Organic Electroluminescent Materials and Devices

Abstract

Organic electroluminescent materials and devices are disclosed. The organic electroluminescent material is a metal complex of a La ligand having the structure of Formula 1A and a Lb ligand having the structure of Formula 1B. These novel compounds can be applied to electroluminescent devices to improve the luminescence performance, efficiency or lifespan of the devices, exhibit more saturated luminescence, and significantly enhance the comprehensive performance of the devices. An electroluminescent device containing the metal complex and a compound combination containing the metal complex are also disclosed.

Description

Technical Field

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a metal complex comprising an L ligand of Formula 1A and an L ligand of Formula 1B a ligand, and an electroluminescent device and a compound combination comprising the metal complex. b Background Art

[0002] Organic electronic devices include but are not limited to the following types: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect quantum dots (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.

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

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

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

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

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

[0008] US20190280221A1 discloses a ligand structure as follows Further disclosed is an iridium complex having the following structure wherein, R3 is selected from alkyl and cycloalkyl. In this application, a metal complex with a specific R3 substitution and its device performance are disclosed, but this application does not disclose or teach a specific R2 substitution and R at a specific position on the phenyl group of phenylpyridine E 、R F for a metal complex with specific substitutions and its influence on device performance. SUMMARY OF THE INVENTION

[0009] The present invention aims to provide a series of metal complexes containing ligands of Formula 1A structure a and ligands of Formula 1B structure b to solve at least part of the above problems. The metal complexes can be used as luminescent materials in electroluminescent devices. These novel compounds can be applied to electroluminescent devices to improve the luminescence performance, efficiency or lifespan of the devices, exhibit more saturated luminescence, and significantly enhance the comprehensive performance of the devices.

[0010] According to an embodiment of the present invention, a metal complex is disclosed, which has the general formula of M(L a ) m (L b ) n (L c ) q

[0011] [[ID=�3]]wherein,

[0012] L a 、L b and L c are the first, second and third ligands coordinated with metal M respectively, and L a ,L b ,L c are the same or different; wherein, L a 、L b and L c can optionally be connected to form a tetradentate or polydentate ligand;

[0013] Metal M is selected from metals with a relative atomic mass greater than 40;

[0014] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, and m + n + q is equal to the oxidation state of M; when m is 2, the two L a can be the same or different; when n is 2, the two L b can be the same or different;

[0015] wherein, L a each occurrence is the same or different and has the structure represented by Formula 1A; L b ​Each occurrence identically or differently has a structure represented by Formula 1B;

[0016]

[0017] in,

[0018] Each occurrence of Z is identical or different and is selected from the group consisting of O, S, Se, NR, CR'R' and SiR'R'; when two R' are present at the same time, the two R's are identical or different;

[0019] Cy is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof;

[0020] Each occurrence of X1-X8 is selected from C, CR x Or N; at least one of X1-X4 is selected from C and is connected to Cy;

[0021] At least one of X1-X8 is selected from CR x , and the R x is cyano or fluorine;

[0022] X1, X2, X3 or X4 is connected to the metal M through a metal-carbon bond or a metal-single bond;

[0023] Each time U1-U4 appears, it is selected from CR u or N;

[0024] W1-W3 are selected from CR in the same or different manner at each occurrence. w or N;

[0025] In Formula 1A, the R A It has a structure represented by Formula 2, wherein the total number of carbon atoms in Formula 2 is greater than or equal to 2:

[0026]

[0027] “*” indicates the connection position between Formula 2 and Formula 1A;

[0028] R A1 , R A2 , R A3 , R', R x , R u , R wEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0029] Adjacent substituents R A1 , R A2 , R A3 , R’, R x , R u , R w can optionally be connected to form a ring;

[0030] wherein, L c is a monoanionic bidentate ligand.

[0031] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes:

[0032] An anode,

[0033] A cathode,

[0034] and an organic layer disposed between the anode and the cathode, at least one layer of the organic layer contains the metal complex described in the above embodiment.

[0035] According to another embodiment of the present invention, a compound combination is also disclosed, which contains the metal complex described in the above embodiment.

[0036] A series of L ligands having the structure of formula IA and L ligands having the structure of formula IB disclosed by the present invention a and bMetal complexes of ligands. These metal complexes can be used as luminescent materials in electroluminescent devices, and when applied in electroluminescent devices, they can improve the luminescence performance, efficiency or lifespan of the devices, exhibit more saturated luminescence, and significantly enhance the comprehensive performance of the devices. Description of the Drawings

[0037] Figure 1 It is a schematic diagram of an organic light-emitting device that can contain the metal complexes and compound compositions disclosed herein.

[0038] Figure 2 It is another schematic diagram of an organic light-emitting device that can contain the metal complexes and compound compositions disclosed herein. Detailed Description of the Invention

[0039] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 Schematically and non-limitingly shows an organic light-emitting device 100. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.

[0040] Each of these layers has more examples. For example, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety. U.S. Patents Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety.

[0041] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve a desired emission spectrum.

[0042] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0043] The OLED also requires a packaging layer, as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0044] Devices fabricated in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) that include such devices. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0045] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0046] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, there may be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

[0047] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0048] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0049] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0050] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of back-filled singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.

[0051] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0052] Definition of substituent terms

[0053] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0054] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.

[0055] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl, 1 - adamantyl, 2 - adamantyl, 1 - norbornyl, 2 - norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, and 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0056] Heteroalkyl - as used herein, heteroalkyl is formed by substituting one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0057] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - methylvinyl, styryl, 2,2 - diphenylethylene, 1,2 - diphenylethylene, 1 - methylallyl, 1,1 - dimethylallyl, 2 - methylallyl, 1 - phenylallyl, 2 - phenylallyl, 3 - phenylallyl, 3,3 - diphenylallyl, 1,2 - dimethylallyl, 1 - phenyl - 1 - butenyl, 3 - phenyl - 1 - butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0058] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropargyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0059] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0060] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.

[0061] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups having 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and their nitrogen - containing analogs. Additionally, the heteroaryl can be optionally substituted.

[0062] Alkoxy - As used herein, it is represented by - O - alkyl, - O - cycloalkyl, - O - heteroalkyl or - O - heterocyclic group. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclic group are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0063] Aryloxy - As used herein, it is represented by - O - aryl or - O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0064] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,

[0065] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0066] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0067] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tributylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methyldi-tert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0068] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0069] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or at least two C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0070] In the present disclosure, unless otherwise defined, when any one of the following terms is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxy, substituted ester, substituted sulfinyl, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxy, ester, sulfinyl, sulfonyl and phosphino can be substituted by one or at least two selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocycloalkyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxy, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0071] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attached fragment are considered equivalent.

[0072] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0073] Among the compounds mentioned in the present disclosure, multiple substitution refers to the range including double substitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist at multiple available substitution positions on its connecting structure, and the substituents existing at multiple available substitution positions can be of the same structure or different structures.

[0074] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, otherwise adjacent substituents in the compound cannot connect to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case 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 spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0075] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0076]

[0077] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0078]

[0079] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0080]

[0081] In addition, the expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded, thus forming a ring. This is exemplified by the following formula:

[0082]

[0083] According to one embodiment of the present invention, a metal complex is disclosed, which has the general formula M(L a ) m (L b ) n (L c ) q .

[0084] Wherein,

[0085] L a , L b and L c are the first, second and third ligands coordinated to the metal M respectively, and L a , L b , L c are the same or different; wherein, L a , L b and L c can optionally be connected to form a tetradentate or polydentate ligand;

[0086] The metal M is selected from metals with a relative atomic mass greater than 40;

[0087] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, and m + n + q is equal to the oxidation state of M; when m is 2, the two L a can be the same or different; when n is 2, the two L b can be the same or different;

[0088] Wherein, L a each occurrence is the same or different and has the structure represented by Formula 1A; L b each occurrence is the same or different and has the structure represented by Formula 1B;

[0089]

[0090] Wherein,

[0091] Z is the same or different each occurrence and is selected from the group consisting of O, S, Se, NR’, CR’R’ and SiR’R’; when two R’ are present simultaneously, the two R’ are the same or different;

[0092] Cy is the same or different each occurrence and is selected from a substituted or unsubstituted aromatic ring having 6 - 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 - 24 ring atoms, or a combination thereof;

[0093] X1 - X8 are the same or different each occurrence and are selected from C, CR x or N; at least one of X1 - X4 is selected from C and is connected to Cy;

[0094] At least one of X1 - X8 is selected from CR x and said R x is cyano or fluorine;

[0095] X1, X2, X3 or X4 is connected to metal M through a metal - carbon bond or a metal - single bond;

[0096] Each occurrence of U1 - U4 is the same or different and is selected from CR u or N;

[0097] Each occurrence of W1 - W3 is the same or different and is selected from CR w or N;

[0098] In Formula 1A, said R A has a structure represented by Formula 2 and the total number of carbon atoms in Formula 2 is greater than or equal to 2:

[0099]

[0100] "*" represents the connection position of Formula 2 and Formula 1A;

[0101] R A1 R A2 R A3 R', R x R u R w Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino group having 0 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0102] Adjacent substituents R A1 RA2 , R A3 , R’, R x , R u , R w may optionally be linked to form a ring;

[0103] wherein, L c is a monoanionic bidentate ligand.

[0104] In this text, the statement “adjacent substituents R A1 , R A2 , R A3 , R’, R x , R u , R w may optionally be linked to form a ring” is intended to mean that among adjacent substituent groups, for example, between substituent R A1 and R A2 , between substituent R A1 and R A3 , between substituent R A2 and R A3 , between substituent R A1 and R u , between substituent R u and R A3 , between substituent R A2 and R u , between two substituents R, between substituent R and R x , between two substituents R x , between two substituents R u , between two substituents R w , between two substituents R y , any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may also not be linked to form a ring at all.

[0105] According to one embodiment of the present invention, wherein, L c is the same or different each time it appears and is selected from any one of the structures shown in the group consisting of:

[0106]

[0107] wherein,

[0108] R a , R b and R c are the same or different each time they appear and represent mono-substitution, multi-substitution, or no substitution;

[0109] X b is the same or different each time it appears and is selected from the group consisting of: O, S, Se, NR N1, CR C1 R C2 ;

[0110] R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0111] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0112] In this context, “the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent Rb and R c between, the substituent R a and R N1 between, the substituent R b and R N1 between, the substituent R a and R C1 between, the substituent R a and R C2 between, the substituent R b and R C1 between, the substituent R b and R C2 between, and R C1 and R C2 between, any one or more of these substituent groups may be connected to form a ring. Obviously, these substituents may also not be connected to form a ring with each other.

[0113] According to an embodiment of the present invention, wherein Cy is selected from any one of the structures consisting of the following:

[0114]

[0115]

[0116] wherein,

[0117] R represents a single substitution, multiple substitutions, or no substitution, the same or different each time it appears; when there are multiple Rs in any one structure, the Rs are the same or different;

[0118] Each occurrence of R is the same as or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino group having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0119] Adjacent substituents R can optionally be joined to form a ring;

[0120] wherein, "#" represents the position connected to metal M, represents the position connected to X1, X2, X3 or X4.

[0121] In this article, "adjacent substituents R can optionally be joined to form a ring" is intended to mean that any one or more of any two adjacent substituents R x in the group can be joined to form a ring. Obviously, these substituents may also not be joined to form a ring with each other.

[0122] According to one embodiment of the present invention, wherein L b has a structure represented by Formulae 1Ba-1Bf:

[0123]

[0124] wherein,

[0125] Each occurrence of Z is the same as or different from each other and is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R'; when two R's are present simultaneously, the two R's are the same as or different from each other;

[0126] In Formulae 1Ba and 1Bf, each occurrence of X3-X8 is the same as or different from each other and is selected from CR x or N;

[0127] In Formula 1Bb and Formula 1Bd, X1 and X4 - X8 are each independently selected from CR x or N;

[0128] In Formula 1Bc and Formula 1Be, X1 - X2 and X5 - X8 are each independently selected from CR x or N;

[0129] At least one of X1 - X8 is selected from CR x and said R x is cyano or fluoro;

[0130] Y1 - Y4 are each independently selected from CR y or N;

[0131] R', R x R y each occur independently and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0132] Adjacent substituents R', R x R y can optionally be linked to form a ring.

[0133] In this embodiment, "adjacent substituents R', R x R y can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between two substituents R', between two substituents R x between two substituents R y between two substituents R' and R xAmong them, any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring either.

[0134] According to one embodiment of the present invention, wherein, the metal complex Ir(L a ) m (L b ) 3-m has a structure represented by Formula 3:

[0135]

[0136] Wherein,

[0137] Z is the same or different each time it appears and is selected from the group consisting of O, S, Se, NR', CR'R', and SiR'R'; when two R's are present simultaneously, the two R's are the same or different;

[0138] X3 - X8 are the same or different each time they appear and are selected from CR x or N;

[0139] At least one of X3 - X8 is selected from CR x , and the R x is cyano or fluorine;

[0140] Y1 - Y4 are the same or different each time they appear and are selected from CR y or N;

[0141] U1 - U4 are the same or different each time they appear and are selected from CR u or N;

[0142] W1 - W3 are the same or different each time they appear and are selected from CR w or N;

[0143] R A1 ,R A2 ,R A3 ,R’, R x ,R y ,R u ,R wEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino group having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; and R A1 and R A2 and R A3 have a total number of carbon atoms greater than or equal to 1;

[0144] Adjacent substituents R A1 and R A2 and R A3 can optionally be linked to form a ring;

[0145] Adjacent substituents R', R x and R y and R u and R w can optionally be linked to form a ring.

[0146] As used herein, "adjacent substituents R A1 and R A2 and R A3 can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between substituent R A1 and R A2 , between substituent R A1 and R A3 , between substituent R A2 and R A3 , any one or more of these substituent groups can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring at all.

[0147] As used herein, "adjacent substituents R', R x and R y, R u , R w "can optionally be linked to form a ring", which is intended to represent adjacent substituent groups. For example, between two substituents R', between a substituent R' and R x , between two substituents R x , between two substituents R u , between two substituents R w , between two substituents R y , any one or more of these substituent groups can be linked to form a ring. Obviously, none of these substituents can also be linked to form a ring.

[0148] According to an embodiment of the present invention, wherein, wherein, the metal complex Ir(L a ) m (L b ) 3-m has a structure represented by Formula 4 or Formula 5:

[0149]

[0150] Wherein,

[0151] R x , R y each occurrence represents, the same or differently, a mono-substituted, multi-substituted or unsubstituted;

[0152] R A1 , R A2 , R A3 , R x , R y, each occurrence of R1 - R7 is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino group having 0 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; and R A1 , R A2 and R A3 have a total number of carbon atoms greater than or equal to 1;

[0153] R x has at least one being a cyano group or a fluorine atom;

[0154] Adjacent substituents R A1 , R A2 , R A3 can optionally be linked to form a ring;

[0155] Adjacent substituents R x , R y , R1 - R7 can optionally be linked to form a ring.

[0156] As used herein, the phrase "adjacent substituents R x , R y , R1 - R7 can optionally be linked to form a ring" is intended to mean any adjacent group of substituents, for example, between two substituents R', between a substituent R' and R x , between substituents R1 and R2, between substituents R3 and R4, between substituents R4 and R5, between substituents R5 and R6, between substituents R6 and R7, between two substituents R x , between two substituents R y , any one or more of these groups of substituents can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring with each other.

[0157] According to one embodiment of the present invention, Z is selected from the group consisting of O and S.

[0158] According to one embodiment of the present invention, Z is selected from O.

[0159] According to one embodiment of the present invention, X1 - X8 are each independently selected from C or CR each time they appear. x 。

[0160] According to one embodiment of the present invention, X3 - X8 are each independently selected from C or CR each time they appear. x 。

[0161] According to one embodiment of the present invention, at least one of X1 - X8 is selected from N. For example, one of X1 - X8 is selected from N, or two of X1 - X8 are selected from N.

[0162] According to one embodiment of the present invention, at least one of X3 - X8 is selected from N. For example, one of X3 - X8 is selected from N, or two of X3 - X8 are selected from N.

[0163] According to one embodiment of the present invention, W1 - W3 are each independently selected from C or CR each time they appear. w 。

[0164] According to one embodiment of the present invention, U1 - U4 are each independently selected from C or CR each time they appear. u 。

[0165] According to one embodiment of the present invention, Y1 - Y4 are each independently selected from C or CR each time they appear. y 。

[0166] According to one embodiment of the present invention, at least one of W1 - W3 is selected from N. For example, one of W1 - W3 is selected from N, or two of W1 - W3 are selected from N.

[0167] According to one embodiment of the present invention, at least one of U1 - U4 is selected from N. For example, one of U1 - U4 is selected from N, or two of U1 - U4 are selected from N.

[0168] According to one embodiment of the present invention, at least one of Y1 - Y4 is selected from N. For example, one of Y1 - Y4 is selected from N, or two of Y1 - Y4 are selected from N.

[0169] According to one embodiment of the present invention, R w and R uEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0170] According to one embodiment of the present invention, wherein R w and R u Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, and combinations thereof.

[0171] According to one embodiment of the present invention, wherein R w and R u Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

[0172] According to one embodiment of the present invention, wherein R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0173] According to one embodiment of the present invention, wherein R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, and combinations thereof.

[0174] According to one embodiment of the present invention, wherein R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

[0175] According to one embodiment of the present invention, wherein each occurrence of U1-U4 is the same as or different from and is selected from CR u and the total number of carbon atoms of the R u is at least 4.

[0176] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, and combinations thereof.

[0177] According to one embodiment of the present invention, the total number of carbon atoms of all the R u is at least 4.

[0178] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 ring carbon atoms, and combinations thereof.

[0179] According to one embodiment of the present invention, U2 and / or U3 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 ring carbon atoms, and combinations thereof; and the total number of carbon atoms of all the R u is at least 4.

[0180] According to one embodiment of the present invention, U2 or U3 is selected from CR u , and the R u is selected from substituted or unsubstituted alkyl having 3-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 ring carbon atoms, or combinations thereof.

[0181] According to one embodiment of the present invention, U2 or U3 is selected from CR u , and the R u is selected from substituted or unsubstituted alkyl having 4-12 carbon atoms, substituted or unsubstituted cycloalkyl having 4-12 ring carbon atoms, or combinations thereof.

[0182] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 3-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 ring carbon atoms, and combinations thereof.

[0183] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR u , and the Ru Has the structure represented by Formula 2.

[0184] According to one embodiment of the present invention, wherein, U2 or U3 is selected from CR u , and said R u Has the structure represented by Formula 2.

[0185] According to one embodiment of the present invention, wherein, R A1 , R A2 , R A3 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino group having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; and the total number of carbon atoms of R A1 , R A2 and R A3 is greater than or equal to 3.

[0186] According to one embodiment of the present invention, wherein the total number of carbon atoms in Formula 2 is greater than or equal to 4.

[0187] According to one embodiment of the present invention, wherein, R A1 , R A2 , R A3each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-6 carbon atoms, substituted or unsubstituted heterocyclyl having 3-6 ring atoms, substituted or unsubstituted aralkyl having 7-13 carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, cyano, and combinations thereof; and R A1 , R A2 and R A3 The total number of carbon atoms is greater than or equal to 3.

[0188] According to one embodiment of the present invention, R A1 , R A2 , R A3 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, and combinations thereof.

[0189] According to one embodiment of the present invention, R A1 , R A2 , R A3 Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, and R A1 , R A2 and R A3 The total number of carbon atoms is greater than or equal to 3 and less than or equal to 9.

[0190] According to one embodiment of the present invention, R A1 , R A2 , R A3 wherein two of the moieties are identically or differently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, and the other is selected from the group consisting of deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted cyano groups having 0 to 20 carbon atoms, and combinations thereof.

[0191] According to one embodiment of the present invention, RA1 ,R A2 ,R A3 comprises two that are the same or different and are selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; and the other is selected from the group consisting of: deuterium, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 12 carbon atoms, a cyano group, and combinations thereof.

[0192] According to one embodiment of the present invention, each occurrence of formula 2 is the same or different and is selected from the group consisting of A-1 to A-83, and the specific structures of A-1 to A-83 are as described in claim 14.

[0193] According to one embodiment of the present invention, the hydrogen in A-1 to A-83 can be partially or completely substituted by deuterium.

[0194] According to one embodiment of the present invention, at least one of X1-X8 is selected from CR x , and the R x is a cyano group or fluorine.

[0195] According to one embodiment of the present invention, at least one of X3-X8 is selected from CR x , and the R x is a cyano group or fluorine.

[0196] According to one embodiment of the present invention, at least one of X5-X8 is selected from CR x , and the R x is a cyano group or fluorine.

[0197] According to one embodiment of the present invention, at least one of X7 or X8 is selected from CR x , and the R x is a cyano group or fluorine.

[0198] According to one embodiment of the present invention, X8 is selected from CR x .

[0199] According to one embodiment of the present invention, when X8 is selected from N, at least one of X1-X7 is selected from CR x , and the R x is a cyano group; when the remaining of X1-X7 are selected from CR x , the R xSelected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof.

[0200] According to one embodiment of the present invention, at least two of X3 - X8 are CR x , and one of said R x is a cyano group or a fluorine atom, and at least one other of said R x is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0201] According to one embodiment of the present invention, at least two of X5 - X8 are CR x , and one of said R x is a cyano group or a fluorine atom, and at least one other of said R x is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a mercapto group, and combinations thereof.

[0202] According to one embodiment of the present invention, wherein X7 - X8 is selected from CR x , and one of the R x is cyano or fluorine, and the other R x is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 6 ring carbon atoms, substituted or unsubstituted aryl having 6 - 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 12 carbon atoms, and combinations thereof.

[0203] According to one embodiment of the present invention, wherein R x is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, cyano, hydroxyl, mercapto, and combinations thereof.

[0204] According to one embodiment of the present invention, wherein R x is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof.

[0205] According to one embodiment of the present invention, wherein R', each time it appears, is the same or different and is selected from substituted or unsubstituted alkyl having 1 - 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 6 ring carbon atoms, substituted or unsubstituted aryl having 6 - 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 12 carbon atoms or combinations thereof.

[0206] According to one embodiment of the present invention, wherein R' is selected from methyl, phenyl or deuterated methyl.

[0207] According to one embodiment of the present invention, wherein L a , each time it appears, is the same or different and is selected from the group consisting of L a1-1 -L a1-121 , L a2-1 -L a2-116 , L aD-1 -L aD-128 consisting of the group, wherein L a1-1 -La1-121 , L a2-1 , -L a2-116 , L aD-1 , -L aD-128 The specific structure of, L, -L, L, -L, L, -L is shown in claim 17.

[0208] According to an embodiment of the present invention, wherein, L a1-1 , -L a1-121 , L a2-1 , -L a2-116 , L aD-1 , -L aD-128 the hydrogen in, L, -L, L, -L, L, -L is partially or completely replaced by deuterium.

[0209] According to an embodiment of the present invention, wherein, L b is the same or different each time it appears and is selected from the group consisting of L b1-1 , -L b1-355 , L b2-1 , -L b2-283 , L bx-1 , -L bx-76 wherein L b1-1 , -L b1-355 , L b2-1 , -L b2-283 , L bx-1 , -L bx-76 The specific structure of, L, -L, L, -L, L, -L is shown in claim 18.

[0210] According to an embodiment of the present invention, wherein, L b1-1 , -L b1-355 , L b2-1 , -L b2-283 , L bx-1 , -L bx-76 the hydrogen in, L, -L, L, -L, L, -L is partially or completely replaced by deuterium.

[0211] According to an embodiment of the present invention, wherein, L c is the same or different each time it appears and is selected from the group consisting of L c1 , -L c360 wherein L c1 , -L c360 The specific structure of, L, -L is shown in claim 19.

[0212] According to an embodiment of the present invention, wherein the metal complex has the structure of Ir(L a )2L b , and the two Ls are the same or different; L a is the same or different each time it appears and is selected from the group consisting of L a , -L a1-1 , L a1-121 , -L a2-1 , L a2-116 , L aD-1-L aD-128 A group consisting of; L b Selected from the group consisting of L b1-1 -L b1-355 , L b2-1 -L b2-283 , L bx-1 -L bx-76 A group consisting of

[0213] According to an embodiment of the present invention, wherein the metal complex has the structure of IrL a (L b )2, and the two Ls b are the same or different; L a Selected from the group consisting of L a1-1 -L a1-121 , L a2-1 -L a2-116 , L aD-1 -L aD-128 A group consisting of; L b Each occurrence is the same or different and is selected from the group consisting of L b1-1 -L b1-355 , L b2-1 -L b2-283 , L bx-1 -L bx-76 A group consisting of

[0214] According to an embodiment of the present invention, wherein the metal complex has the structure of Ir(L a )(L b )(L c ); L a Selected from L a1-1 -L a1-121 , L a2-1 -L a2-116 , L aD-1 -L aD-128 A group consisting of; L b Selected from L b1-1 -L b1-355 , L b2-1 -L b2-283 , L bx-1 -L bx-76 A group consisting of; L c Selected from L c1 -L c360 A group consisting of, wherein the specific structure of L c1 -L c360 is shown in Claim 19

[0215] According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 1488, and the specific structures of Metal Complex 1 to Metal Complex 1488 are shown in Claim 20

[0216] According to one embodiment of the present invention, wherein L a is the same or different each time it appears and is selected from the group consisting of L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 , where the specific structure of L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 is shown in claim 17.

[0217] According to one embodiment of the present invention, wherein L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 the hydrogen in it is partially or completely replaced by deuterium.

[0218] According to one embodiment of the present invention, wherein L b is the same or different each time it appears and is selected from the group consisting of L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 , where the specific structure of L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 is shown in claim 18.

[0219] According to one embodiment of the present invention, wherein L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 the hydrogen in it is partially or completely replaced by deuterium.

[0220] According to one embodiment of the present invention, wherein L c is the same or different each time it appears and is selected from the group consisting of L c1 -L c360 , where the specific structure of L c1 -L c360 is shown in claim 19.

[0221] According to an embodiment of the present invention, the metal complex has the structure of Ir(L a )2L b , where the two L a are the same or different; L a , each occurrence being the same or different, is selected from the group consisting of L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 ; L b is selected from the group consisting of L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 .

[0222] According to an embodiment of the present invention, the metal complex has the structure of IrL a (L b )2, where the two L b are the same or different; L a is selected from the group consisting of L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 ; L b , each occurrence being the same or different, is selected from the group consisting of L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 .

[0223] According to an embodiment of the present invention, the metal complex has the structure of Ir(L a )(L b )(L c ); L a is selected from the group consisting of L a1-1 -L a1-123 , L a2-1 -L a2-116 , L aD-1 -L aD-128 ; L b is selected from the group consisting of L b1-1 -L b1-357 , L b2-1 -L b2-285 , L bx-1 -L bx-76 ; L c is selected from Lc1 -L c360 A group consisting of, where L c1 -L c360 The specific structure of is shown in claim 19.

[0224] According to one embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complexes 1 to 1504, and the specific structures of metal complexes 1 to 1504 are shown in claim 20.

[0225] According to one embodiment of the present invention, an electroluminescent device is also disclosed, which includes:

[0226] An anode,

[0227] A cathode,

[0228] And an organic layer disposed between the anode and the cathode, at least one layer of the organic layer contains the metal complex described in any of the foregoing embodiments.

[0229] According to one embodiment of the present invention, wherein the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

[0230] According to one embodiment of the present invention, wherein the light-emitting layer in the electroluminescent device emits green light.

[0231] According to one embodiment of the present invention, wherein a first host compound is further included in the light-emitting layer of the electroluminescent device.

[0232] According to one embodiment of the present invention, wherein a first host compound and at least one second host compound are further included in the light-emitting layer of the electroluminescent device.

[0233] According to one embodiment of the present invention, wherein at least one of the host compounds in the electroluminescent device contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicofluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0234] According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula X:

[0235]

[0236] Wherein,

[0237] L xEach occurrence is the same or different and is independently selected from a single bond, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, or a combination thereof;

[0238] Each occurrence of V is the same or different and is independently selected from C, CR v or N, and at least one of V is C and is linked to L x ;

[0239] Each occurrence of T is the same or different and is independently selected from C, CR t or N, and at least one of T is C and is linked to L x ;

[0240] R v and R t Each occurrence is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0241] Each occurrence of Ar1 is the same or different and is independently selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;

[0242] Adjacent substituents R v and R t can optionally be linked to form a ring.

[0243] In this embodiment, "adjacent substituents R v and R t can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between two substituents R v , between two substituents R tBetween two substituents R v and R t Among them, any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring either.

[0244] According to an embodiment of the present invention, wherein the first host compound has a structure represented by one of Formula X-a to Formula X-j:

[0245]

[0246]

[0247] Wherein,

[0248] L x Each occurrence is independently selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0249] V is the same or different each occurrence and is independently selected from CR v or N;

[0250] T is the same or different each occurrence and is independently selected from CR t or N;

[0251] R v and R t Each occurrence is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl having 6-20 carbon atoms, a substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0252] Ar1 is the same as or different from each other each time it appears and is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

[0253] Adjacent substituents R v and R t can optionally be linked to form a ring.

[0254] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0255] According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3% - 13% of the total weight of the light-emitting layer.

[0256] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0257] In combination with other materials

[0258] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0259] The materials described herein as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the devices. By way of example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0260] 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 received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art (including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeters from Shimadzu, fluorescence spectrophotometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc.) by methods well-known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art (including but not limited to evaporation coaters produced by Angstrom Engineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc.) by methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and test methods and can obtain the inherent data of the samples determinately and without interference, the above relevant content will not be elaborated further in this patent.

[0261] Examples of material synthesis:

[0262] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0263] Synthesis Example 1: Synthesis of metal complex 241

[0264] Step 1:

[0265]

[0266] 2-(3-tert-Butylphenyl)pyridine (3.6 g, 17.1 mmol), iridium(III) chloride trihydrate (1.6 g, 4.5 mmol), 120 mL of 2-ethoxyethanol, and 40 mL of water were successively added to a dried 500 mL round-bottom flask. The flask was purged with nitrogen three times and then protected with nitrogen. The mixture was heated and stirred at 130 °C for 24 h. After cooling, it was filtered, rinsed three times with methanol and n-hexane respectively, and dried to obtain 2.8 g of intermediate 1 (96% yield).

[0267] Step 2:

[0268]

[0269] In a dried 250 mL round-bottom flask, intermediate 1 (2.8 g, 2.2 mmol), 100 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (1.2 g, 4.8 mmol) were successively added. The flask was purged with nitrogen three times and protected with nitrogen, and stirred overnight at room temperature. It was filtered through diatomaceous earth and rinsed twice with dichloromethane. The organic phase below was collected and concentrated under reduced pressure to obtain 3.6 g of yellow solid intermediate 2 (99% yield).

[0270] Step 3:

[0271]

[0272] In a dried 250 mL round-bottom flask, intermediate 2 (3.6 g, 4.4 mmol), intermediate 3 (1.8 g, 6.6 mmol), 2-ethoxyethanol (50 mL), and DMF (50 mL) were successively added. Under N2 protection, the reaction was heated at 100 °C for 96 h. After the reaction cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain 2.8 g of yellow solid metal complex 241 (72% yield). The structure of this product was determined to be the target product with a molecular weight of 883.3.

[0273] Synthesis Example 2: Synthesis of Metal Complex 13

[0274] Step 1:

[0275]

[0276] In a dried 500 mL round-bottom flask, 5-tert-butyl-2-(3-tert-butylphenyl)pyridine (4.7 g, 17.6 mmol), iridium(III) chloride trihydrate (1.5 g, 4.2 mmol), 120 mL of 2-ethoxyethanol, and 40 mL of water were successively added. The flask was purged with nitrogen three times and protected with nitrogen, and heated and stirred at 130 °C for 24 h. After cooling, it was filtered, rinsed three times with methanol and n-hexane respectively, and dried to obtain 3.0 g of intermediate 4 (96% yield).

[0277] Step 2:

[0278]

[0279] In a dried 250 mL round-bottom flask, intermediate 4 (3.0 g, 2.0 mmol), 100 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (1.1 g, 4.3 mmol) were successively added. The flask was purged with nitrogen three times and protected with nitrogen, and stirred overnight at room temperature. It was filtered through diatomaceous earth and rinsed twice with dichloromethane. The organic phase below was collected and concentrated under reduced pressure to obtain 3.7 g of yellow solid intermediate 5 (100% yield).

[0280] Step 3:

[0281]

[0282] In a dried 250 mL round-bottom flask, intermediate 5 (3.7 g, 4.0 mmol), intermediate 6 (2.1 g, 6.0 mmol), 2-ethoxyethanol (50 mL) and DMF (50 mL) were successively added. Under N2 protection, the mixture was heated at 100 °C for reaction for 96 h. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain yellow solid metal complex 13 (2.1 g, 45% yield). The structure of this product was determined to be the target product with a molecular weight of 1075.5.

[0283] Synthesis Example 3: Synthesis of Metal Complex 1490

[0284] Step 1:

[0285]

[0286] In a dried 250 mL round-bottom flask, intermediate 5 (2.7 g, 2.8 mmol), intermediate 7 (1.5 g, 4.3 mmol), 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide were successively added. After purging with nitrogen three times and under nitrogen protection, the mixture was heated at 100 °C for reaction for 96 h. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain yellow solid product metal complex 133 (1.7 g, 56.4% yield). The product was determined to be the target product with a molecular weight of 1076.5.

[0287] Synthesis Example 4: Synthesis of Metal Complex 1496

[0288] Step 1:

[0289]

[0290] In a dried 250 mL round-bottom flask, 2-(3-(tert-butyl)-5-fluoro-phenyl)-4,5-bis(methyl-d3)pyridine (3.4 g, 12.9 mmol), iridium(III) chloride trihydrate (1.8 g, 5.1 mmol), 45 mL of 2-ethoxyethanol and 15 mL of water were successively added. After purging with nitrogen three times and under nitrogen protection, the mixture was heated and stirred at 130 °C for 24 h. After cooling, it was filtered, rinsed three times with methanol and n-hexane respectively, and dried to obtain 3.1 g of intermediate 8 (81% yield).

[0291] Step 2:

[0292]

[0293] To a dry 250 mL round-bottom flask were added intermediate 8 (3.1 g, 2.1 mmol), 100 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (1.2 g, 4.7 mmol). The atmosphere was replaced with nitrogen three times under a nitrogen blanket and stirred overnight at room temperature. Filtered through celite, rinsed twice with dichloromethane, and the organic phase below was collected and concentrated under reduced pressure to yield 3.7 g of intermediate 9 as a yellow solid (95% yield).

[0294] Step 3:

[0295]

[0296] To a dry 250 mL round-bottom flask were added intermediate 9 (2.0 g, 2.1 mmol), intermediate 3 (0.9 g, 3.3 mmol), 2-ethoxyethanol (40 mL), and DMAc (40 mL). The mixture was heated at 100°C under N2 protection for 96 h. After cooling, the reaction mixture was filtered and washed twice with methanol, n-hexane, and dichloromethane, respectively, to obtain a yellow solid metal complex 1496 (0.5 g, 24% yield). The product was confirmed to be the target product with a molecular weight of 987.4.

[0297] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0298] Device Examples

[0299] Device Example 1

[0300] First, a glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were deposited under a vacuum of approximately 10 -8In the case of the support, evaporation is sequentially carried out on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / second. Compound HI is used as the hole injection layer (HIL). Compound HT is used as the hole transport layer (HTL). Compound H1 is used as the electron blocking layer (EBL). Then, the metal complex 241 of the present invention is used as a dopant and co-deposited with Compound H1 and Compound H2 as the emitting layer (EML). On the EML, Compound HB is used as the hole blocking layer (HBL). On the HBL, Compound ET and lithium 8-hydroxyquinoline (Liq) are co-deposited as the electron transport layer (ETL). Finally, 1 nm thickness of lithium 8-hydroxyquinoline (Liq) is evaporated as the electron injection layer, and 120 nm of aluminum is evaporated as the cathode. Then the device is transferred back to the glove box and encapsulated with a glass cover to complete the device.

[0301] Device Example 2

[0302] The implementation of Device Example 2 is the same as that of Device Example 1, except that metal complex 1490 is used instead of the metal complex 241 of the present invention in the emitting layer (EML).

[0303] Device Comparative Example 1

[0304] The implementation of Device Comparative Example 1 is the same as that of Device Example 1, except that Compound GD1 is used instead of the metal complex 241 of the present invention in the emitting layer (EML).

[0305] The detailed device layer structure and thickness are shown in the following table. For the layer where more than one material is used, it is obtained by doping different compounds in the recorded weight ratio.

[0306] Table 1 Partial device structures of Device Example 1, Example 2 and Comparative Example 1

[0307]

[0308]

[0309] The material structures used in the device are as follows:

[0310]

[0311] The IVL characteristics of the device were measured. At 1000 cd / m 2 The CIE data of the device was measured, the maximum emission wavelength λ max , the full width at half maximum (FWHM), the current efficiency (CE); the external quantum efficiency (EQE) data was tested at a constant current of 15 mA / cm 2 ; the lifetime (LT97) data was tested at 80 mA / cm 2The tests were carried out under a constant current. These data were recorded and shown in Table 2.

[0312] Table 2 Device data of Device Example 1, Device Example 2 and Comparative Example 1

[0313]

[0314]

[0315] From the data shown in Table 2, the CE and EQE of Device Example 1 compared with those of Device Comparative Example 1 increased by 4.6% and 2.3% respectively; the lifetime of Device Example 1 reached 25 h, which was nearly 12.9 times higher than the lifetime of 1.8 h of Device Comparative Example 1-1, which was unexpected. In addition, compared with Device Comparative Example 1, Device Example 1 had a blue shift of 2 nm in λ max and a narrowing of 6.5 nm in FWHM, showing more saturated green emission. The significantly improved comprehensive device performance of Device Example 1 compared with that of Device Comparative Example 1, such as higher efficiency, excellent lifetime, and more saturated green emission, indicates that the metal complex of the present invention has an R a substituent at a specific substitution position in the ligand L A compared with the metal complex having a non-formula 2 substituent at a specific substitution position in the L a ligand, has an excellent effect of improving device performance.

[0316] On the basis of Example 1, Example 2 further has substitutions in the L a and L b ligands of the metal complex. On the basis of the excellent device performance of Example 1, Device Example 2 can further adjust the maximum emission wavelength to obtain a device emitting yellow light, and the device lifetime is increased by about 2.22 times. Currently, the daily white OLED lamps mainly generate white light through the combined action of yellow and blue light-emitting units. The metal complex of the present invention can show excellent device performance through further substituent modification, and has broad prospects in the commercial application of yellow or white light.

[0317] Device Comparative Example 2

[0318] The implementation mode of Device Comparative Example 2 is the same as that of Device Example 1, except that compound GD2 is used instead of the metal complex 241 of the present invention in the emitting layer (EML).

[0319] The detailed device layer structure and thickness are shown in the following table. For the layer with more than one material used, it is doped with different compounds in the weight ratio recorded.

[0320] Table 3 Device structure of Device Comparative Example 2

[0321]

[0322] The new material structure used in the device is shown below:

[0323]

[0324] The IVL characteristics of the device were measured. 2 The CIE data of the device was measured below, and the maximum emission wavelength λ max , full width at half maximum (FWHM); external quantum efficiency (EQE) data is at 15mA / cm 2 The test was carried out under constant current. These data are recorded and shown in Table 4.

[0325] Table 4 Device data of device comparison example 2

[0326]

[0327] From the data shown in Table 4, the half-peak width of device Example 1 is narrower by 5.1 nm and the EQE is improved by 10.9% compared with device Comparative Example 2. Device Example 1 has higher efficiency and more saturated green luminescence, and has significantly improved device overall performance, indicating that the L in the metal complex of the present invention is a R A Substituents at specific positions, compared to L a The metal complex in which the ligand has a 2-substituent at a non-specific substitution position has an excellent effect of improving device performance.

[0328] Device Example 3

[0329] The implementation method of device example 3 is the same as that of device example 1, except that the metal complex 13 of the present invention is used instead of the metal complex 241 of the present invention in the light-emitting layer (EML), and the ratio of compound H1, compound H2 and metal complex 13 in the light-emitting layer is 63:31:6.

[0330] Device Comparative Example 3

[0331] The device of Comparative Example 3 was carried out in the same manner as that of Device Example 3, except that the metal complex 13 of the present invention was replaced with compound GD3 in the emission layer (EML).

[0332] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, the different compounds are doped in the stated weight ratios.

[0333] Table 5 Device structures of device embodiment 3 and device comparative example 3

[0334]

[0335] The material structure newly used in the device is as follows:

[0336]

[0337] The IVL characteristics of the device were measured. The CIE data of the device were measured under 1000 cd / m 2 , the maximum emission wavelength λ max , full width at half maximum (FWHM), current efficiency (CE); the external quantum efficiency (EQE) data were tested at a constant current of 15 mA / cm 2 ; the lifetime (LT97) data were tested at a constant current of 80 mA / cm 2 . These data were recorded and shown in Table 6.

[0338] Table 6 Device data of Device Example 3 and Comparative Example 3

[0339]

[0340] From the data shown in Table 6, for Device Example 3 compared with Device Comparative Example 3, its CE increased slightly. Although the full width at half maximum widened by 6.5 nm, the 43.3 nm full width at half maximum was already at a relatively high level. Most importantly, compared with the already excellent EQE and lifetime of Comparative Example 3, the EQE and lifetime of Example 2 increased by 2.6% and 49.2% respectively, which is very valuable. Device Example 3 has higher efficiency and excellent device lifetime compared with Device Comparative Example 3, indicating that the complex of the present invention has R a substituents at specific substitution positions in ligand L A , and compared with the metal complex of ligand L a without the substituent of Formula 2 at the specific substitution position, it can significantly improve the comprehensive performance of the device.

[0341] Combining the above results shows that the metal complex disclosed in the present invention contains ligand L of Formula 1A structure a (with the substituent of Formula 2 at the specific substitution position) and ligand L of Formula 1B structure b (with specific substituents at the specific substitution positions). While maintaining the device efficiency at a high level in the industry, compared with the metal complex of ligand L a with non-Formula 2 substituents at the specific substitution position and Formula 2 substituents at non-specific substitution positions, it can further improve the device luminescence performance, efficiency or lifetime, show more saturated luminescence, and significantly improve the comprehensive performance of the device. The metal complex disclosed in the present invention has great advantages and broad prospects in industrial applications.

[0342] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A metal complex having the general formula Ir(L a ) m (L b ) 3-m , wherein, m is selected from 1 or 2. When m is 2, the two Ls a are the same or different; when m is 1, the two Ls b are the same or different; L a each occurrence is the same or different and has a structure represented by Formula 1A; L b each occurrence is the same or different and has a structure represented by Formula 1Ba: Wherein, Z is the same or different each time it appears and is selected from the group consisting of O and S; X3-X8 are each independently selected from CR x or N; At least one of X3-X8 is selected from CR x , and said R x is cyano or fluorine; U1 - U4 are each independently selected from CR, either the same or different, each time they appear u ; W1-W3 are each independently selected from CR, each time they appear w ; Y1 - Y4 are each independently selected from CR, either the same or different y ; In Formula 1A, the R A has the structure represented by Formula 2 and the total number of carbon atoms in Formula 2 is greater than or equal to 2: "*" represents the connection position of Formula 2 and Formula 1A; R A1 ,R A2 ,R A3 each occurrence is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; R x ,R u ,R w ,R y each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, cyano, and combinations thereof; The substituted alkyl, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl means that any one of the groups alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl can be substituted by one or at least two selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-20 carbon atoms, unsubstituted heteroaryl having 3-20 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, cyano, and combinations thereof.

2. The metal complex according to claim 1, wherein, L b having a structure represented by Formula 1Ba: Wherein, Z is the same or different each time it appears and is selected from the group consisting of O and S; X3-X8 are each independently selected from CR x or N; At least one of X3 - X8 is selected from CR x , and said R x is cyano or fluoro; Y1 - Y4 are each independently selected from CR, either the same or different each time y ; R x ,R y is the same as or different from each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, cyano, and combinations thereof.

3. The metal complex according to claim 1, wherein, The metal complex Ir(L a ) m (L b ) 3-m has a structure represented by Formula 3: wherein, m is selected from 2, and the two Ls a are the same or different; Z is the same or different each time it appears and is selected from the group consisting of O and S; X3 - X8, each time it appears, is the same as or different from, and is selected from CR x or N; At least one of X3-X8 is selected from CR x , and said R x is cyano or fluorine; Y1 - Y4, each occurrence of which is the same as or different from, is selected from CR y ; U1 - U4 are each independently selected from CR, either the same or different, each time they appear u ; W1-W3 are each independently selected from CR, each time they appear w ; R A1 ,R A2 ,R A3 which is the same as or different from each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; R x ,R y ,R u ,R w each occurrence is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, and combinations thereof.

4. The metal complex according to any one of claims 1-3, wherein, [[ID=?]]Z is selected from the group consisting of O and S.

5. The metal complex according to claim 4, wherein, Z is O.

6. The metal complex according to claim 1 or 3, wherein Each occurrence of W1-W3 is the same as or different from and is independently selected from CR w , and / or each occurrence of U1-U4 is the same as or different from and is independently selected from CR u ; said R w and R u Each occurrence is the same as or different from and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, and Its combination.

7. The metal complex according to claim 6, wherein Said R w and R u are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and combinations thereof.

8. The metal complex according to claim 6, wherein, Said R w and R u are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and combinations thereof.

9. The metal complex according to claim 2 or 3, wherein Each occurrence of Y1 - Y4 is the same as or different from and is selected from CR y , where each occurrence of R y is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 12 carbon atoms, and combinations thereof.

10. The metal complex according to claim 9, wherein, Said R y is the same as or different from each other every time it appears and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and combinations thereof.

11. The metal complex according to claim 9, wherein, Said R y is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and combinations thereof.

12. The metal complex according to claim 1, wherein, At least one of U1-U4 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 1-20 carbon atoms, and combinations thereof.

13. The metal complex according to claim 12, wherein At least one of U1-U4 is selected from CR u , and the R u is selected from the group consisting of: substituted or unsubstituted alkyl having 3 to 12 carbon atoms, and combinations thereof.

14. The metal complex according to claim 12, wherein, The U2 or U3 is selected from CR u , and the R u is selected from substituted or unsubstituted alkyl groups having 4 to 12 carbon atoms, or a combination thereof.

15. The metal complex according to claim 1, wherein At least one of U1-U4 is selected from CR u , and the R u has a structure represented by Formula 2.

16. The metal complex according to claim 15, wherein The U2 or U3 is selected from CR u , and the R u has a structure represented by Formula 2.

17. The metal complex according to any one of claims 1-3, wherein, The R A1 , R A2 and R A3 have a total number of carbon atoms greater than or equal to 3.

18. The metal complex according to claim 17, wherein, R A1 ,R A2 ,R A3 is the same as or different from each other each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, and combinations thereof; and the total number of carbon atoms of R A1 ,R A2 and R A3 is greater than or equal to 3.

19. The metal complex according to claim 17, wherein, R A1 ,R A2 ,R A3 each occurrence of which is the same as or different from one another and is independently selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, and combinations thereof.

20. The metal complex according to any one of claims 1-3, wherein, R A1 ,R A2 ,R A3 There are two that are the same or different and are optionally selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms; and the other is optionally selected from the group consisting of deuterium, fluorine, and combinations thereof.

21. The metal complex according to any one of claims 1-3, wherein, Formula 2 is the same or different each time it appears and is selected from the group consisting of: and combinations thereof; Wherein "*" represents the connection position with Formula 1A; Optionally, the hydrogen in groups A-1 to A-19, A-24 to A-27, A-34 to A-42, A-52 to A-64, A-67 to A-72 can be partially or completely substituted by deuterium.

22. The metal complex according to any one of claims 1-3, wherein at least one of X5-X8 is selected from CR x , and the R x is cyano or fluorine.

23. The metal complex according to claim 22, wherein X7 is selected from CR x , and the R x is cyano or fluoro.

24. The metal complex according to any one of claims 1-3, wherein, At least two of X3 - X8 are selected from CR x , and one of said R x is selected from cyano or fluorine, and at least one other of said R x is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, cyano, and combinations thereof.

25. The metal complex according to claim 24, wherein, At least two of X5 - X8 are selected from CR x , and said one R x is selected from cyano or fluorine, and at least one other said R x is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, cyano, and combinations thereof.

26. The metal complex according to claim 1, wherein, L a Same or different each occurrence, selected from the group consisting of: Optionally, the hydrogen in the L a1-1 -L a1-38 , L a1-47- L a1-99 , L a1-102 , L a1-122 -L a1-123 , L a2-27 -L a2-50 , L a2-57 -L a2-73 , L a2-82 -L a2-85 , L a2-97 -L a2-116 , L aD-1 -L aD-31 , L aD-40 -L aD-76 , L aD-96 -L aD-108 , L aD-112 -L aD-118 can be partially or completely replaced by deuterium.

27. The metal complex according to claim 26, wherein, L b Same or different each occurrence, selected from the group consisting of: Optionally, the hydrogen in the above structure can be partially or completely substituted by deuterium.

28. The metal complex according to claim 27, wherein, The metal complex is selected from the structures shown in the following table, wherein the metal complex has the structure of Ir(L a )2L b , where the two L a are the same, and L a and L b respectively correspond to the structures shown in the following table:

29. An electroluminescent device, comprising: An anode, A cathode, And an organic layer disposed between the anode and the cathode, at least one layer of the organic layer contains the metal complex according to any one of claims 1-28.

30. The electroluminescent device according to claim 29, wherein, The organic layer containing the metal complex is a light-emitting layer.

31. The electroluminescent device according to claim 30, wherein, The light-emitting layer further contains a first host compound.

32. The electroluminescent device according to claim 31, wherein, The light-emitting layer further contains a second host compound.

33. The electroluminescent device according to claim 32, wherein, At least one of the host compounds contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

34. The electroluminescent device according to claim 32, 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.

35. The electroluminescent device according to claim 34, wherein, The weight of the metal complex accounts for 3% - 13% of the total weight of the light-emitting layer.

36. A compound combination, which contains the metal complex according to any one of claims 1-28. It should be noted that there seems to be an issue with the tag [[ID=?]] in the original text. It might be a mislabeled or incorrect tag. I've translated it as best as possible while keeping all other tags and text intact.

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