Compound, light-emitting material, and light-emitting element

Abstract

A compound of the following general formula is used in an organic light-emitting element. X1 to X3 represent N or C (R); r represents H, D or a substituent; x4 represents N or C (R1), X5 represents N or C (R2), X6 represents N or C (R3), and only one of X4 to X6 is N; r1-R5 are H, D, a cyano group, an alkyl group, an aryl group or a donor group, one or more of R1-R5 are cyano groups, and one or more of R1-R5 are donor groups; one or more of Ar1 and Ar2 are heteroaryl groups bonded via N; and L1 represents a single bond or a linking group.

Description

Technical Field

[0001] The present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same. Background Art

[0002] Research is actively underway to improve the luminous efficiency of light-emitting devices such as organic electroluminescent (OLED) elements. In particular, efforts are underway to enhance luminous efficiency through the development and combination of new electron-transporting materials, hole-transporting materials, and luminescent materials that make up OLED elements. Among these efforts, research is also underway into OLED elements utilizing delayed fluorescence materials.

[0003] Delayed fluorescence materials are materials that, after undergoing reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state, emit fluorescence when returning from this excited singlet state to the ground state. The fluorescence generated by this pathway is observed later than fluorescence from an excited singlet state generated directly from the ground state (normal fluorescence), and is therefore called delayed fluorescence. For example, when a luminescent compound is excited by carrier injection, the probability of generating an excited singlet state is statistically 25%:75% for an excited triplet state. Therefore, if only fluorescence from the directly generated excited singlet state is used, there is a limit to improving the luminous efficiency. On the other hand, in delayed fluorescence materials, in addition to the excited singlet state, the excited triplet state can also be used for fluorescence via the aforementioned reverse intersystem crossing pathway, resulting in higher luminous efficiency than conventional fluorescent materials.

[0004] After this principle was clarified, various delayed fluorescence materials were discovered through extensive research. These include compounds in which multiple aromatic rings are substituted with donor and acceptor groups. For example, a compound with the following skeleton was proposed, in which a pyridine ring is substituted with a carbazole-9-yl group as a donor group and a substituted triazine group as an acceptor group (see Patent Document 1).

[0005] [Chemical Formula 1]

[0006]

[0007] Previous technical literature

[0008] Patent Literature

[0009] Patent Document 1: WO2021 / 157600 Summary of the Invention

[0010] Technical issues to be solved by the invention

[0011] To date, no material has been provided that, even for delayed fluorescence, exhibits excellent properties and poses no practical problems. For example, Patent Document 1 describes a delayed fluorescence material having a short delayed fluorescence lifetime and exhibiting excellent luminescence properties. However, there is a desire to provide a delayed fluorescence material with an even shorter delayed fluorescence lifetime. Long delayed fluorescence lifetimes can lead to device degradation or reduced luminous efficiency at high brightness. Therefore, in order to achieve long-life organic electroluminescent devices, it is necessary to develop delayed fluorescence materials with even shorter delayed fluorescence lifetimes. However, improvements in delayed fluorescence materials are still in the experimental stage, and standardizing the chemical structures of useful luminescent materials is not easy.

[0012] Under such circumstances, the present inventors have conducted extensive research with the goal of providing a compound more useful as a delayed fluorescence material for a light-emitting device. Furthermore, they have conducted intensive research with the goal of deriving a general formula for a compound more useful as a delayed fluorescence material and generalizing it.

[0013] Means for solving technical problems

[0014] As a result of intensive research to achieve the above-mentioned object, the present inventors have discovered that a compound having a structure satisfying specific conditions is useful as a light-emitting material. The present invention is based on this finding and specifically has the following structure.

[0015] [1] A compound represented by the following general formula (1).

[0016] [Chemical Formula 2]

[0017] General formula (1)

[0018]

[0019] [In general formula (1), X 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of them is N. R represents a hydrogen atom, a deuterium atom or a substituent. 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom, but Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. 1 represents a single bond or a divalent linking group. 4 Indicates N or C(R 1 ), X 5 Indicates N or C(R 2 ), X6 Indicates N or C(R 3 ), but X 4 ~X 6 Only one of them is N. 1 ~R 5 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. 1 ~R 5 At least one of them is a donor group, R 1 ~R 5 0 to 2 of them are hydrogen atoms or deuterium atoms, R 1 ~R 5 0 to 1 of them are substituted or unsubstituted aryl groups.]

[0020] [2] The compound according to [1], wherein X 5 is N.

[0021] [3] The compound according to [1], wherein X 6 is N.

[0022] [4] The compound according to any one of [1] to [3], wherein R 1 ~R 5 Only one of them is a substituted or unsubstituted aryl group.

[0023] [5] The compound according to [4], wherein R 4 is a substituted or unsubstituted aryl group.

[0024] [6] The compound according to any one of [1] to [5], wherein R 1 ~R 5 One of them is a donor group.

[0025] [7] The compound according to any one of [1] to [5], wherein R 1 ~R 5 Two of them are donor groups.

[0026] [8] The compound according to any one of [1] to [5], wherein R 1 ~R 5 Three of them are donor groups.

[0027] [9] The compound according to any one of [1] to [8], wherein the donor group is a substituted or unsubstituted carbazole-9-yl group.

[0028]

[10] The compound according to [2] or any one of [4] to [9] cited from [2], wherein R 3~R 5 are each independently a substituted or unsubstituted aryl group or a donor group.

[0029]

[11] The compound according to [3] or any one of [4] to [9] referring to [3], wherein R 2 、R 4 and R 5 are each independently a substituted or unsubstituted aryl group or a donor group.

[0030]

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

[11] , wherein X 1 ~X 3 is N.

[0031]

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

[12] , wherein Ar 1 is a substituted or unsubstituted carbazole-9-yl group, Ar 2 is a substituted or unsubstituted aryl group.

[0032]

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

[12] , wherein Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted carbazol-9-yl group.

[0033]

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

[14] , wherein L 1 For a single bond.

[0034]

[16] The compound according to [2] or any one of [4] to

[15] cited from [2], wherein R 1 A hydrogen atom.

[0035]

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

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

[0036]

[18] A light-emitting material consisting of the compound described in any one of [1] to

[17] .

[0037]

[19] A delayed phosphor consisting of the compound described in any one of [1] to

[17] .

[0038]

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

[17] .

[0039]

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

[17] .

[0040]

[22] An organic light-emitting element comprising the compound described in any one of [1] to

[17] .

[0041]

[23] The organic light-emitting element according to

[22] , comprising a layer containing the compound, and the layer further containing a host material.

[0042]

[24] The organic light-emitting element according to

[23] , wherein the layer containing the compound further contains a delayed fluorescent material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

[0043]

[25] The organic light-emitting element according to

[23] or

[24] , comprising a layer containing the compound, and further comprising a light-emitting material having a structure different from that of the compound.

[0044]

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

[23] to

[25] , wherein the amount of light emitted from the compound is the largest among the materials contained in the organic light-emitting element.

[0045]

[27] The organic light-emitting element according to

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

[0046]

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

[22] to

[27] , which is an organic electroluminescent element.

[0047]

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

[22] to

[28] , which emits delayed fluorescence.

[0048] Effects of the Invention

[0049] The compound of the present invention exhibits excellent light-emitting properties and is useful as a material for an organic light-emitting device. DETAILED DESCRIPTION

[0050] The content of the present invention is described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this specification, the numerical range represented by "~" represents a range that includes the numerical values ​​described before and after "~" as the lower limit and upper limit. In addition, part or all of the hydrogen atoms in the molecules of the compounds used in the present invention can be replaced by deuterium atoms ( 2H, deuterium (D). In the chemical structural formulas of this specification, hydrogen atoms are represented by H or omitted. For example, when an atom bonded to a carbon atom constituting the ring backbone of a benzene ring is omitted, H is bonded to a carbon atom of the ring backbone at the omitted position. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom and a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0051] [Compound represented by general formula (1)]

[0052] The compound represented by the following general formula (1) will be described.

[0053] [Chemical Formula 3]

[0054] General formula (1)

[0055]

[0056] In the general formula (1), X 1 ~X 3 Each independently represents N or C(R). 1 ~X 3 At least one of them is N. R represents a hydrogen atom, a deuterium atom or a substituent. The substituent 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 present invention, X 1 ~X 3 is N. In one embodiment of the present invention, X 1 and X 3 N, X 2 In one embodiment of the present invention, X 1 and X 2 N, X 3 In one embodiment of the present invention, X 1 N, X 2 and X 3 In one embodiment of the present invention, X 2 N, X 1 and X 3 is C(R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, R is an aryl group which may be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0057] In the general formula (1), X 4 Indicates N or C(R 1), X 5 Indicates N or C(R 2 ), X 6 Indicates N or C(R 3 ), but X 4 ~X 6 Only one of them is N. In a preferred embodiment of the present invention, X 5 N, X 4 C(R 1 ), X 6 C(R 3 In another preferred embodiment of the present invention, X 6 N, X 4 C(R 1 ), X 5 C(R 2 ). In one embodiment of the present invention, X 4 N, X 5 C(R 2 ), X 6 C(R 3 ).

[0058] In the general formula (1), R 1 ~R 5 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a donor group. 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom.

[0059] R 1 ~R 5 The alkyl group that can be used can be any of linear, branched, and cyclic. Furthermore, two or more of the linear, cyclic, and branched moieties can be present in combination. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Furthermore, 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 the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group of the substituent can be further substituted by, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the substituent of the alkyl group is one or more selected from the group consisting of aryl groups and deuterium atoms. In a preferred embodiment of the present invention, the alkyl group is unsubstituted and can be selected from the group consisting of, for example, methyl, ethyl, isopropyl, and tert-butyl groups.

[0060] R 1 ~R 5 、Ar 1 and Ar 2 The aryl group that can be used can be a single ring or a condensed ring formed by condensing two or more rings. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, for example, it can be selected from 2 to 4. Specific examples of rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituents of the aryl group can be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituents of the aryl group are at least one selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one embodiment of the present invention, the aryl group is unsubstituted.

[0061] Below, we give R 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 the present invention are not limited to the following specific examples. In the following specific examples, * indicates the bonding position. Methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[0062] [Chemical Formula 4]

[0063]

[0064]

[0065] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar20 are substituted with deuterium atoms are exemplified here as Ar40 to Ar59 in order.

[0066] In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is Ar1 or Ar40. In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to Ar50. 1 ~R5 The aryl group that can be used is selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar21 to Ar59.

[0067] In one embodiment of the present invention, Ar 1 and Ar 2 The aryl group that can be used is Ar1 or Ar40. In one embodiment of the present invention, Ar 1 and Ar 2 The aryl group that can be used is selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to Ar50. 1 and Ar 2 The aryl group that can be used is selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. 1 and Ar 2 The aryl group that can be used is selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. 1 and Ar 2 The aryl group that can be used is selected from the group consisting of Ar21 to Ar59.

[0068] R in general formula (1) 1 ~R 5 At least one of them is a donor group. 1 ~R 5 Donor groups that may be employed do not include substituted or unsubstituted aryl groups.

[0069] The "donor group" can be selected from groups with negative Hammett's σp values. The Hammett σp value, proposed by L.P. Hammett, quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it represents the following equation between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0070] log(k / k0)=ρσp

[0071] or

[0072] log(K / K0)=ρσp

[0073] The constant (σp) specific to the substituent in . In the above formula, k0 represents the rate constant of an unsubstituted benzene derivative, k represents the rate constant of a substituted benzene derivative, K0 represents the equilibrium constant of an unsubstituted benzene derivative, K represents the equilibrium constant of a substituted benzene derivative, and ρ represents a reaction constant determined by the type and conditions of the reaction. For the description of the "Hamimett's σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165–195 (1991).

[0074] 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 further 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.

[0075] The donor group in the present invention is preferably a group containing a substituted amino group. It can be a substituted amino group, or an aryl group formed by bonding a substituted amino group, particularly a phenyl group formed by bonding a substituted amino group. In a preferred embodiment of the present invention, the donor group is a substituted amino group.

[0076] The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group described herein may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0077] R 1 ~R 5 The donor group that can be used is preferably a group represented by the following general formula (a).

[0078] [Chemical Formula 5]

[0079] General formula (a)

[0080]

[0081] In general formula (a), Z 1 Indicates CR 14 or N, Z 2 Indicates CR 15 or N, Z3 Indicates CR 16 or N, Z 4 Indicates CR 17 or N. Z 5 Indicates C or N, Ar 5 R represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 14 and R 15 、R 15 and R 16 、R 16 and R 17 They may be bonded to each other to form a ring structure.

[0082] Z 1 ~Z 4 The number of N in is preferably 0 to 3, more preferably 0 to 2. In one embodiment of the present invention, Z 1 ~Z 4 The number of N in is 1. In one embodiment of the present invention, Z 1 ~Z 4 The number of N in is 0.

[0083] R 14 ~R 17 Each independently represents a hydrogen atom, a deuterium atom or a substituent.

[0084] The substituents may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. 14 ~R 17 When two or more of R represent substituents, these two or more substituents may be the same or different. 14 ~R 17 0 to 2 of them are preferably substituents, for example, 1 or 0 of them may be substituents (R 14 ~R 17 is a hydrogen atom or a deuterium atom).

[0085] R 14 and R 15 、R 15 and R 16 、R 16 and R 17They can be bonded to each other to form a cyclic structure. The cyclic structure can be any one of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, and can also be a ring formed by condensing these. Preferably, it is an aromatic ring or a heteroaromatic ring. As the aromatic ring, a substituted or unsubstituted benzene ring can be mentioned. The benzene ring can be further fused with other benzene rings, or with a heterocyclic ring such as a pyridine ring. The heteroaromatic ring means a ring containing a heteroatom as a constituent atom of the ring skeleton and showing aromaticity, preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring can be used. In one embodiment of the present invention, as the heteroaromatic ring, a furan ring, a thiophene ring, or a pyrrole ring can be used. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole described herein may be unsubstituted, substituted with a substituent selected from Substituent Group A, substituted with a substituent selected from Substituent Group B, substituted with a substituent selected from Substituent Group C, substituted with a substituent selected from Substituent Group D, or substituted with a substituent selected from Substituent Group E. Preferably, a substituted or unsubstituted aryl group is bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of such substituents include substituents selected from any one of Substituent Groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one embodiment of the present invention, R 14 and R 15 、R 15 and R 16 、R 16 and R 17 In one embodiment of the present invention, R 14 and R 15 、R 15 and R 16 、R 16 and R 17 They are not bonded to each other to form a ring structure.

[0086] In general formula (a), Z 5 Indicates C or N, Ar 5 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 5 C, Ar 5 is a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 5 N, Ar 5 is a substituted or unsubstituted heteroaromatic ring.

[0087] As Ar 5Examples of the aromatic ring that can be used include a benzene ring. The benzene ring may be fused with another benzene ring or with a heterocyclic ring such as a pyridine ring. 5 The heteroaromatic ring that can be used is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring. In one embodiment of the present invention, as the heteroaromatic ring, 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 can be used. In one embodiment of the present invention, Z 5 is C, and the heteroaromatic ring is a substituted or unsubstituted furan ring of benzofuran, a substituted or unsubstituted thiophene ring of benzothiophene, a substituted or unsubstituted pyridine ring of quinoline, or a substituted or unsubstituted pyridine ring of isoquinoline. In one embodiment of the present invention, Z 5 is N, and the heteroaromatic ring is a substituted or unsubstituted pyrrole ring of indole or an imidazole ring of benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole described herein may be unsubstituted, substituted with a substituent selected from Substituent Group A, substituted with a substituent selected from Substituent Group B, substituted with a substituent selected from Substituent Group C, substituted with a substituent selected from Substituent Group D, or substituted with a substituent selected from Substituent Group E.

[0088] In the general formula (a), Z 5 When it is C, it is preferably a group represented by the following general formula (b).

[0089] [Chemical Formula 6]

[0090] General formula (b)

[0091]

[0092] In the general formula (b), Z 1 Indicates CR 14 or N, Z 2 Indicates CR 15 or N, Z 3 Indicates CR 16 or N, Z 4 Indicates CR 17 or N, Z 6 Indicates CR 18 or N, Z 7 Indicates CR 19 or N, Z 8 Indicates CR 20 or N, Z 9 Indicates CR 21 or N. R 14 and R 15 、R 15 and R16 、R 16 and R 17 、R 18 and R 19 、R 19 and R 20 、R 20 and R 21 They may be bonded to each other to form a ring structure.

[0093] Regarding Z in general formula (b) 1 ~Z 4 、R 14 ~R 17 , can refer to the corresponding description of general formula (a). Z in general formula (b) 6 ~Z 9 、R 18 ~R 21 Sequentially with Z of general formula (a) 1 ~Z 4 、R 14 ~R 17 Correspondingly, regarding these contents, reference can be made to Z in the general formula (a). 1 ~Z 4 、R 14 ~R 17 Description.

[0094] In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of N in is preferably 0 to 2, more preferably 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of N in is 1. In a preferred embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of N in is 0. When the number of N is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0095] 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 described herein may be unsubstituted, substituted with a substituent selected from Substituent Group A, substituted with a substituent selected from Substituent Group B, substituted with a substituent selected from Substituent Group C, substituted with a substituent selected from Substituent Group D, or substituted with a substituent selected from Substituent Group E. Furthermore, one or more rings may be further fused to the two benzene rings constituting the carbazole-9-yl group. In a preferred embodiment of the present invention, R 1 ~R 5 The donor group that can be used is a carbazole-9-yl group that may be substituted with a group selected from Substituent Group E and may be fused with one or more rings. When the carbazole-9-yl group not fused with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one of positions 2 to 7, more preferably at least one of positions 3 or 6, and even more preferably positions 3 and 6.

[0096] In one embodiment of the present 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 is hereinafter referred to as a "ring-fused carbazole-9-yl group". 1 ~R 5 The ring-fused carbazole-9-yl group that can be used may be unsubstituted, substituted with a substituent selected from Substituent Group A, substituted with a substituent selected from Substituent Group B, substituted with a substituent selected from Substituent Group C, substituted with a substituent selected from Substituent Group D, or substituted with a 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 present invention, the ring-fused carbazole-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazole-9-yl group is substituted with an aryl group that may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a combination of two or more atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.

[0097] The total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. The number of rings mentioned herein includes the number of fused carbazole rings (i.e., 3).

[0098] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any one of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may also be a ring formed by further condensing these. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocycle. As the aromatic hydrocarbon ring, a substituted or unsubstituted benzene ring may be mentioned. The benzene ring may be further fused with another benzene ring, or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring containing a heteroatom as a constituent atom of the ring skeleton and showing aromaticity, and is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring may be used. In one embodiment of the present invention, as the aromatic heterocycle, a furan ring, a thiophene ring, or a pyrrole ring may be used. In one embodiment of the present 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. In addition, a substituent selected from the substituent group E is preferably bonded to the nitrogen atom of the pyrrole ring (except for the case of only a deuterium atom), and more preferably an aryl group that can be substituted by an alkyl or aryl group is bonded. In the present invention, it is preferred to use a carbazole-9-yl ring fused with one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton constituent atoms. Among them, it is preferred to use a carbazole-9-yl formed by the fusion of a benzofuran structure, a carbazole-9-yl formed by the fusion of a benzothiophene structure, or a carbazole-9-yl formed by the fusion of an indole structure. In one embodiment of the present invention, there is a carbazole-9-yl formed by the fusion of at least one benzofuran structure, for example, there are more than two. In one embodiment of the present invention, the compound has at least one carbazole-9-yl group condensed with a benzothieno structure, for example, two or more.

[0099] Examples of the ring-fused carbazole-9-yl group include benzofurano[2,3-a]carbazole-9-yl, benzofurano[3,2-a]carbazole-9-yl, benzofurano[2,3-b]carbazole-9-yl, benzofurano[3,2-b]carbazole-9-yl, benzofurano[2,3-c]carbazole-9-yl, and benzofurano[3,2-c]carbazole-9-yl. Furthermore, as the ring-fused carbazole-9-yl group, benzothieno[2,3-a]carbazole-9-yl, benzothieno[3,2-a]carbazole-9-yl, benzothieno[2,3-b]carbazole-9-yl, benzothieno[3,2-b]carbazole-9-yl, benzothieno[2,3-c]carbazole-9-yl, and benzothieno[3,2-c]carbazole-9-yl can also be used. Furthermore, as the ring-fused carbazole-9-yl group, indolo[2,3-a]carbazole-9-yl, indolo[3,2-a]carbazole-9-yl, indolo[2,3-b]carbazole-9-yl, indolo[3,2-b]carbazole-9-yl, indolo[2,3-c]carbazole-9-yl, and indolo[3,2-c]carbazole-9-yl can also be used.

[0100] When the ring-fused carbazole-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and further preferably 1 to 4, for example, it may be 1, for example, it may also be 2. In a preferred embodiment of the present invention, any one of the 3-position or 6-position of the ring-fused carbazole-9-yl group is substituted. In a preferred embodiment of the present invention, from the perspective of the heteroatoms present in the ring-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 present invention, from the perspective of the heteroatoms present in the ring-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 present invention, from the perspective of the heteroatoms present in the ring-fused carbazole-9-yl group, there is a substituent at all the para positions of the benzene ring that can be substituted.

[0101] Hereinafter, R of the general formula (1) is shown. 1 ~R 5 Specific examples of usable donor groups. The donor groups that can be used in the present invention are not limited to the following specific examples. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents a bonding position. Methyl groups are omitted, so for example, D2 has one methyl group. Deuterated methyl groups are represented as CD3. Furthermore, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0102] [Chemical Formula 7]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[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] Compounds in which all hydrogen atoms present in the above-mentioned D1 to D459 are substituted with deuterium atoms are disclosed as D717 to D1175. Phenyl groups bonded to the 3-position of D1 to D1175 (i.e., groups in which a m-phenylene group is further bonded to * in D1 to D1175) are disclosed as D1(m) to D1175(m). Phenyl groups bonded to the 4-position of D1 to D1175 (i.e., groups in which a p-phenylene group is further bonded to * in D1 to D1175) are disclosed as D1(p) to D1175(p).

[0145] In a preferred embodiment of the present invention, R 1 ~R 5 The donor group that can be used is selected from the group consisting of D1 to D1175. 1 ~R 5 The donor group that can be used is selected from the group consisting of D460 to D1175. 1 ~R 5 The donor group that can be used is selected from the group consisting of D1(m) to D1175(m). In one embodiment of the present invention, R 1 ~R 5The donor group that can be used is selected from the group consisting of D1(p) to D1175(p).

[0146] In one embodiment of the present invention, R 1 ~R 5 The donor group that can be used is selected from the group consisting of D1 to D13 and D717 to D729. 1 ~R 5 The donor group that can be used is selected from the group consisting of D14 to D16 and D730 to D732. 1 ~R 5 The donor group that can be used is selected from the group consisting of D17 to D87 and D733 to D803. 1 ~R 5 The donor group that can be used is selected from the group consisting of D88 to D123 and D804 to D839. 1 ~R 5 The donor group that can be used is selected from the group consisting of D124 to D189 and D840 to D905. 1 ~R 5 The donor group that can be used is selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, and D1168 to D1175. 1 ~R 5 The donor group that can be used is selected from the group consisting of D364 to D451 and D1080 to D1167. 1 ~R 5 The donor group that can be used is selected from the group consisting of D460 to D716.

[0147] R in general formula (1) 1 ~R 5 In one embodiment of the present invention, R 1 ~R 5 1 to 3 of them are donor groups. In one embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, one, two or three of R 1 ~R 5 In a preferred embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, R 1 ~R 5In one embodiment of the present invention, at least R 1 In one embodiment of the present invention, at least R 3 In one embodiment of the present invention, at least R 4 In one embodiment of the present invention, at least R 5 In one embodiment of the present invention, only R 1 In one embodiment of the present invention, only R 3 In one embodiment of the present invention, only R 4 In one embodiment of the present invention, only R 5 In a preferred embodiment of the present invention, only R 3 and R 5 In a preferred embodiment of the present invention, only R 2 and R 5 In one embodiment of the present invention, only R 2 and R 4 In one embodiment of the present invention, only R 3 and R 4 and R 5 In one embodiment of the present invention, only R 2 and R 4 and R 5 is the donor group. 1 ~R 5 When two or more of the groups are donor groups, they may be the same or different.

[0148] R 1 ~R 5 The number of hydrogen atoms or deuterium atoms in is 0 to 2, preferably 0 or 1, for example 1, for example 0. 1 ~R 5 The compound having three hydrogen atoms or deuterium atoms has more excellent luminescence properties. 1 ~R 5 The number of substituted or unsubstituted aryl groups in R is 0 or 1, preferably 1. It may also be 0. 1 ~R 5 The number of substituted or unsubstituted alkyl groups in the group is 0 to 3, preferably 0 to 2, and may be 1 or 0.

[0149] In a preferred embodiment of the present invention, R 1 ~R 5In one embodiment of the present invention, two of the donor groups are donor groups, one is a substituted or unsubstituted aryl group, and one is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, the two donor groups are the same. In one embodiment of the present invention, the two donor groups are different from each other. In one embodiment of the present invention, X 5 or X 6 N, R 1 In a preferred embodiment of the present invention, X 5 N, R 1 is a hydrogen atom or a deuterium atom, R 3 and R 5 is the donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 is a hydrogen atom or a deuterium atom, R 4 and R 5 is the donor group, R 3 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 is a hydrogen atom or a deuterium atom, R 3 and R 4 is the donor group, R 5 In a preferred embodiment of the present invention, X 6 N, R 1 is a hydrogen atom or a deuterium atom, R 2 and R 5 is the donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 6 N, R 1 is a hydrogen atom or a deuterium atom, R 4 and R 5 is the donor group, R 2 is a substituted or unsubstituted aryl group.

[0150] In one embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, three of the donor groups are the same. In one embodiment of the present invention, two of the three donor groups are the same and one is different. In one embodiment of the present invention, X 5 N, R 1 is a hydrogen atom or a deuterium atom, R 3 ~R 5 In one embodiment of the present invention, X 6 N, R 1 is a hydrogen atom or a deuterium atom, R 2 、R4 and R 5 is a donor group.

[0151] In one embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, X 5 N, R 1 and R 3 is a hydrogen atom or a deuterium atom, R 4 is a substituted or unsubstituted aryl group, R 5 In one embodiment of the present invention, X 5 N, R 1 and R 3 is a hydrogen atom or a deuterium atom, R 4 is the donor group, R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 and R 5 is a hydrogen atom or a deuterium atom, R 3 is the donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 and R 4 is a hydrogen atom or a deuterium atom, R 3 is the donor group, R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 is the donor group, R 3 and R 5 is a hydrogen atom or a deuterium atom, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, X 5 N, R 1 is the donor group, R 3 and R 4 is a hydrogen atom or a deuterium atom, R 5 is a substituted or unsubstituted aryl group.

[0152] In a preferred embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, X 5 N, R 1 and R 4 is a hydrogen atom or a deuterium atom, R 3 and R 5In one embodiment of the present invention, X 5 N, R 1 and R 5 is a hydrogen atom or a deuterium atom, R 3 and R 4 In one embodiment of the present invention, X 5 N, R 1 and R 3 is a hydrogen atom or a deuterium atom, R 4 and R 5 In a preferred embodiment of the present invention, X 6 N, R 1 and R 4 is a hydrogen atom or a deuterium atom, R 2 and R 5 In one embodiment of the present invention, X 6 N, R 1 and R 2 is a hydrogen atom or a deuterium atom, R 4 and R 5 is a donor group.

[0153] In one embodiment of the present invention, R 1 ~R 5 One of them is a donor group, and three of them are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, X 5 N, R 1 、R 3 and R 4 is a hydrogen atom or a deuterium atom, R 5 In one embodiment of the present invention, X 5 N, R 1 、R 3 and R 5 is a hydrogen atom or a deuterium atom, R 4 In one embodiment of the present invention, X 5 N, R 1 、R 4 and R 5 is a hydrogen atom or a deuterium atom, R 3 In one embodiment of the present invention, X 5 N, R 1 is the donor group, R 3 、R 4 and R 5 A hydrogen atom or a deuterium atom.

[0154] In one embodiment of the present invention, R 3 ~R 5 are independently substituted or unsubstituted aryl groups or donor groups.3 ~R 5 In a preferred embodiment of the present invention, two of them are donor groups and one is a substituted or unsubstituted aryl group. 3 and R 5 is the donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 3 、R 4 and R 5 is a donor group.

[0155] In one embodiment of the present invention, R 2 、R 4 and R 5 is a substituted or unsubstituted aryl group or a donor group. In one embodiment of the present invention, R 2 、R 4 and R 5 In a preferred embodiment of the present invention, two of them are donor groups and one is a substituted or unsubstituted aryl group. 2 and R 5 is the donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 、R 4 and R 5 is a donor group.

[0156] Ar in the general formula (1) 1 and Ar 2 The heteroaryl group that can be used can be a monocyclic ring or a condensed ring formed by condensing two or more rings. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, for example, it can be selected from 2 to 4. Specific examples of rings include pyridine rings, pyrimidine rings, and pyrrole rings, and these rings can be further condensed 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 the range of 5 to 12.

[0157] Ar in the general formula (1) 1 and Ar 2At least one of them is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. That is, it is a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a constituent atom of the ring skeleton and is a group bonded via a nitrogen atom that is one of the constituent atoms of the ring skeleton. A typical example of such a group is a substituted or unsubstituted pyrrol-1-yl group, preferably a substituted or unsubstituted fused ring pyrrol-1-yl group, and more preferably a substituted or unsubstituted carbazole-9-yl group, and a ring may be further fused to the carbazole skeleton. As Ar 1 and Ar 2 Specific examples of the substituted or unsubstituted heteroaryl group bonded via a nitrogen atom that can be used in at least one of the above-mentioned groups include D1 to D1175.

[0158] In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D1 to D13 and D717 to D729. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D14 to D16 and D730 to D732. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D17 to D87 and D733 to D803. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D88 to D123 and D804 to D839. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D124 to D189 and D840 to D905. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, and D1168 to D1175. In one embodiment of the present invention, Ar 1 and Ar 2 At least one of the groups used in is selected from the group consisting of D364 to D451 and D1080 to D1167. 1 and Ar 2 At least one group used in is selected from the group consisting of D460 to D716.

[0159] In one embodiment of the present invention, Ar 1 and Ar 2are each independently a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. 1 and Ar 2 is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom and has the same structure. 1 is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group.

[0160] L in the general formula (1) 1 represents a single bond or a divalent linking group. Examples of the divalent linking group include substituted or unsubstituted arylene groups and substituted or unsubstituted heteroarylene groups. In a preferred embodiment of the present invention, L 1 In one embodiment of the present invention, L 1 is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L 1 For the aryl moiety constituting the arylene group, reference can be made to the above R 1 ~R 5 The description and preferred range of the aryl group in the column describing . Examples of the heteroarylene group include a linking group in which at least one of the carbon atoms constituting the ring skeleton of the arylene group is substituted with a nitrogen atom.

[0161] Below, we take L 1 Among them, L that can be used in the present invention 1 The present invention is not to be construed as limiting the scope of these specific examples. In the following specific examples, methyl groups are omitted. Thus, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0162] [Chemical Formula 8]

[0163]

[0164] Compounds in which all hydrogen atoms present in L2 to L21 are replaced by deuterium atoms are disclosed as L22 to L41. 1 is selected from the group consisting of L1 to L7 and L22 to L27. 1 is selected from the group consisting of L2 to L7 and L22 to L27. 1 is selected from the group consisting of L1, L8 to L13, L20, L21, L28 to L33, L40, and L41. 1 is selected from the group consisting of L8 to L13, L20, L21, L28 to L33, L40, and L41.1 is selected from the group consisting of L1, L14 to L19, and L34 to L39. 1 Selected from the group consisting of L14 to L19 and L34 to L39.

[0165] In a preferred embodiment of the present invention, X 1 ~X 3 、X 5 N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, R 1 、R 3 ~R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), one is a substituted or unsubstituted aryl group, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0166] In a preferred embodiment of the present invention, X 1 ~X 3 、X 5 N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group, R 1 、R 3 ~R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), one is a substituted or unsubstituted aryl group, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0167] In one embodiment of the present invention, X 1 ~X 3 、X 5 N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, R 1 、R 3 ~R 5 Three of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0168] In one embodiment of the present invention, X 1 ~X 3 、X 5 N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group, R 1 、R 3 ~R 5 Three of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0169] In one embodiment of the present invention, X 1 ~X 3 、X 6 N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, R 1 、R 2 、R 4 、R 5 2 to 3 of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), 1 to 2 (preferably at least R 1 ) is a hydrogen atom or a deuterium atom, and 0 to 1 of them are substituted or unsubstituted aryl groups.

[0170] In one embodiment of the present invention, X 1 ~X 3 、X 6 N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group, R 1 、R 2 、R 4 、R 5 2 to 3 of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), 1 to 2 (preferably at least R 1 ) is a hydrogen atom or a deuterium atom, and 0 to 1 of them are substituted or unsubstituted aryl groups.

[0171] In a preferred embodiment of the present invention, X 1 ~X 3 、X 6 N, L1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, R 1 、R 2 、R 4 、R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), one is a substituted or unsubstituted aryl group, and one (preferably at least R 1 ) is a hydrogen atom or a deuterium atom.

[0172] In a preferred embodiment of the present invention, X 1 ~X 3 、X 6 N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group, R 1 、R 2 、R 4 、R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), one is a substituted or unsubstituted aryl group, and one (preferably at least R 1 ) is a hydrogen atom or a deuterium atom.

[0173] In a preferred embodiment of the present invention, X 1 ~X 3 、X 6 N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, R 1 、R 2 、R 4 、R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), and two (preferably at least R 1 ) is a hydrogen atom or a deuterium atom.

[0174] In a preferred embodiment of the present invention, X 1 ~X 3 、X 6 N, L 1 is a single bond, Ar 1is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, Ar 2 is a substituted or unsubstituted aryl group, R 1 、R 2 、R 4 、R 5 Two of them are donor groups (preferably substituted or unsubstituted carbazole-9-yl), and two (preferably at least R 1 ) is a hydrogen atom or a deuterium atom.

[0175] The compound represented by the general formula (1) preferably does not contain metal atoms and can be a compound consisting 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 the 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 the general formula (1) can be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms. The compound represented by the general formula (1) can be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms and nitrogen atoms. The compound represented by the general formula (1) can be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms and nitrogen atoms. In addition, the compound represented by the general formula (1) can be a compound containing deuterium atoms but not hydrogen atoms.

[0176] In the present specification, the "substituent group A" refers to a group selected from a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), a The present invention also includes one atom or group selected from the group consisting of a thioaryl group (e.g., a ring skeleton having 5 to 30 atoms), a heteroarylthio group (e.g., a ring skeleton having 5 to 30 atoms), an acyl group (e.g., a ring skeleton having 1 to 40 carbon atoms), an alkenyl group (e.g., a ring skeleton having 1 to 40 carbon atoms), an alkynyl group (e.g., a ring skeleton having 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., a ring skeleton having 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., a ring skeleton having 7 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., a ring skeleton having 5 to 30 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group, or a group obtained by combining two or more of the following:

[0177] In the present specification, "substituent group B" means one atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), or a group obtained by combining two or more of the above.

[0178] In this specification, "substituent group C" means one atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), or a group obtained by combining two or more of them.

[0179] In this specification, the "substituent group D" refers to one atom or group selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), and heteroaryl groups (e.g., having 5 to 20 atoms constituting the ring skeleton), or a group obtained by combining two or more of them.

[0180] In this specification, "substituent group E" means one atom or group selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms), or a group obtained by combining two or more of them.

[0181] In this specification, when a substituent is described as "substituted or unsubstituted" or "may be substituted", it can be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0182] Specific examples of the compound represented by the general formula (1) are shown in Tables 1 to 5 below. However, the compound represented by the general formula (1) that can be used in the present invention should not be construed as being limited to these specific examples.

[0183] In Table 1, R of the following general formula (1a) is determined for each compound. 3 ~R 5 To show the structure of each compound separately. 1 and Ar 2 Deuterated carbazolyl (D717), X 1 ~X 3 is a nitrogen atom (N), L 1 For a single bond, X5 N, R 1 is a hydrogen atom, R 3 ~R 5 The structures of the groups identified in Table 1 are shown individually as the structures of Compounds 1 to 1175.

[0184] [Chemical Formula 9]

[0185] General formula (1a)

[0186]

[0187] In Table 2, the R values ​​of a plurality of compounds are summarized in each column. 3 ~R 5 To show the structures of compounds 1 to 1015655. For example, if it is the section of compounds 1 to 1175 in Table 2, then R 4 Fixed as Ar1, R 3 and R 5 The compounds D1 to D1175 are sequentially referred to as compounds 1 to 1175. 3 and R 5 That is, in the section of compounds 1 to 1175 in Table 2, compounds 1 to 1175 identified in Table 1 are collectively shown in one section. Similarly, in the section of compounds 1176 to 2350 in Table 2, R 4 Fixed as Ar2, R 3 and R 5 The compounds D1 to D1175 were designated as compounds 1176 to 2350. Based on the same principle, compounds 2351 to 1015655 in Table 2 were also identified.

[0188] [Table 1]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] [Table 2]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] Next, specific examples of the compound having a structure represented by the following general formula (1b) are shown in Table 3. In Table 3, the structure of each compound is shown based on the same principle as in Table 2.

[0204] [Chemical Formula 10]

[0205] General formula (1b)

[0206]

[0207] [Table 3]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] Next, specific examples of the compound having a structure represented by the following general formula (1c) are shown in Table 4. In Table 4, the structure of each compound is shown based on the same principle as in Table 2.

[0217] [Chemical Formula 11]

[0218] General formula (1c)

[0219]

[0220] [Table 4]

[0221]

[0222] In Tables 1 to 4, determine Ar of the general formula (1) 1 and Ar 2 The structure of the deuterated carbazolyl group (D717) is used as the structure of compounds 1 to 2101810. In Table 5, Ar 1 and Ar 2 The compounds modified as shown in Table 5 are shown in the table in order. In Table 5, compounds 1 to 2101810 are also shown in the first column for easy understanding of the corresponding relationship. In the second column of Table 5, for example, compound 1 (1) represents a compound having Ar 2 The compound 2 (1) is a compound having a structure in which Ar of the compound 2 is replaced by Ar1. 2 Compound 2031310(1) represents a compound having a structure in which Ar of compound 2101810 is replaced by Ar1. 2 Compounds having a structure substituted with Ar1. Compounds 1(2) to 2101810(2) in the third section of Table 5 or compounds in subsequent sections are also determined by the same principle. In addition, X of the compounds determined in Table 5 1 ~X 3 All are nitrogen atoms (N), L 1 is a single bond, R 1 A hydrogen atom.

[0223] [Table 5]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] The compounds identified by the above numbers are disclosed individually. In addition, when there are rotational isomers in the specific examples of the above compounds, the present specification also discloses mixtures of rotational isomers and each isolated rotational isomer.

[0236] In one embodiment of the present invention, a compound is selected from compound group α consisting of compounds 1 to 2101810 and compounds 1(n) to 2101810(n) [wherein n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [4] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [5] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [6] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [7] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [8] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [9] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above

[10] in compound group α. In one embodiment of the present invention, a compound is selected from compounds satisfying the above

[11] in compound group α. In one embodiment of the present invention, a compound is selected from the compounds in compound group α that satisfy the above

[12] . In one embodiment of the present invention, a compound is selected from the compounds in compound group α that satisfy the above

[13] . In one embodiment of the present invention, a compound is selected from the compounds in compound group α that satisfy the above

[17] .

[0237] In one embodiment of the present invention, a compound is selected from compound group β consisting of compounds 1 to 1015655 and compounds 1(n) to 1015655(n) [wherein n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [4] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [5] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [6] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [7] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [8] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above [9] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above

[10] in compound group β. In one embodiment of the present invention, a compound is selected from compounds satisfying the above

[11] in compound group β. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[12] in compound group β. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[13] in compound group β. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[17] in compound group β.

[0238] In one embodiment of the present invention, a compound is selected from the compound group γ consisting of compounds 1015656 to 2031310 and compounds 1015656(n) to 2031310(n) [wherein n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [4] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [5] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [6] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [7] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [8] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[10] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[11] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[12] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[13] in the compound group γ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[17] in the compound group γ.

[0239] In one embodiment of the present invention, a compound is selected from the compound group δ consisting of compounds 2031311 to 2101810 and compounds 2031311(n) to 2101810(n) [wherein n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [5] in the compound group δ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above [9] in the compound group δ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[13] in the compound group δ. In one embodiment of the present invention, a compound is selected from the compounds satisfying the above

[17] in the compound group δ.

[0240] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following compound group.

[0241] [Chemical Formula 12]

[0242]

[0243]

[0244] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following compound group.

[0245] [Chemical Formula 13]

[0246]

[0247]

[0248] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following compound group.

[0249] [Chemical Formula 14]

[0250]

[0251]

[0252]

[0253] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following compound group.

[0254] [Chemical Formula 15]

[0255]

[0256] The molecular weight of the compound represented by general formula (1), for example, when an organic layer containing the compound represented by general formula (1) is to be formed into a film by a vapor deposition method, 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).

[0257] The compound represented by the general formula (1) can be formed into a film by a coating method regardless of its molecular weight. If a coating method is used, even a compound with a relatively large molecular weight can be formed into a film. The compound represented by the general formula (1) has advantages such as being easily soluble in an organic solvent. Therefore, the compound represented by the general formula (1) is easily applicable to the coating method and is easily purified to increase its purity.

[0258] It is also conceivable to apply the present invention to using a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light-emitting material.

[0259] For example, it is conceivable to use a polymer obtained by pre-existing a polymerizable group in a structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any position in general formula (1), polymerize it alone or copolymerize it with other monomers to obtain a polymer having a repeating unit, and use the polymer as a light-emitting material. Alternatively, it is conceivable to obtain a dimer or trimer by coupling compounds having a structure represented by general formula (1) to each other, and use these as light-emitting materials.

[0260] Examples of polymers having repeating units containing a structure represented by the general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0261] [Chemical Formula 16]

[0262]

[0263] In the above general formula, Q represents a group including a structure represented by general formula (1), L 1 and L 2 The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group preferably has -X 11 -L 11 - a connecting group of a structure represented by. Here, X 11 L represents an oxygen atom or a sulfur atom, preferably an oxygen atom. 11represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

[0264] In the above general formula, R 101 、R 102 、R 103 and R 104 Each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom. More preferably, it is an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom. Even more preferably, it is an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0265] L 1 and L 2 The linking group represented by 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 crosslinked structure or a network structure.

[0266] Specific structural examples of the repeating unit include structures represented by the following formulae.

[0267] [Chemical Formula 17]

[0268]

[0269] A polymer having repeating units of these formulae can be synthesized by introducing a hydroxyl group into any position in the general formula (1), reacting the hydroxyl group with the following compound as a linking group to introduce a polymerizable group, and polymerizing the polymerizable group.

[0270] [Chemical Formula 18]

[0271]

[0272] The polymer containing the structure represented by the general formula (1) in the molecule may be a polymer consisting only of repeating units having the structure represented by the general formula (1), or a polymer containing repeating units having structures other than these. Furthermore, the repeating units having the structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. As repeating units not having the structure represented by the general formula (1), repeating units derived from monomers commonly used for copolymerization may be cited. For example, repeating units derived from monomers having ethylenically unsaturated bonds such as ethylene and styrene may be cited.

[0273] In one embodiment, the compound represented by general formula (1) is a light-emitting material.

[0274] In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence.

[0275] In one embodiment of the present invention, the compound represented by general formula (1) 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 when excited thermally or electronically.

[0276] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the red or orange region (eg, about 620 nm to about 780 nm, about 650 nm) of the visible spectrum when excited thermally or electronically.

[0277] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the orange or yellow region (eg, about 570 nm to about 620 nm, about 590 nm, about 570 nm) of the visible spectrum when excited thermally or electronically.

[0278] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the green region of the visible spectrum (eg, about 490 nm to about 575 nm, about 510 nm) when excited thermally or electronically.

[0279] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the blue region of the visible spectrum (eg, about 400 nm to about 490 nm, about 475 nm) when excited thermally or electronically.

[0280] In one embodiment of the present invention, the compound represented by the general formula (1) can emit light in the ultraviolet spectrum region (eg, 280 to 400 nm) when excited thermally or electronically.

[0281] In one embodiment of the present invention, the compound represented by the general formula (1) can emit light in the infrared spectral region (eg, 780 nm to 2 μm) when excited thermally or electronically.

[0282] In one embodiment of the present invention, an organic semiconductor element using the compound represented by the general formula (1) can be produced. The organic semiconductor element described herein can be an organic optical element in which light is involved, or an organic element in which light is not involved. The organic optical element can be an organic light-emitting element that emits light, or an organic light-receiving element that receives light, or an element that generates energy transfer due to light within the element. In one embodiment of the present invention, the compound represented by the general formula (1) can be used to produce an organic optical element such as an organic electroluminescent element or a solid-state imaging element (such as a CMOS image sensor). In one embodiment of the present invention, a CMOS (complementary metal oxide semiconductor) or the like using the compound represented by the general formula (1) can be produced.

[0283] The electronic properties of a library of small molecule chemical substances can be calculated using well-known ab initio quantum chemical calculations. For example, using a time-dependent density functional theory (TD-DFT / B3LYP / 6-31G*) with a function set known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals as a basis set to analyze the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) allows screening for molecular fragments (parts) with a HOMO above a specific threshold and a LUMO below a specific threshold.

[0284] Thus, for example, when a HOMO energy (e.g., ionization potential) of -6.5 eV or higher is present, the donor moiety ("D") can be selected. Furthermore, when a LUMO energy (e.g., electron affinity) of -0.5 eV or lower is present, the acceptor moiety ("A") can be selected. The bridge moiety ("B") is, for example, a strongly conjugated system that can strictly constrain the acceptor and donor moieties to a unique steric structure, thereby preventing duplication of the π-conjugated systems of the donor and acceptor moieties.

[0285] In one embodiment, a compound library is screened using one or more of the following properties.

[0286] 1. Luminescence near a specific wavelength

[0287] 2. Calculated triplet states above a specific energy level

[0288] 3. ΔE below a specific value ST value

[0289] 4. Quantum yield above a specific value

[0290] 5.HOMO energy level

[0291] 6.LUMO energy level

[0292] In one embodiment, the difference between the lowest excited singlet state and the lowest excited triplet state at 77K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.

[0293] In one embodiment, the compound represented by formula (1) exhibits a quantum yield greater than 25%, for example, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0294] [Method for synthesizing the compound represented by general formula (1)]

[0295] The compound represented by the general formula (1) includes a novel compound.

[0296] The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, a compound having a structure in which a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group (e.g., a phenyl group), and a triazole group substituted by two substituted or unsubstituted carbazolyl groups are bonded to a pyridine ring in the compound represented by the general formula (1) can be synthesized by introducing a triazole group having two substituted or unsubstituted carbazolyl groups into a pyridine derivative having a substituted or unsubstituted aryl group and a halogen atom, and then reacting the triazole group with a substituted or unsubstituted carbazole. For details of the reaction conditions, reference can be made to the synthesis examples described below.

[0297] [Structure using the compound represented by general formula (1)]

[0298] In one embodiment, the compound represented by the general formula (1) is combined to disperse the compound, covalently bond with the compound, coat the compound, support the compound, or use it together with one or more materials associated with the compound (such as small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer. For example, the compound represented by the general formula (1) can be combined with an electroactive material to form a film. In some cases, the compound represented by the general formula (1) can also be combined with a hole transport polymer. In some cases, the compound represented by the general formula (1) can also be combined with an electron transport polymer. In some cases, the compound represented by the general formula (1) can also be combined with a hole transport polymer and an electron transport polymer. In some cases, the compound represented by the general formula (1) can also be combined with a copolymer having both a hole transport portion and an electron transport portion. By the embodiments described above, the electrons and / or holes formed in the solid film or layer can interact with the compound represented by the general formula (1).

[0299] [Film formation]

[0300] In one embodiment, the film comprising the compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution obtained by dissolving the composition comprising the compound of the present invention is applied to the surface, and after removing the solvent, a film is formed. As a wet process, spin coating, slit coating, inkjet method (spraying method), gravure printing, offset printing, flexographic printing method can be cited, but it is not limited to these. In the wet process, an appropriate organic solvent that can dissolve the composition comprising the compound of the present invention is selected. In one embodiment, a substituent (such as an alkyl group) that improves solubility relative to an organic solvent can be introduced into the compound contained in the composition.

[0301] In one embodiment, a film containing the compound of the present invention can be formed by a dry process. In one embodiment, as a dry process, a vacuum evaporation method can be used, but is not limited thereto. In the case of the vacuum evaporation method, the compounds constituting the film can be co-evaporated from a separate evaporation source, or co-evaporated from a single evaporation source in which the compounds are mixed. In the case of using a single evaporation source, a mixed powder obtained by mixing the powders of the compounds can be used, a compressed molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating, melting and cooling each compound can be used. In one embodiment, by co-evaporating under conditions where the evaporation rates (weight reduction rates) of the multiple compounds contained in a single evaporation source are consistent or approximately 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 a plurality of compounds are mixed in a composition ratio identical to the composition ratio of the formed film and used as a evaporation source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-evaporated compound becomes the same weight reduction rate can be determined, and this temperature is used as the temperature during co-evaporation.

[0302] [Examples of Use of the Compound Represented by General Formula (1)]

[0303] The compound represented by the general formula (1) is useful as a material for an organic light-emitting device, and is particularly preferably used in an organic light-emitting diode or the like.

[0304] Organic Light Emitting Diodes:

[0305] One embodiment of the present invention relates to the use of the compound represented by the general formula (1) of the present invention as a light-emitting material for an organic light-emitting element. In one embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting element. In one embodiment, the compound represented by the general formula (1) contains a delayed fluorescence (delayed fluorescent substance) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed fluorescent substance having a structure represented by the general formula (1). In one embodiment, the present invention relates to the use of the compound represented by the general formula (1) as a delayed fluorescent substance. In one embodiment, the compound represented by the general formula (1) of the present invention can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting material can be a fluorescent material, a phosphorescent material or TADF. In one embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by the general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In one embodiment, an organic light-emitting element containing the compound as a light-emitting material emits delayed fluorescence and shows high luminous efficiency.

[0306] In one embodiment, the light-emitting layer includes a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to a substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) on the film-forming surface affects or determines the propagation direction of light emitted by the arranged compound. In one embodiment, by arranging the compound represented by the general formula (1) in the propagation direction of light emitted, the light extraction efficiency from the light-emitting layer is improved.

[0307] One embodiment of the present invention relates to an organic light-emitting element. In one embodiment, the organic light-emitting element includes a light-emitting layer. In one embodiment, the light-emitting layer includes a compound represented by the general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by the general formula (1) assists the emission of other light-emitting materials contained in the light-emitting layer (as a so-called auxiliary dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet energy level, which is contained between the lowest excited singlet energy level of the main material contained in the light-emitting layer and the lowest excited singlet energy level of another light-emitting material contained in the light-emitting layer.

[0308] In one embodiment, the organic photoluminescent element comprises at least one light-emitting layer. In one embodiment, the organic electroluminescent element comprises at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer comprises at least a light-emitting layer. In one embodiment, the organic layer comprises only a light-emitting layer. In one embodiment, the organic layer comprises one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer may be a hole injection and transport layer having a hole injection function, and the electron transport layer may be an electron injection and transport layer having an electron injection function.

[0309] Luminous layer:

[0310] In one embodiment, the light emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, re-bond to form excitons. In one embodiment, the layer emits light.

[0311] In one embodiment, only a light-emitting material is used as the light-emitting layer. In one embodiment, the light-emitting layer comprises a light-emitting material and a host material. In one embodiment, the light-emitting material is one or more compounds represented by the general formula (1). In one embodiment, in order to improve the luminous efficiency of the organic electroluminescent element and the organic photoluminescent element, the singlet excitons and triplet excitons generated in the light-emitting material are confined in 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 excited singlet energy and an excited triplet energy, at least one of which is higher than those of the light-emitting material of the present invention. In one embodiment, the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are confined in the molecules of the light-emitting material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently confined to promote the luminous efficiency. In one embodiment, the singlet excitons and triplet excitons are not sufficiently confined, but a high luminous efficiency is still achieved, that is, a host material capable of achieving a high luminous efficiency can be used in the present invention without particular restrictions. In one embodiment, luminescence occurs in the luminescent material in 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 host materials are used. In one embodiment, TADF is an auxiliary dopant, and the excited singlet energy is lower than that of the host material in the luminescent layer, and the excited singlet energy is higher than that of the luminescent material in the luminescent layer.

[0312] When the compound represented by the general formula (1) is used as an auxiliary dopant, various compounds can be used as luminescent materials (preferably fluorescent materials). As such luminescent materials, anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, Derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphe nylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives with metals (Al, Zn), etc. These exemplary skeletons may have substituents or may not have substituents. In addition, these exemplary skeletons may be combined with each other.

[0313] The following are examples of light-emitting materials that can be used in combination with the assisting dopant having the structure represented by the general formula (1).

[0314] [Chemical Formula 19]

[0315]

[0316]

[0317]

[0318] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be preferably used as the light-emitting material used together with the assisting dopant having the structure represented by the general formula (1).

[0319] As further preferred light-emitting materials, compounds represented by the following general formula (2) can also be mentioned.

[0320] [Chemical Formula 20]

[0321] General formula (2)

[0322]

[0323] In the general formula (2), R 1 、R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 2 Represents an acceptor group, or R 1 and R 2 bonded to each other to form an acceptor group, or R 2 and R 3 Bond to each other to form an acceptor group. 3 and R 4 、R 4 and R 5 、R 5 and R 6 、R6 and R 7 、R 7 and R 8 、R 9 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14 、R 14 and R 15 、R 15 and R 16 Can bond to each other to form a ring structure. 1 represents O or NR, and R represents a substituent. 2 ~X 4 In, X 3 and X 4 At least one of them is O or NR, and the remaining part can be O or NR, or can be unconnected. When unconnected, the two ends independently represent hydrogen atoms, deuterium atoms or substituents. CR in the general formula (2) 1 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 Can be replaced by N.

[0324] In one embodiment of the present invention, in X 2 When it is O or NR, R 7 is an acceptor group, or R 6 and R 7 bonded to each other to form an acceptor group, or R 7 and R 8 In one embodiment of the present invention, X 3 When it is O or NR, R 10 is an acceptor group, or R 9 and R 10 bonded to each other to form an acceptor group, or R 10 and R 11In one embodiment of the present invention, X 4 When it is O or NR, R 15 is an acceptor group, or R 14 and R 15 bonded to each other to form an acceptor group, or R 15 and R 16 In one embodiment of the present invention, X 2 is NR, R is substituted or unsubstituted phenyl and through R 8 When the carbon atoms of the carbazole ring are directly bonded to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is substituted by an acceptor group. 3 is NR, R is substituted or unsubstituted phenyl and through R 9 When the carbon atoms of the carbazole ring are directly bonded to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is substituted by an acceptor group. 4 is NR, R is substituted or unsubstituted phenyl and through R 16 When the carbon atoms of the carbazole ring are directly bonded to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is substituted by an acceptor group. 1 is NR, R is substituted or unsubstituted phenyl and through R 1 When the bonded carbon atoms are directly bonded to form a carbazole ring, the 3-position of the carbazole ring is substituted with an acceptor group (wherein the 3-position is present on the phenyl group). In one embodiment of the present invention, the compound is represented by the following general formula (2a).

[0325] [Chemical Formula 21]

[0326] General formula (2a)

[0327]

[0328] In the general formula (2a), R 1 、R 3 、R 6 ~R 11 、R 14 ~R 16 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 2 Represents an acceptor group, or R 1 and R 2 bonded to each other to form an acceptor group, or R 2 and R 3 bonded to each other to form receptor groups.

[0329] R 6 and R7 、R 7 and R 8 、R 9 and R 10 、R 10 and R 11 、R 14 and R 15 、R 15 and R 16 Can bond to each other to form a ring structure. 1 represents O or NR, and R represents a substituent. 2 ~X 4 In, X 3 and X 4 At least one of them is O or NR, and the rest can be O or NR, or they can be unconnected. When unconnected, the two ends independently represent hydrogen atoms, deuterium atoms or substituents. 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 , CR 3 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 14 , CR 15 , CR 16 Can be replaced by N.

[0330] As further preferred light-emitting materials, compounds represented by the following general formula (3) can also be mentioned.

[0331] [Chemical Formula 22]

[0332] General formula (3)

[0333]

[0334] In the general formula (3), R 1 and R 2 Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 and R 3 、R 3 and R 4 、R 4 and R 5 、R5 and R 6 、R 6 and R 7 、R 7 and R 8 、R 8 and R 9 、R 9 and R 2 、R 2 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14 、R 14 and R 15 、R 15 and R 16 、R 16 and R 1 They can be bonded to each other to form a ring structure. 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 Can be replaced by N.

[0335] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. 3 and R 10 are independently substituted amino groups. In one embodiment of the present invention, R 1 and R 3 and R 2 and R 10 A combination of at least one of the following is bonded to each other to form a cyclic structure. In one embodiment of the present invention, the cyclic structure includes a benzazaborine ring.

[0336] As further preferred light-emitting materials, compounds represented by the following general formula (4) can also be mentioned.

[0337] [Chemical Formula 23]

[0338] General formula (4)

[0339]

[0340] In general formula (4), Z 1 and Z 2 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 ~R 9 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R 4 and R 5 、R 5 and R 6 、R 7 and R 8 、R 8 and R 9 Can bond with each other to form a ring structure. 1 , Z 2 、R 1 and R 2 The ring formed by bonding with each other, R 2 and R 3 The ring formed by bonding with each other, R 4 and R 5 The ring formed by bonding with each other and R 5 and R 6 At least one of the rings formed by bonding to each other 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, and R 1 ~R 9 At least one of them is a substituted or unsubstituted aryl group or an acceptor group, or Z 1 and Z 2 At least one of them is a ring having an aromatic group or an acceptor group as a substituent. The substitutable carbon atoms in the carbon atoms constituting the benzene ring skeleton of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted by nitrogen atoms. CR in the general formula (4) 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR9 Can be replaced by N.

[0341] In one embodiment of the present invention, Z 1 and Z 2 are independently a substituted or unsubstituted non-fused benzene ring, a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or a pyrrole ring formed by condensing substituted or unsubstituted benzene rings. 1 ~R 9 are independently substituted or unsubstituted aryl or acceptor groups, or selected from R 1 and R 2 The ring formed by bonding with each other, R 2 and R 3 The ring formed by bonding with each other, R 4 and R 5 The ring formed by bonding with each other and R 5 and R 6 One or more rings in the group of rings formed by bonding to each other are a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or a pyrrole ring formed by condensing substituted or unsubstituted benzene rings. In one embodiment of the present invention, R 8 is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, it contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0342] As further preferred light-emitting materials, there can be mentioned compounds having a fused ring structure A (the hydrogen atoms in the structure may be substituted by deuterium atoms or substituents) in which a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring is fused to a carbon-carbon bond a having the following structure α, or a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzodioxane ring is fused to a carbon-carbon bond b.

[0343] [Chemical Formula 24]

[0344] Structure α

[0345]

[0346] In structure α, X 1 and X 2Each independently represents a nitrogen atom or an oxygen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded, Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaryl ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, Z and X 2 They may be bonded to each other to form a ring structure.

[0347] In the fused ring structure A, the structure fused with b and X 1 , structures fused with b and Z, Z and X 2 They may be bonded to each other to form a ring structure.

[0348] As further preferred light-emitting materials, compounds represented by the following general formula (5) can also be mentioned.

[0349] [Chemical Formula 25]

[0350] General formula (5)

[0351]

[0352] In general formula (5), Z 1 represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 Z each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 、R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 Can bond with each other to form a ring structure. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one group of them is bonded to each other to form a ring structure.

[0353] As further preferred light-emitting materials, compounds represented by the following general formula (6) can also be mentioned.

[0354] [Chemical Formula 26]

[0355] General formula (6)

[0356]

[0357] In general formula (6), X 3 represents an oxygen atom or a sulfur atom, Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 4 ~R 7 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 、R 4 and R 5 、R 5 and R 6 、R 6 and R 7 Can bond with each other to form a ring structure. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one group of them is bonded to each other to form a ring structure.

[0358] As further preferred light-emitting materials, compounds represented by the following general formula (7) can also be mentioned.

[0359] [Chemical Formula 27]

[0360] General formula (7)

[0361]

[0362] In general formula (7), X 4 represents an oxygen atom or a sulfur atom, Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 4a ~R 7a represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 、R 4a and R 5a 、R 5a and R 6a 、R 6a and R 7a 、R 7a and R 1 Can bond with each other to form a ring structure. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one group of them is bonded to each other to form a ring structure.

[0363] As further preferred light-emitting materials, compounds represented by the following general formula (8) can also be mentioned.

[0364] [Chemical Formula 28]

[0365] General formula (8)

[0366]

[0367] In general formula (8), Z 1 represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 8 ~R 14 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 3 Z represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 、R 8 and R 9 、R 9 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14、R 14 and Z 3 , Z 3 and R 3 They may be bonded to each other to form a ring structure.

[0368] As further preferred light-emitting materials, compounds represented by the following general formula (9) can also be mentioned.

[0369] [Chemical Formula 29]

[0370] General formula (9)

[0371]

[0372] In general formula (9), Z 1 and Z 4 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 15 ~R 17 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 3 Z represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , Z 4 and R 15 、R 15 and R 16 、R 16 and R 17 、R 17 and Z 3 , Z 3 and R 3 They may be bonded to each other to form a ring structure.

[0373] As further preferred light-emitting materials, compounds represented by the following general formula (10) can also be mentioned.

[0374] [Chemical formula 30]

[0375] General formula (10)

[0376]

[0377] In the general formula (10), Z 1 and Z 5Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 Z each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 、R 2 and Z 5 , Z 5 and Z 3 , Z 3 and R 3 Can bond with each other to form a ring structure. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one group of them is bonded to each other to form a ring structure.

[0378] As further preferred light-emitting materials, compounds represented by the following general formula (11) can also be mentioned.

[0379] [Chemical Formula 31]

[0380] General formula (11)

[0381]

[0382] In the general formula (11), Z 1 represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 21 ~R 27 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 2 and Z 2 , Z 2 and R 21 、R 21 and R 22 、R22 and R 23 、R 23 and R 24 、R 24 and R 25 、R 25 and R 26 、R 26 and R 27 They may be bonded to each other to form a ring structure.

[0383] As further preferred light-emitting materials, compounds represented by the following general formula (12) can also be mentioned.

[0384] [Chemical Formula 32]

[0385] General formula (12)

[0386]

[0387] In the general formula (12), Z 1 and Z 6 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 28 ~R 30 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 2 and Z 2 , Z 2 and R 28 、R 28 and R 29 、R 29 and R 30 、R 30 and Z 6 They may be bonded to each other to form a ring structure.

[0388] As further preferred light-emitting materials, compounds represented by the following general formula (13) can also be mentioned.

[0389] [Chemical Formula 33]

[0390] General formula (13)

[0391]

[0392] In the general formula (13), Z1 and Z 7 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 Can bond with each other to form a ring structure. 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 At least one group of them is bonded to each other to form a ring structure.

[0393] As further preferred light-emitting materials, compounds represented by the following general formula (14) can also be mentioned.

[0394] [Chemical Formula 34]

[0395] General formula (14)

[0396]

[0397] In the general formula (14), Z 1 represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, R 1 and R 31 ~R 44 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 31 and R 32 、R 32 and R 33 、R 33 and R 34 、R 34 and R 35 、R 35 and R36 、R 36 and R 37 、R 37 and R 38 、R 38 and R 39 、R 39 and R 40 、R 40 and R 41 、R 41 and R 42 、R 42 and R 43 、R 43 and R 44 They may be bonded to each other to form a ring structure.

[0398] As further preferred light-emitting materials, compounds represented by the following general formula (15) can also be mentioned.

[0399] [Chemical Formula 35]

[0400] General formula (15)

[0401]

[0402] In the general formula (15), Z 1 and Z 8 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and R 1 and R 51 ~R 60 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 and Z 1 、R 51 and R 52 、R 52 and R 53 、R 53 and R 54 、R 54 and R 55 、R 55 and R 56 、R 56 and R 57 、R 57 and R 58 、R 58 and R 59 、R 59 and R 60 、R 60 and Z 8 They may be bonded to each other to form a ring structure.

[0403] As further preferred light-emitting materials, compounds represented by the following general formula (16) can also be mentioned.

[0404] [Chemical Formula 36]

[0405] General formula (16)

[0406]

[0407] In general formula (16), Z 1 , Z 8 and Z 9 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and R 1 and R 61 ~R 66 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 and Z 1 , Z 9 and R 61 、R 61 and R 62 、R 62 and R 63 、R 63 and R 64 、R 64 and R 65 、R 65 and R 66 、R 66 and Z 8 They may be bonded to each other to form a ring structure.

[0408] As further preferred light-emitting materials, compounds represented by the following general formula (17) can also be mentioned.

[0409] [Chemical Formula 37]

[0410] General formula (17)

[0411]

[0412] In general formula (17), Z 1 , Z 9 and Z 10 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and R 1 and R 67 ~R 69 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 70represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , Z 9 and R 67 、R 67 and R 68 、R 68 and R 69 、R 69 and Z 10 , Z 10 and R 70 They may be bonded to each other to form a ring structure.

[0413] As further preferred light-emitting materials, compounds represented by the following general formula (18) can also be mentioned.

[0414] [Chemical Formula 38]

[0415] General formula (18)

[0416]

[0417] In the general formula (18), Z 1 , Z 11 and Z 12 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and R 1 and R 72 ~R 74 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 71 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 71 and Z 11 , Z 11 and R 72 、R 72 and R 73 、R 73 and Z 74 、R 74 and Z 12 They may be bonded to each other to form a ring structure.

[0418] As further preferred light-emitting materials, compounds represented by the following general formula (19) can also be mentioned.

[0419] [Chemical Formula 39]

[0420] General formula (19)

[0421]

[0422] In the general formula (19), Z 1 and Z 11 Each independently represents a furan ring formed by condensing substituted or unsubstituted benzene rings, a thiophene ring formed by condensing substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by condensing substituted or unsubstituted benzene rings, and R 1 and R 76 ~R 82 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 75 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and Z 1 、R 75 and Z 11 , Z 11 and R 76 、R 76 and R 77 、R 77 and R 78 、R 78 and R 79 、R 79 and R 80 、R 80 and R 81 、R 81 and R 82 They may be bonded to each other to form a ring structure.

[0423] As further preferred light-emitting materials, compounds represented by the following general formula (20) can also be mentioned.

[0424] [Chemical Formula 40]

[0425] General formula (20)

[0426]

[0427] In the general formula (20), X 5 represents an oxygen atom, a sulfur atom, or a nitrogen atom bonded to a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 101 ~R 130 Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 101 and R 102 、R 102 and R 103 、R 103 and R 104 、R 104 and R 105 、R 105 and R 106 、R106 and R 107 、R 107 and R 108 、R 108 and R 109 、R 109 and R 110 、R 110 and R 111 、R 111 and R 112 、R 112 and R 113 、R 113 and R 114 、R 114 and R 115 、R 115 and R 116 、R 116 and R 117 、R 117 and R 118 、R 118 and R 119 、R 119 and R 120 、R 120 and R 121 、R 121 and R 122 、R 122 and R 123 、R 123 and R 124 、R 124 and R 125 、R 125 and R 126 、R 126 and R 127 、R 127 and R 128 、R 128 and R 129 、R 129 and R 130 、R 130 and R 101 They may be bonded to each other to form a ring structure.

[0428] As further preferred light-emitting materials, compounds represented by the following general formula (21) can also be mentioned.

[0429] [Chemical Formula 41]

[0430] General formula (21)

[0431]

[0432] In the general formula (21), R 1 and R 2Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and Z 1 and Z 2 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 3 ~R 9 Each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 、R 2 , Z 1 and Z 2 At least one of the R comprises a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. 1 and Z 1 , Z 1 and R 3 、R 3 and R 4 、R 4 and R 5 、R 5 and Z 2 , Z 2 and R 2 、R 2 and R 6 、R 6 and R 7 、R 7 and R 8 、R 8 and R 9 、R 9 and R 1 The carbon atoms that can be substituted among the carbon atoms that constitute the benzene ring skeleton of the benzofuran ring, the benzothiophene ring, and the indole ring can be substituted by nitrogen atoms. 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 Can be replaced by N.

[0433] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. In one embodiment of the present invention, Z 1 and Z 2are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with substituted or unsubstituted benzene rings, a thiophene ring fused with substituted or unsubstituted benzene rings, a pyrrole ring fused with substituted or unsubstituted benzene rings, a benzene ring fused with substituted or unsubstituted benzofuran rings, a benzene ring fused with substituted or unsubstituted benzothiophene rings, or a benzene ring fused with substituted or unsubstituted indole rings. In one embodiment of the present invention, R 1 and Z 1 In one embodiment of the present invention, R 1 and Z 1 They are bonded to each other to form a pyrrole ring.

[0434] As further preferred light-emitting materials, compounds represented by the following general formula (22) can also be mentioned.

[0435] [Chemical Formula 42]

[0436] General formula (22)

[0437]

[0438] In the general formula (22), X 1 and X 2 One of them is a nitrogen atom and the other is a boron atom. 1 ~R 26 、A 1 、A 2 R each independently represents a hydrogen atom, a deuterium atom or a substituent. 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R 4 and R 5 、R 5 and R 6 、R 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 、R16 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 Can bond with each other to form a ring structure. 1 When it is a nitrogen atom, R 17 and R 18 bonded to each other to form a single bond to form a pyrrole ring, in X 2 When it is a nitrogen atom, R 21 and R 22 bonded to each other to form a single bond to form a pyrrole ring. 1 is a nitrogen atom, R 7 and R 8 and R 21 and R 22 The nitrogen atom forms a 6-membered ring, R 17 and R 18 When they are bonded 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 of them are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0439] In one embodiment of the present invention, R 3 and R 6 At least one of is a substituent. In one embodiment of the present invention, R 3 and R 6 In one embodiment of the present invention, R 3 and R 6The substituent represented is one or a combination of two or more selected from the group consisting of alkyl and aryl groups. 8 and R 12 In one embodiment of the present invention, it is represented by the following general formula (22a).

[0440] [Chemical Formula 43]

[0441] General formula (22a)

[0442]

[0443] In the general formula (22a), Ar 1 ~Ar 4 R each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 41 and R 42 Each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represent an integer of 0 to 5, n1 and n3 each independently represent an integer of 0 to 4, and n2 and n4 each independently represent an integer of 0 to 3. 1 、A 2 Each independently represents a hydrogen atom, a deuterium atom or a substituent.

[0444] For detailed descriptions, preferred ranges, and specific examples of the compounds represented by general formula (22) or general formula (22a), reference can be made to paragraphs

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as a part of this specification. For example, the following compounds can be exemplified.

[0445] [Chemical Formula 44]

[0446]

[0447] In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 10% by weight or less.

[0448] In one embodiment, the host material in the light-emitting layer is an organic compound that has both hole-transporting and electron-transporting functions. In one embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of emitted light. In one embodiment, the host material in the light-emitting layer is an organic compound with a high glass transition temperature.

[0449] In some embodiments, the host material is selected from the group consisting of:

[0450] [Chemical Formula 45]

[0451]

[0452]

[0453] In one embodiment, the light-emitting layer comprises two or more TADF molecules with different structures. For example, the light-emitting layer can be made of three materials, with the excited singlet energy level increasing 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 energy level of the first TADF molecule and the lowest excited triplet energy level at 77K is STThey 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, further preferably 0.1 eV or less, further preferably 0.07 eV or less, further preferably 0.05 eV or less, further 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 main material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer may be greater than the concentration of the main material, may be less than the concentration of the main material, or may be the same. In one embodiment, the composition in the light-emitting layer may be set as follows: the main material is set to 10 to 70 weight %, the first TADF molecule is set to 10 to 80 weight %, and the second TADF molecule is set to 0.1 to 30 weight %. In one embodiment, the composition of the light-emitting layer can be as follows: the host material is 20-45 wt%, the first TADF molecules are 50-75 wt%, and the second TADF molecules are 5-20 wt%. In one embodiment, the luminescence quantum yield φPL1(A) due to photoexcitation of a co-deposited film of the first TADF molecules and the host material (the concentration of the first TADF molecules in the co-deposited film = A wt%) and the luminescence quantum yield φPL2(A) due to photoexcitation of a co-deposited film of the second TADF molecules and the host material (the concentration of the second TADF molecules in the co-deposited film = A wt%) satisfy the relationship φPL1(A)>φPL2(A). In one embodiment, the luminescence quantum yield φPL2(B) resulting from photoexcitation of a co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-deposited film = B wt%) and the luminescence quantum yield φPL2(100) resulting from photoexcitation of a single film of the second TADF molecule satisfy the relationship φPL2(B)>φPL2(100). In one embodiment, the light-emitting layer can contain three structurally different TADF molecules. The compound of the present invention can be any one of the multiple TADF compounds contained in the light-emitting layer.

[0454] 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 a metal element. In one embodiment, the light-emitting layer can be composed of a material consisting solely of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material consisting solely of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be composed of a material consisting solely of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0455] When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescence material. Preferred delayed fluorescence materials include paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraphs 0008 to 007 of WO2013 / 081088. 1 and 0118 to 0133, 0009 to 0046 and 0093 to 0134 of Japanese Patent Application Laid-Open No. 2013-256490, 0008 to 0020 and 0038 to 0040 of Japanese Patent Application Laid-Open No. 2013-116975, 0007 to 0032 and 0079 to 0084 of WO2013 / 133359, 0008 to 0010 of WO2013 / 161437 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of Japanese Patent Application Laid-Open No. 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of Japanese Patent Application Laid-Open No. 2014-9224, paragraphs 0013 to 0025 of Japanese Patent Application Laid-Open No. 2017-119663, paragraphs 0013 to 0026 of Japanese Patent Application Laid-Open No. 2017-119664, Compounds included in the general formula described in paragraphs 0012 to 0025 of Japanese Patent Application Laid-Open No. 2017-222623, paragraphs 0010 to 0050 of Japanese Patent Application Laid-Open No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Application Laid-Open No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, especially exemplary compounds that can emit delayed fluorescence.Among them, Japanese Patent Application Laid-Open No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO 2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO 2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Laid-Open No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO Compounds capable of emitting delayed fluorescence and being luminescent materials described in WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The aforementioned publications described in this paragraph are incorporated herein by reference as part of this specification.

[0456] The following describes the various components of the organic electroluminescent element and the various layers other than the light-emitting layer.

[0457] Substrate:

[0458] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those substrates that have been commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz, and silicon.

[0459] anode:

[0460] In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a large 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 such as IDIXO (In2O3-ZnO) capable of forming a transparent conductive film is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when the pattern may not require high precision (for example, about 100 μm or more), the pattern can be formed using a mask of a preferred shape when evaporation or sputtering is performed on the electrode material. In some embodiments, when a coating material (such as an organic conductive compound) can be coated, a wet film formation method such as a printing method and a coating method is used. In some embodiments, the anode has a transmittance greater than 10% when the emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per square or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0461] cathode:

[0462] In some embodiments, the cathode is made of a metal (less than 4 eV) (referred to as an electron injection metal) whose electrode material has a relatively small work function, an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth metals. In some embodiments, a mixture of an electron injection metal and a second metal is used, and the second metal is a stable metal having a work function greater than that of the electron injection metal. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture increases electron injection properties and durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by evaporation or sputtering. In some embodiments, the sheet resistance of the cathode is less than several hundred ohms per square. 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, to transmit the emitted light, either the anode or cathode of the organic electroluminescent element is transparent or translucent. In some embodiments, a transparent or translucent electroluminescent element enhances the luminance of the emitted light.

[0463] In some embodiments, the cathode is formed from a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, a device comprises an anode and a cathode that are both transparent or translucent.

[0464] Injection layer:

[0465] The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminescence brightness. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be arranged between the anode and the light-emitting layer or the hole transport layer, and between the cathode and the light-emitting layer or the electron transport layer. In some embodiments, the injection layer is present. In some embodiments, the injection layer is not present.

[0466] Preferred examples of compounds that can be used as hole injection materials are listed below.

[0467] [Chemical Formula 46]

[0468] MoO3,

[0469]

[0470] Next, preferred examples of compounds that can be used as electron injection materials are given.

[0471] [Chemical Formula 47]

[0472] LiF, CsF,

[0473] Barrier layer:

[0474] The blocking layer is a layer that can inhibit the charges (electrons or holes) and / or excitons in the light-emitting layer from diffusing to the outside of the light-emitting layer. In some embodiments, the electron blocking layer is between the light-emitting layer and the hole transport layer, and inhibits electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron transport layer, and inhibits holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer inhibits excitons from diffusing 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. The term "electron blocking layer" or "exciton blocking layer" used in this specification includes a layer having the functions of both an electron blocking layer and an exciton blocking layer.

[0475] Hole blocking layer:

[0476] The hole-blocking layer functions as an electron-transporting layer. In some embodiments, the hole-blocking layer prevents holes from reaching the electron-transporting layer while transporting electrons. In some embodiments, the hole-blocking layer increases the probability of recombination between electrons and holes in the light-emitting layer. The materials used for the hole-blocking layer can be the same as those described for the electron-transporting layer.

[0477] Preferred examples of compounds that can be used in the hole-blocking layer are listed below.

[0478] [Chemical Formula 48]

[0479]

[0480] Electron blocking layer:

[0481] The electron blocking layer transports holes. In some embodiments, the electron blocking layer simultaneously transports holes and inhibits electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer enhances the probability of recombination between electrons and holes in the light-emitting layer. The materials used for the electron blocking layer can be the same as those described for the hole transport layer.

[0482] Specific examples of preferred compounds that can be used as electron-blocking materials are given below.

[0483] [Chemical Formula 49]

[0484]

[0485] Exciton blocking layer:

[0486] The exciton blocking layer inhibits the diffusion of excitons generated by the recombination of holes and electrons in the light-emitting layer to the electron transport layer. In some embodiments, the exciton blocking layer enables the excitons to be effectively confined in the light-emitting layer. In some embodiments, the luminous efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side and on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer can be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer can be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or the same layer is between the anode and the exciton blocking layer, and the exciton blocking layer is 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 between the cathode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton-blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the light-emitting material, respectively.

[0487] Hole transport layer:

[0488] 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.

[0489] In some embodiments, the hole transport material has one of the injection or transport characteristics of holes and the blocking characteristics of electrons. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. As examples of known hole transport materials that can be used in the present invention, there is no limitation, and triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indole and carbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers and conductive polymer oligomers (especially thiophene oligomers) or combinations thereof can be cited. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amines and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Below, the specific examples of preferred compounds that can be used as hole transport materials are given.

[0490] [Chemical Formula 50]

[0491]

[0492] Electron transport layer:

[0493] 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.

[0494] In some embodiments, the electron transport material only needs to have the function of transporting electrons, which are injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole blocking material. As examples of electron transport layers that can be used in the present invention, there is no limitation, and examples include fluorene derivatives, dibenzoquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylmethane derivatives, anthraquinone dimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, oxazine derivatives, or combinations thereof or polymers thereof substituted by nitro groups. 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. Below, specific examples of preferred compounds that can be used as electron transport materials are given.

[0495] [Chemical Formula 51]

[0496]

[0497] Furthermore, preferred examples of compounds that can be added to each organic layer are given below. For example, it is conceivable that they can be added as a stabilizing material.

[0498] [Chemical Formula 52]

[0499]

[0500] Preferred materials that can be used in organic electroluminescent devices are specifically exemplified. However, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be used as materials having other functions.

[0501] Device:

[0502] In some embodiments, the light-emitting layer is incorporated into a device. Examples of devices include, but are not limited to, OLED bulbs, OLED lamps, television screens, computer monitors, mobile phones, and tablet computers.

[0503] In some embodiments, an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer disposed between the anode and the cathode.

[0504] In some embodiments, the compositions described herein can be incorporated into various light-sensitive or light-activated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be used to promote charge transfer or energy transfer within the device and / or be used as hole transport materials. Examples of the devices include 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), and organic laser diodes (O-lasers).

[0505] Light Bulb or Lamp:

[0506] In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer disposed between the anode and the cathode.

[0507] In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than 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.

[0508] In some embodiments, the device is an OLED lamp having:

[0509] A circuit board having a first surface having a mounting surface and a second surface opposite thereto, and defining at least one opening;

[0510] 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 including a light-emitting layer disposed between the anode and the cathode and emits light;

[0511] Housing for a circuit substrate; and

[0512] At least one connector is disposed at an end of the housing, and the housing and the connector define a package suitable for mounting on a lighting device.

[0513] In some embodiments, an OLED lamp includes a plurality of OLEDs mounted on a circuit substrate such that light is emitted 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.

[0514] Monitor or screen:

[0515] In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention are deposited onto a substrate using methods including (but not limited to) vacuum evaporation, deposition, vapor deposition or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure suitable for double-sided etching, providing unique aspect ratio pixels. The screen (which may also be referred to as a mask) is used in a method for manufacturing an OLED display. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and promotes larger swept angle 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.

[0516] Internal patterning of the pixel allows the construction of 3D pixel openings with varying aspect ratios in both the horizontal and vertical directions. Furthermore, imaged “stripes” or halftone circles are used within the pixel area to suppress etching in specific areas until these specific patterns are undercut and removed from the substrate. At this point, all pixel areas are processed at the same etch rate, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone pattern allows etching to be suppressed at different rates within the pixel, allowing for the locally deeper etching required to create steep vertical bevels.

[0517] The preferred material for the vapor deposition mask is invar. Invar is a metal alloy that is cold-rolled into long thin sheets in a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and cost-effective method for forming the openings in the vapor deposition mask is based on wet chemical etching.

[0518] In some embodiments, the screen or display pattern is a matrix of pixels on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (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.

[0519] Device manufacturing method:

[0520] OLED displays are typically manufactured by forming a large motherboard and then cutting it into unit panels. Generally speaking, 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 base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, an opposing electrode, and an encapsulation layer, and then cutting from the motherboard.

[0521] In another embodiment of the present invention, a method for manufacturing an organic light emitting diode (OLED) display is provided, the method comprising:

[0522] forming a barrier layer on a base substrate of a motherboard;

[0523] forming a plurality of display units on the barrier layer from a unit panel unit;

[0524] forming an encapsulation layer on each of the display units of the unit panel; and

[0525] A process of coating an organic film on the interface portion between the unit plates.

[0526] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edge portion of the barrier layer is covered with an organic film formed of polyimide or acryl. In some embodiments, the organic film helps to gently cut the motherboard into unit board units.

[0527] In some embodiments, the thin film transistor (TFT) layer has a light-emitting layer, a gate electrode, and a source electrode / 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 the organic film applied to the interface portion is formed of the same material as the planarization film and is formed at the same time as the planarization film is formed. 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 contacts neither the display unit nor the encapsulation layer.

[0528] Each of the organic film and the planarization film may include any one of polyimide and acryl. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include, before forming the barrier layer on one surface of the base substrate formed of polyimide, mounting a carrier substrate formed of a glass material on another surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0529] 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 acryl, as is the organic film formed on the edge portion of the barrier layer. In some embodiments, when manufacturing the OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film can be formed on the edge portion of the barrier layer so that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0530] In some embodiments, the light-emitting layer comprises a pixel electrode, an opposite electrode, and an organic light-emitting layer disposed between the pixel electrode and the opposite electrode. In some embodiments, the pixel electrode is connected to a source electrode / drain electrode of a TFT layer.

[0531] 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 counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image forming unit including the TFT layer and the light-emitting unit is referred to as a display unit.

[0532] In some embodiments, the encapsulation layer that covers the display unit and prevents external moisture penetration can be formed to have a thin film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the multiple display units. In some embodiments, the organic film is formed so that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0533] In one embodiment, the OLED display is flexible and uses a soft base substrate formed of polyimide. In some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0534] In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit board. For example, while the base substrate is formed over the entire surface of the motherboard, the barrier layer is formed according to the size of each unit board, thereby forming grooves at the interface between the unit board and the barrier layer. Each unit board can be cut along the grooves.

[0535] In some embodiments, the manufacturing method further includes a process of cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of the organic film is formed in the groove, and the groove does not penetrate into the base substrate. In some embodiments, the TFT layer of each unit plate is formed, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are arranged on the TFT layer to cover the TFT layer. While forming a planarization film formed by, for example, polyimide or acryl, the groove at the interface portion is covered with an organic film formed by, for example, polyimide or acryl. This is when cracking is prevented from occurring by allowing the organic film to absorb the impact generated when each unit plate is cut along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the impact generated when each unit plate 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 between the barrier layers are covered with an organic film, and the organic film absorbs the impact that would otherwise be transferred to the barrier layer, each unit board can be cut gently, and cracks in the barrier layer can be prevented. In one embodiment, the organic film covering the grooves at the interface is separated from the planarization film. For example, if the organic film and the planarization film were connected as a single layer, external moisture could penetrate into the display unit through the planarization film and the portion where the organic film remains. Therefore, the organic film and the planarization film are separated from each other to separate the organic film from the display unit.

[0536] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the motherboard is fully manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate separates from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate.

[0537] In some embodiments, a motherboard is cut into unit boards. In some embodiments, a cutting machine is used to cut the motherboard along the interface between the unit boards. In some embodiments, because the grooves at the interface along which the motherboard is cut are covered with an organic film, the organic film absorbs shock during cutting. In some embodiments, cracks can be prevented from occurring in the barrier layer during cutting.

[0538] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0539] Another embodiment is an OLED display including: a barrier layer formed on a base substrate; display units formed on the barrier layer; an encapsulation layer formed on the display units; and an organic film coated on edge portions of the barrier layer.

[0540] Example

[0541] The following synthesis examples and embodiments are provided to further specifically illustrate the features of the present invention. The materials, processing contents, processing steps, etc. shown below can be appropriately changed as long as they do not depart from the main purpose of the present invention. Therefore, the scope of the present invention should not be interpreted restrictively by the specific examples shown below. In addition, the evaluation of luminescence characteristics was carried out using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd.: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), a spectrometer (Ocean Optics: USB2000), a spectroradiometer (TOPCON CORPO RATION: SR-3) and a streak camera (Hamamatsu Photonics KK C4334 model). In addition, the measurement of the HOMO and LUMO energies was carried out using an atmospheric photoelectron spectrometer (RIKEN KEIKI CO., LTD. AC-3, etc.).

[0542] In the following synthesis examples, compounds represented by the general formula (1) were synthesized.

[0543] (Synthesis Example 1) Synthesis of Compound 46542

[0544] [Chemical Formula 53]

[0545]

[0546] Compound a

[0547] Under a nitrogen atmosphere, a solution of tetrahydrofuran (200 mL) and distilled water in which (phenyl-d5)boric acid (3.16 g, 24.90 mmol), 2,4-difluoro-3-iodopyridine (5.00 g, 20.75 mmol), potassium carbonate (8.60 g, 62.25 mmol, 2M aqueous solution) and tetrakis(triphenylphosphine)palladium(0) (3 mol%) were dissolved was refluxed for 12 hours. The reaction solution was cooled to room temperature, extracted with dichloromethane and distilled water, and then the solvent was distilled off from the organic layer using an evaporator. The residue was purified by silica gel column chromatography using a mixed solvent of chloroform:hexane = 1:1 as the eluent to obtain compound a (2.80 g, 14.27 mmol, 68.8% yield) as a white solid.

[0548] 1 H NMR (400 MH Z ,CDCl3)δ8.1675(dd,J=8.0H Z ,6.0H Z ,1H),7.0725(dd,J=8.2H Z ,5.2H Z ,1H)

[0549] ASAP MS spectrum analysis: C11H2D5F2N: theoretical value 196, observed value 197.

[0550] [Chemical Formula 54]

[0551]

[0552] Compound b

[0553] Under a nitrogen stream, a 1 M lithium diisopropylamide solution (3.57 mL, 3.57 mmol) was added little by little to a tetrahydrofuran solution (15 mL) of compound a (0.70 g, 3.57 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.66 g, 3.57 mmol) at -85°C. After 10 minutes, the mixture was warmed to -75°C, stirred for 1 hour, and then slowly returned to room temperature. To the mixture were added 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (1.98 g, 4.28 mmol), 2M aqueous potassium carbonate solution (2.68 mL, 5.35 mmol), tetrahydrofuran (100 mL), tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.11 mmol), and heated under reflux for 12 hours. The reaction solution was returned to room temperature, water was added to stop the reaction, and then extracted with chloroform, and the solvent was distilled off with an evaporator. The residue was purified by silica gel column chromatography using a mixed solvent of hexane:toluene = 1:1 as an eluent to obtain compound b (1.00 g, 1.61 mmol, 45.1% yield) as a white solid.

[0554] 1 H NMR (400 MH Z ,CDCl3)δ9.3635(d,J=9.2H Z ,1H).

[0555] ASAP MS spectrum analysis: C38HD21F2N6: theoretical value 621, observed value 622.

[0556] [Chemical Formula 55]

[0557]

[0558] Compound 46542

[0559] Under a nitrogen stream, a dimethylformamide solution (50 mL) obtained by dissolving 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.76 g, 4.34 mmol), potassium carbonate (0.80 g, 5.79 mmol) and compound b (0.9 g, 1.45 mmol) was stirred at 120 ° C overnight. The reactant was returned to room temperature, saturated ammonium chloride solution was added to stop the reaction, and then extracted with chloroform, and the solvent was distilled off with an evaporator. A mixed solvent of toluene and hexane was used as an eluent, and the obtained residue was purified by silica gel column chromatography to obtain compound 46542 (0.83 g, 0.89 mmol, yield 61.5%).

[0560] 1 H NMR (400 MH Z ,CDCl3)δ9.632(s,1H).

[0561] ASAP MS spectral analysis: C62HD37N8: theoretical value 931, observed value 932.

[0562] (Synthesis Example 2) Synthesis of Compound 46542 (40)

[0563] [Chemical Formula 56]

[0564]

[0565] Compound c

[0566] Under a nitrogen stream, a 1 M lithium diisopropylamide solution (5.10 mL, 5.10 mmol) was added little by little to a tetrahydrofuran solution (15 mL) of compound a (1.00 g, 5.09 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.95 g, 5.10 mmol) at -85°C. After 10 minutes, the mixture was warmed to -75°C, stirred for 1 hour, and then slowly returned to room temperature. To the mixture were added 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazine-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d (2.26 g, 6.11 mmol), 2M aqueous potassium carbonate solution (3.82 mL, 7.64 mmol), tetrahydrofuran (60 mL), and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol), and the mixture was heated under reflux for 12 hours. The reaction solution was returned to room temperature, water was added to stop the reaction, and then extracted with chloroform, and the solvent was distilled off using an evaporator. The residue was purified by silica gel column chromatography using a mixed solvent of hexane:toluene = 1:1 as the eluent to obtain compound c (2.40 g, 4.53 mmol, 89.0% yield) as a white solid.

[0567] 1 H NMR (400 MH Z ,CDCl3)δ9.34(d,J=9.2H Z ,1H).

[0568] ASAP MS spectrum analysis: C32HD18F2N: theoretical value 529, observed value 530.

[0569] [Chemical Formula 57]

[0570]

[0571] Compound 46542(40)

[0572] Under a nitrogen stream, a dimethylformamide solution (50 mL) obtained by dissolving 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.50 g, 8.50 mmol), potassium carbonate (1.57 g, 11.33 mmol) and compound c (1.5 g, 2.83 mmol) was stirred at 120°C overnight. The reactant was returned to room temperature, saturated ammonium chloride solution was added to stop the reaction, and then extracted with chloroform, and the solvent was distilled off using an evaporator. The obtained residue was purified by silica gel column chromatography using a mixed solvent of toluene and hexane as an eluent to obtain compound 46542 (40) (2.20 g, 2.62 mmol, yield 92.5%).

[0573] 1 H NMR (400 MH Z ,CDCl3)δ9.725(s,1H).

[0574] ASAP MS spectrum analysis: C56HD34N7: theoretical value 839, observed value 840.

[0575] (Comparative Synthesis Example 1) Synthesis of Comparative Compound 2

[0576] [Chemical Formula 58]

[0577]

[0578] Compound d

[0579] Under a nitrogen stream, a 1M lithium diisopropylamide solution (5.10 mL, 5.10 mmol) was added gradually to a tetrahydrofuran solution (15 mL) of compound a (1.0 g, 5.10 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) at -85°C. After 10 minutes, the mixture was warmed to -75°C, stirred for 1 hour, and then slowly returned to room temperature. To this mixture were added 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (1.56 g, 5.60 mmol), a 2M aqueous potassium carbonate solution (3.82 mL, 7.64 mmol), tetrahydrofuran (20 mL), and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol), followed by heating under reflux for 12 hours. The reaction solution was returned to room temperature, and water was added to stop the reaction. The product was then extracted with chloroform, and the solvent was removed by distillation using an evaporator. The resulting residue was purified by silica gel column chromatography using a 1:1 hexane:toluene mixture as the eluent to obtain compound d (2.00 g, 4.57 mmol, 89.8% yield) as a white solid.

[0580] 1 H NMR (400 MH Z ,CDCl3)δ9.34(d,J=9.2H Z ,1H).

[0581] ASAP MS spectrum analysis: C26HD15F2N: theoretical value 437, observed value 438.

[0582] [Chemical Formula 59]

[0583]

[0584] Comparative Compound 2

[0585] Under a nitrogen stream, a dimethylformamide solution (50 mL) obtained by dissolving 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.80 g, 10.29 mmol), potassium carbonate (1.90 g, 13.71 mmol) and compound d (1.5 g, 3.43 mmol) was stirred at 120 ° C overnight. The reactant was returned to room temperature, saturated ammonium chloride solution was added to stop the reaction, and then extracted with chloroform, and the solvent was distilled off with an evaporator. The residue was purified by silica gel column chromatography using a mixed solvent of toluene and hexane as an eluent to obtain comparative compound 2 (2.45 g, 3.28 mmol, yield 95.5%).

[0586] 1 H NMR (400 MH Z ,CDCl3)δ9.705(s,1H).

[0587] ASAP MS spectral analysis: C50HD31N6: theoretical value 747, observed value 748.

[0588] (Synthesis Example 3) Synthesis of Compound 38317 (40)

[0589] [Chemical Formula 60]

[0590]

[0591] Compound e

[0592] 2-([1,1':3',1"-terphenyl]-5'-yl-2,2",3,3",4,4",5,5",6,6"-d10)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.52 g, 6.88 mmol), 2,4-difluoro-3-iodopyridine (1.66 g, 6.88 mmol), potassium carbonate (1.43 g, 10.32 mmol, 2M aqueous solution), Pd(PPh3)4 (3 mol%) were dissolved in tetrahydrofuran (20 mL) and distilled water (based on the amount of potassium carbonate). Under a nitrogen atmosphere, the solution was refluxed for 12 hours and then cooled to room temperature. The solution was extracted with dichloromethane and distilled water. The solution of the organic layer was evaporated under vacuum and purified with chloroform:hexane (1:1). Compound e (2.30 g, 6.507 mmol, 94.6% yield) was obtained as a white solid.

[0593] 1 H NMR (400 MH Z ,CDCl3)δ8.213(dd,J=8.0H Z ,5.6H Z ,1H),7.868(t,J=2.0H Z ,1H),7.676(q,J=1.6H Z ,2H),7.12(dd,J=8.0H Z ,5.6H Z ,1H)

[0594] ASAP MS spectrum analysis: C23H5D10F2N: theoretical value 353, observed value 354.

[0595] [Chemical Formula 61]

[0596]

[0597] Compound f

[0598] Under a nitrogen stream, a 1 M lithium diisopropylamide solution (2.83 mL, 2.83 mmol) was added little by little to a tetrahydrofuran solution (15 mL) of compound e (1.0 g, 2.83 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.53 g, 2.83 mmol) cooled to -85°C. After 10 minutes, the temperature was raised to -75°C and stirred for 1 hour. After the mixture was slowly returned to room temperature, 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazine-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.15 g, 3.12 mmol), 2M aqueous potassium carbonate solution (2.13 mL, 4.26 mmol), tetrahydrofuran (100 mL), tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.09 mmol) were added and heated under reflux for 12 hours. After the reaction solution was returned to room temperature, water was added for quenching and extracted with chloroform. The solvent was distilled off with an evaporator and purified by silica gel column chromatography (hexane: toluene = 1: 1) to obtain compound f (1.28 g, 1.864 mmol, yield 65.7%) as a white solid.

[0599] 1 H NMR (400 MH Z ,CDCl3)δ9.4025(d,J=9.2H Z ,1H),7.953(t,J=1.6H Z ,1H),7.812(m,2H).

[0600] ASAP MS spectrum analysis: C44H4D23F2N5: theoretical value 686, observed value 687.

[0601] [Chemical Formula 62]

[0602]

[0603] Compound 38317(40)

[0604] Under nitrogen flow, a dimethylformamide solution (50 mL) of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.77 g, 4.37 mmol), potassium carbonate (0.72 g, 5.24 mmol), and compound f (1.2 g, 1.75 mmol) was stirred at 120°C overnight. After the mixture was returned to room temperature, a saturated ammonium chloride solution was added for quenching, and the mixture was extracted with chloroform. The solvent was distilled off with an evaporator, and the mixture was purified by silica gel column chromatography (toluene:hexane) to obtain compound 38317 (40) (1.70 g, 1.704 mmol, yield 97.6%).

[0605] 1 H NMR (400 MH Z ,CDCl3)δ9.860(s,1H),6.989(t,J=1.6H Z ,1H),6.833(d,J=1.6H Z ,2H)

[0606] ASAP MS spectral analysis: C50HD31N6: theoretical value 997, observed value 998.

[0607] (Synthesis Example 4) Synthesis of Compound 46542 (1456)

[0608] [Chemical Formula 63]

[0609]

[0610] Compound g

[0611] Under a nitrogen atmosphere, at -85 ° C, a 1.0M tetrahydrofuran / hexane solution (9.68 mL, 9.68 mmol) of lithium diisopropylamide was added dropwise to a tetrahydrofuran solution (12.1 mL) of compound a (1.9 g, 9.68 mmol). After 1 hour, tetrahydrofuran (4.8 ml) obtained by dissolving iodine (2.46 g, 9.68 mmol) was added little by little. After returning to room temperature, sodium thiosulfate aqueous solution (10 wt %) was added for quenching. Then, it was extracted with ethyl acetate and washed with saturated brine. It was dried over anhydrous magnesium sulfate and filtered, and the obtained filtrate was concentrated. Recrystallization was carried out with dichloromethane to obtain compound g (1.72 g, 5.3 mmol, yield 55.1%) as a white solid.

[0612] 1 H NMR (400 MH Z ,CDCl3)δ8.43(dd,J=8.4H Z ,7.2,1H)

[0613] ASAP MS spectrum analysis: C11HD5F2IN: theoretical value 321, observed value 323.

[0614] [Chemical Formula 64]

[0615]

[0616] Compound h

[0617] Under a nitrogen atmosphere, carbazole-1,2,3,4,5,6,7,8-d8 (1.95 g, 11.1 mmol) and potassium carbonate (1.93 g, 13.9 mmol) were added to a mixture of compound g (1.5 g, 4.65 mmol) and dimethylformamide (46 mL), and stirred at 100 ° C for 15 hours. The reaction solution was cooled to room temperature, ion-exchanged water was added, and methanol was added and filtered. The obtained solid was reprecipitated with chloroform / methanol, further heated and washed with ethyl acetate and filtered. The obtained solid was reprecipitated with chloroform / hexane to obtain compound h (1.5 g, 2.3 mmol, yield 50.8%) as a white solid.

[0618] 1 H NMR (400 MH Z ,CDCl3)δ9.26(d,J=6.4H Z ,1H)

[0619] ASAP MS spectrum analysis: C35HD21IN3: theoretical value 632, observed value 633.

[0620] [Chemical Formula 65]

[0621]

[0622] Compound 46542(1456)

[0623] Under a nitrogen atmosphere, a 1.0 M solution of lithium diisopropylamide in tetrahydrofuran / hexane (2.6 mL, 2.6 mmol) was slowly added dropwise to a solution of compound h (1.5 g, 2.3 mmol) in tetrahydrofuran (9.5 mL) at -78°C. After stirring for 30 minutes, a 1 M solution of zinc chloride in tetrahydrofuran (7.1 mL, 7.1 mmol) was added, and the mixture was warmed to room temperature. After stirring for 1 hour, compound I (1.54 g, 2.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.11 mmol), and toluene (47 mL) were added, and the mixture was refluxed for 16 hours. The mixture was then cooled to room temperature, ion-exchanged water and methanol were added, and the resulting solid was filtered and washed with ethyl acetate, toluene, and dichloromethane to obtain compound 46542 (1456) (1.16 g, 1.26 mmol, 46% yield) as a yellow solid.

[0624] 1 H NMR (400 MH Z ,CDCl3)δ9.72(s,1H)

[0625] ASAP MS spectral analysis: C62HD38N7: theoretical value 919, observed value 920.

[0626] (Example 1) Preparation and evaluation of thin films

[0627] By vacuum evaporation method, the vacuum degree is less than 1×10 -3 Compound 46542 was evaporated on a quartz substrate under conditions of 1.5 Å / min Pa to form a pure thin film of compound 46542 with a thickness of 100 nm.

[0628] In addition, by vacuum evaporation method, the vacuum degree is less than 1×10 -3 Pa, compound 46542 and PyD2Cz of the following structure were evaporated from different evaporation sources on a quartz substrate to form a doped thin film with a thickness of 100 nm and a concentration of compound 46542 of 20 wt%.

[0629] Compound 46542(40), Compound 38317(40), Compound 46542(1456), Comparative Compound 1, and Comparative Compound 2 were used instead of Compound 46542, and pure and doped films were formed in the same manner.

[0630] When the formed doped thin films were irradiated with 300 nm excitation light, the photoluminescence was analyzed, and the ratio of the delayed fluorescence component and the lifetime (τ2) of the delayed fluorescence component were measured. Furthermore, the HOMO energy and LUMO energy were also measured using the formed pure thin films. The results are shown in the table below. As shown in the table below, the compound represented by general formula (1) was confirmed to have a shorter delayed fluorescence lifetime (τ2) than Comparative Compounds 1 and 2.

[0631] [Table 6]

[0632]

[0633] [Chemical Formula 66]

[0634]

[0635] (Example 2) Preparation and Evaluation of Organic Electroluminescent Element

[0636] By vacuum evaporation method, the vacuum degree is 5.0×10 -5 Pa stacked each thin film on a glass substrate with an anode composed of indium / tin oxide (ITO) with a film thickness of 50nm. First, HAT CN was formed on ITO with a thickness of 10nm, NPD was formed thereon with a thickness of 30nm, TrisPCz was further formed thereon with a thickness of 10nm, and DFCz was formed thereon with a thickness of 5nm. Then, DFCz and compound 46542 were co-evaporated from different evaporation sources to form a 40nm thick layer as a light-emitting layer. The concentration of compound 46542 in the light-emitting layer was set to 30wt%. Then, after SF3TRZ was formed with a thickness of 10nm, Liq and SF3TRZ were co-evaporated from different evaporation sources to form a 30nm thick layer. The concentrations of Liq and SF3TRZ in this layer were 30wt% and 70wt%, respectively. In addition, Liq was formed with a thickness of 2nm, and then aluminum (Al) was evaporated with a thickness of 100nm to form a cathode, which was used as an organic electroluminescent element.

[0637] Organic electroluminescent devices were prepared by the same procedure using Compound 46542(40), Compound 38317(40), Compound 46542(1456), Comparative Compound 1, and Comparative Compound 2, respectively, instead of Compound 46542.

[0638] The measured 2The time elapsed until the luminous intensity reached 95% of the initial luminous intensity (LT95) when each organic electroluminescent element was driven is shown in the table below. The LT95 values ​​in the table are shown as relative values ​​using the LT95 value of the comparative compound 2 as the reference (1). It was confirmed that the LT95 values ​​of each organic electroluminescent element using the compound represented by the general formula (1) were long, and the element life was improved.

[0639] [Table 7]

[0640] LT95 Compound 46542 3.3 Compound 46542(40) 2.6 Compound 38317(40) 3.3 Compound 46542(1456) 5.8 Comparative Compound 1 0.78 Comparative Compound 2 1

[0641] (Example 3) Preparation and Evaluation of Organic Electroluminescent Device Using an Assistant Dopant

[0642] An organic electroluminescent element was prepared by the same steps as in Example 2, except that the light-emitting layer in Example 2 was replaced by the following change: DFCz, compound 46542, and EM1 as a light-emitting material were evaporated in 69.5 wt %, 30.0 wt %, and 0.5 wt % respectively from different evaporation sources to form a 40 nm thick light-emitting layer.

[0643] In addition, instead of compound 46542, compound 46542(40), compound 38317(40), compound 46542(1456), comparative compound 1, and comparative compound 2 were used to prepare organic electroluminescent devices according to the same procedure.

[0644] When the compound represented by the general formula (1) is used as an auxiliary dopant, the device life is also improved.

[0645] [Chemical Formula 67]

[0646]

[0647] Industrial applicability

[0648] By using the compound represented by the general formula (1), an organic light-emitting device having excellent light-emitting properties can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): [Chemical Formula 1] General formula (1) In the general formula (1), X 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of them is N, R represents a hydrogen atom, a deuterium atom or a substituent, Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom, but Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom, L 1 represents a single bond or a divalent linking group, X 4 Indicates N or C(R 1 ), X 5 Indicates N or C(R 2 ), X 6 Indicates N or C(R 3 ), but X 4 ~X 6 Only one of them is N, R 1 ~R 5 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a donor group, and R 1 ~R 5 At least one of them is a donor group, R 1 ~R 5 0 to 2 of them are hydrogen atoms or deuterium atoms, R 1 ~R 5 0 to 1 of them are substituted or unsubstituted aryl groups.

2. The compound according to claim 1, wherein X 5 is N.

3. The compound according to claim 1, wherein X 6 is N.

4. The compound according to claim 1, wherein R 1 ~R 5 Only one of them is a substituted or unsubstituted aryl group.

5. The compound according to claim 4, wherein R 4 is a substituted or unsubstituted aryl group.

6. The compound according to claim 1, wherein R 1 ~R 5 One of them is a donor group.

7. The compound according to claim 1, wherein R 1 ~R 5 Two of them are donor groups.

8. The compound according to claim 1, wherein R 1 ~R 5 Three of them are donor groups.

9. The compound according to claim 1, wherein The donor group is a substituted or unsubstituted carbazole-9-yl group.

10. The compound according to claim 2, wherein R 3 ~R 5 are each independently a substituted or unsubstituted aryl group or a donor group.

11. The compound according to claim 3, wherein R 2 、R 4 and R 5 are each independently a substituted or unsubstituted aryl group or a donor group.

12. The compound according to claim 1, wherein X 1 ~X 3 is N.

13. The compound according to claim 1, wherein Ar 1 is a substituted or unsubstituted carbazole-9-yl group, Ar 2 is a substituted or unsubstituted aryl group.

14. The compound according to claim 1, wherein Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted carbazol-9-yl group.

15. The compound according to claim 1, wherein L 1 For a single bond.

16. The compound according to claim 2, wherein R 1 A hydrogen atom.

17. The compound of claim 1 having at least one deuterium atom.

18. A light-emitting material consisting of the compound according to any one of claims 1 to 17.

19. A delayed phosphor consisting of the compound according to any one of claims 1 to 17.

20. A film comprising the compound of any one of claims 1 to 17. 21 . An organic semiconductor device comprising the compound according to claim 1 . 22 . An organic light-emitting device comprising the compound according to claim 1 . 23 . The organic light-emitting element according to claim 22 , comprising a layer containing the compound, and the layer further containing a host material.

24. The organic light emitting element according to claim 23, wherein The layer containing the compound further contains a delayed fluorescent material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound. 25 . The organic light-emitting element according to claim 23 , comprising a layer containing the compound, and further comprising a light-emitting material having a structure different from that of the compound.

26. The organic light emitting element according to claim 23, wherein Among the materials included in the organic light-emitting element, the compound emits the largest amount of light.

27. The organic light emitting element according to claim 25, wherein The amount of luminescence from the light-emitting material is greater than the amount of luminescence from the compound. The organic light-emitting element according to claim 22 , which is an organic electroluminescent element. The organic light-emitting element according to claim 22 , which emits delayed fluorescence.

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