Metal complex and application thereof

Abstract

The invention provides a metal complex and application thereof. The structure of the metal complex is shown as a formula (I), when the metal complex is used in an OLED, especially in a blue light emission area, the metal complex shows enhanced phosphorescence quantum yield, is good in luminescence stability and high in luminescence efficiency, and is suitable for being used as an emitter material in OLED application. According to the metal complex, the organic electroluminescent device with dark blue phosphorescence in electroluminescence and improved luminous efficiency can be obtained, and the thermal stability of the luminescent device is good; the photophysical properties of the metal complex are regulated by regulating the structure of the ligand around the metal center and regulating the structure of the substituent on the ligand, and the metal complex has the advantages of narrow emission spectrum, high stability and high efficiency, and has wide application prospects in the fields of OLED display and illuminating lamps. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex and its application. Background Art

[0002] OLED (organic light-emitting diode) utilizes an organic thin film that emits light when a voltage is applied to the device. OLED is becoming an increasingly concerned technology for applications such as flat panel displays, lighting, and backlighting.

[0003] One application of phosphorescent emission molecules is full-color displays. Industry standards for such displays require pixels suitable for emitting specific colors. Specifically, these standards require saturated red, green, and blue pixels. Currently, red and green phosphorescent materials with a luminous efficiency of 100% are used in various sizes of OLEDs. So far, no blue phosphorescent material has been commercialized, but the luminous efficiency of blue fluorescent materials is only 25%. Although a variety of blue light materials have been widely researched and developed, such as inorganic phosphors, metal complexes, and thermally activated delayed fluorescence materials, etc. However, there are many dissipation pathways for triplet excitons in phosphorescent materials, such as non-radiative transitions, delayed fluorescence, triplet-triplet annihilation, quenching by oxygen and water vapor, etc., which seriously affect the improvement of phosphorescent performance. As people have discovered that crystal engineering can utilize strong intermolecular interactions to effectively inhibit non-radiative transitions of triplet excitons, and because of its dense molecular packing, it can reduce the quenching of triplet excitons by oxygen, water vapor, etc., which is an effective way to achieve high-efficiency room-temperature phosphorescence. However, in the crystal aggregate state, intermolecular π-π stacking easily leads to triplet-triplet annihilation, dissipating a large amount of triplet excitons and affecting the improvement of phosphorescent efficiency; and π-π stacking will increase the intermolecular conjugation degree and cause a red shift in luminescence, making it difficult to achieve blue phosphorescence. How to construct long-lived and high-efficiency blue phosphorescence is one of the challenges in the field of organic phosphorescent materials.

[0004] Metal complexes containing boron heterocycles can significantly improve the quantum efficiency of metal complexes and reduce the excited state lifetime. Patent CN202310819046.5 discloses a Pt complex containing a boron five-membered heterocycle. Based on the above research, while further improving the quantum efficiency and reducing the excited state lifetime, it is necessary to narrow the full width at half maximum (FWHM) of the emission peak and minimize the material cost to the greatest extent.

[0005] In view of the above reasons, the present invention is specifically proposed. Summary of the Invention

[0006] In order to solve the above problems existing in the prior art, the present invention provides a metal complex and its application. When the metal complex is used in an OLED, especially in the blue light emission region, it exhibits an enhanced phosphorescence quantum yield and is suitable as an emitter material in OLED applications.

[0007] The first aspect of the present invention provides a metal complex, the structure of which is shown in formula (I):

[0008]

[0009] wherein, Ring A is a 5-membered heterocyclic ring;

[0010] Ring C, Ring D and Ring E are each independently selected from a 5-membered carbocycle, a 5-membered heterocycle, a 6-membered carbocycle or a 6-membered heterocycle;

[0011] V 1 、V 2 、V 3 、V 4 are each independently selected from C or N;

[0012] X 1 、X 2 、X 3 Each independently selected from CR 1 or N;

[0013] R 2 、R 3 、R 4 Each independently represents mono- or poly-substituted to saturated substitution, or unsubstituted;

[0014] L 1 , L 2 , L 3 Each independently selected from a single bond, O, S, S=O, SO2, Se, NR 5 PR 5 、R 5 P=O、CR 5 R 6 、C=O、SiR 5 R 6 ,GeR 5 R 6 , or BR 5 ;

[0015] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 At each occurrence, each is independently selected from hydrogen or the group consisting of: deuterium, halogen, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfide, selenoyl, sulfinyl, sulfonyl, phosphine, substituted or unsubstituted C1-C 40 Straight chain alkyl, substituted or unsubstituted C1~C 40linear or branched heteroalkyl, substituted or unsubstituted, having C3-C 40 branched or cyclic alkyl, substituted or unsubstituted, having C3-C 40 heterocycloalkyl, substituted or unsubstituted, having C1-C 40 alkoxy, substituted or unsubstituted, having C6-C 60 arylalkyl, substituted or unsubstituted, having C6-C 60 aryloxy, substituted or unsubstituted, having C6-C 60 arylamino, substituted or unsubstituted, having C3-C 40 silyl, substituted or unsubstituted, having C2-C 40 alkenyl, substituted or unsubstituted, having C4-C 40 cycloalkenyl, substituted or unsubstituted, having C2-C 40 heteroalkenyl, substituted or unsubstituted, having C2-C 40 alkynyl, substituted or unsubstituted, having C6-C 60 aryl, substituted or unsubstituted, having C6-C 60 arylsilyl, substituted or unsubstituted, having C2-C 60 heteroaryl and combinations thereof,

[0016] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 the substituents in are selected from deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C 20 alkyl, C1-C 20 heteroalkyl, C2-C 20 alkenyl, C3-C 20 cycloalkyl, C3-C 20 heterocycloalkyl, C1-C 20 alkoxy, C3~C 20 silyl, C6-C 30 arylamino, C6-C 30 arylsilyl, C3-C 30 heteroarylamino, C6-C 30 aryloxy, C3-C 30 heteroaryloxy, C6-C 30 arylthio, C3-C 30 heteroarylthio, C6-C 30 aryl, C3-C 30 any one or a combination of at least two of heteroaryl;

[0017] any two or more adjacent R 1, R 2 , R 3 , R 4 , R 5 , R 6 Optionally, they may be joined or fused to form a substituted or unsubstituted ring.

[0018] The metal complex of the present invention has good electroluminescence stability and excellent luminescence efficiency.

[0019] In the substituted or unsubstituted ring formed by the binding of adjacent groups to each other in the present invention, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. A fused ring refers to a fused aliphatic ring, a fused aromatic ring, a fused aliphatic heterocyclic ring, a fused aromatic heterocyclic ring, or a form composed of their combination.

[0020] The 5-membered carbon ring described in the present invention is a monocyclic and polycyclic system having 5 carbon atoms. The polycyclic ring is a ring system having two or more rings in which two carbons are shared by two adjacent rings. For example, the 5-membered carbon ring can be cyclopentane, cyclopentene, 2,3-dihydroindene, indene, etc. The 5-membered heterocyclic ring refers to a 5-membered carbon ring containing at least one heteroatom, and the total number of heteroatoms and carbon atoms constituting the ring is 5. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases, oxygen, sulfur, or nitrogen is a preferred heteroatom. Non-limiting examples of the 5-membered heterocyclic ring include: pyrazole, imidazole, oxazole, thiazole, triazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, benzimidazole, benzoxazole, benzotriazole, etc.

[0021] The 6-membered carbon ring described in the present invention is a monocyclic and polycyclic system having 6 carbon atoms. Preferably, the 6-membered carbon ring refers to the aryl group described in the present invention. The 6-membered heterocyclic ring refers to a ring system in which the total number of heteroatoms and carbon atoms is 6. Preferably, the 6-membered heterocyclic ring refers to a 6-membered heteroaryl group, such as: pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, etc.

[0022] Preferably, the ring C is a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0023] Preferably, the ring D and the ring E are each independently selected from a 5-membered heteroaromatic ring, a 6-membered aromatic ring, or a 6-membered heteroaromatic ring.

[0024] Preferably, the ring A is selected from the group consisting of:

[0025]

[0026]

[0027] wherein each R 1are the same or different and represent mono-substitution, di-substitution or multi-substitution up to saturated substitution, or no substitution;

[0028] W is selected from O, S, NR 5 , PR 5 , R 5 P═O, CR 5 R 6 , SiR 5 R 6 , BR 5 , S═O, SO2, C═O, AsR 5 , R 5 As═O, GeR 5 R 6 ; R 1 , R 5 and R 6 have the same meanings as defined above.

[0029] Preferably, the metal complex is selected from the group consisting of:

[0030]

[0031]

[0032]

[0033] wherein, W is selected from O, S, NR 5 , PR 5 , R 5 P═O, CR 5 R 6 , SiR 5 R 6 , BR 5 , S═O, SO2, C═O, AsR 5 , R 5 As═O, GeR 5 R 6 ; V 2 , V 3 , V 4 , L 1 , L 2 , R 1 ~R 6 The definitions of ring A, ring C, ring D, and ring E are the same as those in formula (I).

[0034] In some embodiments, the W is selected from O, S, NR 5 or CR 5 R 6 .

[0035] In some embodiments, R5 ~R 6 is the same as defined in formula (I).

[0036] In some embodiments, the metal complex is selected from the group consisting of:

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] wherein, V 1 ~V 4 、L 1 、L 2 、L 3 、R 1 ~R 4 、ring A, and ring C are defined the same as in formula (I);

[0043] R 7 、R 8 each independently represents single-substituted, multi-substituted to fully substituted, or unsubstituted;

[0044] R 7 、R 8 each time it appears, is independently selected from hydrogen or the group consisting of: deuterium, halogen atom, nitrile group, acyl group, carboxylic acid, ether, ester group, isonitrile group, sulfide group, selenoalkyl group, sulfinyl group, sulfonyl group, phosphino group, substituted or unsubstituted straight-chain alkyl having C1~C 40 、substituted or unsubstituted straight-chain or branched heteroakyl having C1~C 40 、substituted or unsubstituted branched or cyclic alkyl having C3~C 40 、substituted or unsubstituted heterocycloakyl having C3~C 40 、substituted or unsubstituted alkoxy having C1~C 40 、substituted or unsubstituted arylalkyl having C6~C 60 、substituted or unsubstituted aryloxy having C6~C 60 、substituted or unsubstituted arylamino having C6~C 60 、substituted or unsubstituted silyl having C3~C 40 、substituted or unsubstituted alkenyl having C2~C 40 、substituted or unsubstituted alkynyl having C4~C 40Cycloalkenyl, substituted or unsubstituted C2~C 40 Heteroalkenyl, substituted or unsubstituted C2~C 40 Alkynyl, substituted or unsubstituted C6~C 60 aryl, substituted or unsubstituted C6~C 60 Aryl silicon group, substituted or unsubstituted C2~C 60 heteroaryl and combinations thereof;

[0045] R 7 、R 8 The substituents substituted in the group are selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C 20 Alkyl, C1-C 20 Heteroalkyl, C2-C 20 Alkenyl, C3-C 20 Cycloalkyl, C3-C 20 Heterocycloalkyl, C1-C 20 Alkoxy, C3~C 20 Silane groups, C6-C 30 Arylamino, C6-C 30 Arylsilyl, C3-C 30 Heteroarylamino, C6-C 30 Aryloxy, C3-C 30 Heteroaryloxy, C6-C 30 Arylthio, C3-C 30 Heteroarylthio, C6-C 30 Aryl, C3-C 30 Any one or a combination of at least two of heteroaryl groups;

[0046] Any two or more adjacent R 7 、R 8 They may be optionally joined or fused to form a substituted or unsubstituted ring.

[0047] X 8 ~X 13 Each independently selected from C, O, N, CR 1 NR 5 ;

[0048] Y is independently selected from N, P, P=O, CR 9 、SiR 9 or GeR 9 ;

[0049] Z is independently selected from a single bond, O, S, NR 10 PR 10 、R 10 P=O、CR 10 R 11 、SiR10 R 11 、BR 10 、S=O, SO2, C=O, AsR 10 、R 10 、As=O, GeR 10 R 11 、 or without Z, or a group consisting of the following groups:

[0050]

[0051]

[0052] wherein n is selected from 0, 1, 2 or 3;

[0053] R 7 、R 8 each independently represents mono-substituted or multi-substituted to saturated substitution, or unsubstituted;

[0054] R 7 、R 8 、R 9 、R 10 、R 11 、R 12 each independently selected from hydrogen or a group consisting of: deuterium, halogen atom, nitrile group, acyl group, carboxylic acid, ether, ester group, isonitrile group, sulfhydryl group, selenoalkyl group, sulfinyl group, sulfonyl group, phosphino group, substituted or unsubstituted straight-chain alkyl having C1-C 40 、substituted or unsubstituted straight-chain or branched heteroakyl having C1-C 40 、substituted or unsubstituted branched or cyclic alkyl having C3-C 40 、substituted or unsubstituted heterocycloakyl having C3-C 40 、substituted or unsubstituted alkoxy having C1-C 40 、substituted or unsubstituted arylalkyl having C6-C 60 、substituted or unsubstituted aryloxy having C6-C 60 、substituted or unsubstituted arylamino having C6-C 60 、substituted or unsubstituted silyl having C3-C 40 、substituted or unsubstituted alkenyl having C2-C 40 、substituted or unsubstituted cycloalkenyl having C4-C 40 、substituted or unsubstituted heteroalkenyl having C2-C 40 、substituted or unsubstituted alkynyl having C2-C 40 、substituted or unsubstituted aryl having C6-C 60 、substituted or unsubstituted aryl having C6-C 60aryl-silyl, substituted or unsubstituted C2-C 60 heteroaryl and combinations thereof;

[0055] R 7 、R 8 、R 9 、R 10 、R 11 、R 12 The substituents in are selected from deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C 20 alkyl, C1-C 20 heteroalkyl, C2-C 20 alkenyl, C3-C 20 cycloalkyl, C3-C 20 heterocycloalkyl, C1-C 20 alkoxy, C3-C 20 silyl, C6-C 30 arylamino, C6-C 30 aryl-silyl, C3-C 30 heteroarylamino, C6-C 30 aryloxy, C3-C 30 heteroaryloxy, C6-C 30 arylthio, C3-C 30 heteroarylthio, C6-C 30 aryl, C3-C 30 heteroaryl, or a combination of any one or at least two thereof;

[0056] Any two or more adjacent R 7 、R 8 、R 9 、R 10 、R 11 、R 12 may optionally be joined or cyclized to form a substituted or unsubstituted ring.

[0057] Preferably, Y is N.

[0058] Preferably, the L 1 、L 2 each independently selected from a single bond, O, S, S=O, SO2, CR 5 R 6 、C=O or SiR 5 R 6 。 "

[0059] Preferably, L 3 each independently selected from a single bond, O.

[0060] Preferably, the Z are each independently selected from O, S, S=O, SO2, CR 9 R 10, C=O, SiR 9 R 10 or NR 11 .

[0061] Preferably, the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 are each independently selected from hydrogen, deuterium, fluorine, cyano group, a straight-chain alkyl having C1-C 40 , a straight-chain heteroalkyl having C1-C 40 , a branched or cyclic alkyl having C3-C 40 , an alkoxy group having C1-C 40 , an arylalkyl having C6-C 60 , an arylamino group having C6-C 60 , a silyl group having C3-C 40 , an aryl group having C6-C 60 , a heteroaryl group having C2-C 60 and combinations thereof.

[0062] Furthermore, the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, cyano group, R A1 -R A30 , R B1 -R B195 , R C1 -R C80 ;

[0063] Among them, the structural formulas of R A1 -R A30 are as follows:

[0064]

[0065] R B1 -R B195The structure shown is as follows:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] R C1 ~R C80 The structure shown is as follows:

[0073]

[0074]

[0075] Each hydrogen atom in each substituent can be replaced by a deuterium atom.

[0076] In some embodiments, L 1 、L 2 、L 3 are each independently selected from a single bond, O, S, S=O, SO2, CR 5 R 6 、C=O or SiR 5 R 6 .

[0077] In some embodiments, Y is N.

[0078] In some embodiments, Z is each independently selected from O, S, S=O, SO2, CR 9 R 10 、C=O、SiR 9 R 10 or NR 11 .

[0079] Furthermore, the R 5 、R 6 、R 9 、R 10 、R 11 are each independently selected from the group consisting of: R A1 ~R A26 、R B1 ~R B185 、R C1 ~R C79 .

[0080] Further, said R 1 , R 2 , R 3 , R 4 , R 7 , R 8 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, isocyano, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 ; R 2 , R 3 , R 4 , R 7 , R 8 each represents mono-substituted or multi-substituted to saturated substitution or unsubstituted, and any two or more adjacent substituents may optionally be joined or fused to form a substituted or unsubstituted ring.

[0081] Still further, said L 1 , L 2 , L 3 are each independently selected from a single bond, O, S or CR 5 R 6 .

[0082] Still further, said Z are each independently selected from O, S, CR 9 R 10 , or NR 11 .

[0083] Still further, said R 5 , R 6 , R 9 , R 10 , R 11 are each independently selected from the group consisting of R A1 , R A10 , R B1 , R C1 .

[0084] Still further, said R 1 , R 2 , R 3 , R 4 , R 7 , R 8 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 ; R 2, R 3 , R 4 , R 7 , R 8 Each represents mono-substituted or multi-substituted to fully saturated or unsubstituted.

[0085] According to an embodiment of the present invention, the metal complex is selected from the group consisting of:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] Among them, some or all of the hydrogen atoms in each structure can be replaced by deuterium atoms. The present invention also provides an application of the metal complex described above in an organic electroluminescent device. The organic electroluminescent device of the present invention can obtain blue light with high luminous efficiency.

[0108] The second aspect of the present invention provides an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, and the organic layer contains the metal complex of the first aspect.

[0109] The organic layer of the present invention can be an emission layer and the metal complex as described herein can be an emission dopant or a non-emission dopant.

[0110] Furthermore, the organic layer can further contain a host material and a dopant, wherein the dopant contains the metal complex of the first aspect of the present invention.

[0111] The metal complex can be a sensitizer; wherein the device can further include a receptor, a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0112] The organic electroluminescent device of the present invention can also include an emission region, and the emission region contains a compound as disclosed in the above compound part of the present disclosure.

[0113] Furthermore, the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, fluorene, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene) or a combination derived from these systems.

[0114] In some embodiments, the mass ratio of the host material to the doping material is: 99:1 to 1:99.

[0115] Preferably, the mass ratio of the host material to the doping material is: 99:1 to 50:50.

[0116] More preferably, the mass ratio of the host material to the doping material is: 98:2 to 90:10.

[0117] The materials described herein as suitable for specific layers in an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0118] These methods are generally known to those of ordinary skill in the art, and they can be applied to organic electroluminescent devices containing the compounds according to the present invention without creative effort.

[0119] According to one embodiment, novel ligands of metal complexes are disclosed. The inventors have found that the introduction of these ligands unexpectedly narrows the emission spectrum, reduces the sublimation temperature, and improves the luminescence efficiency of the device.

[0120] As a method for preparing the organic electroluminescent device of the present invention, the following preparation methods can be cited, but are not limited thereto, and those skilled in the art can make various changes based on the common general knowledge in the art. The foregoing preparation method includes the following steps:

[0121] Cleaning step: Cleaning the glass substrate with ITO using a cleaning agent, deionized water, an organic solvent, etc.;

[0122] Step of forming a hole injection layer: Evaporating a hole injection layer forming material containing the organic electroluminescent material of the present invention on the foregoing anode layer by vacuum evaporation to form a hole injection layer containing the organic electroluminescent material of the present invention on the foregoing substrate;

[0123] Step of forming a hole transport layer: Forming a hole transport layer on the foregoing hole injection layer by vacuum evaporation;

[0124] Step of forming an organic light-emitting layer: Evaporating an organic light-emitting layer forming material containing the material of the present invention on the foregoing hole transport layer by vacuum evaporation to form an organic light-emitting layer containing the organic electroluminescent material of the present invention on the foregoing hole transport layer;

[0125] Step of forming an electron transport layer: Evaporating an electron transport layer forming material containing the organic electroluminescent material of the present invention on the foregoing organic light-emitting layer by vacuum evaporation to form an electron transport layer containing the organic electroluminescent material of the present invention on the foregoing organic light-emitting layer;

[0126] Step of forming a cathode layer: Evaporating, sputtering, or spin-coating a cathode forming material on the foregoing electron transport layer to form a cathode layer.

[0127] A third aspect of the present invention provides a consumer product, which includes the organic electroluminescent device described in the second aspect.

[0128] The consumer product of the present invention can be one of the following products: flat panel display, computer monitor, medical monitor, television, billboard, lamp for internal or external lighting and / or signaling, head-up display, fully transparent or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, video camera, viewfinder, microdisplay with a diagonal less than 2 inches, 3-D display, virtual reality or augmented reality display, vehicle, video wall comprising a plurality of tiled together displays, theater or stadium screen, light therapy device, and signpost.

[0129] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0130] (1) When the metal complex of the present invention is used in an OLED, especially in the blue emission region, it exhibits enhanced phosphorescence quantum yield and relatively short excited state lifetime, good luminescence stability, high luminescence efficiency, and is suitable as an emitter material in OLED applications. The metal complex of the present invention can obtain an organic electroluminescent device with blue phosphorescent electroluminescence and improved luminescence efficiency, and the luminescent device has good thermal stability. The consumer product of the organic light-emitting device of the present invention can obtain an electronic device with blue phosphorescent electroluminescence and improved luminescence efficiency by containing the organic electroluminescent device of the present invention;

[0131] (2) The metal complex of the present invention regulates its photophysical properties by adjusting the structure of the ligand around the metal center and controlling the structure of the substituents on the ligand, and has the advantages of narrow emission spectrum, high stability, and high efficiency, and has broad application prospects in many fields such as OLED display and lighting. Description of the Drawings

[0132] In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the following drawings are only some embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative efforts.

[0133] Figure 1Schematic diagram showing an organic light-emitting device 100. The illustration is not necessarily drawn to scale. Device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. Device 100 can be fabricated by sequentially depositing the described layers.

[0134] Figure 2 Schematic diagram showing an organic light-emitting device 200. The illustration is not necessarily drawn to scale. Device 200 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. Device 200 is an example of device 100 with the hole blocking layer 107 omitted and can be fabricated by a method similar to that of device 100.

[0135] Figure 3 Schematic diagram showing an organic light-emitting device 300 with two light-emitting layers. The device includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a first light-emitting layer 1061, an electron transport layer 108, a charge generation layer 1022, a hole injection layer 103, a hole transport layer 104, a second light-emitting layer 1063, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer 111. Device 300 can be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light-emitting layer, while device 300 has a first light-emitting layer and a second light-emitting layer, the emission peak shapes of the first light-emitting layer and the second light-emitting layer can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 300, materials similar to those described for device 100 can be used. Figure 3 An example of how some layers can be added to the structure of device 100 is provided. Detailed Description

[0136] To make the objectives, technical solutions, and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without any creative efforts belong to the scope of protection of the present invention.

[0137] "Aryl" according to the present invention means and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycycle can have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is an aromatic hydrocarbon group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl. Preferred aryl groups are aryl groups containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group can be optionally substituted.

[0138] "Heteroaryl" in the sense of the present invention means and includes monocyclic aromatic groups and polycyclic aromatic ring systems containing at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases, oxygen, sulfur, or nitrogen are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring can have one to six heteroatoms. The heteropolycyclic system can have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl. The heteropolycyclic aromatic ring system can have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are heteroaryl groups containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazene, and their nitrogen analogs. Additionally, the heteroaryl group can be optionally substituted.

[0139] For the purposes of the present invention, the alkyl group contains 1 to 40 carbon atoms, and the straight-chain or branched alkyl group, alkenyl group or alkynyl group in which a single hydrogen atom or -CH2- group may also be substituted contains at least two carbon atoms. As non-limiting examples, the alkyl group, alkenyl group or alkynyl group is preferably considered to refer to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0140] Alkoxy groups preferably having 1 to 40 carbon atoms are considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.

[0141] Heteroalkyl groups preferably having 1 to 40 carbon atoms are alkyl groups in which a single hydrogen atom or -CH2- group is substituted by an oxygen, sulfur or halogen atom, and are considered to be alkoxy groups, alkylthio groups, fluorinated alkoxy groups, fluorinated alkylthio groups, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, ethenoxy, ethenthio, propenoxy, propenethio, butenethio, butenoxy, pentenoxy, pentenethio, cyclopentenoxy, cyclopentenethio, hexenoxy, hexenethio, cyclohexenoxy, cyclohexenethio, ethynoxy, ethynthio, propynoxy, propynthio, butynoxy, butynthio, pentynoxy, pentynthio, hexynoxy, hexynthio.

[0142] Generally, the cycloalkyl group and cycloalkenyl group according to the present invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, in which one or more -CH2- groups may be replaced by the above groups; in addition, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0143] The alkenyl or alkynyl group according to the present invention has 2 to 40 carbon atoms, and the alkenyl or alkynyl group in which a single hydrogen atom can be substituted is preferably vinyl, propenyl, butenyl, isobutenyl, styryl, stilbenyl, ethynyl, propynyl, butynyl, phenylacetylenyl; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0144] The aryl or heteroaryl group according to the present invention particularly refers to a group derived from the following substances: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, fluorenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenylbenzene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthryl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluorene, cis- or trans-indeno[2,3-b]carbazole, cis- or trans-indolo[2,3-b]carbazole, trindene, isotrindene, spirotrindene, spiroisotrindene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazaphenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylene, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoranthene ring, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthroline, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.

[0145] "Acyl" in the sense of the present invention refers to a substituted carbonyl group (COR).

[0146] "Ester group" in the sense of the present invention refers to a substituted oxycarbonyl group (-OCOR or CO2R).

[0147] "Ether group" in the sense of the present invention refers to the -OR group.

[0148] The "sulfur group" or "sulfide" described herein is used interchangeably and refers to the -SR group.

[0149] "Sulfinyl group" in the sense of the present invention refers to the -SOR group.

[0150] "Sulfonyl group" in the sense of the present invention refers to the -SO2R group.

[0151] "Phosphino group" in the sense of the present invention refers to the -PR3 group, where each R can be the same or different.

[0152] "Silyl group" in the sense of the present invention refers to the -SiR3 group, where each R can be the same or different.

[0153] Each of the above Rs is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl.

[0154] The aryloxy used in the present invention refers to the monovalent functional group represented by R'O - wherein R' is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy groups include phenoxy, naphthoxy, biphenyloxy, and the like.

[0155] The alkylsilyl used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl is at least 3. Non-limiting examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, and the like. Arylsilyl refers to a silyl group substituted by an aryl group having 6 to 60 carbon atoms.

[0156] The arylphosphino used in the present invention refers to a diarylphosphino group substituted by an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylphosphino groups include diphenylphosphino, bis(4-trimethylsilylphenyl)phosphino, and the like. Aryloxyphosphino is the arylphosphino group in which the phosphorus atom is oxidized to the highest valence state.

[0157] The arylboron used in the present invention refers to a diarylboron group substituted by an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylboron groups include diphenylboron, bis(2,4,6-trimethylphenyl)boron, and the like. Alkylboron refers to a dialkylboron group substituted by an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of alkylboron groups include di-tert-butylboron, diisobutylboron, and the like.

[0158] As used in the present invention, the terms "halogen", "halogen atom", "halo group" are used interchangeably and refer to fluorine, chlorine, bromine or iodine.

[0159] As used herein, "a combination thereof" or "a group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be envisioned by one of ordinary skill in the art from the applicable list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent, such as trifluoromethyl, etc.; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group.

[0160] In the present invention, the term "substituted or unsubstituted" means being substituted by one or more substituents selected from hydrogen, deuterium, halogen atoms, hydroxyl groups, nitrile groups, nitro groups, amino groups, amidino groups, hydrazino groups, hydrazono groups, carboxyl groups or their carboxylates, sulfonic acid groups or their sulfonates, phosphoric acid groups or their phosphates, C1-C 40 alkyl groups, C2-C 40 alkenyl groups, C2-C 40 alkynyl groups, C1-C 40 alkoxy groups, C3-C 40 cycloalkyl groups, C3-C 40 cycloalkenyl groups, C6-C 60 aryl groups, C6-C 60 aryloxy groups, C6-C 60 arylthioether groups and C2-C 60 heteroaryl groups, or being substituted or unsubstituted by a substituent formed by linking two or more of the above-exemplified substituents.

[0161] In one example, the term "substituted" includes a combination of two to four of the listed groups.

[0162] In another example, the term "substituted" includes a combination of two to three groups. In yet another example, the term "substituted" includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0163] In the present invention, "EQE" refers to the external quantum efficiency of a device, that is, the ratio of the number of photons emitted by the device to the number of electrons injected into the device.

[0164] The organic electroluminescent device described in the present invention includes at least one organic layer, which is disposed between the anode and the cathode and is electrically connected to the anode and the cathode. Figure 1Schematic diagram showing an organic light-emitting device 100. The illustration is not necessarily drawn to scale. Device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. Device 100 can be fabricated by sequentially depositing the described layers.

[0165] Figure 2 Schematic diagram showing an organic light-emitting device 200 having two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. Device 200 can be prepared by sequentially depositing the described layers. Since the most common OLED devices have a single monochromatic light-emitting layer or have three light-emitting layers of the three primary colors, while device 200 has two light-emitting layers of the same light color. In the corresponding layers of device 200, materials similar to those described with respect to device 100 can be used. Figure 2 Provide an example of how some layers can be added to the structure of device 100.

[0166] Figure 1 and Figure 2 The simple layered structures illustrated in and are provided as non-limiting examples, and it should be understood that embodiments of the present invention can be used in combination with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be achieved by combining the described individual layers in different ways based on design, performance, and cost factors, or certain layers can be completely omitted. Other layers not specifically described can also be included. Materials different from those specifically described can be used. Although many of the examples provided herein describe various layers as including a single material, it will be understood that combinations of materials can be used, such as a mixture of a matrix and a dopant, or more generally, a mixture. And, the layers can have various sub-layers. The names given to the individual layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into light-emitting layer 205, and can be described as a hole transport layer or an electron blocking layer. In one embodiment, an OLED can be described as having an organic layer disposed between a cathode and an anode. This organic layer can include a single layer or can further include multiple layers of different organic materials as described in examples Figure 1 and Figure 2 described.

[0167] Structures and materials not specifically described may also be used, such as PLEDs containing polymeric materials. As another example, OLEDs with a single organic layer or multiple stacks may be used. The OLED structure may deviate from Figure 1 and Figure 2 the simple layered structure illustrated in. For example, the substrate may include angled reflective surfaces to improve light coupling.

[0168] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or sublimation by means of a carrier gas to apply one or more layers, where the material is applied at a pressure between 10 -5 mbar and 1 bar. A particular example of this method is organic vapor jet printing, where the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include, for example, spin coating, or generating one or more layers by means of any desired printing method such as screen printing, flexographic printing, lithographic printing, photothermographic imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds are obtained, for example, by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers, and polymers. Additionally feasible are hybrid methods, where, for example, one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition.

[0169] Devices manufactured according to embodiments of the present invention may further optionally include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapors, and / or gases, etc. The barrier layer may be deposited on the substrate, on the electrodes, under the substrate, under the electrodes, beside the substrate, beside the electrodes, or on any other part of the device, including the edges. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions with a single phase as well as compositions with multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer includes a mixture of a polymeric material and a non-polymeric material. In order to be considered a mixture, the aforementioned polymeric and non-polymeric materials constituting the barrier layer should be deposited under the same conditions and / or simultaneously. The weight ratio of the polymeric material to the non-polymeric material may be in the range of 95 / 5 to 5 / 95. In one example, the mixture of the polymeric material and the non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0170] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as (but not limited to) methyl, phenyl, pyridyl, etc., can be in its non-deuterated, partially deuterated, and fully deuterated forms. Similarly, the substituent classes (such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0171] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can use the materials and structures.

[0172] Furthermore, organic devices such as organic transistors can use the materials and structures.

[0173] In the following examples of the present invention, unless otherwise specified, conventional preparation methods are used. The raw materials used can be obtained from public commercial sources unless otherwise specified, and the percentages are mass percentages unless otherwise specified.

[0174] To illustrate the present invention more clearly, the technical solutions of the present invention will be described below in conjunction with some specific examples:

[0175] In the examples of the present invention, the performance detection conditions of the prepared electroluminescent device are as follows:

[0176] Chromaticity coordinates: measured using a spectral scanner PhotoResearch PR-715;

[0177] Current-voltage: measured using a digital source meter Keithley 2420;

[0178] Power efficiency: measured using a NEWPORT 1931-C;

[0179] Luminance: measured using a luminance meter Minolta Cs-1000A.

[0180] Example 1

[0181] A method for preparing a metal complex P1, comprising the following steps:

[0182] The first step: Preparation of compound Int-1

[0183]

[0184] Under nitrogen protection, 20.0 mmol of sub-1, 10.0 mmol of sub-2, 1.0 mmol of copper(I) iodide, 2.0 mmol of L-proline and 40.0 mmol of anhydrous potassium carbonate were dispersed in 60 mL of dimethyl sulfoxide. The temperature was raised to 110 °C and the mixture was stirred for 24 hours. After cooling to room temperature, the reaction mixture was poured into 150 mL of water, extracted with ethyl acetate, the organic phase was washed with saturated brine, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography to obtain compound Int-1, a yellow solid, with a yield of 65%.

[0185] Step 2: Preparation of compound Int-2

[0186]

[0187] Under nitrogen protection, 20.0 mmol of Int-1, 30.0 mmol of triisopropyl borate and 80 mL of dry THF were mixed. The temperature was cooled to -78 °C, and 12 mL of 2.5 M n-butyllithium in hexane solution was added dropwise. The mixture was stirred for 1 hour, then warmed to room temperature, and 20 mL of 3 M dilute hydrochloric acid aqueous solution was added dropwise. The mixture was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. The residue was dispersed in n-hexane, filtered, and the filter cake was washed with n-hexane to obtain compound Int-2, a yellow solid, with a yield of 84%.

[0188] Step 3: Preparation of compound Int-3

[0189]

[0190] 20.0 mmol of Int-2 was dispersed in 100 mL of dry toluene, and 24.0 mmol of 1,2-diphenylethylenediamine (sub-3), 24.0 mmol of p-toluenesulfonic acid, 2.0 mmol of anhydrous magnesium sulfate and 20 g of molecular sieve were added. The temperature was raised to reflux and the mixture was stirred for 24 hours. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure to dryness. 150 mL of dry toluene was added, and then 200.0 mmol of manganese dioxide was added. The temperature was raised to reflux and the mixture was stirred for 24 hours. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography to obtain compound Int-3, a yellow solid, with a yield of 75%.

[0191] Step 4: Preparation of compound Int-4

[0192]

[0193] Under nitrogen protection, 20.0 mmol of Int-3 was dissolved in 150 mL of acetone, and 24.0 mmol of methyl iodide was slowly added dropwise. The mixture was stirred at room temperature for 3 days, concentrated under reduced pressure until about 20 mL remained, 100 mL of ethyl acetate was added, filtered, and the filter cake was washed with ethyl acetate. The obtained solid was dissolved in 150 mL of methanol and 15 mL of water, 40.0 mmol of ammonium hexafluorophosphate was added, and the mixture was stirred at room temperature for 3 days. The remaining small amount of water was concentrated under reduced pressure, 50 mL of water was added, filtered, and the filter cake was washed with water and dried to obtain compound Int-4, a gray solid, with a yield of 55%.

[0194] Step 5: Preparation of Compound P1

[0195]

[0196] Under nitrogen protection, 15.0 mmol of Int-4 was dispersed in 150 mL of 1,4-dioxane, 16.5 mmol of palladium acetate and 45.0 mmol of anhydrous potassium carbonate were added, and the mixture was stirred and heated to 110 °C for 48 hours. It was cooled to room temperature, concentrated to dryness under reduced pressure, and purified by silica gel column chromatography to obtain compound P1, a yellow solid, with a yield of 58%, HRMS(ESI): 647.1233[M+H] + 。 1 HNMR(δ, DMSO-d6): 8.43~8.40(1H, m); 7.81~7.73(5H, m); 7.55~7.36(11H, m); 7.30~7.24(2H, m); 7.01~6.98(1H, m); 6.92~6.89(1H, m); 6.65(1H, s); 4.14(3H, s).

[0197] Example 2

[0198] A method for preparing metal complex P32, comprising the following steps:

[0199] Step 1: Preparation of Compound Int-6

[0200]

[0201] Under nitrogen protection, 22.0 mmol of Int-5 (prepared according to the synthesis method in the third step of Reference Example 1) was dissolved in 80 mL of DMF, and 20.0 mmol of sub-4, 2.0 mmol of cuprous iodide, 40.0 mmol of anhydrous cesium carbonate, and 4.0 mmol of picolinic acid were added. The temperature was raised to 120 °C, and the mixture was stirred and reacted for 24 hours. Then it was cooled to room temperature. The reaction solution was poured into 200 mL of water, extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness, and purified by silica gel column chromatography to obtain intermediate Int-6, a brown solid, yield: 90%.

[0202] Step 2: Preparation of Compound P32

[0203]

[0204] Under nitrogen protection, 15.0 mmol of Int-6 was dispersed in 150 mL of 1,4-dioxane, 16.5 mmol of palladium acetate and 45.0 mmol of anhydrous potassium carbonate were added, and the mixture was stirred and heated to 110 °C for reaction for 48 hours. Then it was cooled to room temperature, concentrated to dryness under reduced pressure, and purified by silica gel column chromatography to obtain compound P32, a yellow solid, yield: 65%, HRMS (ESI): 638.1279 [M + H] + 。 1 HNMR (δ, DMSO-d6): 9.04 (1H, s); 8.78 (1H, s); 8.75 (1H, s); 8.35 - 8.33 (1H, dd); 8.15 - 8.13 (1H, m); 7.82 - 7.75 (3H, m); 7.51 - 7.44 (2H, m); 7.39 - 7.31 (3H, m); 7.23 (1H, s); 7.14 - 7.13 (1H, d); 6.96 - 6.94 (1H, d); 6.85 (1H, s); 1.32 (9H, s).

[0205] Example 3

[0206] A method for preparing metal complex P188, comprising the following steps:

[0207] Step 1: Preparation of Compound Int-7

[0208]

[0209] Under nitrogen protection, 20.0 mmol of sub-5 was dispersed in 100 mL of dry toluene, and 24.0 mmol of sub-6, 24.0 mmol of p-toluenesulfonic acid, 2.0 mmol of anhydrous magnesium sulfate, and 20 g of The molecular sieve was heated to reflux and stirred for reaction for 24 hours, cooled to room temperature, filtered, the filtrate was concentrated to dryness under reduced pressure, 150 mL of dry toluene was added, then 0.1 mol of manganese dioxide was added, heated to reflux and stirred for reaction for 24 hours, cooled to room temperature, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain compound Int-7, a yellow solid, with a yield of 87%.

[0210] Step 2: Preparation of compound Int-8

[0211]

[0212] Referring to the synthesis method of the first step in Example 2, Int-5 in the first step of Example 2 was replaced with Int-7, and sub-4 was replaced with sub-7 to prepare compound Int-8, a brown solid, with a yield of 91%.

[0213] Step 3: Preparation of compound P188

[0214]

[0215] Referring to the synthesis method of the second step in Example 2, only Int-6 in the second step of Example 2 was replaced with Int-8 to prepare compound P188, a yellow solid, with a yield of 63%, HRMS(ESI): 750.2528[M+H] + 。 1 HNMR(δ, DMSO-d6): 8.72~8.70(1H, d); 8.35~8.33(1H, m); 8.15~8.13(1H, m); 7.87~7.82(2H, m); 7.61~7.56(4H, m); 7.50~7.44(3H, m); 7.35~7.31(1H, m); 7.17~7.13(1H, m); 6.96~6.94(1H, d); 1.33(18H, s); 1.31(9H, s).

[0216] Example 4

[0217] The preparation method of the metal complex P370 includes the following steps:

[0218] Step 1: Preparation of compound Int-9

[0219]

[0220] Under nitrogen protection, 24.0 mmol of 3-methoxybromobenzene was dissolved in 60 mL of dry anisole, cooled to -78 °C, and 11.5 mL of 2.5 M n-butyllithium in n-hexane solution was added dropwise. The mixture was stirred for 30 minutes, then 29.0 mmol of boron tribromide was added dropwise and stirred for 1 hour. 20.0 mmol of sub-8 and 20 mL of diisopropylethylamine were added, and the mixture was stirred for 1 hour, heated to 150 °C and stirred for 24 hours. After cooling to room temperature, it was concentrated to dryness under reduced pressure and purified by silica gel column chromatography to obtain compound Int-9, a white solid, with a yield of 59%.

[0221] Step 2: Preparation of compound Int-10

[0222]

[0223] Under nitrogen protection, 20.0 mmol of Int-9 was dissolved in 100 mL of dichloromethane, cooled to 0 °C, and 24.0 mmol of boron tribromide was added dropwise. The mixture was stirred for 1 hour, 50 mL of saturated aqueous sodium ethylenediaminetetraacetate solution was added dropwise, the organic phase was separated, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column chromatography to obtain compound Int-10, a white solid, with a yield of 92%.

[0224] Step 3: Preparation of compound Int-11

[0225]

[0226] Under nitrogen protection, 20.0 mmol of Int-10 and 22.0 mmol of sub-8 were dissolved in 60 mL of DMF, 30.0 mmol of anhydrous cesium carbonate was added, heated to 120 °C, and stirred for 15 hours. After cooling to room temperature, the reaction solution was poured into 150 mL of water, filtered, the filter cake was washed with water and ethanol, and purified by silica gel column chromatography to obtain compound Int-11, a yellow solid, with a yield of 86%.

[0227] Step 4: Preparation of compound P370

[0228]

[0229] Referring to the synthesis method in Step 2 of Example 2, only Int-6 in Step 2 of Example 2 was replaced with Int-11 to prepare compound P370, a white solid, with a yield of 56%, HRMS(ESI): 628.1309[M+H] + 。 1HNMR (δ, DMSO-d6): 9.24 - 9.22 (1H, d); 8.15 - 8.13 (1H, m); 8.09 - 8.03 (2H, m); 7.89 - 7.86 (1H, m); 7.78 - 7.74 (1H, m); 7.50 - 7.43 (4H, m); 7.33 - 7.25 (2H, m); 7.22 - 7.19 (1H, m); 7.16 (1H, s); 6.99 - 6.96 (1H, d); 6.90 - 6.88 (1H, m).

[0230] Examples 5 - 383

[0231] Referring to the similar synthesis methods of the above examples, the following compounds were prepared:

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268] Application Examples 1 to 387

[0269] Preparation of Organic Electroluminescent Element

[0270] An OLED element 100, such as Figure 1As shown in the figure, the OLED device of this embodiment is a top-emitting light device, including a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light-emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light-emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, a cathode 110 disposed on the electron injection layer 109, and a capping layer 111 disposed on the cathode. The preparation method of the device is as follows:

[0271] The glass substrate with the patterned ITO electrode is ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with an ultraviolet light cleaning machine for 10 minutes, and bombarded with a low-energy cation beam on the surface.

[0272] Place the above-treated ITO glass substrate in a vacuum chamber, evacuate to less than 1×10 -5 Pa, and deposit metallic silver as the anode on the above ITO film. The deposition thickness is Continue to deposit the compound HATCN as the hole injection layer respectively. The deposition thickness is Continue to deposit HTM as the hole transport layer on the above hole injection layer film. The deposition thickness is

[0273] Deposit BPrime as the electron blocking layer on the above hole transport layer. The deposition thickness is

[0274] Deposit the metal complex prepared in Example 1 and PH025 as the organic light-emitting layer of the device on the above electron blocking layer. Among them, PH025 is the host material and the metal complex of the present invention is the doping material, and the doping concentration is 5%. The deposition thickness is

[0275] Continue to deposit a layer of compound DPO as the hole blocking layer of the device on the above organic light-emitting layer. The deposition thickness is

[0276] Continue to deposit a layer of LiQ and ET318 as the electron transport layer of the device on the above hole blocking layer. Among them, LiQ is 50% of the mass of ET318. The deposition thickness is

[0277] Continue to deposit a layer of LiF as the electron injection layer of the device on the above electron transport layer. The deposition thickness is

[0278] On top of the above-mentioned electron injection layer, magnesium and silver are evaporated as the cathode layer of the device, where the mass ratio of magnesium to silver is 1:10, and the evaporation film thickness is

[0279] Finally, a compound HTM is evaporated on top of the cathode layer as a capping layer, and the evaporation film thickness is To fabricate the organic electroluminescent element of the present invention, as shown in the attached Figure 1 device 100.

[0280] Application Examples 2 to 387

[0281] The metal complexes prepared in Application Examples 2 to 387 are respectively used to replace the metal complex of the present invention in Application Example 1 above, and the other steps are the same as above.

[0282] Comparative Example 1

[0283] The compound shown in BD030 is used to replace the metal complex of the present invention in Application Example 1 above, and the other steps are the same as above to fabricate Comparative Element 1.

[0284] Comparative Example 2

[0285] The compound shown in BD031 is used to replace the metal complex of the present invention in Application Example 1 above, and the other steps are the same as above to fabricate Comparative Element 2.

[0286] The structural formulas of the aforementioned HATCN, HTM, BPrime, PH025, BD030, BD031, DPO, and ET318 are as follows:

[0287]

[0288] Application Example 388

[0289] Preparation of Organic Electroluminescent Element

[0290] An OLED element 200, as shown in Figure 2As shown, the OLED element of this embodiment is a top-emitting light element, including a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light-emitting layer 106 disposed on the electron blocking layer 105, an electron transport layer 108 disposed on the organic light-emitting layer 106, an electron injection layer 109 disposed on the electron transport layer 108, a cathode 110 disposed on the electron injection layer 109, and a capping layer 111 on the cathode. The OLED element of this embodiment is an element omitting the hole blocking layer 107. In the corresponding layers of the element 200, materials similar to those described for the element 100 can be used, and the element 200 of the present invention can be manufactured by referring to the manufacturing method of the element 100 in Application Example 1.

[0291] Application Example 389

[0292] Preparation of Organic Electroluminescent Element

[0293] Figure 3 Schematic diagram of an organic light-emitting device 300 showing two light-emitting layers. The device includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a first light-emitting layer 1061, an electron transport layer 108, a charge generation layer 1022, a hole injection layer 103, a hole transport layer 104, a second light-emitting layer 1063, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer 111. The device 300 can be prepared by sequentially depositing the described layers. Since the most common OLED device has one light-emitting layer, while the device 300 has a first light-emitting layer and a second light-emitting layer, the light-emitting peak shapes of the first light-emitting layer and the second light-emitting layer can be overlapping, cross-overlapping, or non-overlapping. In the corresponding layers of the device 300, materials similar to those described for the device 100 can be used. Figure 3 Provide an example of how some layers can be added to the structure of the device 100.

[0294] For the above-mentioned manufactured organic electroluminescent element, a digital source meter and a luminance meter are used to measure the driving voltage, current efficiency, and the lifetime of the light-emitting element. Specifically, the voltage is increased at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent element reaches 10 mA / cm 2 is measured as the driving voltage, and the luminance at this time is also measured; the ratio of the luminance to the current density is the current efficiency; the LT80% lifetime test is as follows: Using a luminance meter at a luminance of 1000 cd / m 2 while maintaining a constant current, measure the luminance decay of the organic electroluminescent element to 800 cd / m 2The time, in hours, and some of the test results are summarized in Table 1. The *data is normalized with respect to Comparative Example 1.

[0295] Table 1

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306] As can be seen from Table 1, compared with Comparative Element 1, for the organic electroluminescent device prepared with the metal complex of the present invention, after replacing the metal Pt with Pd, the organic electroluminescent device prepared with the metal complex of the present invention obtains relatively high efficiency and lifespan at a comparable driving voltage, and it is an organic electroluminescent material with excellent performance.

[0307] As described above, only representative examples of the specific embodiments of the present invention are provided, but the protection scope of the present invention is not limited thereto. Any person skilled in the art can easily think of variations or substitutions within the technical scope disclosed by the present invention, and all should be covered by the protection scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims

1. A metal complex, characterized in that, The structure of the metal complex is shown in formula (I): Wherein, ring A is a 5-membered heterocycle; Ring C, ring D and ring E are each independently selected from a 5-membered carbocycle, a 5-membered heterocycle, a 6-membered carbocycle or a 6-membered heterocycle; V 1 、V 2 、V 3 、V 4 are each independently selected from C or N; X 1 、X 2 、X 3 Each independently selected from CR 1 or N; R 2 、R 3 、R 4 each independently represents monosubstituted, polysubstituted to fully substituted, or unsubstituted; L 1 、L 2 、L 3 are each independently selected from a single bond, O, S, S═O, SO2, Se, NR 5 、PR 5 、R 5 P═O、CR 5 R 6 、C═O、SiR 5 R 6 、GeR 5 R 6 、or BR 5 ; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 At each occurrence, each is independently selected from hydrogen or the group consisting of: deuterium, halogen, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfide, selenoyl, sulfinyl, sulfonyl, phosphine, substituted or unsubstituted C1-C 40 Straight chain alkyl, substituted or unsubstituted C1~C 40 Straight or branched chain heteroalkyl, substituted or unsubstituted C3~C 40 branched or cyclic alkyl, substituted or unsubstituted C3~C 40 Heterocycloalkyl, substituted or unsubstituted C1~C 40 Alkoxy, substituted or unsubstituted C6~C 60 Arylalkyl, substituted or unsubstituted C6~C 60 aryloxy, substituted or unsubstituted C6~C 60 aromatic amino groups, substituted or unsubstituted C3~C 40 Silane group, substituted or unsubstituted C2~C 40 Alkenyl, substituted or unsubstituted C4~C 40 Cycloalkenyl, substituted or unsubstituted C2~C 40 Heteroalkenyl, substituted or unsubstituted C2~C 40 Alkynyl, substituted or unsubstituted C6~C 60 aryl, substituted or unsubstituted C6~C 60 Aryl silicon group, substituted or unsubstituted C2~C 60 heteroaryl and combinations thereof; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 The substituents substituted in R are selected from deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C 20 alkyl, C1-C 20 heteroalkyl, C2-C 20 alkenyl, C3-C 20 cycloalkyl, C3-C 20 heterocycloalkyl, C1-C 20 alkoxy, C3-C 20 silyl, C6-C 30 arylamino, C6-C 30 arylsilyl, C3-C 30 heteroarylamino, C6-C 30 aryloxy, C3-C 30 heteroaryloxy, C6-C 30 arylthio, C3-C 30 heteroarylthio, C6-C 30 aryl, C3-C 30 heteroaryl, any one or a combination of at least two of them; Any two or more adjacent Rs 1 , R 2 , R 3 , R 4 , R 5 , R 6 may optionally be joined or fused to form a substituted or unsubstituted ring.

2. The metal complex according to claim 1, wherein Ring A is selected from the group consisting of: wherein each R 1 is the same or different and represents mono-substituted, di-substituted or poly-substituted up to saturated substitution, or unsubstituted; W is selected from O, S, NR 5 , PR 5 , R 5 P = O, CR 5 R 6 , SiR 5 R 6 , BR 5 , S = O, SO2, C = O, AsR 5 , R 5 As = O, GeR 5 R 6 ; R 1 , R 5 and R 6 have the same meanings as defined above; Preferably, the metal complex is selected from the group consisting of: Among them, W is selected from O, S, NR 5 , PR 5 , R 5 P = O, CR 5 R 6 , SiR 5 R 6 , BR 5 , S = O, SO2, C = O, AsR 5 , R 5 As = O, GeR 5 R 6 ; Preferably, W is selected from O, S, NR 5 or CR 5 R 6 ; V 2 and V 3 and V 4 and L 1 and L 2 and R 1 to R 6 The definitions of ring A, ring C, ring D and ring E are the same as those in formula (I).

3. The metal complex according to claim 1, wherein The metal complex is selected from the group consisting of: Among them, V 1 to V 4 , L 1 , L 2 , L 3 , R 1 to R 4 , the definitions of ring A and ring C are the same as those in formula (I); X 8 ~X 13 each independently selected from C, O, N, CR 1 , NR 5 ; Y is independently selected from N, P, P═O, CR 9 , SiR 9 or GeR 9 ; Z is independently selected from a single bond, O, S, NR 10 , PR 10 , R 10 P═O, CR 10 R 11 , SiR 10 R 11 , BR 10 , S═O, SO2, C═O, AsR 10 , R 10 As═O, GeR 10 R 11 , or no Z, or a group consisting of the following groups: Wherein, n is selected from 0, 1, 2 or 3; R 7 、R 8 each independently represents mono-substituted, multi-substituted to fully saturated substituted, or unsubstituted; R 7 、R 8 、R 9 、R 10 、R 11 、R 12 each independently selected from hydrogen or a group consisting of deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfide group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted straight-chain alkyl group having C1 to C 40 a substituted or unsubstituted straight-chain or branched heteroakyl group having C1 to C 40 a substituted or unsubstituted branched or cyclic alkyl group having C3 to C 40 a substituted or unsubstituted heterocycloalkyl group having C3 to C 40 a substituted or unsubstituted alkoxy group having C1 to C 40 a substituted or unsubstituted arylalkyl group having C6 to C 60 a substituted or unsubstituted aryloxy group having C6 to C 60 a substituted or unsubstituted arylamino group having C6 to C 60 a substituted or unsubstituted silyl group having C3 to C 40 a substituted or unsubstituted alkenyl group having C2 to C 40 a substituted or unsubstituted cycloalkenyl group having C4 to C 40 a substituted or unsubstituted heteroalkenyl group having C2 to C 40 a substituted or unsubstituted alkynyl group having C6 to C 40 a substituted or unsubstituted aryl group having C6 to C 60 a substituted or unsubstituted arylsilyl group having C6 to C 60 a substituted or unsubstituted heteroaryl group having C2 to C 60 and combinations thereof; R 7 、R 8 、R 9 、R 10 、R 11 、R 12 The substituents substituted in R are selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C 20 alkyl, C1-C 20 heteroalkyl, C2-C 20 alkenyl, C3-C 20 cycloalkyl, C3-C 20 heterocycloalkyl, C1-C 20 alkoxy, C3-C 20 silyl, C6-C 30 arylamino, C6-C 30 arylsilyl, C3-C 30 heteroarylamino, C6-C 30 aryloxy, C3-C 30 heteroaryloxy, C6-C 30 arylthio, C3-C 30 heteroarylthio, C6-C 30 aryl, C3-C 30 heteroaryl; Any two or more adjacent R's 7 's, R 8 's, R 9 's, R 10 's, R 11 's, R 12 may optionally be joined or cyclized to form a substituted or unsubstituted ring.

4. The metal complex according to claim 3, characterized in that, Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 to R A30 、R B1 to R B195 、R C1 to R C80 ; Among them, R A1 ~R A30 The structural formulas are shown as follows: R B1 ~R B195 The structure shown is as follows: R C1 ~R C80 The structure shown is as follows: Each hydrogen atom in each substituent can be replaced by a deuterium atom.

5. The metal complex according to any one of claims 1 to 4, characterized in that, L 1 and L 2 and L 3 each independently selected from a single bond, O, S, S=O, SO2, CR 5 R 6 , C=O or SiR 5 R 6 ; And / or, Y is N; and / or, Z is independently selected from O, S, S=O, SO2, CR 9 R 10 , C=O, SiR 9 R 10 or NR 11 ; and / or, R 5 、R 6 、R 9 、R 10 、R 11 each independently selected from the group consisting of: R A1 ~R A26 、R B1 ~R B185 、R C1 ~R C79 ; and / or, R 1 、R 2 、R 3 、R 4 、R 7 、R 8 each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, isocyano, R A1 ~R A30 、R B1 ~R B195 、R C1 ~R C80 ; R 2 、R 3 、R 4 、R 7 、R 8 each independently represents mono-substituted or polysubstituted to saturated substitution or unsubstituted, and any two or more adjacent substituent groups may optionally be joined or fused to form a substituted or unsubstituted ring.

6. The metal complex according to claim 5, wherein L 1 、L 2 、L 3 are each independently selected from a single bond, O, S or CR 5 R 6 ; and / or, Z is independently selected from O, S, CR 9 R 10 or NR 11 ; and / or, R 5 , R 6 , R 9 , R 10 , R 11 each independently is selected from the group consisting of R A1 , R A10 , R B1 , R C1 ; and / or, R 1 、R 2 、R 3 、R 4 、R 7 、R 8 each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano group, R A1 to R A30 、R B1 to R B195 、R C1 to R C80 ; R 2 、R 3 、R 4 、R 7 、R 8 each independently represents mono-substituted or multi-substituted to saturated substitution or unsubstituted.

7. The metal complex according to any one of claims 1 to 6, characterized in that, The metal complex is selected from the group consisting of: Wherein, some or all of the hydrogen atoms in each structure can be replaced by deuterium atoms.

8. An organic electroluminescent device, which includes an anode, a cathode and at least one organic layer disposed between the anode and the cathode, and the organic layer includes the metal complex according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein, The organic layer includes a host material and a doping material, and the doping material includes the metal complex according to any one of claims 1 to 7; preferably, the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, fluorene, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene and aza-(5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene) or a combination derived from these systems; Preferably, the mass ratio of the host material to the doping material is 99:1 to 1:99, preferably 99:1 to 50:50, and more preferably 98:2 to 90:

10.

10. A consumer product, including the organic electroluminescent device according to any one of claims 8 to 9; Preferably, the consumer product is selected from one of the following products: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a lamp for internal or external lighting and / or signaling, a head-up display, a fully transparent or partially transparent display, a flexible display, a laser printer, a telephone, a cellular phone, a tablet computer, a phablet, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay with a diagonal less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall including a plurality of tiled displays, a theater or stadium screen, a light therapy device and a signboard.

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