Organic electroluminescent host material composition, luminescent device and application

Abstract

The invention discloses an organic electroluminescent compound, a composition, a luminescent device and application, and the organic electroluminescent compound is a compound M with a structure as shown in a formula (2). When the compound M and the compound N are matched with each other to serve as the organic electroluminescent main body material of the organic light-emitting device, the turn-on voltage of the organic light-emitting device can be obviously reduced, the light-emitting efficiency is obviously improved, and the service life is obviously prolonged.

Description

[0001] This application is a divisional application of the application with the application date of June 30, 2023, the application number of 202310800187.2, and the invention name of an organic electroluminescence host material composition, a light-emitting device and application. TECHNICAL FIELD

[0002] The present application relates to the field of organic electroluminescence, in particular to an organic electroluminescence host material composition, a light-emitting device and application. BACKGROUND

[0003] An organic electroluminescence device (OLED) converts electrical energy into light by applying electricity to an organic electroluminescence material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic electroluminescence device can include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The various materials used in the organic layer are divided into 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, electron injection materials, etc. based on the functions achieved by each layer. In an organic electroluminescence device, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons. Organic light-emitting compounds move to the excited state by energy and emit light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0004] Existing disclosed organic light-emitting compounds include amine derivatives of indenotriphenylene, triazine electron transport materials, etc., such as an amine derivative based on indenotriphenylene disclosed in US20200115369A1, a triazine electron transport material, its preparation method and application disclosed in CN113004295A, etc. The existing disclosed amine derivatives based on indenotriphenylene can be used as organic electroluminescence devices for charge transport layer and electron blocking layer.

[0005] However, the functional materials composed of the existing organic light-emitting compounds all have the problems of low stability, unbalanced carrier mobility, etc., which cause the problems of high driving voltage, low luminous efficiency, short service life, etc. of the organic electroluminescence diode, and seriously limit the application of the organic electroluminescence diode. SUMMARY

[0006] Therefore, the technical problem to be solved by the present application is to overcome the problems of the prior art, i.e. the low stability of the organic electroluminescent material, the unbalanced carrier mobility leading to a high driving voltage of the light-emitting device, so as to provide an organic electroluminescent host material composition, a light-emitting device and application solving the above problems.

[0007] An organic electroluminescent compound is a compound M of the structure shown in formula (2), Formula (2): ; In the formula (2), X 1 -X 14 are each independently selected from N or CR 8 , R 8 is selected from hydrogen or deuterium; L is selected from a bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group; Ar 8 -Ar 9 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; The substituents in the substituted C6-C30 arylene group, the substituted C3-C30 heteroarylene group, the substituted C6-C30 aryl group, and the substituted C3-C30 heteroaryl group 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; When X 1 -X 14 are each CR 8 , Ar 8 -Ar 9 are not naphthyl groups which are substituted or unsubstituted.

[0008] In the formula (2), X 1 -X 14 are each independently selected from N, and the rest are CR 8 ; or X 1 -X 6 are each independently selected from N, and the rest are CR 8 , X 7 -X 14 are each independently selected from N, and the rest are CR 8 ; or, X 1 -X 14 are all selected from CR 8 ; when there are multiple R 8 , they each exist independently and can be the same or different.

[0009] Ar 8 -Ar9 each independently selected from the group consisting of hydrogen, deuterium, and substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl.

[0010] Ar 8 -Ar 9 each independently selected from the group consisting of hydrogen, deuterium, and substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, benzocarbazolyl, benzocarbazolyl, dibenzocarbazolyl.

[0011] The structure of the compound M is shown in any one of Formula 2-1 to Formula 2-5:

[0012]

[0013] wherein X 1 -X 14 , Ar 8 -Ar 9 and L are the same as defined above.

[0014] The structure of the compound M is shown in any one of Formula 2-6 to Formula 2-28:

[0015]

[0016]

[0017]

[0018] wherein X 1 -X 14 , Ar 8 -Ar 9 and L are the same as defined above.

[0019] The structure of the compound M is shown in any one of M-1 to M-388.

[0020] wherein the structures of M-1 to M-388 are as follows:

[0021] .

[0022] The structure of the compound M is shown in any one of M-389 to M-619 below.

[0023] wherein the structures of M-389 to M-619 are as follows:

[0024] .

[0025] An organic electroluminescence host material composition comprising a compound N having a structure shown in formula (1) and a compound M having a structure shown in formula (2) described above; Formula (1): ; In the formula (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, substituted or unsubstituted C3-C60 heteroaryl; R 6 -R 7 each independently is selected from a hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R 1 is -L 1 Ar 1 , R 2 is -L 2 Ar 2 , R 3 is -L 3 Ar 3 ; L 1 -L 3each independently selected from the group consisting of a bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar 1 -Ar 3 at least one of , represents a bond, said R 4 is -L 4 Ar 4 , R 5 is -L 5 Ar 5 ; L 4 -L 5 each independently selected from the group consisting of a bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, Ar 4 -Ar 5 each independently selected from the group consisting of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the remaining Ar 1 -Ar 3 each independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.

[0026] in formula (1), It can be understood that R1 in the application can be substituted on ring B, or can be substituted on ring C, R2 can be substituted on ring D, and R3 can be substituted on ring E.

[0027] Preferably, the Ar 4 -Ar 5 each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylenyl, chrysenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, pyridyl, pyrimidyl, triazinyl.

[0028] the Ar 4 -Ar 5 each independently selected from the group consisting of and ; wherein 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; 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; Preferably, ring A is selected from substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, and substituted or unsubstituted phenanthrene rings.

[0029] 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, triphenylene, phenylene, phenylene, dibenzofuranyl, and dibenzothiopheneyl. 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.

[0030] 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; And / or, L 4 -L 5 Each aryl group is independently selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups; optionally, L4 -L 5 each independently selected from a single bond, phenylene, naphthylene, further optionally, L 4 -L 5 each independently selected from a single bond; and / or, the remaining Ar 1 -Ar 3 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0031] said compound N has a structure as shown in any one of formula 1-1 to formula 1-17;

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] wherein R 1 -R 7 , L 1 -L 3 , Ar is as defined above.

[0038] said compound N has a structure as shown in any one of N-1 to N-935.

[0039] said N-1 to N-935 have structures as shown below:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] .

[0049] The mass ratio of the compound N to the compound M is 9:1-1:9; preferably 2:8-8:2; more preferably 3:7-7:3, further preferably 4:6-6:4.

[0050] The use of the above-mentioned organic electroluminescence host material composition in an optical device, preferably in an organic electroluminescence device.

[0051] Preferably, the optical device comprises any one of an organic electroluminescence device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quencher device, a light emitting electrochemical cell, an organic laser diode, or an organic photoreceptor.

[0052] An organic electroluminescence material comprising the above-mentioned organic electroluminescence compound or organic electroluminescence host material composition. Preferably, the organic electroluminescence material further comprises a dopant material. Preferably, the dopant material comprises a phosphorescent dopant comprising a transition metal-containing complex.

[0053] An organic electroluminescence device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode; the organic layer comprising the above-mentioned organic electroluminescence compound or organic electroluminescence host material composition.

[0054] Preferably, the organic layer comprises, stacked in order from the anode side to the cathode side, 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. An organic electroluminescent device comprising the organic electroluminescent device described above.

[0055] In the present application, unless otherwise explicitly stated, the substituents of each structure 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.

[0056] The term "organic electroluminescent material" disclosed in the present application means a material that can be used in an organic electroluminescent device and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary 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.

[0057] The organic electroluminescent material disclosed in the present application can include one organic electroluminescent material, or can include a plurality of organic electroluminescent materials, wherein the plurality of organic electroluminescent materials means a material including a combination of at least two organic electroluminescent materials, which can be included in any layer constituting the organic electroluminescent device. It can mean both a material included before the organic electroluminescent device (for example, before vapor deposition) and a material included after the organic electroluminescent device (for example, after vapor deposition). For example, the material can be a combination of at least two compositions, which can be included in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary 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 plurality of organic electroluminescent materials can be included in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0058] The term "organic electroluminescent host material composition" disclosed in the present invention means an organic electroluminescent material comprising a combination of at least two host materials. It can mean both materials before being included in an organic electroluminescent device (for example, before vapor deposition) and materials after being included in an organic electroluminescent device (for example, after vapor deposition). The composition disclosed in the present invention can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds among the plurality of host materials included in the composition disclosed in the present invention can be included in one light-emitting layer, or can be included in different light-emitting layers, respectively. For example: when two or more host materials are included in one layer, the layer can be formed by mixed evaporation, or can be formed by separate co-evaporation at the same time.

[0059] "Halogen" in the present invention can include fluorine, chlorine, bromine, or iodine.

[0060] "C1-C30 alkyl" in the present invention means a monovalent substituent derived from a straight chain or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, i-pentyl, and hexyl.

[0061] "C3-C30 cycloalkyl" in the present invention means a monocyclic or polycyclic hydrocarbon derived from a ring backbone having 1 to 30 carbon atoms, and the cycloalkane can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, adamantyl, etc.

[0062] Aryl and arylene in the present invention include monocyclic, polycyclic, or fused ring aryl groups, which can be interrupted by short non-aromatic units between the rings, and can contain a spiro structure, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, phenylphenanthryl, binaphthyl, phenylnaphthyl, naphthylphenyl, anthryl, indenyl, triphenylene, naphthacene, pyrene, perylene, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.

[0063] The heteroaryl group and the heteroarylene group in the present application include monocyclic, polycyclic or fused ring heteroaryl groups, and the rings can be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Examples include, but are not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoaxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like.

[0064] The "substituted" in the present application means that a hydrogen atom in a compound is replaced with another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced with the substituent. Also, it includes a case where the hydrogen atom is replaced with a group formed by the connection 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 connection 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 connected.

[0065] The hydrogen atom in the present application includes protium, deuterium and tritium, unless otherwise specified.

[0066] The group of the present application defines the range of the number of carbon atoms, and the number of carbon atoms should be any integer within the defined range, for example, C6-C30 aryl group means that the number of carbon atoms of the aryl group can be any integer within the range of 6 to 60, for example, 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, and the like.

[0067] When the group in the present application has a substituent, the substituent is each independently selected from the group consisting of deuterium, halogen, cyano, nitro, unsubstituted or R'-substituted C1-C4 linear or branched alkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and unsubstituted or R'-substituted C6-C20 arylamine; R' is selected from the group consisting of deuterium, halogen, cyano and nitro.

[0068] By including a specific combination of the compound of the present application as a host material composition, an organic electroluminescent device having improved luminous efficiency and lifespan characteristics compared to a conventional organic electroluminescent device can be provided, and a display system or a lighting system using the same can be manufactured.

[0069] The technical scheme of the present application has the following advantages: 1. The present application provides an organic electroluminescent compound, which is a compound M having the structure shown in formula (2). The compound M has significantly better performance than the CBP and REF-1 disclosed in the prior art, and can have a lower turn-on voltage, i.e. a lower driving voltage, when prepared into a device. The compound M can be used in combination with a compound N having a polycyclic heteroaromatic group containing triphenylene in the present application, i.e. a compound N, as an organic electroluminescent host material for an organic light-emitting device, and the combination can significantly reduce the turn-on voltage of the organic light-emitting device, significantly improve the luminous efficiency, and significantly prolong the service life. Therefore, the compound M having the structure shown in formula (2) in the present application can be used in combination with the compound N to significantly improve the performance of the light-emitting host material, and can be used to produce an organic electroluminescent device having high luminous efficiency and long service life.

[0070] 2. The present application provides an organic electroluminescent host material composition, which comprises a compound M having the structure shown in formula (2) and a compound N having the structure shown in formula (1). The light-emitting host material formed by the combination of the compound M and the compound N can be used in a light-emitting material to prepare a light-emitting device. The combination of the compound M and the compound N can synergistically reduce the turn-on voltage of the light-emitting device, significantly improve the luminous efficiency, and significantly prolong the service life. The combination of the compound M having the structure shown in formula (2) and the compound N having the structure shown in formula (1) can make the light-emitting device have a lower driving voltage (below 3.44 V), a higher current efficiency (above 24 Cd / A), and a longer service life (above 260 h). DETAILED DESCRIPTION

[0071] The following examples are provided to better further understand the present application and are not limited to the best mode, and do not limit the content and scope of protection of the present application. Any person who obtains any product the same as or similar to the present application under the inspiration of the present application or by combining the present application with other prior art features falls within the scope of protection of the present application.

[0072] If the specific experimental steps or conditions are not specified in the examples, the operations or conditions can be performed according to the conventional experimental steps described in the literature in the art. If the reagents or instruments are not specified by the manufacturer, they are conventional reagent products that can be obtained from the market.

[0073] Example 1 An organic electroluminescent compound is compound M-17, and the synthesis process is as follows:

[0074] Take a 50-milliliter two-necked round-bottom flask and put in a stirrer and an upper reflux tube, dry it after filling with nitrogen, respectively add compound M17-A (19.8 mmol, CAS: 1884145-03-2), M17-B (20.75 mmol, CAS: 1883265-32-4), tetrakis triphenylphosphine palladium (0.396 mmol), potassium carbonate (39.6 mmol), 35 milliliters of toluene, 15 milliliters of ethanol and 15 milliliters of distilled water, and stir the mixture at 90 degrees Celsius for 8 hours. After the reaction is completed, the mixture is added dropwise into methanol, and the resulting solid is filtered. The resulting solid is purified by column chromatography to obtain compound M-17 (8.5 g, yield: 75%).

[0075] Elemental analysis: C 41 H 25 N3O; Theory: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found: C, 85.52; H, 4.38; N, 7.32; HRMS (ESI) m / z (M+): Theory: 575.20; Found: 576.34.

[0076] Example 2 An organic electroluminescence compound is compound M-296, and its synthesis process is as follows: (I) Synthesis of intermediate M296-A, the synthesis route is as follows:

[0077] Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, add intermediate M296-1 (2-bromoquinoline, CAS: 2005-43-8, 20 g) and 200 mL of anhydrous tetrahydrofuran, under the protection of nitrogen, cool to -78℃, and control the temperature to add n-butyllithium (1.6M, 45.2 mL) dropwise, stir for 1 h after dropwise addition, control the temperature to -78℃, and dropwise add triisopropyl borate (19.52 g), transfer to room temperature after dropwise addition, and react for 12 h, dropwise add hydrochloric acid solution (36% concentration hydrochloric acid 6.5 mL + 24 mL water), extract the reaction solution with 50 mL of ethyl acetate and 25 mL of water, dry the organic phase with 50 mL of n-hexane, and backwash for 1 h at room temperature, filter and dry to obtain intermediate M296-2, 15 g.

[0078] Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, was placed intermediate M296-2 (15 g), intermediate 7-bromo-l-chloronaphthalene (21.9 g), potassium carbonate (16.6 g) and tetrakis triphenylphosphine palladium (2.0 g), toluene (80 mL), ethanol (35 mL) and water (35 mL) were added, the reaction was heated to 85 °C under nitrogen for 6 h, the reaction solution was extracted with 50 mL ethyl acetate and 25 mL water, the organic phase was passed through a column to obtain intermediate M296-3, 15 g.

[0079] Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, was placed intermediate M296-3 (15 g), bis(pinacolato)diboron (15.8 g), potassium acetate (10 g) and Pd(dppf)Cl2(0.64 g), 1,4-dioxane (150 mL) was added, the reaction was heated to 110 °C under nitrogen for 4 h, the reaction solution was extracted with 100 mL toluene and 100 mL water, the organic phase was passed through a column to obtain intermediate M296-A, 16 g.

[0080] (II) Synthesis of compound M-296, the synthetic route is as follows:

[0081] Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, was placed intermediate M296-A (16 g), intermediate M296-B (2-chloro-4,6-diphenyl-l,3,5-triazine, CAS: 3842-55-5, 11.2 g), potassium carbonate (11.6 g) and tetrakis triphenylphosphine palladium (1.3 g), toluene (110 mL), ethanol (50 mL) and water (50 mL) were added, the reaction was heated to 85 °C under nitrogen for 6 h, the reaction solution was filtered with water and ethanol at room temperature, and the product M296 was obtained after drying, 16 g (yield 78%).

[0082] Elemental analysis: C 34 H 22 N4Calcd: C, 83.93; H, 4.56; N, 11.51; Found: C, 83.95; H, 4.56; N, 11.49; HRMS (ESI) m / z (M+): Calcd: 486.18; Found: 487.12.

[0083] Example 3 An organic electroluminescence compound is compound M-381, and the synthesis process is as follows: (I) Synthesis of intermediate M381-B, the synthetic route is as follows:

[0084] Into a 250 mL three-necked flask, equipped with a thermometer and magnetic stirring, was placed intermediate M381-1 (CAS: 5332-25-2, 20 g), and 200 mL of anhydrous tetrahydrofuran, under nitrogen protection, cooling to -78 °C, temperature control dropwise added n-butyllithium (1.6 M, 45.2 mL), after dropwise added stirring for 1 h, again temperature control -78 °C dropwise added triisopropyl borate (19.52 g), after dropwise added to room temperature reaction 12 h, dropwise added hydrochloric acid solution (36% concentration hydrochloric acid, 6.5 mL + 24 mL water), the reaction solution was added 50 mL of ethyl acetate, 25 mL of water extraction, the organic phase was dried and added 50 mL of n-hexane, refluxed for 1 h, filtered at room temperature, dried to give intermediate M381-2, 15 g.

[0085] Into a 250 mL three-necked flask, equipped with a thermometer and magnetic stirring, was placed intermediate M381-2 (15 g), raw material M367-a (CAS: 99455-15-9, 21 g), potassium carbonate (16.6 g) and tetrakis triphenylphosphine palladium (2.0 g), added toluene (80 mL), ethanol (35 mL) and water (35 mL), under nitrogen protection, heating to 85 °C for 6 h, the reaction solution was added 50 mL of ethyl acetate, 25 mL of water extraction, the organic phase was stirred and columned to give intermediate M381-3, 13 g.

[0086] Into a 250 mL three-necked flask, equipped with a thermometer and magnetic stirring, was placed intermediate M381-3 (13 g), and 200 mL of anhydrous tetrahydrofuran, under nitrogen protection, cooling to -78 °C, temperature control dropwise added n-butyllithium (1.6 M, 40 mL), after dropwise added stirring for 1 h, again temperature control -78 °C dropwise added triisopropyl borate (17 g), after dropwise added to room temperature reaction 12 h, dropwise added hydrochloric acid solution (36% concentration hydrochloric acid, 6.5 mL + 24 mL water), the reaction solution was added 50 mL of ethyl acetate, 25 mL of water extraction, the organic phase was dried and added 50 mL of n-hexane, refluxed for 1 h, filtered at room temperature, dried to give intermediate M381-4, 12 g.

[0087] Into a 250 mL three-necked flask, equipped with a thermometer and magnetic stirring, was placed intermediate M381-4 (12 g), raw material M381-b (CAS: 112719-97-8, 11 g), potassium carbonate (11 g) and tetrakis triphenylphosphine palladium (1.2 g), added toluene (80 mL), ethanol (35 mL) and water (35 mL), under nitrogen protection, heating to 85 °C for 6 h, the reaction solution was added 50 mL of ethyl acetate, 25 mL of water extraction, the organic phase was stirred and columned to give intermediate M381-B, 16 g.

[0088] (ii) Synthesis of compound M-381, the synthesis route is as follows:

[0089] Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, intermediate M381-B (16 g), raw material M381-A (6.85 g, CAS: 395087-89-5), potassium carbonate (9 g) and tetrakis triphenylphosphine palladium (1.0 g) were added, and then toluene (80 mL), ethanol (35 mL) and water (35 mL) were added. Under the protection of nitrogen, the reaction was heated to 85°C for 6 h. The reaction solution was extracted with 50 mL of ethyl acetate and 25 mL of water, and the organic phase was separated by column chromatography to obtain the final product M-381, 15 g (yield 74%).

[0090] Elemental analysis: C 43 H 25 N 50 Theoretical value: C, 82.28; H, 4.01; N, 11.16; O, 2.55; Found: C, 82.30; H, 4.01; N, 11.14; HRMS (ESI) m / z (M+): Theoretical value: 627.21; Found: 628.13.

[0091] Example 4 An organic electroluminescence compound is compound M-76, M-108, M-145, M-253, M-308, M-365 or M-371, and the synthesis process of each compound M is as follows: Into a 250 mL three-necked flask equipped with a thermometer and magnetic stirring, intermediate M381-B (16 g), raw material M381-A (6.85 g), potassium carbonate (9 g) and tetrakis triphenylphosphine palladium (1.0 g) were added, and then toluene (80 mL), ethanol (35 mL) and water (35 mL) were added. Under the protection of nitrogen, the reaction was heated to 85°C for 6 h. The reaction solution was extracted with 50 mL of ethyl acetate and 25 mL of water, and the organic phase was separated by column chromatography to obtain the final product.

[0092] The raw material Mn-B, the raw material Mn-A, the structure of the product and the yield are shown in Table 1. The elemental analysis results of the prepared compounds are shown in Table 2.

[0093] Table 1

[0094]

[0095]

[0096]

[0097] Table 2 .

[0098] Example 5 An organic electroluminescence host material composition, comprising a compound N containing polycyclic heteroaromatic group with triphenylene and a compound M, the compound M is as any one of M-1 to M-619, preferably selected from one of the organic electroluminescence compounds prepared in Examples 1-4; the compound N in the composition is a compound as any one of N-1 to N-935, preferably any one of N-4, N-5, N-14, N-20, N-37, N-46, N-65, N-68, N-78, N-113, N-275, N-281, 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, N-918; the synthesis process of each of the above compounds N is as follows: 1. Synthesis route of N-4

[0099] 1.1 Synthesis of intermediate N-4B’ Into a 500 mL three-necked flask equipped with magnetic stirring, 20 g (1.0 eq) of 4a (CAS: 444796-09-2), 9.87 g (1.0 eq) of 4b (CAS: 4688-76-0), 1.7 g (2% eq) of Pd(PPh3)4, 8.37 g (2.0 eq) of NaHCO3, 180 mL of tetrahydrofuran (4a: tetrahydrofuran = 1 g: 9 mL) and 60 mL of ultrapure water (4a: ultrapure water = 1 g: 3 mL) were added under nitrogen blowing, and the reaction was completed at 65 ℃ for 2 h. Column purification was performed to obtain 10 g of product N-4B’.

[0100] 1.2 Synthesis of intermediate N-4B Into a 250 mL three-necked flask equipped with magnetic stirring, 10 g (1.0 eq) of intermediate N-4B', 20.5 g (6.0 eq) of anhydrous FeCl3, 100 mL of anhydrous dichloromethane (N-4B' : dichloromethane = 1 g : 10 mL) were added under nitrogen at -10 °C for 1 h. The reaction was complete. Purification by column gave 7 g of product N-4B.

[0101] 1.3 Synthesis of compound N-4 Into a 250 mL three-necked flask equipped with magnetic stirring, 7 g (1.0 eq) of N-4B, 4.0 g (1.1 eq) of N-4A (CAS: 35887-50-4), 0.27 g (2% eq) of Pd2(dba)3, 2.85 g (2.0 eq) of t-BuONa, 70 mL of anhydrous toluene (N-4B : anhydrous toluene = 1 g : 10 mL) were added under nitrogen at 100 °C for 2 h. The reaction was complete. Purification by column gave 5 g of product N-4.

[0102] Elemental analysis: C 48 H 32 N2Theoretical: C, 90.54; H, 5.07; N, 4.40; Found: C, 90.53; H, 5.08; N, 4.41; HRMS (ESI) m / z (M+): Theoretical: 636.26; Found: 637.55.

[0103] 2. Synthesis route of N-5

[0104] Into a 250 mL three-necked flask equipped with magnetic stirring, 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, 70 mL of anhydrous toluene (intermediate N-4B : anhydrous toluene = 1 g : 10 mL) were added under nitrogen at 100 °C for 2 h. The reaction was complete. Purification by column gave 5 g of product.

[0105] Elemental analysis: C 52 H 34N2Theoretical value: C, 90.93; H, 4.99; N, 4.08; Found: C, 90.92; H, 4.98; N, 4.10; HRMS (ESI) m / z (M+): Theoretical value: 686.27; Found: 687.22.

[0106] 3. Synthesis route of N-14

[0107] Into a 250 mL three-necked flask equipped with magnetic stirring, 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, 70 mL of anhydrous toluene (intermediate 2: anhydrous toluene = 1 g: 10 mL) were added under nitrogen blowing, and the reaction was completed at 100 °C for 2 h. Column purification gave 5 g of product.

[0108] Elemental analysis: C 50 H 32 N2Theoretical value: C, 90.88; H, 4.88; N, 4.24; Found: C, 90.86; H, 4.88; N, 4.26; HRMS (ESI) m / z (M+): Theoretical value: 660.25; Found: 661.37.

[0109] 4. Synthesis route of N-20, N-37, N-46, N-65, N-68, N-78, N-113, N-275, N-281, N-358, N-369, N-389 The same as the synthesis conditions of N-14, the difference is that the raw material N-nA, the raw material N-nB and the structure and yield of the product are different, as shown in Table 3; the elemental analysis results of the prepared compounds are shown in Table 4.

[0110] Table 3

[0111]

[0112]

[0113] Table 4 .

[0114] 5. Synthesis route of N-423

[0115] Into a 1000 mL three-necked flask equipped with mechanical stirring, reflux condenser, thermometer, 20 g of 423a (i.e. 4b), 29.9 g of 423b (CAS: 67019-91-4), 2.3 g of Pd[P(C6H5)3]4, 27.9 g of K2CO3, 280 mL of toluene, 120 mL of H2O, 120 mL of ethanol were added. Nitrogen was replaced for three times, and the reaction was carried out at 85°C under the protection of nitrogen. The reaction was carried out for 150 min from the beginning of temperature rising. After the reaction was completed, 120 mL of water was added to quench the reaction, and after the liquid separation, the oil was obtained by rotary evaporation (wet weight 44 g). After vacuumizing, 25 g of N-423B’ was obtained.

[0116] Into a 2 L three-necked flask equipped with stirring, thermometer, 25 g of N-423B’ crude product (oil) and 750 mL of dichloromethane (N-423B’: DCM = 1 g: 30 mL) were added. The temperature was controlled at -5°C, and iron trichloride was added in two batches, with 3 equivalents of iron trichloride added every 15 min, and the temperature was controlled at -5°C. After the reaction was completed, 750 mL of ethanol (N-423B’: ethanol = 1 g: 30 mL) was slowly added, and the temperature was controlled below 0°C. After the addition was completed, stirring was continued for 0.5 h, and yellow-white solid was precipitated. Filtration was performed, and the filter cake was washed with 250 mL of ethanol (N-423B’: ethanol = 1 g: 1 mL) to obtain yellow solid. After being dissolved in 1.75 L of chlorobenzene, the solution was crystallized by natural cooling to 60°C, and 250 mL of n-hexane solution was added dropwise to obtain the crude product N-423B, 20 g.

[0117]

[0118] Into a 1000 mL three-necked flask equipped with mechanical stirring, reflux condenser, thermometer, 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 t-BuONa, 500 mL of toluene were added. Nitrogen was replaced for three times, and the reaction was carried out at 110°C under the protection of nitrogen. The reaction was carried out for 120 min from the beginning of temperature rising. After the reaction was completed, 120 mL of water was added to quench the reaction, and after the liquid separation, rotary evaporation was performed, and after column chromatography and drying, 35 g of crude product N-423 was obtained.

[0119] Elemental analysis: C 42 H 27NO; Calculated: C, 89.81; H, 4.85; N, 2.49; O, 2.85; Found: C, 89.78; H, 4.86; N, 2.51; HRMS (ESI) m / z (M+): Calculated: 561.21; Found: 562.29.

[0120] 6. Synthesis route of N-425

[0121] Into a 500 mL three-necked flask equipped with mechanical stirring, reflux condenser, thermometer, 14 g N-425A (CAS: 1401351-43-6), 18.8 g N-423B (CAS: 2035812-74-7), 0.86 g Pd2(dba)3, 1.9 g sphos, 9.1 g t-BuONa, 150 mL toluene were added. The flask was purged with nitrogen for three times, and then the reaction was carried out at 110°C under nitrogen protection. The reaction was carried out for 120 min from the beginning of temperature rising. After the reaction was completed, 150 mL water was added to quench the reaction, and then the reaction mixture was separated, dried, and then slurried with ethanol, and then the product was obtained by recrystallization from toluene. The yield of the crude product N-425 was 16 g.

[0122] Elemental analysis: C 46 H 29 NO; Calculated: C, 90.32; H, 4.78; N, 2.29; O, 2.62; Found: C, 90.30; H, 4.77; N, 2.32; HRMS (ESI) m / z (M+): Calculated: 611.22; Found: 612.45.

[0123] 7. Synthesis route of 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 The same synthesis conditions as N-425 were used, except that the raw materials N-nA, raw materials N-nB, and 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.

[0124] Table 5

[0125] Table 6

[0127] 8. Synthesis route of N-912

[0128] 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 Na2C03, 150 ml EtOH and 300 ml toluene was degassed and placed under nitrogen and then heated at 100 °C for 12 hours. After completion of the reaction, the mixture was allowed to cool 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 on silica gel to give the product 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene as a white solid (26.8 g, 63.0 mmol, 63%).

[0129] In a 3000 ml three necked flask, degassed and filled with nitrogen, 26.8 g (60 mmol) 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene was dissolved in anhydrous dichloromethane (1500 ml), then 97.5 g (600 mmol) iron (III) chloride was added and the mixture was stirred for one hour. To the mixture 500 ml of methanol was added and the organic layer was separated and the solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (hexane-dichloromethane) to give N-912A (12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene) as a white solid (10.7 g, 25.3 mmol, 40%).

[0130]

[0131] A mixture of 20 g (41.3 mmol) N-(diphenyl-4-yl)-9,9'-spirobifluorene-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 under nitrogen overnight. After the end of the reaction, it was subsequently cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica gel (hexane-dichloromethane) to obtain 26.3 g (yield 43%) of product as a white solid.

[0132] A mixture of 10 g (15.6 mmol) N-(diphenyl-4-yl)-N-(4-bromo-phenyl)-9,9'- spirobi[fluorene]-2-amine, 4.75 g (18.72 mmol) bis(pinacolato)diboron, 0.18 g (0.156 mmol) tetrakis(triphenylphosphine)palladium, 2 g (20.28 mmol) potassium acetate and 300 ml 1,4-dioxane was degassed and left under nitrogen and subsequently heated at 90°C for 16 h. After the end of the reaction, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the product was purified by column using a mixture of hexane and ethyl as eluent to obtain 8.77 g of light yellow product N-912B (N-(diphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9,9'- spirobifluorene-2-amine, yield 82%).

[0133]

[0134] 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-(diphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9,9'- spirobifluorene-2-amine (N-912B), 0.41 g (0.35 mmol) tetrakis(triphenylphosphine)palladium, 23 ml 2M Na2C03, 100 ml EtOH and 200 ml toluene was degassed and left under nitrogen and then heated at 100 °C for 8 hours. After finishing the reaction, the mixture was cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica gel (hexane-dichloromethane) to give the product 17.5 g (N-912, yield 55%) as a yellow solid.

[0135] Elemental analysis: C 70 H 47 N Theoretical values: C, 93.20; H, 5.25; N, 1.55; Found: C, 93.16; H, 5.27; N, 1.57; HRMS (ESI) m / z (M+): Theoretical: 901.37; Found: 902.21.

[0136] 9. Synthesis route of N-895

[0137] 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-(diphenyl-4-yl)-9,9'-spirobifluorene-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 toluene was refluxed under nitrogen overnight. After finishing the reaction, it was then cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica gel (hexane-dichloromethane) to give the product 5.8 g (N-895, yield 60%) as a yellow solid.

[0138] Elemental analysis: C 64 H 43N Theory: C, 93.06; H, 5.25; N, 1.70; Found: C, 93.02; H, 5.25; N, 1.73; HRMS (ESI) m / z (M+): Theory: 825.34; Found: 826.19.

[0139] 10. Synthetic route of N-899, N-901, N-906, N-918 The same as the synthesis conditions of N-895, except that the raw material N-nA, raw material N-nB and the structure of the product and the yield are different, as shown in Table 7 below; the elemental analysis results of the prepared compounds are shown in Table 8.

[0140] Table 7

[0141]

[0142] Table 8 .

[0143] Example 6 An organic electroluminescence device, its structure from bottom to top in turn: substrate with anode layer, hole injection layer (HIL), hole transport layer (HTL), light-emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL) and cathode. The specific preparation process is as follows: (1) Substrate cleaning: the glass substrate coated with transparent ITO is treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%) by ultrasonic treatment, washed in deionized water, ultrasonic deoiled in acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0144] (2) Evaporating hole injection layer: Put the above glass substrate with anode layer into the vacuum chamber, vacuumize to 1×10 -6 to 2×10 -4 Pa, vacuum evaporate the mixture of NDP-9 and HT on the anode layer film, wherein the mass ratio of NDP-9 to HT is 3:97, as a hole injection layer, and the evaporation thickness is 10 nm; wherein, the structures of NDP-9 and HT are as follows: , .

[0145] (3) Evaporate hole transport layer (material HT) on the hole injection layer, and the evaporation film thickness is 80 nm.

[0146] (4) Evaporate a light-emitting layer on the hole transport layer, and the specific preparation method is as follows: evaporate the light-emitting host material and the dopant material (piq)2Ir(acac) by co-evaporation, and the composition of the host material and the dopant material is shown in Table 9; Table 9

[0147] The total film thickness of evaporation is 38 nm; wherein, the structure of (piq)2Ir(acac) is as follows: .

[0148] (5) Evaporate an electron transport layer on the light-emitting layer, and the specific preparation method is as follows: evaporate the electron transport layer material by co-evaporation, and the material is ET-1 and LiQ with a mass ratio of 1:1, and the total film thickness of evaporation is 30 nm, wherein, the structures of ET-1 and LiQ are as follows: , .

[0149] (6) Evaporate an electron injection layer on the electron transport layer, and the material of the electron injection layer is LiQ, and the total film thickness of evaporation is 1 nm; (7) Evaporate Al on the electron injection layer, and the total film thickness of evaporation is 80 nm.

[0150] Comparative Example 1 The difference between this comparative example and Example 6 is that the composition of the host material used in step (5) in the process of preparing the device is different, and the specific composition is shown in Table 10; other steps and parameter conditions are the same as those of Example 6.

[0151] Table 10

[0152] In the above table, the structures of CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl, CAS: 58328-31-7) and REF-1 (CAS: 1070884-53-5) are as follows: , .

[0153] Experimental Example The devices prepared by using Example 6 and Comparative Example 1 are tested for performance, and the specific test conditions are as follows: The current, voltage, brightness, and light-emitting spectrum characteristics of the device are tested synchronously by using a PR 650 spectrum scanning brightness meter and a Keithley K 2400 digital source table system; Photoelectric property test condition: current density is 10 mA / cm 2 ; Lifetime test: current density is 50 mA / cm 2 , record time (in hours) when the device brightness drops to 95% of the original brightness.

[0154] The device performance test results are shown in Tables 11 and 12.

[0155] Table 11

[0156] Table 12

[0157] From the data corresponding to the examples and comparative examples in Table 12, it can be seen that the new compound M developed by the application has obviously more excellent performance than the CBP, REF-1 and the like disclosed in the prior art, and can have a lower turn-on voltage after being prepared into a device, i.e., a lower driving voltage in Tables 11 and 12.

[0158] From the data of device NM in Table 12, it can be seen that when the organic electroluminescent material is used as an organic functional layer material, the compound N and the compound M synergistically act together to significantly improve the performance of the device, which is more significant than the cooperation between other similar compounds disclosed in the prior art, see the device RC of the cooperation between REF-1 and CBP, the device N1C of the cooperation between N-4 and CBP, and the device M1C of the cooperation between M1 and CBP. At the same time, the above-mentioned effect can also be known from the data comparison in Table 11, that is, when the host material in the light-emitting material is selected as the cooperation between the compound N and the compound M, a more significant synergistic effect can be achieved. Compared with the use of the compound N or the compound M alone or the cooperation with other compounds as the organic electroluminescent host material, the combination of the compound N and the compound M has a significantly lower turn-on voltage, significantly improves the light-emitting efficiency of the device, and significantly increases the service life of the device. The finally prepared device has a lower driving voltage (below 3.44V), a higher current efficiency (above 24 Cd / A) and a higher lifetime (above 260h). As can be seen from the above, the compound M and the compound N developed by the present application can significantly improve the carrier injection efficiency, reduce the interlayer energy level difference, balance the electron and hole transport rate, effectively improve the efficiency of the organic electroluminescent diode, and prolong the service life of the organic electroluminescent diode. Such materials are suitable as light-emitting host materials, especially for red light host materials, hole transport materials, and electron blocking materials, and are also suitable as electron transport materials and hole blocking materials, so that the light-emitting efficiency of the device is greatly improved, and the service life of the device is long. The combination of such compounds can also be used in the field of organic electroluminescent display. Specifically, the combination of such compounds can be used as a hole injection material or a hole transport material in an organic electroluminescent display, and can also be used as a light-emitting host material or a light-emitting material in a fluorescent device.

[0159] Obviously, the above embodiments are only examples for clearly illustrating the present application, and are not intended to limit the embodiments. Based on the above description, other different forms of changes or variations can also be made by those skilled in the art. All the embodiments do not need to be exhausted here, and the obvious changes or variations derived therefrom are still within the protection scope of the present application.

Claims

1. An organic electroluminescent compound, characterized by For compounds M of the structure shown in formula (2), formula (2): ; X 1 -X 14 any one is selected from N, the rest is CR 8 ; or, X 1 -X 6 any one is selected from N, the rest is CR 8 , X 7 -X 14 any one is selected from N, the rest is CR 8 ; or, X 1 -X 14 all are selected from CR 8 ; R 8 selected from hydrogen or deuterium; L is selected from a bond; Ar 8 -Ar 9 each independently selected from substituted or unsubstituted C6-C30aryl, and substituted or unsubstituted C3-C30heteroaryl; the substituents in the substituted C6-C30 aryl, substituted C3-C30 heteroaryl are selected from the group consisting of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, one or a combination of two; when X 1 - X 14 are each CR 8 , Ar 8 - Ar 9 is not substituted or unsubstituted naphthyl.

2. The organic electroluminescence compound according to claim 1, wherein Ar 8 -Ar 9 each independently selected from the group consisting of hydrogen, deuterium, and substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl.

3. The organic electroluminescence compound according to claim 1 or 2, wherein the compound M is a compound of structure according to any one of formulae 2-1 to 2-3, 2-6 to 2-22: ， wherein X 1 -X 14 , Ar 8 -Ar 9 are as defined in claim 1 or 2.

4. The organic electroluminescence compound according to claim 1 or 2, wherein the compound M is a compound of structure according to any one of formulae 2-6, 2-8 to 2-20, 2-22, 2-3 or 2-25 to 2-28.

5. The organic electroluminescence compound according to claim 1 or 2, wherein the structure of the compound M is according to any one of M-1 to M-388: 。 6. The organic electroluminescence compound according to claim 1 or 2, wherein the structure of the compound M is according to any one of M-389 to M-619: 。 7. An organic electroluminescence host material composition characterized by comprising the compound according to any one of claims 1 to 6. a compound N comprising a structure according to formula (1) and a compound M according to formula (2) as defined in any one of claims 1 to 6; Formula (1): ; In the formula (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, substituted or unsubstituted C3-C60 heteroaryl; R 6 -R 7 are each independently selected from a hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R 1 is -L 1 Ar 1 , R 2 is -L 2 Ar 2 , R 3 is -L 3 Ar 3 ; L 1 -L 3 each independently is selected from the group consisting of a direct bond, a substituted or unsubstituted C6-C30arylene group, a substituted or unsubstituted C3-C30heteroarylene group; Ar 1 -Ar 3 at least one of which is , represents a direct bond, wherein R 4 is -L 4 Ar 4 , R 5 is -L 5 Ar 5 , L 4 -L 5 each independently is selected from the group consisting of a direct bond, a substituted or unsubstituted C6-C30arylene group, a substituted or unsubstituted C3-C30heteroarylene group, Ar 4 -Ar 5 each independently is selected from the group consisting of hydrogen, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C3-C30heteroaryl group; the remaining Ar 1 -Ar 3 each independently is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group.

8. The composition of claim 7, wherein, said Ar 4 -Ar 5 each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylenyl, xanthyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, dibenzoselenophenyl, triphenylenyl, dimethylfluorenyl, spirobifluorenyl, fluoranthenyl, carbazolyl, phenylcarbazolyl, diphenylfluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, pyridyl, pyrimidyl, triazinyl.

9. The composition of claim 7, wherein, said Ar 4 -Ar 5 each independently selected from and ; wherein R T1 -R T6 each independently is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30alkyl, substituted or unsubstituted C7-C30aralkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl, substituted or unsubstituted C4-C30heteroaralkyl, substituted or unsubstituted C3-C30cycloalkyl, substituted or unsubstituted C3-C30heterocycloalkyl, substituted or unsubstituted C3-C30cycloalkenyl, substituted or unsubstituted C1-C30alkoxy, substituted or unsubstituted C6-C30aryloxy, or R T1 -R T5 any two of which adjacent ones can be annulated to a C6-C30ring A; Y is selected from O, S, NAr, CR 6 R 7 ; wherein Ar, R 6 , R 7 are as defined in claim 5; when there are a plurality of R T1 -R T6 when there are a plurality of R T1 -R T6 each is independently of the others the same or different; Preferably, ring A is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring.

10. The composition according to any one of claims 7 to 9, characterized in that, Ar is selected from a substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl; preferably, selected from a substituted or unsubstituted group consisting of phenyl, naphthyl, biphenyl, terphenyl, triphenylene, fluorenyl, dibenzofuranyl, dibenzothiophenyl; and / or, R 6 , R 7 each independently is selected from substituted or unsubstituted C1-C5alkyl, substituted or unsubstituted C6-C30aryl.

11. The composition according to any one of claims 7-9, characterized in that, L 1 -L 3 are each independently selected from the group consisting of a bond, C6-C30arylene, preferably L 1 -L 3 are each independently selected from the group consisting of a bond, phenylene, naphthylene, triphenylene, biphenylene; further alternatively, L 1 is selected from the group consisting of a bond, L 2 is selected from the group consisting of phenylene, naphthylene, triphenylene, biphenylene, L 3 is a bond; preferably, L 1 -L 3 are each independently selected from the group consisting of a single bond; and / or, L 4 -L 5 each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene; alternatively, L 4 -L 5 each independently selected from a single bond, phenylene, naphthylene, further alternatively, L 4 -L 5 each independently selected from a single bond; and / or, the remaining Ar 1 -Ar 3 selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

12. The composition of claim 7, wherein, the structure of the compound N is according to any one of formulae 1-1 to 1-17; ； wherein R 1 -R 7 , L 1 -L 3 , Ar is as defined in any of claims 7-11.

13. The composition according to any one of claims 7-11, characterized in that, the structure of the compound N according to formula (1) is according to any one of N-1 to N-935: 。 14. The composition according to any one of claims 7 to 13, characterized in that, the mass ratio of the compound N to the compound M is 9:1 to 1:9; preferably 2:8 to 8:2; more preferably 3:7 to 7:3, further preferably 4:6 to 6:

4.

15. Use of an organic electroluminescence host material composition according to any one of claims 7 to 14 in an optical device, preferably in an organic electroluminescence device.

16. An organic electroluminescent material, characterized by An organic electroluminescence compound according to any one of claims 1 to 6 or an organic electroluminescence host material composition according to any one of claims 7 to 14.

17. An organic electroluminescent device, characterized by An organic electroluminescence device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode; the organic layer comprising an organic electroluminescence compound according to any one of claims 1 to 6 or an organic electroluminescence host material composition according to any one of claims 7 to 14.

18. An organic electroluminescent device, characterized by comprising An organic electroluminescence device according to claim 17.

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