Organic electroluminescent composition and use thereof

Abstract

The present application relates to the technical field of display, in particular to an organic electroluminescent composition and application thereof. The organic electroluminescent composition provided by the present application comprises a first compound and a second compound, wherein the first compound comprises a compound represented by formula (I): and the second compound is a compound represented by formula (2): the organic electroluminescent device comprising the material has more excellent service life, and also has lower driving voltage and higher efficiency.

Description

Technical Field

[0001] This invention relates to the field of display technology, and more specifically to an organic electroluminescent composition and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) convert electrical energy into light by applying electricity to organic light-emitting materials, and typically consist of an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of an organic EL device can include hole injection layers, hole transport layers, hole auxiliary layers, light-emitting auxiliary layers, electron blocking layers, light-emitting layers (containing host materials and dopant materials), electron buffer layers, hole blocking layers, electron transport layers, and electron injection layers, etc. The materials used in the organic layer can be categorized according to their functions, such as hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In an organic EL device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and high-energy excitons are generated through the recombination of holes and electrons. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0003] Currently, the high driving voltage and short lifespan of organic light-emitting diodes (OLEDs) are caused by the low stability of organic functional materials and the imbalance of carrier mobility, which seriously limits the application of OLEDs. Summary of the Invention

[0004] The purpose of this invention is to overcome the shortcomings of existing organic electroluminescent materials, such as low stability and unbalanced carrier mobility, which result in high driving voltage and short lifespan of organic electroluminescent diodes, and to provide an organic electroluminescent material and its application.

[0005] In this invention, -* represents a connection key.

[0006] The solution adopted in this invention is as follows:

[0007] This invention provides an organic electroluminescent composition comprising a first compound and a second compound;

[0008] The first compound has the structure shown in formula (1):

[0009]

[0010] In equation (1),

[0011] X 4 X 5X 6 Selected from N;

[0012] X 1 X 2 X 3 Each independently selected from CR 1 CR 2 or CR 3 R 1 Selected from equation (1-1) or equation (1-2), R 2 Choose from equation (1-3) or equation (1-4);

[0013]

[0014] Where R 1 When R is selected from equation (1-1), 2 Not for equation (1-4), and R 3 Selected from substituted or unsubstituted C6-C12 aryl groups; when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C60 aryl groups;

[0015] Ar 1 Selected from substituted or unsubstituted C6-C60 aryl groups; n1 is selected from integers from 0 to 6;

[0016] Ar 2 Selected from substituted or unsubstituted C6-C60 aryl groups; n2 is selected from integers from 0 to 6;

[0017] Ar 3 Selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C1-C60 heteroaryl groups; n3 is selected from integers from 0 to 6;

[0018] Ar 4 Selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C1-C60 heteroaryl groups; n4 is selected from integers from 0 to 6;

[0019] The second compound has the structure shown in formula (2):

[0020]

[0021] in,

[0022] R 4 -L 1 Ar 5 R 5 -L 2 Ar 6 R 6 -L3 Ar 7 L 1 -L 3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene;

[0023] L 1 -L 3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene;

[0024] Ar 5 -Ar 7 Each is independently selected from hydrogen, deuterium, protium, tritium, halogen, cyano, substituted or unsubstituted C6-C60 aromatic amino group, substituted or unsubstituted C3-C60 heteroaryl amino group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, wherein Ar 5 -Ar 7 At least one of them is the structure shown in equation (II),

[0025]

[0026] R 7 -L 4 Ar 8 R 8 -L 5 Ar 9 ,

[0027] Among them, L 4 and L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene;

[0028] Ar 8 and Ar 9 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0029] X is selected from O, S, Se, NAr, CR 9 R 10 Wherein, Ar is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 4 and R 5 Each is independently selected from hydrogen atoms, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups;

[0030] The substituents in the substituted C6-C12 aryl, substituted C6-C60 aryl, substituted C1-C60 heteroaryl, substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C3-C60 heteroaryl, substituted C1-C20 alkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 arylamine, and substituted C3-C60 heteroarylamine are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0031] Understandable. R in equation (2) 4 Substitution can be performed on ring B or ring C, R 5 Substitution can be performed on ring D, R 6 It can be replaced on ring E.

[0032] Substituents

[0033] In this application, the term "substituent" has its common meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0034] Replaced or not replaced

[0035] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0036] The definition of "unsubstituted" is as follows: it refers to being replaced by hydrogen atoms, and the hydrogen atoms in this invention include protium, deuterium, and tritium.

[0037] C1-C60, C3-C60, C6-C60

[0038] In this application, C1-C60, C3-C60, and C6-C60 define the range of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms representing the aryl group can be any integer within the range of 6-60, such as 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, and 60.

[0039] alkyl

[0040] In this application, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0041] Aryl, aryl

[0042] In this application, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings may be interrupted by short non-aromatic units and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracene, fluorene, and spirodifluorene. Arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0043] heteroaryl, hypoaryl

[0044] In this application, the terms "hybrid aryl" and "heteroaryl" include monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, and benzyl. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyrroleyl. Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl Azolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, ininazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridyl, phenanthridyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0045] halogen

[0046] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0047] hydrogen

[0048] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0049] Substituents

[0050] Unless otherwise specified, the substituents in all other structures in this application are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0051] Organic electroluminescent composition

[0052] In this application, "organic electroluminescent composition" ” This refers to two or more materials that exist together or are prepared to exist together and can be used in an organic electroluminescent device. In this document, "existing together" means not only that the two or more materials are mixed, but also that the materials are separate. Furthermore, the compositional materials for an organic electroluminescent device are a concept that includes not only materials contained in the organic electroluminescent device before (e.g., before evaporation), but also materials contained in the organic electroluminescent device after (e.g., after evaporation). For example, the compositional material for an organic electroluminescent device may comprise two or more of the following: hole injection material, hole transport material, hole assist material, luminescence assist material, electron blocking material, luminescent material (both host material and dopant material); electron buffer material, hole blocking material, electron transport material, and electron injection material; or it may comprise two or more of the following: hole injection material, two or more of the following: hole transport material, two or more of the following: hole assist material, two or more of the following: luminescence assist material, two or more of the following: electron blocking material, two or more of the following: luminescent material (both host material and dopant material); two or more of the following: electron buffer material, two or more of the following: hole blocking material, two or more of the following: electron transport material, and two or more of the following: electron injection material. The compositional material for an organic electroluminescent device may be contained in any layer constituting the organic electroluminescent device. Two or more materials contained in the compositional material may be contained together in one layer, or they may each be contained in a separate layer. When two or more materials are contained in one layer, the layer may be formed by a co-evaporation method in which the materials are mixed, or by a co-evaporation method in which the materials are evaporated separately and simultaneously.

[0053] In this application, taking equation (1-1) as an example, D n1 This indicates that there are n1 D (deuterium) substitutions on the naphthyl group.

[0054] Preferably, the first compound has the structures shown in formulas (1-5) and (1-6):

[0055]

[0056] In the formula, R 3 Ar 1 Ar2 Ar 3 Ar 4 The definitions of n1 and n2 are the same as those described above.

[0057] Preferred, Ar 1 and Ar 2 They are identical or different, and each is independently selected from substituted or unsubstituted C6-C50 aryl groups.

[0058] The substituents in the substituted C6-C50 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C50 aromatic amino, and C3-C50 heteroaryl.

[0059] Preferred, Ar 1 and Ar 2 The same or different, and each independently selected from substituted or unsubstituted C6-C25 aryl groups,

[0060] The substituents in the substituted C6-C25 aryl group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C25 aromatic amino, and C3-C25 heteroaromatic amino.

[0061] Preferred, Ar 1 and Ar 2 They may be the same or different, and each is independently selected from substituted or unsubstituted C6-C12 aryl groups.

[0062] The substituents in the substituted C6-C12 aryl group are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C6-C12 aryl, and C1-C12 heteroaryl.

[0063] Preferred, Ar 1 and Ar 2 The same or different, and each independently selected from substituted or unsubstituted naphthyl groups,

[0064] The substituents in the substituted naphthyl group are selected from deuterium.

[0065] Preferably, the first compound has the following structure:

[0066]

[0067] Among them, R 3 Ar 3 Ar4 The definitions of n1, n2, n3, and n4 are the same as those described above; n5 to n8 are selected from integers from 0 to 7;

[0068] Preferably, n5 to n8 are each independently selected from integers from 0 to 6;

[0069] Preferably, n5 to n8 are each independently selected from integers from 0 to 5;

[0070] Preferably, n5 to n8 are each independently selected from integers from 0 to 4;

[0071] Preferably, n5 to n8 are each independently selected from integers from 0 to 3;

[0072] Preferably, n5 to n8 are each independently selected from integers from 0 to 2.

[0073] Preferred, Ar 3 and Ar 4 They are either the same or different, and each is independently selected from substituted or unsubstituted C6-C50 aryl groups or substituted or unsubstituted C1-C50 heteroaryl groups.

[0074] Wherein, the substituents in the substituted C6-C50 aryl and substituted C6-C50 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C50 heteroaryl.

[0075] Preferred, Ar 3 and Ar 4 They are identical or different, and each is independently selected from substituted or unsubstituted C6-C25 aryl or substituted or unsubstituted C6-C25 heteroaryl.

[0076] Wherein, the substituents in the substituted C6-C25 aryl and substituted C6-C25 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C25 aromatic amino, and C3-C25 heteroaromatic amino.

[0077] Preferred, Ar 3 and Ar 4 They are either the same or different, and each is independently selected from the group consisting of the following groups:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] Preferably, when R 1 When R is selected from equation (1-1), 2 Not for equation (1-4), and R 3 Selected from the group consisting of the following groups:

[0084]

[0085]

[0086] Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C50 aryl groups,

[0087] The substituents in the substituted C6-C50 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0088] Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C25 aryl groups;

[0089] The substituents in the substituted C6-C25 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, and C3-C25 heteroaryl.

[0090] Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from the group consisting of the following groups:

[0091]

[0092]

[0093] Understandably, in this application, For example, D1-D5 indicates that there are 1, 2, 3, 4 or 5 deuterium substitutions on the benzene ring.

[0094] Preferably, n1 to n4 are each independently selected from integers from 0 to 5;

[0095] Preferably, n1 to n4 are each independently selected from integers from 0 to 4;

[0096] Preferably, n1 to n4 are each independently selected from integers from 0 to 3;

[0097] Preferably, n1 to n4 are each independently selected from integers from 0 to 2.

[0098] Preferably, the first compound is selected from one of the following structures:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] The present invention also provides a method for synthesizing the above-mentioned first compound, the synthetic route of which is shown below:

[0125] General formula for the synthesis of intermediate A:

[0126]

[0127] General formula for the synthesis of intermediate B:

[0128]

[0129] General formula for the synthesis of compound N:

[0130]

[0131] In the formula, X and Y are halogens; R 3 Ar 1 Ar 2 Ar 3 Ar 4 The definitions of n1, n2, n3, and n4 are the same as those above.

[0132] Preferably, in the second compound, L 1 -L 3 For connecting bonds, substituted or unsubstituted C6-C15 arylene, substituted or unsubstituted C3-C15 heteroarylene;

[0133] The substituents in the substituted C6-C15 arylene and the substituted C3-C15 heteroarylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0134] Preferred, L 1 -L 3 Each is independently selected from the linking bond, phenylene, naphthylene, triphenylene, and biphenylene;

[0135] Preferred, L 1 Selected from the link key, L 2 Selected from phenylene, naphthylene, triphenylene, biphenylene, L 3 For connection key;

[0136] Preferred, L 1 -L 3 Each is independently selected from a single key.

[0137] Preferred, Ar 5 -Ar 7 At least one of them is the structure shown in equation (II). If not all of them are the structure shown in equation (II), the remaining Ar 5 -Ar 7 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0138] The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0139] Preferred, Ar 5 -Ar 7 At least one of them is the structure shown in equation (II). If not all of them are the structure shown in equation (II), the remaining Ar 5 -Ar 7 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl;

[0140] The substituents in the substituted dibenzofuranyl and substituted dibenzothiopheneyl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0141] Understandable, Ar 5 -Ar 7 At least one of them is the structure represented by equation (II) representing Ar. 5 -Ar 7 One, two, or three of them are the structures shown in equation (II).

[0142] Preferred, L 4 and L 5 For connecting bonds, substituted or unsubstituted C6-C15 arylene groups;

[0143] The substituents in the substituted C6-C15 arylene groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0144] Preferred, L 4 and L 5 Each is independently selected from single bonds, phenylene, and naphthylene;

[0145] Preferred, L 4 and L 5 Each is independently selected from a single key.

[0146] Preferably, Ar is selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0147] The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0148] Preferably, Ar is selected from substituted or unsubstituted group A, and group A is selected from: phenyl, naphthyl, biphenyl, terphenyl, triphenylene. Dibenzofuranyl, dibenzothiophene;

[0149] Wherein, the substituent in the substituted group A is one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0150] Preferred, R 9 and R 10 Each is independently selected from substituted or unsubstituted C1-C5 alkyl groups and substituted or unsubstituted C6-C30 aryl groups;

[0151] The substituents in the substituted C1-C5 alkyl and substituted C6-C30 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0152] Preferred, Ar 8 -Ar 9Each group is independently selected from substituted or unsubstituted group B, where group B is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, etc. alkyl, dibenzofuranyl, benzonaphthiofuranyl, dibenzothiophenyl, dibenzoselenophenolyl, triphenylene, dimethylfluorenyl, spirodifluorenyl, fluoranyl, carbazoleyl, phenylcarbazoleyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, pyridyl, pyrimidinyl, triazineyl;

[0153] Wherein, the substituents in the substituted group B are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0154] Preferred, Ar 8 and Ar 9 Each independently selected

[0155]

[0156] Among them, R T1 -R T6 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, or R T1 -R T5 Any two adjacent elements can fuse to form a C6-C30 ring A; Y is selected from O, S, NAr, and CR. 9 R 10 ;Among them, Ar and R 9 R 10 The definition is the same as the definition above;

[0157] When there are multiple R T1 -R T6 At that time, R T1 -R T6 Each is independent of the others and may be the same or different;

[0158] The substituents in the substituted C1-C30 alkyl, substituted C7-C30 aralkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C4-C30 heteroaryl, substituted C3-C30 cycloalkyl, substituted C3-C30 heterocycloalkyl, substituted C3-C30 cycloalkenyl, substituted C1-C30 alkoxy, and substituted C6-C30 aryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0159] Preferably, ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, and substituted or unsubstituted phenanthrene rings;

[0160] The substituents in the substituted benzene ring, substituted naphthyl ring, and substituted phenanthrene ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0161] Preferably, the second compound has the structure shown below;

[0162]

[0163]

[0164] Among them, R 4 R 5 R 6 R 7 R 8 L 1 L 2 L 3 Same as defined above. Preferably, the second compound has the following structure:

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] Preferably, the mass ratio of the first compound to the second compound is 1:9-9:1;

[0204] Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 2:8-8:2;

[0205] Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 3:7-7:3;

[0206] Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 4:6 to 6:4.

[0207] The present invention also provides an organic electroluminescent host material composition comprising the composition described above for organic optoelectronic devices.

[0208] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises the organic electroluminescent composition as described above or the organic electroluminescent host material composition as described above;

[0209] Preferably, the organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an organic electroluminescent composition as described above or an organic electroluminescent host material composition as described above.

[0210] Preferably, the first electrode is the anode and the second electrode is the cathode.

[0211] Preferably, the organic layer can be composed of a single-layer structure or a multi-layer structure with two or more layers stacked on top of each other. For example, the organic electroluminescent device may include one or more of the following sequentially arranged layers: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0212] Preferably, the light-emitting layer comprises an organic electroluminescent composition as described above or an organic electroluminescent host material composition as described above.

[0213] Preferably, the organic electroluminescent device may be, for example, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode sequentially stacked on a substrate.

[0214] Preferably, the anode comprises an anode material, preferably a material with a large work function that facilitates hole injection into the first hole transport layer. For example, the anode material may include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0215] Preferably, the hole injection layer is used to enhance the ability to inject holes into the hole transport layer. The hole injection layer can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer can be selected from, for example, the following compounds or any combination thereof:

[0216]

[0217]

[0218] Preferably, the hole transport layer may include one or more hole transport materials. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The material of the hole transport layer may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this. The material of the hole transport layer may, for example, be selected from the following compounds or any combination thereof:

[0219]

[0220]

[0221] Preferably, the light-emitting layer is a material capable of receiving holes and electrons from the hole transport layer and the electron transport layer respectively, and combining them to emit light in the visible light region.

[0222] Preferably, the light-emitting layer can be composed of a single light-emitting material, or it can include a host material and a guest material. For example, the light-emitting layer includes a host material and a guest material. Holes injected into the light-emitting layer and then electrons injected into the light-emitting layer can recombine in the light-emitting layer to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby causing the guest material to emit light.

[0223] Preferably, the host material of the light-emitting layer may include metal chelating compounds, bis(phenylacetyl) derivatives, aromatic amine derivatives, dibenzofuran derivatives, and other types of materials. For example, the host material may include organic electroluminescent compositions as described above or light-emitting host material compositions for organic optoelectronic devices as described above.

[0224] Preferably, the guest material of the luminescent layer may comprise a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other types of materials, which are not limited herein by this application. The guest material is also referred to as a dopant or dopant, and can be classified into fluorescent dopant and phosphorescent dopant according to the type of luminescence.

[0225] Preferably, the electron transport layer can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode, transports electrons to the light-emitting layer, and suppresses hole transfer from the light-emitting layer. The electron transport material is suitably one that can effectively receive electron injection from the cathode and transfer electrons to the light-emitting layer, and has a high electron mobility. The electron transport layer may be selected from, but is not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but is not limited to these.

[0226] Preferably, the electron transport layer includes, but is not limited to, the following structures:

[0227]

[0228] Preferably, the electron injection layer is used to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives; inorganic materials such as alkali metal sulfides and alkali metal halides; or may include complexes of alkali metals and organic compounds.

[0229] Preferably, the cathode is a material with a small work function that facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0230] The present invention also provides an application of the organic electroluminescent device as described above in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors or dye lasers.

[0231] The beneficial effects of this invention are:

[0232] In the organic electroluminescent composition provided by the present invention, the first compound comprises the compound represented by formula (1), and the second compound comprises the compound represented by formula (2). The interaction between the compound represented by formula (1) and the compound represented by formula (2) facilitates the matching of HOMO and LUMO energy levels with adjacent energy levels, thereby enabling the organic electroluminescent composition to obtain higher stability and more balanced carrier mobility. As a result, the organic electroluminescent device containing the composition has a better lifetime, as well as a lower driving voltage and higher efficiency. Attached Figure Description

[0233] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0234] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0235] Wherein, 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. Detailed Implementation

[0236] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0237] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0238] Synthesis of intermediate A1:

[0239]

[0240] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add the following ingredients in sequence: SA1 (1.0 mmol), 1-naphthoboronic acid RA1 (1.1 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate A1-1 (yield 82%).

[0241] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1-1 (1 mmol), pinacol diboronate (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol), and 1,4-dioxane (10 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate A1-2 (yield 78%).

[0242] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1-2 (1 mmol), EA1 (1.2 mmol), Pd(PPh3)2Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 45 °C and react for 4 h. After the reaction is complete, cool to room temperature, filter, and wash the filter cake twice with deionized water. The crude product is then purified twice by recrystallization from ethyl acetate and tetrahydrofuran to obtain compound A1 (70% yield).

[0243] Intermediate A2 to intermediate An are synthesized using the same method as intermediate A1, the difference being the substitution of related raw materials. For details, please refer to Table 1 for the raw material table for the synthesis of intermediates A2 to intermediate An.

[0244] Table 1. Raw materials for the synthesis of intermediates A2 to An

[0245]

[0246]

[0247]

[0248] Synthesis of intermediate B1

[0249]

[0250] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add the following ingredients in sequence: SB1 (1.0 mmol), phenylboronic acid RB1 (1.1 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate B1-1 (yield 85%).

[0251] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate B1-1 (1 mmol), pinacol diboronate (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol), and 1,4-dioxane (10 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate B1 (yield 76%).

[0252] Intermediates B2 to Bn are synthesized using the same method as intermediate B1, with the difference being the substitution of relevant raw materials. For details, please refer to Table 2 for the raw material table for the synthesis of intermediates B2 to Bn.

[0253] Table 2. Raw material list for the synthesis of intermediates B2 to Bn

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262] Synthesis Example 1

[0263] This embodiment provides the synthesis of N-4, and its synthetic route is shown below:

[0264]

[0265] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B1 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-4 (yield 65%).

[0266] Elemental analysis: C 45 H 29 Theoretical N3 values: C, 88.35; H, 4.78; N, 6.87; Measured values: C, 88.33; H, 4.79; N, 6.88; HRMS(ESI) m / z [M+H] + Theoretical value: 611.75; Measured value: 612.73.

[0267] Synthesis Example 2

[0268] This embodiment provides the synthesis of N-20, and its synthetic route is shown below:

[0269]

[0270] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B20 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-20 (yield 63%).

[0271] Elemental analysis: C 49 H 31 N3. Theoretical values: C, 88.93; H, 4.72; N, 6.35; Measured values: C, 88.95; H, 4.71; N, 6.34; HRMS(ESI) m / z [M+H] + Theoretical value: 661.81; Measured value: 662.83.

[0272] Synthesis Example 3

[0273] This embodiment provides the synthesis of N-38, and its synthetic route is shown below:

[0274]

[0275] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B38 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-38 (yield 67%).

[0276] Elemental analysis: C 57H 35 N3. Theoretical values: C, 89.85; H, 4.63; N, 5.52; Measured values: C, 89.87; H, 4.62; N, 5.51; HRMS(ESI) m / z [M+H] + Theoretical value: 761.93; Measured value: 762.91.

[0277] Synthesis Example 4

[0278] This embodiment provides the synthesis of N-47, and its synthetic route is shown below:

[0279]

[0280] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B47 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-47 (yield 68%).

[0281] Elemental analysis: C 51 H 31 N₃O. Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.25; H, 4.46; N, 6.02; HRMS(ESI) m / z [M+H] + Theoretical value: 701.83; Measured value: 702.85.

[0282] Synthesis Example 5

[0283] This embodiment provides the synthesis of N-73, and its synthetic route is shown below:

[0284]

[0285] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B73 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-73 (yield 72%).

[0286] Elemental analysis: C 53 H 33N5. Theoretical values: C, 86.04; H, 4.50; N, 9.47; Measured values: C, 86.07; H, 4.48; N, 9.46; HRMS(ESI) m / z[M+H]+: Theoretical value: 739.88; Measured value: 740.85.

[0287] Synthesis Example 6

[0288] This embodiment provides the synthesis of N-82, and its synthetic route is shown below:

[0289]

[0290] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B82 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-82 (yield 64%).

[0291] Elemental analysis: C 51 H 33 N3. Theoretical values: C, 89.05; H, 4.84; N, 6.11; Measured values: C, 89.07; H, 4.83; N, 6.10; HRMS(ESI) m / z [M+H] + Theoretical value: 687.85; Measured value: 688.82.

[0292] Synthesis Example 7

[0293] This embodiment provides the synthesis of N-107, and its synthetic route is shown below:

[0294]

[0295] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B107 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-107 (yield 67%).

[0296] Elemental analysis: C 57 H 35N₃O. Theoretical values: C, 88.01; H, 4.54; N, 5.40; O, 2.06; Measured values: C, 88.04; H, 4.53; N, 5.38; HRMS(ESI) m / z [M+H] + Theoretical value: 777.93; Measured value: 778.92.

[0297] Synthesis Example 8

[0298] This embodiment provides the synthesis of N-119, and its synthetic route is shown below:

[0299]

[0300] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A119 (1 mmol), B1 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-119 (yield 67%).

[0301] Elemental analysis: C 45 H 22 D7N3. Theoretical values: C, 87.35; H, 5.86; N, 6.79; Measured values: C, 87.35; H, 5.86; N, 6.79; HRMS(ESI) m / z [M+H] + Theoretical value: 618.79; Measured value: 619.77.

[0302] Synthesis Example 9

[0303] This embodiment provides the synthesis of N-120, and its synthetic route is shown below:

[0304]

[0305] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A120 (1 mmol), B20 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-120 (yield 69%).

[0306] Elemental analysis: C 45 H 23D6N3. Theoretical values: C, 87.49; H, 5.71; N, 6.80; Measured values: C, 87.47; H, 5.72; N, 6.81; HRMS(ESI) m / z [M+H] + Theoretical value: 617.78; Measured value: 618.76.

[0307] Synthesis Example 10

[0308] This embodiment provides the synthesis of N-121, and its synthetic route is shown below:

[0309]

[0310] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B121 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-121 (yield 61%).

[0311] Elemental analysis: C 45 H 24 D5N3. Theoretical values: C, 87.63; H, 5.56; N, 6.81; Measured values: C, 87.65; H, 5.55; N, 6.80; HRMS(ESI) m / z [M+H] + Theoretical value: 616.78; Measured value: 617.75.

[0312] Synthesis Example 11

[0313] This embodiment provides the synthesis of N-163, and its synthetic route is shown below:

[0314]

[0315] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B163 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-163 (yield 63%).

[0316] Elemental analysis: C 55 H 33N₃O. Theoretical values: C, 87.86; H, 4.42; N, 5.59; O, 2.13; Measured values: C, 87.83; H, 4.43; N, 5.61; HRMS(ESI) m / z [M+H] + Theoretical value: 751.89; Measured value: 752.87.

[0317] Synthesis Example 12

[0318] This embodiment provides the synthesis of N-28, and its synthetic route is shown below:

[0319]

[0320] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B28 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-28 (yield 64%).

[0321] Elemental analysis: C 53 H 33 N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.44; H, 4.68; N, 5.87; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.24.

[0322] Synthesis Example 13

[0323] This embodiment provides the synthesis of N-31, and its synthetic route is shown below:

[0324]

[0325] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B31 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-31 (yield 62%).

[0326] Elemental analysis: C 53 H 33N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.43; H, 4.68; N, 5.88; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.31.

[0327] Synthesis Example 14

[0328] This embodiment provides the synthesis of N-33, and its synthetic route is shown below:

[0329]

[0330] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B33 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-33 (yield 60%).

[0331] Elemental analysis: C 53 H 33 N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.44; H, 4.66; N, 5.89; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.25.

[0332] Synthesis Example 15

[0333] This embodiment provides the synthesis of N-37, and its synthetic route is shown below:

[0334]

[0335] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B37 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-37 (yield 61%).

[0336] Elemental analysis: C 57 H 35N3. Theoretical values: C, 89.85; H, 4.63; N, 5.52; Measured values: C, 89.86; H, 4.64; N, 5.50; HRMS(ESI) m / z [M+H] + Theoretical value: 761.28; Measured value: 762.14.

[0337] Synthesis Example 16

[0338] This embodiment provides the synthesis of N-54, and its synthetic route is shown below:

[0339]

[0340] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B54 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-54 (yield 63%).

[0341] Elemental analysis: C 51 H 31 N3S. Theoretical values: C, 85.33; H, 4.35; N, 5.85; S, 4.47; Measured values: C, 85.34; H, 4.36; N, 5.84; S, 4.46; HRMS(ESI) m / z [M+H] + Theoretical value: 717.22; Measured value: 718.34.

[0342] Synthesis Example 17

[0343] This embodiment provides the synthesis of N-61, and its synthetic route is shown below:

[0344]

[0345] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B61 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-61 (yield 59%).

[0346] Elemental analysis: C 55 H 33N₃O. Theoretical values: C, 87.86; H, 4.42; N, 5.59; O, 2.13; Measured values: C, 87.87; H, 4.43; N, 5.57; HRMS(ESI) m / z [M+H] + Theoretical value: 751.26; Measured value: 752.24.

[0347] Synthesis Example 18

[0348] This embodiment provides the synthesis of N-75, and its synthetic route is shown below:

[0349]

[0350] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B75 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-75 (yield 62%).

[0351] Elemental analysis: C 48 H 30 N4. Theoretical values: C, 86.98; H, 4.56; N, 8.45; Measured values: C, 86.99; H, 4.57; N, 8.43; HRMS(ESI) m / z [M+H] + Theoretical value: 662.25; Measured value: 663.21.

[0352] Synthesis Example 19

[0353] This embodiment provides the synthesis of N-96, and its synthetic route is shown below:

[0354]

[0355] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B96 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) in sequence. Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-96 (yield 66%).

[0356] Elemental analysis: C 55 H 35N3. Theoretical values: C, 89.52; H, 4.78; N, 5.69; Measured values: C, 89.54; H, 4.79; N, 5.66; HRMS(ESI) m / z [M+H] + Theoretical value: 737.28; Measured value: 738.21.

[0357] Synthesis Example 20

[0358] This embodiment provides the synthesis of N-112, and its synthetic route is shown below:

[0359]

[0360] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B112 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-112 (yield 67%).

[0361] Elemental analysis: C 57 H 35 N₃O. Theoretical values: C, 88.01; H, 4.54; N, 5.40; O, 2.06; Measured values: C, 88.00; H, 4.53; N, 5.38; HRMS(ESI) m / z [M+H] + Theoretical value: 777.28; Measured value: 778.14.

[0362] Synthesis Example 21

[0363] This embodiment provides the synthesis of N-160, and its synthetic route is shown below:

[0364]

[0365] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B160 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-160 (yield 60%).

[0366] Elemental analysis: C 55 H 27D6N3O. Theoretical values: C, 87.16; H, 5.19; N, 5.54; O, 2.11; Measured values: C, 87.18; H, 5.18; N, 5.53; HRMS(ESI) m / z [M+H] + Theoretical value: 757.30; Measured value: 758.32.

[0367] Synthesis Example 22

[0368] This embodiment provides the synthesis of N-167, and its synthetic route is shown below:

[0369]

[0370] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A119 (1 mmol), B167 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-167 (yield 66%).

[0371] Elemental analysis: C 44 H 21 D7N4. Theoretical values: C, 85.27; H, 5.69; N, 9.04; Measured values: C, 85.28; H, 5.70; N, 9.02; HRMS(ESI) m / z [M+H] + Theoretical value: 619.28; Measured value: 620.13.

[0372] Synthesis Example 23

[0373] This embodiment provides the synthesis of N-183, and its synthetic route is shown below:

[0374]

[0375] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A1 (1 mmol), B183 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-183 (yield 68%).

[0376] Elemental analysis: C 51 H 24D9N3. Theoretical values: C, 87.90; H, 6.07; N, 6.03; Measured values: C, 87.91; H, 6.08; N, 6.01; HRMS(ESI) m / z [M+H] + Theoretical value: 696.32; Measured value: 697.33.

[0377] Synthesis Example 24

[0378] This embodiment provides the synthesis of N-205, and its synthetic route is shown below:

[0379]

[0380] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A119 (1 mmol), B205 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-205 (yield 67%).

[0381] Elemental analysis: C 55 H 28 D7N3. Theoretical values: C, 88.68; H, 5.68; N, 5.64; Measured values: C, 88.69; H, 5.69; N, 5.62; HRMS(ESI) m / z [M+H] + Theoretical value: 744.33; Measured value: 745.15.

[0382] Synthesis Example 25

[0383] This embodiment provides the synthesis of N-221, and its synthetic route is shown below:

[0384]

[0385] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A221 (1 mmol), B221 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-221 (yield 62%).

[0386] Elemental analysis: C 45 H 29N3. Theoretical values: C, 88.35; H, 4.78; N, 6.87; Measured values: C, 88.36; H, 4.79; N, 6.85; HRMS(ESI) m / z [M+H] + Theoretical value: 611.24; Measured value: 612.33.

[0387] Synthesis Example 26

[0388] This embodiment provides the synthesis of N-229, and its synthetic route is shown below:

[0389]

[0390] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A229 (1 mmol), B229 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-229 (yield 63%).

[0391] Elemental analysis: C 49 H 24 D7N3. Theoretical values: C, 87.99; H, 5.72; N, 6.28; Measured values: C, 88.01; H, 5.71; N, 6.27; HRMS(ESI) m / z [M+H] + Theoretical value: 668.30; Measured value: 669.21.

[0392] Synthesis Example 27

[0393] This embodiment provides the synthesis of N-235, and its synthetic route is shown below:

[0394]

[0395] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A235 (1 mmol), B235 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-235 (yield 64%).

[0396] Elemental analysis: C 49 H 25D6N3. Theoretical values: C, 88.13; H, 5.58; N, 6.29; Measured values: C, 88.15; H, 5.57; N, 6.28; HRMS(ESI) m / z [M+H] + Theoretical value: 667.29; Measured value: 668.14.

[0397] Synthesis Example 28

[0398] This embodiment provides the synthesis of N-244, and its synthetic route is shown below:

[0399]

[0400] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A244 (1 mmol), B244 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-244 (yield 65%).

[0401] Elemental analysis: C 53 H 33 N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.44; H, 4.66; N, 5.89; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.24.

[0402] Synthesis Example 29

[0403] This embodiment provides the synthesis of N-261, and its synthetic route is shown below:

[0404]

[0405] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A221 (1 mmol), B261 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-261 (yield 60%).

[0406] Elemental analysis: C 51 H 31N₃O. Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.29; H, 4.46; N, 5.97; HRMS(ESI) m / z [M+H] + Theoretical value: 701.25; Measured value: 702.19.

[0407] Synthesis Example 30

[0408] This embodiment provides the synthesis of N-281, and its synthetic route is shown below:

[0409]

[0410] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A229 (1 mmol), B281 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-281 (yield 62%).

[0411] Elemental analysis: C 57 H 28 D7N3. Theoretical values: C, 89.03; H, 5.50; N, 5.46; Measured values: C, 89.04; H, 5.51; N, 5.44; HRMS(ESI) m / z [M+H] + Theoretical value: 768.33; Measured value: 769.23.

[0412] Synthesis Example 31

[0413] This embodiment provides the synthesis of N-289, and its synthetic route is shown below:

[0414]

[0415] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A221 (1 mmol), B289 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-289 (yield 61%).

[0416] Elemental analysis: C 51 H 33N3. Theoretical values: C, 89.05; H, 4.84; N, 6.11; Measured values: C, 89.07; H, 4.83; N, 6.10; HRMS(ESI) m / z [M+H] + Theoretical value: 687.27; Measured value: 688.15.

[0417] Synthesis Example 32

[0418] This embodiment provides the synthesis of N-308, and its synthetic route is shown below:

[0419]

[0420] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A229 (1 mmol), B308 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-308 (yield 66%).

[0421] Elemental analysis: C 55 H 28 D7N3. Theoretical values: C, 88.68; H, 5.68; N, 5.64; Measured values: C, 88.69; H, 5.69; N, 5.62; HRMS(ESI) m / z [M+H] + Theoretical value: 744.33; Measured value: 745.32.

[0422] Synthesis Example 33

[0423] This embodiment provides the synthesis of N-313, and its synthetic route is shown below:

[0424]

[0425] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A229 (1 mmol), B313 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-313 (yield 64%).

[0426] Elemental analysis: C 55 H 28D7N3. Theoretical values: C, 88.68; H, 5.68; N, 5.64; Measured values: C, 88.69; H, 5.69; N, 5.62; HRMS(ESI) m / z [M+H] + Theoretical value: 744.33; Measured value: 745.23.

[0427] Synthesis Example 34

[0428] This embodiment provides the synthesis of N-344, and its synthetic route is shown below:

[0429]

[0430] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A229 (1 mmol), B344 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-344 (yield 65%).

[0431] Elemental analysis: C 59 H 30 D7N3. Theoretical values: C, 89.14; H, 5.58; N, 5.29; Measured values: C, 89.16; H, 5.59; N, 5.26; HRMS(ESI) m / z [M+H] + Theoretical value: 794.34; Measured value: 795.16.

[0432] Synthesis Example 35

[0433] This embodiment provides the synthesis of N-356, and its synthetic route is shown below:

[0434]

[0435] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A235 (1 mmol), B356 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-356 (yield 60%).

[0436] Elemental analysis: C 44 H 22D6N4. Theoretical values: C, 85.41; H, 5.54; N, 9.05; Measured values: C, 85.43; H, 5.53; N, 9.04; HRMS(ESI) m / z [M+H] + Theoretical value: 618.27; Measured value: 619.16.

[0437] Synthesis Example 36

[0438] This embodiment provides the synthesis of N-363, and its synthetic route is shown below:

[0439]

[0440] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A235 (1 mmol), B363 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-363 (yield 59%).

[0441] Elemental analysis: C 48 H 24 D6N4. Theoretical values: C, 86.20; H, 5.42; N, 8.38; Measured values: C, 86.22; H, 5.43; N, 8.35; HRMS(ESI) m / z [M+H] + Theoretical value: 668.28; Measured value: 669.34.

[0442] Synthesis Example 37

[0443] This embodiment provides the synthesis of N-370, and its synthetic route is shown below:

[0444]

[0445] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A235 (1 mmol), B370 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-370 (yield 57%).

[0446] Elemental analysis: C 52 H 26D6N4. Theoretical values: C, 86.88; H, 5.33; N, 7.79; Measured values: C, 86.89; H, 5.35; N, 7.76; HRMS(ESI) m / z [M+H] + Theoretical value: 718.30; Measured value: 719.19.

[0447] Synthesis Example 38

[0448] This embodiment provides the synthesis of N-374, and its synthetic route is shown below:

[0449]

[0450] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A374 (1 mmol), B221 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-374 (yield 64%).

[0451] Elemental analysis: C 54 H 30 D7N3. Theoretical values: C, 88.25; H, 6.03; N, 5.72; Measured values: C, 88.26; H, 6.04; N, 5.70; HRMS(ESI) m / z [M+H] + Theoretical value: 734.34; Measured value: 735.22.

[0452] Synthesis Example 39

[0453] This embodiment provides the synthesis of N-382, and its synthetic route is shown below:

[0454]

[0455] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A382 (1 mmol), B382 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-382 (yield 63%).

[0456] Elemental analysis: C 53 H 33N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.44; H, 4.66; N, 5.89; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.14.

[0457] Synthesis Example 40

[0458] This embodiment provides the synthesis of N-383, and its synthetic route is shown below:

[0459]

[0460] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A383 (1 mmol), B383 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-383 (yield 61%).

[0461] Elemental analysis: C 57 H 28 D7N3. Theoretical values: C, 89.03; H, 5.50; N, 5.46; Measured values: C, 89.05; H, 5.51; N, 5.43; HRMS(ESI) m / z [M+H] + Theoretical value: 768.33; Measured value: 769.17.

[0462] Synthesis Example 41

[0463] This embodiment provides the synthesis of N-401, and its synthetic route is shown below:

[0464]

[0465] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A401 (1 mmol), B401 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-401 (yield 60%).

[0466] Elemental analysis: C 53 H 33N3. Theoretical values: C, 89.42; H, 4.67; N, 5.90; Measured values: C, 89.41; H, 4.65; N, 5.87; HRMS(ESI) m / z [M+H] + Theoretical value: 711.27; Measured value: 712.14.

[0467] Synthesis Example 42

[0468] This embodiment provides the synthesis of N-404, and its synthesis route is shown below:

[0469]

[0470] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A404 (1 mmol), B404 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-404 (yield 65%).

[0471] Elemental analysis: C 53 H 26 D7N3. Theoretical values: C, 88.55; H, 5.61; N, 5.85; Measured values: C, 88.56; H, 5.63; N, 5.82; HRMS(ESI) m / z [M+H] + Theoretical value: 718.31; Measured value: 719.22.

[0472] Synthesis Example 43

[0473] This embodiment provides the synthesis of N-415, and its synthetic route is shown below:

[0474]

[0475] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A401 (1 mmol), B415 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-415 (yield 59%).

[0476] Elemental analysis: C 51 H 31N3S. Theoretical values: C, 85.33; H, 4.35; N, 5.85; S, 4.47; Measured values: C, 85.35; H, 4.36; N, 5.84; S, 4.45; HRMS(ESI) m / z [M+H] + Theoretical value: 717.22; Measured value: 718.12.

[0477] Synthesis Example 44

[0478] This embodiment provides the synthesis of N-428, and its synthetic route is shown below:

[0479]

[0480] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A404 (1 mmol), B428 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-428 (yield 58%).

[0481] Elemental analysis: C 55 H 26 D7N3O. Theoretical values: C, 87.04; H, 5.31; N, 5.54; O, 2.11; Measured values: C, 87.05; H, 5.32; N, 5.52; HRMS(ESI) m / z [M+H] + Theoretical value: 758.31; Measured value: 759.35.

[0482] Synthesis Example 45

[0483] This embodiment provides the synthesis of N-438, and its synthetic route is shown below:

[0484]

[0485] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A438 (1 mmol), B438 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-438 (yield 59%).

[0486] Elemental analysis: C 57H 29 D6N3. Theoretical values: C, 89.15; H, 5.38; N, 5.47; Measured values: C, 89.16; H, 5.39; N, 5.45; HRMS(ESI) m / z [M+H] + Theoretical value: 767.32; Measured value: 768.25.

[0487] Synthesis Example 46

[0488] This embodiment provides the synthesis of N-499, and its synthetic route is shown below:

[0489]

[0490] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate A499 (1 mmol), B382 (1.1 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 hours. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain compound N-499 (yield 65%).

[0491] Elemental analysis: C 51 H 33 N3. Theoretical values: C, 89.05; H, 4.84; N, 6.11; Measured values: C, 89.07; H, 4.83; N, 6.10; HRMS(ESI) m / z [M+H] + Theoretical value: 687.27; Measured value: 688.09.

[0492] Device Examples

[0493] The materials used to prepare the following device embodiments or device comparative examples are shown in Table 3 below.

[0494] Table 3. Some compounds used in device examples or device comparison examples.

[0495]

[0496]

[0497] Device Example 1

[0498] This embodiment provides an organic electroluminescent device, such as... Figure 1As shown, the device includes an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are sequentially stacked on a substrate 1. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0499] The specific preparation process is as follows:

[0500] 1) Substrate cleaning:

[0501] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0502] 2) Preparation of organic layer:

[0503] The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL) / light emission layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0504] in:

[0505] The hole injection layer (HIL) is a mixture of HAT-CN and HT-1, with a mass ratio of HAT-CN to HT-1 of 3:97, a thickness of 10 nm, and a total evaporation rate of 0.1 nm / s.

[0506] The hole transport layer (HTL) is made of HT-1 material, has a thickness of 80 nm, and a total evaporation rate of 0.1 nm / s.

[0507] The light-emitting layer (EML) is vacuum-deposited by co-evaporation. The material of the light-emitting layer includes a host material and a guest material, wherein the guest material is RD and the host material is composed of N-4 and M-17 compounds in synthesis example 1. The specific ratio of the host material and the guest material is shown in Table 4 below. The thickness is 35 nm and the total evaporation rate is 0.1 nm / s.

[0508] The electron transport layer (ETL) is a binary mixture of ET and LiQ in a mass ratio of 1:1, with a thickness of 30 nm and a total evaporation rate of 0.1 nm / s.

[0509] The electron injection layer (EIL) is made of LiQ with a thickness of 1 nm and a total evaporation rate of 0.1 nm / s.

[0510] The cathode is made of aluminum with a thickness of 90 nm and a deposition rate of 1 nm / s.

[0511] Device Examples 2 to 52

[0512] Compared with Device Example 1, the difference is that the first compound N-4 in the light-emitting layer is replaced with the compounds obtained in Synthesis Examples 2 to 52, and M-17 is replaced with the remaining second compounds. The specific materials of the light-emitting layer are shown in Table 4.

[0513] Device Example 53

[0514] Compared with Device Example 1, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0515] Device Example 54

[0516] Compared with Device Example 2, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0517] Device Example 55

[0518] Compared with device embodiment 3, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0519] Device Example 56

[0520] Compared with device embodiment 4, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0521] Device Example 57

[0522] Compared with device embodiment 5, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0523] Device Example 58

[0524] Compared with device embodiment 6, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0525] Device Example 59

[0526] Compared with device embodiment 7, the difference lies in the ratio of the first compound and the second compound in the light-emitting layer. For the specific ratio of the host material and the guest material, please refer to Table 4.

[0527] Device Comparison Example 1

[0528] Similar to Device Example 1, the difference is that material N-4 in Device Example 1 is replaced with the following structure REF-1, and the specific ratio of the host material and the guest material is shown in Table 4 below.

[0529]

[0530] Device Comparison Example 2

[0531] Similar to Device Example 1, the difference is that material N-4 in Device Example 1 is replaced with the following structure REF-2, and the specific ratio of the host material and the guest material is shown in Table 4 below.

[0532]

[0533] Device Comparison Example 3

[0534] Similar to Device Example 1, the difference is that the second compound in Device Example 1 is removed, and the specific ratio of the host material and the guest material is shown in Table 4 below.

[0535] Device Comparison Examples 4 to 14

[0536] Similar to Comparative Example 3, the difference lies in changing the first compound in Comparative Example 1. The specific ratio of the host material and the guest material is shown in Table 4 below.

[0537] Device Comparison Example 15

[0538] Similar to Device Example 1, the difference is that the first compound in Device Example 1 is removed, and the specific ratio of the host material and the guest material is shown in Table 4 below.

[0539] Device Comparison Examples 16 to 19

[0540] Similar to Comparative Example 15, the difference lies in changing the second compound in Comparative Example 15. The specific ratio of the host material and the guest material is shown in Table 4 below.

[0541] Table 4

[0542]

[0543]

[0544]

[0545] Device Test Examples

[0546] The organic electroluminescent devices obtained in Device Examples 1-59 and Device Comparative Examples 1 to 19 in the device examples were tested.

[0547] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0548] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0549] Lifetime test: current density 50mA / cm 2 The recording time (in hours) when the device brightness drops to 95% of its original brightness.

[0550] The lifetime T95 of Comparative Example 1 was set to 100. The test results of lifetime T95 of Device Examples 1-59 and Comparative Examples 2-19 relative to Comparative Example 1 are shown in Table 5.

[0551] With the current efficiency of Comparative Example 1 set to 100%, the test results of the lifetime T95 of Comparative Examples 1-59 and Comparative Examples 2-19 relative to Comparative Example 1 are shown in Table 5.

[0552] The driving voltages of device examples 1-59 and device comparative examples 1-19 are shown in Table 5.

[0553] Table 5

[0554]

[0555]

[0556]

[0557] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic electroluminescent composition, characterized in that, The organic electroluminescent composition comprises a first compound and a second compound; The first compound has the structure shown in formula (1): In equation (1), X 4 X 5 X 6 Selected from N; X 1 X 2 X 3 Each independently selected from CR 1 CR 2 or CR 3 R 1 Selected from equation (1-1) or equation (1-2), R 2 Choose from equation (1-3) or equation (1-4); Where R 1 When R is selected from equation (1-1), 2 Not for equation (1-4), and R 3 Selected from substituted or unsubstituted C6-C12 aryl groups; when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C60 aryl groups; Ar 1 Selected from substituted or unsubstituted C6-C60 aryl groups; n1 is selected from integers from 0 to 6; Ar 2 Selected from substituted or unsubstituted C6-C60 aryl groups; n2 is selected from integers from 0 to 6; Ar 3 Selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C1-C60 heteroaryl groups; n3 is selected from integers from 0 to 6; Ar 4 Selected from substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C1-C60 heteroaryl groups; n4 is selected from integers from 0 to 6; The second compound has the structure shown in formula (2): in, R 4 -L 1 Ar 5 R 5 -L 2 Ar 6 R 6 -L 3 Ar 7 L 1 -L 3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene; L 1 -L 3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene; Ar 5 -Ar 7 Each is independently selected from hydrogen, deuterium, protium, tritium, halogen, cyano, substituted or unsubstituted C6-C60 aromatic amino group, substituted or unsubstituted C3-C60 heteroaryl amino group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, wherein Ar 5 -Ar 7 At least one of them is the structure shown in equation (II). R 7 -L 4 Ar 8 R 8 -L 5 Ar 9 , Among them, L 4 and L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene; Ar 8 and Ar 9 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; X is selected from O, S, Se, NAr, CR 9 R 10 Wherein, Ar is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 4 and R 5 Each is independently selected from hydrogen atoms, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents in the substituted C6-C12 aryl, substituted C6-C60 aryl, substituted C1-C60 heteroaryl, substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C3-C60 heteroaryl, substituted C1-C20 alkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 arylamine, and substituted C3-C60 heteroarylamine are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

2. The organic electroluminescent composition according to claim 1, characterized in that, The first compound has the structures shown in formulas (1-5) and (1-6): In the formula, R 3 Ar 1 Ar 2 Ar 3 Ar 4 The definitions of n1 and n2 are the same as those in claim 1.

3. The organic electroluminescent composition according to claim 1 or 2, characterized in that, Ar 1 and Ar 2 They are identical or different, and each is independently selected from substituted or unsubstituted C6-C50 aryl groups. The substituents in the substituted C6-C50 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C50 aromatic amino, and C3-C50 heteroaryl. Preferred, Ar 1 and Ar 2 They are identical or different, and each is independently selected from substituted or unsubstituted C6-C25 aryl groups. The substituents in the substituted C6-C25 aryl group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C25 aromatic amino, and C3-C25 heteroaromatic amino. Preferred, Ar 1 and Ar 2 They are identical or different, and each is independently selected from substituted or unsubstituted C6-C12 aryl groups. The substituents in the substituted C6-C12 aryl group are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C6-C12 aryl, and C1-C12 heteroaryl. Preferred, Ar 1 and Ar 2 The same or different, and each independently selected from substituted or unsubstituted naphthyl groups, The substituents in the substituted naphthyl group are selected from deuterium.

4. The organic electroluminescent composition according to any one of claims 1-3, characterized in that, The first compound has the following structure: Among them, R 3 Ar 3 Ar 4 The definitions of n1, n2, n3, and n4 are the same as those in claim 1; n5 to n8 are selected from integers from 0 to 7; Preferably, n5 to n8 are each independently selected from integers from 0 to 6; Preferably, n5 to n8 are each independently selected from integers from 0 to 5; Preferably, n5 to n8 are each independently selected from integers from 0 to 4; Preferably, n5 to n8 are each independently selected from integers from 0 to 3; Preferably, n5 to n8 are each independently selected from integers from 0 to 2.

5. The organic electroluminescent composition according to any one of claims 1-4, characterized in that, Ar 3 and Ar 4 They are either the same or different, and each is independently selected from substituted or unsubstituted C6-C50 aryl groups or substituted or unsubstituted C1-C50 heteroaryl groups. Wherein, the substituents in the substituted C6-C50 aryl and substituted C6-C50 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C50 heteroaryl. Preferred, Ar 3 and Ar 4 They may be the same or different, and each is independently selected from substituted or unsubstituted C6-C25 aryl or substituted or unsubstituted C6-C25 heteroaryl. Wherein, the substituents in the substituted C6-C25 aryl and substituted C6-C25 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, C3-C25 heteroaryl, C6-C25 aromatic amino, and C3-C25 heteroaromatic amino. Preferred, Ar 3 and Ar 4 They are either the same or different, and each is independently selected from the group consisting of the following groups:

6. The organic electroluminescent composition according to any one of claims 1-5, characterized in that, When R 1 When R is selected from equation (1-1), 2 Not for equation (1-4), and R 3 Selected from the group consisting of the following groups: Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C50 aryl groups, The substituents in the substituted C6-C50 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from substituted or unsubstituted C6-C25 aryl groups; The substituents in the substituted C6-C25 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C25 aryl, and C3-C25 heteroaryl. Preferably, when R 1 When R is selected from equation (1-2), 2 Not for equation (1-3), and R 3 Selected from the group consisting of the following groups:

7. The organic electroluminescent composition according to any one of claims 1-6, characterized in that, n1 to n4 are each independent integers selected from 0 to 5; Preferably, n1 to n4 are each independently selected from integers from 0 to 4; Preferably, n1 to n4 are each independently selected from integers from 0 to 3; Preferably, n1 to n4 are each independently selected from integers from 0 to 2.

8. The organic electroluminescent composition according to any one of claims 1-7, characterized in that, The first compound is selected from one of the following structures:

9. The organic electroluminescent composition according to any one of claims 1-8, characterized in that, In the second compound, L 1 -L 3 For connecting bonds, substituted or unsubstituted C6-C15 arylene, substituted or unsubstituted C3-C15 heteroarylene; The substituents in the substituted C6-C15 arylene and the substituted C3-C15 heteroarylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, L 1 -L 3 Each is independently selected from the linking bond, phenylene, naphthylene, triphenylene, and biphenylene; Preferably, L 1 Selected from the link key, L 2 Selected from phenylene, naphthylene, triphenylene, biphenylene, L 3 For connection key; Preferably, L 1 -L 3 Each is independently selected from a single bond; Preferred, Ar 5 -Ar 7 At least one of them is the structure shown in equation (II). If not all of them are the structure shown in equation (II), the remaining Ar 5 -Ar 7 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferred, Ar 5 -Ar 7 At least one of them is the structure shown in equation (II). If not all of them are the structure shown in equation (II), the remaining Ar 5 -Ar 7 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl; The substituents in the substituted dibenzofuranyl and substituted dibenzothiopheneyl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, L 4 and L 5 For connecting bonds, substituted or unsubstituted C6-C15 arylene groups; The substituents in the substituted C6-C15 arylene groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, L 4 and L 5 Each is independently selected from single bonds, phenylene, and naphthylene; Preferably, L 4 and L 5 Each is independently selected from a single bond; Preferably, Ar is selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar is selected from substituted or unsubstituted group A, and group A is selected from: phenyl, naphthyl, biphenyl, terphenyl, triphenylene. Dibenzofuranyl, dibenzothiophene; Wherein, the substituent in the substituted group A is one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferred, R 9 and R 10 Each is independently selected from substituted or unsubstituted C1-C5 alkyl groups and substituted or unsubstituted C6-C30 aryl groups; The substituents in the substituted C1-C5 alkyl and substituted C6-C30 aryl groups are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

10. The organic electroluminescent composition according to any one of claims 1-9, characterized in that, Ar 8 -Ar 9 Each group is independently selected from substituted or unsubstituted group B, where group B is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, etc. alkyl, dibenzofuranyl, benzonaphthiofuranyl, dibenzothiophenyl, dibenzoselenophenolyl, triphenylene, dimethylfluorenyl, spirodifluorenyl, fluoranyl, carbazoleyl, phenylcarbazoleyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, pyridyl, pyrimidinyl, triazineyl; Wherein, the substituents in the substituted group B are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferred, Ar 8 and Ar 9 Each independently selected Among them, R T1 -R T6 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, or R T1 -R T5 Any two adjacent elements can fuse to form a C6-C30 ring A; Y is selected from O, S, NAr, and CR. 9 R 10 Among them, Ar and R 9 R 10 The definition is as defined in claim 1; When there are multiple R T1 -R T6 At that time, R T1 -R T6 Each is independent of the others and may be the same or different; The substituents in the substituted C1-C30 alkyl, substituted C7-C30 aralkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C4-C30 heteroaryl, substituted C3-C30 cycloalkyl, substituted C3-C30 heterocycloalkyl, substituted C3-C30 cycloalkenyl, substituted C1-C30 alkoxy, and substituted C6-C30 aryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, and substituted or unsubstituted phenanthrene rings; The substituents in the substituted benzene ring, substituted naphthyl ring, and substituted phenanthrene ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

11. The organic electroluminescent composition according to any one of claims 1-10, characterized in that, The second compound has the structure shown below; 12. The organic electroluminescent composition according to any one of claims 1-11, characterized in that, The mass ratio of the first compound to the second compound is 1:9 to 9:1; Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 2:8-8:2; Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 3:7-7:3; Preferably, in the organic electroluminescent composition, the mass ratio of the first compound to the second compound is 4:6 to 6:

4.

13. An organic electroluminescent host material composition, characterized in that, The light-emitting host material composition comprises the composition for organic optoelectronic devices as described in any one of claims 1-12.

14. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises an organic electroluminescent composition as described in any one of claims 1-12 or an organic electroluminescent host material composition as described in claim 13; Preferably, the organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an organic electroluminescent composition as described in any one of claims 1-12 or an organic electroluminescent host material composition as described in claim 13; Preferably, the organic layer includes a light-emitting layer, which comprises an organic electroluminescent composition as described in any one of claims 1-12 or an organic electroluminescent host material composition as described in claim 14.

15. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes the organic electroluminescent device as described in claim 14, the organic electroluminescent composition as described in any one of claims 1-12, or the organic electroluminescent host material composition as described in claim 13.

Images