Organic electroluminescent material and device thereof

Abstract

An organic electroluminescent material and its device are disclosed. The organic electroluminescent material comprises a metal M and a ligand L having a structure of Formula 1. a A metal complex comprising the metal complex is disclosed, which can be used as a luminescent material in electroluminescent devices. Applying the metal complex to electroluminescent devices can achieve higher current efficiency, power efficiency, external quantum efficiency, and longer device lifetime at low driving voltages, thereby improving the overall performance of the device. An electroluminescent device comprising the metal complex and a compound composition comprising the metal complex are also disclosed.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic electroluminescent devices. More particularly, it relates to an L having the structure of Formula 1. a Metal complexes of ligands, and electroluminescent devices and compound compositions comprising said metal complexes. Background Technology

[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 photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting 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 tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] In recent years, there have been studies and reports on the use of benzoxazole or benzobenzoxazole derivatives as ligands in the synthesis of OLED luminescent materials, for example:

[0009] CN111777646A discloses that has The metal complexes of the general formula and the organic light-emitting devices containing the metal complexes disclosed herein contain a substituted or unsubstituted 2-(phenyl)-naphtho[2,1-D]oxazole skeleton in their ligand structures, but this application does not disclose or teach ligands having other five-membered heterocyclic fused structures, nor does it disclose ligand structures in which substituents R1 or R2 continue to form rings.

[0010] CN105859794A discloses that has The application discloses a general iridium complex and an organic light-emitting device comprising the iridium complex. The application discloses a ligand comprising a substituted or unsubstituted 2-(2-pyridyl)benzoxazole ring skeleton, but does not disclose or teach ligands having other five-membered heterocyclic fused structures, nor does it disclose ligand structures in which the structure linked to benzoxazole is another aromatic ring or heteroaromatic ring.

[0011] Currently developed metal complexes using benzoxazole or benzobenzoxazole derivatives as ligands for electroluminescent devices still have various shortcomings in terms of compound wavelength, device voltage, device efficiency, and device lifetime. To meet the industry's increasing demands, the development of metal complexes that can achieve higher device efficiency and longer device lifetime at low driving voltages remains a pressing need. Summary of the Invention

[0012] The present invention aims to provide a series of novel metal complexes to solve at least some of the above-mentioned problems. The metal complexes comprise a metal M and a ligand L having the structure of Formula 1. a When the metal complex is used as a luminescent material in organic electroluminescent devices, it can achieve high current efficiency, power efficiency, external quantum efficiency, and long device lifetime at low driving voltage, thus providing better device performance.

[0013] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand L coordinated to the metal M. a The metal M is selected from metals with a relative atomic mass greater than 40, and the ligand L... a It has the structure represented by Equation 1:

[0014]

[0015] In this case, A is selected from O or S each time it appears, either the same or different.

[0016] Ring B is selected from fused aromatic rings having 14-30 carbon atoms or fused heteroaromatic rings having 8-30 carbon atoms; and the single ring in ring B that is directly fused with a five-membered ring containing N and A is a six-membered ring.

[0017] R x Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0018] Cy has a structure represented by one of Equations 2-1 to 2-6:

[0019]

[0020] Where Y is selected from O, S, Se, CRR, SiRR or NR, and when two R exist at the same time, the two R are the same or different;

[0021] Y1-Y5 are selected from CR each time they appear, either the same or different. y Or N;

[0022] R x R y R, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0023] Adjacent substituent R x R y R can be arbitrarily connected to form a loop;

[0024] In Equations 2-1 to 2-6, "#" indicates the position where Cy is connected to the metal M. This indicates the position where Cy connects to the quintuple containing N and A in Equation 1.

[0025] According to another embodiment of the present invention, an electroluminescent device is disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex described in the foregoing embodiments.

[0026] According to another embodiment of the present invention, a compound composition comprising the metal complex described in the foregoing embodiments is also disclosed.

[0027] This invention discloses a class of materials comprising a metal M and an L having a structure of Formula 1. a Metal complexes of ligands. When used as luminescent materials in organic electroluminescent devices, these metal complexes can improve the current efficiency, power efficiency, and device lifetime at low driving voltages, thereby enhancing the overall performance of the device. Attached Figure Description

[0028] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound compositions disclosed herein.

[0029] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the metal complexes and compound compositions disclosed herein. Detailed Implementation

[0030] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0031] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0032] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0033] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0034] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation 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 on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0035] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). 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, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0036] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0037] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0038] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0039] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0040] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0041] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0042] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0043] Definition of the term "substituent group"

[0044] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0045] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 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 group may optionally be substituted.

[0046] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0047] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0048] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0049] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0050] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0051] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0052] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. 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 heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0053] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0054] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0055] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0056] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0057] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0058] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0059] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0060] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0061] In this disclosure, unless otherwise defined, the term "substituted alkyl", "substituted cycloalkyl", "substituted heteroalkyl", "substituted heterocyclic", "substituted aralkyl", "substituted alkoxy", "substituted aryl", "substituted alkenyl", "substituted alkynyl", "substituted heteroaryl", "substituted alkylsilyl", "substituted arylsilyl", "substituted alkylgermanium", "substituted arylgermanium", "substituted amino", "substituted acyl", "substituted carbonyl", and "substituted carboxylic acid" are used interchangeably. The substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl groups. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms. Cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, and unsubstituted alkyne groups having 6-30 carbon atoms. Aryl, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof with 0-20 carbon atoms.

[0062] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0063] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0064] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0065] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0066] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0067]

[0068] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0069]

[0070] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0071]

[0072] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0073]

[0074] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand L coordinated to the metal M. a The metal M is selected from metals with a relative atomic mass greater than 40, and the ligand L... a It has the structure represented by Equation 1:

[0075]

[0076] In this case, A is selected from O or S each time it appears, either the same or different.

[0077] Ring B is selected from fused aromatic rings having 14-30 carbon atoms or fused heteroaromatic rings having 8-30 carbon atoms; and the single ring in ring B that is directly fused with a five-membered ring containing N and A is a six-membered ring.

[0078] R x Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0079] Cy has a structure represented by one of Equations 2-1 to 2-6:

[0080]

[0081] Where Y is selected from O, S, Se, CRR, SiRR or NR, and when two R exist at the same time, the two R are the same or different;

[0082] Y1-Y5 are selected from CR each time they appear, either the same or different. y Or N;

[0083] R x R yR, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0084] Adjacent substituent R x R y R can be arbitrarily connected to form a loop;

[0085] In Equations 2-1 to 2-6, "#" indicates the position where Cy is connected to the metal M. This indicates the position where Cy connects to the quintuple containing N and A in Equation 1.

[0086] In this embodiment, "adjacent substituent R" x R y "R can optionally connect to form a ring" is intended to indicate adjacent substituent groups, for example, two substituents R x Between the two substituents R y Between, the two substituents R and R y Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0087] In this paper, "ring B is selected from fused aromatic rings having 14-30 carbon atoms, or fused heteroaromatic rings having 8-30 carbon atoms; and the monocyclic ring in ring B that is directly fused with a five-membered ring containing N and A is a six-membered ring," is intended to indicate that ring B itself is composed of multiple fused rings, ring B is fused with a five-membered ring containing N and A in Formula 1, and the monocyclic ring in ring B that is directly fused with a five-membered ring containing N and A is a six-membered ring (including six-membered aromatic rings or six-membered heteroaromatic rings), as explained in Formula 1':

[0088]

[0089] In Formula 1', the six-membered ring containing B1-B4 is named ring B'. Ring B' is directly fused with a five-membered ring containing N and A. Ring B' is a part of ring B in Formula 1. Ring B' is further fused with other rings through at least one set of B1 and B2, B2 and B3, B3 and B4 to form ring B. Ring B is a fused aromatic ring with 14-30 carbon atoms or a fused heteroaromatic ring with 8-30 carbon atoms.

[0090] According to one embodiment of the present invention, in Formula 1, A is selected from O.

[0091] According to one embodiment of the present invention, ring B is selected from any structure in the group consisting of formulas 1-1 to 1-14:

[0092] In this case, X is selected from O, S, or NR' each time it appears, either the same or different.

[0093] X1 and X2 are both C, and one of X1 and X2 is connected to N in Equation 1, and the other of X1 and X2 is connected to A in Equation 1;

[0094] X3-X 10 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0095] R', R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0096] Adjacent substituents R', R x They can be arbitrarily connected to form a ring.

[0097] In this embodiment, "adjacent substituents R', R x "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R x Between, two adjacent substituents R' and R x Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0098] In this embodiment, "X1 and X2 are both C, and one of X1 and X2 is connected to N in Equation 1, and the other of X1 and X2 is connected to A in Equation 1" is intended to indicate that Equations 1-1 to 1-14 can have different fusion methods. For example, in Equation 1-9, when X1 is connected to N in Equation 1, X2 is connected to A in Equation 1. In this case, the structure of Equation 1-9 is:

[0099]

[0100] At this time, the L a The structure is as follows:

[0101] When X2 is connected to N in Equation 1, and X1 is connected to A in Equation 1, the structure of Equation 1-9 is as follows:

[0102]

[0103] At this time, the L a The structure is as follows:

[0104] In this embodiment, ring B is selected from any one of formulas 1-1 to 1-14. Therefore, formulas 1-1 to 1-14 all satisfy the limiting condition of "fused aromatic rings having 14-30 carbon atoms, or fused heteroaromatic rings having 8-30 carbon atoms". For example, for formulas 1-1 to 1-3, where X is a heteroatom, therefore, X3-X6 are all selected from CR. x When the above-mentioned carbon atom number restriction condition is met, and any one or more of X3-X6 are selected from N, at least two adjacent R atoms in X3-X6... x The formation of rings can also satisfy the aforementioned restrictions on the number of carbon atoms; for example, in formulas 1-4 and 1-5, X3-X8 can all be selected from CR. x At this time, at least two adjacent R values ​​in X3-X8 x The linkage forms a ring to satisfy the above-mentioned carbon number requirement, or one or two of X3-X8 are selected from N, and the rest are selected from C. x If the above-mentioned carbon atom number requirement is met, or if more than one of X3-X8 is selected from N, then at least two adjacent R atoms in X3-X8 must be present. x The formation of rings can also satisfy the aforementioned restrictions on the number of carbon atoms; Equations 1-6 to 1-14 are similar cases. Furthermore, taking Equation 1-9 as an example, there are 14 ring atoms in Equation 1-9, with X1 and X2 fixed as C, and X3-X... 10 If the number of N atoms in Equation 1-9 is greater than 6, then the number of carbon atoms in the fused heteroaromatic ring represented by Equation 1-9 is less than 8, which does not satisfy the restriction that "ring B is selected from a fused heteroaromatic ring with 8-30 carbon atoms". Therefore, in Equation 1-9, "X3-X 10 The case where the number of N atoms is greater than 6 is not the subject of this invention.

[0105] According to one embodiment of the present invention, in formulas 1-1 to 1-3, and formulas 1-6 to 1-14, X3-X 10 Each time it appears, it is selected from CR in the same or different ways. x .

[0106] According to one embodiment of the present invention, in formulas 1-4 to 1-14, X3-X 10 At least one of them is N.

[0107] According to one embodiment of the present invention, R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, cyano groups, and combinations thereof.

[0108] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 15 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0109] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanyl, trifluoromethyl, cyano, partially or fully deuterated methyl, partially or fully deuterated ethyl, partially or fully deuterated propyl, partially or fully deuterated isopropyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated neopentyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated phenyl, partially or fully deuterated pyridyl, partially or fully deuterated trimethylsilyl, and combinations thereof.

[0110] According to one embodiment of the present invention, Cy is selected from any structure of the group consisting of:

[0111]

[0112]

[0113] Where Z is selected from O, S, Se, NR", CR”R", SiR”R” or GeR”R”; when two R” exist at the same time, the two R” are the same or different;

[0114] R yEach occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0115] R y The "R" and "R" are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0116] Adjacent substituent R y "R" can be optionally connected to form a loop;

[0117] Here, "#" indicates the position where Cy is connected to the metal M. This indicates the position where Cy connects to the quintuple containing N and A in Equation 1.

[0118] In this embodiment, "adjacent substituent R" y "R" can optionally connect to form a ring, intended to represent adjacent substituent groups, for example, two adjacent substituents R y Between two adjacent substituents R”, between two adjacent substituents R” and R y Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0119] According to one embodiment of the present invention, R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, cyano groups, and combinations thereof.

[0120] According to one embodiment of the present invention, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 15 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0121] According to one embodiment of the present invention, R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanium, trifluoromethyl, cyano, partially or fully deuterated methyl, partially or fully deuterated ethyl, partially or fully deuterated propyl, partially or fully deuterated isopropyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated neopentyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated phenyl, partially or fully deuterated pyridyl, partially or fully deuterated trimethylsilyl, partially or fully deuterated trimethylgermanium, and combinations thereof.

[0122] According to one embodiment of the present invention, wherein the ligand L a Choose freestyle 3-1 to 3-2 each time it appears, either the same or different.

[0123] The structure represented by Equation 3-4:

[0124]

[0125] Where A is selected from O or S;

[0126] R x R yEach occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0127] R x R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0128] Adjacent substituent R x R y They can be arbitrarily connected to form a ring.

[0129] In this paper, "adjacent substituent R" x R y "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R x Between two adjacent substituents R y Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0130] According to one embodiment of the present invention, wherein the ligand L a It has a structure represented by Equation 3-4.

[0131] According to one embodiment of the present invention, at least one R x and / or at least one R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof.

[0132] According to one embodiment of the present invention, wherein the ligand L a Choose L each time it appears, either the same or different. a1 To L a668 The group consisting of:

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] According to one embodiment of the present invention, wherein the L a1 To L a668 The hydrogen in the structure can be partially or completely replaced by deuterium.

[0158] According to one embodiment of the present invention, the metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0159] Among them, metal M is selected from Ir, Rh, Re, Os, Pt, Au, or Cu; L a L b and L c These are the first, second, and third ligands coordinated with the metal M, respectively; m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, q is selected from 0, 1, or 2, and m+n+q equals the oxidation state of metal M; when m equals 2 or 3, multiple L... a They can be the same or different; when n equals 2, 2 L b They can be the same or different; when q equals 2, there are 2 Ls. c They can be the same or different;

[0160] L a L b and L c They can be selectively linked to form multidentate ligands;

[0161] L b and L c Each occurrence is either identical or different from the group consisting of the following structures:

[0162]

[0163] Among them, R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0164] Xb Each time it appears, select the group consisting of the following, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0165] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0166] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0167] Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0168] In this embodiment, adjacent substituents R a R b R c R N1 R N2 RC1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 Between these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to: or Where W is selected from O, S, Se, NR w or CR w R w ; wherein R w R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.

[0169] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0170] According to one embodiment of the present invention, the metal M is Ir.

[0171] According to one embodiment of the present invention, L bEach occurrence is selected from the following structure, either identically or differently:

[0172]

[0173] R1-R7 are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups, and so on. Alkyne groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0174] Adjacent substituents R1, R2, R3, R4, R5, R6, and R7 can optionally be linked to form a ring.

[0175] In this document, the phrase "adjacent substituents R1, R2, R3, R4, R5, R6, R7 can optionally connect to form a ring" is intended to mean that any one or more of the following substituent groups, such as between substituents R1 and R2, between substituents R1 and R3, between substituents R2 and R3, between substituents R4 and R5, between substituents R4 and R6, between substituents R5 and R6, between substituents R1 and R7, between substituents R2 and R7, between substituents R3 and R7, between substituents R4 and R7, between substituents R5 and R7, and between substituents R6 and R7, can connect to form a ring. It is also apparent that these substituents may not connect to form a ring.

[0176] According to one embodiment of the present invention, L c Each occurrence is either identical or different from the group consisting of the following structures:

[0177] Among them, R a R b and Rc Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0178] R a R b R c Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0179] Adjacent substituent R a R b R c They can be arbitrarily connected to form a ring.

[0180] In this embodiment, adjacent substituents R a R b R c They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, and substituent R b and R c Between these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to: Where W is selected from O, S, Se, NR w or CR w R w ; wherein R w R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.

[0181] According to one embodiment of the present invention, the metal complex has Ir(L) a )2(L b The general formula of ) and has the structure represented by Equation 4:

[0182]

[0183] In this case, A is selected from O or S each time it appears, either identically or differently; R x R y Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0184] R x R y R1-R7, each time appearing, are selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkyne groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups having 3-30 carbon atoms (substituted or unsubstituted), alkylsilyl groups having 3-20 carbon atoms (substituted or unsubstituted), arylsilyl groups having 6-20 carbon atoms (substituted or unsubstituted), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0185] Adjacent substituent R x R y They can be arbitrarily connected to form a loop;

[0186] Adjacent substituents R1-R7 can optionally connect to form a ring.

[0187] According to one embodiment of the present invention, at least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is a substituted or unsubstituted alkyl group having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0188] According to one embodiment of the present invention, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0189] According to one embodiment of the present invention, the metal complex has Ir(L) a ) m (L c ) 3-m The general formula has the structure represented by Equation 5:

[0190]

[0191] Where m is selected from 1, 2, or 3; when m is selected from 1, the two L c Same or different; when m is selected from 2 or 3, multiple L a Same or different;

[0192] A is selected from O or S each time it appears, either identically or differently; R x R y Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0193] R x R y R a1 -R a4 ,R b1 -R b4Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0194] Adjacent substituent R x R y They can be arbitrarily connected to form a loop;

[0195] Adjacent substituent R a1 -R a4 R b1 -R b4 They can be arbitrarily connected to form a ring.

[0196] In this embodiment, "adjacent substituent R" a1 -R a4 ,R b1 -R b4 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, substituent R a1 and R a2 Between, substituent R a2 and R a3 Between, substituent R a3 and R a4 Between, substituent R b1 and R b2 Between, substituent R b2 and R b3 Between, and substituent R b3 and R b4 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0197] According to one embodiment of the present invention, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of them are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0198] According to one embodiment of the present invention, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of the following are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

[0199] According to one embodiment of the present invention, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of them are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof.

[0200] According to one embodiment of the present invention, R x R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, cyano groups, and combinations thereof.

[0201] According to one embodiment of the present invention, R x R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 15 carbon atoms, cyano groups, and combinations thereof.

[0202] According to one embodiment of the present invention, R x R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanium, trifluoromethyl, cyano, partially or fully deuterated methyl, partially or fully deuterated ethyl, partially or fully deuterated propyl, partially or fully deuterated isopropyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated neopentyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated phenyl, partially or fully deuterated pyridyl, partially or fully deuterated trimethylsilyl, partially or fully deuterated trimethylgermanium, and combinations thereof.

[0203] According to one embodiment of the present invention, L b Choose freely L b1 To L b322 Groups formed:

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] According to one embodiment of the present invention, L c Choose freely L c1 To L b321 Groups formed:

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] According to one embodiment of the present invention, the metal complex is an Ir complex and has Ir(L) a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a (L) c Any of the structures shown in )2; when the metal complex has Ir(L a (L) b (L) c When the structure of ) is used, the L a Choose freely L a1 To L a668 Any of the groups formed, the L b Choose freely L b1 To L b322 Any one of the groups, the L c Choose freely L c321 Any one of the groups; when the metal complex has Ir(L a )2(L b When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a1 To L a668 The L is any one or any two of the groups formed. b Choose freely L b1 To L b322 Any one of the groups; when the metal complex has Ir(L a )2(L c When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a1 To L a668 The L is any one or any two of the groups formed.c Choose freely L c321 Any one of the groups; when the metal complex has Ir(L a (L) c When the structure of )2 is used, the L a Choose freely L a1 To L a668 Any of the groups formed, the L c Choose L each time it appears, either the same or different. c321 Any one or any two of the group.

[0221] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds 1 to 510:

[0222] Among them, compounds 1 to 85 have Ir(L a )2(L b The general formula for ), where the two L's a Same, L a and L b These correspond to the structures listed in the table below:

[0223]

[0224]

[0225] Among them, compounds 86 to 510 have Ir(L a (L) c The general formula for )2, where the two L c Same, L a and L c These correspond to the structures listed in the table below:

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex described in any of the preceding embodiments.

[0234] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0235] According to one embodiment of the present invention, the electroluminescent device emits red light, yellow light, green light or white light.

[0236] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound.

[0237] According to one embodiment of the present invention, the light-emitting layer further comprises a second host compound.

[0238] According to one embodiment of the present invention, the first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0239] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 6:

[0240]

[0241] Among them, E1-E6 are selected from C and CR each time they appear, either identically or differently. e Or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and it is connected to the structure represented by formula A;

[0242]

[0243] in,

[0244] When Q appears repeatedly, whether it is the same or different, it is selected from the group consisting of O, S, Se, N, NR”', CR”'R”', SiR”'R”', GeR”'R”' and R”'C=CR”'; when two R”' exist at the same time, the two R”' can be the same or different.

[0245] p is 0 or 1; r is 0 or 1; and p + r = 1;

[0246] L, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0247] Q1-Q8 are selected from C and CR each time they appear, either identically or differently. q Or N;

[0248] When Q is selected from N, p is 0 and r is 1;

[0249] When Q is selected from the group consisting of O, S, Se, NR”', CR”'R”', SiR”'R”', GeR”'R”' and R”'C=CR”', p is 1 and r is 0; at this time, one of Q1-Q8 is C;

[0250] R e ,R”' and R q Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0251] "*" represents the connection position between Equation A and Equation 6;

[0252] Adjacent substituent R e ,R”',R q They can be connected into a ring at will.

[0253] In this embodiment, "adjacent substituent R" e ,R”',R q"Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R e Between, between the two substituents R”', between the two substituents R q Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0254] According to one embodiment of the present invention, E1-E6 are selected from C, CR each time they appear, either identically or differently. e Or N, and three of E1-E6 are N, and at least one of E1-E6 is CR. e And the R e Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0255] And / or Q is selected from O, S, N or NR each time it appears, either the same or different.

[0256] And / or at least one or at least two of Q1-Q8 are selected from CR q And the R q Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 5-30 carbon atoms, or combinations thereof;

[0257] And / or L, each time appearing, is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0258] According to one embodiment of the present invention, the first host compound is selected from the group consisting of:

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 7:

[0280]

[0281] in,

[0282] L x Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0283] V is selected from C and CR each time it appears, either identically or differently. v Or N, and at least one of V is C, and with L x connect;

[0284] U is selected from C, CR each time it appears, either identically or differently. u Or N, and at least one of U is C, and with L x connect;

[0285] R v and R uEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0286] Ar6, each time it appears, is selected from the same or different aryl groups with 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 3-30 carbon atoms (substituted or unsubstituted), or combinations thereof.

[0287] Adjacent substituent R v and R u They can be arbitrarily connected to form a ring.

[0288] In this embodiment, "adjacent substituent R" v and R u "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R v Between two adjacent substituents R u Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0289] According to one embodiment of the present invention, the second host compound has a structure represented by one of formulas 7-a to 7-j:

[0290]

[0291]

[0292] According to one embodiment of the present invention, the second host compound is selected from the group consisting of:

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] According to one embodiment of the present invention, in the light-emitting layer, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0305] According to one embodiment of the present invention, the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

[0306] According to one embodiment of the present invention, a compound composition comprising the metal complex described in any of the foregoing embodiments is disclosed.

[0307] Combination with other materials

[0308] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0309] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0310] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0311] Material synthesis examples:

[0312] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0313] Synthesis Example 1: Synthesis of Compound 173

[0314] Step 1: Synthesis of Intermediate 1

[0315]

[0316] 500 mL of xylene was placed in a 1 L three-necked flask, followed by the sequential addition of 2-amino-6-bromophenol (19.8 g, 105.3 mmol), benzoyl chloride (14.8 g, 105.3 mmol), and pyridine (8.3 g, 105.3 mmol). The reaction was carried out at room temperature for 1 hour. After the reaction was confirmed to be complete by TLC, p-toluenesulfonic acid (80.1 g, 421.2 mmol) was added, and the mixture was heated to 145 °C and reacted overnight. After the reaction was completed, the mixture was cooled to room temperature, neutralized with saturated sodium bicarbonate aqueous solution, extracted with ethyl acetate, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give intermediate 1 (15.0 g, yield 52%).

[0317] Step 2: Synthesis of Intermediate 2

[0318]

[0319] Intermediate 1 (15.0 g, 54.7 mmol), 2-formylphenylboronic acid (9.0 g, 60.2 mmol), tetrakis(triphenylphosphine)palladium (3.2 g, 2.7 mmol), sodium carbonate (14.5 g, 136.8 mmol), and toluene / ethanol / water (180 mL / 45 mL / 45 mL) were added sequentially to a 500 mL three-necked flask. After purging with nitrogen, the mixture was reacted at 100 °C for 12 hours. After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate, washed with saturated brine, and the organic phase was collected. The mixture was concentrated under reduced pressure and purified by column chromatography to obtain intermediate 2 (15.0 g, 92% yield).

[0320] Step 3: Synthesis of Intermediate 3

[0321]

[0322] Intermediate 2 (15.0 g, 50.2 mmol), (methoxymethyl)triphenylphosphine chloride (25.8 g, 75.3 mmol), and tetrahydrofuran (250 mL) were added sequentially to a 500 mL three-necked flask. Potassium tert-butoxide (8.5 g, 75.3 mmol) was added in portions to the reaction system at 0 °C. The mixture was then brought to room temperature and reacted overnight. After the reaction was confirmed to be complete by TLC, water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain intermediate 3 (8.6 g, 53% yield).

[0323] Step 4: Synthesis of Intermediate 4

[0324]

[0325] Intermediate 3 (8.6 g, 26.4 mmol), bismuth trifluoromethanesulfonate (0.9 g, 1.4 mmol), and 1,2-dichloroethane (DCE) (200 mL) were added sequentially to a 500 mL three-necked flask. After purging with nitrogen, the mixture was reacted at 60 °C for 12 hours. After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography to obtain intermediate 4 (6.4 g, yield 82%).

[0326] Step 5: Synthesis of Compound 173

[0327]

[0328] Intermediate 5 (3.0 g, 3.6 mmol), intermediate 4 (1.6 g, 5.5 mmol), 2-ethoxyethanol (40 mL), and DMF (40 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 140 h under N2 protection. After cooling, the mixture was concentrated under reduced pressure and purified by column chromatography to give compound 173 (0.1 g, 3% yield). This product was identified as the target product with a molecular weight of 907.31.

[0329] Synthesis Example 2: Synthesis of Compound 43

[0330] Step 1: Synthesis of Intermediate 6

[0331]

[0332] 85 mL of xylene was placed in a 250 mL three-necked flask, followed by the sequential addition of 2-amino-6-bromophenol (5.0 g, 26.6 mmol), 3,5-dimethylbenzoyl chloride (4.49 g, 26.6 mmol), and pyridine (2.1 g, 26.6 mmol). The reaction was carried out at room temperature for 1 hour. After the reaction was confirmed to be complete by TLC, p-toluenesulfonic acid (20.24 g, 106.4 mmol) was added, and the mixture was heated to 145 °C and reacted overnight. After the reaction was completed, the mixture was cooled to room temperature, neutralized with saturated sodium bicarbonate aqueous solution, extracted with ethyl acetate, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give intermediate 6 (4.1 g, 51% yield).

[0333] Step 2: Synthesis of Intermediate 7

[0334]

[0335] Intermediate 6 (4.1 g, 13.64 mmol), 2-formylphenylboronic acid (2.25 g, 15 mmol), tetrakis(triphenylphosphine)palladium (0.79 g, 0.68 mmol), sodium carbonate (3.61 g, 34.1 mmol), and toluene / ethanol / water (44 mL / 11 mL / 11 mL) were added sequentially to a 250 mL three-necked flask. After purging with nitrogen, the mixture was reacted at 100 °C for 12 hours. After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate, washed with saturated brine, and the organic phase was collected. The mixture was concentrated under reduced pressure and purified by column chromatography to give intermediate 7 (4.3 g, 95% yield).

[0336] Step 3: Synthesis of Intermediate 8

[0337]

[0338] Intermediate 7 (4.6 g, 13.6 mmol), (methoxymethyl)triphenylphosphine chloride (7 g, 20.4 mmol), and tetrahydrofuran (90 mL) were added sequentially to a 250 mL three-necked flask. Potassium tert-butoxide (2.3 g, 20.4 mmol) was added in portions to the reaction system at 0 °C. The mixture was then brought to room temperature and reacted overnight. After the reaction was confirmed to be complete by TLC, water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain intermediate 8 (2.2 g, 45% yield).

[0339] Step 4: Synthesis of Intermediate 9

[0340]

[0341] Intermediate 8 (2 g, 5.63 mmol), bismuth trifluoromethanesulfonate (0.19 g, 0.28 mmol), and dichloroethane (56 mL) were added sequentially to a 250 mL three-necked flask. After purging with nitrogen, the mixture was reacted at 60 °C for 12 hours. After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography to obtain intermediate 9 (0.85 g, yield 47%).

[0342] Step 5: Synthesis of iridium dimer

[0343]

[0344] In a dry 100 mL round-bottom flask, intermediate 5 (0.85 g, 2.6 mmol), iridium trichloride trihydrate (0.26 g, 0.75 mmol), 2-ethoxyethanol (9 mL), and water (3 mL) were added sequentially. The mixture was heated at 130 °C for 24 h under N2 protection. After the reaction cooled, the mixture was filtered, the solid was washed three times with methanol (30 mL), dried under vacuum, and the solid iridium dimer was collected and used directly in the next reaction step.

[0345] Step 6: Synthesis of Compound 43

[0346]

[0347] The iridium dimer obtained in the previous step, 3,7-diethyl-3-methylnonane-4,6-dione (0.25 g, 1.1 mmol), K2CO3 (0.5 g, 3.75 mmol), and ethoxyethanol (12 mL) obtained in the previous step were added to a 100 mL single-necked flask. The flask was placed in a reaction flask, and after purging with nitrogen, it was reacted at 40 °C for 24 hours. The reaction solution was filtered through diatomaceous earth, and the filter cake was washed with an appropriate amount of EtOH. The crude product was washed with DCM (dichloromethane) and transferred to another flask. EtOH was added to the crude product, and the DCM was removed by rotary evaporation at room temperature. A solid precipitated out and was filtered out. The solid was washed with an appropriate amount of EtOH, dried, dissolved in DCM, concentrated, and further purified by column chromatography to obtain compound 43 (0.008 g, yield 1%). This product was identified as the target product with a molecular weight of 1062.39.

[0348] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0349] Determination of the photoluminescence spectrum of compound 43:

[0350] The photoluminescence (PL) spectra of compound 43 in this invention were determined using a Prism F98 fluorescence spectrophotometer manufactured by Shanghai Prism Technology Co., Ltd. Samples of compound 43 were prepared with HPLC-grade toluene solution to a concentration of 1×10⁻⁶. -6 A mol / L solution was prepared, and then excited with light at a wavelength of 500 nm at room temperature (298 K) and its emission spectrum was measured. The emission wavelength λ of the photoluminescence spectrum was recorded. max The full width at half maximum (nm) and full width at half maximum (FWHM) (nm) are shown in Table 1.

[0351] Table 1. Photoluminescence spectral data of compound 43

[0352]

[0353] As can be seen from the data in Table 1, the compound 43, which has a specific heterocyclic derivative of Formula 1 as the main ligand and a diketone derivative as the auxiliary ligand, has an emission wavelength of 539 nm and an extremely narrow full width at half maximum (FWHM) of only 26.1 nm. It can achieve very saturated emission, indicating that the luminescence performance of compound 43 of the present invention is excellent and has the potential to become an excellent yellow-green phosphorescent material.

[0354] Device Examples

[0355] Example 1

[0356] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, deposition was performed sequentially on the ITO anode via thermal vacuum evaporation at a rate of 0.2–2 Å / s. Compound HI was used as the hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound X-4 is used as an electron blocking layer (EBL). Then, compound 173 of the present invention was co-deposited with compounds X-4 and H-91 as an emissive layer (EML, weight ratio 6:47:47). In the EML, compound H-1 acts as a hole-blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL, weight ratio 40:60). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer, and a 120 nm thick layer of aluminum was deposited as the cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and desiccant to complete the device.

[0357] Comparative Example 1

[0358] Comparative Example 1 was prepared in the same manner as Example 1, except that compound YD1 was used instead of compound 173 of the present invention in the light-emitting layer (EML).

[0359] The partial layer structure and thickness of the device are shown in Table 2 below. The device uses more than one material, obtained by doping different compounds in the stated weight ratios.

[0360] Table 2 Partial device structures of Example 1 and Comparative Example 1

[0361]

[0362] The structure of the materials used in the device is shown below:

[0363]

[0364]

[0365] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured, including the maximum emission wavelength λ.max Full width at half maximum (FWHM), voltage efficiency, current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE); at 80 mA / cm² 2 The device lifetime (LT97) was measured; these data were recorded and are shown in Table 3.

[0366] Table 3 Device data for Example 1 and Comparative Example 1

[0367]

[0368] discuss:

[0369] As shown in Table 3, when the compound of the present invention is used as a light-emitting dopant in the device, the maximum emission wavelength of the device is 540 nm, which meets the requirement for emitting yellow-green phosphorescence. Compared with Comparative Example 1, Example 1 has a narrower half-maximum width (WHM) of 4.1 nm, a lower voltage of 0.6 eV, a higher current efficiency of 2.7%, a significantly higher power efficiency of 25.7%, and a substantial increase in external quantum efficiency of 8.6%. More importantly, the device lifetime of Example 1 is increased by 1.6 times. The above data demonstrate that the compound disclosed in this invention has excellent performance.

[0370] In summary, the compounds disclosed in this invention, when applied to electroluminescent devices, can significantly improve device performance. While maintaining low voltage and narrow half-width, they can improve the device's current efficiency, power efficiency, external quantum efficiency, and device lifetime, thereby enhancing the overall performance of the device and demonstrating great application potential and development prospects.

[0371] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A metal complex comprising a metal M and a ligand L coordinated to the metal M. a And has M(L) a ) m (L b ) n (L c ) q The general formula, wherein the metal M is selected from Ir, L a L b and L c These are the first ligand, the second ligand, and the third ligand that coordinate with the metal M, respectively; m is selected from 1 or 2, n is selected from 0 or 1, q is selected from 0 or 2, and m+n+q is equal to the oxidation state of the metal Ir; When m equals 2, multiple L a They are the same or different; when q equals 2, 2 L c Whether they are the same or different, the ligand L a It has a structure represented by Equation 3-4: in, A is selected from O or S each time it appears, either the same or different; R x R y Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. R x R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 cyclic atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof; L b Selected from structure L c Selected from structure Among them, R a R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; X c and X d Selected from O; R a R b R c Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, cyano groups, and combinations thereof; The substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted alkylgermanium group means that any one of the alkyl, cycloalkyl, heteroalkyl, heterocyclic, aryl, heteroaryl, alkylsilyl, and alkylgermanium groups can be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted alkylgermanium having 3-20 carbon atoms, cyano, and combinations thereof.

2. The metal complex as described in claim 1, wherein, A is selected from O.

3. The metal complex as described in claim 1, wherein, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

4. The metal complex as described in claim 3, wherein, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 15 carbon atoms, cyano groups, and combinations thereof.

5. The metal complex as described in claim 3, wherein, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, trimethylsilyl, trifluoromethyl, cyano, partially or fully deuterated methyl, partially or fully deuterated ethyl, partially or fully deuterated n-propyl, partially or fully deuterated isopropyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated neopentyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated trimethylsilyl, and combinations thereof.

6. The metal complex as described in claim 1, wherein, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

7. The metal complex of claim 6, wherein, R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 15 carbon atoms, cyano groups, and combinations thereof.

8. The metal complex of claim 6, wherein, R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclohexyl, trimethylsilyl, trifluoromethyl, cyano, partially or fully deuterated methyl, partially or fully deuterated ethyl, partially or fully deuterated n-propyl, partially or fully deuterated isopropyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated neopentyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated trimethylsilyl, and combinations thereof.

9. The metal complex as claimed in claim 1, wherein, The ligand L a The structure represented by free form 3-4 is selected each time it appears, either the same or different: Where A is selected from O or S; R x R y Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R x R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof. The substituted alkyl group, or substituted cycloalkyl group, means that any one of the groups in the alkyl or cycloalkyl group can be replaced by one or more alkyl groups selected from deuterium, halogens, unsubstituted alkyl groups having 1-20 carbon atoms, and combinations thereof.

10. The metal complex of claim 9, wherein, At least one R x and / or at least one R y Each time it appears, it is selected from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

11. The metal complex of claim 1, wherein, The ligand L a Each occurrence is either identical or different from the group consisting of the following structures: Optionally, the L a145 L a146 L a151 L a152 L a173 L a174 L a179 L a180 L a347 L a348 L a371 L a372 L a379 L a380 L a498 To L a547 L a563 To L a620 L a638 To L a654 L a667 L a668 The hydrogen in the structure can be partially or completely replaced by deuterium.

12. The metal complex of claim 1, wherein, The metal complex has Ir(L) a )2(L b The general formula of ) and has the structure represented by Equation 4: In this case, A is selected from O or S each time it appears, either identically or differently; R x R y Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R x R y R1-R7 are selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, cyano groups, and combinations thereof.

13. The metal complex of claim 12, wherein, At least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; And / or at least one of R4-R6 is a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 cyclic carbon atoms, or a combination thereof.

14. The metal complex of claim 12, wherein, R1-R3 include at least two selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, or combinations thereof; and / or R4-R6 includes at least two alkyl groups selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.

15. The metal complex of claim 1, wherein, The metal complex has Ir(L) a ) m (L c ) 3-m The general formula has the structure represented by Equation 5: Where m is selected from 1; two L c Same or different; A is selected from O or S each time it appears, either identically or differently; R x R y Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R x R y R a1 -R a4 ,R b1 -R b4 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

16. The metal complex of claim 15, wherein, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of the following are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.

17. The metal complex of claim 15, wherein, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of them are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4 to 10 cyclic carbon atoms, and combinations thereof.

18. The metal complex of claim 15, wherein, R a2 R a3 R b2 R b3 At least one, at least two, at least three, or all of them are selected from the group consisting of: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof.

19. The metal complex of claim 11, wherein, L b Each occurrence is either identical or different from the group consisting of the following structures: Among them, L c Each occurrence is either identical or different from the group consisting of the following structures:

20. The metal complex of claim 19, wherein, The metal complex is an Ir complex and has Ir(L) a )2(L b ) and Ir(L a (L) c Any of the structures shown in )2; when the metal complex has Ir(L a )2(L b When the structure of ) is used, the L a Choose L each time it appears, either the same or different. a145 L a146 L a151 L a152 L a173 L a174 L a179 L a180 L a347 L a348 L a371 L a372 L a379 L a380 L a498 To L a547 L a563 To L a620 L a638 To L a654 L a667 L a668 Any of the groups formed, the L b Choose freely L b1 To L b322 Any one of the groups; when the metal complex has Ir(L a (L) c When the structure of )2 is used, the L a Choose freely L a145 L a146 L a151 L a152 L a173 L a174 L a179 L a180 L a347 L a348 L a371 L a372 L a379 L a380 L a498 To L a547 L a563 To L a620 L a638 To L a654 L a667 L a668 Any of the groups formed, the L c Choose L each time it appears, either the same or different. c1 To L c38 L c232 To L c321 Any one of the groups formed.

21. The metal complex of claim 19, wherein, The metal complex is selected from the group consisting of compounds 17 to 26, 41 to 46, 71 to 85, 161 to 211, 286 to 311, and 436 to 510. Among them, compounds 17 to 26, compounds 41 to 46, and compounds 71 ​​to 85 have Ir(L a )2(L b The general formula for ), where the two L's a Same, L a and L b These correspond to the structures listed in the table below: Among them, compounds 161 to 211, compounds 286 to 311, and compounds 436 to 510 have Ir(L a (L) c The general formula for )2, where the two L c Same, L a and L c These correspond to the structures listed in the table below: Optionally, the hydrogen in the structures of compounds 17 to 26, 41 to 46, 71 to 85, 161 to 211, 286 to 311, and 436 to 510 may be partially or completely replaced by deuterium.

22. An electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex as described in any one of claims 1-21.

23. The electroluminescent device as claimed in claim 22, wherein, The organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

24. The electroluminescent device as claimed in claim 23, wherein, The electroluminescent device emits red, yellow, green, or white light.

25. The electroluminescent device as claimed in claim 23, wherein, The light-emitting layer further comprises a first host compound.

26. The electroluminescent device as claimed in claim 25, wherein, The light-emitting layer further comprises a second host compound.

27. The electroluminescent device as claimed in claim 26, wherein, The first host compound and / or the second host compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

28. The electroluminescent device of claim 26, wherein the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

29. The electroluminescent device of claim 28, wherein the weight of the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

30. A compound composition comprising the metal complex as described in any one of claims 1-21.

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