A luminescent material with a polycyclic ligand

Abstract

A luminescent material with a polycyclic ligand is disclosed. The luminescent material is a novel metal complex with a polycyclic ligand and can be used as a luminescent material in an electroluminescent device. These novel metal complexes achieve red light emission and have a very narrow full width at half maximum, enabling high-saturation luminescence. In addition, when used as a luminescent material in an electroluminescent device, these novel metal complexes can achieve red light emission, have a very narrow full width at half maximum, enable high-saturation luminescence, can reduce or maintain a low voltage, and can also significantly improve the device efficiency and lifespan, providing better device performance. An electroluminescent device and a compound combination are also disclosed.

Description

Technical Field

[0001] 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 having a polycyclic ligand and an organic electroluminescent device and a compound combination comprising the metal complex. Background Art

[0002] Organic electronic devices include but are not limited to the following types: 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 electroluminescent devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). The 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 the anode. Since OLEDs are a self-emitting solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be classified into three different types according to their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlet and triplet states, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have 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 can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.

[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.

[0007] The emission color of OLEDs can be achieved through the structural design of the emitting materials. OLEDs can include one or more emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.

[0008] A phosphorescent emitting material is disclosed in CN110698518A, and its structural general formula is: Wherein X is N or P. Specific examples are: and It did not notice the huge impact brought by the further introduction of the fused ring structure.

[0009] For phosphorescent light-emitting materials, there have been reports in the prior art, but further in-depth research and development are still needed to meet the increasingly improved requirements of the industry for device performance, such as device emission color, emission saturation, voltage, device efficiency, device lifetime, etc. Summary of the Invention

[0010] The present invention aims to provide a series of metal complexes with polycyclic ligands to solve at least part of the above problems. The metal complexes can be used as light-emitting materials in organic electroluminescent devices. These novel metal complexes can achieve red light emission, have a very narrow full width at half maximum, and can achieve high-saturation light emission. In addition, when used as a light-emitting material in an electroluminescent device, these novel metal complexes can achieve red light emission, have a very narrow full width at half maximum, can achieve high-saturation light emission, can reduce or maintain a low voltage, and can also greatly improve the device efficiency and lifetime, and can provide better device performance.

[0011] According to an embodiment of the present invention, a metal complex is disclosed, which comprises a metal M and a ligand L coordinated with the metal M a , the metal is selected from metals with a relative atomic mass greater than 40, and the ligand L a has a structure represented by Formula 1:

[0012]

[0013] Wherein,

[0014] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0015] W is the same or different each time it appears and is selected from B, N or P;

[0016] Ring A, ring C and ring D are the same or different each time they appear and are selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 30 carbon atoms or a heteroaromatic ring having 3 - 30 carbon atoms;

[0017] Ring B is selected from a heterocyclic ring having 2 - 30 carbon atoms or a heteroaromatic ring having 2 - 30 carbon atoms;

[0018] R a , R b , R c and R d are the same or different each time they appear and represent mono-substitution, multi-substitution or no substitution;

[0019] R a , Rb , R c and R d Each occurrence is the same as or different from and is independently 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 heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted 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 heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0020] Adjacent substituents R a , R b , R c and R d can optionally be linked to form a ring.

[0021] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the metal complex shown in the above embodiment.

[0022] According to another embodiment of the present invention, a compound combination is also disclosed, which contains the metal complex shown in the above embodiment.

[0023] The novel metal complexes with polycyclic ligands disclosed in the present invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes can achieve red light emission, have a very narrow full width at half maximum, and can achieve highly saturated luminescence. In addition, when used as luminescent materials in electroluminescent devices, these novel metal complexes can achieve red light emission, have a very narrow full width at half maximum, can achieve highly saturated luminescence, can reduce or maintain a low voltage, and can also significantly improve the device efficiency and lifetime, and can provide better device performance. Description of the Drawings

[0024] Figure 1Schematic diagram of an organic light-emitting device that may contain a combination of the metal complexes and compounds disclosed herein.

[0025] Figure 2 Schematic diagram of another organic light-emitting device that may contain a combination of the metal complexes and compounds disclosed herein. Detailed Description

[0026] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 Schematically and non-limitingly shows an organic light-emitting device 100. The figures are not necessarily drawn to scale, and some layer structures in the figures may also be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of which is incorporated herein by reference.

[0027] There are more examples of each of these layers. For example, U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, which include a composite cathode having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer, are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties. The principles and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0028] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve the desired emission spectrum.

[0029] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0030] The OLED also requires a encapsulation layer, such as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which Figure 1 Differently, an encapsulation layer 102 can also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0031] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0032] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0033] As used herein, "top" means farthest from the substrate, and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" "on" the second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers can exist between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed" "on" the anode.

[0034] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0035] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be termed "photosensitive." When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be termed "auxiliary," but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0036] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistics limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0037] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay of the triplet state, the fraction of singlet excited state refilling can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.

[0038] The characteristics of E-type delayed fluorescence can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) with an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0039] Definition of substituent terms

[0040] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0041] Alkyl – As used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls 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. Additionally, the alkyl can be optionally substituted.

[0042] Cycloalkyl – As used herein, includes cyclic alkyls. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyls include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0043] Heteroalkyl – As used herein, heteroalkyl is formed by substituting one or more carbons in an alkyl chain with heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyls include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0044] Alkenyl - As used herein, it encompasses straight-chain, branched-chain, and cyclic olefin groups. The alkenyl can be an alkenyl group having 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0045] Alkynyl - As used herein, it encompasses straight-chain alkynyl groups. The alkynyl can be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0046] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can 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 include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyllyl, 3-p-terphenyllyl, 2-p-terphenyllyl, 4-m-terphenyllyl, 3-m-terphenyllyl, 2-m-terphenyllyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyllyl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl, and m-quaterphenyllyl. Additionally, the aryl can be optionally substituted.

[0047] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. 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, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrothienyl. Additionally, the heterocyclic group may be optionally substituted.

[0048] Heteroaryl - As used herein, may include non-fused and fused heteroaromatic groups having 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Heteroaryl also refers to heteroaromatic group. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborole, 1,3-azaborole, 1,4-azaborole, borazole, and their nitrogen analogs. Additionally, the heteroaryl may be optionally substituted.

[0049] Alkoxy - As used herein, it is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyl-oxy, ethoxyethyl-oxy, methoxymethyl-oxy and ethoxymethyl-oxy. Additionally, the alkoxy can be optionally substituted.

[0050] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0051] Aralkyl - As used herein, it encompasses alkyl substituted by aryl. The aralkyl can be an aralkyl having 7 to 30 carbon atoms, preferably an aralkyl having 7 to 20 carbon atoms, more preferably an aralkyl having 7 to 13 carbon atoms. Examples of aralkyl include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, 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 are preferred. Additionally, the aralkyl can be optionally substituted.

[0052] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0053] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0054] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.

[0055] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.

[0056] In terms such as azadibenzofuran and azadibenzothiophene, the term "aza" means that one or more C-H groups in the corresponding aromatic moiety are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and all such analogs are determined to be included within the terms described herein.

[0057] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following group is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl group, substituted ester group, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl group, ester group, sulfinyl, sulfonyl and phosphino can be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0058] It should be understood that when a molecular moiety is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a moiety (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or linking moiety are considered equivalent.

[0059] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Due to enhancing the efficiency and stability of the device, the replacement of other stable isotopes in the compounds may be preferred.

[0060] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist at multiple available substitution positions on its connecting structure, and the substituent existing at multiple available substitution positions can be of the same structure or different structures.

[0061] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be connected to form a ring, which includes both 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 optionally be connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0062] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0063]

[0064] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0065]

[0066] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0067]

[0068] In addition, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be construed as meaning that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following formula:

[0069]

[0070] According to one embodiment of the present invention, there is disclosed a metal complex comprising a metal M and a ligand L coordinated to the metal M a , wherein the metal is selected from metals having a relative atomic mass greater than 40, and the ligand L a has a structure represented by Formula 1:

[0071]

[0072] wherein,

[0073] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0074] W is the same or different each time it appears and is selected from B, N or P;

[0075] Ring A, Ring C and Ring D are the same or different each time they appear and are selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 - 30 carbon atoms or a heteroaromatic ring having 3 - 30 carbon atoms;

[0076] Ring B is selected from a heterocyclic ring having 2 - 30 carbon atoms or a heteroaromatic ring having 2 - 30 carbon atoms;

[0077] R a , R b , R c and R d are the same or different each time they appear and represent mono-substitution, multi-substitution or no substitution;

[0078] R a , R b , R c and R dEach occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0079] Adjacent substituents R a 、R b 、R c and R d can optionally be linked to form a ring.

[0080] As used herein, adjacent substituents R a 、R b 、R c and R d can optionally be linked to form a ring, which is intended to represent adjacent substituent groups therein. For example, between adjacent substituents R a , between adjacent substituents R b , between adjacent substituents R c , between adjacent substituents R d , between adjacent substituents R a and R b , between adjacent substituents R a and R d , and between adjacent substituents R b and R c , any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring.

[0081] According to one embodiment of the present invention, wherein the L aIn this case, ring A, ring C and ring D are each independently the same or different and are selected from aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 3-18 carbon atoms each time they appear; ring B is selected from heteroaromatic rings having 2-18 carbon atoms.

[0082] According to one embodiment of the present invention, wherein the L a In this case, ring A, ring C and ring D are each independently the same or different and are selected from aromatic rings having 6-10 carbon atoms or heteroaromatic rings having 5-10 ring atoms each time they appear; ring B is selected from heteroaromatic rings having 5-10 ring atoms.

[0083] According to one embodiment of the present invention, wherein the L a In this case, ring A, ring C and ring D are each independently the same or different and are selected from benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, furan ring, thiophene ring, isoxazole ring, isothiazole ring, pyrrole ring, pyrazole ring, benzofuran ring, benzothiophene ring, azabenzofuran ring, or azabenzothiophene ring; ring B is selected from pyrrole ring, indole ring, imidazole ring, pyrazole ring, triazole ring, azaindole ring.

[0084] According to one embodiment of the present invention, wherein the L a In this case, ring A, ring C and ring D are each independently the same or different and are selected from benzene ring, naphthalene ring, pyridine ring, pyrimidine ring; ring B is selected from pyrrole ring, indole ring, azaindole ring.

[0085] According to one embodiment of the present invention, wherein the L a is selected from the structures represented by any one of Formula 2 to Formula 19:

[0086]

[0087] Wherein,

[0088] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0089] W is the same or different each time it appears and is selected from B, N or P;

[0090] A1-A5 are the same or different each time they appear and are selected from N or CR a ;

[0091] B1-B4 are the same or different each time they appear and are selected from N or CR b ;

[0092] C1-C4 are the same or different each time they appear and are selected from N or CR c ;

[0093] D1-D4 are the same or different each time they appear and are selected from N or CR d ;

[0094] X1 is the same as or different from each other each time it appears and is selected from O, S, Se, NR c , CR c R c , SiR c R c or PR c ;

[0095] X2 is the same as or different from each other each time it appears and is selected from O, S, Se, NR d , CR d R d , SiR d R d or PR d ;

[0096] Z3 is the same as or different from each other each time it appears and is selected from O, S, Se, NR z , CR z R z , SiR z R z or PR z ;

[0097] R a 、R b 、R c 、R d and R z is the same as or different from each other each time it appears and is 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 heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted 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 heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0098] Adjacent substituents R a 、R b 、Rc , R d and R z can optionally be linked to form a ring.

[0099] In this embodiment, adjacent substituents R a , R b , R c , R d and R z can optionally be linked to form a ring, which is intended to represent adjacent substituent groups among them. For example, between adjacent substituents R a , between adjacent substituents R b , between adjacent substituents R c , between adjacent substituents R d , between adjacent substituents R a and R b , between adjacent substituents R a and R d , between adjacent substituents R b and R c , between adjacent substituents R a and R z , between adjacent substituents R d and R z , and between adjacent substituents R z . Any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring.

[0100] According to one embodiment of the present invention, wherein L a is selected from the structures represented by Formula 2, Formula 3, Formula 7, Formula 8, Formula 9 or Formula 12.

[0101] According to one embodiment of the present invention, wherein L a is selected from the structures represented by Formula 2, Formula 3, Formula 9 or Formula 12.

[0102] According to one embodiment of the present invention, wherein L a is selected from the structures represented by Formula 2, Formula 3 or Formula 12.

[0103] According to one embodiment of the present invention, wherein in Formulas 1 to 19, Z1 is N and Z2 is C.

[0104] According to one embodiment of the present invention, wherein in Formulas 1 to 19, Z1 is C and Z2 is N.

[0105] According to one embodiment of the present invention, wherein in Formulas 1 to 19, W is N.

[0106] According to one embodiment of the present invention, in Formulas 2 to 18, Z1 is N, and at least one of D1 and D2 is N; or, in Formulas 2 to 17 and 19, Z2 is N, and at least one of C1 and C2 is N.

[0107] According to one embodiment of the present invention, in Formulas 2 to 18, Z1 is N, and one of D1 and D2 is N; or, in Formulas 2 to 17 and 19, Z2 is N, and one of C1 and C2 is N.

[0108] According to one embodiment of the present invention, in Formulas 2 to 18, Z1 is N, and D2 is N; or, in Formulas 2 to 17 and 19, Z2 is N, and C1 is N.

[0109] According to one embodiment of the present invention, in Formulas 2 to 19, A1 - A5 are each independently selected from CR a , B1 - B4 are each independently selected from CR b ; in Formulas 2 to 17 and 19, C1 - C4 are each independently selected from CR c ; in Formulas 2 to 18, D1 - D4 are each independently selected from CR d ; the R a , R b , R c and R d are the same or different each time they appear and are 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 heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted 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 heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0110] Adjacent substituents R a , Rb , R c and R d may optionally be joined to form a ring.

[0111] According to one embodiment of the present invention, in Formulae 2 to 19, A1 - A5 are each independently selected from CR a , B1 - B4 are each independently selected from CR b ; in Formulae 2 to 17 and 19, C1 - C4 are each independently selected from CR c ; in Formulae 2 to 18, D1 - D4 are each independently selected from CR d ; the R a , R b , R c and R d are the same or different each time they appear and are 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 alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, cyano, and combinations thereof;

[0112] Adjacent substituents R a , R b , R c and R d may optionally be joined to form a ring.

[0113] According to one embodiment of the present invention, in Formulae 2 to 19, A1 - A5 are each independently selected from CR a , B1 - B4 are each independently selected from CR b ; in Formulae 2 to 17 and 19, C1 - C4 are each independently selected from CR c ; in Formulae 2 to 18, D1 - D4 are each independently selected from CR d ; the R a , R b , R c and R dEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof;

[0114] Adjacent substituents R a 、R b 、R c and R d can optionally be linked to form a ring.

[0115] According to one embodiment of the present invention, in the formulas 2 to 19, at least one of A1 - A n is the same as or different from and is selected from CR a , where the A n corresponds to the largest serial number among those where A1 - A5 exist in any one of the formulas 2 - 19; the R a each occurrence is the same as or different from and is selected from the group consisting of: deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, and combinations thereof;

[0116] Adjacent substituents R a can optionally be linked to form a ring.

[0117] In this context, adjacent substituents R a can optionally be linked to form a ring, which is intended to mean that any adjacent substituents R a can be linked to form a ring. Obviously, any adjacent substituents Ra They may also not be connected to form a ring.

[0118] In this embodiment, in the formulas 2 to 19, A1 - A n At least one of them, each time it appears, is the same or different and is selected from CR a The A n Corresponds to the largest serial number among the serial numbers where A1 - A5 exist in any one of the formulas 2 - 19. For example, for formula 2, the A n Corresponds to the largest serial number A3 among the serial numbers where A1 - A5 exist in formula 2. That is, in formula 2, at least one of A1 - A3, each time it appears, is the same or different and is selected from CR a ; Another example, for formula 4, the A n Corresponds to the largest serial number A5 among the serial numbers where A1 - A5 exist in formula 4. That is, in formula 4, at least one of A1 - A5, each time it appears, is the same or different and is selected from CR a ; Another example, for formula 15, the A n Corresponds to the largest serial number A1 among the serial numbers where A1 - A5 exist in formula 15. That is, in formula 15, A1, each time it appears, is the same or different and is selected from CR a .

[0119] According to an embodiment of the present invention, wherein, in the formulas 2 to 14, formula 18, and formula 19, at least one of A1 - A3, each time it appears, is the same or different and is selected from CR a ; In the formulas 15 to 17, A1 is selected from CR a .

[0120] According to an embodiment of the present invention, wherein, in the formulas 2 to 14, formula 18, and formula 19, at least one of A1 - A3, each time it appears, is the same or different and is selected from CR a ; In the formulas 15 to 17, A1 is selected from CR a ; The R a , each time it appears, is the same or different and is selected from the group consisting of: deuterium, fluorine, cyano, hydroxyl, mercapto, amino, methoxy, phenoxy, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidinyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, tert - butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, and combinations thereof.

[0121] According to an embodiment of the present invention, wherein, in the formulas 2 to 17 and formula 19, C2, each time it appears, is the same or different and is selected from CRc , where each occurrence of R c is the same as or different from each other and is selected from the group consisting of deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, and combinations thereof.

[0122] According to one embodiment of the present invention, in Formulas 2 to 17 and 19, C2 is the same as or different from each other and is selected from CR c , where each occurrence of R c is the same as or different from each other and is selected from the group consisting of deuterium, a cyano group, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.

[0123] According to one embodiment of the present invention, in Formulas 2 to 19, at least one of B1 - B n is selected from CR b ; B n corresponds to the largest serial number among those where B1 - B4 exist in any one of Formulas 2 - 19; and / or, in Formulas 2 to 18, at least one of D1 - D n is selected from CR d ; D n corresponds to the largest serial number among those where D1 - D4 exist in any one of Formulas 2 - 18; the R b , R dEach occurrence is the same as or different from and is 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 heterocyclic group having 3-20 ring atoms, substituted or unsubstituted 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 alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof.

[0124] In this embodiment, in the formulas 2 to 19, at least one of B1 - B n is the same as or different from and is selected from CR b each occurrence, and the B n corresponds to the largest serial number among those where B1 - B4 exist in any one of the formulas 2 - 19. For example, for formula 2, the B n corresponds to the largest serial number B4 among those where B1 - B4 exist in formula 2. That is, in formula 2, at least one of B1 - B4 is the same as or different from and is selected from CR b each occurrence; and for another example, for formula 13, the B n corresponds to the largest serial number B2 among those where B1 - B4 exist in formula 13. That is, in formula 13, at least one of B1 - B2 is the same as or different from and is selected from CR b each occurrence.

[0125] In this embodiment, in the formulas 2 to 18, at least one of D1 - D n is the same as or different from and is selected from CR d each occurrence, and the D n corresponds to the largest serial number among those where D1 - D4 exist in any one of the formulas 2 - 18. For example, for formula 2, the D n corresponds to the largest serial number D2 among those where D1 - D4 exist in formula 2. That is, in formula 2, at least one of D1 - D2 is the same as or different from and is selected from CR d each occurrence; and for another example, for formula 12, the D nCorresponding to the largest serial number D4 among D1-D4 present in Formula 12, that is, in Formula 12, at least one of D1-D4 is the same or different and is selected from CR each time it appears d 。

[0126] According to an embodiment of the present invention, wherein in the said Formula 2 to Formula 12, Formula 16, Formula 18 and Formula 19, B2 and / or B3 are selected from CR b ; in Formula 13 to Formula 15 and Formula 17, B1 and / or B2 are selected from CR b ; in the said Formula 2 to Formula 18, D1 and / or D2 are selected from CR d 。

[0127] According to an embodiment of the present invention, wherein in the said Formula 2 to Formula 12, Formula 16, Formula 18 and Formula 19, B2 and / or B3 are selected from CR b ; in Formula 13 to Formula 15 and Formula 17, B1 and / or B2 are selected from CR b ; in Formula 2 to Formula 18, D1 and / or D2 are selected from CR d ; the said R b 、R d are the same or different and are each time selected from the group consisting of: hydrogen, deuterium, fluorine, cyano group, hydroxyl group, mercapto group, amino group, methoxy group, phenoxy group, methylthio group, phenylthio group, dimethylamino group, diphenylamino group, phenylmethylamino group, vinyl group, tetrahydrofuranyl group, tetrahydropyranyl group, tetrahydrothienyl group, piperidinyl group, morpholinyl group, benzyl group, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, trimethylsilyl group, triethylsilyl group, trimethylgermyl group, triethylgermyl group, phenyl group, pyridyl group, triazinyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group, deuterated cyclopentylmethyl group, deuterated cyclohexyl group, deuterated neopentyl group, and combinations thereof.

[0128] According to an embodiment of the present invention, wherein in the said Formula 5 to Formula 8, Formula 10, Formula 11, Formula 15 to Formula 17, Z3 is the same or different and is each time selected from O, S or Se; in Formula 18, X1 is the same or different and is each time selected from O, S or Se; in Formula 19, X2 is the same or different and is each time selected from O, S or Se.

[0129] According to an embodiment of the present invention, wherein in the said Formula 5 to Formula 8, Formula 10, Formula 11, Formula 15 to Formula 17, Z3 is the same or different and is each time selected from O or S; in Formula 18, X1 is the same or different and is each time selected from O or S; in Formula 19, X2 is the same or different and is each time selected from O or S.

[0130] According to an embodiment of the present invention, wherein the said L aSame or different each time, selected from the group consisting of L a1 to L a1297 constitute the group.

[0131] According to an embodiment of the present invention, wherein the L a Same or different each time, selected from the group consisting of L a1 to L a1342 constitute the group:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] Among them, TMS represents trimethylsilyl, and Ph represents phenyl.

[0179] According to an embodiment of the present invention, wherein, said L a1 to L a1297 in the structure, the hydrogen part can be partially or completely replaced by deuterium.

[0180] According to an embodiment of the present invention, wherein, said L a1 to L a1342 in the structure, the hydrogen part can be partially or completely replaced by deuterium.

[0181] According to an embodiment of the present invention, wherein, the metal complex has the general formula M(L a ) m (L b ) n (L c ) q ;

[0182] Wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the metal M respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m + n + q is equal to the oxidation state of the metal M; when m is equal to 2 or 3, multiple L a can be the same or different; when n is equal to 2, 2 L b can be the same or different; when q is equal to 2, 2 L c can be the same or different;

[0183] L a , L b and L c can optionally be connected to form a polydentate ligand;

[0184] L b and L c are each independently selected from the group consisting of the following structures:

[0185]

[0186] Wherein,

[0187] R i , R ii and R iii each independently represent mono-substitution, multi-substitution or no substitution;

[0188] X a is each independently selected from the group consisting of: O, S, Se, NR N1 and CRC1 R C2 ;

[0189] X b and X c is the same as or different from each occurrence and is selected from the group consisting of O, S, Se, and NR N2 ;

[0190] R i 、R ii 、R iii 、R N1 、R N2 、R C1 and R C2 is the same as or different from each occurrence and is 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 heterocyclic group having 3-20 ring atoms, substituted or unsubstituted 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 heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0191] Adjacent substituents R i 、R ii 、R iii 、R N1 、R N2 、R C1 and R C2 can optionally be linked to form a ring.

[0192] In this example, adjacent substituents R i 、R ii 、R iii 、R N1 、R N2 、R C1 and R C2 can optionally be linked to form a ring, which is intended to indicate that in the L b 、Lc Adjacent substituent groups in the structure, for example, adjacent substituents R i Between, adjacent substituents R ii Between, adjacent substituents R iii Between, adjacent substituents R i And R ii Between, adjacent substituents R ii And R iii Between, adjacent substituents R i And R iii Between, adjacent substituents R i And R N1 Between, adjacent substituents R i And R C1 Between, adjacent substituents R i And R C2 Between, adjacent substituents R ii And R N1 Between, adjacent substituents R iii And R N1 Between, adjacent substituents R ii And R C1 Between, adjacent substituents R ii And R C2 Between, adjacent substituents R iii And R C1 Between, adjacent substituents R iii And R C2 Between, adjacent substituents R i And R N2 Between, adjacent substituents R ii And R N2 Between, and adjacent substituents R C1 And R C2 Between, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring at all.

[0193] In this embodiment, L a , L b And L c Can optionally be connected to form a polydentate ligand. For example, any two or three of L a , L b And L c Can be connected to form a tetradentate ligand or a hexadentate ligand. Obviously, L a , L b And L c Can also not be connected so as not to form a polydentate ligand.

[0194] According to an embodiment of the present invention, wherein the metal M is selected from Ir, Pt or Os.

[0195] According to one embodiment of the present invention, wherein the metal M is Ir.

[0196] According to one embodiment of the present invention, wherein L b is the same or different each time it appears and is selected from the following structures:

[0197]

[0198] wherein R1–R7 are the same or different each time they appear and are 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 heterocyclic group having 3-20 ring atoms, substituted or unsubstituted 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 heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0199] According to one embodiment of the present invention, wherein L b is the same or different each time it appears and is selected from the following structures:

[0200]

[0201] wherein at least one or two of R1-R3 are selected from 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, or combinations thereof; and / or at least one or two of R4-R6 are selected from 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, or combinations thereof.

[0202] According to one embodiment of the present invention, wherein L bThe same or different each time it appears and is selected from the following structures:

[0203]

[0204] Wherein at least two of R1 - R3 are selected from substituted or unsubstituted alkyl groups having 2 - 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 - 20 carbon atoms, or combinations thereof; and / or at least two of R4 - R6 are selected from substituted or unsubstituted alkyl groups having 2 - 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 - 20 carbon atoms, or combinations thereof.

[0205] According to one embodiment of the present invention, wherein said L b The same or different each time it appears and is selected from the group consisting of L b1 to L b322 :

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] According to one embodiment of the present invention, wherein said L c The same or different each time it appears and is selected from the group consisting of L c1 to L c231 :

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] According to one embodiment of the present invention, wherein the metal complex is an Ir complex and has a structure shown by any one of Ir(L a )(L b )(L c ), Ir(L a )2(L b ), Ir(L a )2(L c ), and Ir(L a )(L c )2; when the metal complex has the structure of Ir(L a )(L b )(L c ), the L a is optionally selected from any one of the group consisting of L a1 to L a1297 , the L b is optionally selected from any one of the group consisting of L b1 to L b322 , and the L c is optionally selected from any one of the group consisting of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )2(L b ), the L a is the same or different each time it appears and is optionally selected from any one or any two of the group consisting of L a1 to L a1297 , and the L b is optionally selected from any one of the group consisting of L b1 to L b322 ; when the metal complex has the structure of Ir(L a )2(L c ), the L a is the same or different each time it appears and is optionally selected from any one or any two of the group consisting of L a1 to L a1297 , and the L c is optionally selected from any one of the group consisting of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )(L c )2, the L a is optionally selected from any one of the group consisting of L a1 to L a1297 , and the L c is the same or different each time it appears and is optionally selected from any one of the group consisting of L c1 to Lc231 Any one or any two of the components in the group.

[0222] According to an embodiment of the present invention, wherein the metal complex is an Ir complex and has a structure shown by any one of Ir(L a )(L b )(L c ), Ir(L a )2(L b ), Ir(L a )2(L c ), and Ir(L a )(L c )2; when the metal complex has the structure of Ir(L a )(L b )(L c ), the L a is selected from any one of the group consisting of L a1 to L a1342 , the L b is selected from any one of the group consisting of L b1 to L b322 , and the L c is selected from any one of the group consisting of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )2(L b ), the L a is the same or different each time it appears and is selected from any one or any two of the group consisting of L a1 to L a1342 , and the L b is selected from any one of the group consisting of L b1 to L b322 ; when the metal complex has the structure of Ir(L a )2(L c ), the L a is the same or different each time it appears and is selected from any one or any two of the group consisting of L a1 to L a1342 , and the L c is selected from any one of the group consisting of L c1 to L c231 ; when the metal complex has the structure of Ir(L a )(L c )2, the L a is selected from any one of the group consisting of L a1 to L a1342 , and the L c is the same or different each time it appears and is selected from the group consisting of L c1to L c231 any one or any two of the group consisting of

[0223] According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 406.

[0224] According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 530; Compounds 1 to 530 have the general formula Ir(L a )2(L b ), wherein the two L a are the same, and L a and L b are respectively selected from the structures listed in the following table:

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] According to an embodiment of the present invention, an electroluminescent device is also disclosed, which includes:

[0233] an anode,

[0234] a cathode,

[0235] and an organic layer disposed between the anode and the cathode, the organic layer contains a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0236] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0237] According to an embodiment of the present invention, the electroluminescent device emits red light.

[0238] According to an embodiment of the present invention, the electroluminescent device emits white light.

[0239] According to an embodiment of the present invention, in the device, the light-emitting layer further includes at least one host material.

[0240] In one embodiment of the present invention, in the device, the at least one host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0241] In one embodiment of the present invention, in the device, the host material may be a conventional host material in the prior art. For example, but not limited to, the following host materials may be typically included:

[0242]

[0243] In another embodiment of the present invention, a compound combination is also disclosed, which comprises a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0244] In combination with other materials

[0245] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0246] The materials described herein as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be combined with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0247] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0248] Material synthesis example:

[0249] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0250] Synthesis Example 1: Synthesis of Compound 63

[0251] Step 1: Synthesis of intermediate 3

[0252]

[0253] 1,6,7-Trichloroisoquinoline (Intermediate 1, 4.3 g, 14.2 mmol), Intermediate 2 (3.3 g, 14.2 mmol), Pd(PPh3)4 (809 mg, 0.7 mmol) and Na2CO3 (2.3 g, 21.3 mmol) were mixed in Dioxane / H2O (56 mL / 14 mL), replaced with nitrogen, and reacted at 80°C overnight. After TLC detection of the reaction was complete, it was cooled to room temperature, diluted with ethyl acetate, extracted, and the organic phase was concentrated and purified by column chromatography to obtain Intermediate 3 (3.4 g).

[0254] Step 2: Synthesis of intermediate 4

[0255]

[0256] Intermediate 3 (3.4 g, 9 mmol), CuBr (129 mg, 0.9 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (TMDH, 1.33 g, 7.2 mmol) and Cs2CO3 (7.33 g, 22.5 mmol) were mixed in DMF (90 mL). After purging with nitrogen, the mixture was reacted at 135 °C for 5 h. After cooling to room temperature, water was added thereto, and the product precipitated. It was filtered out, and the filter cake was washed with an appropriate amount of water and PE, dried, and then refluxed in EtOH for three hours and filtered to obtain Intermediate 4 (2.6 g).

[0257] Step 3: Synthesis of Intermediate 5

[0258]

[0259] Intermediate 4 (2.6 g, 7.63 mmol), Pd2(dba)3 (137.4 mg, 0.15 mmol), tBuDavePhos (307.3 mg, 0.9 mmol, 6 mol%) and LiOAc (2.52 g, 38.2 mmol) were mixed in DMF (24 mL). After purging with nitrogen, TMS-TMS (2.22 g, 15.2 mmol) and H2O (275 mg, 15.3 mmol) were added thereto, and the mixture was reacted at 100 °C overnight. After cooling, water was added to the reaction solution, and it was extracted with EA. The organic phase was collected, and the residue after concentration was purified by column chromatography to obtain Intermediate 5 (2.4 g).

[0260] Step 4: Synthesis of Iridium Dimer 6

[0261]

[0262] Intermediate 5 (1.8 g, 4.75 mmol) and IrCl3·3H2O (465 mg, 1.32 mmol) were mixed in ethoxyethanol (27 mL) and water (9 mL). After purging with nitrogen, the mixture was refluxed at 130 °C for 24 h. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 6, which could be directly used in the next step without further purification.

[0263] Step 5: Synthesis of Compound 63

[0264]

[0265] The iridium dimer 6 prepared in Step 4 was mixed with 3,7 - diethyl - 3,7 - dimethyl - 4,6 - nonanedione (476 mg, 1.98 mmol), K2CO3 (912 mg, 6.6 mmol) and ethoxyethanol (36 mL) in a 100 - mL single - necked flask. After purging with nitrogen, the mixture was reacted overnight at 45 °C. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed into a 250 - mL flask with DCM. EtOH (about 10 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. A solid was seen to precipitate, which was filtered out and then washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product compound 63 (300 mg). The product was confirmed to be the target product with a molecular weight of 1186.5.

[0266] Synthesis Example 2: Synthesis of Compound 38

[0267] Step 1: Synthesis of Iridium Dimer 8

[0268]

[0269] Intermediate 7 (400 mg, 1.1 mmol) and IrCl3·3H2O (113 mg, 0.32 mmol) were mixed in ethoxyethanol (6 mL) and water (2 mL). After purging with nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 8, which could be directly used in the next step without further purification.

[0270] Step 2: Synthesis of Compound 38

[0271]

[0272] The iridium dimer 8 prepared in Step 1 was mixed with 3,7 - diethyl - 3 - methylnonane - 4,6 - dione (289 mg, 1.28 mmol), K2CO3 (442 mg, 3.2 mmol) and ethoxyethanol (6 mL) in a 100 - mL single - necked flask. After purging with nitrogen, the mixture was reacted overnight at 45 °C. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed into a 250 - mL flask with DCM. EtOH (about 10 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. A solid was seen to precipitate, which was filtered out and then washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product compound 38 (100 mg). The product was confirmed to be the target product with a molecular weight of 1140.5.

[0273] Synthesis Example 3: Synthesis of Compound 260

[0274] Step 1: Synthesis of Iridium Dimer 10

[0275]

[0276] Intermediate 9 (156 mg, 0.35 mmol) and IrCl3·3H2O (41 mg, 0.11 mmol) were mixed in ethoxyethanol (3 mL) and water (1 mL). After purging with nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 10, which could be directly used in the next step without further purification.

[0277] Step 2: Synthesis of Compound 260

[0278]

[0279] Iridium dimer 10 prepared in Step 1, 3,7-diethyl-3-methylnonane-4,6-dione (37.4 mg, 0.17 mmol), K2CO3 (76 mg, 0.55 mmol) and ethoxyethanol (5 mL) were mixed in a 100 mL single-necked flask. After purging with nitrogen, the mixture was reacted at 45 °C overnight. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed into a 250 mL flask with DCM. EtOH (about 10 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. A solid was precipitated and filtered out, and then washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain product Compound 260 (40 mg). The product was confirmed to be the target product with a molecular weight of 1308.7.

[0280] Synthesis Example 4: Synthesis of Compound 192

[0281] Step 1: Synthesis of Iridium Dimer 12

[0282]

[0283] Intermediate 11 (1.4 g, 3.12 mmol) and IrCl3·3H2O (400 mg, 1.13 mmol) were mixed in ethoxyethanol (27 mL) and water (9 mL). After purging with nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 12, which could be directly used in the next step without further purification.

[0284] Step 2: Synthesis of Compound 192

[0285]

[0286] The iridium dimer 12 prepared in Step 1 was mixed with 3,7 - diethyl - 1,1,1 - trifluoro - nonane - 4,6 - dione (452 mg, 1.7 mmol), K2CO3 (781 mg, 5.65 mmol) and ethoxyethanol (25 mL) in a 100 - mL single - necked flask. After purging with nitrogen, the reaction was carried out overnight at room temperature. After monitoring the completion of the reaction by TLC and cooling to room temperature, the reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed into a 250 - mL flask with DCM. EtOH (about 10 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. Solid precipitation was visible, and it was filtered out and then washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product compound 192 (167 mg). The product was confirmed to be the target product with a molecular weight of 1352.6.

[0287] Synthesis Example 5: Synthesis of Compound 278

[0288] Step 1: Synthesis of Iridium Dimer 14

[0289]

[0290] Intermediate 13 (100 mg, 0.26 mmol) and IrCl3·3H2O (35 mg, 0.1 mmol) were mixed in ethoxyethanol (3 mL) and water (1 mL). After purging with nitrogen, the reaction was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 14, which could be directly used for the next step without further purification.

[0291] Step 2: Synthesis of Compound 278

[0292]

[0293] The iridium dimer 14 prepared in Step 1 was mixed with 3,7 - diethyl - 3 - methyl - nonane - 4,6 - dione (50 mg, 0.22 mmol), K2CO3 (70 mg, 0.5 mmol), ethoxyethanol (2 mL) and DMF (2 mL) in a 100 - mL single - necked flask. After purging with nitrogen, the reaction was carried out overnight at 50 °C. After monitoring the completion of the reaction by TLC and cooling to room temperature, the reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed into a 50 - mL flask with DCM. EtOH (about 2 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. Solid precipitation was visible, and it was filtered out and then washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product compound 278 (3 mg). The product was confirmed to be the target product with a molecular weight of 1170.5.

[0294] Synthesis Example 6: Synthesis of Compound 256

[0295] Step 1: Synthesis of Intermediate 16

[0296]

[0297] Mix Intermediate 15 (2.33 g, 5.67 mmol), Pd2(dba)3 (201 mg, 0.22 mmol), tBuDavePhos (450 mg, 1.32 mmol) and LiOAc (1.88 g, 28.4 mmol) in DMF (19 mL). After displacing nitrogen, add hexamethyldigermane (2.4 g, 10.2 mmol) and H2O (205 mg, 11.4 mmol) thereto and react at 135 °C overnight. After cooling, add water to the reaction solution, filter out the precipitated product, dissolve it with EA, and purify the concentrated crude product by column chromatography to obtain Intermediate 16 (1.4 g).

[0298] Step 2: Synthesis of Iridium Dimer 17

[0299]

[0300] Mix Intermediate 16 (1.4 g, 2.8 mmol) and IrCl3·3H2O (395 mg, 1.12 mmol) in ethoxyethanol (27 mL) and water (9 mL). After displacing nitrogen, reflux and react at 130 °C for 24 hours. After the reaction is cooled to room temperature, concentrate to remove the solvent to obtain iridium dimer 17, which can be directly used for the next step without further purification.

[0301] Step 3: Synthesis of Compound 256

[0302]

[0303] Mix the iridium dimer 17 prepared in Step 3, 3,7-diethyl-3-methylnonane-4,6-dione (380 mg, 1.68 mmol), K2CO3 (774 mg, 5.6 mmol) and ethoxyethanol (25 mL) in a 100 mL single-necked flask. After displacing nitrogen, react overnight at 45 °C. After monitoring the reaction to completion by TLC, cool to room temperature. Filter the reaction solution through diatomaceous earth, wash the filter cake with an appropriate amount of EtOH, dissolve the crude product with DCM, add EtOH (about 10 mL) thereto, spin off DCM at room temperature, and a solid will precipitate. Filter it out, wash it with an appropriate amount of EtOH again, and purify the crude product by column chromatography to obtain product Compound 256 (150 mg). The product is confirmed to be the target product by NMR, and the molecular weight is 1404.5.

[0304] Synthesis Example 7: Synthesis of Compound 321

[0305] Step 1: Synthesis of Iridium Dimer 19

[0306]

[0307] Intermediate 19 (210 mg, 0.47 mmol) was mixed with IrCl3·3H2O (56 mg, 0.16 mmol) in ethoxyethanol (3.9 mL) and water (1.3 mL). After displacing nitrogen, the mixture was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was concentrated to remove to obtain iridium dimer 19, which could be directly used for the next step without further purification.

[0308] Step 2: Synthesis of Compound 321

[0309]

[0310] The iridium dimer 19 prepared in Step 3 was mixed with 3,7 - diethyl - 3,7 - dimethylnonane - 4,6 - dione (56 mg, 0.23 mmol), K2CO3 (110 mg, 0.8 mmol) and ethoxyethanol (5 mL) in a 100 mL single - necked flask. After displacing nitrogen, the mixture was reacted overnight at 45 °C. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was dissolved in DCM, and EtOH (about 2 mL) was added thereto. DCM was removed by rotary evaporation at room temperature, and a solid was precipitated. It was filtered out and washed with an appropriate amount of EtOH. The crude product was purified by column chromatography to obtain the product Compound 321 (50 mg). The product was confirmed as the target product by NMR, with a molecular weight of 1322.7.

[0311] Synthesis Example 8: Synthesis of Compound 28

[0312] Step 1: Synthesis of Compound 28

[0313]

[0314] Iridium dimer 6 (0.67 mmol) was mixed with 3,7 - diethyl - 1,1,1 - trifluorononane - 4,6 - dione (535 mg, 2 mmol), K2CO3 (926 mg, 6.7 mmol) and ethoxyethanol (36 mL) in a 100 mL single - necked flask. After displacing with nitrogen, the mixture was reacted overnight at 45 °C. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed with DCM until dissolved, and EtOH (about 5 mL) was added thereto. DCM was removed by rotary evaporation at room temperature, and a solid was precipitated. It was filtered out and washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product Compound 28 (240 mg). The product was confirmed as the target product, with a molecular weight of 1212.4.

[0315] Synthesis Example 9: Synthesis of Compound 416

[0316] Step 1: Synthesis of Intermediate 21

[0317]

[0318] Add intermediate 20 (8.38 g, 20.8 mmol), Pd(OAc)2 (234 mg, 1.04 mmol), tBu3P.BF4 (603 mg, 2.08 mmol), K2CO3 (5.75 g, 41.58 mmol) and DMAc into a reaction flask. After displacing nitrogen, react overnight at 135 °C. Monitor the reaction by TLC until completion, cool to room temperature, dilute with water, extract three times with EA, combine the organic phases, dry, concentrate, and separate by column chromatography to obtain intermediate 21 (2.67 g).

[0319] Step 2: Synthesis of Intermediate 22

[0320]

[0321] Add intermediate 21 (2.18 g, 6.8 mmol), bis(pinacolato)diboron (3.45 g, 13.6 mmol), Pd(OAc) 2 (76 mg, 0.36 mmol), Cy3P·BF4 (250 mg, 0.27 mmol), KOAc (2.0 g, 20.4 mmol) and 1,4-dioxane (13 mL) into a reaction flask. After displacing nitrogen, react overnight at 105 °C. Monitor the reaction by TLC until completion, cool to room temperature, add water to the reaction system, extract the aqueous phase with EA, combine the organic phases, dry, rotary evaporate to remove the solvent, and purify by column chromatography to obtain intermediate 22 (1.68 g).

[0322] Step 3: Synthesis of Intermediate 23

[0323]

[0324] Mix intermediate 1 (780 mg, 3.31 mmol), intermediate 22 (1.37 g, 3.31 mmol), Pd(PPh3)4 (192 mg, 0.16 mmol) and Na2CO3 (0.53 g, 4.97 mmol) in 1,4-Dioxane / H2O (28 mL / 7 mL). After displacing nitrogen, react overnight at 80 °C. After detecting the reaction is complete by TLC, cool it to room temperature, dilute with EA, extract with water, collect the organic phase, concentrate and then separate by column chromatography to obtain intermediate 23 (0.72 g).

[0325] Step 4: Synthesis of Intermediate 24

[0326]

[0327] Intermediate 23 (0.95 g, 1.97 mmol) and Cs2CO3 (1.6 g, 4.91 mmol) were mixed in DMF (20 mL). After displacing nitrogen, the mixture was reacted at 135 °C for 1 hour. After the reaction was complete, it was cooled to room temperature. Water was added thereto, and the product precipitated. It was filtered, and the filter cake was washed with an appropriate amount of water and petroleum ether and dried to obtain Intermediate 24 (0.86 g).

[0328] Step 5: Synthesis of Intermediate 25

[0329]

[0330] Intermediate 24 (0.94 g, 2.1 mmol), neopentylboronic acid (0.49 g, 4.2 mmol), Pd2(dba)3 (48 mg, 0.05 mmol), SPhos (86 mg, 0.21 mmol) and K3PO4 (1.68 g, 6.3 mmol) were mixed in toluene (25 mL). After displacing nitrogen, the mixture was reacted at 110 °C overnight. Monitored by TLC until the reaction was complete, cooled to room temperature, concentrated and purified by column chromatography to obtain Intermediate 25 (0.7 g).

[0331] Step 6: Synthesis of Iridium Dimer 26

[0332]

[0333] A mixture of Intermediate 25 (1.0 g, 2.07 mmol), iridium(III) chloride trihydrate (240 mg, 0.68 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was placed in a high-pressure reactor and reacted at 160 °C for 24 hours. After cooling to room temperature, the red solid iridium dimer 26 was obtained by filtration and could be directly used for the next reaction without purification.

[0334] Step 7: Synthesis of Compound 416

[0335]

[0336] The iridium dimer 26 prepared in Step 6 was mixed with 3,7 - diethyl - 1,1,1 - trifluoro - nonane - 4,6 - dione (0.26 g, 1.0 mmol) and potassium carbonate (0.47 g, 3.4 mmol) in ethoxyethanol (15 mL). After displacing nitrogen, the reaction was carried out at 40 °C for 24 hours. The reaction solution was filtered through diatomaceous earth and the filter cake was washed with ethanol. Then the crude product was dissolved in DCM, ethanol (5 mL) was added thereto, DCM was removed by rotary evaporation at room temperature, and a solid was precipitated. It was filtered out and washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain the product compound 416 (80 mg). The product was confirmed to be the target product with a molecular weight of 1420.6.

[0337] Synthesis Example 10: Synthesis of Compound 470

[0338] Step 1: Synthesis of Iridium Dimer 28

[0339]

[0340] Intermediate 27 (110 mg, 0.25 mmol) was mixed with IrCl3·3H2O (35 mg, 0.1 mmol) in ethoxyethanol (6 mL) and water (2 mL). After displacing nitrogen, the reaction was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the solvent was removed by concentration to obtain iridium dimer 28, which could be directly used for the next step without further purification.

[0341] Step 2: Synthesis of Compound 470

[0342]

[0343] The iridium dimer 28 prepared in Step 2 was mixed with 3,7 - diethyl - 3,7 - dimethyl - nonane - 4,6 - dione (36 mg, 0.15 mmol), K2CO3 (69 mg, 0.5 mmol) and ethoxyethanol (5 mL) in a 100 - mL single - necked flask. After displacing nitrogen, the reaction was carried out overnight at 45 °C. After monitoring the reaction to completion by TLC, it was cooled to room temperature. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, the crude product was dissolved in DCM, EtOH (about 2 mL) was added thereto, DCM was removed by rotary evaporation at room temperature, and a solid was precipitated. It was filtered out and washed with an appropriate amount of EtOH. The crude product was purified by column chromatography to obtain the product compound 470 (30 mg). The product was confirmed to be the target product by NMR with a molecular weight of 1282.6.

[0344] Those skilled in the art should be aware that the above - mentioned preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0345] Device Example

[0346] Device Example 1

[0347] First, a glass substrate having a 120 nm thick indium tin oxide (ITO) anode is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. Then the substrate is mounted on a substrate holder and loaded into a vacuum chamber. The following specified organic layers are sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / second under a vacuum of about 10 -8 Torr. Compound HI is used as the hole injection layer (HIL), with a thickness Compound HT is used as the hole transport layer (HTL), with a thickness Compound EB is used as the electron blocking layer (EBL), with a thickness Then, Compound 63 of the present invention is doped in the host compound RH as the emitting layer (EML, weight ratio 2:98), with a thickness Compound HB is used as the hole blocking layer (HBL), with a thickness On the HBL, Compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as the electron transport layer (ETL), with a thickness Finally, 1 nm thick Liq is deposited as the electron injection layer, and 120 nm of Al is deposited as the cathode. Then the device is transferred back to the glove box and encapsulated with a glass cover and a desiccant to complete the device.

[0348] Device Comparative Example 1

[0349] Device Comparative Example 1 is prepared in the same manner as Device Example 1, except that Compound RD-A is used instead of Compound 63 of the present invention in the emitting layer (EML).

[0350] Device Comparative Example 2

[0351] Device Comparative Example 2 is prepared in the same manner as Device Example 1, except that Compound RD-B is used instead of Compound 63 of the present invention in the emitting layer (EML).

[0352] Device Example 2

[0353] Device Example 2 is prepared in the same manner as Device Example 1, except that Compound 28 is used instead of Compound 63 of the present invention in the emitting layer (EML).

[0354] Device Example 3

[0355] The preparation method of Device Example 3 is the same as that of Device Example 1, except that in the hole injection layer (HIL), compound HT2 (weight ratio 97:3) doped with compound HT is used instead of compound HI, and in the emitting layer (EML), compound 256 is used instead of the compound 63 of the present invention.

[0356] Device Example 4

[0357] The preparation method of Device Example 4 is the same as that of Device Example 3, except that in the emitting layer (EML), compound 416 is used instead of compound 256 of the present invention.

[0358] The partial layer structures and thicknesses of the devices are shown in the following table. For those in which more than one material is used, different compounds are doped in the recorded weight ratios.

[0359] Table 1 Partial device structures of device examples and comparative examples

[0360]

[0361]

[0362] The structures of the materials used in the devices are shown as follows:

[0363]

[0364] The IVL and lifetime characteristics of the devices were measured. Table 2 shows the maximum emission wavelength (λ 2 ), full width at half maximum (FWHM), driving voltage (V), and external quantum efficiency (EQE) data measured at a current density of 15 mA / cm max and the lifetime (LT97) data measured at a current density of 80 mA / cm 2 .

[0365] Table 2 Device data

[0366]

[0367] From the data in Table 2, it can be clearly seen that the embodiments of the present invention have extremely great performance advantages compared with the comparative examples. Specifically: Although the full width at half maximum (FWHM) of Embodiment 1, Embodiment 2, and Embodiment 3 is slightly wider than that of Comparative Example 2, it should be noted that the FWHM of Comparative Example 2 is already extremely narrow. Therefore, the FWHM of Embodiment 1, Embodiment 2, and Embodiment 3 is also extremely narrow. In addition, based on the very high FWHM level of Comparative Example 1, the FWHM of Embodiment 1 to Embodiment 3 has been further astonishingly narrowed by up to 10 nm, which is very rare, indicating that the compounds disclosed in the present invention can achieve very high saturation luminescence. In addition, the driving voltages of Embodiment 1 to Embodiment 3 have maintained a low voltage level comparable to that of Comparative Example 1, and have been reduced by about 5% compared with Comparative Example 2 (3.64V vs 3.84V, 3.58V vs 3.84V, and 3.65V vs 3.84V). More importantly, other device performances of Embodiment 1 to Embodiment 3, such as efficiency and lifetime, have been comprehensively improved compared with Comparative Example 1 and Comparative Example 2: The external quantum efficiency of Embodiment 1 is nearly 3.7 times that of Comparative Example 2 (24.8% vs 6.73%), and nearly 4.4 times that of Comparative Example 1 (24.8% vs 5.64%); the external quantum efficiency of Embodiment 2 is nearly 3.3 times that of Comparative Example 2 (22.2% vs 6.73%), and more than 3.9 times that of Comparative Example 1 (22.2% vs 5.64%); the external quantum efficiency of Embodiment 3 is nearly 3.8 times that of Comparative Example 2 (25.3% vs 6.73%), and nearly 4.5 times that of Comparative Example 1 (25.3% vs 5.64%), and the improvement amplitude of the device efficiency is very large; the advantages of Embodiment 1 to Embodiment 3 in terms of lifetime are even greater. Embodiment 1 reaches more than 36 times that of Comparative Example 2 (67.00h vs 1.85h), and 20 times that of Comparative Example 1 (67.00h vs 3.30h); Embodiment 2 reaches more than 29 times that of Comparative Example 2 (54h vs 1.85h), and more than 16 times that of Comparative Example 1 (54h vs 3.30h); Embodiment 3 reaches more than 23 times that of Comparative Example 2 (43h vs 1.85h), and 13 times that of Comparative Example 1 (43h vs 3.30h). In addition, the colors of Embodiment 1, Embodiment 2, and Embodiment 3 are all darker red (623nm, 622nm, and 619nm), which can better meet the requirements of red luminescence.In addition, in the case of Example 4 where the emission color is very deep red (669 nm), the full width at half maximum (FWHM) still has a level close to that of Comparative Example 1, and the driving voltage also remains at a relatively low voltage level comparable to that of Comparative Example 1. Additionally, the device efficiency of Example 4 is more than three times that of Comparative Example 1 (18.22% vs 5.64%) and 2.7 times that of Comparative Example 2 (18.22% vs 6.73%). It is very rare to still have such a high device efficiency when the emission wavelength is redshifted by more than 90 nm. More notably, Example 4 has a huge advantage in terms of lifespan, reaching an astonishing 362 h, which is more than 109 times that of Comparative Example 1 and more than 195 times that of Comparative Example 2. The deep red light with such a wavelength in Example 4 has important applications in some special fields, such as medicine and agricultural production, and its extremely long device lifespan is very beneficial for its application prospects. Through the above comparison, it can be clearly seen the excellent performance and good application prospects of the metal complexes disclosed in the present invention.

[0368] Spectral data

[0369] The photoluminescence spectra (PL) data of the compounds of the present invention and comparative compounds were measured using a fluorescence spectrophotometer, model F98, produced by Shanghai Lengguang Technology Co., Ltd. Samples of the examples and comparative examples were respectively prepared into solutions with a concentration of 3×10 -5 mol / L in HPLC-grade dichloromethane, and then excited with light of a wavelength of 500 nm at room temperature (298 K) and their emission spectra were measured. The measurement results are shown in Table 3.

[0370] Table 3 PL data

[0371]

[0372]

[0373] From the data in Table 3, it can be seen that the compounds of the present invention have a redder color compared to the comparative compounds, and the maximum emission wavelengths of the PL are generally redshifted significantly, indicating that the compounds of the present invention can better meet the requirements for red emission in various wavelength ranges from light red to deep red. At the same time, the compounds of the present invention all have a very narrow full width at half maximum, indicating that the compounds of the present invention can achieve very saturated red emission in electroluminescent devices.

[0374] In summary, the compounds disclosed in the present invention can achieve red light emission, have a very narrow full width at half maximum, and can achieve high-saturation luminescence. In addition, when used as luminescent materials in electroluminescent devices, these novel metal complexes can also achieve red light emission of the devices, have a very narrow full width at half maximum, can achieve high-saturation luminescence, can reduce or maintain a low voltage, and at the same time can significantly improve the efficiency and lifespan of the devices, providing more excellent performance, which proves the excellent performance and good application prospects of the metal complexes disclosed in the present invention.

[0375] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be limiting.

Claims

1. A metal complex comprising metal Ir and a ligand L coordinated with the metal Ir a , and has Ir(L a ) m (L b ) n The general formula of L a , L b are respectively the first ligand and the second ligand coordinated with the metal Ir; m is selected from 2, n is selected from 1, and m+n is equal to the oxidation state of the metal Ir; when m is equal to 2, a plurality of L a can be the same or different; the ligand L a Having a structure represented by Formula 1: Wherein, Z1 is selected from N, and Z2 is selected from C; W is selected from N; Each occurrence of ring A and ring C is independently selected from a benzene ring or a naphthalene ring; Each occurrence of ring D is independently selected from a pyridine ring or a pyrimidine ring; Ring B is selected from an indole ring or a azaindole ring; R a 、R b 、R c and R d each independently represents, when it appears each time, mono-substitution, multi-substitution or no substitution; R a 、R b 、R c and R d are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, cyano, and combinations thereof; L b the same or different each time it appears and is selected from the following structures: Wherein, X b and X c selected from O; R i 、R ii 、R iii each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, cyano, and combinations thereof; The substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl means that any one of the groups of alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl is substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, cyano, and combinations thereof.

2. The metal complex according to claim 1, wherein, The said L a in which ring B is selected from indole rings.

3. The metal complex according to claim 1, wherein R a 、R b 、R c and R d each occurrence is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, cyano, and combinations thereof.

4. The metal complex according to claim 1, wherein The L a selects a structure represented by any one of Formula 2 to Formula 4 and Formula 9: Wherein, Z1 is selected from N, and Z2 is selected from C; W is selected from N; A1 - A5 are each independently selected from CR, the same or different, each time they appear a ; B1 - B4, each occurrence of which is the same as or different from one another, is selected from N or CR b ; Each occurrence of C1 - C4 is independently selected from CR c ; D1, each occurrence of which is the same as or different from, is independently selected from CR d , D2, each occurrence of which is the same as or different from, is independently selected from N or CR d ; R a 、R b 、R c 、R d Each occurrence is the same as or different from and is independently 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, cyano, and combinations thereof.

5. The metal complex according to claim 4, wherein L a select a structure represented by Formula 2, Formula 3, or Formula 9.

6. The metal complex according to claim 4, wherein, L a Select a structure represented by Formula 2 or Formula 3.

7. The metal complex according to claim 4, wherein In Formula 2 to Formula 4, and Formula 9, Z1 is N and D2 is N.

8. The metal complex according to claim 4, wherein In Formulas 2 to 4 and Formula 9, each of A1 - A5 is independently selected from CR a , each of B1 - B4 is independently selected from CR b ; in Formulas 2 to 4 and Formula 9, each of C1 - C4 is independently selected from CR c ; in Formulas 2 to 4 and Formula 9, each of D1 - D2 is independently selected from CR d ; said R a , R b , R c and R d are the same or different each time they appear and are 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 aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, cyano, and combinations thereof.

9. The metal complex according to claim 8, wherein, Said R a , R b , R c and R d is the same as or different from each other each time it appears and is 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, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, cyano, and combinations thereof.

10. The metal complex according to claim 8, wherein, The R a , R b , R c and R d are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, cyano, and combinations thereof.

11. The metal complex according to claim 4, wherein, In Formulas 2 to 4 and Formula 9, each occurrence of at least one of A1 - A n is the same as or different from one another and is independently selected from CR a , where A n corresponds to the largest serial number among those where A1 - A5 exist in any one of Formulas 2 to 4 and Formula 9; each occurrence of R a is the same as or different from one another and is independently selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, and combinations thereof.

12. The metal complex according to claim 11, wherein, In Formulas 2 to 4 and Formula 9, at least one of A1 - A3 is the same or different each time it appears and is independently selected from CR a .

13. The metal complex according to claim 12, wherein, Said R a Each occurrence is the same or different and is selected from the group consisting of deuterium, fluorine, cyano, benzyl, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, and combinations thereof.

14. The metal complex according to claim 4, wherein, In the formulas 2 to 4 and formula 9, each occurrence of C2 is the same or different and is selected from CR c , and each occurrence of R c is the same or different and is selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, and combinations thereof.

15. The metal complex according to claim 14, wherein, The R c is the same or different each time it appears and is selected from the group consisting of: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.

16. The metal complex according to claim 4, wherein, In Formulae 2 to 4 and Formula 9, at least one of B1 - B n is selected from CR b , and the B n corresponds to the one with the largest serial number among the B1 - B4 existing in any one of Formulae 2 - 4 and Formula 9; and / or, in Formulae 2 to 4 and Formula 9, at least one of D1 - D n is selected from CR d , and the D n corresponds to the one with the largest serial number among the D1 - D2 existing in any one of Formulae 2 - 4 and Formula 9; the R b , R d is the same as or different from each other each time it appears and is 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, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, cyano, and combinations thereof.

17. The metal complex according to claim 16, wherein In Formulas 2 to 4 and Formula 9, B2 and / or B3 are selected from CR b ; in Formulas 2 to 4 and Formula 9, D1 and / or D2 are selected from CR d .

18. The metal complex according to claim 17, wherein The R b , R d is the same as or different from each other each time it appears and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano group, benzyl group, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, trimethylsilyl group, triethylsilyl group, trimethylgermyl group, triethylgermyl group, phenyl group, pyridyl group, triazinyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group, deuterated cyclopentylmethyl group, deuterated cyclohexyl group, deuterated neopentyl group, and combinations thereof.

19. The metal complex according to claim 1, wherein Said L a is the same or different each time it appears and is selected from the group represented by the following structures: Wherein, TMS represents trimethylsilyl and Ph represents phenyl; Among them, optionally, the hydrogen in the structure from L a1 to L a956 , L a987 to L a1009 , L a1020 , L a1022 , L a1105 to L a1230 , L a1243 to L a1244 , L a1298 to L a1301 , L a1304 to L a1309 , L a1312 to L a1342 is partially or completely replaced by deuterium.

20. The metal complex according to claim 1, wherein L b each occurrence being the same or different and being selected from the following structures: Wherein each occurrence of R1–R7 is independently 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, cyano, and combinations thereof.

21. The metal complex according to claim 20, wherein, At least one or two of R1-R3 are selected from 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, or combinations thereof; and / or at least one or two of R4-R6 are selected from 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, or combinations thereof.

22. The metal complex according to claim 20, wherein At least two of R1-R3 are selected from substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2-20 carbon atoms, or combinations thereof.

23. The metal complex according to claim 19, wherein, L b Same or different each time, selected from the group consisting of the following structures:

24. The metal complex according to claim 23, wherein, The metal complex is an Ir complex and has a structure represented by Ir(L a )2(L b ); each occurrence of L a is the same as or different from each other and is selected from any one or any two of the group consisting of L a1 to L a956 , L a987 to L a1009 , L a1020 , L a1022 , L a1105 to L a1230 , L a1243 to L a1244 , L a1298 to L a1301 , L a1304 to L a1309 , L a1312 to L a1342 ; and L b is selected from any one of the group consisting of L b1 to L b322 .

25. The metal complex according to claim 23, wherein, The metal complex is selected from the group consisting of Compounds 1 to 530, and Compounds 1 to 530 have the general formula Ir(L a )2(L b ), where the two L a are the same, and L a and L b correspond to structures selected from those listed in the following table, respectively:

26. An electroluminescent device, comprising: An anode, A cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer contains the metal complex according to any one of claims 1-25.

27. The electroluminescent device according to claim 26, wherein, The organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

28. The electroluminescent device according to claim 26, wherein, The electroluminescent device emits red light or white light.

29. The electroluminescent device according to claim 27, wherein, The light-emitting layer further comprises at least one host material.

30. The electroluminescent device according to claim 29, wherein, The at least one host material contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicofluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

31. A compound combination comprising the metal complex according to any one of claims 1-25.

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