Metal complex, electroluminescent device and application thereof

Abstract

The present invention provides a metal complex, an electroluminescent device and application thereof. The metal complex contains a ligand L having a specific structure. a , which has a structure as shown in Formula I. a The cyano substituent contains a cyano substituent, and the design of the access site and access mode of the cyano substituent in the ligand structure, as well as the mutual cooperation between the cyano substituent and other substituents, realizes the effective improvement of the luminescent performance of the metal complex. As a phosphorescent luminescent material of an electroluminescent device, the metal complex can effectively regulate the luminescent wavelength, emit yellow light, orange light or white light, significantly improve the luminescent color and luminescent efficiency of the electroluminescent device, and significantly improve the device life, reduce the driving voltage and current density, and obtain higher luminescent current efficiency, power efficiency, external quantum efficiency and longer device life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a metal complex, an electroluminescent device and applications thereof. Background Art

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included a hole transport layer of arylamine, and an electron transport layer and a light-emitting layer of tri-8-hydroxyquinoline-aluminum; once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern OLEDs. The most advanced 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 OLED is a self-luminous solid-state device, it offers 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 the fabrication of flexible substrates.

[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and Van Slyke is a fluorescent OLED, which uses only singlet light emission, and the triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%, which limits the commercialization of fluorescent OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters, thereby being able to harvest singlet and triplet states and achieve 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds; these emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be divided into small molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer; as long as they have a precise structure, the molecular weight of a small molecule can be large; in addition, dendrimers with a well-defined structure are also considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can be converted into polymer OLEDs if post-polymerization occurs during the manufacturing process.

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

[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one or more luminescent layers to achieve the desired spectrum. Green, yellow and red phosphorescent OLEDs have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, the field of OLED devices also expects to have a more saturated emission spectrum, higher efficiency and longer device life.

[0008] Phosphorescent iridium complexes can be used as phosphorescent doping materials for the light-emitting layer and applied in the field of organic electroluminescence or display. Yellow phosphorescent materials are indispensable in lighting applications, and their performance needs to be further improved to meet the increasing performance requirements, especially to provide a method that can improve the luminescent color, reduce the driving voltage, reduce the current density and improve the quantum efficiency of the material.

[0009] US20140252333A1 discloses a Iridium complexes with the structure R 111 to R 134 At least one of X is cyano or halogenated alkyl; specific examples are This application notes that the substituent The introduction of can improve the durability of the phosphorescent material, but in all its embodiments, the external quantum efficiency is lower than 15%, and the luminous efficiency cannot meet the requirements of high-performance devices.

[0010] KR1020120032054A discloses a The iridium complex of structure is mentioned in the numerous iridium complexes disclosed by it. However, it mainly focuses on the performance of iridium complexes with substituted 2,4-diphenylpyridine ligands and substituted 2,5-diphenylpyridine ligands, and does not disclose or teach the effects of introducing specific aromatic substituents with cyano substituents at specific positions of phenylpyridine ligands and the changes in the substituents on the cyano substituents on the metal complexes.

[0011] US20100102710A1 discloses a structure of The iridium complexes of the present invention mainly focus on the iridium complexes with special framework ligands of substituted azaanthracene structures, and do not disclose and teach the influence of ligands of arylpyridine structures with cyano substituents on metal complexes.

[0012] US20170294597A1 discloses a A compound of the ligand structure, wherein when a is 0, R 7 , R 8 and R adjacent to ring B 2 At least one of them is not hydrogen. Specific examples of ligands include It mainly focuses on the fact that alkyl substitution in the peripheral ring has a better match with the molecular transition dipole moment, thereby improving the device efficiency, and does not disclose or teach the influence of ligands with cyano substituents on the peripheral ring on the metal complex.

[0013] Although some phosphorescent metal complexes have been reported in the literature, the types of materials are relatively few, and there are still shortcomings such as low luminescent color saturation, high driving voltage, and low luminous efficiency. Therefore, the development of more types and higher performance electroluminescent materials and devices remains the research focus in this field. Summary of the invention

[0014] In order to develop more types of electroluminescent materials with higher performance, one of the purposes of the present invention is to provide a metal complex having a general structural formula of M(L a ) m (L b ) n (L c ) q ;

[0015] Wherein, M is selected from metals with a relative atomic mass greater than 40;

[0016] L a , L b , L c are respectively the first ligand, the second ligand, and the third ligand coordinated with the M, and their structures are the same or different; L a , L b , L c can optionally be linked to form a tetradentate ligand or a hexadentate ligand;

[0017] m is selected from an integer of 1 to 3 (1, 2 or 3), n and q are each independently selected from an integer of 0 to 2 (0, 1 or 2); the sum of m, n, q is equal to the oxidation state of M; when m≥2, 2 or 3 L a Can be the same or different; when n = 2, 2 L b Can be the same or different; when q = 2, 2 L c Can be the same or different;

[0018] The L a Having the structure shown in Formula I:

[0019]

[0020] In Formula I, the dotted line represents the binding site between the ligand and the metal atom;

[0021] In Formula I, ring Q 1 、Ring Q 2 Each is independently selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;

[0022] In Formula I, X 1 , X 2 , X 3 , X 4 Each independently selected from CR x , CR x1 or N;

[0023] In Formula I, R q1 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0024] In Formula I, R q2 Each occurrence, identically or differently, indicates mono- or poly-substitution;

[0025] R x , R q1 , R q2each 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having 0-20 carbon atoms; and at least one R q2 It is cyano;

[0026] In Formula I, X 2 , X 3 , X 4 At least one of them is CR x1 , and R x1 The invention is selected from the group consisting of 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0027] In formula I, the adjacent substituents R q1 , R q2 can optionally be linked to form a ring;

[0028] L b , L c Each is independently selected from monoanionic bidentate ligands.

[0029] The metal complex provided by the present invention is a novel phosphorescent metal complex containing cyano substitution. In the novel phosphorescent metal complex containing cyano substitution, the luminescent performance of the metal complex is effectively improved by designing the access site and access mode of the cyano substituent in the ligand structure, and the mutual cooperation between the cyano substituent and other substituents. Compared with the phosphorescent metal complexes reported, the metal complex has the advantages of improving the luminescent color, reducing the driving voltage, reducing the current density, significantly improving the material quantum efficiency, and significantly improving the device life.

[0030] A second object of the present invention is to provide an electroluminescent device, comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex as described in one of the objects.

[0031] The third object of the present invention is to provide an application of the electroluminescent device as described in the second object in an electronic device, an electronic component module, a display device or a lighting device.

[0032] A fourth object of the present invention is to provide a compound combination, which includes the metal complex as described in one of the objects.

[0033] Compared with the prior art, the present invention has the following beneficial effects:

[0034] The present invention provides a kind of comprising specific ligand L a The metal complex, the ligand L a The cyano substituent contains a cyano substituent, and the design of the access site and access mode of the cyano substituent in the ligand structure, as well as the mutual cooperation between the cyano substituent and other substituents, realizes the effective improvement of the luminescent performance of the metal complex. As a phosphorescent luminescent material of an electroluminescent device, the metal complex can effectively regulate the luminescent wavelength, emit yellow light, orange light or white light, significantly improve the luminescent color and luminescent efficiency of the electroluminescent device, and significantly improve the device life, reduce the driving voltage and current density, and obtain higher luminescent current efficiency, power efficiency, external quantum efficiency and longer device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 A schematic diagram of an organic light-emitting device containing a metal complex and a compound combination provided by the present invention;

[0036] Figure 2 A schematic diagram of another organic light-emitting device containing the metal complex and compound combination provided by the present invention. DETAILED DESCRIPTION

[0037] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0038] OLEDs can be manufactured on a variety of substrates, such as glass, plastic or metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent US7279704B2, the entire contents of which are incorporated herein by reference.

[0039] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with 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, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0040] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. 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 sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0041] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0042] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0043] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays, vehicle displays, or taillights.

[0044] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0045] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0046] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0047] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0048] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0049] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0050] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the 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 by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0051] Definition of Substituent Terms

[0052] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0053] Alkyl - as used herein, includes straight chain and branched alkyl. Alkyl can be an alkyl with 1 to 20 carbon atoms, preferably an alkyl with 1 to 12 carbon atoms, more preferably an alkyl with 1 to 6 carbon atoms. Examples of alkyl include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, alkyl can be optionally substituted.

[0054] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0055] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is substituted by 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. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0056] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 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-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0057] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 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, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.

[0058] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.

[0059] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0060] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is an aryl group, wherein ...

[0061] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. 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, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0062] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0063] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0064] Alkylsilyl - as used herein, encompasses alkyl-substituted silicon groups. Alkylsilyl can be an alkylsilyl with 3-20 carbon atoms, preferably an alkylsilyl with 3 to 10 carbon atoms. The example of an alkylsilyl includes trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl can be optionally substituted.

[0065] Arylsilyl-as used herein, encompasses at least one aryl substituted silicon group.Arylsilyl can be an arylsilyl with 6-30 carbon atoms, preferably an arylsilyl with 8 to 20 carbon atoms.The example of arylsilyl includes triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl.In addition, arylsilyl can be optionally substituted.

[0066] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. refers to one or more CH groups in the corresponding aromatic fragment being replaced by a nitrogen atom. 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 one of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0067] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino. The invention also includes an alkyl group, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclyl group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0068] 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 a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0069] In the compounds mentioned herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred due to their enhanced efficiency and stability of the device.

[0070] In the compounds mentioned herein, polysubstituted refers to the range including disubstituted, up to the maximum number of available substitutions. When a substituent in the compounds mentioned herein represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0071] In the compounds mentioned herein, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned herein, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, 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.

[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

[0074] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0075]

[0076] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0077]

[0078] In a specific embodiment, the present invention provides a metal complex having a general structural formula of M(L a ) m (L b ) n (Lc ) q ;

[0079] Wherein, M is selected from metals with a relative atomic mass greater than 40;

[0080] L a , L b , L c are respectively the first ligand, the second ligand, and the third ligand coordinated with the M, and their structures are the same or different; L a , L b , L c can optionally be linked to form a tetradentate ligand or a hexadentate ligand;

[0081] m is an integer selected from 1 to 3, such as 1, 2 or 3; n and q are each independently selected from integers of 0 to 2, such as 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of M; when m≥2, 2 or 3 L a Can be the same or different; when n = 2, 2 L b Can be the same or different; when q = 2, 2 L c Can be the same or different;

[0082] The L a Having the structure shown in Formula I:

[0083]

[0084] In Formula I, the dotted line represents the binding site between the ligand and the metal atom;

[0085] In Formula I, ring Q 1 、Ring Q 2 Each is independently selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;

[0086] In Formula I, X 1 , X 2 , X 3 , X 4 Each independently selected from CR x , CR x1 or N;

[0087] In Formula I, R q1 Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0088] In Formula I, R q2 Each occurrence, identically or differently, indicates mono- or poly-substitution;

[0089] R x , R q1 , R q2each 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having 0-20 carbon atoms; and at least one R q2 It is cyano;

[0090] In Formula I, X 2 , X 3 , X 4 At least one of them is CR x1 , and R x1 The invention is selected from the group consisting of 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0091] In formula I, the adjacent substituents R q1 , R q2 can optionally be linked to form a ring;

[0092] L b , L c Each is independently selected from monoanionic bidentate ligands.

[0093] In this embodiment, the adjacent substituent R q1 , R q2 can be optionally connected to form a ring, which is intended to indicate that when there is a substituent R q1 , R q2 When adjacent substituent groups, for example, adjacent substituent groups R q1 Between adjacent substituents R q2 Obviously, these adjacent substituent groups may not be connected to form a ring.

[0094] In a specific embodiment, M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt.

[0095] In a preferred embodiment, the M is Pt or Ir.

[0096] In a preferred embodiment, the M is Ir.

[0097] In one embodiment, the ring Q 1 、Ring Q 2 Each occurrence is identically or differently selected from aromatic rings having 6 to 30 carbon atoms.

[0098] In a preferred embodiment, the ring Q 1 、Ring Q 2 Each occurrence is identically or differently selected from aromatic rings having 6 to 18 carbon atoms.

[0099] In a preferred embodiment, the ring Q 1 、Ring Q 2 All are benzene rings.

[0100] In a specific embodiment, the X 1 Selected from CR x ; said X 2 , X 3 , X 4 Each independently selected from CR x or CR x1 , and X 2 , X 3 , X 4 At least one of them is CR x1 .

[0101] In a specific embodiment, the X 1 Selected from CR x ; said X 2 , X 3 , X 4 Each independently selected from N, CR x or CRx1 , and X 2 , X 3 , X 4 At least one of them is CR x1 .

[0102] In a specific embodiment, the X 2 is selected from N; said X 3 , X 4 Each independently selected from CR x or CR x1 , and X 3 , X 4 At least one of them is CR x1 .

[0103] In a specific embodiment, the X 2 , X 3 , X 4 At least one of them is CR x1 , and the R x1 Selected from the group consisting of 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, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0104] In a specific embodiment, the X 2 , X 3 At least one of them is CR x1 , and / or, the X 4 CR x1 ; and said R x1 Selected from the group consisting of 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, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0105] In a preferred embodiment, the R x1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, cyclopentyl, cyclohexyl, and partially or fully deuterated versions of the above groups.

[0106] In a specific embodiment, the L b , L c Each is independently selected from any one of the following structures:

[0107]

[0108] Among them, the dotted lines represent the binding sites between the ligand and the metal atom;

[0109] R a , R b , R c Each independently represents mono-, poly- or unsubstituted;

[0110] X a Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0111] X b , X c Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0112] R a , R b , R c , R N1 , R N2 , R C1 , 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 alkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0113] Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 , R C2 Can optionally be linked to form a ring.

[0114] In this embodiment, the adjacent substituent Ra , R b , R c , R N1 , R N2 , R C1 , R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b 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, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0115] In one embodiment, the metal complex has Ir(L a ) m (L b ) 3-m The general formula of the present invention has a structure as shown in any one of Formula I-1, Formula I-2, Formula I-3, Formula I-4 or Formula I-5:

[0116]

[0117] Where m is 1 or 2; when m = 2, 2 L a Can be the same or different; when m = 1, 2 L b Can be the same or different;

[0118] R q1 , R xEach occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0119] R q2 Each occurrence, identically or differently, indicates mono- or poly-substitution;

[0120] R x , R q1 , R q2 , R 1 ~R 8 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having 0-20 carbon atoms; and at least one R q2 It is cyano;

[0121] R x1 The invention is selected from the group consisting of 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 2-20 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 amine, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0122] Adjacent substituent R q1 , Rq2 , R 1 -R 8 Can optionally be linked to form a ring.

[0123] In this embodiment, the adjacent substituent R q1 , R q2 , R 1 -R 8 can be optionally linked to form a ring, which is intended to indicate adjacent groups of substituents, for example, adjacent substituents R q1 Between adjacent substituents R q2 Between, the substituent R 1 and R 2 Between, the substituent R 2 and R 3 Between, the substituent R 3 and R 4 Between, the substituent R 4 and R 5 Between, the substituent R 5 and R 6 Between, the substituent R 6 and R 7 Between, and the substituent R 7 and R 8 Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.

[0124] In a specific embodiment, the R q1 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

[0125] The R q2 At least one of them is cyano, and the rest R q2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

[0126] In a preferred embodiment, the R q1 each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, and combinations thereof;

[0127] The R q2 At least one of them is cyano, and the rest R q2 Each occurrence is identically or differently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, cyclopentyl, cyclohexyl, substituted or unsubstituted phenyl, and combinations thereof.

[0128] In a specific embodiment, in the formula I-1, formula I-2, formula I-3, formula I-4, and formula I-5, R 1 ~R 8 At least one or two of the above are selected, at each occurrence, identically or differently, from the group consisting of: 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 cycloalkyl having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group, 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;

[0129] In a preferred embodiment, the R 1 ~R 8 At least one of the following is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, and combinations thereof.

[0130] In a specific embodiment, in the formula I-1, formula I-2, formula I-3, formula I-4, and formula I-5, R 2 , R 3 , R 6 , R 7One, two, three or all of the above are selected from the group consisting of deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0131] In a preferred embodiment, the R 2 , R 3 , R 6 , R 7 One, two, three or all of the are selected from the group consisting of deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.

[0132] In a preferred embodiment, the R 2 , R 3 , R 6 , R 7 One, two, three or all of the above are selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the above groups may be partially deuterated or fully deuterated.

[0133] In a specific embodiment, the L a Each time it appears, choose the same or different one from L a1 ~L a771 The group composed of L a1 ~L a771 Arranged in numerical order, the specific structure is as follows:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] In a specific embodiment, the L b Each time it appears, choose the same or different one from L b1 ~L b78 The group composed of L b1 ~L b78Arranged in numerical order, the specific structure is as follows:

[0167]

[0168]

[0169] In a specific embodiment, the L c It has the following structure:

[0170]

[0171] Among them, the dotted lines represent the binding sites between the ligand and the metal atom;

[0172] R Lc1 , R Lc2 , R Lc3 , R Lc4 , R Lc5 , R Lc6 , R Lc7 The alkyl radicals are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof;

[0173] Adjacent substituent R Lc1 , R Lc2 , R Lc3 , R Lc4 , R Lc5 , R Lc6 , R Lc7 Can optionally be linked to form a ring.

[0174] In this embodiment, the adjacent substituent R Lc1 , R Lc2 , R Lc3 , R Lc4 , R Lc5 , R Lc6 , RLc7 can be optionally linked to form a ring, which is intended to represent adjacent groups of substituents, for example, substituents R Lc1 With R Lc2 Between, the substituent R Lc1 With R Lc3 Between, the substituent R Lc2 With R Lc3 Between, the substituent R Lc4 With R Lc5 Between, the substituent R Lc5 With R Lc6 Between, the substituent R Lc4 With R Lc6 Between, the substituent R Lc1 With R Lc7 Between, the substituent R Lc2 With R Lc7 Between, the substituent R Lc3 With R Lc7 Between, the substituent R Lc4 With R Lc7 Between, the substituent R Lc5 With R Lc7 Between, and the substituent R Lc6 With R Lc7 In between, any one or more of these substituent groups can be connected to form a ring. Obviously, these substituent groups can also not be connected to form a ring.

[0175] In a preferred embodiment, the R Lc1 , R Lc2 , R Lc3 At least one of the following is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, and combinations thereof; and / or, said R Lc4 , R Lc5 , R Lc6 At least one of the following is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, and combinations thereof.

[0176] In a preferred embodiment, the R Lc1 , R Lc2 , R Lc3 At least two of the R are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, and combinations thereof; and / or, the R Lc4 , R Lc5 , RLc6 At least two of the above are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, and combinations thereof.

[0177] In a specific embodiment, the L c Each time it appears, choose the same or different one from L c1 ~L c360 The group composed of L c1 ~L c360 Arranged in numerical order, the specific structure is as follows:

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] In one embodiment, the metal complex has a a ) 2 (L b )、Ir(L a )(L b ) 2 、Ir(L a )(L b )(L c ) or Ir(L a )2 (L c ) any of the structures shown;

[0193] When the metal complex has Ir(L a ) 2 (L b ) structure, L a Each time it appears, choose the same or different one from L a1 ~L a771 Any one or two of the group consisting of L b Choose from L b1 ~L b78 Any of the groups consisting of;

[0194] When the metal complex has Ir(L a )(L b ) 2 When the structure of a Choose from L a1 ~L a771 Any of the groups consisting of L b Each time it appears, choose the same or different one from L b1 ~L b78 Any one or any two of the groups consisting of;

[0195] When the metal complex has Ir(L a )(L b )(L c ) structure, L a Choose from L a1 ~L a771 Any of the groups consisting of L b Choose from L b1 ~L b78 Any of the groups consisting of L c Choose from L c1 ~L c360 Any of the groups consisting of;

[0196] When the metal complex has Ir(L a ) 2 (L c ) structure, L a Each time it appears, choose the same or different one from L a1 ~L a771 Any one or two of the group consisting of L c Choose from L c1 ~L c360 Any of the groups consisting of.

[0197] In one embodiment, the metal complex is selected from the group consisting of compounds 1 to 2848; wherein compounds 1 to 2784 have Ir(L a )(L b ) 2 The structure of two L b Same; Compounds 2785-2848 have Ir(L a ) 2 (L c ) structure, where two L a The specific structures of compounds 1 to 2848 are shown in the following table:

[0198] Among them, the compounds 1 to 2784 have Ir(L a )(L b ) 2 The structure of two L b Same, L a and L b They correspond to the structures shown in the following table:

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] Compounds 2785-2848 have Ir(L a ) 2 (L c ) structure, where two L a Same, L a and L c They correspond to the structures shown in the following table:

[0235]

[0236]

[0237] The metal complex provided by the present invention can be prepared by the synthesis method disclosed in the prior art. For the sake of simplicity, the present invention will not list them one by one. Exemplarily, the synthesis route of the metal complex is as follows:

[0238]

[0239] In the above synthetic route, OTf represents trifluoromethanesulfonate, R x , R x1 , R q1 , R q2 Each independently has the same definition as in Formula I, R 1 ~R 8 The same definition as in Formula I-1 is given.

[0240] In a specific embodiment, the present invention provides an electroluminescent device, comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex as described above.

[0241] In a specific embodiment, the organic layer includes a light-emitting layer, and the light-emitting material of the light-emitting layer includes the metal complex as described above.

[0242] In a preferred embodiment, the electroluminescent device emits yellow light, orange light or white light.

[0243] In a specific embodiment, the light-emitting layer further comprises at least one host material.

[0244] In a preferred embodiment, the light-emitting layer further comprises at least two host materials.

[0245] In a preferred embodiment, at least one of the host materials contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0246] In a specific embodiment, the present invention provides a use of the electroluminescent device as described above in an electronic device, an electronic component module, a display device or a lighting device.

[0247] In a specific embodiment, the present invention provides a compound combination, which includes the metal complex as described above.

[0248] Combination with other materials

[0249] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.

[0250] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the materials disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.

[0251] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation and Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Angstrom Engineering, the optical test system produced by Suzhou Fushida, the life test system or the ellipsometer produced by Beijing Liangtuo, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents are no longer expanded in this patent.

[0252] Material synthesis example:

[0253] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0254] Synthesis Example 1

[0255] This synthesis example provides a metal complex Ir(L a1 )(L b1 ) 2 (Compound 1), the specific structure is as follows:

[0256]

[0257] The preparation method comprises the following steps:

[0258] (1) Synthesis of intermediate 1

[0259]

[0260] 2,4-Dibromo-5-methylpyridine (10.0 g, 39.9 mmol), phenylboronic acid (4.9 g, 39.9 mmol), tetrakis(triphenylphosphine)palladium Pd(PPh 3 ) 4 (2.3 g, 2.0 mmol) and potassium carbonate (16.6 g, 120.0 mmol) were dissolved in a mixed solution of 300 mL acetonitrile (MeCN) and 100 mL water. 2 Replace three times and N 2 After the reaction was completed, the reaction apparatus was placed in a heating jacket at 85°C and heated with stirring overnight. After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and purified by column chromatography to obtain intermediate 1 (8.0 g, yield 81%).

[0261] (2) Synthesis of Intermediate 2

[0262]

[0263] The intermediate 1 (8.0 g, 32.3 mmol) obtained in step (1), 4-cyanophenylboronic acid (6.2 g, 42.0 mmol), palladium acetate Pd(OAc) 2 (0.2 g, 1.0 mmol), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (X-Phos, 0.9 g, 2.0 mmol) and potassium phosphate (21.0 g, 96.9 mmol) were dissolved in a mixed solution of 240 mL of dioxane and 80 mL of water. 2 Replace three times and N 2 The reaction device was placed in a heating jacket at 100°C and heated and stirred overnight. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and separated and purified by column chromatography to obtain intermediate 2 (4.2 g, yield 48%).

[0264] (3) Synthesis of Compound 1

[0265]

[0266] The intermediate 2 (3.6 g, 13.5 mmol) obtained in step (2) and the iridium complex (6.4 g, 9.0 mmol) were dissolved in 250 mL of ethanol (EtOH) solution. 2 Permutate three times and N 2 After protection, the mixture was placed in a heating mantle at 100°C and stirred and heated under reflux overnight. After the reaction was completely cooled, the mixture was filtered through diatomaceous earth, washed twice with methanol and n-hexane respectively, and the yellow solid on top was washed with dichloromethane and the organic phase was collected and separated by column chromatography to obtain a yellow solid final product, compound 1 (0.6 g, yield 9%). The structure of the product was confirmed by mass spectrometry LCMS and was determined to be the target product with a molecular weight of 770.

[0267] 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.

[0268] Device Example 1

[0269] The present device embodiment provides an electroluminescent device, which comprises: a substrate, an ITO anode 80nm, a hole injection layer Hole transport layer Luminescent layer Hole blocking layer Electron transport layer The electron injection layer is 1nm and the cathode (aluminum) is 120nm. The preparation method is as follows:

[0270] (1) A glass substrate having an 80 nm 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 and mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were then deposited at a vacuum of approximately 10 -8 In the case of trust The rate of evaporation is carried out on the ITO anode by thermal vacuum evaporation in sequence:

[0271] (2) evaporating compound HI on the anode to serve as a hole injection layer (HIL);

[0272] (3) evaporating compound HT on the hole injection layer to serve as a hole transport layer (HTL);

[0273] (4) vapor depositing a light-emitting layer on the hole transport layer, wherein the compound 1 provided in Synthesis Example 1 of the present invention is doped in the main compound H1 and the compound H2 to serve as a light-emitting layer (EML), and the ratio of the compound H1, the compound H2 and the compound 1 is 46:46:8;

[0274] (5) Vapor depositing compound H2 on the light-emitting layer to serve as a hole blocking layer (HBL);

[0275] (6) co-depositing compound ET and 8-hydroxyquinoline-lithium (Liq) on the HBL as an electron transport layer (ETL);

[0276] (7) 1 nm of Liq was deposited on the electron transport layer as an electron injection layer (EIL), and 120 nm of Al was deposited as a cathode;

[0277] The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture getter to complete the device.

[0278] Device Comparison Example 1

[0279] The difference between Device Comparative Example 1 and Device Example 1 is that Compound 1 in step (4) is replaced by Comparative Compound 1.

[0280] Device Comparison Example 2

[0281] The difference between device comparative example 1 and device example 1 is that compound 1 in step (4) is replaced by comparative compound 2.

[0282] Device Comparison Example 3

[0283] The difference between device comparative example 1 and device example 1 is that compound 1 in step (4) is replaced by comparative compound 3.

[0284] The detailed device layer structure and thickness are shown in Table 1. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0285] Table 1 Device structures of device embodiments and comparative examples

[0286]

[0287] The material structure used in the device is shown below:

[0288]

[0289]

[0290] The compound 1 provided by the present invention

[0291] Device performance test and discussion:

[0292] The IVL and lifetime characteristics of the devices were measured at different current densities and voltages.

[0293] The external quantum efficiency (EQE), maximum emission wavelength (λ max ), current density (CD), current efficiency (CE), power efficiency (PE), voltage (V) and CIE color coordinates data, as well as 10000cd / m 2 The lifespan (LT97) of device embodiment 1 and device comparison example 1 were measured at a constant brightness of , and the test data are shown in Table 2.

[0294] Table 2 Device data

[0295]

[0296]

[0297] As can be seen from Table 2, the device examples using the metal complexes of the present invention show several advantages over the comparative compounds. Compared with device comparative example 1 (comparative compound 1), the CE, PE and EQE of device example 1 are greatly improved relative to comparative example 1, and the voltage is 0.35V lower than that of comparative example 1 using comparative compound 1 without alkyl substitution, with a decrease of more than 10%. The current density of device example 1 is 1.82 mA / cm 2 , which is significantly lower than 4.63 mA / cm of device comparison example 1 2 At the same time, CIE data show that in the compound A provided by the present invention, the ligand L a Introducing an alkyl group at the 5th position of pyridine can twist the cyanoaryl substituent and make it non-coplanar with the pyridine ring, which can effectively adjust the emission wavelength. It is also worth emphasizing that at 10000 cd / m 2 Under the conditions, the LT97 life of device embodiment 1 is 626 hours, while that of device comparison example 1 is only 192 hours, which is an obvious advantage.

[0298] The CIE color coordinates, maximum emission wavelength (λ max ), voltage (V), external quantum efficiency (EQE), and at 10000cd / m 2 The device lifespan (LT97) of device embodiment 1, device comparison example 2 and device comparison example 3 were measured under a constant brightness of ; the test data are shown in Table 3.

[0299] Table 3 Device data

[0300] Part Number CIE(x,y) <![CDATA[λ max (nm)]]> Voltage (V) EQE(%) LT97(hrs) Example 1 (0.511，0.484) 577 2.96 20.50 626 Comparative Example 2 (0.355，0.609) 537 3.11 18.13 247 Comparative Example 3 (0.340，0.618) 525 3.08 17.41 165

[0301] As can be seen from Table 3, compared with device comparative examples 2 and 3 which also use comparative compounds having an alkyl substituent at position 5 of pyridine, device embodiment 1 which uses the compound disclosed in the present invention which also has a cyano substitution on the aromatic ring of the ligand has a maximum emission wavelength of 577nm, which is an orange light material. The maximum emission wavelengths of device comparative examples 2 and 3 which have no substitution on the aromatic ring and methyl substitution on the aromatic ring are 537nm and 525nm, respectively, which are green light materials. At the same time, the driving voltage of device embodiment 1 is lower than that of device comparative examples 2 and 3, which are 0.15V and 0.08V lower, respectively. In addition, the EQE of device example 1 is 2.37% and 3.09% higher than that of device comparison example 2 and device comparison example 3, respectively, and is 13.0% higher than that of device comparison example 2 and 17.7% higher than that of device comparison example 3. This result shows that although device example 1, device comparison example 2 and device comparison example 3 all have alkyl substitution at the 5th position of ligand pyridine, device example 1 still has a significant advantage in external quantum efficiency EQE. More importantly, at 10000 cd / m 2 The LT97 lifetime of device example 1 is 626 hours, which is overwhelmingly superior to 247 hours of device comparison example 2 and 165 hours of device comparison example 3.

[0302] In summary, the metal complex disclosed in the present invention can bring about significantly improved high efficiency and low voltage excellent effects by introducing specific substituents at specific positions of the ligand through structural design, and has the excellent effects of being able to effectively adjust the luminescent wavelength and significantly improve the life of the device, indicating that the metal complex disclosed in the present invention has great advantages and broad prospects in industrial applications.

[0303] The applicant declares that the present invention illustrates a metal complex, an electroluminescent device and its application through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned process steps, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. It should be clear to those skilled in the art that any improvement to the present invention, the equivalent replacement of the raw materials selected by the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the scope of protection and disclosure of the present invention. Many of the materials and structures described herein can be replaced by other materials and structures without departing from the spirit of the present invention. It should be understood that various theories about why the present invention works are not intended to be limiting.

Claims

1. A metal complex, characterized in that The general structural formula of the metal complex is Ir(L a ) m (L b ) 3-m ; and having the structure shown in formula I-1: Among them, m is 1, 2 L b Can be the same or different; L a , L b They are respectively a first ligand and a second ligand coordinated with the Ir, and their structures are the same or different; R q1 , R x Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; R q2 Each occurrence, identically or differently, indicates mono- or poly-substitution; R1~R8、R x , R q1 , R q2 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, cyano, and combinations thereof; and at least one R q2 It is cyano; R x1 Selected from: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; The substituted alkyl group refers to an alkyl group that may be substituted by one or more deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, cyano, and combinations thereof.

2. The metal complex according to claim 1, characterized in that The R x1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, and partially or fully deuterated versions of the above groups.

3. The metal complex according to claim 1, characterized in that The metal complex has a structure as shown in Formula I-1: Among them, m is 1, 2 L b Can be the same or different; R q1 , R x Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; R q2 Each occurrence indicates a single substitution; R x , R q1 , R1-R8 are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, and combinations thereof at each occurrence, the same or different; R q2 Selected from: cyano; R x1 Selected from: substituted or unsubstituted alkyl groups having 1 to 12 carbon atoms.

4. The metal complex according to claim 1, characterized in that The R q1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, and combinations thereof; The R q2 At least one of them is cyano, and the rest R q2 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium.

5. The metal complex according to claim 1, characterized in that The R q1 each occurrence being identically or differently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, and combinations thereof; The R q2 At least one of them is cyano, and the rest R q2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, and combinations thereof.

6. The metal complex according to claim 1, characterized in that In formula I-1, at least one or two of R1 to R8 are selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, and combinations thereof, the same or different when each occurs.

7. The metal complex according to claim 1, characterized in that At least one of R1 to R8 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

8. The metal complex according to claim 1, characterized in that In formula I-1, one, two, three or all of R2, R3, R6 and R7 are selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and combinations thereof.

9. The metal complex according to claim 1, characterized in that One, two, three or all of R2, R3, R6 and R7 are selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and combinations thereof.

10. The metal complex according to claim 1, characterized in that One, two, three or all of R2, R3, R6 and R7 are selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; optionally, the above groups may be partially deuterated or fully deuterated.

11. The metal complex according to claim 1, characterized in that The L a Each occurrence is identically or differently selected from the group consisting of: The dotted lines represent the binding sites between the ligand and the metal atom.

12. The metal complex according to claim 11, characterized in that The L b Each occurrence is identically or differently selected from the group consisting of: The dotted lines represent the binding sites between the ligand and the metal atom.

13. The metal complex according to claim 12, characterized in that The metal complex has a a )(L b ) The structure shown in 2; L a Choose from: Any of the groups consisting of L b Each time it appears, choose the same or different one from L b1 ~L b78 Any one or any two of the group consisting of.

14. The metal complex according to claim 12, characterized in that The metal complex is selected from the group consisting of the following compounds, wherein two L b Same, L a and L b They correspond to the structures shown in the following table:

15. An electroluminescent device, characterized in that: The electroluminescent device comprises a cathode and an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 14.

16. The electroluminescent device according to claim 15, characterized in that The organic layer comprises a light-emitting layer, and the light-emitting material of the light-emitting layer comprises the metal complex according to any one of claims 1 to 14.

17. The electroluminescent device according to claim 15, characterized in that The electroluminescent device emits yellow light, orange light or white light.

18. The electroluminescent device according to claim 16, characterized in that The light-emitting layer further includes at least one host material.

19. The electroluminescent device according to claim 16, characterized in that The light-emitting layer further comprises at least two host materials.

20. The electroluminescent device according to claim 19, characterized in that At least one of the host materials comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

21. Use of the electroluminescent device according to any one of claims 15 to 20 in an electronic device, an electronic component module, a display device or a lighting device.

22. A compound combination, characterized in that The compound combination comprises the metal complex according to any one of claims 1 to 14.

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