CN115710290A - Organic electroluminescent material and device thereof - Google Patents

Abstract

Organic electroluminescent materials and devices thereof are disclosed. The organic electroluminescent material is a metal complex containing the L _a ligand of the formula 1 structure. These novel compounds can be used in electroluminescent devices to obtain very excellent device performance, such as the reduction of device voltage, current efficiency, The improvement of power efficiency and external quantum efficiency can comprehensively improve the performance of all aspects of the device, and finally obtain a great improvement in the overall performance of the device. An organic electroluminescent device comprising the metal complex and a composition comprising the metal complex are also disclosed.

Description

Organic Electroluminescent Materials and Devices

technical field

The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a metal complex comprising the L _a ligand of formula 1, an organic electroluminescent device comprising the metal complex and a composition comprising the metal complex.

Background technique

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.

In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport layer and emitted light Layer (Applied Physics Letters, 1987, 51(12):913-915). Once the device is biased, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art 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 anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, can make them well suited for specialized applications, such as on flexible substrates.

OLEDs can be classified into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only emits light using a singlet state. The triplet state 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 hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs using triplet emission from complex-containing heavy metals 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 the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, leading to high IQE.

OLEDs can also be classified into small molecule and polymer OLEDs according to the form of materials used. Small molecule refers to any organic or organometallic material that is not a polymer. Small molecules can have very large molecular weights as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers with pendant emitting groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during fabrication.

There are various OLED manufacturing methods. Small molecule OLEDs are usually fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution methods such as spin coating, inkjet printing, and nozzle printing. Small-molecule OLEDs can also be fabricated by solution methods if the materials can be dissolved or dispersed in solvents.

The luminescent color of OLED can be realized through the structure design of luminescent material. OLEDs can include one light emitting layer or multiple light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from blue unsaturation, short device lifetime and high operating voltage. Commercial full-color OLED displays typically use a hybrid strategy, using blue phosphor and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, more saturated emission spectra, higher efficiencies and longer device lifetimes are expected.

其中R₁-R₄选自氢、氘、烷基、环烷基、芳基、杂芳基，及其组合。在该申请中仅公开了R₁为苯基的芳基取代基的金属配合物及其在器件中的应用，未公开和教导具有如本申请特定的取代基的金属络合物及其对器件性能的影响。US2013119354A1 discloses a metal complex with the following general structure:

Wherein R ₁ -R ₄ are selected from hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. Only disclosed in this application _R Be the metal complex of the aryl substituent of phenyl and its application in the device, do not disclose and teach the metal complex with the specific substituent of the present application and its application to the device performance impact.

在该申请中公开了芳胺取代的芴类配体的金属配合物及其在器件中的应用。该申请公开的具有多芳胺取代的芴基配体在金属络合物中的应用。未公开和教导具有如本申请包含具有特定的取代基的特定骨架结构配体的金属络合物及其对器件性能的影响。CN107236006A discloses a red light metal complex with the following general structure:

In this application metal complexes of arylamine substituted fluorene ligands and their use in devices are disclosed. The application discloses the application of polyarylamine-substituted fluorenyl ligands in metal complexes. Metal complexes with specific framework ligands with specific substituents and their effects on device performance are not disclosed and taught.

在该申请中公开了含有咔唑取代基的含二酮配体的红光金属络合物及其在有机电致发光器件中的应用。该申请公开的是苯基喹啉上具有咔唑取代基，且和二酮配体配位的金属络合物。未公开和教导具有如本申请包含具有特定的取代基的特定骨架结构配体的金属络合物及其对器件性能的影响。CN101108964A discloses a red light metal complex with the following general structure:

In this application are disclosed red light metal complexes containing diketone ligands containing carbazole substituents and their use in organic electroluminescent devices. The application discloses a metal complex having a carbazole substituent on the phenylquinoline and coordinating with a diketone ligand. Metal complexes with specific framework ligands with specific substituents and their effects on device performance are not disclosed and taught.

Contents of the invention

The present invention aims to provide a series of metal complexes comprising the L _a ligand of formula 1 to solve at least part of the above problems. The application of these new compounds in electroluminescent devices can obtain very excellent device performance, such as the reduction of device voltage, the improvement of current efficiency, power efficiency and external quantum efficiency, which can comprehensively improve the performance of all aspects of the device, and finally obtained the The overall performance of the device has been greatly improved.

According to an embodiment of the present invention, a metal complex is disclosed, which includes a metal M, and a ligand L _a coordinated to the metal M, wherein L _a has a structure represented by formula 1:

In formula 1,

The metal M is selected from metals with a relative atomic mass greater than 40;

Each occurrence of ring Cy is identically or differently selected from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; and The ring Cy contains at least 3 carbon atoms;

Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

Each occurrence of X is identically or differently selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R's are present simultaneously, the two R's are identical or different;

Each occurrence of X ₁ -X ₈ is identically or differently selected from C, CR _x , CR _x1 or N; at least one of X ₁ -X ₄ is C and is connected to the ring Cy;

X ₁ , X ₂ , X ₃ or X ₄ are connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

At least one of X ₁ -X ₈ is selected from CR _x1 , and R _x1 has the structure shown in formula 2:

Among them, in formula 2,

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence;

Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof;

n is 0 or 1;

A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"';

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

R', R", R"', _Rx , _RA , _RB are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted having 1-20 carbons Atomic alkyl, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 3-20 Heterocyclic group of ring atoms, substituted or unsubstituted aralkyl group with 7-30 carbon atoms, substituted or unsubstituted alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aralkyl group with 6-30 carbon atoms aryloxy with 2-20 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted alkynyl with 2-20 carbon atoms, substituted or unsubstituted with 6-30 Aryl group with carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted heteroaryl group with 6-20 carbon atoms Arylsilyl groups with carbon atoms, substituted or unsubstituted alkylgermanyl groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups with Amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof with 0-20 carbon atoms;

"*" indicates the connection position of the formula 2;

Adjacent R', R _x can optionally be connected to form a ring;

Adjacent R", R"', _RA , _RB can optionally be connected to form a ring.

According to another embodiment of the present invention, an electroluminescence device is also disclosed, which includes: an anode, a cathode, and an organic layer arranged between the anode and the cathode, at least one of the organic layers includes the mentioned metal complexes.

According to another embodiment of the present invention, a compound combination is also disclosed, which includes the metal complexes described in the above embodiments.

The present invention discloses a series of metal complexes comprising L _a ligands with the structure of formula 1. These novel compounds can be used in electroluminescent devices to obtain very excellent device performance, such as reduction of device voltage, current efficiency, power efficiency and The improvement of external quantum efficiency can comprehensively improve the performance of all aspects of the device, and finally obtain a great improvement in the overall performance of the device.

Description of drawings

Figure 1 is a schematic diagram of an organic light-emitting device that may contain the metal complexes disclosed herein and compositions comprising the metal complexes.

2 is a schematic diagram of another organic light emitting device that may contain a metal complex disclosed herein and a composition comprising the metal complex.

Detailed ways

OLEDs can be fabricated on various substrates such as glass, plastic and metal. FIG. 1 schematically and non-limitatively shows an organic light emitting device 100 . The drawings are not necessarily drawn to scale, and some layer structures in the drawings can also be omitted as required. Device 100 may include substrate 101 , anode 110 , hole injection layer 120 , hole transport layer 130 , electron blocking layer 140 , light emitting layer 150 , hole blocking layer 160 , electron transport layer 170 , electron injection layer 180 and cathode 190 . Device 100 may be fabricated by sequentially depositing the described layers. The properties and functions of the various layers and exemplary materials are described in more detail in US Patent No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated herein by reference.

Each of these layers has more instances. For example, flexible and transparent substrate-anode combinations are disclosed in US Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with _F4 -TCNQ at a molar ratio of 50:1, as in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. published in. Examples of host materials are disclosed in US 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 US Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes comprising a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. Composite cathode. The principles and use of barrier layers are described in more detail in US Patent No. 6,097,147 and US Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

The layered structure described above is provided by way of non-limiting example. The functionality of OLEDs can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials can be used to achieve optimum performance. Any functional layer can consist of several sub-layers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

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

OLEDs also need encapsulation layers. Figure 2 schematically and non-limitatively shows an organic light-emitting device 200, which is different from Figure 1 in that an encapsulation layer 102 may 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 US Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

Devices fabricated in accordance with embodiments of the present invention may 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, head-up displays, fully or partially transparent displays, flexible displays, Smartphones, tablets, phablets, wearables, smart watches, laptops, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays and taillights.

The materials and structures described herein can also be used in other organic electronic devices listed above.

As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that a first layer is "in contact with" a 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 anode.

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.

A ligand may be referred to as "photosensitive" when it is believed to directly contribute to the photosensitive properties of the emissive material. A ligand may be referred to as "ancillary" when the ligand is not believed to contribute to the photosensitizing properties of the emissive material, but the ancillary ligand may alter the properties of the photosensitizing ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can be exceeded by retarding fluorescence beyond the 25% spin-statistical limit. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have an extremely small singlet-triplet gap for transitions between energy states. Thermal energy can activate the transition transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delay component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of backfilling singlet excited states may reach 75%. The total singlet fraction can be 100%, well over 25% of the spin statistics of the electrogenerated excitons.

Type E delayed fluorescence features can be seen in exciplex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires a light-emitting material to have a small singlet-triplet energy gap (ΔE _ST ). Organic metalloid-containing donor-acceptor luminescent materials may be able to achieve this. The emission from these materials is generally characterized as a donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO from the LUMO in these donor-acceptor type compounds generally results in a small ΔE _ST . These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (such as an amino group or a carbazole derivative) with an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

Definitions of Substituent Terms

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

Alkyl - as used herein, includes straight chain and branched chain 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, 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. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, alkyl groups may be optionally substituted.

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

Heteroalkyl - As used herein, a heteroalkyl comprises one or more carbons in the alkyl chain selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron A group of heteroatoms is substituted. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl Dimethylaminomethyl, Trimethylgermanylmethyl, Trimethylgermanylethyl, Trimethylgermanylisopropyl, Dimethylethylgermanylmethyl, Dimethylgermanylisopropyl Germanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, Trimethylsilylmethyl, Trimethylsilylethyl, Trimethylsilylisopropyl, Triisopropylsilylmethyl, Triisopropylsilylethyl. In addition, heteroalkyl groups can be optionally substituted.

Alkenyl - as used herein, encompasses straight chain, branched and cyclic alkenyl groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2 ,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methallyl, 1,1-dimethylallyl, 2-methallyl, 1-phenyl Allyl, 2-Phenylallyl, 3-Phenylallyl, 3,3-Diphenylallyl, 1,2-Dimethylallyl, 1-Phenyl-1-Butyl Alkenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraene group and norbornenyl group. Additionally, alkenyl groups may be optionally substituted.

Alkynyl - as used herein, straight chain alkynyl is encompassed. The alkynyl group may be an alkynyl group comprising 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups 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 are preferable. Additionally, alkynyl groups may be optionally substituted.

苝和薁，优选苯基，联苯，三联苯，三亚苯，芴和萘。非稠合芳基的例子包括苯基，联苯-2-基，联苯-3-基，联苯-4-基，对三联苯-4-基，对三联苯-3-基，对三联苯-2-基，间三联苯-4-基，间三联苯-3-基，间三联苯-2-基，邻甲苯基，间甲苯基，对甲苯基，对-(2-苯基丙基)苯基，4'-甲基联二苯基，4”-叔丁基-对三联苯-4-基，邻-枯基，间-枯基，对-枯基，2,3-二甲苯基，3,4-二甲苯基，2,5-二甲苯基，均三甲苯基和间四联苯基。另外，芳基可以任选被取代。Aryl or Aromatic - 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, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenylene, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene,

Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl Phenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropane Base) phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-di Tolyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadryl. In addition, the aryl group may be optionally substituted.

Heterocyclyl or Heterocycle - 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 nitrogen atoms, A group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxopentacyclyl, dioxanyl, aziridinyl, dihydro Pyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepanyl, azepanyl and tetra Hydrogen Thiolyl. In addition, heterocyclyl groups may be optionally substituted.

Heteroaryl - as used herein, non-fused and fused heteroaromatic groups which may contain from 1 to 5 heteroatoms, of which at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon Atoms, phosphorus atoms, germanium atoms, and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole , pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, Oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furopyridine, benzothienopyridine, thienodipyridine, benzene Selenenopyridine, selenobenzobipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1 , 2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogues. In addition, heteroaryl groups can be optionally substituted.

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

Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenoxy. In addition, aryloxy groups may be optionally substituted.

Aralkyl - As used herein, encompasses aryl substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group 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 Base, 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, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl , p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p- Cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2- Phenylisopropyl. In addition, aralkyl groups may be optionally substituted.

Alkylsilyl - as used herein encompasses alkyl substituted silyl groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropyl Silyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, methyldi-tert-butyl Silicon base. In addition, the alkylsilyl groups may be optionally substituted.

Arylsilyl - as used herein, encompasses at least one aryl substituted silyl 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, phenylbiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldiphenylsilyl, Methylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl Base tert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

Alkylgermanyl - As used herein, encompasses alkyl substituted germanyl. The alkylgermanyl group may be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl Dimethyl germanyl, methyl diisopropyl germanyl, dimethyl isopropyl germanyl, tri-tert-butyl germanyl, triisobutyl germanyl, dimethyl tert-butyl germanyl, methyl di-tert-butyl base germanium base. In addition, the alkylgermanyl groups may be optionally substituted.

Arylgermanyl - As used herein, at least one aryl or heteroaryl substituted germanyl is encompassed. The arylgermanyl group may be an arylgermanyl group having 6 to 30 carbon atoms, preferably an arylgermanyl group having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenylbiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldiphenylgermanyl, Methylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyl Base tert-butyl germanium base. In addition, the arylgermanyl groups may be optionally substituted.

The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or at least two C-H groups in the corresponding aromatic moiety are replaced by nitrogen atoms. For example, azatriphenylenes include 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 aza derivatives described above will readily occur to those of ordinary skill in the art, and all such analogs are intended to be included within the terms described herein.

In this disclosure, unless otherwise defined, when using any term in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aryl Alkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted Alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, means alkyl, cycloalkyl , heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, aryl Any one of germanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphinoyl can be selected from deuterium, halogen, unsubstituted with 1- Alkyl with 20 carbon atoms, unsubstituted cycloalkyl with 3-20 ring carbon atoms, unsubstituted heteroalkyl with 1-20 carbon atoms, unsubstituted heteroalkyl with 3-20 ring atoms Heterocyclyl, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted Substituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted 3-30 carbon atoms Atomic heteroaryl, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkyl having 3-20 carbon atoms Germanium group, unsubstituted arylgermanyl group with 6-20 carbon atoms, unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, Substituted by mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, it may be based on whether it is a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuranyl) or in terms of whether it is The whole molecule (such as benzene, naphthalene, dibenzofuran) to write its name. As used herein, these different ways of specifying substituents or linking moieties are considered equivalent.

In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution of other stable isotopes in compounds may be preferred due to their enhanced device efficiency and stability.

In the compounds referred to in this disclosure, multiple substitutions are meant to include double substitutions up to the maximum number of available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitutions (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent can exist in multiple available substitution positions on its linking structure , the substituents present at multiple available substitution positions may have the same structure or different structures.

In the compounds mentioned in this disclosure, adjacent substituents in the compound cannot be connected to form a ring unless expressly defined, eg, adjacent substituents can optionally be connected to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can be optionally connected to form a ring, including the case where adjacent substituents can be connected to form a ring, and the case 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 monocyclic or polycyclic (including spiro ring, bridged ring, condensed ring, etc.), and alicyclic, heteroalicyclic, aromatic or heterocyclic aromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, to carbon atoms bonded directly to each other, or to carbon atoms further away. base. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

The statement that adjacent substituents can optionally be 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:

The statement that adjacent substituents can optionally be 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 chemically bonded to each other to form a ring, as exemplified by the following formula:

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

In addition, the statement that adjacent substituents can be optionally joined to form a ring is also intended to be taken to mean that, in the case where one of two adjacent substituents represents hydrogen, the second substituent is bonded to a hydrogen atom bond close to the position, thus forming a loop. This is exemplified by:

According to an embodiment of the present invention, a metal complex is disclosed, which includes a metal M, and a ligand L _a coordinated to the metal M, wherein L _a has a structure represented by formula 1:

In formula 1,

The metal M is selected from metals with a relative atomic mass greater than 40;

Each occurrence of ring Cy is identically or differently selected from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; and The ring Cy contains at least 3 carbon atoms;

Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

Each occurrence of X is identically or differently selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R's are present simultaneously, the two R's are identical or different;

Each occurrence of X ₁ -X ₈ is identically or differently selected from C, CR _x , CR _x1 or N; at least one of X ₁ -X ₄ is C and is connected to the ring Cy;

X ₁ , X ₂ , X ₃ or X ₄ are connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

When X ₁ , X ₂ , X ₃ or X ₄ is connected to the metal M through a metal-carbon bond, X ₁ , X ₂ , X ₃ or X ₄ is selected from C;

At least one of X ₁ -X ₈ is selected from CR _x1 , and R _x1 has the structure shown in formula 2:

Among them, in formula 2,

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence;

Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof;

n is 0 or 1;

A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"';

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

R', R", R"', _Rx , _RA , _RB are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted having 1-20 carbons Atomic alkyl, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 3-20 Heterocyclic group of ring atoms, substituted or unsubstituted aralkyl group with 7-30 carbon atoms, substituted or unsubstituted alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aralkyl group with 6-30 carbon atoms aryloxy with 2-20 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted alkynyl with 2-20 carbon atoms, substituted or unsubstituted with 6-30 Aryl group with carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted heteroaryl group with 6-20 carbon atoms Arylsilyl groups with carbon atoms, substituted or unsubstituted alkylgermanyl groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups with Amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof with 0-20 carbon atoms;

"*" indicates the connection position of the formula 2;

Adjacent R', R _x can optionally be connected to form a ring;

Adjacent R", R"', _RA , _RB can optionally be connected to form a ring.

In this article, "R', R _x can be optionally connected to form a ring" is intended to represent adjacent substituent groups, for example, between two substituents R', between two substituents R _x , Between the substituents R' and _Rx , any one or more of these groups of substituents may be linked to form a ring. Obviously, none of these substituents may be connected to form a ring.

In this context, "R", R"', _RA , R _B can be optionally connected to form a ring", and it is intended to indicate that adjacent groups of substituents, for example, between two substituents R", two Between substituent R _A , between two substituents R _B , between substituent R _A and R", between substituent R _B and R", between substituent R _A and R"', substituent R Between _B and R"', between substituents R" and R"', any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring.

In this example, the L _a ligand having the structure of formula 1 is a bidentate ligand, ie L _a coordinates to the metal only through the virtual bond already shown in formula 1. In formula 1, there is no other mode or site of coordination with metal, for example, R _x1 does not coordinate with metal M.

Herein, "carbocycle" means that the ring atoms constituting the cyclic group contain only carbon atoms and do not contain heteroatoms. The cyclic group includes monocyclic rings and polycyclic rings (including spiro rings, bridged rings, condensed rings, etc.). "Carbocycle" includes saturated or unsaturated carbocycles, for example, alicyclic rings (eg, cycloalkyl, cycloalkenyl, cycloalkynyl, etc.) and aromatic rings are both carbocyclic rings.

Herein, "heterocyclic ring" means that the ring atoms constituting the cyclic group contain one or more heteroatoms, which can be selected from nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom , germanium atoms and boron atoms, etc. The cyclic group includes monocyclic rings and polycyclic rings (including spiro rings, bridged rings, condensed rings, etc.). "Heterocycle" includes saturated carbocycle or unsaturated carbocycle, for example, heteroalicyclic ring and heteroaromatic ring are both heterocyclic rings.

当n为1，且L选自单键时，即式2具有如下结构：

In this paper, when n is 0, it means that L does not exist in formula 2, that is, formula 2 has the following structure:

When n is 1, and L is selected from single bonds, that is, formula 2 has the following structure:

According to an embodiment of the present invention, wherein, each occurrence of ring Cy is identically or differently selected from any structure in the group consisting of:

in,

Each occurrence of R identically or differently represents single substitution, multiple substitution, or no substitution; when there are multiple Rs in any structure, the Rs are identical or different;

Each occurrence of R 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 having 3-20 ring carbons Atomic cycloalkyl, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted heterocyclyl with 7-30 Aralkyl of carbon atoms, substituted or unsubstituted alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted alkoxy of 2-20 Alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted aryl group having 3-30 carbon atoms Atomic heteroaryl, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted arylsilyl having 3-20 6-20 carbon atoms of alkylgermanium, substituted or unsubstituted arylgermanium of 6-20 carbon atoms, substituted or unsubstituted amino group of 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, Ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

Adjacent substituents R can optionally be connected to form a ring;

表示与X₁，X₂，X₃或X₄连接的位置。Among them, "#" indicates the position connected with metal M,

Indicates the position connected to X ₁ , X ₂ , X ₃ or X ₄ .

Herein, "adjacent substituents R can be optionally connected to form a ring" means that any one or more of the group formed between any two adjacent substituents R can be connected to form a ring. Obviously, none of these substituents may be connected to form a ring.

According to an embodiment of the present invention, wherein the metal complex has a general formula of M(L _a ) _m (L _b ) _n (L _c ) _q ;

Wherein, M is identically or differently selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each occurrence; preferably, M is identically or differently selected from Pt or Ir;

L _a , L _b and L _c are the first, second and third ligands coordinated with the metal M, respectively, and L _c and said L _a or L _b are the same or different; wherein, L _a , L _b and L _c can optionally be linked to form a multidentate ligand;

m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L _a The same or different; when n is 2, the two L _b are the same or different; when q is 2, the two L _c are the same or different;

Each occurrence of L _a is identically or differently selected from the group consisting of:

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when there are two R's at the same time, the two R's are the same or different;

Each occurrence of R, _Rx and _Rx1 identically or differently represents single substitution, multiple substitution or no substitution;

R _x1 has the structure shown in Formula 2:

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence;

Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof;

A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"';

n is 0 or 1;

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

"*" indicates the connection position of the formula 2;

Adjacent R', R _x can optionally be connected to form a ring;

Adjacent Rs can optionally be connected to form a ring;

Adjacent R", R"', _RA , R _B can optionally be connected to form a ring;

Each occurrence of L _b and L _c is identically or differently selected from any of the structures shown in the group consisting of:

in,

Each occurrence of X _b is identically or differently selected from the group consisting of: O, S, Se, NR _N1 , _CRC1 R _C2 ;

Each occurrence of R _a and R _b identically or differently represents single substitution, multiple substitution, or no substitution;

Adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 can optionally be connected to form a ring;

R', R", R"', R, R _x , R _A , R _B , R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are at each occurrence identically or differently selected from the group consisting of Groups: 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 having 1 -Heteroalkyl with 20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with Alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aryloxy group with 6-30 carbon atoms, substituted or unsubstituted alkenyl group with 2-20 carbon atoms, substituted or unsubstituted with Alkynyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted heteroaryl with 3 -Alkylsilyl with 20 carbon atoms, substituted or unsubstituted arylsilyl with 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl with 3-20 carbon atoms, substituted or unsubstituted Arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group , sulfinyl, sulfonyl, phosphino, and combinations thereof.

中相邻的取代基R_a，R_b能任选地连接形成环，当R_a任选地连接形成环时，

可以形成

的结构。Herein, "adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 can be optionally connected to form a ring" means that adjacent substituent groups, for example, two Between substituents R _a , between two substituents R _b , between substituents R _a and R _b , between substituents R _a and R c, between substituents R _b and _{R c ,} between substituents R Between _a and R _N1 , between substituent R _b and R _N1 , between substituent R _a and R _C1 , between substituent R _a and R _C2 , between substituent R _b and R _C1 , between substituent R Between _b and R _C2 , and between R _C1 and R _C2 , any one or more of these groups of substituents may be linked to form a ring. Obviously, none of these substituents may be connected to form a ring. For example,

Adjacent substituents R _a in and R _b can be optionally connected to form a ring, when R _a is optionally connected to form a ring,

can form

Structure.

According to an embodiment of the present invention, wherein the metal complex has a structure of Ir(L _a ) _m (L _b ) _3-m , and is represented by formula 3:

in,

m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, multiple L _a are the same or different;

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when there are two R's at the same time, the two R's are the same or different;

Each occurrence of Y ₁ -Y ₄ is identically or differently selected from CR or N;

Each occurrence of X ₃ -X ₈ is identically or differently selected from CR _x , CR _x1 or N;

At least one of X ₃ -X ₈ is selected from CR _x1 , and R _x1 has the structure shown in formula 2:

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence;

Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof;

A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"';

n is 0 or 1;

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

R', R", R"', R, _Rx , RA, _RB , _{R1 - R8} are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted Substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or Unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted Or unsubstituted aryloxy group with 6-30 carbon atoms, substituted or unsubstituted alkenyl group with 2-20 carbon atoms, substituted or unsubstituted alkynyl group with 2-20 carbon atoms, substituted or Unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or Unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3-20 carbon atoms, substituted or unsubstituted arylgermanium group having 6-20 carbon atoms substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and its combination;

Adjacent R ₁ -R ₈ can optionally be connected to form a ring;

Adjacent R', R _x can optionally be connected to form a ring;

Adjacent Rs can optionally be connected to form a ring;

Adjacent R", R"', _RA , _RB can optionally be connected to form a ring.

Herein, "adjacent R ₁ -R ₈ can optionally be connected to form a ring" is intended to mean any one or more of the group consisting of any two adjacent substituents in R ₁ -R ₈ Groups can be connected to form rings. Obviously, none of these substituents may be connected to form a ring.

According to an embodiment of the present invention, X ₁ -X ₈ are identically or differently selected from CR _x or CR _x1 at each occurrence.

According to an embodiment of the present invention, X ₁ -X ₈ are identically or differently selected from CR _x or CR _x1 each time they appear, and only one of X ₁ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₃ -X ₈ are identically or differently selected from CR _x or CR _x1 at each occurrence.

According to an embodiment of the present invention, X ₃ -X ₈ are identically or differently selected from CR _x or CR _x1 at each occurrence, and only one of X ₃ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, Y ₁ -Y ₄ are identically or differently selected from CR for each occurrence.

According to an embodiment of the present invention, at least one of X ₃ -X ₈ is N. For example, one of X ₃ -X ₈ is selected from N, or two of X ₃ -X ₈ are selected from N.

According to an embodiment of the present invention, at least one of X ₁ -X ₈ is N. For example, one of X ₁ -X ₈ is selected from N, or two of X ₁ -X ₈ are selected from N.

According to an embodiment of the present invention, at least one of Y ₁ -Y ₄ is N. For example, one of Y ₁ -Y ₄ is selected from N, or two of Y ₁ -Y ₄ are selected from N.

According to an embodiment of the present invention, wherein the metal complex has a structure of Ir(L _a ) _m (L _b ) _3-m , and is represented by formula 3A:

in,

m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, multiple L _a are the same or different;

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when there are two R's at the same time, the two R's are the same or different;

Each occurrence of R, _Rx and _Rx1 identically or differently represents single substitution, multiple substitution or no substitution;

R _x1 has the structure shown in formula 2:

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence;

Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof;

A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"';

n is 0 or 1;

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

R', R", R"', R, _Rx , RA, _RB , _{R1 - R8} are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted Substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or Unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted Or unsubstituted aryloxy group with 6-30 carbon atoms, substituted or unsubstituted alkenyl group with 2-20 carbon atoms, substituted or unsubstituted alkynyl group with 2-20 carbon atoms, substituted or Unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or Unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3-20 carbon atoms, substituted or unsubstituted arylgermanium group having 6-20 carbon atoms substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and its combination;

Adjacent R ₁ -R ₈ can optionally be connected to form a ring;

Adjacent R', R _x can optionally be connected to form a ring;

Adjacent Rs can optionally be connected to form a ring;

Adjacent R", R"', _RA , _RB can optionally be connected to form a ring.

According to an embodiment of the present invention, wherein, X is selected from O or S.

According to an embodiment of the present invention, wherein, X is selected from O.

According to an embodiment of the present invention, wherein A ₁ , A ₂ , B ₁ and B ₂ are selected from C identically or differently each time they appear.

According to an embodiment of the present invention, wherein, E is selected from N identically or differently at each occurrence.

According to an embodiment of the present invention, wherein each occurrence of R _x 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, A substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, a cyano group, and combinations thereof.

According to an embodiment of the present invention, wherein, each occurrence of R _x is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3-6 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-6 carbon atoms, a cyano group, and combinations thereof.

According to an embodiment of the present invention, wherein, each occurrence of R _x is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, normal Butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl , deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

According to an embodiment of the present invention, wherein, each occurrence of ring A and ring B is identically or differently selected from carbocycles having 5-12 ring atoms, heterocycles having 5-12 ring atoms, or a combination thereof .

According to an embodiment of the present invention, wherein, ring A and ring B are identically or differently selected from carbocycles having 5-6 ring atoms, heterocycles having 5-6 ring atoms, or combinations thereof .

According to an embodiment of the present invention, wherein, R _x1 has the structure represented by formula 4:

Each occurrence of A ₃ -A ₆ is identically or differently selected from CR _A or N;

Each occurrence of B ₃ -B ₆ is identically or differently selected from CR _B or N;

n is 0 or 1;

L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof;

Each occurrence of _RA , _RB and R" 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 heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted Substituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 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 Substituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, Substituted or unsubstituted aryl germanyl group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Adjacent R", R _A , R _B can optionally be connected to form a ring;

"*" indicates the connection position of the above formula 4.

当n为1，且L选自单键时，即式4具有如下结构：

In this embodiment, when n is 0, it means that L does not exist in formula 4, that is, formula 4 has the following structure:

When n is 1, and L is selected from single bonds, that is, formula 4 has the following structure:

According to an embodiment of the present invention, A ₃ -A ₆ are identically or differently selected from _CRA at each occurrence.

According to an embodiment of the present invention, wherein B ₃ -B ₆ are identically or differently selected from CR _B at each occurrence

According to an embodiment of the present invention, at least one of A ₃ -A ₆ is selected from N. For example, one of A ₃ -A ₆ is selected from N, or two of A ₃ -A ₆ are selected from N.

According to an embodiment of the present invention, at least one of B ₃ -B ₆ is selected from N. For example, one of B ₃ -B ₆ is selected from N, or two of B ₃ -B ₆ are selected from N.

According to an embodiment of the present invention, wherein each occurrence of R _A and R _B is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkane having 1-20 carbon atoms A substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted hetero group having 3-30 carbon atoms Aryl, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, cyano, and combinations thereof.

According to an embodiment of the present invention, wherein, at least one of _RA and _RB is selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups with 1-6 carbon atoms, substituted or unsubstituted Substituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or Unsubstituted alkylsilyl having 3-6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-6 carbon atoms, cyano, and combinations thereof.

According to an embodiment of the present invention, wherein each occurrence of R _A and R _B is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkane having 1-6 carbon atoms substituted or unsubstituted cycloalkyl with 3-6 ring carbon atoms, substituted or unsubstituted aryl with 6-12 carbon atoms, substituted or unsubstituted hetero with 3-12 carbon atoms Aryl, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-6 carbon atoms, cyano, and combinations thereof.

According to an embodiment of the present invention, wherein each occurrence of R _A and R _B is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl base, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated Isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

According to an embodiment of the present invention, wherein, L is selected from single bond, O, S, Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O) R", R"C=CR", heteroalkylene having 1-10 carbon atoms, cycloalkylene having 3-10 carbon atoms, heterocyclylene having 3-10 ring atoms, having Arylene groups having 6-10 carbon atoms, heteroarylene groups having 3-10 carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein, L is selected from single bond, O, S, NR", R"C=CR", and phenylene.

According to an embodiment of the present invention, wherein, L is selected from single bonds.

According to an embodiment of the present invention, wherein, each occurrence of R" is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3-6 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3-6 carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein, each occurrence of R" is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n Butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl , deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof.

According to an embodiment of the present invention, at least one of X ₃ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, at least one of X ₄ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₄ is selected from CR _x1 .

According to an embodiment of the present invention, at least one of X ₅ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₇ or X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, at least one of X ₁ -X ₈ is selected from CR _x , and said R _x is selected from cyano or fluorine, and at least one of X ₅ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, at least one of X ₃ -X ₈ is selected from CR _x , and said R _x is selected from cyano or fluorine, and at least one of X ₅ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, at least one of X ₅ -X ₈ is selected from CR _x , and said R _x is selected from cyano or fluorine, and at least one of X ₅ -X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₇ is selected from CR _x , said R _x is cyano or fluorine, and X ₈ is selected from CR _x1 .

According to an embodiment of the present invention, X ₈ is selected from CR _x , said R _x is cyano or fluorine, and X ₇ is selected from CR _x1 .

According to an embodiment of the present invention, wherein R _x1 is identically or differently selected from the group consisting of:

According to an embodiment of the present invention, the hydrogen in An ₁ to An ₁₁₈ can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, the hydrogen in An ₁ to An ₁₃₅ can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, wherein, each occurrence of R 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 aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted Or an unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms , substituted or unsubstituted amino groups having 6-20 carbon atoms and combinations thereof.

According to an embodiment of the present invention, wherein, each occurrence of R is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted Cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof .

According to an embodiment of the present invention, wherein at least one R is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3- Cycloalkyl with 20 ring carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted aryl with 3 -heteroaryl group with 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted Amino groups having 6-20 carbon atoms and combinations thereof.

According to an embodiment of the present invention, wherein 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 having 3-20 Cycloalkyl groups with ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein, at least one or at least two of R ₁ -R ₈ are selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, and substituted or unsubstituted ones have 3-20 A cycloalkyl group with ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all R ₁ -R ₄ and/or R ₅ -R ₈ is at least 4.

According to an embodiment of the present invention, wherein, at least one or at least two of R ₁ -R ₄ are selected from substituted or unsubstituted 1-20 carbon atom alkyl groups, and substituted or unsubstituted ones have 3-20 A cycloalkyl group with ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all R ₁ -R ₄ and/or R ₅ -R ₈ is at least 4.

According to an embodiment of the present invention, wherein, at least one or at least two of R ₅ -R ₈ are selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, and substituted or unsubstituted ones have 3-20 A cycloalkyl group with ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all R ₁ -R ₄ and/or R ₅ -R ₈ is at least 4.

According to an embodiment of the present invention, wherein, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are selected from the group consisting of: deuterium, substituted or unsubstituted with Alkyl group with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3-20 ring carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted cycloalkyl group with Heteroaryl groups of 3-30 carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are selected from the group consisting of: deuterium, substituted or unsubstituted with An alkyl group of 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are selected from the group consisting of: methyl, ethyl, propyl , isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, any of the aforementioned groups partially or fully deuterated, and deuterium.

According to an embodiment of the present invention, L _a is identically or differently selected from the group consisting of L _a1 to L _a1832 each time it appears, wherein the specific structure of L _a1 to L _a1832 is shown in claim 18 .

According to an embodiment of the present invention, the hydrogen atoms in L _a1 to L _a1832 can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, L _b is identically or differently selected from the group consisting of L _b1 to L _b334 at each occurrence, wherein the specific structures of L _b1 to L _b334 are shown in claim 19 .

According to an embodiment of the present invention, wherein, the hydrogen atoms in L _b1 to L _b334 can be partially or completely replaced by deuterium

According to an embodiment of the present invention, L _c is identically or differently selected from the group consisting of L _c1 to L _c360 each time it appears, wherein the specific structures of L _c1 to L _c360 are shown in claim 20 .

According to an embodiment of the present invention, wherein the metal complex has Ir(L _a ) ₃ or Ir(L _a ) ₂ L _b or IrL _a (L _b ) ₂ or Ir(L _a ) ₂ L _c or IrL _a ( The structure of L _c ) ₂ or Ir(L _a )(L _b )(L _c ), wherein L _a is identically or differently selected from the group consisting of L _a1 to L _a1832 at each occurrence, and L _b is the same at each occurrence Or differently selected from the group consisting of L _b1 to L _b334 , L _c is selected from the group consisting of L _c1 to L _c360 identically or differently each time it appears; wherein the specific structure of L _a1 to L _a1832 is shown in claim 18 , The specific structure of L _b1 to L _b334 is shown in claim 19, and the specific structure of L _c1 to L _c360 is shown in claim 20.

According to an embodiment of the present invention, the metal complex has a group consisting of metal complex 1 to metal complex 1576, wherein the specific structures of metal complex 1 to metal complex 1576 are shown in claim 21.

According to an embodiment of the present invention, wherein the metal complexes have metal complexes 1 to 1576 where hydrogen can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, L _a is identically or differently selected from the group consisting of L _a1 to L _a1891 each time it appears, wherein the specific structure of L _a1 to L _a1891 is shown in claim 18.

According to an embodiment of the present invention, the hydrogen atoms in L _a1 to L _a1891 can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, L _b is identically or differently selected from the group consisting of L _b1 to L _b341 at each occurrence, wherein the specific structures of L _b1 to L _b341 are shown in claim 19 .

According to an embodiment of the present invention, wherein, the hydrogen atoms in L _b1 to L _b341 can be partially or completely replaced by deuterium

According to an embodiment of the present invention, L _c is identically or differently selected from the group consisting of L _c1 to L _c360 each time it appears, wherein the specific structures of L _c1 to L _c360 are shown in claim 20 .

According to an embodiment of the present invention, wherein the metal complex has Ir(L _a ) ₃ or Ir(L _a ) ₂ L _b or IrL _a (L _b ) ₂ or Ir(L _a ) ₂ L _c or IrL _a ( The structure of L _c ) ₂ or Ir(L _a )(L _b )(L _c ), wherein each occurrence of L _a is identically or differently selected from the group consisting of L _a1 to L _a1891 , and each occurrence of L _b is the same or differently selected from the group consisting of L _b1 to L _b341 , L _c is identically or differently selected from the group consisting of L _c1 to L _c360 each time it appears; wherein the specific structure of L _a1 to L _a1891 is shown in claim 18 , The specific structure of L _b1 to L _b341 is shown in claim 19, and the specific structure of L _c1 to L _c360 is shown in claim 20.

According to an embodiment of the present invention, the metal complex has a group consisting of metal complex 1 to metal complex 1646 , wherein the specific structures of metal complex 1 to metal complex 1646 are shown in claim 21 .

According to an embodiment of the present invention, wherein the metal complexes have metal complexes 1 to 1646 where hydrogen can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, an electroluminescent device is also disclosed, which includes: an anode, a cathode, and an organic layer arranged between the anode and the cathode, at least one of the organic layers includes The metal complexes.

According to an embodiment of the present invention, wherein the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

According to an embodiment of the present invention, wherein the light emitting layer in the electroluminescent device emits green light.

According to an embodiment of the present invention, wherein, the light-emitting layer of the electroluminescent device includes a host compound, and the host compound includes one or more kinds; when the host compound is a combination of multiple compounds, it includes at least one an n-type host compound and at least one p-type host compound.

According to an embodiment of the present invention, wherein, the light-emitting layer of the electroluminescent device further includes a first host compound.

According to an embodiment of the present invention, wherein, the light-emitting layer of the electroluminescent device further includes a first host compound and a second host compound.

According to an embodiment of the present invention, wherein, at least one of the host 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 , silfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

According to an embodiment of the present invention, wherein, the first host compound has a structure represented by formula X:

in,

Each occurrence of L _x is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, A substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;

Each occurrence of V is identically or differently selected from C, CR _v or N, and at least one of V is C and is connected to L _x ;

Each occurrence of T is identically or differently selected from C, CR _t or N, and at least one of T is C and is connected to L _x ;

Each occurrence of R _v and R _t 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 having 3- Cycloalkyl with 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted with Aralkyl group with 7-30 carbon atoms, substituted or unsubstituted alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aryloxy group with 6-30 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 having Alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

_Each occurrence of Ar is identically or differently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

Adjacent substituents R _v and R _t can optionally be linked to form a ring.

In this embodiment, "adjacent substituents R _v and R _t can optionally be connected to form a ring" is intended to indicate that adjacent substituent groups, for example, between two substituents R _v , two substituents Between the substituents R _t and between 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 substituents may be connected to form a ring.

According to an embodiment of the present invention, wherein the first host compound has a structure represented by one of formula X-a to formula X-j:

in,

Each occurrence of L _x is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, A substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;

each occurrence of V is identically or differently selected from CR _v or N;

each occurrence of T is identically or differently selected from CR _t or N;

Each occurrence of R _v and R _t 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 having 3- Cycloalkyl with 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted with Aralkyl group with 7-30 carbon atoms, substituted or unsubstituted alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aryloxy group with 6-30 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 having Alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

_Each occurrence of Ar is identically or differently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

Adjacent substituents R _v and R _t can optionally be linked to form a ring.

According to an embodiment of the present invention, wherein the second host compound has a structure represented by formula 5:

in,

Each occurrence of E ₁ -E ₆ is identically or differently selected from C, CR _e or N, and at least two of E ₁ -E ₆ are N, at least one of E ₁ -E ₆ is C, and with Formula A is connected;

in,

Each occurrence of Q identical or different is selected from the group consisting of O, S, Se, N, NR _Q , CR _Q R _Q , SiR _Q R _Q , GeR _Q R _Q and R _Q C = CR _Q ; when present simultaneously When there are two R _Qs , the two R _Qs can be the same or different;

p is 0 or 1; r is 0 or 1;

When Q is selected from N, p is 0 and r is 1;

When Q is selected from the group consisting of O, S, Se, NR _Q , CR _Q R _Q , SiR _Q R _Q , GeR _Q R _Q and R _Q C=CR _Q , p is 1 and r is 0;

Each occurrence of L is identically or differently selected from single bond, substituted or unsubstituted alkylene group having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, substituted Or an unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;

Each occurrence of Q ₁ -Q ₈ is identically or differently selected from C, CR _q or N;

Each occurrence of R _e , R _Q and R _q 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 heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted Substituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or Unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted A heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or Unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino group having 0-20 carbon atoms, acyl , carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

"*" represents the connection position of formula A and formula 5;

Adjacent substituents R _e , R _Q , R _q can optionally be linked to form a ring.

In this article, "adjacent substituents R _e , R _Q , R _q can be optionally connected to form a ring" means that adjacent substituent groups, for example, between two substituents R _e , two Between two substituents R _Q , between two substituents R _q , between two substituents R _Q and R _q , any one or more of these groups of substituents may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring.

According to an embodiment of the present invention, wherein in the electroluminescence device, 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. %.

According to an embodiment of the present invention, wherein in the electroluminescence device, the metal complex is doped in 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. %.

According to an embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer, and the hole injection layer can be a single material functional layer, or a functional layer containing multiple materials, wherein the multiple The most commonly used material is that the hole transport material is doped with a certain proportion of p-type conductive dopant material. Common p-type dopant materials are:

According to another embodiment of the present invention, a composition is also disclosed, which includes a metal complex, and the specific structure of the metal complex is shown in any of the foregoing embodiments.

Combine with other materials

Materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in paragraphs 0132-0161 of US 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 one skilled in the art can readily consult the literature to identify other materials that can be used in combination.

Materials described herein as useful for particular layers in an organic light emitting device may 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 various hosts, transport layers, barrier layers, injection layers, electrodes, and other possible layers. Combinations of these materials are described in detail at paragraphs 0080-0101 of US 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 one skilled in the art can readily consult the literature to identify other materials that can be used in combination.

In the examples of material synthesis, all reactions were carried out under the protection of nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received 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 chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential The scanning calorimeter, the fluorescence spectrophotometer of Shanghai Prism Technology, the electrochemical workstation of Wuhan Kesite, the sublimation instrument of Anhui Beike, etc.) have carried out structure confirmation and characteristic testing by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also conventional equipment in the field (including but not limited to the vapor deposition machine produced by Angstrom Engineering, the optical test system and life test system produced by Suzhou Fushida, the ellipsometric test system produced by Beijing Liangtuo Instruments, etc.), tested by methods well known to those skilled in the art. Since those skilled in the art know the use of the above-mentioned equipment, test methods and other related content, and can obtain the inherent data of the sample with certainty and without being affected, the above-mentioned related content will not be repeated in this patent.

Example of material synthesis

Synthesis Example 1: Synthesis of Metal Complex 765

At room temperature, under the protection of nitrogen, Intermediate 1 (2.0g, 2.2mmol) and Intermediate 2 (1.2g, 2.7mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 765 (1.0 g, 0.9 mmol, 40%) as a yellow solid. The product was identified as the target product with a molecular weight of 1047.3.

Synthesis Example 2: Synthesis of Metal Complex 785

At room temperature, under nitrogen protection, Intermediate 1 (2.0g, 2.2mmol) and Intermediate 3 (1.3g, 2.7mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0ml) and DMF (20.0ml) in sequence , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 785 (1.0 g, 0.8 mmol, 36%) as a yellow solid. The product was identified as the target product with a molecular weight of 1159.5.

Synthesis Example 3: Synthesis of Metal Complex 773

At room temperature, under the protection of nitrogen, Intermediate 1 (2.1g, 2.5mmol) and Intermediate 4 (1.3g, 2.8mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) in sequence , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 773 (0.5 g, 0.5 mmol, 20%) as a yellow solid. The product was identified as the target product with a molecular weight of 1075.4.

Synthesis Example 4: Synthesis of Metal Complex 697

At room temperature, under the protection of nitrogen, intermediate 1 (2.5g, 3.0mmol) and intermediate 5 (1.6g, 4.0mmol) were successively added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 697 (1.0 g, 1.0 mmol, 33%) as a yellow solid. The product was identified as the target product with a molecular weight of 1022.3.

Synthesis Example 5: Synthesis of Metal Complex 778

At room temperature, under nitrogen protection, Intermediate 1 (3.0g, 3.7mmol) and Intermediate 6 (2.8g, 5.7mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 778 (1.5 g, 1.4 mmol, 38%) as a yellow solid. The product was identified as the target product with a molecular weight of 1103.4.

Synthesis Example 6: Synthesis of Metal Complex 782

At room temperature, under the protection of nitrogen, intermediate 1 (1.4g, 1.7mmol) and intermediate 7 (1.1g, 2.0mmol) were successively added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 782 (0.5 g, 0.4 mmol, 24%) as a yellow solid. The product was identified as the target product with a molecular weight of 1159.5.

Synthesis Example 7: Synthesis of Metal Complex 777

At room temperature, under the protection of nitrogen, intermediate 1 (1.0g, 1.2mmol) and intermediate 8 (0.7g, 1.5mmol) were successively added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 777 (0.3 g, 0.3 mmol, 25%) as a yellow solid. The product was identified as the target product with a molecular weight of 1103.4.

Synthesis Example 8: Synthesis of Metal Complex 867

At room temperature, under the protection of nitrogen, intermediate 1 (1.7g, 2.1mmol) and intermediate 9 (1.2g, 2.7mmol) were successively added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain a yellow solid 867 (1.0 g, 0.9 mmol, 43%). The product was identified as the target product with a molecular weight of 1049.4.

Synthesis Example 9: Synthesis of Metal Complex 799

At room temperature, under the protection of nitrogen, Intermediate 1 (1.9g, 2.3mmol) and Intermediate 10 (1.5g, 3.5mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 96 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 799 (1.55 g, 1.48 mmol, 64%) as a yellow solid. The product was identified as the target product with a molecular weight of 1047.3.

Synthesis Example 10: Synthesis of Metal Complex 839

At room temperature, under the protection of nitrogen, intermediate 1 (1.9g, 2.3mmol) and intermediate 11 (1.3g, 3.1mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 839 (1.3 g, 1.27 mmol, 55%) as a yellow solid. The product was identified as the target product with a molecular weight of 1040.3.

Synthesis Example 11: Synthesis of Metal Complex 1577

At room temperature, under the protection of nitrogen, intermediate 25 (3.7 g, 5.1 mmol) and intermediate 13 (2.0 g, 7.6 mmol) were sequentially added to 290 ml of ethanol, and the temperature was raised to 80° C. for 24 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain intermediate 14 (1.75 g, 2.3 mmol, 45%).

Under the protection of nitrogen at room temperature, Intermediate 14 (0.6g, 0.7mmol) and carbazole (0.33g, 2.0mmol) were sequentially added to 30ml of DMF solvent, and the temperature was raised to 100°C for 24h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1577 (0.45 g, 0.42 mmol, 60%). The product was identified as the target product with a molecular weight of 911.2.

Synthesis Example 12: Metal Complex 789

At room temperature, under nitrogen protection, Intermediate 1 (2.5g, 3.0mmol) and Intermediate 15 (1.6g, 3.6mmol) were added to a mixture of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) in sequence solvent, and heated to 100 ° C for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 789 (1.66 g, 1.6 mmol, 52%). The product was identified as the target product with a molecular weight of 1055.4.

Synthesis Example 13: Synthesis of Metal Complex 725

At room temperature, under the protection of nitrogen, Intermediate 1 (2.5g, 3.0mmol) and Intermediate 16 (1.7g, 4.1mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (50.0mL) and DMF (50.0mL) , and heated to 100 ° C for 72 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 725 (0.9 g, 0.88 mmol, 29%) as a yellow solid. The product was identified as the target product with a molecular weight of 1022.4.

Synthesis Example 14: Synthesis of Metal Complex 797

At room temperature, under the protection of nitrogen, intermediate 1 (0.88g, 1.1mmol) and intermediate 17 (0.6g, 1.2mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 797 (0.36 g, 0.32 mmol, 29%) as a yellow solid. The product was identified as the target product with a molecular weight of 1123.4.

Synthesis Example 15: Synthesis of Metal Complex 1584

At room temperature, under the protection of nitrogen, Intermediate 1 (2.1g, 2.5mmol) and Intermediate 18 (1.3g, 2.8mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1584 (0.54 g, 0.50 mmol, 20%) as a yellow solid. The product was identified as the target product with a molecular weight of 1083.3.

Synthesis Example 16: Synthesis of Metal Complex 1606

At room temperature, under the protection of nitrogen, Intermediate 1 (2.0g, 2.5mmol) and Intermediate 19 (1.8g, 3.3mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1606 (1.0 g, 0.85 mmol, 34%) as a yellow solid. The product was identified as the target product with a molecular weight of 1163.4.

Synthesis Example 17: Synthesis of Metal Complex 1598

At room temperature, under the protection of nitrogen, intermediate 1 (0.5g, 0.6mmol) and intermediate 20 (0.3g, 0.7mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1598 (0.3 g, 0.28 mmol, 47%) as a yellow solid. The product was identified as the target product with a molecular weight of 1065.3.

Synthesis Example 18: Synthesis of Metal Complex 959

At room temperature, under the protection of nitrogen, intermediate 21 (1.5g, 1.61mmol) and intermediate 22 (1.05g, 1.93mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0mL) and DMF (20.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 959 (0.61 g, 0.54 mmol, 33%) as a yellow solid. The product was identified as the target product with a molecular weight of 1271.6.

Synthesis Example 19: Synthesis of Metal Complex 1612

At room temperature, under the protection of nitrogen, intermediate 21 (2.0g, 2.2mmol) and intermediate 23 (1.3g, 2.8mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1612 (0.47 g, 0.45 mmol, 20%) as a yellow solid. The product was identified as the target product with a molecular weight of 1184.5.

Synthesis Example 20: Synthesis of Metal Complex 1643

At room temperature, under the protection of nitrogen, intermediate 24 (2.0g, 2.2mmol) and intermediate 26 (1.3g, 2.6mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1643 (0.75 g, 0.4 mmol, 28%) as a yellow solid. The product was identified as the target product with a molecular weight of 1216.6.

Synthesis Example 21: Synthesis of Metal Complex 1645

At room temperature, under the protection of nitrogen, intermediate 27 (2.0g, 2.5mmol) and intermediate 28 (1.6g, 3.6mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0mL) and DMF (30.0mL) , and heated to 100 ° C for 120 h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether=1/1) to obtain metal complex 1645 (0.75 g, 0.4 mmol, 28%) as a yellow solid. The product was identified as the target product with a molecular weight of 1013.3.

Device embodiment

Device Example 1

First, a glass substrate with an 80 nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After processing, the substrates were dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Å/sec under a vacuum of about 10 ^-8 Torr. Compound HI is used as a hole injection layer (HIL). The compound HT is used as a hole transport layer (HTL). Compound H1 was used as an electron blocking layer (EBL). Then the metal complex 697 of the present invention is used as a dopant, co-deposited with compound H1 and compound H2 for use as an emitting layer (EML). On the EML, the compound HB acts as a hole blocking layer (HBL). On the HBL, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1 nm as an electron injection layer, and aluminum was evaporated to a thickness of 120 nm as a cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

Device Comparative Example 1

Device Comparative Example 1 was implemented in the same manner as Device Example 1, except that compound GD1 was used instead of metal complex 697 of the present invention in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in the table below. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

Part of the device structure of table 1 embodiment 1 and comparative example 1

The material structure used in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 2.

The device data of table 2 embodiment 1 and comparative example 1

From the data of Example 1 in Table 2 and Comparative Example 1, it can be seen that the difference between the metal complex 697 of the present invention and the compound GD1 of the comparative example is that the carbazole substituent on the ligand L _a is replaced by a phenyl group, which is applied In the same organic electroluminescent device, the voltage decreased by 0.26V, the CE increased by 8.4%, the PE increased by 16.1%, and the EQE increased by 9.7%. This proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with a _Rx1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

Device Example 2

Device Example 2 is implemented in the same manner as Device Example 1, except that the metal complex 697 of the present invention is replaced by the metal complex 867 in the light-emitting layer (EML).

Device Comparative Example 2

Device Comparative Example 2 was implemented in the same manner as Device Example 1, except that compound GD2 was used instead of metal complex 697 of the present invention in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in Table 3. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

Part of the device structure of table 3 embodiment 2 and comparative example 2

The newly used material structure in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 4.

The device data of table 4 embodiment 2 and comparative example 2

From the data of Example 2 of Table 4 and Comparative Example 2, it can be seen that the difference between the metal complex 867 of the present invention and the compound GD2 of the comparative example is that the diphenylamino substituent on the ligand L _a is replaced by deuterium. When applied to the same organic electroluminescent device, the voltage is reduced by 0.2V, the CE is increased by 6.7%, the PE is increased by 10.7%, and the EQE is increased by 8.2%. This proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with a _Rx1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

Device Example 3

Device Example 3 is implemented in the same manner as Device Example 1, except that the metal complex 697 of the present invention is replaced by metal complex 765 in the light-emitting layer (EML).

Device Embodiment 4

Device Example 4 is implemented in the same manner as Device Example 1, except that metal complex 785 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Comparative Example 4

Device Comparative Example 4 was implemented in the same manner as Device Example 1, except that compound GD3 was used instead of metal complex 697 of the present invention in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in Table 5. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

The partial device structure of table 5 embodiment 3, embodiment 4 and comparative example 3

The material structure used in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 6.

The device data of table 6 embodiment 3, embodiment 4 and comparative example 3

From the data of Table 6 Example 3, Example 4 and Comparative Example 3, it can be seen that: on the basis that the L _a ligand has a cyano substituent, the metal complex 765 of the present invention, the metal complex 785 and the comparative example compound GD3 differs only in that the substituted or unsubstituted carbazole substituent on the ligand L _a is replaced by a phenyl group. When it is applied to the same organic electroluminescent device, the voltage decreases by 0.29V and 0.35V, respectively, and the CE increases by 5.3 %, 10.6%, PE increased by 10.4%, 22.1%, and EQE increased by 5.8%, 10.8%. At the same time, compared with Comparative Example 3, in Example 3 and Example 4, the half-peak widths were respectively narrowed by 1.4nm and 0.5nm without changing the maximum emission wavelength, indicating that more saturated green luminescence was obtained. The above proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with an R _x1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

In summary, the metal complexes provided by the present invention comprising L _a ligands with _Rx1 substituents can achieve devices with more excellent performance, such as the reduction of device voltage, the promotion of CE, PE and EQE, and can comprehensively Improve the performance of all aspects of the device, and finally obtain a great improvement in the overall performance of the device.

Device Embodiment 5

Device Example 5 is implemented in the same manner as Device Example 1, except that metal complex 725 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Comparative Example 4

Device Comparative Example 4 was implemented in the same manner as Device Example 1, except that compound GD4 was used instead of metal complex 697 of the present invention in the light-emitting layer (EML).

Device Embodiment 6

The embodiment of the device example 6 is the same as that of the device example 1, except that the metal complex 697 of the present invention is replaced by the metal complex 1577 in the light-emitting layer (EML), wherein compound H1:compound H2:metal complex 1577=56:38 :6.

Device Comparative Example 5

Device Comparative Example 5 was implemented in the same manner as Device Example 6, except that compound GD5 was used instead of metal complex 1577 of the present invention in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in Table 7. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

Part of the device structure of table 7 embodiment 5, embodiment 6 and comparative example 4, comparative example 5

The newly used material structure in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 8.

The device data of table 8 embodiment 5, embodiment 6 and comparative example 4, comparative example 5

As can be seen from the data in Table 8: compared with Example 5 and Comparative Example 4, the difference between the metal complex 725 of the present invention and the compound GD4 of the comparative example is only that the carbazole substituent on the ligand L _a is replaced by a biphenyl group, When it is applied to the same organic electroluminescent device, compared with Comparative Example 4, the voltage of Example 5 is reduced by 0.30V, CE is increased by 2.5%, PE is increased by 10.5%, and EQE is increased by 3.6%.

Compared with Example 6 and Comparative Example 5, the metal complex 1577 of the present invention and the comparative example compound GD5 differ only in that the carbazole substituent on the ligand L _a is replaced by a deuterated methyl group, which is applied to the same organic electrical In the luminescent device, compared with Comparative Example 5, the voltage of Example 6 is reduced by 0.10V, CE is increased by 13.0%, PE is increased by 17.5%, and EQE is increased by 11.8%.

This proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with a _Rx1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

Device Embodiment 7

Device Example 7 is implemented in the same manner as Device Example 1, except that metal complex 789 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Embodiment 8

Device Example 8 is implemented in the same manner as Device Example 1, except that metal complex 1584 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Embodiment 9

Device Example 9 is implemented in the same manner as Device Example 1, except that metal complex 797 of the present invention is used in place of metal complex 697 in the light-emitting layer (EML).

Device Example 10

Device Example 10 is implemented in the same manner as Device Example 1, except that metal complex 1606 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Example 11

Device Example 11 is implemented in the same manner as Device Example 1, except that metal complex 959 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Example 12

The embodiment of the device example 12 is the same as that of the device example 1, except that the metal complex 697 of the present invention is replaced by the metal complex 1643 in the light-emitting layer (EML), wherein compound H1:compound H2:metal complex 1643=71:23 :6.

The detailed device layer structure and thickness are shown in Table 9. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

Part of the device structure of Table 9 Embodiment 7 to Embodiment 12

The newly used material structure in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 10.

The device data of table 10 embodiment 7 to embodiment 12 and comparative example 3

As can be seen from the data in Table 10, compared with Comparative Example 3 in Example 7 to Example 10, on the basis that the L _a ligand has a cyano substituent, the metal complexes 789, 1584, 797, 1606 of the present invention and the pair The only difference in the proportional compound GD3 is that the differently substituted carbazolyl groups on the ligand L _a are replaced by phenyl groups. When it is applied to the same organic electroluminescent device, the half-peak widths are narrowed by 0.5nm, 2.1nm, and 1.0nm, respectively. , 2.3nm, voltage decreased by 0.40V, 0.46V, 0.26V, 0.29V, CE increased by 4.3%, 7.4%, 4.3%, 3.2%, PE increased by 15.6%, 22.1%, 11.7%, 11.7%, EQE Increased by 3.7%, 6.5%, 5.0%, 3.9%. This proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with a _Rx1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

From the data of Example 11 and Example 12, it can be seen that the metal complexes 959 and 1643 of the present invention have R _x1 substituents in the case of the L _a ligand, respectively, on the L _a ligand and the L _b ligand. different substituents. It can be seen from the device results that the EQE is above 25%, and the CE is about 100 cd/A, and the EQE of Example 11 even reaches 26.55%. At the same time, their PE and voltage are also at a relatively high level, showing high overall device performance.

The above all show that adopting the metal complexes provided by the present invention comprising L _a ligands with _Rx1 substituents can obtain devices with better performance, can comprehensively improve the performance of all aspects of the device, and finally obtain the best comprehensive performance of the device. Great improvement.

Device Example 13

Device Example 13 is implemented in the same manner as Device Example 1, except that metal complex 799 replaces metal complex 697 of the present invention in the light-emitting layer (EML).

Device Comparative Example 6

Device Comparative Example 6 was implemented in the same manner as Device Example 1, except that compound GD6 was used instead of metal complex 697 of the present invention in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in Table 11. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

The partial device structure of table 11 embodiment 13 and comparative example 6

The newly used material structure in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 12.

The device data of table 12 embodiment 7 to embodiment 14 and comparative example 3, comparative example 6

Example 13 Comparing Comparative Example 6, it can be seen that the difference between the metal complex 799 of the present invention and the compound GD6 of the comparative example is that the carbazole substituent on the ligand L _a is replaced by a phenyl group. In the luminescent device, the half peak width of Example 15 is narrowed by 2.0nm, the voltage is reduced by 0.11V, the CE is increased by 5.8%, the PE is increased by 9.5%, and the EQE is increased by 6.5%.

The above shows that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with a _Rx1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtains an extremely high comprehensive performance of the device. big boost.

Device Example 14

The embodiment of the device example 14 is the same as that of the device example 1, except that the metal complex 697 of the present invention is replaced by the metal complex 839 in the light-emitting layer (EML), wherein compound H1:compound H2:metal complex 839=71:23 :6.

Device Comparative Example 7

Device Comparative Example 7 was implemented in the same manner as Device Example 14, except that compound GD7 was used instead of metal complex 839 of the present invention in the light emitting layer (EML).

The detailed device layer structure and thickness are shown in Table 13. Layers in which more than one material is used are obtained by doping different compounds in their stated weight ratios.

Part of the device structure of table 13 embodiment 14 and comparative example 7

The newly used material structure in the device is as follows:

The IVL characteristics of the devices were measured. The CIE data of the device were measured at a current density of 15mA/cm ² , the maximum emission wavelength λ _max , the full width at half maximum (FWHM), the device voltage (V), the current efficiency (CE), the power efficiency (PE) and the external quantum Efficiency (EQE). These data were recorded and presented in Table 14.

The device data of table 14 embodiment 14 and comparative example 7

From the device data in Table 14, it can be seen that compared with Comparative Example 7 in Example 14, on the basis that the L _a ligand has a fluorine substituent, the difference between the metal complex 839 of the present invention and the comparative compound GD7 is only in the ligand L _a The carbazole substituent on the above was replaced by phenyl, and it was applied to the same organic electroluminescent device, the voltage was reduced by 0.66V, the CE was increased by 4.6%, the PE was increased by 23.3%, and the EQE was increased by 5.5%. The above proves that a device with better performance can be obtained by using the metal complex provided by the present invention containing the L _a ligand with an R _x1 substituent, which can comprehensively improve the performance of all aspects of the device, and finally obtain an extremely high comprehensive performance of the device. big boost.

In summary, the metal complexes provided by the present invention comprising L _a ligands with _Rx1 substituents can achieve devices with more excellent performance, such as the reduction of device voltage, the promotion of CE, PE and EQE, and can comprehensively Improve the performance of all aspects of the device, and finally obtain a great improvement in the overall performance of the device.

It should be understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. Therefore, the invention as claimed may include variations from the specific and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories as to why the invention works are not intended to be limiting.

Claims (26)

1. A metal complex comprising a metal M, and a ligand L _a coordinated with the metal M, wherein L _a has a structure represented by formula 1:

In formula 1, The metal M is selected from metals with a relative atomic mass greater than 40; Each occurrence of ring Cy is identically or differently selected from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; and The ring Cy contains at least 3 carbon atoms; Cy is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; Each occurrence of X is identically or differently selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R's are present simultaneously, the two R's are identical or different; Each occurrence of X ₁ -X ₈ is identically or differently selected from C, CR _x , CR _x1 or N; at least one of X ₁ -X ₄ is C and is connected to the ring Cy; X ₁ , X ₂ , X ₃ or X ₄ are connected to the metal M through a metal-carbon bond or a metal-nitrogen bond; At least one of X ₁ -X ₈ is selected from CR _x1 , and R _x1 has the structure shown in formula 2:

Among them, in formula 2, R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence; Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof; n is 0 or 1; A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"'; L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof; R', R", R"', _Rx , _RA , _RB are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted having 1-20 carbons Atomic alkyl, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 3-20 Heterocyclic group of ring atoms, substituted or unsubstituted aralkyl group with 7-30 carbon atoms, substituted or unsubstituted alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aralkyl group with 6-30 carbon atoms aryloxy with 2-20 carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted alkynyl with 2-20 carbon atoms, substituted or unsubstituted with 6-30 Aryl group with carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted heteroaryl group with 6-20 carbon atoms Arylsilyl groups with carbon atoms, substituted or unsubstituted alkylgermanyl groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups with Amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof with 0-20 carbon atoms; "*" indicates the connection position of the formula 2; Adjacent R', R _x can optionally be connected to form a ring; Adjacent R", R"', _RA , _RB can optionally be connected to form a ring. 2. The metal complex as claimed in claim 1, wherein each occurrence of ring Cy is identically or differently selected from any structure in the group consisting of:

in, Each occurrence of R identically or differently represents single substitution, multiple substitution, or no substitution; when there are multiple Rs in any structure, the Rs are identical or different; Each occurrence of R 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 having 3-20 ring carbons Atomic cycloalkyl, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted heterocyclyl with 7-30 Aralkyl of carbon atoms, substituted or unsubstituted alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted alkoxy of 2-20 Alkenyl group having 2-20 carbon atoms, substituted or unsubstituted alkynyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted aryl group having 3-30 carbon atoms Atomic heteroaryl, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted arylsilyl having 3-20 Alkyl germanyl with 6 carbon atoms, substituted or unsubstituted aryl germanyl with 6-20 carbon atoms, substituted or unsubstituted amino with 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, Ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; Adjacent substituents R can optionally be connected to form a ring; Among them, "#" indicates the position connected with metal M,

Indicates the position connected to X ₁ , X ₂ , X ₃ or X ₄ . 3. The metal complex of claim 1, wherein the metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q ; Wherein, M is identically or differently selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each occurrence; preferably, M is identically or differently selected from Pt or Ir; L _a , L _b and L _c are the first, second and third ligands coordinated with the metal M, respectively, and L _c and said L _a or L _b are the same or different; wherein, L _a , L _b and L _c can optionally be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L _a The same or different; when n is 2, the two L _b are the same or different; when q is 2, the two L _c are the same or different; Each occurrence of L _a is identically or differently selected from the group consisting of:

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when there are two R's at the same time, the two R's are the same or different; Each occurrence of R, _Rx and _Rx1 identically or differently represents single substitution, multiple substitution or no substitution; R _x1 has the structure shown in Formula 2:

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence; Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof; A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"'; n is 0 or 1; L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof; "*" indicates the connection position of the formula 2; Adjacent R', R _x can optionally be connected to form a ring; Adjacent Rs can optionally be connected to form a ring; Adjacent R", R"', _RA , R _B can optionally be connected to form a ring; Each occurrence of L _b and L _c is identically or differently selected from any of the structures shown in the group consisting of:

in, Each occurrence of X _b is identically or differently selected from the group consisting of: O, S, Se, NR _N1 , _CRC1 R _C2 ; Each occurrence of R _a and R _b identically or differently represents single substitution, multiple substitution, or no substitution; Adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 can optionally be connected to form a ring; R', R", R"', R, R _x , R _A , R _B , R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are at each occurrence identically or differently selected from the group consisting of Groups: 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 having 1 -Heteroalkyl with 20 carbon atoms, substituted or unsubstituted heterocyclyl with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with Alkoxy group with 1-20 carbon atoms, substituted or unsubstituted aryloxy group with 6-30 carbon atoms, substituted or unsubstituted alkenyl group with 2-20 carbon atoms, substituted or unsubstituted with Alkynyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted heteroaryl with 3 -Alkylsilyl with 20 carbon atoms, substituted or unsubstituted arylsilyl with 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl with 3-20 carbon atoms, substituted or unsubstituted Arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group , sulfinyl, sulfonyl, phosphino, and combinations thereof. 4. The metal complex according to claim 1, wherein the metal complex has a structure of Ir(L _a ) _m (L _b ) _3-m , and is represented by Formula 3:

in, m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, multiple L _a are the same or different; X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when there are two R's at the same time, the two R's are the same or different; Each occurrence of Y ₁ -Y ₄ is identically or differently selected from CR or N; Each occurrence of X ₃ -X ₈ is identically or differently selected from CR _x , CR _x1 or N; At least one of X ₃ -X ₈ is selected from CR _x1 , and R _x1 has the structure shown in formula 2:

R _A and R _B identically or differently represent single substitution, multiple substitution or no substitution at each occurrence; Ring A and ring B are identically or differently selected from carbocycles with 3-30 ring atoms, heterocycles with 3-30 ring atoms, or combinations thereof; A ₁ , A ₂ , B ₁ , B ₂ , E are identically or differently selected at each occurrence from C, N, B, P, CR"', SiR"' or GeR"'; n is 0 or 1; L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof; R', R", R"', R, _Rx , RA, _RB , _{R1 - R8} are identically or differently selected at each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted Substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or Unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted Or unsubstituted aryloxy group with 6-30 carbon atoms, substituted or unsubstituted alkenyl group with 2-20 carbon atoms, substituted or unsubstituted alkynyl group with 2-20 carbon atoms, substituted or Unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or Unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3-20 carbon atoms, substituted or unsubstituted arylgermanium group having 6-20 carbon atoms substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and its combination; Adjacent R ₁ -R ₈ can optionally be connected to form a ring; Adjacent R', R _x can optionally be connected to form a ring; Adjacent Rs can optionally be connected to form a ring; Adjacent R", R"', _RA , _RB can optionally be connected to form a ring. 5. The metal complex as claimed in claim 4, wherein X ₃ -X ₈ are selected from CR _x and CR _x1 identically or differently at each occurrence, and/or Y ₁ -Y ₄ are identical or different at each occurrence Variously selected from CR. 6. The metal complex according to claim 4, wherein at least one of X ₃ -X ₈ is N, and/or at least one of Y ₁ -Y ₄ is N. 7. The metal complex according to any one of claims 1-6, X is selected from O or S. 8. The metal complex as claimed in any one of claims 1-7, wherein R _x is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1 -20 carbon atom alkyl group, substituted or unsubstituted cycloalkyl group with 3-20 ring carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 -heteroaryl group with 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl group with 3-20 carbon atoms, cyano group, and combination; Preferably, each occurrence of R _x is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted having 3- Cycloalkyl with 6 ring carbon atoms, substituted or unsubstituted aryl with 6-12 carbon atoms, substituted or unsubstituted heteroaryl with 3-12 carbon atoms, substituted or unsubstituted heteroaryl with 3 -Alkylsilyl with 6 carbon atoms, substituted or unsubstituted alkylgermanyl with 3-6 carbon atoms, cyano, and combinations thereof; More preferably, each occurrence of R _x is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl , tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl , deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, and combinations thereof. 9. The metal complex as claimed in any one of claims 1-8, wherein _R has a structure represented by formula 4:

Each occurrence of A ₃ -A ₆ is identically or differently selected from CR _A or N; Each occurrence of B ₃ -B ₆ is identically or differently selected from CR _B or N; n is 0 or 1; L is selected from single bond, O, S, _SO2 , Se, NR", CR"R", SiR"R", GeR"R", BR", PR", P(O)R", R"C= CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, and a group having 6-30 carbon atoms Arylene, heteroarylene having 3-30 carbon atoms, and combinations thereof; Each occurrence of _RA , _RB and R" 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 heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted Substituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 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 Substituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, Substituted or unsubstituted aryl germanyl group with 6-20 carbon atoms, substituted or unsubstituted amino group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent R", R _A , R _B can optionally be connected to form a ring; "*" indicates the connection position of the above formula 4. 10. The metal complex as claimed in claim 9, wherein each occurrence of A ₃ -A ₆ is identically or differently selected from CR _A , and/or B ₃ -B ₆ is identically or differently selected from each occurrence From CR _B ; each occurrence of R _A and R _B 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 groups having 3-20 ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted Substituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, cyano groups, and combinations thereof; Preferably, each occurrence of R _A and R _B is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted Cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted Alkylsilyl groups having 3-6 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-6 carbon atoms, cyano groups, and combinations thereof; More preferably, at least one of R _A and R _B is selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted alkyl having 3-6 rings Cycloalkyl with carbon atoms, substituted or unsubstituted aryl with 6-12 carbon atoms, substituted or unsubstituted heteroaryl with 3-12 carbon atoms, substituted or unsubstituted with 3-6 Alkylsilyl with carbon atoms, substituted or unsubstituted alkylgermanyl with 3-6 carbon atoms, cyano, and combinations thereof. 11. The metal complex as claimed in claim 1 or 9, wherein L is selected from single bonds, O, S, Se, NR", CR "R", SiR "R", GeR "R", BR", PR", P(O)R", R"C=CR", heteroalkylene having 1-10 carbon atoms, cycloalkylene having 3-10 carbon atoms, having 3-10 ring atoms A heterocyclylene group, an arylene group having 6-10 carbon atoms, a heteroarylene group having 3-10 carbon atoms, and combinations thereof; Preferably, L is selected from single bond, O, S, NR", R"C=CR", phenylene; More preferably, L is selected from single bonds. 12. The metal complex as claimed in claim 1 or 4, wherein at least one of X ₅ -X ₈ is selected from CR _x1 ; Preferably, at least one of X ₇ or X ₈ is selected from CR _x1 ; More preferably, X ₈ is selected from CR _x1 . 13. The metal complex as claimed in claim 1 or 4, wherein at least one of X ₅ -X ₈ is selected from CR _x , and said R _x is selected from cyano or fluorine, and at least one of X ₅ -X ₈ And one more from CR _x1 ; Preferably, X ₇ is selected from CR _x , said R _x is cyano or fluorine, X ₈ is selected from CR _x1 ; and/or X ₈ is selected from CR _x , said R _x is cyano or fluorine, and X ₇ is selected from Since CR _x1 . 14. The metal complex as claimed in claim 1, wherein R _x1 is selected from the group consisting of An ₁ to An ₁₁₈ identically or differently at each occurrence:

Optionally, the hydrogen in An ₁ to An ₁₃₅ can be partially or completely replaced by deuterium. 15. The metal complex as claimed in any one of claims 1-14, wherein R is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1- Alkyl group with 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3-20 ring carbon atoms, substituted or unsubstituted aralkyl group with 7-30 carbon atoms, substituted or unsubstituted aralkyl group with 6 -30 carbon atom aryl, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl with 3-20 carbon atoms, substituted or unsubstituted heteroaryl with 6 -Arylsilyl groups with 20 carbon atoms, substituted or unsubstituted amino groups with 6-20 carbon atoms and combinations thereof; Preferably, 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 , a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, and combinations thereof. 16. The metal complex as claimed in claim 4, at least one or at least two of R ₁ -R ₈ are selected from substituted or unsubstituted 1-20 carbon atom alkyl groups, substituted or unsubstituted with 3 - a cycloalkyl group with 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all said R ₁ -R ₄ and/or R ₅ -R ₈ is at least 4; At least one or at least two of R ₁ -R ₄ are selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, or combination, and the sum of the carbon atoms of all R ₁ -R ₄ is at least 4; and/or at least one or at least two of R ₅ -R ₈ are selected from substituted or unsubstituted 1-20 carbon atoms An alkyl group, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, or a combination thereof, and the total number of carbon atoms of all R ₅ -R ₈ is at least 4. 17. The metal complex as claimed in claim 4, wherein, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are selected from the group consisting of: deuterium, substituted Or unsubstituted alkyl group with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3-20 ring carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted Or unsubstituted heteroaryl with 3-30 carbon atoms, and combinations thereof; Preferably, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are selected from the group consisting of deuterium, substituted or unsubstituted carbon atoms having 1-20 Alkyl, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, and combinations thereof; More preferably, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ are selected from the group consisting of: methyl, ethyl, propyl, isopropyl, n- Butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, any of the aforementioned groups partially or fully deuterated, and deuterium. 18. The metal complex as claimed in claim 1 or 14, wherein, L _a is selected from the group consisting of L _a1 to L _a1832 identically or differently each time it occurs, and the specific structures of L _a1 to L _a1832 are as follows: The following L _a1 to L _a1440 have the following structures:

Wherein X, Cy, R _X4 -R _X8 are selected from atoms or groups in the following table:

The following L _a1441 to L _a1514 have the following structures:

Wherein X, Cy, R _X4 -R _X8 are selected from atoms or groups in the following table:

The following L _a1515 to L _a1588 have the following structures:

Wherein X, Cy, R _X4 -R _X8 are selected from atoms or groups in the following table:

The following L _a1589 to L _a1662 have the following structures:

Wherein X, Cy, R _X4 -R _X8 are selected from atoms or groups in the following table:

The following L _a1663 to L _a1736 have the following structures:

Wherein X, Cy, R _X4 -R _X8 are selected from atoms or groups in the following table:

The following L _a1737 to L _a1760 have the following structures:

Wherein Cy, R _X4 -R _X7 are selected from atoms or groups in the following table:

The following L _a1761 to L _a1784 have the following structures:

Wherein X, Cy, R _X4 -R _X6 , R _X8 are selected from atoms or groups in the following table:

The following L _a1785 to L _a1808 have the following structures:

Wherein Cy, R _X4 -R _X5 , R _X7 - _{R X8} are selected from atoms or groups in the following table:

The following L _a1809 to L _a1832 have the following structures:

Wherein Cy, R _X4 , R _X6 -R _X8 are selected from atoms or groups in the following table:

In the above table, Cy1 to Cy9 have the following structures:

In Cy1 to Cy9, "#" indicates the position connected to the metal M,

Indicates the position connected to X ₁ , X ₂ , X ₃ or X ₄ ; In the above table, TMS means trimethylsilyl; TMG means trimethylgermanium;

Optionally, the hydrogen atoms in L _a1 to L _a1891 can be partially or completely replaced by deuterium. 19. The metal complex of claim 1 , 4 or 18, wherein each occurrence _{of L} is identically or differently selected from the group consisting of:

Optionally, the hydrogen atoms in L _b1 to L _b341 can be partially or completely replaced by deuterium. 20. The metal complex as claimed in claim 1 or 19, wherein each occurrence _{of L} is identically or differently selected from the group consisting of:

21. The metal complex of claim 20, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 1646; Wherein, metal complex 1 to metal complex 1364 have the structure of IrL _a (L _b ) ₂ , the two L _b are the same or different, and L _a and L _b respectively correspond to the structures shown in the following table:

Among them, metal complex 1365 to metal complex 1382 have the structure of Ir(L _a ) ₂ L _b , the two L _a are the same or different, and L _a and L _b respectively correspond to the structures shown in the following table:

Among them, metal complex 1383 to metal complex 1562 have the structure of Ir(L _a ) ₂ L _c , the two L _a are the same or different, and L _a and L _c respectively correspond to the structures shown in the following table:

Among them, the metal complexes 1563 to 1568 have the structure of Ir(L _a ) ₃ , the three L _a are the same or different, and the three L _a respectively correspond to the structures shown in the following table:

Among them, the metal complexes 1569 to 1576 have the structure of Ir(L _a )(L _b )(L _c ), and La _a , L _b and L _c respectively correspond to the structures shown in the following table:

Among them, metal complex 1577 to metal complex 1646 have the structure of IrL _a (L _b ) ₂ , the two L _b are the same, and La _and L _b respectively correspond to the structures shown in the following table:

Optionally, some or all of the hydrogen in the above-mentioned metal complexes 1 to 1646 can be replaced by deuterium. 22. An electroluminescent device comprising: anode, cathode, And an organic layer arranged between the anode and the cathode, at least one of the organic layers comprises the metal complex according to any one of claims 1-21. 23. The electroluminescent device according to claim 22, wherein said organic layer comprising said metal complex is a light emitting layer. 24. The electroluminescent device according to claim 23, wherein the light-emitting layer further comprises a first host compound; Preferably, the light-emitting layer further comprises a second host compound; 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, Isoquinone phenanthrene, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof. 25. The electroluminescent device according to claim 24, 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 1% of the total weight of the light-emitting layer. 30%; Preferably, the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer. 26. A composition comprising the metal complex of any one of claims 1-21.

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