Metal organic material as well as preparation method and application thereof

Abstract

The embodiment of the invention provides a metal organic material, the structural formula of which is as shown in the formula (I): # imgabs0 #, in the formula (I), X1, X2, X7, X8, X9 and X10 are respectively and independently CH or N, and X3, X4, X5 and X6 are respectively and independently CH, C or N; each R1, R2, R3, R4, R5, R6 independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, or the like; each R7 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, or the like; z1 and Z2 are respectively connected with X3 and X4, or X4 and X5, or X5 and X6, one of Z1 and Z2 is a single bond, and the other is oxygen, sulfur, selenium or a divalent atomic group. The metal organic material can be applied to the organic electroluminescent device as a luminescent material, and the luminescent color purity, the device efficiency and the device stability of the organic electroluminescent device are improved.

Description

Technical Field

[0001] The embodiments of the present application relate to the technical field of luminescent materials, and in particular to a metal organic material and a preparation method and application thereof. Background Art

[0002] Organic light-emitting diodes (OLEDs) are energy conversion devices that use organic light-emitting materials to convert applied electrical energy into light energy. They have the characteristics of high brightness, fast response, wide viewing angle, and flexibility, and are widely used in display, lighting and other fields. In the field of organic light-emitting materials, phosphorescent materials can fully utilize the energy of singlet and triplet excitons in the light-emitting process, and theoretically their quantum efficiency can reach 100%, so both the industry and academia pay more attention to them. At present, phosphorescent materials are mainly organic complexes of some heavy metals such as iridium, platinum (II), europium, and osmium. Among them, organic electroluminescent devices based on existing platinum (II) organic complexes usually have a large half-peak width, resulting in insufficient purity of the luminescent color; and the efficiency and stability of the device still need to be improved. Summary of the invention

[0003] In view of this, an embodiment of the present application provides a metal organic material, which is a platinum (II) organic complex. When applied to an organic electroluminescent device as a luminescent material, the luminescent color purity, as well as the device efficiency and stability of the organic electroluminescent device based on the platinum (II) organic complex can be improved to a certain extent.

[0004] In a first aspect, an embodiment of the present application provides a metal organic material, wherein the structural formula of the metal organic material is shown in formula (I):

[0005]

[0006] In formula (I), X1, X2, X7, X8, X9, X 10 Each is independently CH or N, X3, X4, X5, and X6 are each independently CH, C, or N; Ring A is a nitrogen heterocycle, Ring B, Ring C, and Ring D are each independently a benzene ring or a nitrogen heterocycle, and Ring E, Ring F, and Ring G are benzene rings;

[0007] n1 is 4, n2 is 2, n3 is 2, n4 is 4, n5 is 3, n6 is 4, and n7 is 4; each of R1, R2, R3, R4, R5, and R6 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group (-OH), a thiol group (-SH), a nitro group (-NO2), a cyano group (-CN), an isocyano group (-NC), a carboxyl group (-COOH), an amide group (-CONH2), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted any one of alkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted amino (-NH2), substituted or unsubstituted alkylthio (-SR), substituted or unsubstituted arylthio (-SAr), substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone (-SO2R), substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl (-COR), substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, and substituted or unsubstituted silanyl;

[0008] Each R7 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group (-OH), a thiol group (-SH), a nitro group (-NO2), a cyano group (-CN), an isocyano group (-NC), a carboxyl group (-COOH), an amide group (-CONH2), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group , substituted or unsubstituted heteroaryloxy, substituted or unsubstituted amino (-NH2), substituted or unsubstituted alkylthio (-SR), substituted or unsubstituted arylthio (-SAr), substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone (-SO2R), substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl (-COR), substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, substituted or unsubstituted silane; two or more adjacent R1, R2, R3, R4, R5, R6, R7 may form a ring structure or a condensed structure;

[0009] Z1 and Z2 are connected to X3 and X4, or X4 and X5, or X5 and X6 respectively, and one of Z1 and Z2 is a single bond, and the other is oxygen, sulfur, selenium or a divalent atomic group.

[0010] The metal organic material provided in the embodiment of the present application can be applied to an organic electroluminescent device as a luminescent material, so as to improve the luminescent color purity of the organic electroluminescent device based on platinum (II) organic complex to a certain extent, as well as the device efficiency and stability. The metal organic material of the present application is a tetradentate platinum (II) complex formed by metal platinum and a tetradentate ligand with a special structure. In the tetradentate platinum (II) complex, the metal platinum and the tetradentate ligand have a strong chelating effect, and the tetradentate platinum (II) complex has good stability, so that the light-emitting device can obtain a higher stability; the tetradentate ligand has a special structure, and the tetradentate platinum (II) complex formed with metal platinum is a planar structure with strong rigidity, which is conducive to obtaining a narrow emission spectrum and a higher luminous efficiency; the ring structure composed of Z1 and Z2 and ring D is introduced on the ring C of the tetradentate ligand, which is conducive to reducing the molecular luminescence spectrum shoulder peak ratio of the metal organic material and improving the luminescence spectrum color purity of the device.

[0011] In the embodiment of the present application, the substituted or unsubstituted alkyl is a substituted or unsubstituted C1-C60 alkyl, the substituted or unsubstituted cycloalkyl is a substituted or unsubstituted C3-C60 cycloalkyl, the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C1-C60 heterocycloalkyl, the substituted or unsubstituted alkenyl is a substituted or unsubstituted C2-C60 alkenyl, the substituted or unsubstituted cycloalkenyl is a substituted or unsubstituted C3-C60 cycloalkenyl, the substituted or unsubstituted heterocycloalkenyl is a substituted or unsubstituted C2- C60 heterocycloalkenyl, the substituted or unsubstituted alkynyl is a substituted or unsubstituted C2-C60 alkynyl, the substituted or unsubstituted cycloalkynyl is a substituted or unsubstituted C3-C60 cycloalkynyl, the substituted or unsubstituted heterocycloalkynyl is a substituted or unsubstituted C2-C60 heterocycloalkynyl, the substituted or unsubstituted aryl is a substituted or unsubstituted C6-C60 aryl, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C2-C60 heteroaryl, the substituted or unsubstituted alkoxy is a substituted or unsubstituted C1-C6 The substituted or unsubstituted aryloxy group is a substituted or unsubstituted C6-C60 aryloxy group, the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C2-C60 heteroaryloxy group, the substituted amino group is a substituted amino group of C1-C60, the substituted or unsubstituted alkylthio group is a substituted or unsubstituted C1-C60 alkylthio group, the substituted or unsubstituted arylthio group is a substituted or unsubstituted C6-C60 arylthio group, the substituted or unsubstituted heteroarylthio group is a substituted or unsubstituted C2-C60 heteroarylthio group, and the The substituted or unsubstituted alkylsulfone group is a substituted or unsubstituted C1-C60 alkylsulfone group, the substituted or unsubstituted arylsulfone group is a substituted or unsubstituted C6-C60 arylsulfone group, the substituted or unsubstituted alkylcarbonyl group is a substituted or unsubstituted C1-C60 alkylcarbonyl group, the substituted or unsubstituted arylcarbonyl group is a substituted or unsubstituted C6-C60 arylcarbonyl group, the substituted boryl group is a boryl group substituted with a C1-C60 substituent group, and the substituted silyl group is a silyl group substituted with a C1-C60 substituent group.

[0012] In the embodiment of the present application, the substituted or unsubstituted alkyl is a substituted or unsubstituted C1-C20 alkyl, the substituted or unsubstituted cycloalkyl is a substituted or unsubstituted C3-C20 cycloalkyl, the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C1-C20 heterocycloalkyl, the substituted or unsubstituted alkenyl is a substituted or unsubstituted C2-C20 alkenyl, the substituted or unsubstituted cycloalkenyl is a substituted or unsubstituted C3-C20 cycloalkenyl, the substituted or unsubstituted heterocycloalkenyl is a substituted or unsubstituted C2- C20 heterocycloalkenyl, the substituted or unsubstituted alkynyl is a substituted or unsubstituted C2-C20 alkynyl, the substituted or unsubstituted cycloalkynyl is a substituted or unsubstituted C3-C20 cycloalkynyl, the substituted or unsubstituted heterocycloalkynyl is a substituted or unsubstituted C2-C20 heterocycloalkynyl, the substituted or unsubstituted aryl is a substituted or unsubstituted C6-C30 aryl, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C2-C30 heteroaryl, the substituted or unsubstituted alkoxy is a substituted or unsubstituted C1-C2 the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C6-C30 aryloxy group, the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C2-C30 heteroaryloxy group, the substituted amino group is a C1-C20 substituted amino group, the substituted or unsubstituted alkylthio group is a substituted or unsubstituted C1-C20 alkylthio group, the substituted or unsubstituted arylthio group is a substituted or unsubstituted C6-C30 arylthio group, the substituted or unsubstituted heteroarylthio group is a substituted or unsubstituted C2-C30 heteroarylthio group, the The substituted or unsubstituted alkylsulfone group is a substituted or unsubstituted C1-C20 alkylsulfone group, the substituted or unsubstituted arylsulfone group is a substituted or unsubstituted C6-C30 arylsulfone group, the substituted or unsubstituted alkylcarbonyl group is a substituted or unsubstituted C1-C20 alkylcarbonyl group, the substituted or unsubstituted arylcarbonyl group is a substituted or unsubstituted C6-C30 arylcarbonyl group, the substituted boryl group is a boryl group substituted with a C1-C20 substituent group, and the substituted silyl group is a silyl group substituted with a C1-C20 substituent group. The suitable number of carbon atoms can make the overall molecular structure of the metal organic material simpler, the preparation raw materials are more easily available, and it is beneficial to the preparation of the metal organic material.

[0013] In the embodiment of the present application, the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted aryl, substituted heteroaryl, substituted alkoxy, substituted aryloxy, substituted heteroaryloxy, substituted amino, substituted alkylthio, substituted arylthio, substituted heteroarylthio, substituted alkylsulfone, substituted arylsulfone, substituted alkylcarbonyl, substituted borane, substituted The substituent groups in the silyl group are selected from one or more of deuterium atoms, tritium atoms, halogen atoms, hydroxyl groups, thiol groups, nitro groups, cyano groups, isocyano groups, carboxyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted borane groups, and substituted or unsubstituted silyl groups. The introduction of substituent groups can not only obtain more abundant metal organic material types, but also can achieve fine-tuning of metal organic material performance to better meet different application requirements.

[0014] In the implementation manner of the present application, Z1 and Z2 are connected to X3 and X4 respectively, and X3 and X4 are both C;

[0015] Or Z1 and Z2 are connected to X4 and X5 respectively, and both X4 and X5 are C;

[0016] Or Z1 and Z2 are connected to X5 and X6 respectively, and X5 and X6 are both C. One of Z1 and Z2 is a single bond, so Z1 and Z2 are connected to X3 and X4, or X4 and X5, or X5 and X6 respectively, and form a five-membered ring structure with the carbon atom of ring D. The introduction of the cyclic structure formed by the five-membered ring structure and ring D into the tetradentate ligand is conducive to reducing the shoulder peak ratio of the molecular luminescence spectrum of the metal organic material and improving the color purity of the luminescence spectrum of the device.

[0017] In the embodiment of the present application, the ring C and the ring D are benzene rings, and the ring B is a benzene ring or a nitrogen heterocycle. The ring C and the ring D are benzene rings, and the ring B is a benzene ring or a nitrogen heterocycle. The raw materials are easily available, and metal organic materials with excellent performance can be obtained.

[0018] In some embodiments of the present application, the ring B is a nitrogen heterocycle, X1 is CH, and X2 is N.

[0019] A second aspect of the embodiment of the present application provides a method for preparing the metal organic material according to the first aspect, comprising:

[0020] reacting raw material a with raw material b in the presence of a divalent palladium catalyst, a coupling reaction ligand, a base and a first solvent to obtain an intermediate c;

[0021]

[0022] Adding intermediate c and ammonium hexafluorophosphate into a second solvent to react and obtain ligand d;

[0023]

[0024] The ligand d is added into platinum salt, sodium acetate and a third solvent to react and obtain the metal organic material.

[0025] The preparation method of the metal organic material provided in the embodiment of the present application has a simple preparation process and is easy to realize industrial production.

[0026] The third aspect of the embodiments of the present application provides the use of the metal organic material described in the first aspect in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, light-emitting electrochemical cells, photoelectric converters, light-opening devices, image sensors, lasers, photosensitive devices, biological imaging equipment, biological monitoring equipment, coatings, and organic laser equipment. The metal organic material of the embodiment of the present application has good luminescent properties, and its application as a luminescent material in the above-mentioned scenes can improve the performance of various devices, equipment, and materials.

[0027] The fourth aspect of the embodiment of the present application provides a light-emitting layer, wherein the light-emitting layer comprises the metal organic material according to the first aspect of the embodiment of the present application. The metal organic material of the embodiment of the present application has good light-emitting performance and can improve the light-emitting performance of the light-emitting layer.

[0028] In the embodiment of the present application, the light-emitting layer includes a host material and a doping material, and the doping material includes the metal organic material, that is, the metal organic material of the embodiment of the present application is used as a guest material to form a light-emitting layer together with the host material. The metal organic material of the embodiment of the present application can be used as a doping material to better coordinate with the host material to improve the light-emitting performance of the light-emitting layer.

[0029] The fifth aspect of the present application provides an electronic device, which includes the metal organic material described in the first aspect of the present application; or includes the light emitting layer described in the third aspect of the present application. The metal organic material of the present application has good light emitting performance and can improve device performance.

[0030] In the embodiment of the present application, the electronic device includes a cathode and an anode, and a functional layer located between the cathode and the anode, and the functional layer includes the metal organic material. Specifically, the functional layer may include the light emitting layer.

[0031] In the embodiment of the present application, the electronic device may include an electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device or a light-emitting electrochemical cell.

[0032] The sixth aspect of the embodiment of the present application provides a display device, the display device includes the electronic device described in the fourth aspect of the embodiment of the present application; or includes the light-emitting layer described in the third aspect of the embodiment of the present application. The metal organic material of the embodiment of the present application has good light-emitting properties, which is conducive to improving the display effect of the display device.

[0033] The embodiment of the present application also provides an electronic device, the electronic device comprising the display device described in the fifth aspect of the embodiment of the present application; or comprising the electronic device described in the fourth aspect of the embodiment of the present application. The metal organic material of the embodiment of the present application has good luminescent properties, which is conducive to improving the display effect of the electronic device and improving the market competitiveness of the electronic device.

[0034] The embodiment of the present application also provides a lighting device, which includes the electronic device described in the fourth aspect of the embodiment of the present application; or includes the light-emitting layer described in the third aspect of the embodiment of the present application. The metal organic material of the embodiment of the present application has good light-emitting performance, which is conducive to improving the light-emitting effect of the lighting device and improving the market competitiveness of the lighting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 A schematic diagram of the structure of an organic electroluminescent device 100 provided in an embodiment of the present application;

[0036] Figure 2 A schematic diagram of the structure of a display device 200 provided in an embodiment of the present application;

[0037] Figure 3 A schematic diagram of the structure of an electronic device 300 provided in an embodiment of the present application;

[0038] Figure 4 The theoretically calculated frontier orbital distribution diagram of the metal organic materials Pt32-Pt51 of the embodiment of the present application;

[0039] Figure 5 The results of theoretical calculation of excited states of the metal organic material Pt1 of the present embodiment and the comparative material are shown. DETAILED DESCRIPTION

[0040] The embodiments of the present application will be described below in conjunction with the drawings in the embodiments of the present application.

[0041] The present application provides a metal organic material, the structural formula of the metal organic material is shown in formula (I):

[0042]

[0043] In formula (I), X1, X2, X3, X4, X5, X6, X7, X8, X9, X10 Each is independently CH or N; Ring A is a nitrogen heterocycle, Ring B, Ring C, and Ring D are each independently a benzene ring or a nitrogen heterocycle, and Ring E, Ring F, and Ring G are benzene rings;

[0044] n1 is 4, n2 is 2, n3 is 2, n4 is 4, n5 is 3, n6 is 4, and n7 is 4; each of R1, R2, R3, R4, R5, and R6 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group (-OH), a thiol group (-SH), a nitro group (-NO2), a cyano group (-CN), an isocyano group (-NC), a carboxyl group (-COOH), an amide group (-CONH2), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted any one of alkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted amino (-NH2), substituted or unsubstituted alkylthio (-SR), substituted or unsubstituted arylthio (-SAr), substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone (-SO2R), substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl (-COR), substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, and substituted or unsubstituted silanyl;

[0045] Each R7 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group (-OH), a thiol group (-SH), a nitro group (-NO2), a cyano group (-CN), an isocyano group (-NC), a carboxyl group (-COOH), an amide group (-CONH2), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group , substituted or unsubstituted heteroaryloxy, substituted or unsubstituted amino (-NH2), substituted or unsubstituted alkylthio (-SR), substituted or unsubstituted arylthio (-SAr), substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone (-SO2R), substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl (-COR), substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, substituted or unsubstituted silane; two or more adjacent R1, R2, R3, R4, R5, R6, R7 may form a ring structure or a condensed structure;

[0046] Z1 and Z2 are connected to X3 and X4, or X4 and X5, or X5 and X6 respectively, and one of Z1 and Z2 is a single bond, and the other is oxygen, sulfur, selenium or a divalent atomic group.

[0047] The metal organic material provided in the embodiment of the present application can be applied to an organic electroluminescent device as a luminescent material, so as to improve the luminescent color purity of the organic electroluminescent device based on platinum (II) organic complex to a certain extent, as well as device efficiency and stability. The metal organic material of the present application is a tetradentate platinum (II) complex formed by a metal platinum and a tetradentate ligand with a special structure, in which the metal platinum and the tetradentate ligand have a strong chelating effect, and the tetradentate platinum (II) complex has good stability, so that the light-emitting device can obtain a higher stability; the tetradentate ligand has a special structure, and the tetradentate platinum (II) complex formed with the metal platinum is a planar structure, with strong rigidity, which is conducive to obtaining a narrow emission spectrum and a higher luminous efficiency; the ring structure composed of Z1 and Z2 and ring D is introduced on the ring C of the tetradentate ligand, which is conducive to reducing the molecular luminescence spectrum shoulder ratio (i.e., shoulder height divided by main peak height) of the metal organic material, and improving the luminescence spectrum color purity of the device.

[0048] In some embodiments of the present application, the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted aryl, substituted heteroaryl, substituted alkoxy, substituted aryloxy, substituted heteroaryloxy, substituted amino, substituted alkylthio, substituted arylthio, substituted heteroarylthio, substituted alkylsulfone, substituted arylsulfone, substituted alkylcarbonyl, substituted borane, substituted The substituent group in the silyl group is selected from one or more of a deuterium atom, a tritium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, an isocyano group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted borane group, and a substituted or unsubstituted silyl group. The introduction of the substituent group can not only obtain a richer variety of metal organic materials, but also realize the fine-tuning of the performance of metal organic materials to better meet different application requirements.

[0049] In the embodiment of the present application, the halogen atom may be F, Cl, Br or I.

[0050] In some embodiments of the present application, the substituted or unsubstituted alkyl group may be a substituted or unsubstituted C1-C60 alkyl group, or a substituted or unsubstituted C1-C20 alkyl group, and specifically, for example, may be a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkyl group. For example, the substituted or unsubstituted C1 alkyl group is a substituted or unsubstituted methyl group, the substituted or unsubstituted C2 alkyl group is a substituted or unsubstituted ethyl group, the substituted or unsubstituted C3 alkyl group is a substituted or unsubstituted n-propyl group or isopropyl group, the substituted or unsubstituted C4 alkyl group is a substituted or unsubstituted n-butyl group, isobutyl group or tert-butyl group, and other substituted or unsubstituted alkyl groups are deduced by analogy. In some embodiments of the present application, the substituted alkyl group may be a deuterated alkyl group, a halogenated alkyl group, or an aryl alkyl group. The deuterated alkyl group may be, for example, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, or a deuterated tert-butyl group; the halogenated alkyl group may be a fluoroalkyl group, for example, a trifluoromethyl group, a trifluoroethyl group, or the like; the aryl alkyl group may be, for example, a benzyl group, a phenethyl group, or the like.

[0051] In some embodiments of the present application, the substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C3-C60 cycloalkyl group, or a substituted or unsubstituted C3-C20 cycloalkyl group, and specifically may be a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 cycloalkyl group. For example, the substituted or unsubstituted C3 cycloalkyl group may be a substituted or unsubstituted cyclopropyl group, the substituted or unsubstituted C5 cycloalkyl group may be a substituted or unsubstituted cyclopentyl group, the substituted or unsubstituted C6 alkyl group may be a substituted or unsubstituted cyclohexyl group, and other substituted or unsubstituted cycloalkyl groups may be deduced by analogy. The substituted cycloalkyl group may be, for example, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, etc.

[0052] In some embodiments of the present application, the substituted or unsubstituted heterocycloalkyl may be a substituted or unsubstituted C1-C60 heterocycloalkyl, or a substituted or unsubstituted C1-C20 heterocycloalkyl, specifically, for example, a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 heterocycloalkyl. The heteroatoms in the heterocycloalkyl may be one or more of oxygen, nitrogen, and sulfur. The substituted or unsubstituted heterocycloalkyl may be a substituted or unsubstituted nitrogen heterocycloalkyl, an oxygen heterocycloalkyl, or a sulfur heterocycloalkyl.

[0053] In some embodiments of the present application, the substituted or unsubstituted alkenyl group may be a substituted or unsubstituted C2-C60 alkenyl group, or a substituted or unsubstituted C2-C20 alkenyl group, and specifically, for example, may be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkenyl group. For example, the substituted or unsubstituted C2 alkenyl group is a substituted or unsubstituted vinyl group, the substituted or unsubstituted C3 alkenyl group is a substituted or unsubstituted propenyl group, and the other substituted or unsubstituted alkenyl groups are deduced by analogy.

[0054] In some embodiments of the present application, the substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C3-C60 cycloalkenyl group, or a substituted or unsubstituted C3-C20 cycloalkenyl group, and specifically, for example, may be a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 cycloalkenyl group. For example, the substituted or unsubstituted C3 cycloalkenyl group is a substituted or unsubstituted cyclopropenyl group.

[0055] In some embodiments of the present application, substituted or unsubstituted heterocycloalkenyl can be substituted or unsubstituted C2-C60 heterocycloalkenyl, or substituted or unsubstituted C2-C20 heterocycloalkenyl, specifically for example, substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 heterocycloalkenyl. The heteroatom in the heterocycloalkenyl can be one or more of oxygen, nitrogen, and sulfur. Substituted or unsubstituted heterocycloalkenyl can be substituted or unsubstituted nitrogen heterocycloalkenyl, oxygen heterocycloalkenyl, or sulfur heterocycloalkenyl.

[0056] In some embodiments of the present application, the substituted or unsubstituted alkynyl group may be a substituted or unsubstituted C2-C60 alkynyl group, or a substituted or unsubstituted C2-C20 alkynyl group, and specifically, for example, may be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkynyl group. For example, the substituted or unsubstituted C2 alkynyl group is a substituted or unsubstituted ethynyl group, the substituted or unsubstituted C3 alkynyl group is a substituted or unsubstituted propynyl group, and the same applies to other substituted or unsubstituted alkynyl groups.

[0057] In some embodiments of the present application, the substituted or unsubstituted cycloalkynyl group may be a substituted or unsubstituted C3-C60 cycloalkynyl group, or a substituted or unsubstituted C3-C20 cycloalkynyl group, for example, it may be a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 cycloalkynyl group.

[0058] In some embodiments of the present application, the substituted or unsubstituted heterocycloalkynyl group can be a substituted or unsubstituted C2-C60 heterocycloalkynyl group, or a substituted or unsubstituted C2-C20 heterocycloalkynyl group, specifically for example, a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 heterocycloalkynyl group. The heteroatom in the heterocycloalkynyl group can be one or more of oxygen, nitrogen, and sulfur. The substituted or unsubstituted heterocycloalkynyl group can be a substituted or unsubstituted azacycloalkynyl group, an oxygen-heterocycloalkynyl group, or a thio-heterocycloalkynyl group.

[0059] In some embodiments of the present application, the substituted or unsubstituted aryl group may be a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C6-C30 aryl group, and specifically, for example, may be a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 aryl group. The substituted or unsubstituted aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the polycyclic aryl group may be a condensed ring type or a non-condensed ring type (such as biphenyls). Illustratively, the substituted or unsubstituted aryl group is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted binaphthylfluorenyl. In some embodiments of the present application, the substituted aryl group may be a deuterated aryl group, an alkyl aryl group, an alkylsilyl aryl group, and the deuterated aryl group may be, for example, a deuterated phenyl group, a deuterated biphenyl group, or a deuterated naphthyl group; the alkyl aryl group may be a substituted or unsubstituted methyl group, an ethyl group, an isopropyl group, or a tert-butyl group, and specifically may be a methyl substituted phenyl group, an ethyl substituted phenyl group, an isopropyl substituted phenyl group, a tert-butyl substituted phenyl group, a deuterated methyl substituted phenyl group, a deuterated ethyl substituted phenyl group, a deuterated isopropyl substituted phenyl group, a deuterated tert-butyl substituted phenyl group, a deuterated biphenyl group, Methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted naphthyl, deuterated ethyl-substituted naphthyl, deuterated isopropyl-substituted naphthyl, deuterated tert-butyl-substituted naphthyl, etc.; the alkylsilylaryl group can be, for example, trimethylsilyl-substituted phenyl.

[0060] In some embodiments of the present application, the substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; specifically, for example, it may be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 heteroaryl group. The substituted or unsubstituted heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroatoms in the heteroaryl group may include one or more of oxygen, nitrogen, and sulfur. Exemplarily, the substituted or unsubstituted heteroaryl includes a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzopyrrolyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted triazine, a substituted or unsubstituted xanthone. The substituted heteroaryl may be a deuterated heteroaryl, an alkyl heteroaryl, an alkylsilyl heteroaryl. The substituted heteroaryl group may be, for example, a substituted or unsubstituted methyl group, ethyl group, isopropyl group, or tert-butyl group, and specifically may be a methyl-substituted heteroaryl group (e.g., a methyl-substituted pyridyl group), an ethyl-substituted heteroaryl group, an isopropyl-substituted heteroaryl group, a tert-butyl-substituted heteroaryl group, a deuterated methyl-substituted heteroaryl group, a deuterated ethyl-substituted heteroaryl group, a deuterated isopropyl-substituted heteroaryl group, or a deuterated tert-butyl-substituted heteroaryl group.

[0061] In some embodiments of the present application, the substituted or unsubstituted alkoxy group is a substituted or unsubstituted C1-C60 alkoxy group, or a substituted or unsubstituted C1-C20 alkoxy group. Specifically, for example, it can be a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkoxy group. Exemplarily, the substituted or unsubstituted C1 alkoxy group is a substituted or unsubstituted methoxy group, the substituted or unsubstituted C2 alkoxy group is a substituted or unsubstituted ethoxy group, and the other substituted or unsubstituted alkoxy groups are deduced by analogy.

[0062] In some embodiments of the present application, the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C6-C60 aryloxy group, or a substituted or unsubstituted C6-C30 aryloxy group. Specifically, for example, it can be a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 aryloxy group. The aryloxy group is an oxy group substituted by an aryl group. Exemplarily, the substituted or unsubstituted aryloxy group is a phenoxy group, a methylphenyloxy group, or an isopropylmethylphenyloxy group.

[0063] In some embodiments of the present application, the substituted or unsubstituted heteroaryloxy is a substituted or unsubstituted C2-C60 heteroaryloxy, or a substituted or unsubstituted C2-C30 heteroaryloxy. Specifically, for example, it can be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 heteroaryloxy. The heteroatom in the heteroaryl can be one or more of oxygen, nitrogen, and sulfur. The heteroaryloxy is an oxy group substituted by a heteroaryl. Illustratively, the substituted or unsubstituted heteroaryloxy group is furan-2-yloxy, furan-3-yloxy, thien-2-yloxy, thien-3-yloxy, 1H-pyrrol-2-yloxy, 1H-pyrrol-3-yloxy, and the like.

[0064] In some embodiments of the present application, the substituted amino group may be a C1-C60 substituted amino group or a C1-C20 substituted amino group. Specifically, for example, the amino group may be substituted by C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or C20. The substituted amino group may be a monosubstituted amino group or a disubstituted amino group. For example, the substituted amino group may be an alkylamino group, an arylamino group, a hydroxyamino group, or the like.

[0065] In some embodiments of the present application, the substituted or unsubstituted alkylthio group is a substituted or unsubstituted C1-C60 alkylthio group, or a substituted or unsubstituted C1-C20 alkylthio group. Alkylthio groups are sulfenyl groups substituted by alkyl groups, similar to alkoxy groups. Specifically, for example, substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkylthio groups. Exemplarily, substituted or unsubstituted C1 alkylthio groups are substituted or unsubstituted methylthio groups (CH3-S-), substituted or unsubstituted C2 alkylthio groups are substituted or unsubstituted ethylthio groups, and other substituted or unsubstituted alkylthio groups are deduced by analogy.

[0066] In some embodiments of the present application, the substituted or unsubstituted arylthio group is a substituted or unsubstituted C6-C60 arylthio group, or a substituted or unsubstituted C6-C30 arylthio group. Specifically, for example, it can be a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 arylthio group. An arylthio group is a thio group substituted by an aryl group.

[0067] In some embodiments of the present application, the substituted or unsubstituted heteroarylthio group is a substituted or unsubstituted C2-C60 heteroarylthio group, or a substituted or unsubstituted C2-C30 heteroarylthio group. Specifically, for example, it can be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 heteroarylthio group. The heteroatom in the heteroaryl group can be one or more of oxygen, nitrogen, and sulfur. The heteroarylthio group is a thio group substituted by a heteroaryl group.

[0068] In some embodiments of the present application, the substituted or unsubstituted alkyl sulfone group may be a substituted or unsubstituted C1-C60 alkyl sulfone group, or a substituted or unsubstituted C1-C20 alkyl sulfone group, specifically, for example, a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkyl sulfone group. The substituted or unsubstituted alkyl sulfone group may be represented by -SO2R, where R represents a substituted or unsubstituted alkyl group. For example, the alkyl sulfone group is a methyl sulfone group or an ethyl sulfone group.

[0069] In some embodiments of the present application, the substituted or unsubstituted aryl sulfone group can be a C6-C60 aryl sulfone group, or a substituted or unsubstituted C6-C30 aryl sulfone group, specifically, for example, a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 aryl sulfone group. The substituted or unsubstituted aryl sulfone group can be represented by -SO2Ar, Ar represents a substituted or unsubstituted aryl group. Exemplarily, the aryl sulfone group is a phenyl sulfone group.

[0070] In some embodiments of the present application, the substituted or unsubstituted alkylcarbonyl group may be a substituted or unsubstituted C1-C60 alkylcarbonyl group, or a substituted or unsubstituted C1-C20 alkylcarbonyl group, and specifically, for example, may be a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkylcarbonyl group. The substituted or unsubstituted alkylcarbonyl group may be represented by -SO2R, where R represents a substituted or unsubstituted alkyl group. For example, the alkylcarbonyl group is a methylcarbonyl group or an ethylcarbonyl group.

[0071] In some embodiments of the present application, the substituted or unsubstituted arylcarbonyl group may be a C6-C60 arylcarbonyl group, or a substituted or unsubstituted C6-C30 arylcarbonyl group, specifically, for example, a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 arylcarbonyl group. The substituted or unsubstituted arylcarbonyl group may be represented by -SO2Ar, where Ar represents a substituted or unsubstituted aryl group. For example, the arylcarbonyl group is a phenylcarbonyl group.

[0072] In some embodiments of the present application, the substituted or unsubstituted silyl group is a silyl group substituted with a C1-C60 substituent group, or a silyl group substituted with a C1-C20 substituent group, and specifically, for example, it can be a silyl group substituted with a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 substituent group. The substituted silyl group can be a substituted or unsubstituted alkyl-substituted silyl group, i.e., a substituted or unsubstituted alkylsilyl group; or a substituted or unsubstituted aryl-substituted silyl group, i.e., a substituted or unsubstituted arylsilyl group. Exemplarily, the alkylsilyl group is a trimethylsilyl group, a triethylsilyl group, and the arylsilyl group is a triphenylsilyl group.

[0073] In some embodiments of the present application, the substituted or unsubstituted boryl group is a boryl group substituted with a C1-C60 substituent group, or a boryl group substituted with a C1-C20 substituent group, and specifically, for example, it can be a boryl group substituted with a C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 substituent group. The substituted boryl group can be a substituted or unsubstituted alkyl substituted boryl group, i.e., a substituted or unsubstituted alkyl boryl group; or a substituted or unsubstituted aryl substituted boryl group, i.e., a substituted or unsubstituted aryl boryl group. For example, the alkyl boryl group is a trimethyl boryl group, a triethyl boryl group, and the aryl boryl group is a triphenyl boryl group.

[0074] Controlling the above-mentioned groups to a suitable number of carbon atoms can make the overall molecular structure of the metal organic material simpler, and the raw materials for preparation are more easily available, which is beneficial to the preparation of the metal organic material.

[0075] In some embodiments of the present application, in formula (I), Z1 and Z2 are connected to X3 and X4 respectively, X3 and X4 are both C, and one of Z1 and Z2 is a single bond. In this case, the molecular structure of the metal organic material is as shown in formula (I-1) or (I-2):

[0076]

[0077] In some embodiments of the present application, in formula (I), Z1 and Z2 are connected to X4 and X5 respectively, X4 and X5 are both C, and one of Z1 and Z2 is a single bond. In this case, the molecular structure of the metal organic material is as shown in formula (I-3) or (I-4):

[0078]

[0079] In some embodiments of the present application, in formula (I), Z1 and Z2 are connected to X5 and X6 respectively, X5 and X6 are both C, and one of Z1 and Z2 is a single bond. In this case, the molecular structure of the metal organic material is as shown in formula (I-5) or (I-6):

[0080]

[0081] In the embodiment of the present application, one of Z1 and Z2 is a single bond, therefore, Z1 and Z2 are connected to X3 and X4, or X4 and X5, or X5 and X6, respectively, and form a five-membered ring structure with the carbon atom of ring D. The introduction of the cyclic structure formed by the five-membered ring structure and ring D into the tetradentate ligand is conducive to reducing the proportion of shoulder peaks in the molecular luminescence spectrum of metal organic materials and improving the color purity of the luminescence spectrum of the device.

[0082] In some embodiments of the present application, ring C and ring D are benzene rings, and ring B is a benzene ring or a nitrogen heterocycle. Ring C and ring D are benzene rings, and ring B is a benzene ring or a nitrogen heterocycle. The raw materials are easily available, and metal organic materials with excellent performance can be obtained.

[0083] In some embodiments of the present application, ring B is a nitrogen heterocycle, X1 is CH, and X2 is N.

[0084] In the embodiment of the present application, the metal organic material may have, but is not limited to, the following structure:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The present application also provides a method for preparing the metal organic material, comprising:

[0171] S101, reacting raw material a with raw material b in the presence of a divalent palladium catalyst, a coupling reaction ligand, a base and a first solvent to obtain an intermediate c;

[0172]

[0173] S102, adding the intermediate c and ammonium hexafluorophosphate into a second solvent to react to obtain a ligand d;

[0174]

[0175] S103, adding ligand d to platinum salt, sodium acetate and a third solvent to react to obtain the above metal organic material.

[0176] It can be understood that the letter codes in the raw material a, raw material b, intermediate c and ligand d have the same meanings as the corresponding letter codes in formula (I), which will not be repeated here.

[0177] In step S101, the divalent palladium catalyst may be but is not limited to Tris(dibenzylideneacetone)dipalladium , the coupling reaction ligand can be but is not limited to 2-(Di-tert-butylphosphino)biphenyl, The base may be sodium tert-butoxide or potassium tert-butoxide, and the first solvent may be toluene, xylene, or the like.

[0178] In step S102, the second solvent may be, but is not limited to, triethyl orthoformate.

[0179] In step S103, the platinum salt may be, but is not limited to, (1,5-cyclooctadiene) platinum dichloride, and the third solvent may be, but is not limited to, diethylene glycol dimethyl ether.

[0180] The preparation method of the metal organic material provided in the embodiment of the present application has a simple preparation process and is easy to realize industrial production.

[0181] The above-mentioned metal organic material provided in the embodiment of the present application is a phosphorescent material, which can emit blue light, has a narrow half-width, a low shoulder peak ratio, and good stability. It can be used in various electronic devices with light-emitting, display, lighting and other functions to improve the device's light color purity, light-emitting efficiency and stability. The metal organic material of the embodiment of the present application can be obtained through a relatively simple synthesis path, is suitable for industrial production, and has good application effects and industrialization prospects in the field of OLED lighting or OLED display.

[0182] The embodiments of the present application provide the application of the above-mentioned metal organic materials in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, light-emitting electrochemical cells, photoelectric converters, light-opening devices, image sensors, lasers, photosensitive devices, bio-imaging equipment, bio-monitoring equipment, coatings, and organic laser equipment. Specifically, the above-mentioned metal organic materials can be used as luminescent materials in the above-mentioned devices. For example, the above-mentioned metal organic materials provided in the embodiments of the present application can be applied to organic electroluminescent devices and can be used as materials for the light-emitting layer of organic electroluminescent devices. Specifically, the metal organic materials in the embodiments of the present application have narrow half-width and high quantum yield, and can be used as doping materials for the light-emitting layer of organic electroluminescent devices to improve the color purity and efficiency of the device.

[0183] The present application embodiment provides an electronic device, which includes the metal organic material described in the present application embodiment. The electronic device may be, for example, an organic electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device, a light-emitting electrochemical cell, etc. Figure 1 , Figure 1 A schematic diagram of the structure of an organic light-emitting diode (OLED) 100 provided in one embodiment of the present application. Figure 1 The organic electroluminescent device 100 shown includes an anode 10, a cathode 20, and a functional layer 30 located between the anode 10 and the cathode 20. The functional layer 30 includes a light-emitting layer 301. The light-emitting layer 301 includes the above-mentioned metal organic material provided in the embodiment of the present application.

[0184] In some embodiments of the present application, the light-emitting layer 301 contains a host material and a doping material (also referred to as a "guest material"), wherein the doping material includes at least one of the metal organic materials mentioned above in the present application. In the embodiments of the present application, the doping material of the light-emitting layer 301 may include only one or more of the metal organic materials mentioned above in the present application; or may include one or more of the metal organic materials mentioned above in the present application and other doping materials at the same time. The other doping materials may be various doping materials available in the art, which may be selected according to actual needs.

[0185] In the embodiment of the present application, the main material of the light-emitting layer 301 may include one or more main materials, and the main material may be various main materials available in the art, and may be selected according to actual needs.

[0186] In the embodiment of the present application, the constituent materials of the anode 10 and the cathode 20 are conductive materials, which can be independently selected from conductive metals, conductive metal oxides, conductive polymers, etc. Among them, the conductive metal can include one or more of metal elements such as magnesium (Mg), aluminum (Al), gold (Au), silver (Ag), platinum (Pt), target (Pd) and their alloys; the conductive metal oxide includes but is not limited to one or more of indium tin oxide (ITO), indium zinc oxide (IZO), aluminum-doped zinc oxide (AZO), fluorine-doped tin dioxide (FTO), phosphorus-doped tin dioxide (PTO), etc.; the conductive polymer includes but is not limited to polythiophene, polypyrrole, polyaniline, etc.

[0187] In the implementation mode of this application, see Figure 1 , the functional layer 30 further includes a first carrier transport layer 302 located between the anode 10 and the light-emitting layer 301, and a second carrier transport layer 303 located between the cathode 20 and the light-emitting layer 301. The first carrier transport layer 302 may be one or more of a hole injection layer 3021, a hole transport layer 3022, and an electron blocking layer 3023 located between the anode 10 and the light-emitting layer 301. The hole injection layer 3021 is located between the anode 10 and the hole transport layer 3022, and the electron blocking layer 3023 is located between the light-emitting layer 301 and the hole transport layer 3022. The second carrier transport layer 303 may be one or more of an electron injection layer 3031, an electron transport layer 3032, and a hole blocking layer 3033 located between the cathode 20 and the light-emitting layer 301. The electron injection layer 3031 is located between the cathode 20 and the electron transport layer 3032, and the hole blocking layer 3033 is located between the cathode 20 and the hole transport layer 3022. In some embodiments, Figure 1As shown, the organic electroluminescent device 100 includes an anode 10, a hole injection layer 3021, a hole transport layer 3022, an electron blocking layer 3023, a light-emitting layer 301, a hole blocking layer 3033, an electron transport layer 3032, and an electron injection layer 3031, which are arranged in sequence. It should be noted that not all layers of the functional layer 30 are necessary, but the light-emitting layer 301 is necessary. For example, the functional layer 30 may also include, in the direction from the anode 10 to the cathode 20, a stacked structure of "light-emitting layer 301 / electron transport layer 3032", or a stacked structure of "light-emitting layer 301 / electron injection layer 3031", or a stacked structure of "hole injection layer 3021 / light-emitting layer 301 / electron transport layer 3032", or a stacked structure of "hole injection layer 3021 / light-emitting layer 301 / electron injection layer 3031", or a stacked structure of "hole transport layer 3022 / light-emitting layer 301 / electron transport layer 3032", or a stacked structure of " The stacked structure includes "hole injection layer 3021 / hole transport layer 3022 / light-emitting layer 301 / electron transport layer 3032", or the stacked structure includes "hole injection layer 3021 / hole transport layer 3022 or electron blocking layer 3023 / light-emitting layer 301 / hole blocking layer 3033 or electron transport layer 3032 / electron injection layer 3031", or the stacked structure includes "hole injection layer 3021 / hole transport layer 3022 / electron blocking layer 3023 / light-emitting layer 301 / hole blocking layer 3033 or electron transport layer 3032 / electron injection layer 3031", etc. Wherein " / " indicates the boundary between each layer. In the present application, there is no specific limitation on the thickness of the above layers, and those skilled in the art can determine it according to actual needs. The materials of the above layers are conventionally selected in the field and are not specifically limited in the present application.

[0188] In some embodiments, the organic electroluminescent device 100 may further include a substrate 40 (eg Figure 1 The substrate 40 may be located on the side of the anode 10 away from the functional layer 30 (eg Figure 1 As shown), in this case, the organic electroluminescent device 100 is a bottom-emitting device. The substrate 40 may also be located on the side of the cathode 20 away from the functional layer 30. In this case, the organic electroluminescent device 100 is a top-emitting device, and the top-emitting device includes a cathode 20, a functional layer 30 and an anode 10 sequentially arranged on the substrate 40. The substrate 40 can serve as a supporting portion for the entire organic electroluminescent device 100, and its material may be quartz, glass, elemental silicon, metal, plastic, etc. In some embodiments, the substrate 40 is glass or plastic that is transparent to light. The shape of the substrate 40 may be determined according to the specific application scenario, for example, it may be formed into a plate, a film, or a sheet. The thickness of the substrate 40 is not particularly limited.

[0189] In the present application, there is no particular limitation on the preparation process of the anode 10, cathode 20 and each layer of the functional layer 30, and they can be prepared by physical vapor deposition, chemical vapor deposition or coating. Among them, the physical vapor deposition method can include one or more of vacuum evaporation (such as resistance evaporation source evaporation method, electron beam evaporation source evaporation method, pulsed laser deposition method, etc.), sputtering method (such as magnetron sputtering method), etc.; the coating method can include solution spin coating, dip coating, scraper coating, spray coating, roller coating, inkjet printing, screen printing and other methods. Generally, the anode 10 and the cathode 20 can be prepared by vacuum evaporation, and each layer of the functional layer 30 can be prepared by vacuum evaporation or coating. Figure 1 Taking the preparation of the organic electroluminescent device shown as an example, the anode 10 may be first formed on the substrate 40, and then the functional layer 30 including the light-emitting layer 301 may be sequentially formed on the anode 10, and then the cathode 20 may be formed on the functional layer 30. In other embodiments of the present application, the cathode 20 and the functional layer 30 including the light-emitting layer 301 may be sequentially formed on the substrate 40, and then the anode 10 may be formed on the functional layer 30.

[0190] See also Figure 2 The embodiment of the present application further provides a display device 200 , which includes the electronic device described above in the embodiment of the present application, and specifically may include the organic electroluminescent device 100 described above.

[0191] In the embodiment of the present application, the display device 200 can be an OLED panel, a mobile phone, a tablet computer, a laptop computer, a wearable device (such as a smart watch, a smart bracelet, etc.), a television, a digital camera, a camcorder, a player, a micro-display device (such as smart glasses, virtual reality (VR) devices, augmented reality (AR) devices), a telephone, a printer, a vehicle, a household appliance, a billboard, an information board, a car central control screen, and any other product or component with a display function. A visual display device.

[0192] The embodiment of the present application also provides a lighting device, including the electronic device described above in the embodiment of the present application, specifically, the organic electroluminescent device 100 described above. The lighting device may include automobile taillights, automobile headlights, automobile fog lights, indoor lighting devices (including commercial or household lighting devices, such as table lamps, ceiling lamps, etc.), outdoor lighting devices (such as street lamps), backlight sources of liquid crystal display devices, etc. using organic electroluminescent devices.

[0193] See also Figure 3The embodiment of the present application further provides an electronic device 300, and the electronic device 300 includes the display device 200 described above in the embodiment of the present application. The electronic device 300 can be a mobile phone, a tablet computer, a laptop computer, a wearable device (such as a smart watch, a smart bracelet, etc.), a vehicle display device, a television, a digital camera, a camcorder, a player, a micro display device (such as smart glasses, virtual reality (VR) devices, augmented reality (AR) devices, telephones, printers, vehicles, household appliances, billboards, information boards, car central control screens, and any other electronic products with display functions.

[0194] The embodiments of the present application are further described below with reference to a plurality of embodiments.

[0195] Example 1: The synthesis route of the tetradentate metal platinum (II) complex Pt1 is as follows:

[0196]

[0197] (1) Synthesis of intermediate 1-NH: 1-NH2 (628 mg, 2.12 mmol, 1.1 equivalent), 1-Cl (1.0 g, 1.93 mmol, 1.0 equivalent), tris(dibenzylideneacetone)dipalladium (55 mg, 0.06 mmol, 0.03 equivalent), 2-(di-tert-butylphosphino)biphenyl (36 mg, 0.12 mmol, 0.06 equivalent), sodium tert-butoxide (371 mg, 3.86 mmol, 2.0 equivalent) were added to a dry three-necked flask equipped with a magnetic rotor. The nitrogen atmosphere was replaced three times. Toluene (20 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 85° C. for 11 hours, cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 30 / 1-10 / 1, to obtain the product 1-NH, 1.31 g of off-white foamy solid, yield 88%, which was directly used for the next reaction.

[0198] (2) Synthesis of ligand L1: 1-NH (1.31 g, 1.68 mmol, 1.0 equivalent) and ammonium hexafluorophosphonate (548 mg, 3.36 mmol, 2.0 equivalent) were added to a sealed tube with a magnetic rotor and dried, and nitrogen was replaced three times. Triethyl orthoformate (6 mL) was added under nitrogen protection, and the mixture was stirred in an oil bath at 80°C for 1.5 hours, cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: dichloromethane-dichloromethane / ethyl acetate = 30 / 1, to obtain product L1, 1.52 g of light red foamy solid, yield 97%. 1H NMR (400MHz, DMSO-d6): δ (ppm) 1.32 (s, 9H), 1.36 (s, 18H), 7.36 (dd, J = 8.4, 2.0Hz, 1H), 7.44 -7.49(m,1H),7.49-7.58(m,4H),7.65(d,J=1.6Hz,2H),7.67(t,J=2.4Hz,1H),7.68-7.74(m ,2H),7.76-7.82(m,5H),7.83-7.88(m,1H),7.90(t,J=3.2Hz,1H),7.95(m,1H),8.19(d,J=2 .0Hz, 1H), 8.21 (d, J = 3.6Hz, 1H), 8.50 (d, J = 8.4Hz, 1H), 8.65 (d, J = 5.2Hz, 1H), 10.52 (s, 1H).

[0199] (3) Synthesis of Pt1: L1 (500 mg, 0.53 mmol, 1.0 equivalent), (1,5-cyclooctadiene) platinum dichloride (208 mg, 0.55 mmol, 1.0 equivalent) and sodium acetate (131 mg, 1.59 mmol, 3.0 equivalent) were added to a sealed tube with a magnetic rotor and dried. The nitrogen was replaced three times. Diethylene glycol dimethyl ether (32 mL) was added under nitrogen protection. After bubbling nitrogen for 1 hour, the sealed tube was wrapped with tin foil to avoid light. The mixture was stirred in an oil bath at 120°C for 3 days, cooled to room temperature, added with deionized water and stirred for 5-10 minutes to quench, added with dichloromethane for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 4 / 1-2 / 1, to obtain the product Pt1, a yellow solid 220 mg, yield 42%. 1H NMR (400MHz, DMSO-d6): δ (ppm) 0.89-1.74 (m, 27H), 5.90-6.17 (m, 2H), 7.04 (d, J = 8.0Hz, 1H), 7.12-7.23 (m, 1H), 7.41 (s, 1H), 7. 43-7.86(m,10H),7.89(d,J=8.0Hz,1H),8.14(d,J=8.0Hz,1H),8.17-8.25(m,2H),8.46(d,J=7.6Hz,1H),8.76(d,J=6.0Hz,1H).

[0200] Example 2: The synthesis route of the tetradentate metal platinum (II) complex Pt2 is as follows:

[0201]

[0202] (1) Synthesis of intermediate 2-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 2-NH was prepared as an off-white foamy solid (632 mg) with a yield of 85%, which was directly used in the next step.

[0203] (2) Synthesis of ligand L2: Referring to the synthesis method of L1 in Example 1, 2-Cl was used instead of 1-Cl in Example 1 to prepare 710 mg of a light red foamy solid with a yield of 80%. MS: m / z 787.41 (M+H)+.

[0204] (3) Synthesis of Pt2: Referring to the synthesis method of Pt1 in Example 1, ligand L2 was used instead of L1 in Example 1 to prepare 123 mg of yellow solid with a yield of 32%. MS: m / z 980.36 (M+H)+.

[0205] Example 3: The synthesis route of the tetradentate metal platinum (II) complex Pt3 is as follows:

[0206]

[0207] (1) Synthesis of intermediate 3-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 3-NH was prepared as an off-white foamy solid (875 mg) with a yield of 82%, which was directly used in the next step.

[0208] (2) Synthesis of ligand L3: Referring to the synthesis method of L1 in Example 1, 3-Cl was used instead of 1-Cl in Example 1 to prepare 965 mg of a light red foamy solid with a yield of 86%. MS: m / z 787.41 (M+H)+.

[0209] (3) Synthesis of Pt3: Referring to the synthesis method of Pt1 in Example 1, ligand L3 was used to replace L1 in Example 1 to obtain 241 mg of yellow solid with a yield of 35%. MS: m / z 980.36 (M+H)+.

[0210] Example 4: The synthesis route of the tetradentate metal platinum (II) complex Pt4 is as follows:

[0211]

[0212] (1) Synthesis of intermediate 4-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 4-NH was prepared as an off-white foamy solid (576 mg) with a yield of 83%, which was directly used in the next step.

[0213] (2) Synthesis of ligand L4: Referring to the synthesis method of L1 in Example 1, 4-Cl was used instead of 1-Cl in Example 1 to prepare 480 mg of a light red foamy solid with a yield of 75%. MS: m / z 787.42 (M+H)+.

[0214] (3) Synthesis of Pt4: Referring to the synthesis method of Pt1 in Example 1, ligand L4 was used instead of L1 in Example 1 to prepare 105 mg of yellow solid with a yield of 25%. MS: m / z 980.34 (M+H)+.

[0215] Example 5: The synthesis route of the tetradentate metal platinum (II) complex Pt5 is as follows:

[0216]

[0217] (1) Synthesis of intermediate 5-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 5-NH was prepared as an off-white foamy solid (752 mg) with a yield of 80%, which was directly used in the next step.

[0218] (2) Synthesis of ligand L5: Referring to the synthesis method of L1 in Example 1, 5-Cl was used instead of 1-Cl in Example 1 to prepare 736 mg of a light red foamy solid with a yield of 82%. MS: m / z 787.41 (M+H)+.

[0219] (3) Synthesis of Pt5: Referring to the synthesis method of Pt1 in Example 1, ligand L5 was used to replace L1 in Example 1 to obtain 251 mg of yellow solid with a yield of 36%. MS: m / z 980.37 (M+H)+.

[0220] Example 6: The synthesis route of the tetradentate metal platinum (II) complex Pt6 is as follows:

[0221]

[0222] (1) Synthesis of intermediate 6-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 6-NH was prepared as an off-white foamy solid (476 mg) with a yield of 86%, which was directly used in the next step.

[0223] (2) Synthesis of ligand L6: Referring to the synthesis method of L1 in Example 1, 6-Cl was used instead of 1-Cl in Example 1 to prepare 449 mg of a light red foamy solid with a yield of 81%. MS: m / z 787.42 (M+H)+.

[0224] (3) Synthesis of Pt6: Referring to the synthesis method of Pt1 in Example 1, ligand L6 was used to replace L1 in Example 1 to obtain 120 mg of yellow solid with a yield of 30%. MS: m / z 980.37 (M+H)+.

[0225] Example 7: The synthesis route of the tetradentate metal platinum (II) complex Pt7 is as follows:

[0226]

[0227] (1) Synthesis of ligand L7: Referring to the synthesis method of L1 in Example 1, 7-Cl was used instead of 1-Cl in Example 1 to prepare 520 mg of yellow foamy solid, 72%. MS: m / z 948.56 (M+H)+.

[0228] (2) Synthesis of Pt7: Referring to the synthesis method of Pt1 in Example 1, ligand L7 was used to replace L1 in Example 1 to obtain 65 mg of yellow solid, 29%. MS: m / z 1140.48 (M+H)+.

[0229] Example 8: The synthesis route of the tetradentate metal platinum (II) complex Pt8 is as follows:

[0230]

[0231]

[0232] (1) Synthesis of ligand L8: Referring to the synthesis method of L1 in Example 1, 8-Cl was used instead of 1-Cl in Example 1 to prepare 710 mg of yellow foamy solid, 80%. MS: m / z 948.57 (M+H)+.

[0233] (2) Synthesis of Pt8: Referring to the synthesis method of Pt1 in Example 1, ligand L8 was used to replace L1 in Example 1 to obtain 123 mg of yellow solid, 32%. MS: m / z 1140.46 (M+H)+.

[0234] Example 9: The synthesis route of the tetradentate metal platinum (II) complex Pt9 is as follows:

[0235]

[0236] (1) Synthesis of ligand L9: Referring to the synthesis method of L1 in Example 1, 9-Cl was used instead of 1-Cl in Example 1 to prepare 965 mg of yellow foamy solid, 86%. MS: m / z 948.52 (M+H)+.

[0237] (2) Synthesis of Pt9: Referring to the synthesis method of Pt1 in Example 1, ligand L9 was used to replace L1 in Example 1 to obtain 241 mg of yellow solid, 35%. MS: m / z 1140.45 (M+H)+.

[0238] Example 10: The synthesis route of the tetradentate metal platinum (II) complex Pt10 is as follows:

[0239]

[0240] (1) Synthesis of ligand L10: Referring to the synthesis method of L1 in Example 1, 10-Cl was used instead of 1-Cl in Example 1 to prepare 480 mg of yellow foamy solid, 75%. MS: m / z 948.53 (M+H)+.

[0241] (2) Synthesis of Pt10: Referring to the synthesis method of Pt1 in Example 1, ligand L10 was used instead of L1 in Example 1 to prepare 105 mg of yellow solid, 25%. MS: m / z 1140.48 (M+H)+.

[0242] Example 11: The synthesis route of the tetradentate metal platinum (II) complex Pt11 is as follows:

[0243]

[0244] (1) Synthesis of ligand L11: Referring to the synthesis method of L1 in Example 1, 11-Cl was used instead of 1-Cl in Example 1 to prepare 736 mg of yellow foamy solid, 82%. MS: m / z 948.56 (M+H)+.

[0245] (2) Synthesis of Pt11: Referring to the synthesis method of Pt1 in Example 1, ligand L11 was used to replace L1 in Example 1 to obtain 251 mg of yellow solid, 36%. MS: m / z 1140.47 (M+H)+.

[0246] Example 12: The synthesis route of the tetradentate metal platinum (II) complex Pt12 is as follows:

[0247]

[0248] (1) Synthesis of ligand L12: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 12-Cl to obtain 449 mg of a yellow foamy solid, 81%. MS: m / z 948.55 (M+H)+.

[0249] (2) Synthesis of Pt12: Referring to the synthesis method of Pt1 in Example 1, ligand L12 was used to replace L1 in Example 1 to obtain 120 mg of yellow solid, 30%. MS: m / z 1140.46 (M+H)+.

[0250] Example 13: The synthesis route of the tetradentate metal platinum (II) complex Pt13 is as follows:

[0251]

[0252] (1) Synthesis of ligand L13: Referring to the synthesis method of L1 in Example 1, 13-Cl was used instead of 1-Cl in Example 1 to prepare 530 mg of yellow foamy solid, 71%. MS: m / z 789.41 (M+H)+.

[0253] (2) Synthesis of Pt13: Referring to the synthesis method of Pt1 in Example 1, ligand L13 was used to replace L1 in Example 1 to obtain 82 mg of yellow solid, 25%. MS: m / z 981.36 (M+H)+.

[0254] Example 14: The synthesis route of the tetradentate metal platinum (II) complex Pt14 is as follows:

[0255]

[0256] (1) Synthesis of ligand L14: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 14-Cl to obtain 670 mg of a yellow foamy solid, 78%. MS: m / z 789.42 (M+H)+.

[0257] (2) Synthesis of Pt14: Referring to the synthesis method of Pt1 in Example 1, ligand L14 was used instead of L1 in Example 1 to prepare 102 mg of yellow solid, 25%. MS: m / z 981.37 (M+H)+.

[0258] Example 15: The synthesis route of the tetradentate metal platinum (II) complex Pt15 is as follows:

[0259]

[0260]

[0261] (1) Synthesis of ligand L15: Referring to the synthesis method of L1 in Example 1, 15-Cl was used instead of 1-Cl in Example 1 to prepare 600 mg of yellow foamy solid, 85%. MS: m / z 789.45 (M+H)+.

[0262] (2) Synthesis of Pt15: Referring to the synthesis method of Pt1 in Example 1, ligand L15 was used to replace L1 in Example 1 to obtain 112 mg of yellow solid, 27%. MS: m / z 981.34 (M+H)+.

[0263] Example 16: The synthesis route of the tetradentate metal platinum (II) complex Pt16 is as follows:

[0264]

[0265] (1) Synthesis of ligand L16: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 16-Cl to obtain 702 mg of a yellow foamy solid, 86%. MS: m / z 789.43 (M+H)+.

[0266] (2) Synthesis of Pt16: Referring to the synthesis method of Pt1 in Example 1, ligand L16 was used to replace L1 in Example 1 to obtain 175 mg of yellow solid, 29%. MS: m / z 981.35 (M+H)+.

[0267] Example 17: The synthesis route of the tetradentate metal platinum (II) complex Pt17 is as follows:

[0268]

[0269] (1) Synthesis of ligand L17: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 17-Cl to obtain 902 mg of a yellow foamy solid, 86%. MS: m / z 789.45 (M+H)+.

[0270] (2) Synthesis of Pt17: Referring to the synthesis method of Pt1 in Example 1, ligand L17 was used to replace L1 in Example 1 to obtain 182 mg of yellow solid, 30%. MS: m / z 981.37 (M+H)+.

[0271] Example 18: The synthesis route of the tetradentate metal platinum (II) complex Pt18 is as follows:

[0272]

[0273] (1) Synthesis of ligand L18: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 18-Cl to obtain 735 mg of a yellow foamy solid, 75%. MS: m / z 789.45 (M+H)+.

[0274] (2) Synthesis of Pt18: Referring to the synthesis method of Pt1 in Example 1, ligand L18 was used to replace L1 in Example 1 to obtain 102 mg of yellow solid, 25%. MS: m / z 981.37 (M+H)+.

[0275] Example 19: The synthesis route of the tetradentate metal platinum (II) complex Pt19 is as follows:

[0276]

[0277] (1) Synthesis of ligand L19: Referring to the synthesis method of L1 in Example 1, 1-Cl in Example 1 was replaced with 19-Cl to obtain 582 mg of yellow foamy solid, 76%. MS: m / z 1038.59 (M+H)+.

[0278] (2) Synthesis of Pt19: Referring to the synthesis method of Pt1 in Example 1, ligand L19 was used to replace L1 in Example 1 to obtain 102 mg of yellow solid, 31%. MS: m / z 1230.53 (M+H)+.

[0279] Example 20: The synthesis route of the tetradentate metal platinum (II) complex Pt20 is as follows:

[0280]

[0281]

[0282] (1) Synthesis of ligand L20: Referring to the synthesis method of L1 in Example 1, 20-Cl was used instead of 1-Cl in Example 1 to prepare 676 mg of yellow foamy solid, 81%. MS: m / z 1038.58 (M+H)+.

[0283] (2) Synthesis of Pt20: Referring to the synthesis method of Pt1 in Example 1, ligand L20 was used instead of L1 in Example 1 to prepare 135 mg of yellow solid, 32%. MS: m / z 1230.52 (M+H)+.

[0284] Example 21: The synthesis route of the tetradentate metal platinum (II) complex Pt21 is as follows:

[0285]

[0286] (1) Synthesis of ligand L21: Referring to the synthesis method of L1 in Example 1, 21-Cl was used instead of 1-Cl in Example 1 to prepare 705 mg of yellow foamy solid, 76%. MS: m / z 1038.56 (M+H)+.

[0287] (2) Synthesis of Pt21: Referring to the synthesis method of Pt1 in Example 1, ligand L21 was used instead of L1 in Example 1 to prepare 142 mg of yellow solid, 28%. MS: m / z 1230.54 (M+H)+.

[0288] Example 22: The synthesis route of the tetradentate metal platinum (II) complex Pt22 is as follows:

[0289]

[0290]

[0291] (1) Synthesis of ligand L22: Referring to the synthesis method of L1 in Example 1, 22-Cl was used instead of 1-Cl in Example 1 to prepare 786 mg of yellow foamy solid, 80%. MS: m / z 1038.58 (M+H)+.

[0292] (2) Synthesis of Pt22: Referring to the synthesis method of Pt1 in Example 1, ligand L22 was used to replace L1 in Example 1 to obtain 106 mg of yellow solid, 37%. MS: m / z 1230.57 (M+H)+.

[0293] Example 23: The synthesis route of the tetradentate metal platinum (II) complex Pt23 is as follows:

[0294]

[0295] (1) Synthesis of ligand L23: Referring to the synthesis method of L1 in Example 1, 23-Cl was used instead of 1-Cl in Example 1 to prepare 605 mg of yellow foamy solid, 75%. MS: m / z 1038.56 (M+H)+.

[0296] (2) Synthesis of Pt23: Referring to the synthesis method of Pt1 in Example 1, ligand L23 was used to replace L1 in Example 1 to obtain 152 mg of yellow solid, 30%. MS: m / z 1230.56 (M+H)+.

[0297] Example 24: The synthesis route of the tetradentate metal platinum (II) complex Pt24 is as follows:

[0298]

[0299]

[0300] (1) Synthesis of ligand L24: Referring to the synthesis method of L1 in Example 1, 24-Cl was used instead of 1-Cl in Example 1 to prepare 768 mg of yellow foamy solid, 79%. MS: m / z 1038.57 (M+H)+.

[0301] (2) Synthesis of Pt24: Referring to the synthesis method of Pt1 in Example 1, ligand L24 was used instead of L1 in Example 1 to prepare 141 mg of yellow solid, 30%. MS: m / z 1230.54 (M+H)+.

[0302] Example 25: The synthesis route of the tetradentate metal platinum (II) complex Pt25 is as follows:

[0303]

[0304] (1) Synthesis of 25-NH: 2-NH2 (322 mg, 1.0 mmol, 1.2 equivalents), 1-Cl (517 mg, 1.0 mmol, 1.0 equivalents), tris(dibenzylideneacetone)dipalladium (27 mg, 0.03 mmol, 0.03 equivalents), 2-(di-tert-butylphosphino)biphenyl (18 mg, 0.06 mmol, 0.06 equivalents), sodium tert-butoxide (192 mg, 2.0 mmol, 2.0 equivalents) were added to a sealed tube with a magnetic rotor and dried. The nitrogen was replaced three times, and toluene (5 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100° C. for 12 hours, cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate = 30:1, to obtain the product 1-NH, a light green foamy solid 616 mg, yield 82%.

[0305] (2) Synthesis of L25: 2-NH (324 mg, 0.43 mmol, 1.0 equivalent) and ammonium hexafluorophosphonate (141 mg, 0.86 mmol, 2.0 equivalent) were added to a sealed tube with a magnetic rotor and dried. The nitrogen was replaced three times. Triethyl orthoformate (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 80°C for 1 hour, cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: dichloromethane, to obtain the product L1, a light green foamy solid 232 mg, with a yield of 71%. 1H NMR(500MHz,DMSO-d6)δ1.01(d,J=6.5Hz,6H),1.12(d,J=7.0Hz,6H),1.34(s,9H),2.3 0–2.37(m,2H),7.39(dd,J=8.5,2.5Hz,1H),7.47(t,J=7.5Hz,1H),7.49–7.55(m,2H), 7.54–7.59(m,4H),7.70–7.76(m,2H),7.77–7.83(m,5H),8.02(d,J=8.5Hz,1H),8.19– 8.21(m,1H),8.21(s,1H),8.52(d,J=8.5Hz,1H),8.66(d,J=5.0Hz,1H),10.63(s,1H).

[0306] (3) Synthesis of Pt25: L1 (204 mg, 0.27 mmol, 1.0 equivalent), (1,5-cyclooctadiene) platinum dichloride (100 mg, 0.27 mmol, 1.0 equivalent) and sodium acetate (66 mg, 0.81 mmol, 3.0 equivalent) were added to a sealed tube with a magnetic rotor and dried. The nitrogen was replaced three times. Diethylene glycol dimethyl ether (16 mL) was added under nitrogen protection. After bubbling nitrogen for 30 minutes, the sealed tube was wrapped with tin foil to avoid light. The mixture was stirred in an oil bath at 120°C for 3 days, cooled to room temperature, added with deionized water and stirred for 5-10 minutes to quench, and extracted with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / dichloromethane = 2:1, and the product Pt1 was obtained as a yellow solid of 82 mg, with a yield of 32%. 1H NMR (500MHz, CDCl3-d6) δ1.28(s,9H),1.57(s,12H),2.73–3.37(m,2H),6.10(dd,J=6.5,2.0Hz,1H),6.95(d,J=8 .5Hz,1H),7.22(dd,J=0.5,1.0Hz,1H),7.25–7.26(m,2H),7.27(d,J=7.5Hz,1H),7.35–7.49(m,5H),7.54(d,J=8. 5Hz,1H),7.66(dd,J=8.0,1.0Hz,1H),7.74(d,J=7.5Hz,1H),7.77(d,J=8.5Hz,1H),7.92(d,J=8.5Hz,1H),8.00( dd,J=8.0,1.0Hz,1H),8.05(d,J=2.0Hz,1H),8.19(d,J=8.5Hz,1H),8.23(d,J=8.5Hz,1H),8.66(d,J=6.0Hz,1H).

[0307] Example 26: The synthesis route of the tetradentate metal platinum (II) complex Pt26 is as follows:

[0308]

[0309] (1) Synthesis of intermediate 26-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 26-NH was prepared as an off-white foamy solid (233 mg) with a yield of 85%, which was directly used in the next step.

[0310] (2) Synthesis of ligand L26: Referring to the synthesis method of L1 in Example 1, 2-Cl was used instead of 1-Cl in Example 1 to prepare 345 mg of light red foamy solid with a yield of 75%. It was directly used in the next reaction. MS: m / z 759.37 (M+H)+.

[0311] (3) Synthesis of Pt26: Referring to the synthesis method of Pt1 in Example 1, ligand L26 was used instead of L1 in Example 1 to prepare 28 mg of yellow solid with a yield of 30%. MS: m / z 952.32 (M+H)+.

[0312] Example 27: The synthesis route of the tetradentate metal platinum (II) complex Pt27 is as follows:

[0313]

[0314] (1) Synthesis of intermediate 27-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 27-NH was prepared as an off-white foamy solid (357 mg) with a yield of 86%, which was directly used in the next step.

[0315] (2) Synthesis of ligand L27: Referring to the synthesis method of L1 in Example 1, 3-Cl was used instead of 1-Cl in Example 1 to prepare 736 mg of a light red foamy solid with a yield of 75%. MS: m / z 759.38 (M+H)+.

[0316] (3) Synthesis of Pt27: Referring to the synthesis method of Pt1 in Example 1, ligand L27 was used instead of L1 in Example 1 to prepare 265 mg of yellow solid with a yield of 27%. MS: m / z 952.35 (M+H)+.

[0317] Example 28: The synthesis route of the tetradentate metal platinum (II) complex Pt28 is as follows:

[0318]

[0319] (1) Synthesis of intermediate 28-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 28-NH was prepared as an off-white foamy solid (267 mg) with a yield of 79%, which was directly used in the next step.

[0320] (2) Synthesis of ligand L28: Referring to the synthesis method of L1 in Example 1, 4-Cl was used instead of 1-Cl in Example 1 to prepare 577 mg of a light red foamy solid with a yield of 69%. MS: m / z 759.36 (M+H)+.

[0321] (3) Synthesis of Pt28: Referring to the synthesis method of Pt1 in Example 1, ligand L28 was used instead of L1 in Example 1 to prepare 409 mg of yellow solid with a yield of 39%. MS: m / z 952.33 (M+H)+.

[0322] Example 29: The synthesis route of the tetradentate metal platinum (II) complex Pt29 is as follows:

[0323]

[0324] (1) Synthesis of intermediate 29-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 29-NH was prepared as an off-white foamy solid (397 mg) with a yield of 85%, which was directly used in the next step.

[0325] (2) Synthesis of ligand L29: Referring to the synthesis method of L1 in Example 1, 5-Cl was used instead of 1-Cl in Example 1 to prepare 697 mg of a light red foamy solid with a yield of 79%. MS: m / z 759.37 (M+H)+.

[0326] (3) Synthesis of Pt29: Referring to the synthesis method of Pt1 in Example 1, ligand L29 was used instead of L1 in Example 1 to prepare 58 mg of yellow solid with a yield of 37%. MS: m / z 952.30 (M+H)+.

[0327] Example 30: The synthesis route of the tetradentate metal platinum (II) complex Pt30 is as follows:

[0328]

[0329]

[0330] (1) Synthesis of intermediate 30-NH: Referring to the synthesis method of intermediate 1-NH in Example 1, the target product 30-NH was prepared as an off-white foamy solid (365 mg) with a yield of 84%, which was directly used in the next step.

[0331] (2) Synthesis of ligand L30: Referring to the synthesis method of L1 in Example 1, 6-Cl was used instead of 1-Cl in Example 1 to prepare 475 mg of a light red foamy solid with a yield of 73%. MS: m / z 759.35 (M+H)+.

[0332] (3) Synthesis of Pt30: Referring to the synthesis method of Pt1 in Example 1, ligand L30 was used instead of L1 in Example 1 to prepare 84 mg of yellow solid with a yield of 31%. MS: m / z 952.33 (M+H)+.

[0333] Example 31: The synthesis route of the tetradentate metal platinum (II) complex Pt31 is as follows:

[0334]

[0335] (1) Synthesis of intermediate (31-NH): 2-NH2 (400 mg, 0.7 mmol, 1.0 equivalent), 31-Cl (400 mg, 0.7 mmol, 1.0 equivalent), trisdibenzylideneacetone dipalladium (20 mg, 0.02 mmol, 3 mol%), 2-(di-tert-butylphosphino)biphenyl (12 mg, 0.04 mmol, 6 mol%) and sodium tert-butoxide (134 mg, 1.4 mmol, 2.0 equivalent) were added to a reaction flask, and toluene (5 mL) was added. The reaction was stopped in an oil bath at 85°C for 3 hours, cooled to room temperature, and the organic phase was separated, concentrated, and subjected to silica gel column chromatography to obtain 517 mg of a white solid with a yield of 90%. The structure was characterized and used directly in the next step.

[0336] (2) Synthesis of ligand (L31): 31-NH (517 mg, 0.64 mmol, 1.0 equivalent), ammonium hexafluorophosphate (208 mg, 1.28 mmol, 2.0 equivalent), and triethyl orthoformate (5 mL) were added to the reaction flask. The reaction was stopped at 80°C for 2 hours, cooled to room temperature, and the organic phase was separated and concentrated. 624 mg of white solid was obtained by silica gel column chromatography with a yield of 87%. 1H NMR (500 MHz, DMSO) δ1.00 (d, J = 6.5 Hz, 6H), 1.11 (d, J = 6.5 Hz, 6H), 1.31 (s, 9H), 1.36 (s, 9H), 2.29–2.33 (m, 2H), 7.38 (dd, J = 8.0, 2.0 Hz, 1H), 7.46 (t, J = 6.0 Hz, 1H), 7.51–7.5 7(m,8H),7.69–7.74(m,3H),7.76–7.79(m,3H),7.87(d,J=8.0Hz,1H),7.96(d,J=8.5H z,1H),8.19–8.21(m,2H),8.50(d,J=8.5Hz,1H),8.63(d,J=5.5Hz,1H),10.64(s,1H).

[0337] (3) Synthesis of Pt31: Add L31 (444 mg, 0.46 mmol, 1.0 equivalent), (1,5-cyclooctadiene) platinum (II) dichloride (180 mg, 0.48 mmol, 1.05 equivalent) and sodium acetate (113 mg, 1.38 mmol, 3.0 equivalent) to a reaction flask, and add diethylene glycol dimethyl ether (5 mL). React at 120°C for 72 hours, cool to room temperature, separate the organic phase, concentrate, and obtain 345 mg of a light yellow solid by silica gel column chromatography, with a yield of 73%. 1H NMR (500MHz, CDCl3) δ0.59–1.21(m,12H),1.27(s,9H),1.52(s,9H),3.15(s,2H),6.09(dd,J=6.0 ,2.0Hz,1H),6.96(d,J=8.0Hz,1H),7.27–7.30(m,4H),7.37–7.41(m,2H),7.44–7.48(m,2H),7.54 (d,J=8.0Hz,1H),7.70–7.74(m,2H),7.78(d,J=8.5Hz,1H),,7.91(d,J=8.0Hz,1H),8.0(d,J=7.0H z, 1H), 8.04 (d, J = 1.5Hz, 1H), 8.17 (d, J = 8.0Hz, 1H), 8.22 (d, J = 8.0Hz, 1H), 8.66 (d, J = 6.0Hz, 1H).

[0338] The physical properties of the metal organic materials prepared in Examples 1 to 31 of the present application and the existing metal organic materials in Comparative Example 1 were tested, and the results are shown in Table 1. Specifically, the metal organic materials were dissolved in dichloromethane to form a concentration of 10 -5 M solution was tested. The half-peak width is the peak width at half the peak height of the emission spectrum. The shoulder peak height ratio is (shoulder peak height / main peak height)*100%.

[0339] Table 1: Photophysical properties of metal organic materials

[0340]

[0341]

[0342] The structures of the comparative substances in Table 1 are as follows:

[0343]

[0344] From the results in Table 1, it can be seen that the luminescence peaks of the metal organic materials of Examples 1-31 of the present application are in the region of 450nm-470nm, can achieve blue light emission, and have a smaller and narrower half-peak width and a lower shoulder peak ratio.

[0345] Device Embodiment

[0346] Organic electroluminescent devices are prepared using metal organic materials Pt1, Pt5, Pt7, Pt10, Pt13, Pt16, Pt19, Pt25, Pt31, and Ref, respectively.

[0347] Device Example 1

[0348] Taking Pt1 as an example, the device includes a glass substrate, and an ITO anode 10 (15nm), a hole injection layer 3021 (HI-1, with a thickness of 10nm), a hole transport layer 3022 (HT-1, with a thickness of 120nm), an electron blocking layer 3023 (EB-1, with a thickness of 10nm), a light-emitting layer 301 (BH as the main material, Pt1 as the doping material, the mass ratio of BH and Pt1 is 87:13, and the thickness is 25nm), a hole blocking layer 3033 (HB-1, with a thickness of 2nm), an electron transport layer 3032 (ET-1, with a thickness of 35nm), an electron injection layer 3031 (EI-1 layer, with a thickness of 1.5nm) and a cathode 20 (Al, with a thickness of 17nm) stacked in sequence on the glass substrate.

[0349]

[0350] Device Example 2

[0351] The only difference from device embodiment 1 is that Pt1 is replaced by Pt5.

[0352] Device Example 3

[0353] The only difference from device embodiment 1 is that Pt1 is replaced by Pt7.

[0354] Device Example 4

[0355] The only difference from device embodiment 1 is that Pt1 is replaced by Pt10.

[0356] Device Example 5

[0357] The only difference from device embodiment 1 is that Pt1 is replaced by Pt13.

[0358] Device Example 6

[0359] The only difference from device embodiment 1 is that Pt1 is replaced by Pt16.

[0360] Device Example 7

[0361] The only difference from device embodiment 1 is that Pt1 is replaced by Pt19.

[0362] Device Example 8

[0363] The only difference from device embodiment 1 is that Pt1 is replaced by Pt25.

[0364] Device Example 9

[0365] The only difference from device embodiment 1 is that Pt1 is replaced by Pt31.

[0366] Device Comparison

[0367] The only difference from device embodiment 1 is that Pt1 is replaced by the above-mentioned reference material.

[0368] After the OLED light-emitting device is prepared as described above, the anode and cathode are connected using a known driving circuit, and the luminous efficiency CE, BI value, and LT95@1000nits[h] of the device are measured. The test results are shown in Table 2.

[0369] BI is CE / CIEy, CE is the luminous efficiency cd / A, CIEy is the color coordinates CIEy of the light emitted by the light emitting device. LT95@1000nits[h] is the lifespan when the initial brightness is 1000nits and the brightness decays to 95% of the initial brightness.

[0370] Table 2: Luminescence performance of the device

[0371]

[0372] From the results in Table 2, it can be seen that the metal organic materials of the embodiments of the present application are used in the preparation of organic electroluminescent devices to obtain higher luminous efficiency, higher BI value and longer life. The luminous efficiency, BI value and LT95@1000nits[h] of the device prepared by the reference material are all 100% for comparison, and the luminous efficiency, BI value and LT95@1000nits[h] of the device of the embodiments of the present application are greatly improved.

[0373] In addition, the present application also adopts a method similar to that of Examples 1-31 to prepare metal organic materials Pt32-Pt51, and the structural formula of Pt32-Pt51 is:

[0374]

[0375]

[0376] The relevant theoretical calculation experimental data of metal organic materials Pt32-Pt51 are listed in Table 1. The theoretical calculation frontier orbital distribution diagram of metal organic materials Pt32-Pt51 is shown in Table 1. Figure 4 As shown in the figure, the functional and basis set for theoretical calculations are B3lyp / 6-31G*.

[0377] Table 3: Theoretical calculation and experimental data of metal organic material Pt32-Pt51 molecules

[0378]

[0379] Note: The dihedral angle refers to the angle formed between the two terminal heterocyclic rings coordinated to the central metal ion.

[0380] From Table 3 and Figure 4 It can be seen that the metal organic materials Pt32 to Pt51 have large band gaps and can achieve blue light emission.

[0381] Figure 5 Table 4 is the theoretical calculation data of excited states of metal organic material Pt1 and comparison molecules.

[0382] Table 4 Theoretical calculation data of excited states of Pt1 and comparison molecules

[0383] Metal organic material molecules T1[eV] Pt1 2.55 <![CDATA[Ref. [1] ]]> 2.60

[0384] The results in Table 4 show that the luminescent color of Pt1 is comparable to that of the reference Ref.

[0385] It should be understood that the first, second and various numerical numbers involved in this document are only distinguished for the convenience of description and are not used to limit the scope of the present application.

[0386] In this application, "and / or" describes the association relationship of associated objects, indicating that there can be three relationships. For example, A and / or B can mean: A exists alone, A and B exist at the same time, and B exists alone, where A and B can be singular or plural. The character " / " generally indicates that the associated objects are in an "or" relationship.

[0387] In this application, "at least one" means one or more, and "plurality" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, c can be single or multiple, respectively.

[0388] In this application, “-” represents a range value, including the endpoint values ​​at both ends. For example, the value of a can be 0.5-15, which means that the value of a can be between 0.5 and 15, and includes the endpoint values ​​0.5 and 15.

[0389] It should be understood that in the various embodiments of the present application, the size of the serial numbers of the above-mentioned processes does not mean the order of execution, some or all of the steps can be executed in parallel or sequentially, and the execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present application.

Claims

1. A metal organic material, characterized in that: The structural formula of the metal organic material is shown in formula (I): In formula (I), X1, X2, X7, X8, X9, X 10 Each is independently CH or N, X3, X4, X5, and X6 are each independently CH, C, or N; Ring A is a nitrogen heterocycle, Ring B, Ring C, and Ring D are each independently a benzene ring or a nitrogen heterocycle, and Ring E, Ring F, and Ring G are benzene rings; n1 is 4, n2 is 2, n3 is 2, n4 is 4, n5 is 3, n6 is 4, and n7 is 4; each of R1, R2, R3, R4, R5, and R6 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, an isocyano group, a carboxyl group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or any one of unsubstituted heterocycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted amino, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone, substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, and substituted or unsubstituted silanyl; Each R7 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, an isocyano group, a carboxyl group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkynyl group, a substituted or unsubstituted heterocycloalkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted Any one of substituted heteroaryloxy, substituted or unsubstituted amino, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted alkylsulfone, substituted or unsubstituted arylsulfone, substituted or unsubstituted alkylcarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted borane, substituted or unsubstituted silane; two or more adjacent R1, R2, R3, R4, R5, R6, R7 may form a ring structure or a condensed structure; Z1 and Z2 are connected to X3 and X4, or X4 and X5, or X5 and X6 respectively, and one of Z1 and Z2 is a single bond, and the other is oxygen, sulfur, selenium or a divalent atomic group.

2. The metal organic material according to claim 1, characterized in that The substituted or unsubstituted alkyl is a substituted or unsubstituted C1-C60 alkyl, the substituted or unsubstituted cycloalkyl is a substituted or unsubstituted C3-C60 cycloalkyl, the substituted or unsubstituted heterocycloalkyl is a substituted or unsubstituted C1-C60 heterocycloalkyl, the substituted or unsubstituted alkenyl is a substituted or unsubstituted C2-C60 alkenyl, the substituted or unsubstituted cycloalkenyl is a substituted or unsubstituted C3-C60 cycloalkenyl, the substituted or unsubstituted heterocycloalkenyl is a substituted or unsubstituted C2-C60 heterocycloalkenyl. the substituted or unsubstituted alkynyl is a substituted or unsubstituted C2-C60 alkynyl, the substituted or unsubstituted cycloalkynyl is a substituted or unsubstituted C3-C60 cycloalkynyl, the substituted or unsubstituted heterocycloalkynyl is a substituted or unsubstituted C2-C60 heterocycloalkynyl, the substituted or unsubstituted aryl is a substituted or unsubstituted C6-C60 aryl, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C2-C60 heteroaryl, and the substituted or unsubstituted alkoxy is a substituted or unsubstituted C1-C60 alkoxy , the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C6-C60 aryloxy group, the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C2-C60 heteroaryloxy group, the substituted amino group is a C1-C60 substituted amino group, the substituted or unsubstituted alkylthio group is a substituted or unsubstituted C1-C60 alkylthio group, the substituted or unsubstituted arylthio group is a substituted or unsubstituted C6-C60 arylthio group, the substituted or unsubstituted heteroarylthio group is a substituted or unsubstituted C2-C60 heteroarylthio group, the substituted The substituted or unsubstituted alkylsulfone group is a substituted or unsubstituted C1-C60 alkylsulfone group, the substituted or unsubstituted arylsulfone group is a substituted or unsubstituted C6-C60 arylsulfone group, the substituted or unsubstituted alkylcarbonyl group is a substituted or unsubstituted C1-C60 alkylcarbonyl group, the substituted or unsubstituted arylcarbonyl group is a substituted or unsubstituted C6-C60 arylcarbonyl group, the substituted boryl group is a boryl group substituted with a C1-C60 substituent group, and the substituted silyl group is a silyl group substituted with a C1-C60 substituent group.

3. The metal organic material according to any one of claims 1 to 2, characterized in that: The substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted heterocycloalkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted aryl, substituted heteroaryl, substituted alkoxy, substituted aryloxy, substituted heteroaryloxy, substituted amino, substituted alkylthio, substituted arylthio, substituted heteroarylthio, substituted alkylsulfone, substituted arylsulfone, substituted alkylcarbonyl, substituted boryl, substituted silyl The substituent group is selected from one or more of a deuterium atom, a tritium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, an isocyano group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted borane group, and a substituted or unsubstituted silane group.

4. The metal organic material according to any one of claims 1 to 3, characterized in that: Z1 and Z2 are connected to X3 and X4 respectively, and both X3 and X4 are C; Or Z1 and Z2 are connected to X4 and X5 respectively, and both X4 and X5 are C; Alternatively, Z1 and Z2 are connected to X5 and X6 respectively, and both X5 and X6 are C.

5. The metal organic material according to any one of claims 1 to 4, characterized in that: The ring C and the ring D are benzene rings, and the ring B is a benzene ring or a nitrogen heterocycle.

6. The metal organic material according to claim 5, characterized in that The ring B is a nitrogen heterocycle, X1 is CH, and X2 is N.

7. The method for preparing a metal organic material according to any one of claims 1 to 6, characterized in that: include: reacting raw material a with raw material b in the presence of a divalent palladium catalyst, a coupling reaction ligand, a base and a first solvent to obtain an intermediate c; Adding intermediate c and ammonium hexafluorophosphate into a second solvent to react and obtain ligand d; The ligand d is added into platinum salt, sodium acetate and a third solvent to react and obtain the metal organic material.

8. Use of the metal organic material according to any one of claims 1 to 7 in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, light-emitting electrochemical cells, photoelectric converters, switching devices, image sensors, lasers, photosensitive devices, bio-imaging equipment, bio-monitoring equipment, coatings, and organic laser equipment.

9. A light-emitting layer, characterized in that: The light-emitting layer comprises the metal organic material according to any one of claims 1 to 7.

10. The light-emitting layer according to claim 9, characterized in that The light emitting layer includes a host material and a doping material, and the doping material includes the metal organic material.

11. An electronic device, characterized in that: The electronic device comprises the metal organic material according to any one of claims 1 to 7; or comprises the light emitting layer according to any one of claims 9 to 10.

12. The electronic device according to claim 11, characterized in that The electronic device includes a cathode and an anode, and a functional layer located between the cathode and the anode, wherein the functional layer includes the metal organic material.

13. The electronic device according to claim 11 or 12, characterized in that: The electronic device includes an electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device or a light-emitting electrochemical cell.

14. A display device, characterized in that: The display device comprises the electronic device according to any one of claims 11 to 13; or comprises the light-emitting layer according to any one of claims 9 to 10.

15. An electronic device, characterized in that: The electronic device comprises the display device according to claim 14; or comprises the electronic device according to any one of claims 11-13.

16. A lighting device, characterized in that: The lighting device comprises the electronic device according to any one of claims 11 to 13; or comprises the light-emitting layer according to any one of claims 9 to 10.

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