Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a metal complex with a structure as shown in a formula 1. The novel metal complexes can be used as luminescent materials in organic electroluminescent devices, and can provide better device performance, such as narrow half-peak width and higher external quantum efficiency. The invention also discloses an organic electroluminescent device containing the metal complex with the structure shown in the formula 1 and a composition.

Description

Technical Field

[0001] The present invention relates to metal complexes for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a metal complex having a specific formula 1 structure and an organic electroluminescent device and composition 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 a cathode and an 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 light-emitting 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 singlets and triplets, 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 small singlet-triplet energy gaps, making it possible for excitons to return from triplets to singlets. 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 precise structures, small molecules can have large molecular weights. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-group 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 solvents, 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 light-emitting materials. OLEDs can include one or more light-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 color 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] Currently, in the research of blue phosphorescent devices, there are still certain limitations in their full width at half maximum, device efficiency, etc. Therefore, blue phosphorescent materials are worthy of further in-depth research and development. SUMMARY OF THE INVENTION

[0009] The present invention aims to provide a series of metal complexes with the structure of Formula 1 to solve at least part of the above problems. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can provide excellent device performance, such as having a narrow full width at half maximum and a higher external quantum efficiency. These advantages are of great help for improving the level of blue phosphorescent devices.

[0010] According to an embodiment of the present invention, a metal complex with the structure of Formula 1 is disclosed:

[0011]

[0012] Metal M is selected from metals with a relative atomic mass greater than 40;

[0013] Each occurrence of Ring A, Ring B, and Ring D is independently selected from an unsaturated carbocyclic ring having 5 - 30 carbon atoms, an unsaturated heterocyclic ring having 3 - 30 carbon atoms, or a combination thereof; each occurrence of Ring E is independently selected from an unsaturated heterocyclic ring having 1 - 30 carbon atoms;

[0014] Each occurrence of L1 and L2 is independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof; each occurrence of y is independently selected from 1, 2, 3, 4, or 5;

[0015] Each occurrence of K1 - K4 is independently selected from a single bond, O, or S;

[0016] Each occurrence of Z1 - Z3 is independently selected from C or N;

[0017] R has a structure represented by Formula 2:

[0018]

[0019] “*” represents the connection position of Formula 2;

[0020] Each occurrence of T, T1, and T2 is independently selected from C(R t )2, NR t , Si(R t )2, O, S, or Se;

[0021] n is the same as or different from each other when it appears each time, and is selected from 0, 1, 2, 3, 4 or 5;

[0022] Y1 - Y3 is the same as or different from each other when it appears each time, and is selected from CR y , CR y1 or N, and at least one of Y1 - Y3 is CR y1 ;

[0023] Said R y1 is the same as or different from each other when it appears each time, and is selected from the group consisting of: substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof;

[0024] R a , R b , R d , R e is the same as or different from each other when it appears each time, and is represented as mono - substituted, multi - substituted or unsubstituted;

[0025] R’, R a , R b , R d , R e , R t , R y is the same as or different from each other when it appears each time, 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, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0026] Adjacent substituents R’, R a , R b , R d , R e, R t , R y can optionally be connected to form a ring.

[0027] According to an embodiment of the present invention, an organic electroluminescent device is 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 having the structure of Formula 1.

[0028] According to an embodiment of the present invention, a composition is disclosed, which contains the metal complex having the structure of Formula 1.

[0029] The present invention discloses a series of metal complexes having the structure of Formula 1. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can provide excellent device performance, such as having a narrow full width at half maximum and a higher external quantum efficiency. These advantages are extremely helpful for improving the level of blue phosphorescent devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the metal complexes and compositions disclosed herein.

[0031] Figure 2 is a schematic diagram of another organic light-emitting device that can contain the metal complexes and compositions disclosed herein. DETAILED DESCRIPTION

[0032] 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 can also be omitted as needed. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be 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 US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.

[0033] Each of these layers has more instances. For example, U.S. Patent No. 5,844,363, 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, 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., 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, incorporated herein by reference in its entirety. U.S. Patents Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, 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, incorporated herein by reference in its entirety.

[0034] 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 different light-emitting materials to achieve a desired emission spectrum.

[0035] 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.

[0036] The OLED also requires a encapsulation layer, as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included over 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.

[0037] Devices manufactured in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) incorporating the device. Some examples of such 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.

[0038] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0039] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may be present between the first and second layers. For example, even though various organic layers are present between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

[0040] 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.

[0041] When it is believed that a ligand directly contributes to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When it is believed that a ligand does not contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0042] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical 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).

[0043] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely 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 known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of the singlet excited state refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.

[0044] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. 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) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0045] Definition of substituent terms

[0046] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0047] 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.

[0048] Cycloalkyl - as used herein, includes cyclic alkyl groups. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl, 1 - adamantyl, 2 - adamantyl, 1 - norbornyl, 2 - norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0049] 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 heteroalkyl 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.

[0050] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - methylvinyl, styryl, 2,2 - diphenylethylene, 1,2 - diphenylethylene, 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, cycloheptatriene, cyclooctenyl, cyclooctatetraene, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0051] Alkynyl - As used herein, linear alkynyl is encompassed. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0052] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl and m-tetraphenylyl. Additionally, the aryl can be optionally substituted.

[0053] Heterocyclic group - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and 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 can be optionally substituted.

[0054] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable 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, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and their nitrogen - containing analogs. Additionally, the heteroaryl can be optionally substituted.

[0055] Alkoxy - As used herein, it is represented by - O - alkyl, - O - cycloalkyl, - O - heteroalkyl or - O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl 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, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0056] 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.

[0057] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0058] 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.

[0059] 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.

[0060] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0061] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0062] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment 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. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0063] In the present disclosure, unless otherwise defined, when any one of the following terms is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, 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 carboxy, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxy, ester, sulfinyl, sulfonyl and phosphino can be substituted by one or more substituents 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 heterocycloalkyl 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, carboxy, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0064] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.

[0065] In the compounds mentioned in the present disclosure, the 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. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0066] Among the compounds mentioned in the present disclosure, polysubstituted refers to the range including disubstituted up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.

[0067] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, otherwise adjacent substituents in the compounds cannot be connected to form a ring. Among 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 (including spiro ring, bridged ring, fused ring, etc.), and an alicyclic, heteroalicyclic, aromatic 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.

[0068] 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:

[0069]

[0070] 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:

[0071]

[0072] In addition, the expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to the case where, when one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0073]

[0074] According to an embodiment of the present invention, a metal complex having a structure of Formula 1 is disclosed:

[0075]

[0076] In Formula 1,

[0077] the metal M is selected from metals having an atomic mass greater than 40;

[0078] Each occurrence of Ring A, Ring B, and Ring D is the same as or different from each other and is selected from unsaturated carbocycles having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or a combination thereof; each occurrence of Ring E is the same as or different from each other and is selected from unsaturated heterocycles having 1 to 30 carbon atoms;

[0079] Each occurrence of L1 and L2 is the same as or different from each other and is selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; each occurrence of y is the same as or different from each other and is selected from 1, 2, 3, 4, or 5;

[0080] Each occurrence of K1 - K4 is the same as or different from each other and is selected from a single bond, O, or S;

[0081] Each occurrence of Z1 - Z3 is the same as or different from each other and is selected from C or N;

[0082] R has a structure represented by Formula 2:

[0083]

[0084] In Formula 2,

[0085] “*” represents the connecting position of Formula 2;

[0086] Each occurrence of T, T1, and T2 is the same as or different from each other and is selected from C(R t )2, NR t , Si(R t )2, O, S, or Se;

[0087] Each occurrence of n is the same as or different from each other and is selected from 0, 1, 2, 3, 4, or 5;

[0088] Each occurrence of Y1 - Y3 is the same as or different from each other and is selected from CR y , CR y1 or N, and at least one of Y1 - Y3 is CR y1 ;

[0089] Said R y1 Each occurrence is the same as or different from each other and is selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

[0090] R a ,R b ,R d ,R e Each occurrence is the same as or different from the others and represents mono-substitution, multi-substitution or no substitution;

[0091] R’, R a ,R b ,R d ,R e ,R t ,R y Each occurrence is the same as or different from the others 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;

[0092] Adjacent substituents R’, R a ,R b ,R d ,R e ,R t ,R y can optionally be joined to form a ring.

[0093] As used herein, “unsaturated carbocyclic ring” includes aromatic unsaturated carbocyclic rings (aryl rings) and non-aromatic unsaturated carbocyclic rings; “unsaturated heterocyclic ring” includes aromatic unsaturated heterocyclic rings (heteroaryl rings) and non-aromatic unsaturated heterocyclic rings.

[0094] As used herein, “adjacent substituents R’, R a ,R b ,R d ,R e ,R t ,R y"optionally joined to form a ring" is intended to indicate adjacent substituent groups, for example, between two substituents R', between two substituents R a between two substituents R b between two substituents R d between two substituents R e between two substituents R t between two substituents R y between two substituents R a and R', between substituents R b and R', between substituents R d and R', and between substituents R d and R e between, any one or more of these substituent groups may be joined to form a ring. Obviously, these adjacent substituents may also not be joined to form a ring.

[0095] In the present invention, n is the same or different each time it appears and is selected from 0, 1, 2, 3, 4 or 5, and is intended to indicate that the ring containing T, T1 and T2 in Formula 2 is a (n + 4)-membered ring; for example, when n is 0, T1 and T2 in Formula 2 are directly connected, and the structure of Formula 2 at this time is For another example, when n is 2, the structure of Formula 2 at this time is

[0096] According to one embodiment of the present invention, wherein M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt.

[0097] According to one embodiment of the present invention, wherein M is selected from Pt or Pd.

[0098] According to one embodiment of the present invention, wherein M is selected from Pt.

[0099] According to one embodiment of the present invention, wherein the ring A, ring B 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, a heteroaromatic ring having 3 - 30 carbon atoms, or a combination thereof; the ring E is the same or different each time it appears and is selected from an unsaturated heterocyclic ring having 3 - 24 carbon atoms.

[0100] According to one embodiment of the present invention, wherein the ring A, ring B 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 - 18 carbon atoms, a heteroaromatic ring having 3 - 18 carbon atoms, or a combination thereof; the ring E is the same or different each time it appears and is selected from an unsaturated heterocyclic ring having 3 - 18 carbon atoms.

[0101] According to one embodiment of the present invention, each occurrence of ring A, ring B, and ring D is independently selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolocarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof; each occurrence of ring E is independently selected from an imidazolium carbene ring or a benzimidazolium carbene ring.

[0102] According to one embodiment of the present invention, L1 is selected from a single bond, O, S, (CR’R’) y , (SiR’R’) y , NR’, or a combination thereof; y is 1 or 2.

[0103] According to one embodiment of the present invention, L1 is selected from a single bond, O, or S.

[0104] According to one embodiment of the present invention, L1 is selected from a single bond.

[0105] According to one embodiment of the present invention, K1-K4 are selected from a single bond.

[0106] According to one embodiment of the present invention, Z1 is selected from N, and Z2 and Z3 are selected from C.

[0107] According to one embodiment of the present invention, the metal complex has a structure represented by one of Formulas 1-1 to 1-10:

[0108]

[0109]

[0110] In Formulas 1-1 to 1-10,

[0111] Each occurrence of L2 is independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof; each occurrence of y is independently selected from 1, 2, 3, 4, or 5;

[0112] X1-X 20 Are each independently selected from CR x Or N;

[0113] R has a structure represented by Formula 2:

[0114]

[0115] T, T1, and T2 are each independently selected, each time they appear, from C(R t )2, NR t , Si(R t )2, O, S, or Se;

[0116] n is 0, 1, 2, 3, 4, or 5;

[0117] Y1 - Y3 are each independently selected, each time they appear, from CR y , CR y1 , or N, and one of Y1 - Y3 is CR y1 , where the R y1 has a structure represented by Formula 2 - 1:

[0118]

[0119] F1 to F5 are each independently selected from CR f or N; "##" represents the position where Formula 2 - 1 is connected;

[0120] the R', R N , R x , R f , R y , R t , when they appear, are each 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;

[0121] adjacent substituents R', R N , R x , R f , Ry ,R t Optionally joined to form a ring.

[0122] In this embodiment, "adjacent substituents R', R N ,R x ,R f ,R y ,R t can optionally be joined to form a ring" is intended to mean that among adjacent substituent groups, for example, between two substituents R', between two substituents R x ,between two substituents R f ,between two substituents R y ,between two substituents R t ,between two substituents R x and R', and between substituent R x and R N ,any one or more of these substituent groups can be joined to form a ring. Obviously, these adjacent substituents can also not be joined to form a ring.

[0123] According to one embodiment of the present invention, wherein the metal complex has a structure represented by Formula 1-1 or Formula 1-2.

[0124] According to one embodiment of the present invention, wherein the Y2 is selected from CR y1 .

[0125] According to one embodiment of the present invention, wherein the Y3 is selected from CR y1 .

[0126] According to one embodiment of the present invention, wherein the n is selected from 1 or 2.

[0127] According to one embodiment of the present invention, wherein each occurrence of T, T1 and T2 is independently selected from C(R t )2.

[0128] According to one embodiment of the present invention, wherein each occurrence of R t 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 aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0129] According to one embodiment of the present invention, wherein each occurrence of R tEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

[0130] According to one embodiment of the present invention, T1 is selected from C(R t )2, where each R t Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0131] According to one embodiment of the present invention, T1 is selected from C(R t )2, where each R t Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms.

[0132] According to one embodiment of the present invention, T1 is selected from C(R t )2, where each R t Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

[0133] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R t Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0134] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R t Each occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms.

[0135] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R tEach occurrence is the same or different and is selected from the group consisting of: deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

[0136] According to one embodiment of the present invention, T1 and T2 are selected from C(Me)2.

[0137] According to one embodiment of the present invention, wherein each of F1 to F5 is independently selected from CR f .

[0138] According to one embodiment of the present invention, wherein each of Y1 - Y3 is independently selected from CR y or CR y1 , and one of Y1 - Y3 is CR y1 .

[0139] According to one embodiment of the present invention, wherein said R f , R y Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, 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, and combinations thereof.

[0140] According to one embodiment of the present invention, wherein said R f , R y Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxy, mercapto, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, triphenylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

[0141] According to one embodiment of the present invention, wherein F1 to F5 are selected from CH or CD.

[0142] According to one embodiment of the present invention, wherein F1 to F5 are selected from CD.

[0143] According to one embodiment of the present invention, wherein L2 is selected from a single bond, O, S, (SiR’R’) y , NR’, (CR’R’) y, or a combination thereof; y is 1 or 2; each occurrence of R' is the same or different and is independently selected from the group consisting of hydrogen, 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, and combinations thereof.

[0144] According to one embodiment of the present invention, wherein L2 is selected from a single bond, O or S.

[0145] According to one embodiment of the present invention, wherein L2 is selected from O.

[0146] According to one embodiment of the present invention, wherein X1-X 20 are each independently selected from CR x .

[0147] According to one embodiment of the present invention, wherein R x , R', R N each occurrence is the same or different and is independently selected from the group consisting of hydrogen, 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, and combinations thereof.

[0148] According to one embodiment of the present invention, wherein R x , R', R N each occurrence is the same or different and is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

[0149] According to one embodiment of the present invention, wherein R is selected from the group consisting of An-1 to An-63, and the specific structures of An-1 to An-63 are shown in claim 14.

[0150] According to one embodiment of the present invention, the hydrogen in the structures of An-1 to An-63 can be partially or completely replaced by deuterium.

[0151] According to an embodiment of the present invention, wherein the metal complex has the structure of Pt(L a )(L b ), where L a and L b are the first ligand and the second ligand coordinated with the metal Pt respectively, and the L a is selected from the group consisting of L a 1-1 to L a 1-35, L a 2-1 to L a 2-37, and L a 3-1 to L a 3-25, and the L b is selected from the group consisting of L b 1-1 to L b 1-22, L b 2-1 to L b 2-30, L b 3-1 to L b 3-26, L b 4-1 to L b 4-25, and L b 5-1 to L b 5-11, and the specific structures of the L a 1-1 to L a 1-35, L a 2-1 to L a 2-37, L a 3-1 to L a 3-25, L b 1-1 to L b 1-22, L b 2-1 to L b 2-30, L b 3-1 to L b 3-26, L b 4-1 to L b 4-25, and L b 5-1 to L b 5-11 are shown in claim 15.

[0152] According to an embodiment of the present invention, the metal complex is selected from metal complexes Pt1 to Pt308, and the specific structures of the metal complexes Pt1 to Pt308 are shown in claim 15.

[0153] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which comprises:

[0154] An anode,

[0155] A cathode,

[0156] and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a metal complex having the structure of Formula 1, and the metal complex having the structure of Formula 1 is as shown in any of the above embodiments.

[0157] According to an embodiment of the present invention, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

[0158] According to an embodiment of the present invention, wherein the device emits blue light.

[0159] According to an embodiment of the present invention, wherein the device emits white light.

[0160] According to an embodiment of the present invention, wherein the light-emitting layer contains at least one host material.

[0161] According to an embodiment of the present invention, wherein the light-emitting layer contains at least two host materials.

[0162] According to an embodiment of the present invention, wherein the 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, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0163] According to an embodiment of the present invention, wherein the light-emitting layer contains a first host material and a second host material.

[0164] According to an embodiment of the present invention, wherein the first host material has a structure represented by Formula 3:

[0165]

[0166] In Formula 3,

[0167] L 11 is selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;

[0168] Ar 11 is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted amino having 0 - 30 carbon atoms, or a combination thereof;

[0169] R 11 each occurrence is the same or different and represents mono-substituted, multi-substituted or unsubstituted;

[0170] R 11 Each occurrence is the same or different 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, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0171] Adjacent substituents R 11 can optionally be joined to form a ring.

[0172] As used herein, adjacent substituents R 11 can optionally be joined to form a ring, which is intended to mean that two substituents R 11 can be joined to form a ring. Obviously, two substituents R 11 can also not be joined to form a ring.

[0173] According to one embodiment of the present invention, wherein the first host material has a structure represented by Formula 3-1 or Formula 3-2:

[0174]

[0175] L 11 L 12 is selected from a single bond, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;

[0176] Ar 11 is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-30 carbon atoms, or a combination thereof;

[0177] R11 represents, each occurrence being the same or different, mono-substitution, multi-substitution or no substitution;

[0178] R 11 is, each occurrence being the same or different, 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;

[0179] adjacent substituents R 11 can optionally be joined to form a ring.

[0180] According to one embodiment of the present invention, the first host material has a structure represented by Formula 3-3 or Formula 3-4:

[0181]

[0182] Ar 11 is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted amino having 0-30 carbon atoms, or combinations thereof;

[0183] L 11 is selected from a single bond, substituted or unsubstituted arylene having 6-30 carbon atoms, substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or combinations thereof;

[0184] R 11 represents, each occurrence being the same or different, mono-substitution, multi-substitution or no substitution;

[0185] R 11Each 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 having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0186] Adjacent substituents R 11 Can optionally be joined to form a ring.

[0187] According to one embodiment of the present invention, wherein R 11 Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0188] According to one embodiment of the present invention, wherein said R 11 Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted aryl having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, and combinations thereof.

[0189] According to one embodiment of the present invention, wherein said R 11 Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, fluorine, a cyano group, phenyl, biphenyl, triphenylene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzosilole, dibenzosilole, benzothiophene, dibenzothiophene, dibenzoselenophene, and combinations thereof.

[0190] According to one embodiment of the present invention, in Formulas 3-1 to 3-4, there are a plurality of R 11 substituents, and at least one of the plurality of R 11 substituents is a carbazolyl group, for example, one or two of them are carbazolyl groups.

[0191] According to one embodiment of the present invention, in Formulas 3-1 to 3-4, there are a plurality of R 11 substituents, and at least one of the plurality of R 11 substituents and Ar 11 is a carbazolyl group, for example, one or two of them are carbazolyl groups.

[0192] According to one embodiment of the present invention, the first host material is selected from the group consisting of Compound P-1 to Compound P-31:

[0193]

[0194]

[0195]

[0196]

[0197] According to one embodiment of the present invention, the second host material has a structure represented by Formula 4:

[0198]

[0199] In Formula 4,

[0200] Q1 to Q3 are the same or different each time they appear and are selected from CR4 or N, and at least one of Q1 to Q3 is N;

[0201] L is the same or different each time it appears and is selected from the group consisting of: a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, and combinations thereof;

[0202] R1 - R4, each occurrence being the same or different, are 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;

[0203] Adjacent substituents R4 can optionally be joined to form a ring.

[0204] According to one embodiment of the present invention, in Formula 4, Q1 to Q3 are N.

[0205] According to one embodiment of the present invention, wherein said R1 to R4, each occurrence being the same or different, are independently selected from the group consisting of hydrogen, 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, and combinations thereof.

[0206] According to one embodiment of the present invention, wherein the second host material has a structure represented by Formula 4 - 1:

[0207]

[0208] In Formula 4 - 1,

[0209] R1 and R2 are each independently selected from substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms;

[0210] L is selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;

[0211] R L Each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, and a combination thereof.

[0212] According to one embodiment of the present invention, wherein each of said R1 and R2 is independently selected from the group consisting of carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, and a combination thereof.

[0213] According to one embodiment of the present invention, wherein said L is selected from a single bond, phenylene, biphenylene, terphenylene, or pyridinylene.

[0214] According to one embodiment of the present invention, wherein said R L Each occurrence is the same or different and is selected from the group consisting of a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and a combination thereof.

[0215] According to one embodiment of the present invention, wherein said R L Each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms.

[0216] According to one embodiment of the present invention, wherein said R LEach time it appears, it is the same or different and is selected from the group consisting of: phenyl, biphenyl, triphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

[0217] According to one embodiment of the present invention, wherein the second host material is selected from the group consisting of Compound N-2-1 to Compound N-2-45:

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] According to another embodiment of the present invention, a composition is disclosed, which comprises a metal complex having the structure of Formula 1, and the metal complex having the structure of Formula 1 is as shown in any of the above embodiments.

[0224] In combination with other materials

[0225] 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 devices. 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.

[0226] 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 devices. For example, the compounds disclosed herein can be combined with a variety of luminescent 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.

[0227] In the embodiment of material synthesis, unless otherwise specified, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. All reagents not otherwise specified are 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 elaborated in this patent.

[0228] Material synthesis example:

[0229] The preparation method of the metal complex of the present invention is not limited. The following metal complex is typically but not limitedly exemplified, and its synthesis route and preparation method are as follows:

[0230] Synthesis Example 1: Synthesis of Metal Complex Pt11

[0231] Step 1: Synthesis of intermediate 3

[0232]

[0233] Under nitrogen protection, intermediate 1 (1.6 g, 5.5 mmol), intermediate 2 (1.6 g, 8.3 mmol), palladium acetate (62.1 mg, 0.28 mmol), BINAP (345 mg, 0.55 mmol), sodium tert-butoxide (1.1 g, 11.1 mmol) were added to a flask, 30 mL of toluene was added, and the mixture was stirred at 110° C. overnight. After the reaction was completed, intermediate 3 (2.0 g, 5.0 mmol) was obtained by purification by column chromatography.

[0234] Step 2: Synthesis of intermediate 5

[0235]

[0236] Under nitrogen protection, intermediate 3 (2.0 g, 5.0 mmol), intermediate 4 (2.65 g, 6.5 mmol), palladium acetate (44.8 mg, 0.2 mmol), S-Phos (164 mg, 0.4 mmol), and sodium tert-butoxide (960 mg, 10.0 mmol) were added to a flask. 50 mL of xylene was added, and the reaction was heated to 140 °C and stirred overnight. After the reaction was completed, the reaction solution was cooled to room temperature, filtered through diatomaceous earth, and the solvent was removed by concentration under reduced pressure. Then it was purified by column chromatography to obtain intermediate 5 (3.4 g, 4.4 mmol).

[0237] Step 3: Synthesis of intermediate 6

[0238]

[0239] Under nitrogen protection, intermediate 5 (3.4 g, 4.4 mmol), triethyl orthoformate (22.8 g, 153.7 mmol), and concentrated hydrochloric acid (1.1 mL) were added to a flask. The reaction was heated to 100 °C and stirred overnight. After the reaction was completed as detected by TLC, the reaction solution was cooled to room temperature, and the solvent was removed by concentration under reduced pressure. Then it was purified by column chromatography to obtain intermediate 6 (3.2 g, 3.95 mmol).

[0240] Step 4: Synthesis of metal complex Pt11

[0241]

[0242] Under nitrogen protection, intermediate 6 (3.2 g, 3.95 mmol), Ag2O (500.5 mg, 2.16 mmol), and 1,2-dichloroethane (DCE, 40 mL) were added to a flask. The reaction was carried out at room temperature for 12 h. After the reaction was complete, the solvent was removed by concentration under reduced pressure. Then (1,5-cyclooctadiene)platinum(II) dichloride (1.47 g, 3.93 mmol) and 1,2-dichlorobenzene (40 mL) were added thereto. Under argon protection, the reaction was heated to 185 °C and stirred for 24 h. After the reaction was completed, the reaction solution was cooled to room temperature and purified by column chromatography to obtain metal complex Pt11 (1.9 g, 2.0 mmol). The product was identified as the target product with a molecular weight of 968.4.

[0243] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other metal complex structures of the present invention by improving it.

[0244] The preparation method of the electroluminescent device is not limited. The preparation methods in the following embodiments are only examples and should not be construed as limitations. Those skilled in the art can reasonably improve the preparation methods in the following embodiments based on the prior art. Exemplarily, the ratios of various materials in the light-emitting layer are not particularly limited, and those skilled in the art can reasonably select within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer materials, the host material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the host material can account for 85%-99%, and the light-emitting material can account for 1%-15%. In addition, the host material can be one or two materials, and the ratio of the two host materials in the host material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60.

[0245] Device Embodiment

[0246] Device Embodiment 1

[0247] First, clean the glass substrate, which has an indium tin oxide (ITO) anode with a thickness of 80 nm, and then treat it with oxygen plasma and UV ozone. After the treatment, dry the substrate in a glove box to remove moisture. Then mount the substrate on a substrate holder and load it into a vacuum chamber. The following specified organic layers are deposited by thermal vacuum evaporation in sequence on the ITO anode at a rate of 0.2-2 Å / s under a vacuum of about 10 -7 Torr. Compounds HI and HT are co-evaporated and used as the hole injection layer (HIL) with a thickness of Compound HT is used as the hole transport layer (HTL) with a thickness of Compound P-21 is used as the electron blocking layer (EBL) with a thickness of Then, compound P-22 as the first host material, compound N-2-39 as the second host material, and metal complex Pt11 as the dopant are co-evaporated and used as the light-emitting layer (EML) with a thickness of Compound N-2-39 is used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compounds ET and lithium 8-hydroxyquinoline (Liq) are co-evaporated as the electron transport layer (ETL) with a thickness of Finally, deposit A thickness of LiF as the electron injection layer, and deposit Aluminum of thickness as the cathode. Then transfer the device back to the glove box and encapsulate it with a glass cover and a moisture absorbent to complete the device.

[0248] Device Comparative Example 1

[0249] The preparation method of Device Comparative Example 1 is the same as that of Device Example 1, except that metal complex Pt-A is used instead of metal complex Pt11 in the emitting layer (EML).

[0250] Device Comparative Example 2

[0251] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that metal complex Pt-B is used instead of metal complex Pt11 in the emitting layer (EML).

[0252] Table 1 Partial device structures of device examples and comparative examples

[0253]

[0254] The material structures used in the device are as follows:

[0255]

[0256]

[0257] At 10 mA / cm 2 The CIE values, maximum emission wavelength (λ max ), full width at half maximum (FWHM), and external quantum efficiency (EQE) of Example 1 and Comparative Examples 1-2 were measured. To more intuitively show the comparison of the data, the external quantum efficiency of Comparative Example 2 was set to 1.00, and the external quantum efficiencies of Example 1 and Comparative Example 1 were converted relative to the corresponding data of Comparative Example 2. The relevant data are shown in Table 2.

[0258] Table 2 Device data

[0259]

[0260] In Comparative Examples 1-2, comparative metal complexes Pt-A without the specific R y1 substituent of the present invention and comparative metal complex Pt-B without the specific (hetero)alkane ring of the present invention were used as the light-emitting materials. Compared with Comparative Examples 1-2, Example 1 has the same maximum emission wavelength as it, and has a narrower FWHM. The EQEs are increased by 12.4% and 18.0% respectively. The above data prove the advantages of the metal complex with the specific formula 1 structure of the present invention in the device, and it is unexpected that the metal complex of formula 1 of the present invention can greatly improve the EQE of the device under the condition of having a narrower full width at half maximum, which achieves very excellent device performance in blue phosphorescent devices and has potential application potential.

[0261] The above results show that the metal complex of Formula 1 of the present invention can achieve a narrow full width at half maximum and a higher external quantum efficiency when applied in a blue phosphorescent organic light-emitting device, thereby improving the comprehensive performance of the device. These advantages are extremely helpful for improving the level of blue light devices.

[0262] 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 as to why the present invention works are not intended to be limiting.

Claims

1. A metal complex having the structure of Formula 1: In Formula 1, the metal M is selected from metals with a relative atomic mass greater than 40; Ring A, Ring B, and Ring D are each independently selected from unsaturated carbocycles having 5 - 30 carbon atoms, unsaturated heterocycles having 3 - 30 carbon atoms, or a combination thereof; Ring E is each independently selected from unsaturated heterocycles having 1 - 30 carbon atoms; L1 and L2 are each independently selected, each time they appear, the same or differently, from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; y is each independently selected, each time it appears, the same or differently, from 1, 2, 3, 4 or 5; K1 - K4 are each independently selected from a single bond, O, or S; Z1 - Z3 are each independently selected from C or N; R has a structure represented by Formula 2: In Formula 2, "*” represents the connecting position of Formula 2; T, T1, and T2 are each independently selected, each time they appear, from C(R t )2, NR t , Si(R t )2, O, S, or Se; n is each independently selected from 0, 1, 2, 3, 4, or 5; Y1 - Y3, each time it appears, is the same as or different from, and is selected from CR y , CR y1 or N, and at least one of Y1 - Y3 is CR y1 ; Said R y1 is the same or different each time it appears and is selected from the group consisting of: a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; R a ,R b ,R d ,R e each occurrence is the same as or different from the others and is represented as mono-substituted, multi-substituted or unsubstituted; R’, R a , R b , R d , R e , R t , R y each occurrence is the same or different 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, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R’, R a , R b , R d , R e , R t , R y can optionally be linked to form a ring.

2. The metal complex according to claim 1, wherein M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, or Pt; preferably, M is selected from Pt or Pd; more preferably, M is selected from Pt.

3. The metal complex according to claim 1 or 2, wherein Ring A, Ring B, and Ring D are each independently selected from five - membered unsaturated carbocycles, aromatic rings having 6 - 30 carbon atoms, heteroaromatic rings having 3 - 30 carbon atoms, or a combination thereof; Ring E is each independently selected from unsaturated heterocycles having 3 - 24 carbon atoms; Preferably, Ring A, Ring B, and Ring D are each independently selected from five - membered unsaturated carbocycles, aromatic rings having 6 - 18 carbon atoms, heteroaromatic rings having 3 - 18 carbon atoms, or a combination thereof; Ring E is each independently selected from unsaturated heterocycles having 3 - 18 carbon atoms; More preferably, Ring A, Ring B, and Ring D are each independently selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolocarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof; Ring E is each independently selected from an imidazolylidene ring or a benzimidazolylidene ring.

4. The metal complex according to claim 1 or 2, wherein the L1 is selected from a single bond, O, S, (CR’R’) y , (SiR’R’) y , NR’, or a combination thereof; and the y is 1 or 2; Preferably, L1 is selected from a single bond, O, or S; More preferably, L1 is selected from a single bond.

5. The metal complex according to claim 1 or 2, wherein K1 - K4 are selected from a single bond.

6. The metal complex according to claim 1 or 2, wherein Z1 is selected from N, and Z2 and Z3 are selected from C.

7. The metal complex according to claim 1, wherein the metal complex has a structure represented by one of Formula 1 - 1 to Formula 1 - 10: In Formula 1 - 1 to Formula 1 - 10, L2, each occurrence of which is the same as or different from the others, is independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; y, each occurrence of which is the same as or different from the others, is independently selected from 1, 2, 3, 4 or 5; X1-X 20 each independently selected from CR x or N; R has a structure represented by Formula 2: T, T1, and T2 are each independently selected, each time they appear, from C(R t )2, NR t , Si(R t )2, O, S, or Se; n is 0, 1, 2, 3, 4, or 5; Y1 - Y3 are each independently selected from CR, CR or N each time they appear, and one of Y1 - Y3 is CR, where R has the structure represented by Formula 2 - 1: y , CR y1 or N, and one of Y1 - Y3 is CR y1 , said R y1 has the structure represented by Formula 2 - 1: F1 to F5 are each independently selected from CR f or N; "##" represents the position where Formula 2-1 is connected; Said R’, R N , R x , R f , R y , R t when present are the same or different 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, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R’, R N , R x , R f , R y , R t Optionally joined to form a ring; Preferably, the metal complex has a structure represented by Formula 1 - 1 or Formula 1 - 2.

8. The metal complex according to claim 7, wherein Y2 or Y3 is selected from CR y1 ; preferably, Y2 is selected from CR y1 .

9. The metal complex according to claim 1 or 7, wherein n is selected from 1 or 2; Preferably, each occurrence of T, T1 and T2 is the same or different and is selected from C(R t )2, and each occurrence of said R t 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 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, and combinations thereof; More preferably, said R t is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

10. The metal complex according to claim 1 or 7, wherein each occurrence of T1 and / or T2 is the same or different and is selected from C(R t )2, and each occurrence of the R t is the same or different and is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof; More preferably, said R t is the same or different each time it appears and is selected from the group consisting of deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

11. The metal complex according to claim 7, wherein each of F1 to F5 is independently selected from CR f and / or each of Y1 - Y3 is independently selected from CR y or CR y1 , and one of Y1 - Y3 is CR y1 , and each occurrence of said R f , R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, 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, and combinations thereof; Preferably, the R f , R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxy, mercapto, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, triphenylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

12. The metal complex according to claim 1 or 7, wherein L2 is selected from a single bond, O, S, (SiR’R’) y , NR’, (CR’R’) y , or a combination thereof; y is 1 or 2; each occurrence of R’ is the same or different and is selected from the group consisting of hydrogen, 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, and combinations thereof; Preferably, L2 is selected from a single bond, O, or S; More preferably, L2 is selected from O.

13. The metal complex according to claim 7, wherein said X1-X 20 are each independently selected from CR x , Preferably, wherein said R x , R’, R N is the same or different each time it appears and is selected from the group consisting of: hydrogen, 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, and combinations thereof; More preferably, the R x , R', R N 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, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

14. The metal complex according to claim 1 or 7, wherein said R is selected from the group consisting of An-1 to An-63: Among them, Optionally, the hydrogen in An-1 to An-63 may be partially or completely replaced by deuterium.

15. The metal complex according to claim 1, wherein the metal complex has the structure of Pt(L a )(L b ), where L a and L b are the first ligand and the second ligand coordinated with the metal Pt respectively, and the L a is selected from the group consisting of L a 1-1 to L a 1-35, L a 2-1 to L a 2-37, and L a 3-1 to L a 3-25: The "L" mentioned above a In the "L" structure, the "#" indicates a the position where the "L" structure b is connected to "L". wherein the ligand L b selected from the group consisting of L b 1-1 to L b 1-22, L b 2-1 to L b 2-30, L b 3-1 to L b 3-26, L b 4-1 to L b 4-25, and L b 5-1 to L b 5-11: The said L b in the structure indicating the position where the said L b structure is connected to "#" in L a ; Preferably, the metal complex is selected from the group consisting of metal complexes Pt1 to Pt308; the metal complexes Pt1 to Pt308 have the structure represented by Pt(L a )(L b ), and the L a and the L b are respectively selected from the structures shown in the following table:

16. An organic 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 1-15.

17. The organic electroluminescent device according to claim 16, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

18. The organic electroluminescent device according to claim 17, wherein the device emits blue light or white light.

19. The organic electroluminescent device according to claim 17, wherein the light-emitting layer contains at least one host material; preferably, the light-emitting layer contains at least two host materials; more preferably, the 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.

20. A composition, comprising the metal complex according to any one of claims 1-15.

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