Organic electroluminescent material and device thereof

Abstract

Organic electroluminescent materials and devices thereof are disclosed. The organic electroluminescent material is a metal complex containing a La ligand with a structure as shown in a formula 1A and an Lb ligand with a structure as shown in a formula 1B, and the metal complex can obtain a higher sublimation yield during sublimation and has a lower evaporation temperature. When the compound is applied to an electroluminescent device, better device performance can be provided, for example, the service life of the device is prolonged, and the half-peak width is narrower. The invention also discloses an electroluminescent device containing the metal complex and a compound composition containing the metal complex.

Description

[0001] This patent application is a divisional application of Chinese invention patent application No. 202111011390.9, with a priority date of November 18, 2020 and an invention name of “Organic electroluminescent materials and devices thereof”. This application claims priority to Chinese invention patent application No. 202011291606.7 filed on November 18, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound comprising a structure L of Formula 1A a The ligand and L of the formula 1B b The invention relates to a metal complex of a ligand, and an organic electroluminescent device and a compound combination containing the metal complex. Background Art

[0003] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.

[0004] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0005] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0006] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0007] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.

[0008] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.

[0009] Cyano substitution is not often introduced into phosphorescent metal complexes, such as iridium complexes. US20140252333A1 discloses a series of cyano-phenyl substituted iridium complexes, but the results do not clearly indicate the effect brought by the cyano group. In addition, because the cyano group is a very electron-withdrawing substituent, it is also used to blue-shift the emission spectrum of phosphorescent metal complexes, such as US20040121184A1. The applicant's previous application US20200251666A1 discloses metal complexes with cyano-substituted ligands, which can be used in organic electroluminescent devices to improve device performance and color saturation. Although it has reached a relatively high level in the industry, there is still room for improvement.

[0010] Alkyl substitution is often introduced into phosphorescent metal complexes, such as iridium complexes, to produce red emission colors. US2014231755A1 found that deuterated methyl groups at the 5-position in 2-phenylpyridine can improve the lifetime of the device. Summary of the invention

[0011] The present invention aims to provide a series of L comprising the structure of formula 1A a The ligand and L of the formula 1B b The metal complexes of the ligands can solve at least part of the above problems. The metal complexes can be used as luminescent materials in electroluminescent devices. These novel compounds can obtain higher sublimation yields during sublimation and have lower evaporation temperatures. Application in electroluminescent devices can provide better device performance, such as improved device life and narrower half-peak width.

[0012] According to one embodiment of the present invention, a metal complex is disclosed, which has M(L a ) m (L b ) n (L c ) q The general formula of

[0013] in,

[0014] L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand;

[0015] The metal M is selected from metals with a relative atomic mass greater than 40; preferably, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, the same or different; more preferably, M is selected from Pt or Ir at each occurrence, the same or different;

[0016] m is 1 or 2, n is 1 or 2, q is 0 or 1, m+n+q equals the oxidation state of M; when m is 2, the two L a are the same or different; when n is 2, the two L b are the same or different;

[0017] L a Each occurrence has the same or different structure represented by Formula 1A; L b Each occurrence identically or differently has a structure represented by Formula 1B;

[0018]

[0019] in,

[0020] Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different;

[0021] Each occurrence of X1-X8 is selected from C or CR x ;

[0022] Each occurrence of Y1-Y4 is the same or different selection from CR y or N;

[0023] Each occurrence of U1-U4 is the same or different from CR u or N;

[0024] Each occurrence of W1-W4 is the same or different selection from CR w or N;

[0025] R, R x , R y , R u , R wEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0026] At least one or more of U1–U4 is selected from CR u And the R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4;

[0027] R x At least one of them is a cyano group;

[0028] Adjacent substituents R, R x , R y , R u , R w can optionally be linked to form a ring;

[0029] Among them, L c Each occurrence is identically or differently selected from any one of the following groups:

[0030]

[0031] in,

[0032] R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0033] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 RC2 ;

[0034] R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0035] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0036] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0037] anode,

[0038] cathode,

[0039] and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex described in the above embodiment.

[0040] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises the metal complex described in the above embodiment.

[0041] The present invention discloses a series of L comprising the structure of formula 1A a The ligand and L of the formula 1B b The metal complex of the ligand is a The introduction of specific substituents in the ligand and the bBy introducing cyano groups into the ligands, these new compounds can obtain higher sublimation yields and lower evaporation temperatures during sublimation. These metal complexes can be used as luminescent materials in electroluminescent devices. Application in electroluminescent devices can provide better device performance, such as improved device life and narrower half-peak width. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound combinations disclosed herein.

[0043] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the metal complex and compound combination disclosed herein. DETAILED DESCRIPTION

[0044] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0045] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0046] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0047] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0048] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0049] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0050] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0051] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0052] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0053] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0054] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0055] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0056] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0057] Definition of Substituent Terms

[0058] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0059] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0060] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0061] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0062] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0063] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.

[0064] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0065] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0066] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0067] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0068] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0069] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0070] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0071] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0072] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0073] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be replaced by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted The alkylene group may be substituted with a cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof.

[0074] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0075] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0076] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0077] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0078] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0079]

[0080] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0081]

[0082] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0083]

[0084] According to one embodiment of the present invention, a metal complex is disclosed, which has M(L a ) m (L b ) n (L c ) q The general formula of

[0085] in,

[0086] L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand; for example, L a , L b and L c Any two of can be connected to form a tetradentate ligand; for example, L a , L b and L c can be connected to each other to form a hexadentate ligand; or for example, L a , L b , L c None of them are connected so as not to form a multidentate ligand;

[0087] The metal M is selected from metals with a relative atomic mass greater than 40; preferably, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence, the same or different; more preferably, M is selected from Pt or Ir at each occurrence, the same or different;

[0088] m is 1 or 2, n is 1 or 2, q is 0 or 1, m+n+q equals the oxidation state of M; when m is 2, the two L a are the same or different; when n is 2, the two L b are the same or different;

[0089] L a Each occurrence has the same or different structure represented by Formula 1A; L b Each occurrence identically or differently has a structure represented by Formula 1B;

[0090]

[0091] in,

[0092] Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different;

[0093] Each occurrence of X1-X8 is selected from C or CR x ;

[0094] Each occurrence of Y1-Y4 is the same or different selection from CR y or N;

[0095] Each occurrence of U1-U4 is the same or different from CR u or N;

[0096] Each occurrence of W1-W4 is the same or different selection from CR w or N;

[0097] R, R x , R y , R u , R w Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0098] At least one or more of U1–U4 is selected from CR u And the R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4;

[0099] R x At least one of them is a cyano group;

[0100] Adjacent substituents R, R x , R y, R u , R w can optionally be linked to form a ring;

[0101] Among them, L c Each occurrence is identically or differently selected from any one of the following groups:

[0102]

[0103]

[0104] in,

[0105] R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0106] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ;

[0107] R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0108] Adjacent substituent R a , R b , R c , R N1 , RC1 and R C2 Can optionally be linked to form a ring.

[0109] In this article, “all the R u The sum of the number of carbon atoms in the molecule is at least 4” means that the following conditions are met: “One or more of U1–U4 is selected from CR u , and the R u All R of "is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof" u The total number of carbon atoms is greater than or equal to 4. When one of U1-U4 satisfies the above conditions, the number of carbon atoms of the substituent is greater than or equal to 4; when two of U1-U4 satisfy the above conditions, the total number of carbon atoms of the two substituents is greater than or equal to 4; when three of U1-U4 satisfy the above conditions, the total number of carbon atoms of the three substituents is greater than or equal to 4; when four of U1-U4 satisfy the above conditions, the total number of carbon atoms of the four substituents is greater than or equal to 4. For example, when U2 is selected from CR u And the above conditions are met, then the substituent R of U2 u The number of carbon atoms is greater than or equal to 4; when U3 is selected from CR u And the above conditions are met, then the substituent R of U3 u The number of carbon atoms is greater than or equal to 4; and so on for other cases.

[0110] In this embodiment, "the adjacent substituents R, R x , R y , R u , R w "can be optionally linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R x Between the two substituents R y Between the two substituents R u Between the two substituents R w Between the two substituents R w and R u Between the two substituents R y and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0111] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2"can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0112] According to one embodiment of the present invention, L b Having a structure represented by formula 1Ba-1Bd:

[0113]

[0114] Z is selected from the group consisting of O, S, Se, NR, CRRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different;

[0115] In formula 1Ba, X3-X8 are selected from CR x ;

[0116] In Formula 1Bb, X1 and X4-X8 are selected from CR x ;

[0117] In Formula 1Bc and Formula 1Bd, X1-X2 and X5-X8 are selected from CR x ;

[0118] Each occurrence of Y1-Y4 is the same or different selection from CR y or N;

[0119] R, R x , Ry , each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0120] Adjacent substituents R, R x , R y Can optionally be linked to form a ring.

[0121] In this embodiment, "the adjacent substituents R, R x , R y "can be optionally linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R x Between the two substituents R y Between the two substituents R y and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0122] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 2:

[0123]

[0124] in,

[0125] m is selected from 1 or 2; when m=1, the two L b are the same or different; when m=2, the two L a are the same or different;

[0126] Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different;

[0127] Each occurrence of X3-X8 is the same or different selection from CR x ;

[0128] Each occurrence of Y1-Y4 is the same or different selection from CR y or N;

[0129] Each occurrence of U1-U4 is the same or different from CR u or N;

[0130] Each occurrence of W1-W4 is the same or different selection from CR w or N;

[0131] R, R x , R y , R u , R w Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0132] A substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4;

[0133] R x At least one of them is a cyano group;

[0134] Adjacent substituents R, R x , R y , R u Can optionally be linked to form a ring.

[0135] In this embodiment, "the adjacent substituents R, R x , Ry , R u "can be optionally linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R x Between the two substituents R y Between the two substituents R u Between the two substituents R y and R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0136] According to one embodiment of the present invention, Z is selected from O and S.

[0137] According to one embodiment of the present invention, Z is O.

[0138] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R x is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0139] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R xSelected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof.

[0140] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R x Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0141] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R x Selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and a combination thereof.

[0142] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R x is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0143] According to one embodiment of the present invention, wherein the R x One of them is cyano and at least one other R x Selected from the group consisting of fluorine, deuterium, methyl, deuterated methyl, deuterated isopropyl, cyclohexyl, deuterated cyclohexyl, phenyl, deuterated phenyl, methylphenyl, deuterated methylphenyl.

[0144] According to one embodiment of the present invention, the CR of X5-X8 x At least one of them is CR x , and the R x It's cyano.

[0145] According to one embodiment of the present invention, the CR of X7-X8 x At least one of them is CR x , and the R x It is cyano;

[0146] According to one embodiment of the present invention, X7 is CR x , and the R x It's cyano.

[0147] According to one embodiment of the present invention, X8 is CR x , and the R x It's cyano.

[0148] According to an embodiment of the present invention, each time U1-U4 appears, the same or different CR u , R u At least one of the R is selected from a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4.

[0149] According to one embodiment of the present invention, each time U1-U4 appears, it is selected from N or CR in the same or different manner. u , and at least one of them is CR u , and at least one of them is CR u , R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and said R u The total number of carbon atoms is at least 4.

[0150] According to one embodiment of the present invention, R u At least one of them is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof.

[0151] According to one embodiment of the present invention, R u At least one of the following substituents is selected from the group consisting of substituted or unsubstituted substituents:

[0152] and combinations thereof; optionally, the hydrogen in the above groups is partially or completely deuterated;

[0153] Wherein "*" indicates the connection position of the substituent to the carbon.

[0154] According to one embodiment of the present invention, R u At least one of them is selected from a substituted or unsubstituted alkyl group having 4 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 6 carbon atoms, or a combination thereof.

[0155] According to one embodiment of the present invention, U2 or U3 is CRu , and the R u It is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof.

[0156] According to one embodiment of the present invention, U2 or U3 is CR u , R u Each occurrence may be the same or different, the R u It is selected from a substituted or unsubstituted alkyl group having 4 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 6 carbon atoms, or a combination thereof.

[0157] According to one embodiment of the present invention, U2 and U3 are CR u , and the R u Each occurrence is identically or differently selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof, and wherein at least one R u The substituent has 4 or more carbon atoms.

[0158] According to one embodiment of the present invention, U1 and U4 are CR u , R u is selected from the group consisting of hydrogen, deuterium, methyl and deuterated methyl.

[0159] According to one embodiment of the present invention, each time W1-W4 appears, the same or different CR w , Y1-Y4 are CR each time they appear, either identically or differently y , R w and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0160] According to one embodiment of the present invention, R w and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 ring carbon atoms, substituted or unsubstituted aryl having 6-10 carbon atoms, and combinations thereof.

[0161] According to one embodiment of the present invention, R w and R yEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

[0162] According to one embodiment of the present invention, each time W1-W4 appears, the same or different CR w , at least one R is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; and / or Y1-Y4 are identically or differently CR at each occurrence y , at least one R y is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0163] According to one embodiment of the present invention, R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0164] According to one embodiment of the present invention, R is selected from methyl or deuterated methyl.

[0165] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 -L a206 The group consisting of L a1 -L a206 The specific structure is shown in claim 17.

[0166] According to one embodiment of the present invention, L b Each time it appears, choose the same or different one from L b1 -L b972 The group consisting of L b1 -L b972 The specific structure is shown in claim 18.

[0167] According to one embodiment of the present invention, the metal complex has Ir(L a )2L b The structure of two L a Same; L a Selected from L a1 -La206 The group consisting of L a1 -L a206 The specific structure is shown in claim 17; L b Selected from L b1 -L b972 The group consisting of L b1 -L b972 The specific structure is shown in claim 18.

[0168] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 448, wherein the specific structures of metal complex 1 to metal complex 448 are shown in claim 19.

[0169] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex described in any of the aforementioned embodiments.

[0170] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

[0171] According to an embodiment of the present invention, the light-emitting layer in the electroluminescent device emits green light.

[0172] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device further comprises at least one first host compound.

[0173] According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device further comprises at least one first host compound and at least one second host compound.

[0174] According to one embodiment of the present invention, at least one of the main compounds in the electroluminescent device contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0175] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 3:

[0176]

[0177] in,

[0178] L xEach occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0179] Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect;

[0180] Each occurrence of T is selected from C, CR t or N, and at least one of T is C, and L x connect;

[0181] R v and R t Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0182] Ar1 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0183] Adjacent substituent R v and R t Can optionally be linked to form a ring.

[0184] In this embodiment, "the adjacent substituent R v and R t "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R v Between the two substituents R tBetween the two substituents R v and R t Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0185] According to one embodiment of the present invention, the second host compound has a structure represented by one of Formula 3-a to Formula 3-j:

[0186]

[0187]

[0188] in,

[0189] L x Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0190] Each time V appears, it is selected from CR in the same or different way. v or N, and at least one of V is C, and L x connect;

[0191] Each occurrence of T is selected from CR t or N, and at least one of T is C, and L x connect;

[0192] R v and R t Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0193] Ar1 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0194] Adjacent substituent R v and R t Can optionally be linked to form a ring.

[0195] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0196] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

[0197] According to another embodiment of the present invention, a compound combination is also disclosed, which includes a metal complex, and the specific structure of the metal complex is shown in any of the above embodiments.

[0198] Combination with other materials

[0199] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0200] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0201] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0202] Material synthesis example:

[0203] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0204] Synthesis Example 1: Synthesis of Metal Complex 13

[0205]

[0206] In a dry 250mL round-bottom flask, intermediate 1 (1.6g, 4.6mmol), iridium complex 1 (3.18g, 3.8mmol), 2-ethoxyethanol (30mL) and DMF (30mL) were added in sequence, and the reaction was heated at 90°C for 144h under N2 protection. After the reaction was cooled, it was filtered through diatomaceous earth. Methanol and n-hexane were washed twice respectively, and the yellow solid on the diatomaceous earth was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 13 (0.82g, 22.3% yield). The product was determined to be the target product with a molecular weight of 958.3.

[0207] Synthesis Example 2: Synthesis of Metal Complex 7

[0208]

[0209] In a dry 250mL round-bottom flask, add intermediate 2 (1.0g, 2.9mmol), iridium complex 1 (2.2g, 2.6mmol), 2-ethoxyethanol (40mL) and DMF (40mL) in sequence, and heat the reaction at 100°C for 120h under N2 protection. After the reaction is cooled, filter it with diatomaceous earth. Wash it with methanol and n-hexane twice respectively, dissolve the yellow solid on the diatomaceous earth with dichloromethane, collect the organic phase, concentrate under reduced pressure, and purify it by column chromatography to obtain yellow solid metal complex 7 (0.45g, 18.1% yield). The product is determined to be the target product with a molecular weight of 958.3.

[0210] Synthesis Example 3: Synthesis of Metal Complex 17

[0211]

[0212] In a dry 250mL round-bottom flask, intermediate 2 (1.2g, 4.5mmol), iridium complex 1 (2.5g, 3.0mmol), 2-ethoxyethanol (30mL) and DMF (30mL) were added in sequence. Under N2 protection, the reaction was heated at 90°C for 144h. After the reaction was cooled, it was filtered through diatomaceous earth. Methanol and n-hexane were washed twice respectively. The yellow solid on the diatomaceous earth was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 17 (0.73g, 25.3% yield). The product was determined to be the target product with a molecular weight of 963.3.

[0213] Synthesis Example 4: Synthesis of Metal Complex 163

[0214]

[0215] In a dry 250 mL round-bottom flask, intermediate 1 (1.3 g, 3.7 mmol), iridium complex 2 (2.2 g, 2.6 mmol), 2-ethoxyethanol (30 mL) and DMF (30 mL) were added in sequence. Under N2 protection, the reaction was heated at 90 ° C for 144 h. After the reaction was cooled, it was filtered through diatomaceous earth. Methanol and n-hexane were washed twice respectively. The yellow solid on the diatomaceous earth was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 163 (0.78 g, 30.4% yield). The product was determined to be the target product with a molecular weight of 986.3.

[0216] Synthesis Example 5: Synthesis of Metal Complex 43

[0217]

[0218] In a dry 250mL round-bottom flask, intermediate 1 (1.5g, 4.9mmol), iridium complex 3 (3.0g, 3.6mmol), 2-ethoxyethanol (30mL) and DMF (30mL) were added in sequence, and the reaction was heated at 95°C for 144h under N2 protection. After the reaction was cooled, it was filtered through diatomaceous earth. Methanol and n-hexane were washed twice respectively, and the yellow solid on the diatomaceous earth was dissolved with dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 43 (1.23g, 35.4% yield). The product structure was determined to be the target product, and the molecular weight was 964.4.

[0219] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0220] Device Example 1

[0221] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 In the case of 1000 Å / s, the ITO anode is sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound H1 is used as an electron blocking layer (EBL). Then the metal complex 13 of the present invention is doped in compound H1 and compound H2 and co-deposited as a light-emitting layer (EML). On the EML, compound H2 is used as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0222] Device Example 3

[0223] The implementation of Device Example 3 is the same as that of Device Example 1, except that the compound metal complex 17 is used instead of the inventive metal complex 13 in the light emitting layer (EML).

[0224] Device Comparison Example 1

[0225] The device comparative example 1 is implemented in the same manner as the device example 1, except that the compound GD1 is used in place of the inventive metal complex 13 in the light emitting layer (EML).

[0226] Device Comparison Example 2

[0227] The device comparative example 2 is implemented in the same manner as the device example 1, except that the compound GD2 is used in place of the metal complex 13 of the present invention in the light emitting layer (EML).

[0228] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0229] Table 1 Device structures of Example 1 and Comparative Examples 1-2

[0230]

[0231] The material structure used in the device is shown below:

[0232]

[0233]

[0234] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM). The evaporation temperature (Sub T) of the material is about 10 -8 The temperature is obtained by thermal vacuum evaporation of metal complexes at a rate of 0.2 angstroms / second under the condition of 1000 torr. The life (LT97) data is obtained at 80mA / cm 2 The test was performed at a constant current. These data are recorded and shown in Table 2.

[0235] Table 2 Device data of Example 1 and Example 3 and Comparative Examples 1-2

[0236]

[0237] From the data in Table 2, it can be seen that the half-peak width of Example 1 is narrower by 3.3nm than that of Comparative Example 1 and by 3.0nm than that of Comparative Example 2. At the same time, the evaporation temperature of the device Example 1 is nearly 33°C lower than that of Comparative Example 1 and nearly 29°C lower than that of Comparative Example 2. The lower evaporation temperature is conducive to the stability of the inventive complex during the evaporation process, and the low evaporation temperature is conducive to the industrial application of the material and can reduce energy consumption. In addition, the life of Example 1 is increased by 51.5% compared with Comparative Example 1; the life of the device Example 1 is also increased by 15.4% compared with Comparative Example 2. Similarly, Example 3 applies metal complex 17 to the device. Compared with Comparative Examples 1 and 2, the half-peak width of Example 3 is narrower by 4.6nm and 4.3nm, respectively, and the evaporation temperature is reduced by nearly 40°C and 37°C, respectively. At the same time, the device life is increased by 88.5% and 43.6%, respectively, that is, it has a narrower half-peak width, a lower evaporation temperature, and a greatly improved excellent device life, and the comprehensive performance of the device is greatly improved.

[0238] The metal complex 13 used in Example 1 and the metal complexes GD1 and GD2 used in Comparative Examples 1 and 2 have the same ligand L b , just L a The substituents on the ligands are different. In the examples, L having specific substituents is used. a Compared with the control examples without substitution or with only methyl substitution, the ligand has a narrower half-peak width, a lower evaporation temperature, and a better device life. The metal complex 17 used in Example 3 is further b The deuterium substitution on the ligand further improves the various performances of the device, ultimately achieving an improvement in the overall performance of the device.

[0239] Device Example 2

[0240] Device Example 2 was carried out in the same manner as Device Example 1, except that the metal complex 7 was used in place of the inventive metal complex 13 in the light emitting layer (EML).

[0241] Device Comparison Example 3

[0242] The device comparative example 3 is implemented in the same manner as the device example 1, except that the compound GD3 is used in place of the metal complex 13 of the present invention in the light emitting layer (EML).

[0243] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0244] Table 3 Device structures of Example 2 and Comparative Example 3

[0245]

[0246] The new material structure used in the device is shown below:

[0247]

[0248] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM). The evaporation temperature (Sub T) of the material is about 10 -8 The temperature is obtained by thermal vacuum evaporation of metal complexes at a rate of 0.2 angstroms / second under the condition of 1000 torr. The lifespan (LT97) data is obtained at 80 mA / cm 2 The test was performed at a constant current. These data are recorded and shown in Table 4.

[0249] Table 4 Device data of Example 2 and Comparative Example 3

[0250]

[0251] From the data in Table 4, it can be seen that the half-peak width of device Example 2 is 2.3 nm narrower than that of device Comparative Example 3, and the evaporation temperature is nearly 26°C lower than that of Comparative Example 3. In addition, the life of Example 2 is increased by 16.4% compared with Comparative Example 3. The metal complex 7 used in Example 2 and the metal complex GD3 used in Comparative Example 3 have the same ligand L b , just L a Due to the difference in the substituents on the ligands, Example 2 has a narrower half-peak width, a lower evaporation temperature, and a better device life than Comparative Example 3, which once again proves the excellent effect of the present invention.

[0252] Sublimation Data

[0253] The metal complexes of the present invention and the comparative compounds were sublimated using a BOF-A1-3-60 sublimator produced by Anhui Beiyike Equipment Co., Ltd. The metal complexes 13, 17, 7 and the reference complexes GD1, GD2 and GD3 of the present invention were placed in the sublimation tube of the sublimator, and the vacuum degree of the sublimation tube was reduced to 9.9×10 -4 Pa below, heated to 300 ℃ ~ 370 ℃, stably sublimated to obtain metal complexes. The data of sublimation yield of these materials are recorded and shown in Table 5. Among them, the sublimation yield is the ratio of the mass after sublimation to the mass before sublimation.

[0254] Table 5 Sublimation data

[0255] Compound No. Sublimation yield (%) Metal complex 13 85.3 Metal complex 17 88.8 Metal complex 7 71.1 Compound GD1 32.5 Compound GD2 58.9 Compound GD3 48.8

[0256] From the data in Table 5, it can be seen that: a The metal complexes 13 and 17 with specific substitutions on the ligands showed excellent sublimation performance, with sublimation yields of 85.3% and 88.8%, respectively, which were nearly 1.6 and 1.7 times higher than the sublimation yield of the reference compound GD1 (32.8%). Similarly, the sublimation yields of the reference compound GD2 (58.9%) increased by 44.8% and 50.7%, respectively. In addition, the sublimation yield of the metal complex 7 reached 71.1%, which was 45.6% higher than the sublimation yield of the reference compound GD3 (48.8%). The results show that the sublimation yield of the metal complex 7 disclosed in the present invention in L a Metal complexes with specific (cyclo)alkyl substitutions introduced into the ligand structure have a higher sublimation yield than metal complexes without such specific substitutions. The substantial increase in sublimation yield is unexpected, and the increase in sublimation yield is of great significance for the industrial mass production of metal complexes.

[0257] Device Example 4

[0258] The implementation of Device Example 4 is the same as that of Device Example 1, except that Compound H3 is used instead of Compound H2 in the light emitting layer (EML), and the ratio in the light emitting layer is Compound H1: Compound H3: Metal complex 13 = 63:31:6.

[0259] Device Comparison Example 4

[0260] The device comparative example 4 is implemented in the same manner as the device example 4, except that the compound GD2 is used in place of the inventive metal complex 13 in the light emitting layer (EML).

[0261] Device Comparison Example 5

[0262] The device comparative example 5 is implemented in the same manner as the device example 4, except that the compound GD4 is used in place of the inventive metal complex 13 in the light emitting layer (EML).

[0263] Device Comparison Example 6

[0264] The device comparative example 6 is implemented in the same manner as the device example 4, except that the compound GD5 is used in place of the inventive metal complex 13 in the light emitting layer (EML).

[0265] Device Comparison Example 7

[0266] The device comparative example 7 is implemented in the same manner as the device example 4, except that the compound GD6 is used in place of the metal complex 13 of the present invention in the light emitting layer (EML).

[0267] The detailed device layer structure and thickness are shown in Table 6. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0268] Table 6 Device structures of Example 4 and Comparative Examples 4-7

[0269]

[0270]

[0271] The new material structure used in the device is shown below:

[0272]

[0273] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM). Lifespan (LT95) is when the initial luminous brightness is 10000cd / m 2 The time required to decay to 95% of the initial value is recorded and shown in Table 7.

[0274] Table 7 Device data of Example 4 and Comparative Examples 4-7

[0275]

[0276] From the data in Table 7, we can see that at 10000cd / m 2 The life of Example 4 reaches 1159h, which is significantly improved compared with Comparative Examples 4 to 7. a Comparative Example 4, in which there is no specific substituent on the ligand, increased by 39.8%, compared with L b The comparative examples 5 and 7 without cyano substitution on the ligand increased by 15.8% and 23.3%, respectively, compared with L a and L b The comparative example 6 without any specific substituents has increased by 27.4%. In addition, the half-peak width of the embodiment 4 is only 37.5 nm, which is much lower than the 59 nm of the comparative examples 5 and 7, which is very rare in green phosphorescent devices.

[0277] When L b When the ligand has no cyano substituent, L a Comparative Example 5 with specific substitution on the ligand relative to L a The device life of Comparative Example 6 without specific substitution on the ligand was only improved by 10%; b When the ligand has a cyano substituent, L a Example 4 with specific substitution on the ligand relative to La The device life of Comparative Example 4 without specific substitution on the ligand was improved by 39.8%. a In the case of L b Example 4 in which the ligand has a cyano group substitution is compared to L b The device lifetime of Comparative Example 5, in which the ligand is not substituted with a cyano group, is increased by 15.8%, while b The device life of Comparative Example 7 with fluorine substitution on the ligand is slightly reduced compared with Comparative Example 5. The above results all show that the device life of the device of the present invention containing L with specific substitution is slightly reduced compared with Comparative Example 5. a Ligand and L having cyano group substitution b The metal complex of the ligand can achieve excellent device performance, especially significantly improve the device life.

[0278] In summary, the present invention comprises a specific substitution L a and L b The metal complex of the ligand can be used as a luminescent material in the luminescent layer of an electroluminescent device. When it is used in combination with a host material of different structures, excellent device performance can be achieved. a and L b The metal complex of the ligand can maintain the half-peak width of the relevant device at a high level in the industry, and can also significantly improve the life of the device. In addition, the metal complex of the present invention also has great improvements in sublimation yield and evaporation temperature, and has great advantages and broad prospects in industrial applications.

[0279] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A metal complex having M(L a ) m (L b ) n (L c ) q The general formula of in, L a , L b and L c are the first, second and third ligands coordinated to the metal M, and L c and the L a or L b are the same or different; where L a , L b and L c can optionally be linked to form a multidentate ligand; The metal M is selected from metals with a relative atomic mass greater than 40; preferably, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt at each occurrence; more preferably, M is selected from Pt or Ir at each occurrence at the same or different times; m is 1 or 2, n is 1 or 2, q is 0 or 1, m+n+q equals the oxidation state of M; when m is 2, the two L a are the same or different; when n is 2, the two L b are the same or different; L a Each occurrence has the same or different structure represented by Formula 1A; L b Each occurrence identically or differently has a structure represented by Formula 1B; in, Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different; Each occurrence of X1-X8 is selected from C or CR x ; Each occurrence of Y1-Y4 is the same or different selection from CR y or N; Each occurrence of U1-U4 is the same or different from CR u or N; Each occurrence of W1-W4 is the same or different selection from CR w or N; R, R x , R y , R u , R w The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof; At least one or more of U1–U4 is selected from CR u And the R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4; R x At least one of them is a cyano group; Adjacent substituents R, R x , R y , R u , R w can optionally be linked to form a ring; Among them, L c Each occurrence is identically or differently selected from any one of the following groups: in, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 , CR C1 R C2 ; R a , R b , R c , R N1 , R C1 and R C2 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof; Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

2. The metal complex according to claim 1, wherein L b Having a structure represented by formula 1Ba-1Bd: in, Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different; Each occurrence of X1-X8 is the same or different selection from CR x ; Each occurrence of Y1-Y4 is the same or different selection from CR y or N; R, R x , R y The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof; Adjacent substituents R, R x , R y Can optionally be linked to form a ring.

3. The metal complex according to claim 1, wherein The metal complex has a structure represented by Formula 2: in, m is selected from 1 or 2; when m=1, the two L b are the same or different; when m=2, the two L a are the same or different; Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when two Rs are present at the same time, the two Rs are the same or different; Each occurrence of X3-X8 is the same or different selection from CR x ; Each occurrence of Y1-Y4 is the same or different selection from CR y or N; Each occurrence of U1-U4 is the same or different from CR u or N; Each occurrence of W1-W4 is the same or different selection from CR w or N; R, R x , R y , R u , R w The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof; At least one or more of U1–U4 is selected from CR u And the R u is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof; and all of said R u The sum of the number of carbon atoms is at least 4; R x At least one of them is a cyano group; Adjacent substituents R, R x , R y , R u Can optionally be linked to form a ring.

4. The metal complex according to any one of claims 1 to 3, wherein Z is selected from O and S; Preferably, Z is O.

5. The metal complex according to any one of claims 1 to 4, wherein The R x One of them is cyano and at least one other R x selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 3 substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; Preferably, R x One of them is cyano and at least one other R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof; More preferably, R x One of them is cyano and at least one other R x Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

6. The metal complex according to any one of claims 1 to 5, wherein R x One of them is cyano and at least one other R x is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and a combination thereof.

7. The metal complex according to any one of claims 1 to 5, wherein R x One of them is cyano and at least one other R x is selected from the group consisting of fluorine, deuterium, methyl, deuterated methyl, deuterated isopropyl, cyclohexyl, deuterated cyclohexyl, phenyl, deuterated phenyl, methylphenyl, deuterated methylphenyl.

8. The metal complex according to any one of claims 1 to 7, wherein CR of X5-X8 x At least one R x It is cyano; Preferably, X7 is CRx, and the R x is cyano; or X8 is CR x , and the R x It's cyano.

9. The metal complex according to any one of claims 1 to 8, wherein U1-U4 is CR each time it appears, either identically or differently u , R u At least one of the R is selected from a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The total number of carbon atoms is at least 4.

10. The metal complex according to any one of claims 1 to 8, wherein Each occurrence of U1-U4 is the same or different selection from N or CR u , and at least one of them is CR u , and R u is selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the number of carbon atoms is at least 4.

11. The metal complex according to any one of claims 1 to 10, wherein R u At least one of them is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof; Preferably, R u At least one of the following substituents is selected from the group consisting of substituted or unsubstituted substituents: and combinations thereof; optionally, the hydrogen in the above groups is partially or completely deuterated; Wherein "*" indicates the connection position of the substituent to the carbon.

12. The metal complex according to any one of claims 1 to 11, wherein U2 or U3 is CR u , and the R u is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof; Preferably, R u It is selected from a substituted or unsubstituted alkyl group having 4 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 6 carbon atoms, or a combination thereof.

13. The metal complex according to any one of claims 1 to 11, wherein U2 and U3 are CR u , and the R u Each occurrence is identically or differently selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof, and wherein at least one R u The substituent has 4 or more carbon atoms.

14. The metal complex according to claim 13, wherein U1 and U4 are CR u , R u is selected from the group consisting of hydrogen, deuterium, methyl and deuterated methyl.

15. The metal complex according to any one of claims 1 to 14, wherein W1-W4 is CR each time it appears, either identically or differently w , Y1-Y4 are CR each time they appear, either identically or differently y , R w and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; Preferably, R w and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 10 carbon atoms, and combinations thereof; More preferably, R w and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

16. The metal complex according to any one of claims 1 to 14, wherein W1-W4 is CR each time it appears, either identically or differently w , at least one R w is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; and / or Y1-Y4 are CR for each occurrence, the same or different y , at least one R y is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

17. The metal complex according to claim 1, wherein L a Each occurrence is identically or differently selected from the group consisting of:

18. The metal complex according to claim 1, wherein L b Each occurrence is identically or differently selected from the group consisting of:

19. The metal complex according to claim 1 or 3, wherein The metal complex has Ir(L a )2L b The structure of two L a Same; L a Selected from L a1 -L a206 The group composed of L b Selected from L b1 -L b972 The group composed of; Preferably, the metal complex is selected from the group consisting of metal complexes 1 to 448, wherein metal complexes 1 to 448 have Ir(L a )2L b The structure of two L a Same, L a and L b They correspond to the structures shown in the following table: 。 20. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers comprises the metal complex according to any one of claims 1 to 19.

21. The electroluminescent device of claim 20, wherein: The organic layer including the metal complex is a light-emitting layer.

22. The electroluminescent device of claim 21, wherein: The light-emitting layer emits green light.

23. The electroluminescent device of claim 21, wherein: The light-emitting layer further comprises at least one first host compound; Preferably, the light-emitting layer further comprises at least two host compounds; More preferably, at least one of the host compounds comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

24. The electroluminescent device of claim 23, wherein: The first host compound has a structure represented by Formula 3: in, L x Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Each occurrence of V is selected from C, CR v or N, and at least one of V is C, and L x connect; Each occurrence of T is selected from C, CR t or N, and at least one of T is C, and L x connect; R v and R t Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ar1 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R v and R t can optionally be linked to form a ring; Preferably, the second host compound has a structure represented by one of Formula 3-a to Formula 3-j:

25. The electroluminescent device of claim 23, wherein: The metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer; Preferably, the weight of the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.

26. A compound combination comprising the metal complex according to any one of claims 1 to 19.

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