is omitted, H forms a carbon atom bond with the ring skeleton at the omitted position. In this specification, the term "substituent" refers to an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that the hydrogen atom can be substituted by a deuterium atom or a substituent.

[0059] [Compounds represented by general formula (1)]

[0060] The compounds represented by the following general formula (1) will be described.

[0061] [Chemical Formula 6]

[0062] General formula (1)

[0063]

[0064] In general formula (1), R 1 ~R 5 Each of these groups independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the general formula (2) below. Furthermore, R... 2 or R 3 For the group represented by the following general formula (2), R 1 ~R 5 Two or more of them are donor groups. Ar 1 and Ar 2 Each can be represented independently as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The compound represented by general formula (1) is R. 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings, or Ar 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups), or R 1 ~R 5 and Ar 1 ~Ar 4 Both of these conditions must be met. Additionally, Ar 3 and Ar 4 is a group present in general formula (2).

[0065] R 1 ~R 5 The alkyl group that can be used can be any one of straight-chain, branched, or cyclic. Furthermore, two or more of the straight-chain, cyclic, and branched portions can be mixed together. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodexyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl substituent can be further substituted with, for example, a deuterium atom, aryl, alkoxy, aryloxy, or a halogen atom. In one aspect of the invention, the substituent of the alkyl group is one or more selected from the group consisting of aryl and deuterium atoms. In a preferred embodiment of the invention, the alkyl group is unsubstituted, for example, it can be selected from the group consisting of methyl, ethyl, isopropyl and tert-butyl.

[0066] R 1 ~R 5 Ar 1 and Ar 2The aryl group can be a monocyclic ring or a fused ring composed of two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example, selected from 2 to 4. Specific examples of the ring include benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, and triphenylene rings. In one aspect of the invention, the aryl group is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphth-1-yl, or a substituted or unsubstituted naphth-2-yl, preferably a substituted or unsubstituted phenyl. Regarding the substituents of the aryl group, for example, they can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In one aspect of the invention, the substituents of the aryl group are selected from one or more of the group consisting of alkyl, aryl, and deuterium atoms. In a preferred aspect of the invention, the aryl group is substituted by at least one deuterium atom. In one aspect of the invention, the aryl group is unsubstituted.

[0067] In the following, R is cited. 1 ~R 5 Ar 1 and Ar 2 Specific examples of substituted or unsubstituted aryl groups that can be used. The aryl groups that can be used in this invention are not limited by the following specific examples. In the following specific examples, * indicates a bonding position. Furthermore, the methyl group is omitted. Therefore, Ar2 to Ar7 represent structures substituted with a methyl group.

[0068] [Chemical Formula 7]

[0069]

[0070]

[0071]

[0072] Apart from the specific examples mentioned above, groups in Ar1 to Ar26 that replace all hydrogen atoms with deuterium atoms are exemplified here as Ar47 to Ar72.

[0073] In one aspect of the invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar1 to Ar72. In one aspect of the invention, R 1 ~R 5 The aryl group that can be used is Ar1 or Ar47. In one aspect of the invention, R 1 ~R 5 The aryl groups that can be used are selected from the group consisting of Ar2-Ar11, Ar27-Ar36, and Ar48-Ar57. In one aspect of the invention, R1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar12-Ar20, Ar37-Ar45, and Ar58-Ar66. In one aspect of the invention, R 1 ~R 5 The aryl groups that can be used are selected from the group consisting of Ar22-Ar26 and Ar68-Ar72. In a preferred embodiment of the invention, R 1 ~R 5 The aryl groups that can be used are selected from the group consisting of Ar1, Ar12-Ar15, Ar24, Ar37-Ar40, Ar47, Ar58-Ar61, and Ar70.

[0074] In one aspect of the invention, Ar 1 Or Ar 2 The aryl group that can be used is selected from the group consisting of Ar1 to Ar72. In one aspect of the invention, Ar... 1 Or Ar 2 The aryl group that can be used is Ar1 or Ar47. In one aspect of the invention, Ar... 1 Or Ar 2 The aryl groups that can be used are selected from the group consisting of Ar2-Ar11, Ar27-Ar36, and Ar48-Ar57. In one aspect of the invention, Ar... 1 Or Ar 2 The aryl group that can be used is selected from the group consisting of Ar12-Ar20, Ar37-Ar45, and Ar58-Ar66. In a preferred embodiment of the invention, R 1 ~R 5 The aryl groups that can be used are selected from the group consisting of Ar1, Ar12-Ar14, Ar37-Ar40, Ar47, and Ar58-Ar61.

[0075] R in general formula (1) 1 ~R 5 At least two of them are donor groups. R 1 ~R 5 The donor groups that can be used do not contain substituted or unsubstituted aryl groups.

[0076] Regarding the "donor group," selection can be made from groups with negative Hammett σp values. Regarding the "acceptor group," selection can be made from groups with positive Hammett σp values. Hammett's σp value, proposed by L.P. Hammett, quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is the following equation holding between the substituents in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0077] log(k / k0)=ρσp

[0078] or

[0079] log(K / K0)=ρσp

[0080] The constant (σp) is specific to the substituents in the reaction. In the above formula, k0 represents the rate constant of the benzene derivative without substituents, k represents the rate constant of the benzene derivative substituted with substituents, K0 represents the equilibrium constant of the benzene derivative without substituents, K represents the equilibrium constant of the benzene derivative substituted with substituents, and ρ represents the reaction constant determined by the type and conditions of the reaction. For a description of the "Hammett's σp value" mentioned in this invention and the number of each substituent, please refer to the record of the σp value mentioned in Hansch, C. et.al., Chem. Rev., 91, 165–195 (1991).

[0081] R 1 ~R 5 The σp of the donor group that can be used is preferably -0.3 or less, more preferably -0.5 or less, and even more preferably -0.7 or less. For example, it can be selected from the range of -0.9 or less or from the range of -1.1 or less.

[0082] The donor group in this invention is preferably a group containing a substituted amino group. It can be a substituted amino group, or an aryl group formed by the bonding of substituted amino groups, wherein the phenyl group is formed by the bonding of substituted amino groups. In a preferred embodiment of this invention, the donor group is a substituted amino group.

[0083] The substituents bonded to the nitrogen atom in the substituted amino group are preferably substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, more preferably substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl. In particular, the substituted amino group is preferably a substituted or unsubstituted diarylamino or a substituted or unsubstituted diheteroarylamino. The two aryl groups constituting the diarylamino can be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino can be bonded to each other.

[0084] R 1 ~R 5 The donor group that can be used is preferably the group represented by the following general formula (a).

[0085] [Chemical Formula 8]

[0086] General formula (a)

[0087]

[0088] In general formula (a), Z1 Indicates CR 14 Or N, Z 2 CR 15 Or N, Z 3 CR 16 Or N, Z 4 Indicates CR 17 Or N. Z 5 Represents C or N, Ar 5 Indicates a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. R 14 and R 15 R 15 and R 16 R 16 and R 17 They can bond together to form a ring structure.

[0089] Z 1 ~Z 4 The number of N values ​​is preferably 0 to 3, more preferably 0 to 2. In one embodiment of the invention, Z... 1 ~Z 4 The number of N is 1. In one aspect of the invention, Z 1 ~Z 4 The number of N values ​​is 0.

[0090] R 14 ~R 17 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent.

[0091] Regarding substituents, for example, selection can be made from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In R... 14 ~R 17 When two or more substituents are represented in R, these two or more substituents can be the same or different. 14 ~R 17 The 0 to 2 of them are preferably substituents, for example, one can be a substituent or none can be a substituent (R). 14 ~R 17 (It consists of hydrogen or deuterium atoms).

[0092] R 14 and R 15 R 15 and R 16 R 16 and R 17They can bond together to form a cyclic structure. The cyclic structure can be any of aromatic rings, heteroaromatic rings, aliphatic hydrocarbon rings, and aliphatic heterocycles, and can also be a fused ring of these. Aromatic rings and heteroaromatic rings are preferred. As aromatic rings, substituted or unsubstituted benzene rings can be cited as examples. Benzene rings can be further fused with other benzene rings, or with heterocycles such as pyridine rings. Heteroaromatic rings refer to rings containing heteroatoms as ring skeleton atoms and exhibiting aromaticity, preferably 5- to 7-membered rings, for example, 5-membered or 6-membered rings can be used. In one aspect of the invention, furan rings, thiophene rings, and pyrrole rings can be used as heteroaromatic rings. In a preferred aspect of the invention, the cyclic structure 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 benzofuran, benzothiophene, and indole described herein can be unsubstituted, or substituted with substituents selected from substituent group A, B, C, D, or E. The nitrogen atom of the pyrrole ring constituting the indole is preferably bonded to a substituted or unsubstituted aryl group as a substituent, for example, a substituent selected from any of substituent groups A to E. The cyclic structure can be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the invention, R... 14 and R 15 R 15 and R 16 R 16 and R 17 One group of elements bonds together to form a ring structure. In one embodiment of the invention, R 14 and R 15 R 15 and R 16 R 16 and R 17 They do not bond with each other to form a ring structure.

[0093] In general formula (a), Z 5 Represents C or N, Ar 5 This indicates a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the invention, Z 5 For C, Ar 5 Z is a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one aspect of the invention, Z 5 For N, Ar 5 These are heterocyclic aromatic rings, whether substituted or not.

[0094] As Ar 5Aromatic rings that can be used include, for example, the benzene ring. The benzene ring can be further fused with other benzene rings, or with heterocycles such as the pyridine ring. Ar 5 The heteroaromatic ring that can be used is preferably a 5- to 7-membered ring, for example, a 5-membered or 6-membered ring. In one aspect of the 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 aspect of the invention, Z 5 C represents the heteroaromatic ring, which 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. In one embodiment of the invention, Z... 5 The N-aryl ring is a pyrrole ring of indole, either substituted or unsubstituted, or an imidazole ring of benzimidazole, either substituted or unsubstituted. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole described herein can be unsubstituted, or substituted with substituents selected from substituent group A, B, C, D, or E.

[0095] Z in general formula (a) 5 When the group is C, it is preferably the group represented by the following general formula (b).

[0096] [Chemical Formula 9]

[0097] General formula (b)

[0098]

[0099] In general formula (b), Z 1 CR 14 Or N, Z 2 Indicates CR 15 Or N, Z 3 CR 16 Or N, Z 4 CR 17 Or N, Z 6 CR 18 Or N, Z 7 CR 19 Or N, Z 8 CR 20 Or N, Z 9 CR 21 Or N. R 14 and R 15 R 15 and R 16 R16 and R 17 R 18 and R 19 R 19 and R 20 R 20 and R 21 They can bond together to form a ring structure.

[0100] Regarding Z in general formula (b) 1 ~Z 4 R 14 ~R 17 Please refer to the corresponding explanation in general formula (a). Z in general formula (b) 6 ~Z 9 R 18 ~R 21 In sequence with Z of general formula (a) 1 ~Z 4 R 14 ~R 17 Correspondingly, regarding these contents, you can refer to the Z of general formula (a). 1 ~Z 4 R 14 ~R 17 Explanation.

[0101] In one aspect of the invention, Z 1 ~Z 4 Z 6 ~Z 9 The number of N values ​​is preferably 0 to 2, more preferably 0 or 1. In one embodiment of the invention, Z... 1 ~Z 4 Z 6 ~Z 9 The number of N is 1. In a preferred embodiment of the invention, Z 1 ~Z 4 Z 6 ~Z 9 The number of N is 0. When it is 0, it indicates that the carbazo-9-yl group is substituted or unsubstituted.

[0102] R 1 ~R 5The donor group that can be used is preferably a substituted or unsubstituted carbazole-9-yl group. The carbazole-9-yl group can be unsubstituted, or it can be substituted by a substituent selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. Furthermore, the two benzene rings constituting the carbazole-9-yl group can be further fused with one or more rings. In a preferred embodiment of the invention, R... 1 ~R 5 The donor group that can be used is a carbazole-9-yl group that can be substituted by a group selected from substituent group E and can be fused with one or more rings. When the unfused carbazole-9-yl group is substituted, the substitution position is not particularly limited, but it is preferably at least one of positions 2 to 7, more preferably at least one of positions 3 or 6, and even more preferably at positions 3 and 6.

[0103] In one aspect of the invention, R 1 ~R 5 The donor group that can be used is a carbazole-9-yl group fused with one or more rings, which will be referred to below as "cyclic fused carbazole-9-yl". 1 ~R 5 The cyclic fused carbazole-9-yl group can be unsubstituted, or substituted with a substituent selected from substituent group A, substituent selected from substituent group B, substituent selected from substituent group C, substituent selected from substituent group D, or substituent selected from substituent group E. Preferably, it is unsubstituted or substituted with a substituent selected from substituent group E. In one embodiment of the invention, the cyclic fused carbazole-9-yl group is unsubstituted. In a preferred embodiment of the invention, the cyclic fused carbazole-9-yl group is substituted with an aryl group that can be substituted by one atom or group selected from the group consisting of deuterium, alkyl, and aryl, or by a combination of two or more groups.

[0104] The total number of fused rings in the 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 invention, the number of rings constituting the fused ring is 5. Furthermore, the number of rings described herein includes the number of rings of the fused carbazole (i.e., 3).

[0105] The fused carbazole-9-yl group is a group bonded to the 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 can be any one of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, and can also be a ring formed by further fusion of these. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of aromatic hydrocarbon rings include substituted or unsubstituted benzene rings. The benzene ring can be further fused with other benzene rings, or with heterocycles such as pyridine rings. An aromatic heterocycle refers to a ring containing heteroatoms as ring skeleton constituent atoms and exhibiting aromaticity, preferably a 5- to 7-membered ring, for example, a 5-membered or 6-membered ring. In one aspect of the invention, a furan ring, a thiophene ring, or a pyrrole ring can be used as the aromatic heterocycle. In one aspect of the invention, the fused ring 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. Furthermore, the nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from substituent group E (except in the case of only a deuterium atom), and more preferably to an aryl group that can be substituted with an alkyl or aryl group. In the invention, a carbazole-9-yl ring formed by fusion of one or more atoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms as ring skeleton constituent atoms is preferably used. Carbazole-9-yl rings formed by fusion of benzofuran structures, carbazole-9-yl rings formed by fusion of benzothiophene structures, and carbazole-9-yl rings formed by fusion of indole structures are preferably used. In one aspect of the invention, a carbazole-9-yl ring formed by fusion of at least one benzofuran structure is used, for example, two or more. In one aspect of the invention, a carbazole-9-yl group having at least one benzothiophene fused together is used, for example, having two or more.

[0106] As a cyclic fused carbazole-9-yl, it can be substituted or unsubstituted benzofuran[2,3-a]carbazole-12-yl, substituted or unsubstituted benzofuran[3,2-a]carbazole-12-yl, substituted or unsubstituted benzofuran[2,3-b]carbazole-7-yl, substituted or unsubstituted benzofuran[3,2-b]carbazole-11-yl, substituted or unsubstituted benzofuran[2,3-c]carbazole-8-yl, or substituted or unsubstituted benzofuran[3,2-c]carbazole-5-yl. Furthermore, as a cyclic fused carbazole-9-yl group, substituted or unsubstituted benzothieno[2,3-a]carbazole-12-yl, substituted or unsubstituted benzothieno[3,2-a]carbazole-12-yl, substituted or unsubstituted benzothieno[2,3-b]carbazole-7-yl, substituted or unsubstituted benzothieno[3,2-b]carbazole-11-yl, substituted or unsubstituted benzothieno[2,3-c]carbazole-8-yl, or substituted or unsubstituted benzothieno[3,2-c]carbazole-5-yl can also be used. Furthermore, as a cyclic fused carbazole-9-yl group, substituted or unsubstituted 11-phenylindolo[2,3-a]carbazole-12-yl, substituted or unsubstituted 5-phenylindolo[3,2-a]carbazole-12-yl, substituted or unsubstituted 5-phenylindolo[2,3-b]carbazole-7-yl, substituted or unsubstituted 5-phenylindolo[3,2-b]carbazole-11-yl, substituted or unsubstituted 5-phenylindolo[2,3-c]carbazole-8-yl, or substituted or unsubstituted 12-phenylindolo[3,2-a]carbazole-5-yl can also be used.

[0107] When the cyclic fused carbazole-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, for example, 1 or 2. In a preferred embodiment of the invention, either the 3-position or the 6-position of the cyclic fused carbazole-9-yl group is substituted. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there is at least one substituent at the para-position of the benzene ring. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there is at least one substituent only at the para-position of the benzene ring. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there are substituents at all substituted para-positions of the benzene ring.

[0108] In the following, R of general formula (1) is shown. 1 ~R 5 Specific examples of donor groups that may be used. However, the donor groups that may be used in this invention are not to be limited by the following specific examples.

[0109] First, specific examples of substituted or unsubstituted carbazole-9-yl groups with a 3-ring fused ring structure are given below. In these examples, Ph represents phenyl (C6H5), and * indicates the bonding position. The methyl group is omitted, so for example, D2 has one methyl group. The deuterated methyl group is represented as CD3. Furthermore, C6D5 represents a phenyl group where all hydrogen atoms are deuterated. D represents a deuterium atom.

[0110] [Chemical Formula 10]

[0111]

[0112]

[0113]

[0114]

[0115] Groups in which all hydrogen atoms present in D1 to D31 are replaced with deuterium atoms are disclosed as D55 to D85. Next, specific examples of donor groups having fused ring structures with four or more rings are given below.

[0116] [Chemical Formula 11]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] The group that replaces all hydrogen atoms in D86 to D456 and D696 to D762 with deuterium atoms is disclosed as D763 to D1210.

[0157] In one aspect of the invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1 to D1210. In one aspect of the invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1 to D85. In one aspect of the invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D86 to D1210. In one aspect of the invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D86-D695, D704-D1133, and D1142-D1210. In one aspect of the invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D696~D703 and D1134~D1141.

[0158] R in general formula (1) 1 ~R 5 Two or more of them are donor groups. In one embodiment of the invention, R 1 ~R 5 Two or three of them are donor groups. In a preferred embodiment of the invention, R 1 ~R 5 Two of them are donor groups. In a preferred embodiment of the invention, R 1 ~R 5 Three of them are donor groups. In one embodiment of the invention, at least R 3 As a donor group. In one embodiment of the invention, at least R... 4 As a donor group. In one embodiment of the invention, at least R... 5 As a donor group. In one embodiment of the invention, only R... 3 As a donor group. In one embodiment of the invention, only R... 4 As a donor group. In one embodiment of the invention, only R... 5 As a donor group. In one embodiment of the invention, only R... 3 and R 5 As a donor group. In one embodiment of the invention, only R... 2 and R 5 As a donor group. In one embodiment of the invention, only R... 2 and R 4As a donor group. In one embodiment of the invention, only R... 3 R 4 and R 5 As a donor group. In one embodiment of the invention, only R... 2 R 4 and R 5 It is a donor group. In R 1 ~R 5 When two or more of the groups are donor groups, they can be the same or different.

[0159] R 1 ~R 5 The number of hydrogen or deuterium atoms is 0 to 2, preferably 0 or 1, for example, 1 or 0. For example, R 1 It consists of hydrogen or deuterium atoms. Compared to R... 1 ~R 5 Compounds containing three hydrogen or three deuterium atoms exhibit superior luminescent properties. 1 ~R 5 The number of aryl groups, whether substituted or unsubstituted, is 0 or 1, preferably 1. It can also be 0. R 1 ~R 5 The number of substituted or unsubstituted alkyl groups is 0 to 3, preferably 0 to 2, but can be 1 or 0.

[0160] In one aspect of the invention, R 1 ~R 5 The groups are selected independently from hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, donor groups, and groups represented by general formula (2). In one aspect of the invention, R 1 ~R 5 The groups are selected independently from hydrogen atoms, deuterium atoms, donor groups, and groups represented by general formula (2). In one aspect of the invention, R 1 ~R 5 The groups can be selected independently from hydrogen atoms, deuterium atoms, substituted or unsubstituted carbazole-9-yl groups that can fused rings, and groups represented by general formula (2).

[0161] Ar of general formula (1) 1 and Ar 2The heteroaryl group can be a monocyclic ring or a fused ring composed of two or more rings. When it is a fused ring, the number of fused rings is preferably 2 to 6, for example, it can be selected from 2 to 4. Specific examples of the ring include pyridine rings, pyrimidine rings, and pyrrole rings, which can be further fused with other rings. Specific examples of heteroaryl groups include 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazole-9-yl, carbazole-1-yl, carbazole-2-yl, carbazole-3-yl, and carbazole-4-yl. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and can be selected from the range of 5 to 16 or from the range of 5 to 12.

[0162] In one aspect of the invention, Ar 1 and Ar 2 The aryl group can be substituted or not.

[0163] In general formula (1), R 2 or R 3 It is the group represented by the following general formula (2). Furthermore, R 1 R 4 R 5 Alternatively, the group represented by the following general formula (2) can be used.

[0164] [Chemical Formula 12]

[0165] General formula (2)

[0166]

[0167] In general formula (2), X 1 ~X 3 Let N or C(R) represent them independently, but X 1 ~X 3 At least one of them is N. R represents a hydrogen atom, a deuterium atom, or a substituent. Ar 3 and Ar 4 Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L 1 Indicates a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. * indicates the bond position.

[0168] L in general formula (2) 1 This indicates a single bond or a divalent linking group. Examples of divalent linking groups include substituted or unsubstituted arylene groups and substituted or unsubstituted heteroarylene groups. In a preferred embodiment of the invention, L... 1 It is a single bond. In one embodiment of the invention, L 1 The aryl group may be substituted or unsubstituted. In one aspect of the invention, L1 This refers to substituted or unsubstituted heteroarylene groups. For information on the aryl moiety constituting the arylene group, please refer to the above R... 1 ~R 5 The description and preferred range of aryl groups are listed in the description section. Examples of heteroarylene groups include linking groups that replace at least one carbon atom in the ring skeleton constituting the arylene with a nitrogen atom.

[0169] In the following, L is cited. 1 Specific examples. Among them, L can be used in this invention. 1 These specific examples are not intended to be limiting. Furthermore, in the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0170] [Chemical Formula 13]

[0171]

[0172] The invention discloses groups in which all hydrogen atoms present in L2 to L13 are replaced with deuterium atoms as L14 to L25. In one embodiment of the invention, L... 1 It is selected from the group consisting of L1 to L25. In one embodiment of the invention, L 1 It is selected from the group consisting of L1 to L7 and L14 to L19. In one embodiment of the invention, L 1 The group consisting of L1, L8-L13, and L20-L25 is selected. In one embodiment of the invention, L... 1 Choose from the groups consisting of L2 to L25.

[0173] X in general formula (2) 1 ~X 3 Let N or C(R) be represented independently, respectively. Where X... 1 ~X 3 At least one of them is N. R represents a hydrogen atom, a deuterium atom, or a substituent. The substituents described herein can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In a preferred embodiment of the invention, X 1 ~X 3 Let N be the number of elements. In one aspect of the invention, X... 1 and X 3 Let N, X 2 For C(R). In one aspect of the invention, X 1 and X 2 Let N, X 3 For C(R). In one aspect of the invention, X 1 Let N, X2 and X 3 For C(R). In one aspect of the invention, X 2 Let N, X 1 and X 3 R is C(R). In one embodiment of the invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the invention, R is an alkyl group that can be substituted with a deuterium atom. In one embodiment of the invention, R is an aryl group that can be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0174] Regarding Ar in general formula (2) 3 and Ar 4 For specific examples and preferred ranges, please refer to Ar in general formula (1). 1 and Ar 2 Corresponding explanation. In one aspect of the present invention, Ar 1 and Ar 3 Same. In a preferred embodiment of the invention, Ar 1 and Ar 3 Same, Ar 2 and Ar 4 Same. In one aspect of the invention, Ar 1 ~Ar 4 same.

[0175] In a preferred embodiment of the invention, X 1 ~X 3 For N, L 1 It is a single bond. In one embodiment of the invention, X 1 ~X 3 For N, L 1 The arylene group may be substituted or unsubstituted, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6).

[0176] In one aspect of the invention, X 1 ~X 3 For N, L 1 For a single bond, Ar 3 and Ar 4 Same. In one aspect of the invention, X 1 ~X 3 For N, L 1 For a single bond, Ar 3 and Ar 4 Each is independently either substituted or unsubstituted aryl group. In one aspect of the invention, X 1 ~X 3 For N, L 1 For a single bond, Ar 3 and Ar 4Each is independently a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably an electron-donating heteroaryl group bonded by a nitrogen atom, and more preferably a substituted or unsubstituted carbazole-9-yl group. In one aspect of the invention, X 1 ~X 3 For N, L 1 For a single bond, Ar 3 The heteroaryl group may be substituted or unsubstituted (excluding nitrogen-containing 6-membered ring groups), preferably an electron-donating heteroaryl group bonded by a nitrogen atom, more preferably a substituted or unsubstituted carbazole-9-yl group, Ar 4 The aryl group can be substituted or not.

[0177] In a preferred embodiment of the invention, only R 2 It is a group represented by general formula (2). In a preferred embodiment of the invention, only R 3 It is a group represented by general formula (2). In one aspect of the invention, only R 1 R 3 R 4 R 5 1 in and R 2 Each is an independent group represented by general formula (2). In one aspect of the invention, only R 1 R 2 R 4 R 5 1 in and R 3 Each is a group represented independently by the general formula (2).

[0178] The compound represented by general formula (1) is R. 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings, or Ar 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups), or R 1 ~R 5 and Ar 1 ~Ar 4 Both of these conditions must be met.

[0179] The "donor group having a fused ring structure of four or more rings" mentioned herein refers to a donor group having a fused ring structure of four or more rings and bonded to one atom of the ring skeleton constituting atoms of the fused ring structure. This one atom is preferably a carbon atom or a nitrogen atom, more preferably a nitrogen atom. The donor group mentioned herein refers to a group with a negative Hammett σp value.

[0180] Donor groups having a fused ring structure of 4 or more rings are preferably having a fused ring structure of 5 or more rings, and more preferably having a fused ring structure of 5 to 7 rings. For example, donor groups having a fused ring structure of 5 rings or donor groups having a fused ring structure of 7 rings can be cited.

[0181] As a donor group having a fused ring structure of four or more rings, cyclic fused carbazole-9-yl is preferred. Specific examples include D86 to D1210.

[0182] In particular, groups having the structure represented by the following general formula (3) are preferred.

[0183] [Chemical Formula 14]

[0184] General formula (3)

[0185]

[0186] In general formula (3), X represents O, S or NR. 14 R 11 ~R 13 Each can be used independently to represent a deuterium atom or a substituent. R 14 R represents an aryl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium, alkyl, and aryl, or an alkyl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium and aryl. 11 Each other, R 12 Each other, R 13 They can be bonded to each other to form a ring structure. n11 and n13 each represent any integer from 0 to 4, and n12 represents any integer from 0 to 2.

[0187] In general formula (3), X represents O, S or NR. 14 R 14 This refers to an aryl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups, or an alkyl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium atoms and aryl groups. The aryl group, as a substituent for the aryl or alkyl group, can be selected, for example, from aryl groups having 6 to 22 carbon atoms, and the alkyl group, as a substituent for the alkyl or 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 14It is an aryl group (e.g., 6 to 22 carbon atoms). The aryl group may be substituted by one or more atoms or groups selected from the group consisting of deuterium, alkyl (e.g., 1 to 20 carbon atoms), and aryl (e.g., 6 to 22 carbon atoms), or may be unsubstituted. X may be an oxygen atom or a sulfur atom.

[0188] In general formula (3), the two bonds involved in one benzene ring of the carbazole ring are bonded at adjacent positions on the benzene ring to form a fused ring structure of the carbazole ring and the heterofused ring containing X. For example, when X is O, a benzofuran carbazole ring is formed as a fused ring structure; when X is S, a benzothiophene carbazole ring is formed as a fused ring structure; and when X is NR... 14 In this case, an indolocarbazole ring is formed as a fused ring structure. The two bonds can be bonded at positions 1 and 2, 2 and 3, or 3 and 4 of the carbazole ring. When the two bonds are bonded at positions 1 and 2, the bond of X can be bonded at position 1 or 2; when the two bonds are bonded at positions 2 and 3, the bond of X can be bonded at position 2 or 3; and when the two bonds are bonded at positions 3 and 4, the bond of X can be bonded at position 3 or 4.

[0189] In general formula (3), * represents the bonding position.

[0190] In general formula (3), R 11 ~R 13 Each can be used independently to represent a deuterium atom or a substituent. R 11 Each other, R 12 Each other, R 13 They can bond to each other individually to form a ring structure, but R 11 Will not with R 12 ~R 14 Any one of them bonds with each other to form a ring structure, R 12 Will not with R 13 R 14 Any one of them bonds with each other to form a ring structure, R 13 Will not with R 14 They bond together to form a cyclic structure. Regarding substituents, for example, they can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In a preferred embodiment of the invention, the substituent represents a group obtained by combining one or more groups selected from the group consisting of alkyl (e.g., 1 to 20 carbon atoms) and aryl (e.g., 6 to 22 carbon atoms).

[0191] n11 and n13 independently represent any integer from 0 to 4, and n12 represents any integer from 0 to 2. When n11 is 2 or more, there are two or more R... 11 They can be the same or different. When n13 is 2 or more, there are 2 or more R... 13 They can be the same or different. When n12 is 2, there are 2 R... 12 They can be the same or different. n11 and n13 can be any number from 0, 1, 2, 3, 4, and n12 can be any number from 0, 1, 2. When n11 is 1, R 11 It can be a deuterium atom or a substituent. When n11 is 2 or higher, there can be 2 or more R atoms. 11 It can be entirely composed of deuterium atoms, entirely composed of substituents, or partially composed of deuterium atoms with the remainder being substituents. When n13 is 1, R 13 It can be a deuterium atom or a substituent. When n13 is 2 or more, there can be 2 or more R atoms. 13 It can be entirely composed of deuterium atoms, entirely composed of substituents, or partially composed of deuterium atoms with the remainder being substituents. When n12 is 1, R 12 It can be a deuterium atom or a substituent. When n12 is 2, there are 2 R atoms. 12 Both can be deuterium atoms, both can be substituents, or one of them can be a deuterium atom and the other a substituent.

[0192] When a donor group with a fused ring structure of 4 or more rings is present, R is preferred. 1 ~R 5 Two or more of them are donor groups with a fused ring structure of four or more rings, for example, two or three. In R 1 ~R 5 When two or more of the donor groups are fused ring structures with four or more rings, these groups may be the same or different, but are preferably the same. In one aspect of the invention, at least R 3 It is a donor group having a fused ring structure with four or more rings. In one embodiment of the invention, at least R 4 It is a donor group having a fused ring structure with four or more rings. In one embodiment of the invention, at least R 5 It is a donor group having a fused ring structure with four or more rings. In one embodiment of the invention, R 3 and R 5 It is a donor group having a fused ring structure with four or more rings. In one embodiment of the invention, R 3 and R 4 and R 5 It is a donor group with a fused ring structure of 4 or more rings.

[0193] In a preferred embodiment of the invention, Ar 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups). Substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups) can be only Ar. 1 ~Ar 4 One, two, three, or all of the elements may be present. When there are two or more, they may be the same or different, but are preferably the same. The substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups) is preferably a heteroaryl group bonded to a nitrogen atom that is one of the ring skeleton constituent atoms, preferably a heteroaryl group having a nitrogen-bonded 5-membered ring (a group bonded to a nitrogen atom of a pyrrole ring, which may be substituted, preferably a fused ring), and more preferably a substituted or unsubstituted carbazole-9-yl group. In a preferred embodiment of the invention, the carbazole-9-yl group described herein may be substituted by an alkyl or aryl group that may be substituted by a group selected from the group consisting of deuterium, alkyl, and aryl, or may be substituted by a deuterium atom. For a description and detailed information about the carbazole-9-yl group, please refer to R. 1 ~R 5 The following can be used: descriptions of carbazole-9-yl, descriptions of cyclic fused carbazole-9-yl, or specific examples D1 to D1210.

[0194] In a preferred embodiment of the invention, Ar 1 ~Ar 4 Each aryl group can be independently substituted or unsubstituted. Ar 1 ~Ar 4 They can all be the same; for example, unsubstituted phenyl and fully deuterated phenyl can be cited. In Ar 1 ~Ar 4 When R is independently a substituted or unsubstituted aryl group, 1 ~R 5 One or more of the donor groups are donor groups having a fused ring structure with four or more rings. The number of donor groups having a fused ring structure with four or more rings can be two or more, for example, two or three. Specific examples D86 to D1210 can be referred to as donor groups having a fused ring structure with four or more rings. Preferably, donor groups having a fused ring structure with five or more rings (e.g., five rings, for example, seven rings) can be used. In a preferred embodiment of the invention, in Ar... 1 ~Ar 4 When R is independently a substituted or unsubstituted aryl group, 1 ~R 5One or more of them have deuterium atoms. For example, it may have a deuterated donor group with a fused ring structure of 3 rings (e.g., perdeuterated carbazole-9-yl) or a deuterated aryl group (e.g., perdeuterated phenyl).

[0195] The compound represented by general formula (1) preferably does not contain metal atoms and can be a compound composed only of 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 general formula (1) is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Furthermore, the compound represented by general formula (1) can be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) can be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. Furthermore, the compound represented by general formula (1) can be a compound containing deuterium atoms but not hydrogen atoms.

[0196] In this specification, "substituent group A" represents a group selected from deuterium, hydroxyl, halogen (e.g., fluorine, chlorine, bromine, iodine), alkyl (e.g., 1-40 carbon atoms), alkoxy (e.g., 1-40 carbon atoms), alkylthio (e.g., 1-40 carbon atoms), aryl (e.g., 6-30 carbon atoms), aryloxy (e.g., 6-30 carbon atoms), arylthio (e.g., 6-30 carbon atoms), heteroaryl (e.g., 5-30 ring skeleton atoms), heteroaryloxy (e.g., 5-30 ring skeleton atoms). A group obtained by combining one or more atoms or groups from the group consisting of 5 to 30 atoms, heteroarylthio (e.g., 5 to 30 atoms constituting the ring skeleton), acyl (e.g., 1 to 40 carbon atoms), alkenyl (e.g., 1 to 40 carbon atoms), alkynyl (e.g., 1 to 40 carbon atoms), alkoxycarbonyl (e.g., 1 to 40 carbon atoms), aryloxycarbonyl (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl (e.g., 1 to 40 carbon atoms), silyl (e.g., trialkylsilyl with 1 to 40 carbon atoms), and nitro.

[0197] In this specification, "substituent group B" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., 1 to 40 carbon atoms), alkoxy (e.g., 1 to 40 carbon atoms), aryl (e.g., 6 to 30 carbon atoms), aryloxy (e.g., 6 to 30 carbon atoms), heteroaryl (e.g., 5 to 30 ring skeleton atoms), heteroaryloxy (e.g., 5 to 30 ring skeleton atoms), and diarylamino (e.g., 0 to 20 carbon atoms).

[0198] In this specification, "substituent group C" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms), heteroaryl (e.g., 5 to 20 cyclic skeleton atoms), and diarylamino (e.g., 12 to 20 carbon atoms).

[0199] In this specification, "substituent group D" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium atom, alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms) and heteroaryl (e.g., 5 to 20 cyclic skeleton atoms).

[0200] In this specification, "substituent group E" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., carbon atoms 1 to 20) and aryl (e.g., carbon atoms 6 to 22).

[0201] In this specification, the substituents described as "substituted or unsubstituted" or "substitutable" can be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0202] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 8 below. The compounds represented by general formula (1) that can be used in this invention should not be interpreted limitingly by these specific examples.

[0203] In Table 1, R is determined for each compound according to the following general formula (1a). 3 ~R 5 The structures of each compound are shown individually. Specifically, the following structures are shown individually as the structures of compounds 1 through 170: R 2 For the group represented by general formula (2), Ar 1 and Ar 3 It is a fully deuterated carbazole-9-yl (D55), Ar2 and Ar 4 It is a fully deuterated phenyl group (Ar47), X 1 ~X 3 For nitrogen atoms (N), L 1 For a single bond (L1), R 1 For hydrogen atoms, R 3 ~R 5 These are the groups identified in Table 1.

[0204] [Chemical Formula 15]

[0205] General formula (1a)

[0206]

[0207] [Table 1]

[0208]

[0209] Table 2 shows the R values ​​of multiple compounds by summarizing them in each section. 3 ~R 5 To illustrate the structures of compounds 1 through 442987. For example, if it is the section of compounds 1 through 85 in Table 2, then R... 4 Fixed as D1 (carbazole-9-yl), R 3 and R 5 Compounds with the same D1 to D85 are designated as compounds 1 to 85 respectively. Furthermore, if the compounds fall within the range of compounds 86 to 170 in Table 2, then R... 4 Fixed as D2(3-methylcarbazole-9-yl), R 3 and R 5 Compounds that are identical and have the digits D1 to D85 are designated as compounds 86 to 170, respectively. That is, compounds 1 to 170 identified in Table 1 are summarized in two sections, namely, the section for compounds 1 to 85 and the section for compounds 86 to 170 in Table 2. Similarly, for the section for compounds 171 to 255 in Table 2, R... 4 Fixed as D3(3,6-dimethylcarbazole-9-yl), R 3 and R 5 Compounds with the same D1 to D85 were designated as compounds 171 to 255, respectively. Following the same principle, compounds 256 to 442987 in Table 2 were also identified.

[0210] [Table 2]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] Next, specific examples of compounds having the structure represented by the following general formula (1b) are shown in Table 3. In Table 3, the structures of each compound are shown according to the same principle as in Table 2.

[0220] [Chemical Formula 16]

[0221] General formula (1b)

[0222]

[0223] [Table 3]

[0224]

[0225]

[0226] Next, specific examples of compounds having the structure represented by the following general formula (1c) are shown in Table 4. In Table 4, the structures of each compound are shown according to the same principle as in Table 2.

[0227] [Chemical Formula 17]

[0228] General formula (1c)

[0229]

[0230] [Table 4]

[0231]

[0232]

[0233] Next, specific examples of compounds having the structure represented by the following general formula (1d) are shown in Table 5. In Table 5, the structures of each compound are shown according to the same principle as in Table 2.

[0234] [Chemical Formula 18]

[0235] General formula (1d)

[0236]

[0237] [Table 5]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] Next, specific examples of compounds having the structure represented by the following general formula (1e) are shown in Table 6. In Table 6, the structures of each compound are shown according to the same principle as in Table 2.

[0246] [Chemical Formula 19]

[0247] General formula (1e)

[0248]

[0249] [Table 6]

[0250]

[0251]

[0252] Next, specific examples of compounds having the structure represented by the following general formula (1f) are shown in Table 7. In Table 7, the structures of each compound are shown according to the same principle as in Table 2.

[0253] [Chemical Formula 20]

[0254] General formula (1f)

[0255]

[0256] [Table 7]

[0257]

[0258]

[0259] In Tables 1 to 4, determine the Ar of general formula (1). 1 and Ar 3 It is a fully deuterated carbazole-9-yl (D55) and Ar 2 and Ar 4The structure of the fully deuterated phenyl group (Ar47) is used as the structure of compounds 1–636657. In Tables 5–7, the Ar47 of general formula (1) is determined. 1 ~Ar 4 The structure of the fully deuterated phenyl (Ar47) is shown in compounds 636658–1257639.

[0260] In Table 8 below, along with compounds 636658 to 1257639, for all or part of compounds 1 to 636657, Ar was modified as shown in Table 8. 1 ~Ar 4 The compounds are listed in a table. In Table 8, to facilitate understanding of the correspondence, compounds 1 to 636657 are shown in the first paragraph, and compounds 636658 to 1257639 are shown in the second paragraph. In the third paragraph of Table 8, the Ar values ​​of compounds 1 to 636657 are listed. 1 and Ar 3 The compounds, all of which are D1, are designated as compounds 1(1) to 636657(1). For example, compound 1(1) represents the compound with Ar... 1 and Ar 3 Compounds with the structure of D1 replaced by D1. Furthermore, compound 2(1) represents compounds having the Ar... 1 and Ar 3 Compounds with the structure replaced by D1. Compound 636657(1) represents compounds having the Ar structure of compound 636657. 1 and Ar 3 Compounds with the structure replaced by D1. In paragraph 4 of Table 8, the Ar atoms of compounds 1–636657 are listed. 1 and Ar 3 Compounds with D7 were designated as compounds 1(2) to 636657(2) in sequence. Following this principle, the Ar values ​​of compounds 1 to 636657 were determined sequentially. 1 and Ar 3 Ar 2 and Ar 4 Compounds containing the groups listed in Table 8. Additionally, the X of the compounds identified in Table 8... 1 ~X 3 All are nitrogen atoms (N), L 1 For a single bond (L1), R 1 It is a hydrogen atom. Ar 1 and Ar 3 Same, Ar 2 and Ar 4 same.

[0261] [Table 8]

[0262]

[0263]

[0264]

[0265]

[0266] Compounds 1 to 636657 (371) listed in Table 8 are R in general formula (1). 1 Compounds containing hydrogen atoms. The R of these compounds will be... 1 Compounds with structures substituted with deuterium atoms are designated as compounds 1d to 636657(371)d, respectively. Furthermore, compounds possessing the R... 1 The compounds with the structure of a fully deuterated phenyl (Ar47) were designated as compounds 1D to 636657(371)D.

[0267] In Tables 1 to 8, compounds identified by numbers, compounds 1d to 636657(371)d, and compounds 1D to 636657(371)D are disclosed individually. In addition, in cases where rotational isomers exist in the specific examples of the above compounds, mixtures of rotational isomers and isolated rotational isomers are also disclosed in this specification.

[0268] In one aspect of the invention, compounds are selected from the group of compounds identified in Table 8.

[0269] Give an example of the preferred group of compounds represented by general formula (1).

[0270] [Chemical Formula 21]

[0271]

[0272]

[0273] Give an example of another preferred group of compounds represented by general formula (1).

[0274] [Chemical Formula 22]

[0275]

[0276]

[0277] Give an example of another preferred group of compounds represented by general formula (1).

[0278] [Chemical Formula 23]

[0279]

[0280] Give an example of another preferred group of compounds represented by general formula (1).

[0281] [Chemical Formula 24]

[0282]

[0283] Give an example of another preferred group of compounds represented by general formula (1).

[0284] [Chemical Formula 25]

[0285]

[0286] Give an example of another preferred group of compounds represented by general formula (1).

[0287] [Chemical Formula 26]

[0288]

[0289]

[0290] Give an example of another preferred group of compounds represented by general formula (1).

[0291] [Chemical Formula 27]

[0292]

[0293]

[0294] Give an example of another preferred group of compounds represented by general formula (1).

[0295] [Chemical Formula 28]

[0296]

[0297]

[0298] Give an example of another preferred group of compounds represented by general formula (1).

[0299] [Chemical Formula 29]

[0300]

[0301] Give an example of another preferred group of compounds represented by general formula (1).

[0302] [Chemical Formula 30]

[0303]

[0304] Give an example of another preferred group of compounds represented by general formula (1).

[0305] [Chemical Formula 31]

[0306]

[0307]

[0308]

[0309] Regarding the molecular weight of the compound represented by general formula (1), for example, when attempting to form an organic layer containing the compound represented by general formula (1) by vapor deposition, it is preferably 1500 or less, more preferably 1200 or less, further 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).

[0310] Compounds represented by general formula (1) can be coated to form films regardless of molecular weight. Even compounds with relatively large molecular weights can be coated to form films. Compounds represented by general formula (1) have advantages such as easy solubility in organic solvents. Therefore, compounds represented by general formula (1) are readily applicable to coating and easy to purify to improve purity.

[0311] By applying this invention, compounds containing multiple structures represented by general formula (1) within the molecule can also be considered as luminescent materials.

[0312] For example, it is possible to pre-contain polymeric groups in the structure represented by general formula (1) and use the polymer obtained by polymerizing these polymeric groups as a luminescent material. For example, it is possible to prepare monomers containing polymeric functional groups at any site in general formula (1), obtain polymers with repeating units by polymerizing them alone or copolymerizing them with other monomers, and use these polymers as luminescent materials. Alternatively, it is possible to obtain dimers or trimers by coupling compounds having the structure represented by general formula (1) with each other and use these as luminescent materials.

[0313] As an example of a polymer having repeating units containing the structure represented by general formula (1), a polymer containing the structure represented by either of the following two general formulas can be cited.

[0314] [Chemical Formula 32]

[0315]

[0316] In the above general formula, Q represents a group containing the structure represented by general formula (1), and L 1 and L2 This indicates a linking group. The linking group preferably has 0 to 20 carbon atoms, more preferably 1 to 15, and even more preferably 2 to 10. The linking group preferably has a -X symbol. 11 -L 11 - The linking group representing the structure. Here, X 11 Represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11 The linking group is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms.

[0317] In the above general formula, R 101 R 102 R 103 and R 104 Each substituent is represented independently. Preferably, it is a substituted or unsubstituted alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 6 carbon atoms, or a halogen atom; more preferably, it is an unsubstituted alkyl group with 1 to 3 carbon atoms, an unsubstituted alkoxy group with 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, it is an unsubstituted alkyl group with 1 to 3 carbon atoms or an unsubstituted alkoxy group with 1 to 3 carbon atoms.

[0318] L 1 and L 2 The linking group can be bonded to any site in the general formula (1) constituting Q. Two or more linking groups can be linked to one Q to form a cross-linked structure or a network structure.

[0319] As a specific example of a repeating unit, the structure represented by the following formula can be cited.

[0320] [Chemical Formula 33]

[0321]

[0322] Polymers having repeating units containing these formulas can be synthesized as follows: a hydroxyl group is introduced into any site of general formula (1), which is used as a linking group to react the following compound to introduce a polymerizable group, and the polymerizable group is polymerized.

[0323] [Chemical Formula 34]

[0324]

[0325] Polymers containing the structure represented by general formula (1) within their molecules can be polymers composed solely of repeating units having the structure represented by general formula (1), or polymers containing repeating units having structures other than those represented by general formula (1). Furthermore, the repeating unit containing the structure represented by general formula (1) in the polymer can be a single type or two or more types. As repeating units that do not have the structure represented by general formula (1), examples include repeating units derived from monomers used in conventional copolymerization. For example, repeating units derived from monomers such as ethylene and styrene that have olefinic unsaturated bonds can be cited.

[0326] For information on the use of the compound represented by general formula (1), please refer to WO2022 / 168956A1,

[0058] to

[0059] ,

[0061] and

[0063] , which are incorporated herein by reference as part of this specification.

[0327] [Synthetic methods for compounds represented by general formula (1)]

[0328] The compounds represented by general formula (1) include novel compounds.

[0329] The compounds represented by general formula (1) can be synthesized by combining known reactions. Regarding the compounds represented by general formula (1), R... 1 ~R 5 Two or more of the groups are donor groups. For example, compounds of general formula (1) with substituted or unsubstituted carbazole-9-yl as donor groups can be synthesized by reacting a substituted or unsubstituted carbazole with a precursor in which the donor group is a fluorine atom. For details on the reaction conditions, please refer to the synthesis examples described later.

[0330] Organic light-emitting elements

[0331] The organic light-emitting element of the present invention comprises a compound represented by general formula (1) and a host material or dopant material in the same layer. The same layer is preferably a light-emitting layer. In one aspect of the invention, a compound represented by general formula (1) and a host material are comprised in the same layer. The host material is preferably used at a higher concentration than the compound represented by general formula (1), and the minimum excitation singlet energy is higher than that of the compound represented by general formula (1). In another aspect of the invention, a compound represented by general formula (1) and a dopant material are comprised in the same layer. The dopant material is preferably used at a lower concentration than the compound represented by general formula (1), and the minimum excitation singlet energy is lower than that of the compound represented by general formula (1).

[0332] In one embodiment, the compound represented by general formula (1) is suitable for phosphorescence-sensitized fluorescence.

[0333] In one embodiment, the compound represented by general formula (1) functions as a luminescent material in the organic light-emitting element. In another embodiment, the compound represented by general formula (1) functions as a luminescent material that emits delayed fluorescence in the organic light-emitting element.

[0334] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it can emit light in the UV region, the blue, green, yellow, orange, or red regions 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.

[0335] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it is able to emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm).

[0336] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it is able to 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).

[0337] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it is able to emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm).

[0338] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it is able to emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm).

[0339] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it can emit light in the ultraviolet spectral region (e.g., 280–400 nm).

[0340] In one embodiment of this disclosure, when the compound represented by general formula (1) is excited by a thermal or electronic device, it can emit light in the infrared spectral region (e.g., 780 nm to 2 μm).

[0341] When forming the layers of organic light-emitting elements, film-forming techniques can be utilized.

[0342] In one embodiment, a film comprising a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution obtained by dissolving a composition comprising the compound of the present invention is applied to a surface, and after removing the solvent, a film is formed. Examples of wet processes include spin coating, slot coating, inkjet printing, gravure printing, offset printing, and flexographic printing, but are not limited to these. In the wet process, a suitable organic solvent capable of dissolving the composition comprising the compound of the present invention is selected. In one embodiment, a substituent (e.g., an alkyl group) that improves solubility with respect to an organic solvent can be introduced into the compound comprising the composition.

[0343] In one embodiment, a film containing the compound of the present invention can be formed in a dry process. In one embodiment, vacuum evaporation can be used as the dry process, but it is not limited to this. When using vacuum evaporation, the compound constituting the film can be co-deposited from a single evaporation source, or from a single evaporation source containing a mixture of compounds. When using a single evaporation source, a mixed powder obtained by mixing compound powders can be used, a compression molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating, melting, and cooling the compounds can be used. In one embodiment, by performing co-evaporation under conditions where the evaporation rates (weight reduction rates) of the multiple compounds contained in a single evaporation source are consistent or substantially consistent, a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the evaporation source can be formed. If multiple compounds are mixed with the same composition ratio as the composition ratio of the formed film and used as the evaporation source, a film with the desired composition ratio can be easily formed. In one embodiment, the temperature at which the co-deposited compounds achieve the same weight reduction rate can be determined, and this temperature is used as the temperature for co-evaporation.

[0344] In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In another embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by general formula (1) assists in the luminescence of other light-emitting materials contained in the light-emitting layer (as a so-called auxiliary dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet state energy level, which is contained between the lowest excited singlet state energy level of the host material contained in the light-emitting layer and the lowest excited singlet state energy level of another light-emitting material contained in the light-emitting layer.

[0345] In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least one light-emitting layer. In one embodiment, the organic layer includes only one light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers, and exciton blocking layers. In one embodiment, the hole transport layer can be a hole injection and transport layer with hole injection function, and the electron transport layer can be an electron injection and transport layer with electron injection function.

[0346] Emissive layer:

[0347] In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, rebond to form excitons. In one embodiment, the layer emits light.

[0348] In one embodiment, the light-emitting layer comprises a light-emitting material as a dopant and a host material. In one embodiment, the light-emitting material is a compound represented by general formula (1). In one embodiment, to improve the luminous efficiency of organic electroluminescent elements and organic photoluminescent elements, singlet and triplet excitons generated in the light-emitting material are confined within the light-emitting material. In one embodiment, a host material is used in addition to the light-emitting material in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excitation singlet state energy and an excitation triplet state energy, at least one of which is higher than those energies of the light-emitting material of the present invention. In one embodiment, singlet and triplet excitons generated in the light-emitting material of the present invention are confined within the molecules of the light-emitting material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently confined to promote luminous efficiency. In one embodiment, the singlet and triplet excitons are not sufficiently confined, but a high luminous efficiency is still obtained; that is, a host material capable of achieving a high luminous efficiency can be used in the present invention without particular limitation. In one embodiment, luminescence occurs in the luminescent material within the luminescent layer of the element of the present invention. In one embodiment, the emitted light comprises both fluorescence and delayed fluorescence. In one embodiment, the emitted light comprises light emitted from the host material. In one embodiment, the emitted light consists of light emitted from the host material. In one embodiment, the emitted light comprises light emitted from the compound represented by general formula (1) and light emitted from the host material. In one embodiment, TADF molecules and the host material are used. In one embodiment, TADF is an auxiliary dopant that excites a singlet state energy lower than that of the host material in the luminescent layer and an excitation singlet state energy higher than that of the luminescent material in the luminescent layer.

[0349] (Doped materials)

[0350] When the compound represented by general formula (1) is used as the host material or auxiliary dopant, various compounds can be used as luminescent materials (preferably fluorescent materials) as dopants. Anthracene derivatives, TetracenE derivatives, NaphthacenE derivatives, pyrene derivatives, perylene derivatives, etc., can be used as such luminescent materials. Derivatives, including rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthracene derivatives, pyrrole methylene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, juulolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn), etc. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons can be combined with each other.

[0351] Hereinafter, examples are given of doped materials (luminescent materials) that can be used in combination with compounds represented by general formula (1).

[0352] [Chemical Formula 35]

[0353]

[0354]

[0355]

[0356] In addition to the above, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 may also be used as luminescent materials in conjunction with auxiliary dopants having the structure represented by general formula (1).

[0357] As a dopant material (luminescent material) that can be used in combination with the compound represented by general formula (1), the compound represented by the following general formula (4) is particularly preferred.

[0358] [Chemical Formula 36]

[0359] General formula (4)

[0360]

[0361] In general formula (4), X 1 and X 2One of them is a nitrogen atom and the other is a boron atom. In one aspect of the invention, X 1 X is a nitrogen atom. 2 It consists of boron atoms. At this point, R... 17 and R 18 They bond together to form single bonds to form a pyrrole ring. In another aspect of the invention, X 1 For boron atoms, X 2 It is a nitrogen atom. At this point, R... 21 and R 22 They bond together to form single bonds, thus forming a pyrrole ring.

[0362] In general formula (4), R 1 ~R 26 A 1 A 2 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent.

[0363] R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 7 and R 8 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 17 and R 18 R 18 and R 19 R 19 and R 20 R 20 and R 21 R 21 and R 22 R 22 and R 23 R 23 and R24 R 24 and R 25 R 25 and R 26 They can bond together to form a ring structure.

[0364] R 7 and R 8 The bonded ring structure contains boron atoms and four carbon atoms as the ring framework. In X 1 When R is a boron atom, 17 and R 18 The bonded ring structure contains boron atoms and four carbon atoms as the ring framework. In X 1 When the atom is nitrogen, the cyclic structure is confined to a pyrrole ring. In X... 2 When R is a boron atom, 21 and R 22 The bonded ring structure contains boron atoms and four carbon atoms as the ring framework. In X 2 When the atom is nitrogen, the cyclic structure is confined to a pyrrole ring. In R... 7 and R 8 R 17 and R 18 R 21 and R 22 When the rings bond together to form a ring structure containing boron atoms, the ring structure is preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring. In R 7 and R 8 R 17 and R 18 R 21 and R 22 When bonds are formed, they are preferably bonded together to form single bonds, -O-, -S-, or -N(R) bonds. 27 )-、-C(R 28 (R) 29 )-、-Si(R 30 (R) 31 )-、-B(R 32 -, -CO-, -CS-, more preferably -O-, -S- or -N(R) 27 )-, further optimized to form -N(R 27 )-. Among them, R 27 ~R 32 Each of the following can be independently represented: a hydrogen atom, a deuterium atom, or a substituent. As a substituent, any group selected from substituent group A to E can be used, but substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups are preferred, and R is particularly preferred. 27 The aryl group can be substituted or unsubstituted. In R27 ~R 32 When it is a substituent, R 7 and R 8 R in the ring formed by mutual bonding 27 ~R 32 Can be used with R 6 and R 9 At least one of them bonds to further form a ring structure, R 17 and R 18 R in the ring formed by mutual bonding 27 ~R 32 Can be used with R 16 and R 19 At least one of them bonds to further form a ring structure, R 21 and R 22 R in the ring formed by mutual bonding 27 ~R 32 Can be used with R 20 and R 23 At least one of them is bonded to further form a ring structure. In one aspect of the invention, R 7 and R 8 R 17 and R 18 R 21 and R 22 Only one group in each is bonded to the other. In one aspect of the invention, R 7 and R 8 R 17 and R 18 R 21 and R 22 Only two groups are bonded to each other. In one aspect of the invention, R 7 and R 8 R 17 and R 18 R 21 and R 22 All of them are linked together.

[0365] R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 8 and R 9 R 9 and R 10 R 10 and R11 R 11 and R 12 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 18 and R 19 R 19 and R 20 R 20 and R 21 R 22 and R 23 R 23 and R 24 R 24 and R 25 R 25 and R 26 The cyclic structure formed by the bonding of rings can be an aromatic ring or an aliphatic ring, and can contain heteroatoms. Other rings can be further fused together with one or more rings. The heteroatoms described herein are preferably selected from the group consisting of nitrogen, oxygen, and sulfur atoms. Examples of the formed cyclic structures include benzene rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, pyrrole rings, imidazole rings, pyrazole rings, triazole rings, imidazoline rings, furan rings, thiophene rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, cyclohexadiene rings, cyclohexene rings, cyclopentene rings, cycloheptanetriene rings, cycloheptadiene rings, cycloheptene rings, and rings formed by further fusion of one or more rings selected from the group consisting of these rings. In a preferred embodiment of the invention, the cyclic structure is a substituted or unsubstituted benzene ring (and may also contain fused rings), for example, a benzene ring that can be substituted with alkyl or aryl groups. In a preferred embodiment of the invention, the cyclic structure is a substituted or unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran or a thiophene ring of benzothiophene. 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R12 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 18 and R 19 R 19 and R 20 R 20 and R 21 R 22 and R 23 R 23 and R 24 R 24 and R 25 R 25 and R 26 The number of combinations of elements bonded together to form a ring structure can be 0, for example, it can be any one of 1 to 6. For example, it can be any one of 1 to 4, and can be selected as 1, 2, 3, or 4. In one aspect of the invention, from R... 1 and R 2 R 2 and R 3 R 3 and R 4 One group selected from the group bonds together to form a ring structure. In one aspect of the invention, R 5 and R 6 They bond together to form a ring structure. In one aspect of the invention, from R... 9 and R 10 R 10 and R 11 R 11 and R 12 One group selected from the group bonds together to form a ring structure. In one aspect of the invention, R 1 and R 2 R 13 and R 14 Any one of them bonds to each other to form a ring structure. In one aspect of the invention, from R 1 and R 2 R 2 and R 3 R 3 and R 4 One group selected from the group bonds to each other to form a ring structure, and R 5 and R 6 They bond together to form a ring structure. In one aspect of the invention, R 5 and R 6 R 19and R 20 Any one of them bonds with each other to form a ring structure.

[0366] Not adjacent to R n (n = 1 ~ 26) mutually bonded R 1 ~R 26 It can be a hydrogen atom, a deuterium atom, or a substituent. As a substituent, any group selected from substituent group A to E can be used.

[0367] R 1 ~R 26 Preferred substituents may be substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups. For example, the substituent may be a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. The alkyl, aryl, and heteroaryl substituents described herein may also be groups selected from any of the substituent groups A to E, but are preferably selected from one or more groups composed of alkyl, aryl, and heteroaryl groups, more preferably groups from substituent group E, and may also be unsubstituted. In a preferred embodiment of the invention, R... 1 ~R 6 At least one of them is a substituent, preferably a group of substituent group E. For example, R 2 ~R 6 At least one of them is a substituent, preferably a group of substituent group E. For example, R 5 and R 6 At least one of them is a substituent, preferably a group of substituent group E. In a preferred embodiment of the invention, R 3 and R 6 At least one of them is a substituent, more preferably both are substituents, and preferably a group of substituent group E. In a preferred embodiment of the invention, in X 1 When R is a nitrogen atom, 15 and R 20 At least one of them is a substituent, more preferably both are substituents, and preferably a group of substituent group E. In this case, R 17 and R 18 They bond together to form single bonds. In a preferred embodiment of the invention, in X... 2 When R is a nitrogen atom, 19 and R 24 At least one of them is a substituent, more preferably both are substituents, and preferably a group of substituent group E. In this case, R 21 and R 22 They bond together to form single bonds. In one aspect of the invention, R 8 and R 12At least one of them is a substituent, preferably both are substituents. In one aspect of the invention, R 8 R 10 and R 12 For substituents. As R 8 ~R 12 The substituents are preferably unsubstituted alkyl groups. In particular, in R... 8 and R 12 When the alkyl group has two or more carbon atoms (preferably an alkyl group with three or more carbon atoms, more preferably an alkyl group with three to eight carbon atoms, and even more preferably an alkyl group with three or four carbon atoms), the orientation becomes higher when the film is formed, which is therefore preferred. Among them, R is particularly preferred. 8 and R 12 The substituent (preferably alkyl, more preferably alkyl with 2 or more carbon atoms, even more preferably alkyl with 3 or more carbon atoms, even more preferably alkyl with 3 to 8 carbon atoms, particularly preferably alkyl with 3 or 4 carbon atoms) and R 1 ~R 6 In the case where at least one of them is a substituent (preferably a group of substituent group E). In X 1 When R is a boron atom, 13 and R 17 At least one of them is a substituent, preferably both are substituents. In one aspect of the invention, in X 1 When R is a boron atom, 13 R 15 and R 17 For substituents. In X 1 When it is a boron atom, it acts as R 13 ~R 17 The substituents are preferably unsubstituted alkyl groups. In X 2 When R is a boron atom, 22 and R 26 At least one of them is a substituent, preferably both are substituents. In one aspect of the invention, in X 2 When R is a boron atom, 22 R 24 and R 26 For substituents. In X 2 When it is a boron atom, it acts as R 22 ~R 26 The substituents are preferably unsubstituted alkyl groups. Examples of substituents are given below, which are represented by boron atoms (B) or X in general formula (4). 1 or X 2 Specific examples of boron-bonded groups are shown. However, the boron-bonded groups that can be used in this invention are not limited to the following specific examples. Furthermore, in this specification, the CH3 designation is omitted for methyl groups. * indicates the bonding position.

[0368] [Chemical Formula 37]

[0369]

[0370] In the following, R of general formula (4) is given. 1 ~R 26 A specific example. As R 1 ~R 7 X 1 R when it is a nitrogen atom 13 ~R 21 X 2 R when it is a nitrogen atom 18 ~R 26 Preferably, Y1 to Y9 are used as R. 8 ~R 12 X 1 R when it is a nitrogen atom 22 ~R 26 X 2 R when it is a nitrogen atom 13 ~R 17 Preferably, the groups bonded to boron atoms are Y1 to Y7. The specific examples below do not limit the use of these groups in this invention. D represents a deuterium atom. * indicates a bonding position.

[0371] [Chemical Formula 38]

[0372]

[0373] A 1 and A 2 It can be a hydrogen atom, a deuterium atom, or a substituent. As a substituent, any group selected from substituent group A to E can be used.

[0374] In a preferred embodiment of the present invention, A 1 and A 2 Each can be independently a hydrogen atom or a deuterium atom. For example, A 1 and A 2 It is a hydrogen atom. For example, A 1 and A 2 It is a deuterium atom.

[0375] A 1 and A 2 One of them can be a substituent. And, A 1 and A 2 They can be substituents independently. A 1 and A 2 The preferred substituent can be an acceptor group. The acceptor group is a group with a positive σp value in Hammett.

[0376] A 1 and A2 The acceptor group that can be used is more preferably a group with a Hammett σp value greater than 0.2. Examples of groups with a Hammett σp value greater than 0.2 include cyano, aryl groups at least substituted with cyano, groups containing a fluorine atom, and substituted or unsubstituted heteroaryl groups containing a nitrogen atom as a ring skeleton atom. The aryl group at least substituted with cyano described herein can be substituted with a substituent other than cyano (e.g., alkyl or aryl), but can also be an aryl group substituted only with cyano. The aryl group at least substituted with cyano is preferably a phenyl group at least substituted with cyano. The number of substitutions of the cyano group is preferably one or two, for example, one or two. Examples of groups containing a fluorine atom include fluorine, fluorinated alkyl, and aryl groups at least substituted with a fluorine atom or fluorinated alkyl. The fluorinated alkyl is preferably a perfluoroalkyl, and the number of carbon atoms is preferably 1 to 6, more preferably 1 to 3. Furthermore, the heteroaryl group containing a nitrogen atom as a ring skeleton atom can be a monocyclic ring or a fused ring formed by the fusion of two or more rings. In the case of a fused ring, the number of rings after fusion is preferably 2 to 6, for example, it can be selected from 2 to 4 or set to 2. Specific examples of the ring constituting the heteroaryl group include pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, quinoline rings, isoquinoline rings, quinazoline rings, quinoxaline rings, and naphthidine rings other than quinazoline and quinoxaline rings. The ring constituting the heteroaryl group can be substituted with a deuterium atom or a substituent. Examples of substituents include groups formed by one or more groups selected from the group consisting of alkyl, aryl, and heteroaryl groups. As A 1 and A 2 The acceptor group that can be used is preferably a cyano group.

[0377] In one aspect of the invention, A 1 and A 2 At least one of them is a receptor group. In one aspect of the invention, A 1 and A 2 Only one of them is an acceptor group. In one aspect of the invention, A 1 and A 2 Both of these are the same receptor group. In one aspect of the invention, A 1 and A 2 These are receptor groups that are different from each other. In one aspect of the invention, A 1 and A 2 It is a cyano group. In one aspect of the invention, A 1 and A 2 It is a halogen atom, such as a bromine atom.

[0378] The following shows specific examples of acceptor groups that can be used in this invention. However, the acceptor groups that can be used in this invention are not to be interpreted as limiting by the following specific examples. In this specification, the methyl group is omitted from the CH3 designation. Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups. Furthermore, "D" indicates a deuterium atom. * indicates a bonding position.

[0379] [Chemical Formula 39]

[0380]

[0381]

[0382] Additionally, in X 1 For nitrogen atoms, R 7 and R 8 A six-membered ring is formed through nitrogen atom bonding, R 21 and R 22 A six-membered ring is formed through nitrogen atom bonding, R 17 and R 18 When they bond together to form a single bond, R 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 Any one of them can bond with each other to form an aromatic ring (a fused substituted or unsubstituted benzene ring) or a heteroaromatic ring (preferably a fused substituted or unsubstituted furan ring of benzofuran or a fused substituted or unsubstituted thiophene ring of benzothiophene).

[0383] And, in X 1 For boron atoms, X 2 For nitrogen atoms, R 7 and R 8 R 17 and R 18 When they bond together to form a ring structure containing boron atoms, this ring structure is a 5- to 7-membered ring. In the case of a 6-membered ring, R 7 and R 8 R 17 and R 18 They bond together to form -B(R) 32 -, -CO-, -CS- or -N(R) 27 )-. R 27Preferably, it represents a hydrogen atom, a deuterium atom, or a substituent.

[0384] For details and specific examples of compounds represented by general formula (4), please refer to WO2022 / 270354A1,

[0019] to

[0128] , which are incorporated herein by reference as part of this specification.

[0385] In one embodiment, the luminescent layer comprises two or more TADF molecules with different structures. For example, it can be configured as a luminescent layer comprising three materials whose excited singlet state energy levels increase in the order of the host material, the first TADF molecule, and the second TADF molecule. In this case, the difference ΔE between the lowest excited singlet state energy level of the first TADF molecule and the second TADF molecule and the lowest excited triplet state energy level at 77K is... STThe concentrations are 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. Furthermore, 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 can be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the light-emitting layer can be set as follows: the host material is set to 10-70% by weight, the first TADF molecule is set to 10-80% by weight, and the second TADF molecule is set to 0.1-30% by weight. In one embodiment, the composition within the light-emitting layer can be set as follows: the host material is set to 20-45% by weight, the first TADF molecule is set to 50-75% by weight, and the second TADF molecule is set to 5-20% by weight. In one embodiment, the light emission quantum yield φPL1(A) induced by photoexcitation of the co-evaporated film of the first TADF molecule and the host material (the concentration of the first TADF molecule in the co-evaporated film = A% by weight) and the light emission quantum yield φPL2(A) induced by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-evaporated film = A% by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photoluminescence quantum yield φPL2(B) induced by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-evaporated film = B wt%) satisfies the relationship φPL2(B) > φPL2(100) induced by photoexcitation of a single film of the second TADF molecule. In one embodiment, the light-emitting layer can contain three TADF molecules with different structures. The compound of the present invention can be any one of a plurality of TADF compounds contained in the light-emitting layer.

[0386] In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an auxiliary dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain any metallic elements. In one embodiment, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0387] When the luminescent layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescence material. Preferred delayed fluorescence materials include segments 0008-0048 and 0095-0133 of WO2013 / 154064, segments 0007-0047 and 0073-0085 of WO2013 / 011954, segments 0007-0033 and 0059-0066 of WO2013 / 011955, and segments 0008-007 of WO2013 / 081088. Paragraphs 1 and 0118–0133, paragraphs 0009–0046 and 0093–0134 of Japanese Patent Application Publication No. 2013-256490, paragraphs 0008–0020 and 0038–0040 of Japanese Patent Application Publication No. 2013-116975, paragraphs 0007–0032 and 0079–0084 of Japanese Patent Application Publication No. WO2013 / 133359, and paragraph 0008 of Japanese Patent Application Publication No. WO2013 / 161437. Paragraphs 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of Japanese Patent Application Publication No. 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of Japanese Patent Application Publication No. 2014-9224, paragraphs 0013 to 0025 of Japanese Patent Application Publication No. 2017-119663, and paragraphs 0013 to 0026 of Japanese Patent Application Publication No. 2017-119664. Compounds contained in the general formula described in Japanese Patent Application Publication No. 2017-222623 (paragraphs 0012-0025), Japanese Patent Application Publication No. 2017-226838 (paragraphs 0010-0050), Japanese Patent Application Publication No. 2018-100411 (paragraphs 0012-0043), and Japanese Patent Application Publication No. WO2018 / 047853 (paragraphs 0016-0044), especially exemplary compounds, and compounds capable of emitting delayed fluorescence.Furthermore, among these, Japanese Patent Application Publication Nos. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, and WO Published in WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO20 The luminescent materials described in Japanese Publication No. 15 / 080183, Japanese Patent Application Publication No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541 are compounds capable of emitting delayed fluorescence. Furthermore, the aforementioned publications described in this paragraph are incorporated herein by reference as part of this specification.

[0388] (Main material)

[0389] When the compound represented by general formula (1) is used together with the host material, the amount of the compound represented by general formula (1) is 0.1% by weight or more. In one embodiment, when using the host material, the amount of the compound represented by general formula (1) as a luminescent material contained in the luminescent layer is 1% by weight or more. In one embodiment, when using the host material, the amount of the compound represented by general formula (1) as a luminescent material contained in the luminescent layer is 50% by weight or less. In one embodiment, when using the host material, the amount of the compound represented by general formula (1) as a luminescent material contained in the luminescent layer is 20% by weight or less. In one embodiment, when using the host material, the amount of the compound represented by general formula (1) as a luminescent material contained in the luminescent layer is 10% by weight or less.

[0390] In one embodiment, the host material in the light-emitting layer is an organic compound that incorporates both hole transport and electron transport functions. In another embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of the emitted light. In yet another embodiment, the host material in the light-emitting layer is an organic compound with a high glass transition temperature.

[0391] In some implementations, the body material is selected from the group consisting of:

[0392] [Chemical Formula 40]

[0393]

[0394]

[0395] In a preferred embodiment of the invention, the host material used together with the compound represented by general formula (1) is a compound having the structure represented by the following general formula (5).

[0396] [Chemical Formula 41]

[0397] General formula (5)

[0398]

[0399] In general formula (5), X 11 Represents O, S, N(R) A ) or C(R B (R) C In one aspect of the invention, X 11 For O, S or N(R) A In one aspect of the invention, X 11 It is either O or S. In one aspect of the invention, X is... 11 For N(R) A In one aspect of the invention, X 11 It is O. In one aspect of the invention, X 11 Let S be the value of X. 11 For O, S or C(R) B (R) C When L and (R) 115 )n-bonded benzene ring bonding. In X 11 For N(R) A When L and (R) 115 n-bonded benzene ring or X 11 The N-bond represented here. As explained herein, the bond extending to the right from L represents the bond with (R) 115 )n-bonded benzene ring bonding or in X 11 When N is the same as X 11 (i.e., N) bonding.

[0400] In general formula (5), A 11 and A 12 Each ring is independently a benzene ring, furan ring, thiol ring, pyrrole ring, or cyclopentadiene ring, and these rings may be further fused with other rings or substituted. In a preferred embodiment of the invention, A 11 It is a benzene ring. In a preferred embodiment of the invention, A 12 It is a benzene ring. In a further preferred embodiment of the invention, A 11 and A 12 All are benzene rings. In one embodiment of the present invention, A 11 and A 12 At least one of them is a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring. In one aspect of the invention, A 11 and A 12 At least one of them is a furan ring. In one aspect of the invention, A 11 and A 12 At least one of them is a thiol ring. In one aspect of the invention, A 11 and A 12 At least one of them is a pyrrole ring. In one aspect of the invention, A 11 and A 12 At least one of them is a cyclopentadiene ring.

[0401] The benzene ring, furan ring, thiol ring, pyrrole ring, and cyclopentadiene ring described herein can also be fused with other rings. The fused ring can be any one of aromatic hydrocarbon rings, aromatic heterocycles, aliphatic hydrocarbon rings, or aliphatic heterocycles, and can also be a ring formed by the fusion of two or more of these. Preferably, it is an aromatic hydrocarbon ring, an aromatic heterocycle, or a ring formed by the fusion of two or more of these. Benzene rings are an example of aromatic hydrocarbon rings. Aromatic heterocycles refer to rings containing heteroatoms as ring skeleton constituent atoms and exhibiting aromaticity, preferably 5- to 7-membered rings, for example, 5-membered or 6-membered rings. In one aspect of the invention, furan rings, thiophene rings, and pyrrole rings can be used as aromatic heterocycles. Aliphatic hydrocarbon rings are preferably hydrocarbon rings that do not exhibit aromaticity, preferably 5- to 7-membered rings, for example, 5-membered or 6-membered rings. For example, cyclopentadiene rings can be used. Aliphatic heterocycles are rings that contain heteroatoms as the ring backbone and do not exhibit aromaticity. They are preferably 5- to 7-membered rings, such as 5-membered or 6-membered rings.

[0402] In one aspect of the invention, A 11 It is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or two or more of these rings. In one aspect of the invention, A 11It is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or two or more of these rings. In one aspect of the invention, A 11 It is a benzene ring, and the benzene ring is fused with the furan ring of benzofuran or the thiophene ring of benzothiophene. In one aspect of the invention, A 11 Fusing with the furan ring of benzofuran. In one aspect of the invention, A 11 Fusing with the thiophene ring of benzothiophene. In one embodiment of the invention, A 12 It is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or two or more of these rings. In one aspect of the invention, A 12 It is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or two or more of these rings. In one aspect of the invention, A 12 It is a benzene ring, and the benzene ring is fused with the furan ring of benzofuran or the thiophene ring of benzothiophene. In one aspect of the invention, A 12 Fusing with the furan ring of benzofuran. In one aspect of the invention, A 12 It fuses with the thiophene ring of benzothiophene.

[0403] Composition A 11 Or A 12 The hydrogen atoms in the ring can be replaced by deuterium atoms or substituents. The substituents can be selected from any of the substituent groups A to E, for example, from substituent group E. In one embodiment of the invention, A... 11 Or A 12 The ring can be substituted by one atom or group 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, or a combination of two or more groups. In one embodiment of the invention, A... 11 Or A 12 The ring can be substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. In one embodiment of the invention, A... 11 Or A 12 At least one of the rings is substituted by a deuterium atom, an alkyl group, an aryl group, or a combination thereof. Additionally, in the case of a ring containing a pyrrole ring as a constituent of A... 11 Or A 12 When forming a ring, it is preferable that the pyrrole ring's ring skeleton consists of a nitrogen atom bonded to an aryl group that can be substituted with a deuterium atom, alkyl group, or aryl group (the nitrogen atom in the indole ring described later is the same). In constituting A... 11 Or A 12 When two or more hydrogen atoms in a ring are substituted, these can be replaced by the same atom or group, or by different atoms or groups.

[0404] In general formula (5), R 111 ~R 114 R B R C Each of these can independently represent 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. R 115 Each of these can independently represent 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 with L (i.e., a single bond with L). R A This refers to 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 with L). For aryl, heteroaryl, and alkyl groups, please refer to the above descriptions of "aryl," "heteroaryl," and "alkyl." The aryl group preferably has 6 to 14 carbon atoms; examples include phenyl, 1-naphthyl, and 2-naphthyl. The heteroaryl group preferably consists of a 5-membered or 6-membered ring; examples include 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazole-9-yl, dibenzofuranyl, and dibenzothiopheneyl. The alkyl group preferably has 1 to 6 carbon atoms; examples include methyl, ethyl, isopropyl, and tert-butyl. These aryl, heteroaryl, and alkyl groups can be substituted. When substituted, it is preferable to be substituted by a group obtained from one or more atoms or groups selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, and cyano groups; more preferably, it is substituted by a group obtained from one or more atoms or groups selected from the group consisting of deuterium, aryl, heteroaryl, and alkyl groups. In one aspect of the invention, R... 112 It can be a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. In one embodiment of the invention, R 111 ~R 114 Each can be a hydrogen atom or a deuterium atom, independently.

[0405] R 111 and R 112 R 112 and R 113 R 113 and R 114 2 adjacent R 115 R B and R C They can bond together to form a ring structure. Regarding the ring structure described herein, please refer to A above. 11 and A 12 The description of the ring further fused with the benzene ring in the explanatory column. In one aspect of the invention, R 111 and R 112 R 112 and R 113R 113 and R 114 One group of rings bonds to each other 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).

[0406] In one aspect of the invention, the group bonded to L from the left side in general formula (5) is a substituted or unsubstituted carbazole-9-yl group. For example, it is a carbazole-9-yl group in which at least one of the 3- or 6-positions (preferably both) is substituted by a group obtained by a deuterium atom, alkyl group, aryl group, or a combination thereof. Furthermore, it can be an unsubstituted carbazole-9-yl group. In one aspect of the invention, the group bonded to L from the left in general formula (5) is a substituted or unsubstituted benzofuran[2,3-a]carbazole-12-yl, a substituted or unsubstituted benzofuran[3,2-a]carbazole-12-yl, a substituted or unsubstituted benzofuran[2,3-b]carbazole-7-yl, a substituted or unsubstituted benzofuran[3,2-b]carbazole-11-yl, a substituted or unsubstituted benzofuran[2,3-c]carbazole-8-yl, or a substituted or unsubstituted benzofuran[3,2-c]carbazole-5-yl. In one aspect of the invention, the group bonded to L from the left in general formula (5) is a substituted or unsubstituted benzothieno[2,3-a]carbazole-12-yl, a substituted or unsubstituted benzothieno[3,2-a]carbazole-12-yl, a substituted or unsubstituted benzothieno[2,3-b]carbazole-7-yl, a substituted or unsubstituted benzothieno[3,2-b]carbazole-11-yl, a substituted or unsubstituted benzothieno[2,3-c]carbazole-8-yl, or a substituted or unsubstituted benzothieno[3,2-c]carbazole-5-yl. In one aspect of the invention, the group bonded to L from the left side in general formula (5) is a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazole-12-yl, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazole-12-yl, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazole-7-yl, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazole-11-yl, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazole-8-yl, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazole-5-yl.

[0407] In one aspect of the invention, the group bonded to L from the right side in general formula (5) may also be the group exemplified above as the group bonded to L from the left side. This group is not the unsubstituted carbazole-9-yl.

[0408] In the following examples, specific examples of groups that can be used as groups bonded from the left side of L in general formula (5) are given. The groups that can be used in this invention are not to be interpreted as limiting by these specific examples. Furthermore, in the following examples, the methyl group is omitted. Therefore, for example, Z2 or Z3 is substituted with a methyl group. * indicates the bonding position with L.

[0409] [Chemical Formula 42]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419] In addition to the specific examples mentioned above, groups in which all hydrogen atoms of the alkyl groups of 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. Furthermore, groups in which the phenyl groups (C6H5) of Z4 to Z6, Z19 to Z86, and Z111 to Z178 are replaced with deuterated C6D5 groups are exemplified here as Z4(p) to Z6(p), Z19(p) to Z86(p), and Z111(p) to Z178(p), respectively. Furthermore, all the hydrogen atoms of Z1 to Z196 that are deuterated are exemplified here as Z1(D) to Z196(D).

[0420] Regarding specific examples of groups that can be used as the group bonded from the right side of L in general formula (5), in addition to the aforementioned Z2 to Z196 and these deuterium-substituted derivatives, the following specific examples can be given. The groups that can be used in this invention are not to be interpreted as limiting in these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. * indicates the bonding position with L.

[0421] [Chemical Formula 43]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427] In addition to the specific examples mentioned above, the groups in which the methyl (CH3) groups of X31 to X33 and X64 to X79 are substituted with deuterated CD3 are exemplified here as X31(m) to X33(m) and X64(m) to X79(m), respectively. Furthermore, the groups in which the phenyl (C6H5) groups of X5 to X21, X38 to X54, and X68 to X70 are substituted with deuterated C6D5 are exemplified here as X5(p) to X21(p), X38(p) to X54(p), and X68(p) to X70(p), respectively. Moreover, the groups in which all hydrogen atoms of X1 to X79 are deuterated are exemplified here as X1(D) to X79(D), respectively.

[0428] In general formula (5), n represents an integer of 3 or 4. In X 11 For O, S or C(R) B (R) C When L and (R) 115 The benzene ring is bonded with n bonds, therefore n is 3. In X 11 For N(R) A And L and (R) 115 In the case of n-bonded benzene rings, n is 3, and in X 11 For N(R) A And L and X 11 In the case of N-bonding, n is 4. n R 115 They can be the same as each other, or they can be different.

[0429] In general formula (5), L represents a single bond, a substituted or unsubstituted arylene, a substituted or unsubstituted heteroarylene, or a linking group consisting of two or more of these. For the aryl structure of arylene and the heteroaryl structure of heteroarylene, refer to the above description of "aryl" and "heteroaryl". Arylene and heteroarylene can be substituted. In the case of substitution, it is preferably substituted by a group obtained by one or more atoms or groups selected from the group consisting of deuterium, aryl, heteroaryl, alkyl, and cyano, and more preferably by a group obtained by one or more atoms or groups selected from the group consisting of deuterium, aryl, heteroaryl, and alkyl. In the case of substitution, methyl, ethyl, isopropyl, tert-butyl, phenyl, or deuterated derivatives of these are preferred. In one embodiment of the invention, L is an unsubstituted arylene.

[0430] Specific examples of L are given below. However, the L used in this invention is not to be interpreted as limiting in these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are substituted with a methyl group. * indicates a bonding position. L1 is a single bond.

[0431] [Chemical Formula 44]

[0432]

[0433] In one embodiment of the present invention, the groups bonded to the left side of L in general formula (5) are selected from Z1 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated derivatives (Embodiment 1). In one embodiment of the present invention, the groups bonded to the left side of L are selected from Z1 to Z12 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated derivatives (Embodiment 2). In one embodiment of the present invention, the groups bonded to the left side of L are selected from Z13 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X79 and their deuterated derivatives (Embodiment 3). In one embodiment of the present invention, the groups bonded to the left side of L are selected from Z1 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X66 and their deuterated derivatives (Embodiment 4). In one embodiment of the invention, the groups bonded to the left side of L are selected from Z1 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X33 and their deuterated derivatives (Embodiment 5). In another embodiment of the invention, the groups bonded to the left side of L are selected from Z1 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X1 to X21, X31 to X33 and their deuterated derivatives (Embodiment 6). In another embodiment of the invention, the groups bonded to the left side of L are selected from Z1 to Z196 and their deuterated derivatives, and the groups bonded to the right side of L are selected from X22 to X30 and their deuterated derivatives (Embodiment 7).

[0434] In one embodiment of the present invention, in embodiment 1, L is L1. In one embodiment of the present invention, in embodiment 2, L is L1. In one embodiment of the present invention, in embodiment 3, L is L1. In one embodiment of the present invention, in embodiment 4, L is L1. In one embodiment of the present invention, in embodiment 5, L is L1. In one embodiment of the present invention, in embodiment 6, L is L1. In one embodiment of the present invention, in embodiment 7, L is L1.

[0435] In one embodiment of the present invention, in embodiment 1, L is L6. In one embodiment of the present invention, in embodiment 2, L is L6. In one embodiment of the present invention, in embodiment 3, L is L6. In one embodiment of the present invention, in embodiment 4, L is L6. In one embodiment of the present invention, in embodiment 5, L is L6. In one embodiment of the present invention, in embodiment 6, L is L6. In one embodiment of the present invention, in embodiment 7, L is L6.

[0436] In one embodiment of the present invention, in embodiment 1, L is L14. In one embodiment of the present invention, in embodiment 2, L is L14. In one embodiment of the present invention, in embodiment 3, L is L14. In one embodiment of the present invention, in embodiment 4, L is L14. In one embodiment of the present invention, in embodiment 5, L is L14. In one embodiment of the present invention, in embodiment 6, L is L14. In one embodiment of the present invention, in embodiment 7, L is L14.

[0437] In one embodiment of the present invention, in embodiment 1, L is L16. In one embodiment of the present invention, in embodiment 2, L is L16. In one embodiment of the present invention, in embodiment 3, L is L16. In one embodiment of the present invention, in embodiment 4, L is L16. In one embodiment of the present invention, in embodiment 5, L is L16. In one embodiment of the present invention, in embodiment 6, L is L16. In one embodiment of the present invention, in embodiment 7, L is L16.

[0438] Specific examples of compounds represented by general formula (5) are shown below. The compounds represented by general formula (5) that may be used in this invention are not to be interpreted as limitingly specific in the following examples.

[0439] [Chemical Formula 45]

[0440]

[0441] In addition to the specific examples mentioned above, compounds in which all hydrogen atoms present in the substituted or unsubstituted carbazole-9-group of H1 to H13 are replaced by deuterium atoms are exemplified here as H1(d) to H13(d). Furthermore, compounds in which all hydrogen atoms present in H1 to H13 are replaced by deuterium atoms are exemplified here as H1(D) to H13(D).

[0442] Regarding the molecular weight of the compound represented by general formula (5), for example, when attempting to form an organic layer containing the compound represented by general formula (5) by vapor deposition, it is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 800 or less, 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 (5).

[0443] The compounds represented by general formula (5) with smaller dipole moments exhibit higher orientation during film formation and are therefore preferred. The dipole moment is preferably less than 2.3, more preferably less than 2.0, even more preferably less than 1.7, and even more preferably less than 1.4.

[0444] As a compound represented by general formula (5), a compound can be selected from those composed of atoms chosen from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. For example, as a compound represented by general formula (5), a compound can be selected from those composed of atoms chosen from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. For example, as a compound represented by general formula (5), a compound can be selected from those composed of atoms chosen from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. For example, as a compound represented by general formula (5), a compound can be selected from those composed of atoms chosen from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms.

[0445] The following describes the components of an organic electroluminescent element and its layers other than the light-emitting layer.

[0446] Substrate:

[0447] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and can be any of those substrates commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz and silicon.

[0448] anode:

[0449] In some embodiments, the anode of the organic electroluminescent device is made of a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (above 4 eV). 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 fabricated by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, where high precision (e.g., above about 100 μm) may not be required for the pattern, the pattern can be formed using a mask of a preferred shape used when vapor deposition or sputtering on the electrode material. In some embodiments, wet film formation methods, such as printing and coating, are used when a coating material (such as an organic conductive compound) can be applied. In some embodiments, the transmittance of the anode is greater than 10% when the emitted light passes through it, and the sheet resistance of the anode is less than several hundred ohms per square meter. In some embodiments, the thickness of the anode is 10–1,000 nm. In some embodiments, the thickness of the anode is 10–200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0450] cathode:

[0451] In some embodiments, the cathode is made of a metal (below 4 eV) (referred to as an electron-injecting metal), alloy, conductive compound, or combination thereof, with an electrode material having a low work function. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, indium, lithium-aluminum mixtures, and rare earth metals. In some embodiments, a mixture of the electron-injecting metal and a second metal is used, the second metal being a stable metal with a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, lithium-aluminum mixtures, and aluminum. In some embodiments, the mixture enhances electron-injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film using vapor deposition or sputtering. In some embodiments, the film resistivity of the cathode is below several hundred ohms per square meter. In some embodiments, the thickness of the cathode is in the range of 10 nm to 5 μm. In some embodiments, the thickness of the cathode is in the range of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent element is transparent or translucent in order to transmit the emitted light. In some embodiments, transparent or translucent electroluminescent elements enhance the luminous brightness.

[0452] In some embodiments, the cathode is formed using a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, the element comprises both a transparent or translucent anode and cathode.

[0453] Injection layer:

[0454] The injection layer is a layer located between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminous intensity. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the luminescent layer or hole transport layer, and between the cathode and the luminescent layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present.

[0455] Here are some examples of preferred compounds that can be used as hole injection materials.

[0456] [Chemical Formula 46]

[0457] MoO3,

[0458]

[0459] Next, preferred examples of compounds that can be used as electron injection materials will be given.

[0460] [Chemical Formula 47]

[0461] LiF, CsF,

[0462] Barrier layer:

[0463] A blocking layer is a layer capable of suppressing the diffusion of charges (electrons or holes) and / or excitons located in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, an electron blocking layer is located between the light-emitting layer and the hole transport layer, and suppresses electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, a hole blocking layer is located between the light-emitting layer and the electron transport layer, and suppresses holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer suppresses exciton diffusion to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that function as both electron blocking layers and exciton blocking layers.

[0464] Cavity blocking layer:

[0465] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer suppresses holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material described for the electron transport layer.

[0466] Here are some examples of preferred compounds that can be used in hole-blocking layers.

[0467] [Chemical Formula 48]

[0468]

[0469] Electron blocking layer:

[0470] Holes are transported by an electron blocking layer. In some embodiments, the electron blocking layer suppresses electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material described for the hole transport layer.

[0471] Here are specific examples of preferred compounds that can be used as electron blocking materials.

[0472] [Chemical Formula 49]

[0473]

[0474] Exciton blocking layer:

[0475] An exciton blocking layer suppresses the diffusion of excitons generated via the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons within the light-emitting layer. In some embodiments, it enhances the luminous efficiency of the device. In some embodiments, the exciton blocking layer may be present adjacent only to either the anode or cathode side of the light-emitting layer, or one exciton blocking layer may be present adjacent to the anode side of the light-emitting layer and another exciton blocking layer may be present adjacent to the cathode side of the light-emitting layer. In some embodiments, when the exciton blocking layer is on the anode side, it may be located between and adjacent to the hole transport layer and the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, it may be located between and adjacent to the light-emitting layer and the cathode. In some embodiments, a hole injection layer, an electron blocking layer, or the same layer is located between the anode and the exciton blocking layer, with 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 the same layer is located between the cathode and the exciton blocking layer, the exciton blocking layer being adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the light-emitting material, respectively.

[0476] Hole transport layer:

[0477] 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.

[0478] In some embodiments, the hole transport material has one of the characteristics of hole injection or transport and electron blocking. 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 this invention are not limited, and examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkyl derivatives, pyrazolene derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene 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 styreneamine 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.

[0479] [Chemical Formula 50]

[0480]

[0481] Electron transport layer:

[0482] 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.

[0483] In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode into 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 this invention are not limited, and can include nitro-substituted fluorene derivatives, dibenzoquinone derivatives, thiopiperanoxide derivatives, carbodiimide, fluorenemethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, aziridine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0484] [Chemical Formula 51]

[0485]

[0486] Furthermore, examples of compounds that are preferred as materials that can be added to each organic layer are given. For example, they can be considered as stabilizing materials.

[0487] [Chemical Formula 52]

[0488]

[0489] Preferred materials that can be used in organic electroluminescent devices are specifically illustrated, but the materials that can be used in this invention are not limited to the following exemplary compounds. Furthermore, even compounds illustrated as materials with specific functions can be used as materials with other functions.

[0490] Device:

[0491] In some implementations, the light-emitting layer is incorporated into the device. For example, the device includes, but is not limited to, OLED bulbs, OLED lights, television screens, computer monitors, mobile phones, and tablet computers.

[0492] In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode.

[0493] In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be used to facilitate charge transfer or energy transfer within the device and / or be suitable as hole transport materials. Examples of such devices include, for instance, 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 photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0494] Light bulb or lamp:

[0495] In some embodiments, the electronic device includes an OLED, which includes an anode, a cathode, and at least one organic layer containing a light-emitting layer located between the anode and the cathode.

[0496] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations 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.

[0497] In some embodiments, the device is an OLED lamp, the OLED lamp comprising:

[0498] The circuit board has a first surface with a mounting surface and a second surface opposite to it, and defines at least one opening.

[0499] At least one OLED is disposed on the mounting surface and has a structure in which the at least one OLED includes an anode, a cathode and at least one organic layer containing a light-emitting layer located between the anode and the cathode and emits light;

[0500] Housing, used for circuit board; and

[0501] At least one connector is disposed at an end of the housing, and the housing and the connector define an encapsulation suitable for mounting to a lighting device.

[0502] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board to emit light in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0503] Monitor or screen:

[0504] In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, methods including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD) are used to deposit the compounds involved in the present invention onto a substrate. In some embodiments, the substrate is a photographic plate structure suitable for double-sided etching, providing pixels with a unique aspect ratio. The screen (which may also be referred to as a mask) is used in methods for manufacturing OLED displays. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and promotes large swept-bevel openings in the horizontal direction. This allows for tight patterning of pixels required for high-definition displays while optimizing chemical vapor deposition onto the TFT substrate.

[0505] Internal patterning of pixels allows for the construction of 3D pixel openings with varying aspect ratios in both the horizontal and vertical directions. Furthermore, imaging "strips" or halftone circles within the pixel region suppress etching in specific areas until these specific patterns are undercut and leave the substrate. At this point, all pixel regions are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone patterns allows etching to be suppressed at different rates within the pixel, enabling locally deeper etching to form steep vertical bevels.

[0506] The preferred material for vapor deposition masks is invar steel. Invar steel is a metal alloy that is cold-rolled into long thin sheets in a steel mill. Invar steel cannot be used as a nickel mask for electrodeposition onto a spin mandrel. A suitable and low-cost method for forming opening regions within a vapor deposition mask is a wet chemical etching method.

[0507] 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 other embodiments, the screen or display pattern is fabricated using plasma etching.

[0508] Method for manufacturing the device:

[0509] OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit panels. Generally, each unit panel on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate, applying a planarization film onto the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0510] In another aspect of the invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising:

[0511] The process of forming a barrier layer on the substrate of the motherboard;

[0512] The process of forming multiple display units from unit board units on the barrier layer;

[0513] The process of forming an encapsulation layer on each of the display units of the unit board; and

[0514] The process of coating an organic film on the interface portion between the unit plates.

[0515] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edge portions of the barrier layer are covered with an organic film formed of polyimide or acrylamide. In some embodiments, the organic film facilitates the gentle cutting of the motherboard into unit panels.

[0516] In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and a source / drain electrode. Each of the plurality of display units may include a thin-film transistor (TFT), a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein an organic film coated on the interface portion is formed of the same material as the planarization film and is formed concurrently with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer, with a passivation layer, a planarization film, and an encapsulation layer therebetween, and the encapsulation layer covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film neither contacts the display unit nor the encapsulation layer.

[0517] Each of the organic film and the planarization film may comprise either polyimide or acryloyl groups. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the substrate may be formed of polyimide. The method may further include mounting a carrier substrate formed of a glass material onto another surface of the substrate before forming the barrier layer on one surface of the substrate formed of polyimide, and separating the carrier substrate from the substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0518] In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylamide, as in the case of an organic film formed on the edge portion of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge portion of the barrier layer such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0519] In some embodiments, the light-emitting layer has a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source / drain electrode of the TFT layer.

[0520] In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the opposing electrode, thereby causing the organic light-emitting layer to emit light and thus forming an image. Hereinafter, the image forming unit having a TFT layer and light-emitting units will be referred to as a display unit.

[0521] In some embodiments, the encapsulation layer covering the display units and preventing external moisture penetration can be formed as a thin-film encapsulation structure having alternating layers of organic and inorganic films. In some embodiments, the encapsulation layer has a thin-film encapsulation structure having multiple layers of films. In some embodiments, the organic film coated on the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0522] In one embodiment, the OLED display is flexible and uses a soft substrate formed of polyimide. In some embodiments, the substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0523] In some embodiments, a barrier layer is formed on the surface of the substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit plate. For example, while forming the substrate over the entire surface of the motherboard, the barrier layer is formed according to the size of each unit plate, thereby forming a groove at the interface portion between the unit plate barrier layers. Each unit plate can be cut along the groove.

[0524] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, a TFT layer is formed for each unit panel, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are disposed on the TFT layer to cover the TFT layer. The groove at the interface portion is covered with an organic film, such as a polyimide or acrylamide, while a planarization film formed of, for example, polyimide or acrylamide is formed. This is to prevent cracking by allowing the organic film to absorb shocks generated when each unit panel is cut along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the shock generated when each unit panel is cut along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, because the grooves at the interface portions between the barrier layers are covered with an organic film, and this organic film absorbs impacts that would otherwise be transferred to the barrier layers, each unit panel can be cut gently, and cracking in the barrier layers can be prevented. In one embodiment, the organic film covering the grooves at the interface portions is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected as a single layer, then because external moisture may penetrate into the display unit through the planarization film and a portion of the residual organic film, the organic film and the planarization film are spaced apart from each other so that the organic film is separated from the display unit.

[0525] In some embodiments, a display unit is formed by forming light-emitting units, and an encapsulation layer is disposed on the display unit to cover it. Thus, after the motherboard is fully manufactured, a carrier substrate supporting the substrate is separated from the substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate separates from the substrate due to the difference in thermal expansion coefficients between the carrier substrate and the substrate.

[0526] In some embodiments, the motherboard is cut into unit panels. In some embodiments, the motherboard is cut along the interface portion between the unit panels using a cutting machine. In some embodiments, because the grooves at the interface portion along which the motherboard is cut are covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting.

[0527] In some implementations, the method reduces the defect rate of the product and stabilizes its quality.

[0528] Another approach is an OLED display having: a barrier layer formed on a substrate; a display unit formed on the barrier layer; an encapsulation layer formed on the display unit; and an organic film coated on the edge portion of the barrier layer.

[0529] Example

[0530] The following examples and embodiments further illustrate the features of the present invention. The materials, processing methods, and processing steps shown below can be appropriately modified without departing from the spirit of the invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below. Furthermore, the evaluation of luminescence characteristics was performed using a source meter (Keithley 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd. E5273A), an optical power meter (Newport Corporation 1930C), a spectrometer (Ocean Optics USB2000), a spectroradiometer (TOPCON CORPORATION SR-3), and a streak camera (Hamamatsu Photonics KK C4334).

[0531] (Synthetic Example 1) Synthesis of Compound C1

[0532] Compound C

[0533] [Chemical Formula 53]

[0534]

[0535] A mixture of tetrahydrofuran (THF, 140 mL) and water (70 mL) of compound a (5.29 g, 13.7 mmol) was bubbled under nitrogen. Compound b (10.4 g, 28.1 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.96 g, 1.37 mmol), and sodium carbonate (7.31 g, 69.0 mmol) were added to this solution under nitrogen flow, and the mixture was heated and stirred at 75 °C for 15 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the resulting gray solid was washed with dichloromethane and ethyl acetate. The solid was dissolved in heated 1,2-dichlorobenzene (ODCB) and passed through a funnel (Kiriyama funnel) lined with diatomaceous earth / silica gel / diatomaceous earth while heated. The solution was concentrated under reduced pressure using an evaporator, and the resulting solid was washed with toluene and dried to obtain compound c (7.24 g, 9.06 mmol, yield 66%), a pale yellow solid.

[0536] ASAP MS spectral analysis: C 48 HD 26 F3N8: Theoretical value 798.39, observed value 799.46

[0537] Compound C1

[0538] [Chemical Formula 54]

[0539]

[0540] Under a nitrogen stream, potassium carbonate (0.57 g, 4.15 mmol) was added to a solution of compound C (0.83 g, 1.04 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.60 g, 3.42 mmol) in N,N-dimethylformamide (DMF, 40 mL), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C1 (0.35 g, 0.276 mmol, yield 27%).

[0541] 1 H-NMR (400MHz, CDCl3): δ9.26 (s, 1H)

[0542] ASAP MS spectral analysis: C 84 HD 50 N 11 Theoretical value: 1263.7, observed value: 1263.1

[0543] (Synthesis Example 2) Synthesis of Compound C2

[0544] Compound C2

[0545] [Chemical Formula 55]

[0546]

[0547] Under a nitrogen stream, potassium carbonate (0.34 g, 2.50 mmol) was added to a solution of compound C (0.50 g, 0.62 mmol), 5H-benzofuran[3,2-c]carbazole (0.48 g, 1.87 mmol), and N-methyl-2-pyrrolidone (NMP, 30 mL), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C2 (0.44 g, 0.29 mmol, 47% yield).

[0548] ASAP MS spectral analysis: C 102 H 31 D 26 N 11 O3: Theoretical value 1509.6, observed value 1510.7

[0549] (Synthesis Example 3) Synthesis of Compound C3

[0550] compound d

[0551] [Chemical Formula 56]

[0552]

[0553] Under a nitrogen stream, potassium carbonate (0.86 g, 6.25 mmol) was added to a 90 mL NMP solution of compound c (2.0 g, 2.50 mmol) and 5H-benzofuran[3,2-c]carbazole (1.28 g, 5.00 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give yellow compound d (1.93 g, 1.51 mmol, yield 61%).

[0554] 1 H-NMR (400MHz, CDCl3): δ9.40(s,1H),8.40-8.30(m,2H),8.12-7.90(m,4H),7.80-7.30(m,14H).

[0555] ASAP MS spectral analysis: C 84 H 21 D26 FN 10 O2: Theoretical value 1272.5, observed value 1272.8

[0556] Compound C3

[0557] [Chemical Formula 57]

[0558]

[0559] Under a nitrogen stream, potassium carbonate (0.76 g, 5.52 mmol) was added to a DMF (50 mL) solution of compound d (1.76 g, 1.38 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.72 g, 4.14 mmol), and the mixture was stirred at 80 °C for 72 h. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C3 (0.30 g, 0.21 mmol, 15% yield).

[0560] 1 H-NMR (400MHz, CDCl3): δ9.37 (s, 1H), 7.97 (dd, J = 4.8Hz, 1.2Hz, 2H), 7.80 (d, J = 8.4Hz, 2H), 7.6 1-7.56(m,2H),7.51(d,J=8.4Hz,2H),7.45-7.35(m,4H),7.34-7.22(m,4H),7.10-7.00(m,4H).

[0561] ASAP MS spectral analysis: C 96 H 21 D 34 N 11 O2: Theoretical value 1427.6, observed value 1427.8

[0562] (Synthetic Example 4) Synthesis of Compound C4

[0563] compound e

[0564] [Chemical Formula 58]

[0565]

[0566] A mixture of THF (60 mL) and water (30 mL) of compound a (2.30 g, 5.99 mmol) was bubbled with nitrogen. Under a nitrogen stream, 2-chloro-4,6-(diphenyl-2,3,4,5,6-d5)-1,3,5-triazine (3.39 g, 12.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.42 g, 0.59 mmol), and sodium carbonate (3.17 g, 29.9 mmol) were added to the solution, and the mixture was heated and stirred at 75 °C for 18 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the resulting gray solid was washed with dichloromethane and ethyl acetate. The solid was dissolved in heated ODCB and passed through a funnel (Kiriyama funnel) lined with diatomaceous earth / silica gel / diatomaceous earth while heated. The solution was concentrated under reduced pressure using an evaporator, and the resulting solid was washed with toluene and dried to obtain a pale yellow solid of compound e (2.54 g, 4.13 mmol, yield 69%).

[0567] ASAP MS spectral analysis: C 36 HD 20 F3N6: Theoretical value 614.30, observed value 615.40

[0568] compound f

[0569] [Chemical Formula 59]

[0570]

[0571] Under a nitrogen stream, potassium carbonate (1.12 g, 8.13 mmol) was added to a 120 mL NMP solution of compound e (2.0 g, 3.25 mmol) and 5H-benzofuran[3,2-c]carbazole (1.67 g, 6.50 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered through a funnel containing diatomaceous earth (Kiriyama funnel), and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was filtered, concentrated under reduced pressure using an evaporator, purified by column chromatography (toluene:hexane = 1:1), and the solid was washed with methanol to give a yellow compound f (2.61 g, 2.39 mmol, 73% yield).

[0572] 1H-NMR (400MHz, CDCl3): δ9.61 (d, J = 1.6Hz, 1H), 8.46 (d, J = 7.6Hz, 2H), 8.00-7.96 (m, 4H), 7.70 (d, J = 8.4Hz, 2H), 7.48-7.38 (m, 12H).

[0573] ASAP MS spectral analysis: C 72 H 21 D 20 FN8O2: Theoretical value 1088.46, observed value 1089.66

[0574] Compound C4

[0575] [Chemical Formula 60]

[0576]

[0577] Under a nitrogen stream, potassium carbonate (0.41 g, 2.96 mmol) was added to a 50 mL NMP solution of compound f (1.61 g, 1.47 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.31 g, 1.77 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C4 (1.59 g, 1.27 mmol, 86% yield).

[0578] 1 H-NMR (400MHz, CDCl3): δ9.49 (s, 1H), 8.01 (d, J = 7Hz, 2H), 7.83 (d, J = 7Hz, 2H) 7.59-7.52 (m, 4H), 7.38-7.28 (m, 8H), 7.10-7.12 (m, 4H).

[0579] ASAP MS spectral analysis: C 84 H 21 D 28 N9O2: Theoretical value 1243.58, observed value 1244.73

[0580] (Synthetic Example 5) Synthesis of Compound C5

[0581] Compound C5

[0582] [Chemical Formula 61]

[0583]

[0584] Under a nitrogen stream, potassium carbonate (0.25 g, 1.83 mmol) was added to a 50 mL NMP solution of compound f (1.0 g, 0.91 mmol), 5H-benzofuran[3,2-c]carbazole (0.28 g, 1.10 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with 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 give a yellow compound C5 (0.99 g, 0.746 mmol, 82% yield).

[0585] 1 H-NMR (400MHz, CDCl3): δ9.53 (s, 1H), 8.0-6.76 (m, 30H)

[0586] ASAP MS spectral analysis: C 90 H 31 D 20 N9O3: Theoretical value 1325.54, observed value 1327.79

[0587] (Synthetic Example 6) Synthesis of Compound C6

[0588] compound h

[0589] [Chemical Formula 62]

[0590]

[0591] A mixture of THF (200 mL) and water (80 mL) of compound a (4.84 g, 12.6 mmol) was bubbled with nitrogen. Under a nitrogen flow, compound g (9.40 g, 25.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.88 g, 1.26 mmol), and sodium carbonate (6.69 g, 105.9 mmol) were added to this solution, and the mixture was heated and stirred at 75 °C for 15 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the resulting gray solid was washed with water and toluene to obtain compound h (9.2 g, 11.6 mmol, 92% yield) as a gray solid.

[0592] ASAP MS spectral analysis: C 48 H 11 D16 F3N8: Theoretical value 788.3, ​​observed value 789.62

[0593] Compound C6

[0594] [Chemical Formula 63]

[0595]

[0596] Under a nitrogen stream, potassium carbonate (1.05 g, 7.60 mmol) was added to a DMF (70 mL) solution of compound h (1.50 g, 1.90 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.33 g, 7.60 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C6 (0.66 g, 0.52 mmol, yield 28%).

[0597] 1 H-NMR (400MHz, CDCl3): δ9.25(s,1H),7.52-7.48(m,4H),7.42-7.38(m,2H),7.26-7.16(m,4H)

[0598] ASAP MS spectral analysis: C 84 H 11 D 40 N 11 Theoretical value: 1253.6, observed value: 1254.0

[0599] (Synthetic Example 7) Synthesis of Compound C7

[0600] compound j

[0601] [Chemical Formula 64]

[0602]

[0603] To a mixed solution of 1,5-dibromo-2,4-difluoro-3-iodobenzene (15.8 g, 39.9 mmol) in toluene (100 mL) and deionized water (30 mL), 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, and the mixture was stirred at 100 °C for 23 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, and saturated brine was added to separate the organic and aqueous phases. After extraction of the aqueous phase with toluene, the combined organic phases were dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated. The crude product was purified by silica gel chromatography (hexane) to give 9.0 g of compound j as a white solid (25.5 mmol, yield 64%).

[0604] 1 H-NMR (400MHz, CDCl3): δ7.77 (t, J=6.8Hz, 1H).

[0605] ASAP MS spectral analysis: C 12 HD5Br2F2: Theoretical value 350.91, observed value 350.93 [M]

[0606] compound k

[0607] [Chemical Formula 65]

[0608]

[0609] The reaction mixture of compound j (2.1 g, 5.98 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.22 g, 0.30 mmol), potassium acetate (4.1 g, 42.0 mmol), bis(pinacol)diboron (7.1 g, 27.9 mmol), and 1,4-dioxane (60 mL) was stirred for 15 hours at 110 °C. After cooling the reaction mixture to room temperature, it was diluted with ethyl acetate and filtered through silica gel. The filtrate was concentrated, and the resulting reaction mixture was dissolved in dichloromethane and filtered through silica gel. The obtained solid was washed with hexane to give 1.84 g of compound k (4.11 mmol, 69% yield) as a white solid.

[0610] 1 H-NMR (400MHz, CDCl3): δ8.11 (t, J=7.2Hz, 1H), 1.36 (s, 24H).

[0611] compound m

[0612] [Chemical Formula 66]

[0613]

[0614] Compound k (8.00 g, 17.89 mmol) was dissolved in THF (138 mL) and deionized water (46 mL). 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 the mixture was stirred at 75 °C for 15 hours. The reaction solution was cooled to room temperature, and the resulting gray solid was filtered off. The solid was washed with deionized water, methanol, and THF. The collected solid was stirred in hot toluene, filtered off, and washed with toluene to obtain 4.1 g of a black solid containing compound m (6.05 mmol, 34% yield).

[0615] ASAP MS spectral analysis: C 42 HD 25 F2N6: Theoretical value 677, observed value 678 [M+H] + ]

[0616] Compound C7

[0617] [Chemical Formula 67]

[0618]

[0619] Under a nitrogen stream, potassium carbonate (1.07 g, 7.74 mmol) was added to a 90 mL NMP solution of compound m (1.75 g, 2.58 mmol), 5H-benzofuran[3,2-c]carbazole (1.60 g, 6.22 mmol), and the mixture was stirred at 120 °C for 18 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with 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 give a yellow compound C7 (0.80 g, 0.69 mmol, 27% yield).

[0620] 1H-NMR (400MHz, CDCl3): δ9.51 (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).

[0621] ASAP MS spectral analysis: C 78 H 21 D 25 N8O2: Theoretical value 1151.5, observed value 1151.6

[0622] (Synthetic Example 8) Synthesis of Compound C8

[0623] compound n

[0624] [Chemical Formula 68]

[0625]

[0626] Compound k (1.81 g, 4.05 mmol) was dissolved in THF (30 mL) and deionized water (10 mL). 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 the mixture was stirred at 75 °C for 16 hours. The reaction solution was cooled to room temperature, and the resulting gray solid was filtered off. The solid was washed with deionized water, methanol, and THF. The collected solid was stirred in hot toluene, filtered off, and washed with toluene to obtain 3.30 g of a black solid containing compound n (3.82 mmol, 94% yield).

[0627] ASAP MS spectral analysis: C 54 HD 31 F2N8: Theoretical value 861.47, observed value 862.72 [M+H] + ]

[0628] Compound C8

[0629] [Chemical Formula 69]

[0630]

[0631] A mixture of compound n (2.85 g, 3.30 mmol) and DMF (65 mL) was added with 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), and stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature, the solid was filtered off, and washed with ethyl acetate. The filtrate was concentrated, methanol was added, the resulting solid was filtered off, 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 give 2.13 g of pale green compound C8 (1.81 mmol, 55% yield).

[0632] 1 H-NMR (400MHz, DMSO-d6): δ9.20 (s, 1H).

[0633] ASAP MS spectral analysis: C 78 HD 47 N 10 Theoretical value 1171.70, observed value 1172.15 [M+H] + ]

[0634] (Synthetic Example 9) Synthesis of Compound C9

[0635] compound p

[0636] [Chemical Formula 70]

[0637]

[0638] Under a nitrogen atmosphere at -78°C, a 2.3 M cyclohexane solution of n-butyllithium (21 mL, 48.3 mmol) was slowly added dropwise to a THF (75 mL) 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) (12.8 mL, 56.4 mmol). After stirring for 80 minutes, triisopropylboronic acid ester (12.8 mL, 56.4 mmol) was added, and the reaction solution was heated to room temperature. After stirring for 2 hours, the solution was cooled to 0°C, and a 4N hydrochloric acid aqueous solution (70 mL) was added. After stirring at room temperature for 30 minutes, the organic and aqueous phases were separated. The aqueous phase was extracted with diethyl ether, and the combined organic phases were washed with deionized water and saturated brine. The organic phase was concentrated and the resulting white solid was washed with hexane to obtain 9.30 g of white compound p (32.7 mmol, yield 87%).

[0639] 1H-NMR (400MHz, DMSO-d6): δ8.26 (brs, 2H), 8.08 (d, J = 1.6Hz, 2H), 7.92-7.93 (m, 1H).

[0640] compound q

[0641] [Chemical Formula 71]

[0642]

[0643] 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 deionized water (10 mL), and the mixture was stirred at 100 °C for 15 h. The reaction solution was cooled to room temperature, and saturated brine was added to separate the organic and aqueous phases. After extraction of the aqueous phase with ethyl acetate, the combined organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated. The crude product was purified by silica gel chromatography (hexane / ethyl acetate = 40:1) and (hexane / dichloromethane = 10:1), and the resulting white solid was washed with hexane to give 4.84 g of compound q (9.48 mmol, 73% yield).

[0644] 1 H-NMR (400MHz, CDCl3): δ7.88(t,J=2.0Hz,1H),7.81(t,J=6.8Hz,1H),7.62(q,J=2.0Hz,2H).

[0645] ASAP MS spectral analysis: C 24 H4D 10 Br2F2: Theoretical value 508.00, observed value 509.03 [M+H] + ]

[0646] compound r

[0647] [Chemical Formula 72]

[0648]

[0649] The reaction mixture of compound q (4.8 g, 9.40 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.36 g, 0.50 mmol), potassium acetate (6.5 g, 66.2 mmol), bis(pinacol)diboron (12.1 g, 47.6 mmol), and 1,4-dioxane (100 mL) was stirred for 15 hours at 110 °C. After cooling the reaction mixture to room temperature, it was diluted with ethyl acetate and filtered through silica gel. The filtrate was concentrated, and the resulting reaction mixture was dissolved in dichloromethane and filtered through silica gel. The obtained solid was washed with hexane to give 5.00 g of compound r (8.27 mmol, 88% yield) as a yellow solid.

[0650] 1 H-NMR (400MHz, CDCl3): δ8.15 (t, J = 6.8Hz, 1H), 7.79-7.80 (m, 1H), 7.66 (brs, 2H), 1.26 (s, 24H).

[0651] ASAP MS spectral analysis: C 36 H 28 D 10 B2F2O4: Theoretical value 604.37, observed value 605.47 [M+H] + ]

[0652] compounds

[0653] [Chemical Formula 73]

[0654]

[0655] Compound r (4.98 g, 8.24 mmol) was dissolved in THF (60 mL) and deionized water (20 mL). 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 the mixture was stirred at 75 °C for 20 hours. The reaction solution was cooled to room temperature, and the resulting gray solid was filtered off. The solid was washed with THF and deionized water. The collected solid was stirred in hot toluene, filtered off, washed with toluene, and dried to obtain 7.98 g of a gray solid containing compound s (7.83 mmol, 95% yield).

[0656] ASAP MS spectral analysis: C 66 H4D36 F2N8: Theoretical value 1018.56, observed value 1019.83 [M+H] + ]

[0657] Compound C9

[0658] [Chemical Formula 74]

[0659]

[0660] A mixture of compound S (3.06 g, 3.00 mmol) and DMF (60 mL) was added with 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), and stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature, the solid was filtered off, and washed with ethyl acetate. The filtrate was concentrated, methanol was added, the resulting solid was filtered off, and washed with methanol. The crude product was purified by column chromatography (toluene / hexane = 1:1 to 2:1), and the solid was reprecipitated with ethyl acetate / hexane to give 1.47 g of the green compound C9 (1.10 mmol, 37% yield).

[0661] 1 H-NMR (400MHz, DMSO-d6): δ9.40(s,1H),7.14(d,J=1.6Hz,2H),7.07(d,J=1.6Hz,1H).

[0662] ASAP MS spectral analysis: C 90 H4D 52 N 10 Theoretical value 1328.80, observed value 1329.84 [M+H] + ]

[0663] (Synthetic Example 10) Synthesis of Compound C10

[0664] compound t

[0665] [Chemical Formula 75]

[0666]

[0667] Under a nitrogen stream, potassium carbonate (3.37 g, 24.4 mmol) was added to a 30 mL NMP solution of compound e (5.0 g, 8.13 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (2.85 g, 16.2 mmol), and the mixture was stirred at 50 °C for 15 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in heated ODCB, and purified by column chromatography (toluene:hexane = 1:1) using this solution. Furthermore, recrystallization from toluene yielded a yellow compound t (4.80 g, 5.18 mmol, 63% yield).

[0668] 1 H-NMR (400MHz, CDCl3): δ9.50 (dd, J=1.6Hz, 1H).

[0669] ASAP MS spectral analysis: C 60 HD 36 FN8: Theoretical value 924.5, observed value 924.7

[0670] Compound C10

[0671] [Chemical Formula 76]

[0672]

[0673] Under a nitrogen stream, potassium carbonate (0.87 g, 6.27 mmol) was added to a DMF (50 mL) solution of compound t (1.45 g, 1.57 mmol) and 5H-benzofuran[3,2-c]carbazole (1.21 g, 4.70 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in heated ODCB, and purified by column chromatography (toluene:hexane = 1:1) using this solution. Recrystallization from toluene yielded a yellow compound C10 (1.47 g, 1.26 mmol, 81% yield).

[0674] 1 H-NMR (400MHz, CDCl3): δ9.44(s,1H),7.87(d,J=7.2Hz,1H),7.74(d,J=7.2Hz,1H), 7.54-7.49(m,1H),7.32-7.22(m,5H),6.93(t,J=7.2Hz,1H),6.78(t,J=7.2Hz,1H).

[0675] ASAP MS spectral analysis: C 78 H 11 D 36 N9O: Theoretical value 1161.6, observed value 1162.1

[0676] (Synthetic Example 11) Synthesis of Compound C11

[0677] Compound C11

[0678] [Chemical Formula 77]

[0679]

[0680] Under a nitrogen stream, potassium carbonate (0.60 g, 4.32 mmol) was added to a DMF (40 mL) solution of compound t (1.0 g, 1.08 mmol) and 2-phenyl-5H-benzofuran[3,2-c]carbazole (1.08 g, 3.24 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solution was then filtered again, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in heated ODCB, and purified by column chromatography (toluene:hexane = 1:1) using the solution as a sample. Furthermore, recrystallization from toluene yielded a yellow compound C11 (0.98 g, 0.08 mmol, 73% yield).

[0681] 1 H-NMR (400MHz, CDCl3): δ9.45(s,1H),8.08(d,J=1.2Hz,1H),7.75(d,J=6.8Hz,1H ),7.54-7.51(m,3H),7.40(t,J=7.2Hz,2H),7.34-7.24(m,6H),7.04-7.00(m,1H).

[0682] ASAP MS spectral analysis: C 84 H 15 D 36 N9O: Theoretical value 1237.6, observed value 1239.2

[0683] (Synthetic Example 12) Synthesis of Compound C12

[0684] compound v

[0685] [Chemical Formula 78]

[0686]

[0687] A solution of compound u (25.7 g, 88.6 mmol) in THF (295 mL) was bubbled with nitrogen and cooled to -78 °C. Under a nitrogen stream, 1 M diisopropylaminolithium (LDA, 99.6 mL, 99.6 mmol) was added dropwise to the solution over 30 minutes. After stirring at -78 °C for 1 hour, CH3OD (7.3 g, 221 mmol) was added, and the mixture was stirred overnight. The solution was heated to room temperature, and a saturated aqueous ammonium chloride solution was added. THF was then removed by distillation using an evaporator. Dichloromethane and water were added, and the organic layer was extracted, washed with saturated brine, and dried with sodium sulfate. The solution was concentrated and purified by silica gel chromatography. Purification by vacuum distillation yielded a clear liquid compound v (10 g, 34.4 mmol, yield 36.6%).

[0688] Compound x

[0689] [Chemical Formula 79]

[0690]

[0691] The reaction mixture of compound v (9 g, 30.9 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (2.3 g, 3.09 mmol), potassium acetate (21.1 g, 21.1 mmol), bis(pinacol)diboron (39.1 g, 154 mmol), and 1,4-dioxane (310 mL) was stirred for 15 hours at 110 °C. After cooling the reaction mixture to room temperature, it was diluted with ethyl acetate and filtered through silica gel. The resulting solid was washed with hexane to give 10.0 g of compound w (25.9 mmol, 76% yield) as a white solid.

[0692] Compound w (10.0 g, 25.9 mmol) was dissolved in THF (260 mL) and deionized water (130 mL). 2-Chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (17.9 g, 64.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.81 g, 2.59 mmol), and sodium carbonate (8.22 g, 77.6 mmol) were added, and the mixture was stirred at 75 °C for 15 hours. The reaction solution was cooled to room temperature and concentrated. The resulting gray solid was filtered off and washed with deionized water, methanol, and THF. The collected solid was stirred in hot toluene, filtered off, and washed with toluene to obtain 1.86 g of a black solid of compound x (3.02 mmol, yield 11.6%).

[0693] ASAP MS spectral analysis: C 36 D 21 F3N6: Theoretical value 615.31, observed value 616.41

[0694] compound y

[0695] [Chemical Formula 80]

[0696]

[0697] Under a nitrogen stream, a THF (71 mL) solution of compound x (1.32 g, 2.14 mmol) and 5H-benzofuran[3,2-c]carbazole (1.37 g, 5.35 mmol) was cooled to -25 °C, and a THF (71 mL) solution of potassium tert-butoxide (0.72 g, 6.42 mmol) was added dropwise. After warming to room temperature, the mixture was stirred for 15 hours. Water was then added, the suspension was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane and purified by column chromatography (toluene:hexane = 1:1). The obtained solid was washed with methanol to obtain 1.18 g of yellow compound y (1.08 mmol, yield 51%).

[0698] 1 H-NMR (400MHz, CDCl3): 8.46 (d, J = 7.6 Hz, 2H), 8.01-7.95 (m, 4H), 7.71 (d, J = 8.4 Hz, 2H), 7.52-7.35 (m, 12H).

[0699] ASAP MS spectral analysis: C 72 H 20 D 21 FN8O2: Theoretical value 1089.47, observed value 1090.61

[0700] Compound C12

[0701] [Chemical Formula 81]

[0702]

[0703] Under a nitrogen stream, potassium carbonate (0.15 g, 1.09 mmol) was added to a 5.5 mL NMP solution of compound y (0.60 g, 0.55 mmol) and 9H-carbazole-3-carboxynitrile (0.16 g, 0.84 mmol), and the mixture was stirred at 140 °C for 15 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane and dried with magnesium sulfate. After filtration, the solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound C12 (0.51 g, 0.40 mmol, 74% yield).

[0704] 1 H-NMR (400MHz, CDCl3): δ8.07-8.00(m,2H),7.84(dd,J=7.2Hz,12.8Hz,2H),7.69(s,1H),7.63-7.50(m,4H),7.43-7.19(m,11H),7.16-6.69(m,7H).

[0705] ASAP MS spectral analysis: C 85 H 27 D 21 N 10 O2: Theoretical value 1261.53, observed value 1262.77

[0706] (Synthetic Example 13) Synthesis of Compound C13

[0707] Compound C13

[0708] [Chemical Formula 82]

[0709]

[0710] Under a nitrogen stream, potassium carbonate (0.45 g, 3.23 mmol) was added to an NMP (11 mL) solution of compound t (1.0 g, 1.08 mmol) and 12H-[1]benzothieno[2,3-a]carbazole (0.59 g, 2.16 mmol), and the mixture was stirred at 150 °C for 15 hours. The temperature was then raised to 170 °C and stirred for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in heated ODC B, and purified by column chromatography (toluene:hexane = 1:1) using this solution, yielding a yellow solid C13 (0.35 g, 0.29 mmol, yield 27%).

[0711] 1 H-NMR (400MHz, CDCl3): δ9.73 (s, 1H), 7.93-7.90 (m, 1H), 7.83-7.80 (m, 1H), 7.61 (m, 5H), 7.08 (d, J = 8Hz, 1H), 6.90-6.84 (m, 1H), 6.81-6.75 (m, 1H).

[0712] ASAP MS spectral analysis: C 78 H 11 D 36 N9S: Theoretical value 1177.59, observed value 1178.71

[0713] (Synthetic Example 14) Synthesis of Compound C14

[0714] Compound C14

[0715] [Chemical Formula 83]

[0716]

[0717] Under a nitrogen stream, potassium carbonate (2.41 g, 8.85 mmol) was added to a 90 mL NMP solution of compound m (2 g, 2.95 mmol) and 12H-[1]benzothieno[2,3-a]carbazole (1.60 g, 6.22 mmol), and the mixture was stirred at 150 °C for 15 hours. The reaction solution was cooled to room temperature and quenched with water. The solid was dissolved in heated ODCB, and the solution was purified by column chromatography (toluene:hexane = 1:1) to obtain a yellow compound C14 (1.53 g, 1.57 mmol, yield 53%).

[0718] 1H-NMR(400MHz, CDCl3): δ10.18(s,1H,major rotamer),9.95(s,1H,minorrotamer),8.21-8.15(m,2H),7.97-7.91(m,7H),7.81-7.77(m,1H),7.54-7.29(m,8H),7.22-7.17(m,2H).

[0719] ASAP MS spectral analysis: C 78 H 21 D 25 N8S2: Theoretical value 1183.49, observed value 1184.75

[0720] (Synthetic Example 15) Compare the synthesis of compound A

[0721] compound z

[0722] [Chemical Formula 84]

[0723]

[0724] Under a nitrogen stream, potassium carbonate (0.84 g, 6.10 mmol) was added to a 90 mL NMP solution of compound e (1.50 g, 2.44 mmol) and 9H-carbazole (0.81 g, 4.88 mmol), and the mixture was stirred at 150 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow compound z (1.27 g, 1.39 mmol, yield 57%).

[0725] 1 H-NMR (400MHz, CDCl3): δ9.51 (d, J = 1.6Hz, 1H), 8.03 (d, J = 8.0Hz, 4H), 7.40-7.37 (m, 8H), 7.28-7.23 (m, 4H).

[0726] ASAP MS spectral analysis: C 60 H 17 D 20 FN8: Theoretical value 908.4, observed value 909.75

[0727] Compare compound A

[0728] [Chemical Formula 85]

[0729]

[0730] Under a nitrogen stream, potassium carbonate (0.31 g, 2.26 mmol) was added to a 50 mL NMP solution of compound z (1.03 g, 1.13 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.29 g, 1.69 mmol), and the mixture was stirred at 130 °C for 3 hours. The reaction solution was cooled to room temperature and quenched with water. The solution was filtered, and the solid remaining in the funnel was washed with water. The solid was dissolved in dichloromethane and dried with magnesium sulfate. The solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (toluene:hexane = 1:1) to give a yellow comparative compound A (0.78 g, 0.73 mmol, 65% yield).

[0731] 1 H-NMR (400MHz, CDCl3): δ9.40 (d, J = 4.8Hz, 1H), 7.57 (dd, J = 4.8Hz, 1.2Hz, 4H), 7.28-7.24 (m, 4H), 6.98-6.94 (m, 8H).

[0732] ASAP MS spectral analysis: C 72 H 17 D 28 N9: Theoretical value 1063.5, observed value 1063.7

[0733] (Example 1) Fabrication and evaluation of organic electroluminescent devices

[0734] Vacuum deposition was performed using a vacuum evaporation method at a vacuum level of 5.0 × 10⁻⁶. -5Pa stacked the thin films onto a glass substrate with an anode consisting of an indium tin oxide (ITO) film with a thickness of 50 nm. First, HAT-CN was formed on the ITO with a thickness of 10 nm, NPD was formed on it with a thickness of 30 nm, TrisPCz was formed on it with a thickness of 10 nm, and H1 was formed on it with a thickness of 5 nm. Next, H1, compound C1, and dopant EM1 were co-deposited from different evaporation sources to form a 40 nm thick layer as the light-emitting layer. The concentrations of H1, compound C1, and EM1 in the light-emitting layer were set to 44.2% by mass, 55.0% by mass, and 0.8% by mass. Then, SF3-TRZ was formed with a thickness of 10 nm, and Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively. In addition, Liq is formed with a thickness of 2 nm, followed by aluminum (Al) vapor deposition with a thickness of 100 nm to form a cathode, which is then used as an organic electroluminescent element.

[0735] The results, obtained by driving an organic electroluminescent element made using compound C1, confirmed green delayed fluorescence. Measurements were taken at 6.3 mA / cm². 2 The voltage during driving was 3.82V. Furthermore, the voltage was measured at 6.3mA / cm. 2 The external quantum efficiency (EQE) results during driving show a high value of 24.7%. These results indicate that the organic light-emitting element using the compound represented by general formula (1) has excellent light-emitting properties.

[0736] (Example 2) Fabrication and Evaluation of Organic Electroluminescent Element

[0737] Instead of the light-emitting layer of the organic electroluminescent element in Example 1, H2, compound C1, and dopant EM1 were co-deposited from different evaporation sources to form a 40 nm thick light-emitting layer with a concentration of 64.2% by mass of H2, 35.0% by mass of compound C1, and 0.8% by mass of EM1. Otherwise, the organic electroluminescent element was fabricated following the same steps as in Example 1.

[0738] Furthermore, instead of the light-emitting layer forming the organic electroluminescent element of Example 1, H2, compound C3, and dopant EM1 were co-deposited from different evaporation sources to form a 40 nm thick light-emitting layer with a concentration of 74.2% by mass of H2, a concentration of 25.0% by mass of compound C3, and a concentration of 0.8% by mass of EM1. Otherwise, the organic electroluminescent element was fabricated according to the same steps as in Example 1. Furthermore, compounds C4, C5, C12, C14, and comparative compound A were used instead of compound C3, and the organic electroluminescent element was fabricated in the same manner.

[0739] These components are connected at 25.2 mA / cm 2 The light was driven, and the time from the start of driving until the luminous intensity reached 95% (LT95) was measured. The results are shown in Table 9 as relative values ​​with LT95 of the organic light-emitting element using Comparative Compound A set to 1. The results in Table 9 show that the organic light-emitting element using the compound represented by general formula (1) has a long and excellent lifetime.

[0740] [Table 9]

[0741] The compounds used Lifespan (relative value) Compound C1 12.7 Compound C3 10.4 Compound C4 11.6 Compound C5 10.9 Compound C12 14.5 Compound C14 9.5 Compare compound A 1

[0742] [Chemical Formula 86]

[0743]

[0744] Industrial availability

[0745] Organic light-emitting elements using compounds represented by general formula (1) exhibit excellent light-emitting characteristics. Therefore, the present invention has high industrial applicability.

Claims

1. An organic light-emitting element comprising, in the same layer, a compound represented by the following general formula (1) and a host material or dopant material, [Chemical Formula 1] General formula (1) In general formula (1), R 1 ~R 5 Each of the following groups independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the following general formula (2), and R 2 or R 3 For the group represented by the following general formula (2), R 1 ~R 5 Two or more of them are donor groups, Ar 1 and Ar 2 Each can be used independently to represent either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. [Chemical Formula 2] General formula (2) In general formula (2), X 1 ~X 3 Let N or C(R) represent them independently, but X 1 ~X 3 At least one of them is N, R represents a hydrogen atom, a deuterium atom, or a substituent, and Ar is... 3 and Ar 4 Each independently represents either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, L 1 This indicates a single bond or a divalent linker; * indicates the bonding position. in, The compound represented by the general formula (1) is R 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings, or Ar 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups, or R 1 ~R 5 and Ar 1 ~Ar 4 These two conditions must be met, except for nitrogen-containing 6-membered ring groups in the heteroaryl group.

2. The organic light-emitting element according to claim 1, wherein, R in the general formula (1) 1 ~R 5 One or more of them are donor groups with a fused ring structure of 4 or more rings.

3. The organic light-emitting element according to claim 2, wherein, R in the general formula (1) 1 ~R 5 One or more of them are donor groups represented by the following general formula (3). [Chemical Formula 3] General formula (3) In general formula (3), X represents O, S or NR. 14 R 11 ~R 13 Each can be used independently to represent a deuterium atom or a substituent, R 14 R represents an aryl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium, alkyl, and aryl, or an alkyl group that can be substituted by one or more atoms or groups selected from the group consisting of deuterium and aryl. 11 Each other, R 12 Each other, R 13 They can be bonded to each other to form a ring structure. n11 and n13 represent any integer from 0 to 4, and n12 represents any integer from 0 to 2.

4. The organic light-emitting element according to claim 2, wherein, Ar of the general formulas (1) and (2) 1 ~Ar 4 Each aryl group can be independently substituted or unsubstituted.

5. The organic light-emitting element according to claim 1, wherein, Ar of the general formulas (1) and (2) 1 ~Ar 4 One or more of them are substituted or unsubstituted heteroaryl groups, except for nitrogen-containing 6-membered ring groups.

6. The organic light-emitting element according to claim 5, wherein, Ar of the general formulas (1) and (2) 1 ~Ar 4 One or more of them are heteroaryl groups with a 5-membered ring bonded by a nitrogen atom.

7. The organic light-emitting element according to claim 1, wherein, R in the general formula (1) 2 The group represented by the general formula (2) is called the group.

8. The organic light-emitting element according to claim 1, wherein, R in the general formula (1) 3 The group represented by the general formula (2) is called the group.

9. The organic light-emitting element according to claim 1, wherein, The donor group is a substituted or unsubstituted carbazole-9-yl group.

10. The organic light-emitting element according to claim 1, wherein, R in the general formula (1) 1 ~R 5 Three of them are donor groups.

11. The organic light-emitting element according to claim 1, wherein, X of the general formula (2) 1 ~X 3 Let N be the number of elements in the array.

12. The organic light-emitting element according to claim 1, wherein, L in general formula (2) 1 It is a single key.

13. The organic light-emitting element according to claim 1, wherein, R in the general formula (1) 1 It is a hydrogen atom.

14. The organic light-emitting element according to claim 1, wherein, The compound has at least one deuterium atom.

15. The organic light-emitting element according to any one of claims 1 to 14, wherein, The layer contains the doped material.

16. The organic light-emitting element according to claim 15, wherein, The amount of light emitted from the doped material is greater than the amount of light emitted from the compound.

17. The organic light-emitting element according to claim 15, wherein, The doped material is a compound represented by the following general formula (4). [Chemical Formula 4] General formula (4) In general formula (4), X 1 and X 2 One of them is a nitrogen atom and the other is a boron atom, R 1 ~R 26 A 1 A 2 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 7 and R 8 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 17 and R 18 R 18 and R 19 R 19 and R 20 R 20 and R 21 R 21 and R 22 R 22 and R 23 R 23 and R 24 R 24 and R 25 R 25 and R 26 They can bond together to form a ring structure, wherein, in X 1 When R is a nitrogen atom, 17 and R 18 They bond together to form single bonds to form a pyrrole ring, in X 2 When R is a nitrogen atom, 21 and R 22 They bond together to form single bonds to form a pyrrole ring, wherein, in X 1 For nitrogen atoms, R 7 and R 8 and R 21 and R 22 A six-membered ring is formed through nitrogen atom bonding, R 17 and R 18 When they bond together to form a single bond, R 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 Any one of them bonds with each other to form an aromatic ring or a heteroaromatic ring, and, in X 1 For boron atoms, X 2 For nitrogen atoms, R 7 and R 8 R 17 and R 18 When they bond together to form a ring structure containing boron atoms, this ring structure is a 5- to 7-membered ring. In the case of a 6-membered ring, R 7 and R 8 R 17 and R 18 They bond together to form -B(R) 32 -, -CO-, -CS- or -N(R) 27 )-, R 27 It represents a hydrogen atom, a deuterium atom, or a substituent.

18. The organic light-emitting element according to any one of claims 1 to 14, wherein, The layer contains the main material.

19. The organic light-emitting element according to claim 18, wherein, The material contained in the layer contains the material from which the compound emits the most light.

20. The organic light-emitting element according to claim 18, wherein, The main material is a compound represented by the following general formula (5). [Chemical Formula 5] General formula (5) General formula (5) In general formula (5), X 11 Represents O, S, N(R) A ) or C(R B (R) C A 11 and A 12 Each ring is independently a benzene ring, furan ring, thiol ring, pyrrole ring, or cyclopentadiene ring. These rings can be further fused with other rings or substituted. 111 ~R 114 R B R C Each of the following groups 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; R 115 Each of these 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 with L, R. 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, R 111 and R 112 R 112 and R 113 R 113 and R 114 2 adjacent R 115 R B and R C They can bond together to form a ring structure, where n represents any integer from 3 or 4, and L represents a single bond, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a linking group consisting of two or more of these.

21. The organic light-emitting element according to any one of claims 1 to 14, wherein it emits delayed fluorescence.

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