An organic electroluminescence host material composition, a light-emitting device and application

Abstract

This invention discloses an organic electroluminescent compound, a composition, a light-emitting device, and an application. The organic electroluminescent compound is compound M with the structure shown in formula (2), where X... 1 -X 14 Selected from N or CR 8 R 8 Selected from hydrogen or deuterium; L is selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar 8 -Ar 9 Each compound is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; the substituents are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl groups. When compound M and compound N of this invention are used together as the organic electroluminescent host material for organic light-emitting devices, the turn-on voltage of the organic light-emitting devices can be significantly reduced, the luminous efficiency can be significantly improved, and the lifetime can be significantly extended.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence, and more specifically to an organic electroluminescent host material composition, a light-emitting device, 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 OLED 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. Based on the functions achieved by each layer, the various materials used in the organic layer are categorized 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, etc. In an OLED, 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] Existing publicly disclosed organic light-emitting compounds include amine derivatives of indenetriphenylene and triazine-based electron transport materials. Examples include an amine derivative based on indenetriphenylene disclosed in US patent application US20200115369A1, and a triazine-based electron transport material, its preparation method, and applications disclosed in Chinese patent application CN113004295A. Existing publicly disclosed amine derivatives based on indenetriphenylene can serve as organic electroluminescent devices, acting as both charge transport layers and electron blocking layers.

[0004] However, existing organic light-emitting compounds used in functional materials suffer from low stability and unbalanced carrier mobility, resulting in problems such as high driving voltage, low luminous efficiency, and short lifespan for organic light-emitting diodes, which severely limit their applications. Summary of the Invention

[0005] Therefore, the technical problem to be solved by the present invention is to overcome the problems of low stability of organic electroluminescent materials and high driving voltage of light-emitting devices caused by unbalanced carrier mobility in the prior art, thereby providing an organic electroluminescent host material composition, light-emitting device and application that solves the above problems.

[0006] An organic electroluminescent compound, namely compound M with the structure shown in formula (2),

[0007] Equation (2):

[0008] In equation (2), X 1 -X 14 Each is independently selected from N or CR 8 R 8 Selected from hydrogen or deuterium;

[0009] L is selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0010] Ar 8 -Ar 9 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0011] The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C30 aryl, and substituted C3-C30 heteroarylene 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 heteroarylene.

[0012] When X 1 -X 14 All are CR 8 At that time, Ar 8 -Ar 9 The naphthyl group may be substituted or unsubstituted at the same time.

[0013] In equation (2), X 1 -X 14 One of them is selected from N, and the rest are CR. 8 ; or X 1 -X 6 One of them is selected from N, and the rest are CR. 8 X 7 -X 14 One of them is selected from N, and the rest are CR. 8 ; or, X 1 -X 14 All selected from CR 8 When there are multiple R 8 At that time, they exist independently and may be the same or different.

[0014] Ar 8 -Ar 9Each group is independently selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluoranyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl.

[0015] Ar 8 -Ar 9 Each group is independently selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, benzocarbazoyl, benzocarbazoyl, dibenzocarbazoyl.

[0016] The structure of compound M is shown in any one of formulas 2-1 to 2-5:

[0017]

[0018] Among them, X 1 -X 14 Ar 8 -Ar 9 The definition of L is the same as in claim 1 or 2. The structure of compound M is shown in any one of formulas 2-6 to 2-28:

[0019]

[0020]

[0021]

[0022] Among them, X 1 -X 14 Ar 8 -Ar 9 The definition of L is the same as that in claim 1 or 2. The structure of the compound M is shown as any one of M-1 to M-388 below.

[0023] The structures of M-1 to M-388 are as follows:

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032] The structure of compound M is shown as any one of M-389 to M-619 below.

[0033] The structures of M-389 to M-619 are as follows:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] An organic electroluminescent host material composition comprising compound N with the structure shown in formula (1) and compound M with the structure shown in formula (2) as described above;

[0040] Equation (1):

[0041] In equation (1), X is selected from O, S, Se, NAr, or CR. 6 R 7 Wherein, Ar is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 6 -R 7 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;

[0042] R 1 -L 1 Ar 1 R 2 -L 2 Ar 2 R 3 -L 3Ar 3 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 1 -Ar 3 At least one of them is Indicates a connection key, the R 4 -L 4 Ar 4 R 5 -L 5 Ar 5 L 4 -L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, Ar 4 -Ar 5 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the remaining Ar 1 -Ar 3 Each is independently selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C6-C60 aromatic amino group, substituted or unsubstituted C3-C60 heteroaryl group, substituted or unsubstituted C6-C60 aryl group, and substituted or unsubstituted C3-C60 heteroaryl group.

[0043] In equation (1), It is understood that in this invention, R1 can be substituted on ring B or ring C, R2 can be substituted on ring D, and R3 can be substituted on ring E.

[0044] Preferably, the Ar 4 -Ar 5 Each of the following groups, individually selected from substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene. alkyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, dibenzoselenophenolyl, triphenylene, dimethylfluorenyl, spirodifluorenyl, fluoranyl, carbazoleyl, phenylcarbazoleyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, pyridyl, pyrimidinyl, triazineyl.

[0045] The Ar 4 -Ar 5 Each independently selected

[0046] Among them, R T1 -R T6Each 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. 6 R 7 ;Among them, Ar and R 6 R 7 The definition is the same as above;

[0047] 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;

[0048] Preferably, ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, and substituted or unsubstituted phenanthrene rings.

[0049] The Ar is selected from substituted or unsubstituted C6-C30 aryl groups and C3-C30 heteroaryl groups; preferably, it is selected from substituted or unsubstituted groups such as phenyl, naphthyl, biphenyl, terphenyl, and triphenylene. alkyl, dibenzofuranyl, dibenzothiophenyl;

[0050] And / or, R 6 R 7 Each is independently selected from substituted or unsubstituted C1-C5 alkyl groups and substituted or unsubstituted C6-C30 aryl groups.

[0051] L 1 -L 3 Each is independently selected from the linker, C6-C30 aryl groups, preferably L 1 -L 3 Each is independently selected from the linking bond, phenylene, naphthylene, triphenylene, and biphenylene; further optionally, 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;

[0052] And / or, L 4 -L 5 Each aryl group is independently selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups; optionally, L 4 -L 5 Each is independently selected from single bonds, phenylene, and naphthylene; further optionally, L... 4 -L 5 Each is independently selected from a single bond;

[0053] And / or, the remaining Ar 1 -Ar 3 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl.

[0054] The structure of compound N is shown in any one of Formulas 1-1 to 1-17;

[0055]

[0056]

[0057] Where R 1 -R 7 L 1 -L 3 The definitions of Ar are the same as above.

[0058] The structure of compound N represented by formula (1) is shown as any one of N-1 to N-935. The structures of N-1 to N-935 are as follows:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] The mass ratio of compound N to compound M is 9:1-1:9; preferably 2:8-8:2; more preferably 3:7-7:3; and even more preferably 4:6-6:4.

[0095] The application of the above-mentioned organic electroluminescent host material composition in optical devices is preferably in organic electroluminescent devices.

[0096] Preferably, the optical device includes any one of organic electroluminescent devices, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic integrated circuits, organic solar cells, organic field quenching devices, luminescent electrochemical cells, organic laser diodes, or organic photoreceptors.

[0097] An organic electroluminescent material comprises one of the above-described organic electroluminescent compounds or an organic electroluminescent host material composition. Preferably, the organic electroluminescent material further comprises a dopant material. Preferably, the dopant material comprises a phosphorescent dopant, and the phosphorescent dopant comprises a transition metal complex.

[0098] An organic electroluminescent device includes an anode and a cathode, and an organic layer disposed between the anode and the cathode; the organic layer includes one of the organic electroluminescent compounds or one of the organic electroluminescent host material compositions described above.

[0099] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer (electron buffer layer), an electron transport layer, and an electron injection layer, which are stacked sequentially from the anode side to the cathode side.

[0100] An organic electroluminescent device includes the aforementioned organic electroluminescent device.

[0101] Unless otherwise specified, the substituents in all other structures of this invention 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.

[0102] The term "organic electroluminescent material" disclosed in this invention refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing an organic electroluminescent host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0103] The organic electroluminescent material disclosed in this invention may comprise one or more organic electroluminescent materials, wherein "multiple organic electroluminescent materials" means a material comprising a combination of at least two organic electroluminescent materials, and said material may be contained in any layer constituting the organic electroluminescent device. It may mean both a material contained before the organic electroluminescent device (e.g., before vapor deposition) and a material contained after the organic electroluminescent device (e.g., after vapor deposition). For example, the material may be a combination of at least two compositions, said composition may include at least one of the following: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two compositions in the multiple organic electroluminescent materials may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0104] The term "organic electroluminescent host material composition" disclosed in this invention refers to an organic electroluminescent material comprising a combination of at least two host materials. It can refer to both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. The compositions disclosed in this invention can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds of the various host materials included in the compositions disclosed in this invention can be included in one light-emitting layer, or they can be included separately in different light-emitting layers. For example, when a layer contains two or more host materials, the layer can be formed by co-evaporation, or it can be formed simultaneously by individual co-evaporation.

[0105] In this invention, "halogen" may include fluorine, chlorine, bromine or iodine.

[0106] In this invention, "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0107] In this invention, "C3-C30 cycloalkyl" refers to monocyclic or polycyclic hydrocarbons derived from a main chain of 1 to 30 carbon atoms. The cycloalkane may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, adamantyl, etc.

[0108] The aryl and arylene groups in this invention include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings can be interrupted by short non-aromatic units, and may contain spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, phenylphenanthrene, binatyl, phenylnaphthyl, naphthylphenyl, anthracene, indene, triphenylene, tetraphenyl, pyrene, perylene, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzo[a]fluorenyl, spirodifluorenyl, etc. Naphthyl, naphthyl, fluoranthyl, etc.

[0109] The heteroaryl and hypoaryl groups in this invention 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. Including but not limited to furanyl, phenylthio, pyrroloyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, benzothiazolyl, benziisothiazolyl, benziisooxazolyl, benzooxazolyl, isoindolyl, indolyl, inzolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridinyl, and their derivatives.

[0110] In this invention, "substituted" means that a hydrogen atom in a 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. It also includes the substitution of a hydrogen atom by a group formed by the linkage of two or more substituents. When two or more substituents are present, the two or more substituents can be the same or different. For example, the group formed by the linkage of two or more substituents can be pyridine-triazine. That is, pyridine-triazine can be interpreted as a heteroaryl substituent, or a substituent in which two heteroaryl substituents are linked.

[0111] Unless otherwise stated, hydrogen atoms in this invention include protium, deuterium, and tritium.

[0112] The groups in this invention define a range of carbon atoms, and the number of carbon atoms should be any integer within the defined range, such as C6-C30 aryl. The number of carbon atoms representing the aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30.

[0113] When the groups in this invention have substituents, each substituent is independently selected from deuterium, halogen, cyano, nitro, unsubstituted or R'-substituted C1-C4 straight-chain or straight-chain alkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and unsubstituted or R'-substituted C6-C20 aromatic amino; R' is selected from deuterium, halogen, cyano, and nitro.

[0114] By using a specific combination of compounds from the present invention as the main material composition, an organic electroluminescent device with improved luminous efficiency and lifetime characteristics compared to conventional organic electroluminescent devices can be provided, and a display system or lighting system using said organic electroluminescent device can be manufactured.

[0115] The technical solution of this invention has the following advantages:

[0116] 1. The present invention provides an organic electroluminescent compound, which is compound M with the structure shown in formula (2). Compared with CBP, REF-1 and other compounds disclosed in the prior art, compound M has significantly better performance and can have a lower start-up voltage, i.e., a lower driving voltage, after being fabricated into a device. Moreover, compound M can cooperate with compound N, which contains a polycyclic heteroaromatic group of triphenylene in the present invention, as an organic electroluminescent host material for organic light-emitting devices. Under the synergistic effect, the start-up voltage of organic light-emitting devices can be significantly reduced, the luminous efficiency can be significantly improved, and the lifetime can be significantly extended. Therefore, compound M with the structure shown in formula (2) in the present invention can cooperate with compound N to achieve the advantage of significantly improving the performance of the light-emitting host material, and can be used to produce organic electroluminescent devices with high luminous efficiency and long lifetime characteristics.

[0117] 2. The present invention provides an organic electroluminescent host material composition, comprising compound M with the structure shown in formula (2) and compound N with the structure shown in formula (1); the light-emitting host material composed of compound M and compound N is applied to light-emitting materials to prepare light-emitting devices, and the compounds M and N can synergistically enhance each other, and the synergistic effect can significantly reduce the start-up voltage of the light-emitting device, significantly improve the luminous efficiency, and significantly extend the lifespan; thus achieving the effect of significantly improving the luminous efficiency of the light-emitting device and significantly extending the lifespan of the light-emitting device. In the present invention, when compound M with the structure shown in formula (2) and compound N with the structure shown in formula (1) are applied to light-emitting devices, the light-emitting devices can have a lower driving voltage (below 3.44V), a higher current efficiency (above 24Cd / A) and a higher lifespan (above 260h). Detailed Implementation

[0118] The following embodiments are provided to better understand the present invention and are not limited to the preferred embodiments described. They do not constitute a limitation on the content and scope of protection of the present invention. Any product that is the same as or similar to the present invention, derived by any person under the guidance of the present invention or by combining the features of the present invention with other prior art, falls within the protection scope of the present invention.

[0119] 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.

[0120] Example 1

[0121] An organic electroluminescent compound, M-17, is synthesized as follows:

[0122]

[0123] A 50 mL double-necked round-bottom flask was placed with a stir bar and a reflux tube attached. After drying, nitrogen gas was introduced. Compounds M17-A (19.8 mmol, CAS: 1884145-03-2), M17-B (20.75 mmol, CAS: 1883265-32-4), tetraphenylphosphine palladium (0.396 mmol), potassium carbonate (39.6 mmol), 35 mL of toluene, 15 mL of ethanol, and 15 mL of distilled water were added. The mixture was stirred at 90 °C for 8 hours. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The solid was purified by column chromatography to give compound M-17 (8.5 g, yield: 75%).

[0124] Elemental analysis: C 41 H 25 N3O; Theoretical values: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured values: C, 85.52; H, 4.38; N, 7.32; HRMS(ESI) m / z(M+): Theoretical value: 575.20; Measured value: 576.34.

[0125] Example 2

[0126] An organic electroluminescent compound, M-296, is synthesized as follows:

[0127] (I) Synthesis of intermediate M296-A, the synthetic route is as follows:

[0128]

[0129] Intermediate M296-1 (2-bromoquinoline, CAS: 2005-43-8, 20 g) and 200 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask equipped with a thermometer and a magnetic stirrer. Under nitrogen protection, the temperature was lowered to -78 °C, and n-butyllithium (1.6 M, 45.2 mL) was added dropwise under controlled temperature. After the addition was complete, the mixture was stirred for 1 h. Then, triisopropyl borate (19.52 g) was added dropwise under controlled temperature at -78 °C. After the addition was complete, the mixture was transferred to room temperature and reacted for 12 h. Hydrochloric acid solution (6.5 mL of 36% hydrochloric acid + 24 mL of water) was added dropwise. The reaction mixture was then extracted with 50 mL of ethyl acetate and 25 mL of water. The organic phase was evaporated to dryness, and 50 mL of n-hexane was added. The mixture was refluxed and stirred for 1 h. After filtration at room temperature and drying, intermediate M296-2, 15 g, was obtained.

[0130] Intermediate M296-2 (15g), intermediate 7-bromo-1-chloronaphthalene (21.9g), potassium carbonate (16.6g), and tetra-triphenylphosphine palladium (2.0g) were added to a 250mL three-necked flask equipped with a thermometer and a magnetic stirrer. Toluene (80mL), ethanol (35mL), and water (35mL) were added. Under nitrogen protection, the mixture was heated to 85℃ and reacted for 6h. The reaction solution was extracted with 50mL of ethyl acetate and 25mL of water. The organic phase was stirred and passed through a column to obtain intermediate M296-3, 15g.

[0131] Intermediate M296-3 (15g), pinacol diborate (15.8g), potassium acetate (10g), and Pd(dppf)Cl2 (0.64g) were added to a 250mL three-necked flask equipped with a thermometer and a magnetic stirrer. Under nitrogen protection, 1,4-dioxane (150mL) was added, and the mixture was heated to 110℃ and reacted for 4h. The reaction solution was extracted with 100mL toluene and 100mL of water. The organic phase was mixed and passed through a column to obtain intermediate M296-A, 16g.

[0132] (II) Synthesis of compound M-296, the synthetic route is as follows:

[0133]

[0134] Intermediate M296-A (16 g), intermediate M296-B (2-chloro-4,6-diphenyl-1,3,5-triazine, CAS: 3842-55-5, 11.2 g), potassium carbonate (11.6 g), and tetraphenylphosphine palladium (1.3 g) were added to a 250 mL three-necked flask equipped with a thermometer and a magnetic stirrer. Toluene (110 mL), ethanol (50 mL), and water (50 mL) were added. Under nitrogen protection, the mixture was heated to 85 °C and reacted for 6 h. The reaction solution was filtered with water and ethanol at room temperature and dried to obtain product M296, 16 g (yield 78%).

[0135] Elemental analysis: C 34 H22 Theoretical N4 values: C, 83.93; H, 4.56; N, 11.51; Measured values: C, 83.95; H, 4.56; N, 11.49; HRMS(ESI) m / z(M+): Theoretical value: 486.18; Measured value: 487.12.

[0136] Example 3

[0137] An organic electroluminescent compound, M-381, is synthesized as follows:

[0138] (I) Synthesis of intermediate M381-B, the synthetic route is as follows:

[0139]

[0140] Intermediate M381-1 (CAS: 5332-25-2, 20 g) and 200 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask equipped with a thermometer and a magnetic stirrer. Under nitrogen protection, the temperature was lowered to -78 °C, and n-butyllithium (1.6 M, 45.2 mL) was added dropwise under controlled temperature. After the addition was complete, the mixture was stirred for 1 h. Then, triisopropyl borate (19.52 g) was added dropwise under controlled temperature at -78 °C. After the addition was complete, the mixture was transferred to room temperature and reacted for 12 h. Hydrochloric acid solution (36% concentration hydrochloric acid, 6.5 mL + 24 mL water) was added dropwise. The reaction mixture was extracted with 50 mL of ethyl acetate and 25 mL of water. The organic phase was evaporated to dryness, and 50 mL of n-hexane was added. The mixture was refluxed and stirred for 1 h. After filtration at room temperature and drying, intermediate M381-2, 15 g, was obtained.

[0141] Intermediate M381-2 (15g), raw material M367-a (CAS: 99455-15-9, 21g), potassium carbonate (16.6g), and tetraphenylphosphine palladium (2.0g) were added to a 250mL three-necked flask equipped with a thermometer and a magnetic stirrer. Toluene (80mL), ethanol (35mL), and water (35mL) were added. Under nitrogen protection, the mixture was heated to 85℃ and reacted for 6h. 50mL of ethyl acetate was added to the reaction solution, followed by extraction with 25mL of water. The organic phase was mixed and passed through a column to obtain intermediate M381-3, 13g.

[0142] Intermediate M381-3 (13g) and 200mL of anhydrous tetrahydrofuran were added to a 250mL three-necked flask equipped with a thermometer and a magnetic stirrer. Under nitrogen protection, the temperature was lowered to -78℃, and n-butyllithium (1.6M, 40mL) was added dropwise under controlled temperature. After the addition was complete, the mixture was stirred for 1h, and then triisopropyl borate (17g) was added dropwise under controlled temperature at -78℃. After the addition was complete, the mixture was transferred to room temperature and reacted for 12h. Hydrochloric acid solution (36% concentration hydrochloric acid, 6.5mL + 24mL water) was added dropwise. The reaction mixture was extracted with 50mL ethyl acetate and 25mL water. The organic phase was evaporated to dryness, and 50mL of n-hexane was added. The mixture was refluxed and stirred for 1h. After filtration at room temperature and drying, intermediate M381-4, 12g, was obtained.

[0143] Intermediate M381-4 (12g), raw material M381-b (CAS: 112719-97-8, 11g), potassium carbonate (11g), and tetraphenylphosphine palladium (1.2g) were added to a 250mL three-necked flask equipped with a thermometer and a magnetic stirrer. Toluene (80mL), ethanol (35mL), and water (35mL) were added. Under nitrogen protection, the mixture was heated to 85℃ and reacted for 6h. 50mL of ethyl acetate was added to the reaction solution, followed by extraction with 25mL of water. The organic phase was stirred and passed through a column to obtain intermediate M381-B, 16g.

[0144] (II) Synthesis of compound M-381, the synthetic route is as follows:

[0145]

[0146] Intermediate M381-B (16g), raw material M381-A (6.85g, CAS: 395087-89-5), potassium carbonate (9g), and tetra-triphenylphosphine palladium (1.0g) were added to a 250mL three-necked flask equipped with a thermometer and magnetic stirrer. Toluene (80mL), ethanol (35mL), and water (35mL) were added. Under nitrogen protection, the mixture was heated to 85℃ and reacted for 6h. The reaction solution was extracted with 50mL of ethyl acetate and 25mL of water. The organic phase was stirred and passed through a column to obtain the final product M-381, 15g (yield 74%).

[0147] Elemental analysis: C 43 H 25 N 50 Theoretical values: C, 82.28; H, 4.01; N, 11.16; O, 2.55; Measured values: C, 82.30; H, 4.01; N, 11.14; HRMS(ESI) m / z(M+): Theoretical value: 627.21; Measured value: 628.13.

[0148] Example 4

[0149] An organic electroluminescent compound, namely compounds M-76, M-108, M-145, M-253, M-308, M-365, or M-371, is synthesized as follows:

[0150] Raw materials Mn-B (16g), Mn-A (6.85g), potassium carbonate (9g), and tetraphenylphosphine palladium (1.0g) were added to toluene (80mL), ethanol (35mL), and water (35mL) under nitrogen protection. The mixture was heated to 85℃ and reacted for 6h. 50mL of ethyl acetate was added to the reaction solution, followed by extraction with 25mL of water. The organic phase was mixed and passed through a column to obtain the final product.

[0151] The structures and yields of the starting materials Mn-B and Mn-A, as well as the products, are shown in Table 1. The elemental analysis results of the prepared compounds are shown in Table 2.

[0152] Table 1

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] Table 2

[0159]

[0160]

[0161] Example 5

[0162] An organic electroluminescent host material composition includes a compound N containing a polycyclic heteroaromatic group of triphenylene and a compound M, wherein compound M is any one of M-1 to M-619, preferably selected from an organic electroluminescent compound prepared in Examples 1-4; wherein compound N in the composition is any one of N-1 to N-935, preferably N-4, N-5, N-14, N-20, N-37, N-46, N-65, N-68, N-78, N-113, N-275, N-281, etc. Any one of the following compounds: N-358, N-369, N-389, N-423, N-424, N-434, N-439, N-447, N-470, N-486, N-505, N-517, N-520, N-529, N-533, N-629, N-641, N-669, N-685, N-728, N-860, N-874, N-899, N-901, N-906, N-912, and N-918; the synthesis process of each of the above compounds N is as follows:

[0163] 1. Synthesis route of N-4

[0164]

[0165] 1.1 Synthesis of intermediate N-4B'

[0166] Under nitrogen purging, 20 g (1.0 eq) 4a (CAS: 444796-09-2), 9.87 g (1.0 eq) 4b (CAS: 4688-76-0), 1.7 g (2% eq) Pd(PPh3)4, 8.37 g (2.0 eq) NaHCO3, 180 mL tetrahydrofuran (4a:tetrahydrofuran = 1 g:9 mL), and 60 mL ultrapure water (4a:ulpure water = 1 g:3 mL) were added to a 500 mL three-necked flask equipped with a magnetic stirrer. The reaction was carried out at 65 °C for 2 h until complete. Column purification yielded 10 g of product N-4B'.

[0167] 1.2 Synthesis of intermediate N-4B

[0168] 10 g (1.0 eq) of intermediate N-4B', 20.5 g (6.0 eq) of anhydrous FeCl3, and 100 mL of anhydrous dichloromethane (N-4B': dichloromethane = 1 g: 10 mL) were added to a 250 mL three-necked flask equipped with a magnetic stirrer. The reaction was carried out at -10 °C for 1 h until complete. 7 g of product N-4B was obtained by column purification.

[0169] 1.3 Synthesis of compound N-4

[0170] Under nitrogen purging, 7 g (1.0 eq) N-4B, 4.0 g (1.1 eq) N-4A (CAS: 35887-50-4), 0.27 g (2% eq) Pd2(dba)3, 2.85 g (2.0 eq) t-BuONa, and 70 mL anhydrous toluene (N-4B: anhydrous toluene = 1 g: 10 mL) were added to a 250 mL three-necked flask equipped with a magnetic stirrer. The reaction was carried out at 100 °C for 2 h until complete. The product N-4 was purified by column chromatography to yield 5 g.

[0171] Elemental analysis: C 48 H 32 Theoretical N2 values: C, 90.54; H, 5.07; N, 4.40; Measured values: C, 90.53; H, 5.08; N, 4.41; HRMS(ESI) m / z(M+): Theoretical value: 636.26; Measured value: 637.55.

[0172] 2. Synthetic route of N-5

[0173]

[0174] Under nitrogen purging, 7 g (1.0 eq) of intermediate N-4B, 4.82 g (1.1 eq) of N-5A (CAS: 1401351-42-5), 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, and 70 mL of anhydrous toluene (intermediate N-4B: anhydrous toluene = 1 g: 10 mL) were added to a 250 mL three-necked flask equipped with a magnetic stirrer. The reaction was carried out at 100 °C for 2 h until complete. 5 g of product was obtained after column purification.

[0175] Elemental analysis: C 52 H 34 Theoretical N2 values: C, 90.93; H, 4.99; N, 4.08; Measured values: C, 90.92; H, 4.98; N, 4.10; HRMS(ESI) m / z(M+): Theoretical value: 686.27; Measured value: 687.22.

[0176] 3. Synthetic route of N-14

[0177]

[0178] Under nitrogen purging, 7 g (1.0 eq) of intermediate N-4B, 4.4 g (1.1 eq) of N-14A (CAS: 1357009-66-5), 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, and 70 mL of anhydrous toluene (intermediate 2: anhydrous toluene = 1 g: 10 mL) were added to a 250 mL three-necked flask equipped with a magnetic stirrer. The reaction was carried out at 100 °C for 2 h until complete. 5 g of product was obtained after column purification.

[0179] Elemental analysis: C 50 H 32 Theoretical N2 values: C, 90.88; H, 4.88; N, 4.24; Measured values: C, 90.86; H, 4.88; N, 4.26; HRMS(ESI) m / z(M+): Theoretical value: 660.25; Measured value: 661.37.

[0180] 4. Synthetic routes for N-20, N-37, N-46, N-65, N-68, N-78, N-113, N-275, N-281, N-358, N-369, and N-389.

[0181] The synthesis conditions are the same as those for N-14, the difference lies in the different structures and yields of the starting materials N-nA and N-nB, as well as the product, as shown in Table 3 below; the elemental analysis results of the prepared compounds are shown in Table 4.

[0182] Table 3

[0183]

[0184]

[0185]

[0186]

[0187] Table 4

[0188]

[0189] 5. Synthetic route of N-423

[0190]

[0191] Add 20g of 423a (i.e., 4b), 29.9g of 423b (CAS: 67019-91-4), 2.3g of Pd[P(C6H5)3]4, 27.9g of K2CO3, 280mL of toluene, 120mL of H2O, and 120mL of ethanol to a 1000mL three-necked flask equipped with a mechanical stirrer, reflux condenser, and thermometer. Purge three times with nitrogen and react at 85℃ under nitrogen protection. The reaction should begin 150min from the start of heating. After the reaction is complete, add 120mL of water to quench the reaction. After separation, evaporate to dryness to obtain an oily substance (wet weight 44g). Vacuum extraction yields 25g of N-423B'.

[0192] 25 g of crude N-423B' (oily substance) and 750 mL of dichloromethane (N-423B': DCM = 1 g: 30 mL) were added to a 2 L three-necked flask equipped with a stirrer and thermometer. The temperature was maintained at -5 °C. Ferric chloride was added in two batches, with an interval of 15 min between each batch (3 equivalents of ferric chloride), while maintaining the temperature at -5 °C. After the reaction was complete, 750 mL of ethanol (N-423B': ethanol = 1 g: 30 mL) was slowly added, while maintaining the temperature below 0 °C. After the addition was complete, the mixture was stirred continuously for 0.5 h, resulting in the precipitation of a yellowish-white solid. The solid was filtered, and the filter cake was washed with 250 mL of ethanol (N-423B': ethanol = 1 g: 1 mL) to obtain a yellow solid. The solid was then dissolved in 1.75 L of chlorobenzene, and after crystallization, the temperature was allowed to dropwise cool to 60 °C. 250 mL of n-hexane solution was added, and the mixture was filtered to obtain 20 g of crude N-423B.

[0193]

[0194] 25 g of N-423A (CAS: 32228-99-2), 40.48 g of N-423B (CAS: 2035812-74-7), 1.86 g of Pd2(dba)3, 1.67 g of sphos, 24.4 g of gt-BuONa, and 500 mL of toluene were added to a 1000 mL three-necked flask equipped with a mechanical stirrer, reflux condenser, and thermometer. The mixture was purged with nitrogen three times and reacted at 110 °C under nitrogen protection for 120 min from the start of heating. After the reaction was complete, 120 mL of water was added to quench the reaction. After separation, the mixture was evaporated to dryness, passed through a column chromatography line, and dried to obtain 35 g of crude N-423.

[0195] Elemental analysis: C 42 H 27 NO; Theoretical value: C, 89.81; H, 4.85; N, 2.49; O, 2.85; Measured value: C, 89.78; H, 4.86; N, 2.51; HRMS(ESI) m / z(M+): Theoretical value: 561.21; Measured value: 562.29.

[0196] 6. Synthetic route of N-425

[0197]

[0198] 14 g of N-425A (CAS: 1401351-43-6), 18.8 g of N-423B (CAS: 2035812-74-7), 0.86 g of Pd2(dba)3, 1.9 g of sphos, 9.1 g of gt-BuONa, and 150 mL of toluene were added to a 500 mL three-necked flask equipped with a mechanical stirrer, reflux condenser, and thermometer. The mixture was purged with nitrogen three times and reacted at 110 °C under nitrogen protection for 120 min from the start of heating. After the reaction was complete, 150 mL of water was added to quench the reaction. After separation, the mixture was evaporated to dryness, slurried with ethanol, and then dissolved and crystallized with toluene to obtain 16 g of crude N-425.

[0199] Elemental analysis: C 46 H 29 Theoretical NO values: C, 90.32; H, 4.78; N, 2.29; O, 2.62; Measured values: C, 90.30; H, 4.77; N, 2.32; HRMS(ESI) m / z(M+): Theoretical value: 611.22; Measured value: 612.45.

[0200] 7. Synthetic routes for N-424, N-434, N-439, N-447, N-470, N-486, N-505, N-517, N-520, N-529, N-533, N-629, N-641, N-669, N-685, N-728, N-860, and N-874.

[0201] The synthesis conditions were the same as those for N-425, except that the starting materials N-nA and N-nB, as well as the structure and yield of the product, were different, as shown in Table 5 below; the elemental analysis results of the prepared compounds are shown in Table 6.

[0202] Table 5

[0203]

[0204]

[0205]

[0206]

[0207] Table 6

[0208]

[0209]

[0210] 8. Synthetic route of N-912

[0211]

[0212] A mixture of 35.2 g (100 mmol) 2,7-dibromo-9,9-dimethyl-9H-fluorene (CAS: 28320-31-2), 21.8 g (110 mmol) biphenyl-2-ylboronic acid, 2.31 g (2 mmol) Pd(PPh3)4, 75 mL 2M Na2CO3, 150 mL EtOH, and 300 mL toluene was degassed and placed under nitrogen atmosphere, and then heated at 100 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by silica gel column chromatography to give the product 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene (26.8 g, 63.0 mmol, 63%) as a white solid.

[0213] In a degassed and nitrogen-filled 3000 mL three-necked flask, 26.8 g (60 mmol) of 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene was dissolved in 1500 mL of anhydrous dichloromethane, followed by the addition of 97.5 g (600 mmol) of ferric chloride (III), and the mixture was stirred for one hour. 500 mL of methanol was added to the mixture, and the organic layer was separated and the solvent removed under vacuum. The residue was purified by column chromatography (hexane-dichloromethane) packed with silica gel to give a white solid N-912A (10.7 g, 25.3 mmol, 40%).

[0214]

[0215] A mixture of 20 g (41.3 mmol) N-(biphenyl-4-yl)-9,9'-spirodifluorene-2-amine (CAS: 1258514-95-2), 14 g (49.5 mmol) 1-bromo-4-iodobenzene, 2.4 g (12.4 mmol) copper iodide, 17.1 g (123.9 mmol) potassium carbonate, and 300 mL DMF was refluxed overnight under nitrogen. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by column chromatography (hexane-dichloromethane) packed with silica gel to give 26.3 g (43% yield) of the product as a white solid.

[0216] A mixture of 10 g (15.6 mmol) N-(biphenyl-4-yl)-N-(4-bromo-phenyl)-9,9'-spirodi[fluorene]-2-amine, 4.75 g (18.72 mmol) bis(pinacol)diboron, 0.18 g (0.156 mmol) tetrakis(triphenylphosphine)palladium, 2 g (20.28 mmol) potassium acetate, and 300 mL of 1,4-dioxane was degassed and placed under nitrogen atmosphere, and then heated at 90 °C for 16 h. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate to remove the solvent, and the product was purified by column chromatography using a mixture of hexane and ethyl acetate as eluent to give 8.77 g of the pale yellow product N-912B (N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborone-pentane-2-yl)phenyl)-9,9'-spirodifluorene-2-amine, yield 82%).

[0217]

[0218] A mixture of 15 g (35.43 mmol) 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene (N-912A), 29.1 g (42.51 mmol) N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-9,9'-spirodifluorene-2-amine (N-912B), 0.41 g (0.35 mmol) tetrakis(triphenylphosphine)palladium, 23 ml 2M Na₂CO₃, 100 ml EtOH, and 200 ml toluene was degassed and placed under nitrogen atmosphere, and then heated at 100 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried with anhydrous magnesium sulfate to remove the solvent, and the residue was purified by column chromatography (hexane-dichloromethane) packed with silica gel to give 17.5 g of the product as a yellow solid (N-912, yield 55%).

[0219] Elemental analysis: C 70 H 47 Theoretical N: C, 93.20; H, 5.25; N, 1.55; Measured: C, 93.16; H, 5.27; N, 1.57; HRMS(ESI) m / z(M+): Theoretical: 901.37; Measured: 902.21.

[0220] 9. Synthetic route of N-895

[0221]

[0222] A mixture of 5 g (11.8 mmol) 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene (N-912A), 6.8 g (14.1 mmol) N-(biphenyl-4-yl)-9,9'-spirodifluorene-2-amine (CAS: 1258514-95-2), 0.03 g (0.11 mmol) palladium(II) acetate, 0.04 g (0.11 mmol) 2-(dicyclohexylphosphino)biphenyl, 1.7 g (17.7 mmol) sodium tert-butoxide, and 100 mL of toluene was refluxed overnight under nitrogen. After the reaction was complete, the mixture was then cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried with anhydrous magnesium sulfate to remove the solvent, and the residue was purified by chromatography on a silica-packed column (hexane-dichloromethane) to give 5.8 g of the product as a yellow solid (N-895, yield 60%).

[0223] Elemental analysis: C 64 H 43 Theoretical N: C, 93.06; H, 5.25; N, 1.70; Measured: C, 93.02; H, 5.25; N, 1.73; HRMS(ESI) m / z(M+): Theoretical: 825.34; Measured: 826.19.

[0224] Synthetic routes for 10, N-899, N-901, N-906, and N-918

[0225] The synthesis conditions were the same as those for N-895, except that the starting materials N-nA and N-nB, as well as the structure and yield of the product, were different, as shown in Table 7 below; the elemental analysis results of the prepared compounds are shown in Table 8.

[0226] Table 7

[0227]

[0228]

[0229] Table 8

[0230]

[0231] Example 6

[0232] An organic electroluminescent device has the following structure from bottom to top: a substrate with an anode layer, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a cathode. The specific fabrication process is as follows:

[0233] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent are: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0234] (2) Vaporized hole injection layer:

[0235] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of NDP-9 and HT is vacuum-deposited onto the above-mentioned anolyte film, wherein the mass ratio of NDP-9 to HT is 3:97, serving as a hole injection layer, with a deposition thickness of 10 nm; wherein the structures of NDP-9 and HT are as follows:

[0236]

[0237] (3) A hole transport layer (material HT) is deposited on the hole injection layer, and the thickness of the deposited film is 80nm.

[0238] (4) A light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: the light-emitting host material and the dopant material (piq)2Ir(acac) are vacuum deposited by co-evaporation. The composition of the host material and the dopant material is shown in Table 9.

[0239] Table 9

[0240]

[0241]

[0242] The total thickness of the vapor-deposited film is 38 nm; the structure of (piq)₂Ir(acac) is as follows:

[0243]

[0244] (5) An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: the electron transport layer material is vacuum deposited by co-evaporation. The material is ET-1 and LiQ with a mass ratio of 1:1. The total film thickness is 30 nm. The structures of ET-1 and LiQ are as follows:

[0245]

[0246] (6) Vacuum evaporation of an electron injection layer on the electron transport layer, the material of the electron injection layer is LiQ, and the total thickness of the evaporation film is 1nm;

[0247] (7) Al was deposited on the electron injection layer, and the total film thickness was 80 nm.

[0248] Comparative Example 1

[0249] The difference between this comparative example and Example 6 is that the composition of the main material used in step (5) during the device fabrication process is different, as shown in Table 10; other steps and parameter conditions are the same as in Example 6.

[0250] Table 10

[0251] Device N1 <![CDATA[N-4:(piq)2Ir(acac) mass ratio = 95:5]]> Device N6 <![CDATA[N-685:(piq)2Ir(acac) mass ratio=95:5]]> Device C <![CDATA[CBP:(piq)₂Ir(acac) mass ratio = 95:5]]> Device RC <![CDATA[REF-1: CBP:(piq)2Ir(acac), mass ratio = 47.5:47.5:5]]> Device N1C <![CDATA[N-4:CBP:(piq)₂Ir(acac) mass ratio=47.5:47.5:5]]>

[0252] The structures of CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl, CAS: 58328-31-7) and REF-1 (CAS: 1070884-53-5) in the table above are as follows:

[0253]

[0254] Experimental Example

[0255] The devices prepared in Example 6 and Comparative Example 1 were used for performance testing under the following specific conditions:

[0256] The device's current, voltage, brightness, emission spectrum, and other characteristics were simultaneously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system.

[0257] Photoelectric property test conditions: current density 10 mA / cm² 2 ;

[0258] Lifetime test: current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0259] The performance test results of the above devices are shown in Tables 11 and 12.

[0260] Table 11

[0261] Device N1 4.00 16.31 110.8 Device M1 3.72 25.11 140.2 Device NM1-1 3.29 27.59 278.7 Device NM1-1' 3.24 28.79 294.7 Device N6 4.04 15.37 96.8 Device M6 3.78 24.77 136.7 Device NM6-6 3.25 27.66 284.5 Device NM6-6' 3.20 29.44 299.5 Device C 4.80 5.00 5.0 Device M1 3.72 25.11 140.2 Device M1C 3.87 23.43 151.0

[0262] Table 12

[0263]

[0264]

[0265] By comparing the data corresponding to the examples and comparative examples in Table 12, it can be seen that the new compound M developed in this invention has significantly better performance than CBP, REF-1 and other compounds disclosed in the prior art. After being fabricated into a device, it can have a lower turn-on voltage, i.e., a lower driving voltage as shown in Tables 11 and 12.

[0266] As shown by the data for device NM in Table 12 above, when the organic electroluminescent material is used as the organic functional layer material, the synergistic effect of compound N and compound M significantly improves the device performance compared to other existing similar structures, such as device RC (REF-1 and CBP synergistic), device N1C (N-4 and CBP synergistic), and device M1C (M1 and CBP synergistic). Furthermore, the above effect can also be seen by comparing the data in Table 11 above. Choosing compound N and compound M as the main materials in the luminescent material results in a more significant synergistic effect. Compared to using compound N or compound M alone, or synergizing them with other compounds as the main organic electroluminescent material, the combination of compound N and compound M has a significantly lower turn-on voltage, significantly improved luminous efficiency, and significantly increased device lifespan. The finally prepared device has a low driving voltage (below 3.44V), high current efficiency (above 24Cd / A), and high lifespan (above 260h).

[0267] As can be seen from the above, the synergistic effect of compound M and compound N developed in this invention can significantly improve carrier injection efficiency, reduce interlayer energy level differences, and balance electron and hole transport rates, effectively improving the efficiency and extending the lifetime of organic light-emitting diodes (OLEDs). Such materials are suitable as both light-emitting host materials, particularly for red light, hole transport materials, and electron blocking materials, as well as electron transport materials and hole blocking materials, resulting in significantly improved device luminous efficiency and longer device lifetime. This type of compound combination can also be used in the field of organic light-emitting displays. Specifically, in organic light-emitting displays, this type of compound combination can be used as a hole injection material or a hole transport material, and it can also be used as a light-emitting host material or a light-emitting material in fluorescent devices.

[0268] 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 host material composition, characterized in that, Compound N, which has the structure shown in formula (1), and compound M, which has the structure shown in formula (2); Equation (1): ; In equation (1), X is selected from O, S, Se, NAr, or CR. 6 R 7 Ar is selected from aryl groups of C6-C30; R 6 -R 7 Each alkyl group is independently selected from C1-C5; R 1 -L 1 Ar 1 R 2 -L 2 Ar 2 R 3 -L 3 Ar 3 L 1 -L 3 Each component is independently selected from the linker, C6-C30 aryl groups; Ar 1 -Ar 3 At least one of them is The remaining Ar 1 -Ar 3 Each is independently selected from hydrogen and deuterium; Represents the connector key, where R 4 -L 4 Ar 4 R 5 -L 5 Ar 5 L 4 -L 5 Each is independently selected from the linking bond, C6-C30 arylene, C3-C30 heteroarylene, Ar 4 -Ar 5 Each is independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Equation (2): ; In the above formula (2), X 1 -X 14 Each is independently selected from N or CR 8 R 8 Selected from hydrogen or deuterium; L is selected from connector; Ar 8 -Ar 9 Each is independently 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 two of deuterium, C1-C6 alkyl, C6-C30 aryl, and C3-C30 heteroaryl. When X 1 -X 14 All are CR 8 At that time, Ar 8 -Ar 9 The naphthyl group may be substituted or unsubstituted at the same time.

2. The composition according to claim 1, characterized in that, In the above formula (2), X 1 -X 14 One of them is selected from N, and the rest are CR. 8 ; or X 1 -X 6 One of them is selected from N, and the rest are CR. 8 X 7 -X 14 One of them is selected from N, and the rest are CR. 8 ; or, X 1 -X 14 All selected from CR 8 When there are multiple R 8 At that time, they exist independently and may be the same or different; R 8 The definition is the same as in claim 1; Ar 8 -Ar 9 Each group is independently selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluoranyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl.

3. The composition according to claim 1, characterized in that, The structure of compound M is shown in any one of formulas 2-1 to 2-5; wherein: 。 4. The composition according to claim 3, characterized in that, The compound M is preferably the structure shown in Formula 2-4 or Formula 2-5.

5. The composition according to any one of claims 1-4, characterized in that, The structure of compound M is shown as any one of M-1 to M-388 below; wherein: 。 6. The composition according to any one of claims 1-4, characterized in that, The structure of compound M is shown in any of the following M-469 to M-491: 。 7. The composition according to claim 1, characterized in that, The Ar 4 -Ar 5 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, phenylene, dibenzofuranyl, benzonaphthiofuranyl, dibenzothiophene, dibenzoselenophenolyl, dimethylfluorenyl, spirodifluorenyl, fluoranyl, carbazoyl, phenylcarbazoyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, pyridyl, pyrimidinyl, triazineyl.

8. The composition according to claim 1, characterized in that, The Ar 4 -Ar 5 Each independently selected and ; Among them, R T1 -R T5 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or R T1 -R T5 Any two adjacent rings can fuse to form ring A; ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, and substituted or unsubstituted phenanthrene rings. In this case, the substituents in the substituted benzene ring, substituted naphthalene ring, and substituted phenanthrene ring are selected from deuterium; R T6 Independently selected from hydrogen, deuterium, substituted or unsubstituted C3-C30 heteroaryl groups; Y selected from O, S, CR 6 R 7 ;where R 6 R 7 The definition is the same as that 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-C6 alkyl, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl groups are selected from deuterium.

9. The composition according to claim 1 or any one of 7-8, characterized in that, The Ar is selected from aryl groups of C6-C30; And / or, R 6 R 7 Each is independently selected from substituted or unsubstituted C1-C5 alkyl groups.

10. The composition according to claim 9, characterized in that, The Ar is selected from substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, triphenylene, and hydroxyl.

11. The composition according to any one of claims 1 or 7-8, characterized in that, L 1 -L 3 Each is independently selected from the linker, C6-C30 aryl groups; And / or, the remaining Ar 1 -Ar 3 Selected from hydrogen and deuterium.

12. The composition according to claim 11, characterized in that, L 1 -L 3 Each is independently selected from the linking bond, phenylene, naphthylene, triphenylene, or biphenylene; or, L 1 -L 3 Each is selected independently from the connector key.

13. The composition according to claim 12, characterized in that, L 1 Selected from the link key, L 2 Selected from phenylene, naphthylene, triphenylene, biphenylene, L 3 For connection keys.

14. The composition according to claim 1, characterized in that, The structure of compound N is shown in any of Formulas 1-1 to 1-17: ； Where R 1 -R 7 L 1 -L 3 The definition of Ar is the same as that in claim 1 or any one of claims 8-11.

15. The composition according to claim 1, characterized in that, The structure of compound N represented by formula (1) is shown as any one of N-1 to N-929: 。 16. The composition according to claim 1, characterized in that, The mass ratio of compound N to compound M is 9:1 to 1:

9.

17. The composition according to claim 16, characterized in that, The mass ratio of compound N to compound M is 2:8-8:

2.

18. The composition according to claim 17, characterized in that, The mass ratio of compound N to compound M is 3:7-7:

3.

19. The composition according to claim 18, characterized in that, The mass ratio of compound N to compound M is 4:6 to 6:

4.

20. The use of the organic electroluminescent host material composition according to any one of claims 1-19 in an organic electroluminescent device.

21. An organic electroluminescent material, characterized in that, An organic electroluminescent host material composition according to any one of claims 1-19.

22. An organic electroluminescent device, characterized in that, It includes an anode and a cathode, and an organic layer disposed between the anode and the cathode; said organic layer includes an organic electroluminescent host material composition according to any one of claims 1-19.

23. An organic electroluminescent device, characterized in that, Including the organic electroluminescent device as described in claim 22.

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