Organic electroluminescent material and device thereof

Abstract

To provide an organic electroluminescent material and a device thereof.SOLUTION: The organic electroluminescent material is a metal complex containing a ligand La having a structure of Formula 1A and a ligand Lb having a structure of Formula 1B. Such metal complexes can give a higher sublimation yield during sublimation and have a lower evaporation temperature. Applying them to electroluminescent devices can provide, for example, better device performance such as an increased device lifetime and a narrower full width at half maximum. Further provided are an electroluminescent device containing the metal complex and a compound composition containing the metal complex.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound for use in an organic electronic device such as an organic light-emitting device. More particularly, the present invention relates to a compound having a structure represented by Formula 1A, a The ligand and L of the structure represented by formula 1B b The present invention relates to a metal complex containing the ligand, an organic electroluminescent device containing the metal complex, and a combination of compounds. [Background technology]

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device containing an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and emissive layers (Applied Physics Letters, 1987, 51(12):913-915). Once a bias was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may contain multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. As self-emissive solid-state devices, OLEDs offer tremendous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them highly suitable for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs are divided into three different types depending on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. Triplets generated in the device are wasted through nonradiative decay pathways, resulting in an internal quantum efficiency (IQE) of only 25%, hindering the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs, which use triplet emission from heavy metal-containing complexes as the emitter. Therefore, singlet and triplet emissions can be harvested, achieving an IQE of 100%. Due to their 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, allowing excitons to transition from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons by triplet excitons threading between reverse systems (reverse intersystem crossing).

[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material used. Small molecules refer to non-polymeric organic or organometallic materials, and as long as they have a precise structure, the molecular weight of the small molecule can be large. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Post-polymerization during the manufacturing process can turn small molecule OLEDs into polymer OLEDs.

[0006] Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of an OLED can be achieved by the structural design of the emissive material. An OLED may contain one or more emissive layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still suffer from problems such as unsaturated blue, short service life, and high operating voltage. Commercially available full-color OLED displays generally use a mixed strategy, employing blue fluorescence and yellow, red, or green phosphorescence. Currently, phosphorescent OLEDs suffer from a rapid decrease in efficiency at high brightness. Furthermore, there is a demand for more saturated emission spectra, higher efficiency, and longer device service life.

[0008] Cyano group substitution is not always introduced into phosphorescent metal complexes, such as iridium complexes. US20140252333A1 discloses a series of iridium complexes substituted with cyano-phenyl groups, but the results do not clearly demonstrate the effect of the cyano group. Also, for example, US20040121184A1 uses cyano groups, which are highly electron-withdrawing substituents, to produce blue-shifted phosphorescent metal complexes. The applicant's basic application US20200251666A1 discloses metal complexes with cyano-substituted ligands, which, when used in organic electroluminescent devices, can improve the device's performance and color saturation, achieving a high level within the industry, but there is still room for improvement.

[0009] To emit red light, alkyl group substitution has been introduced into phosphorescent metal complexes, such as iridium complexes. US2014231755A1 discovered that deuterium addition of a methyl group at the 5-position of 2-phenylpyridine can improve the service life of the device. [Prior art documents] [Patent documents]

[0010] [Patent Document 1] U.S. Patent Application Publication No. 20140252333A1 [Patent Document 2] U.S. Patent Application Publication No. 20040121184A1 [Patent Document 3] U.S. Patent Application Publication No. 20200251666A1 [Patent Document 4] U.S. Patent Application Publication No. 2014231755A1 [Non-patent literature]

[0011] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]

[0012] In order to solve at least part of the above-mentioned problems, the present invention provides a compound having a structure represented by formula 1A, a The ligand and L of the structure represented by formula 1B b The present invention aims to provide a series of metal complexes containing a ligand. The metal complexes can be used as light-emitting materials in electroluminescent devices. These novel compounds can achieve higher sublimation yields and lower deposition temperatures upon sublimation. When used in electroluminescent devices, the present invention can provide better device performance, such as an improved device lifespan and a narrower full width at half maximum. [Means for solving the problem]

[0013] According to one embodiment of the present invention, M(L a ) m (L b ) n (L c ) q Disclosed are metal complexes having the general formula: (L a , Lb and L c are the primary, secondary, and tertiary ligands that coordinate with the metal M, respectively, and L c is the L a or L b Same or different from L a , L b and L c may be linked to form a multidentate ligand; the metal M is selected from metals with a relative atomic mass greater than 40, preferably the metal M is selected, identically or differently at each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, more preferably M is selected, identically or differently at each occurrence, from Pt or Ir; m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q is equal to the oxidation state of M. When m is 2, two L a are the same or different, and if n is 2, the two L b are the same or different, L a each occurrence may be the same or different and have the structure of Formula 1A; L b has the structure of Formula 1B, which may be the same or different at each occurrence, [ka] Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X1 to X8 are C or CR, each occurrence may be the same or different. x Selected from Y1 to Y4 may be the same or different for each occurrence. y or selected from N, U1 to U4 are the same or different CRs for each occurrence. u or selected from N, W1 to W4 are the same or different for each occurrence. w or selected from N, R, R x , R y , R u , R ware the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; At least one or more of U1 to U4 is CR u wherein R u is 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, or a combination thereof, and all of the R u The sum of the carbon atoms in R x at least one of is a cyano group; Adjacent substituents R and R x , R y , R u , R w may be bonded to form a ring, L c may be the same or different for each occurrence. [ka] and is selected from structures represented by any one of the groups consisting of: R a , R b and R care the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 , C.R. C1 R C2 selected from the group consisting of R a , R b , R c , R N1 , R C1 and R C2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may be bonded to form a ring.

[0014] According to another embodiment of the present invention, there is further disclosed an electroluminescent device including an anode, a cathode, and organic layers disposed between the anode and the cathode, wherein at least one of the organic layers contains the metal complex described in the above-described embodiment.

[0015] According to other embodiments of the present invention, there are further disclosed combinations of compounds comprising the metal complexes described in the above examples.

[0016] L of the structure represented by formula 1A according to the present invention a The ligand and L of the structure represented by formula 1B b A series of metal complexes containing the ligand L a By introducing specific substituents into the ligand, L b By introducing a cyano group into the ligand, these novel compounds can achieve higher sublimation yields and lower deposition temperatures during sublimation. These metal complexes can be used as luminescent materials in electroluminescent devices. When used in electroluminescent devices, the present invention can provide better device performance, such as improved device life and narrower full width at half maximum. [Brief explanation of the drawings]

[0017] [Figure 1] 1 is a schematic diagram of an organic light emitting device that may include a combination of metal complexes and compounds according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light emitting device that may include a combination of metal complexes and compounds according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0018] OLEDs can be fabricated on a variety of substrates, including glass, plastic, and metal. FIG. 1 illustrates, by way of example and not limitation, an organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted from the drawings, if necessary. 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, an emissive layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. Device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0019] There are many examples of each of these layers. Illustratively, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., incorporated herein by reference in its entirety. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin metal layer, such as Mg:Ag, coated thereon with a sputter-deposited transparent conductive ITO layer. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties, describe the principles and use of blocking layers in more detail. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, provides examples of injection layers. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, describes protective layers.

[0020] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0021] 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.

[0022] An OLED also requires an encapsulation layer. As shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 to protect against harmful substances, such as moisture and oxygen, from the outside. Any material capable of providing an encapsulation function, such as glass or an organic-inorganic hybrid layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the exterior of the OLED device. Multilayer thin-film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0023] Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lamps, head-up displays, fully or partially transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and tail lights.

[0024] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0025] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is relatively far from the substrate. Other layers may be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if various organic layers are present between the cathode and anode.

[0026] "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.

[0027] It is believed that if a ligand directly enhances the photosensitizing properties of the emitting material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emitting material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand can modify the properties of the photosensitizing ligand.

[0028] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistics limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0029] On the other hand, E-type delayed fluorescence relies on the conversion of triplet and singlet excited states rather than the collision of two triplets. Compounds capable of generating E-type delayed fluorescence must have an extremely small singlet-triplet gap to allow for the energy state conversion. Thermal energy can activate the triplet-to-singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading between reverse intersystems (RISC) is sufficiently fast, the non-radiative decay from the triplet can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlets can be 100%, far exceeding the 25% spin statistics of the exciton due to electrochemical reactions.

[0030] The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T ) is required. Organic non-metal-containing donor-acceptor emissive materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, ΔE S-T These states may include CT states. Donor-acceptor emissive materials are typically constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0031] Definitions of Substituent Terminology

[0032] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0033] As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. Illustrative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. The alkyl group may be substituted.

[0034] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may be substituted.

[0035] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisopropyl. Heteroalkyl groups may also be substituted.

[0036] As used herein, the term "alkenyl group" includes linear, branched, and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 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 norbornylalkenyl groups. The alkenyl groups may be substituted.

[0037] As used herein, the term "alkynyl group" includes straight-chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups 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, and phenylpropynyl groups. Of these, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. The alkynyl group may be substituted.

[0038] As used herein, the term "aryl group" or "aromatic group" refers to both non-fused and fused systems. 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, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-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-dimethylphenyl, mesitylene, and m-tetraphenyl. The aryl group may also be substituted.

[0039] As used herein, the term "heterocyclic group" or "heterocycle" refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Heterocyclic groups may also be substituted.

[0040] As used herein, the term "heteroaryl group" refers to both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. The term "isoaryl group" also refers to heteroaryl groups. The heteroaryl group may be a heteroaryl group containing 3 to 30 carbon atoms, preferably a heteroaryl group containing 3 to 20 carbon atoms, and more preferably a heteroaryl group containing 3 to 12 carbon atoms. Suitable heteroaryl groups 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, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Heteroaryl groups may also be substituted.

[0041] As used herein, the alkoxy group refers to an -O-alkyl group, an -O-cycloalkyl group, an -O-heteroalkyl group, or an -O-heterocyclic group. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group, and the heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may be substituted.

[0042] As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.

[0043] As used herein, the term "aralkyl group" includes an alkyl group substituted with an aryl group. 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 the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.

[0044] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is 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. The alkylsilyl group may also be substituted.

[0045] As used herein, the term "arylsilyl group" refers to a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.

[0046] The "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the replacement of one or more C—H groups in the corresponding aromatic fragment with 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. Those skilled in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.

[0047] In the present invention, unless otherwise specified, when any term from the group consisting of substituted alkyl group, substituted cycloalkyl group, substituted heteroalkyl group, substituted heterocyclic group, substituted aralkyl group, substituted alkoxy group, substituted aryloxy group, substituted alkenyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted amino group, substituted acyl group, substituted carbonyl group, substituted carboxyl group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, and substituted phosphino group is used, any one group from the group consisting of alkyl group, cycloalkyl group, heteroalkyl group, heterocyclyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is included. , deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted 6 carbon atoms This means that the aryl group may be substituted with one or more groups selected from an aryl group having from 3 to 30 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amino group having from 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0048] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.

[0049] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.

[0050] In the compounds referred to herein, multiple substitution refers to the range up to the most available substitution, including double substitution.When a substituent in a compound referred to herein means multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on its bond structure, and the substituents present at all multiple available substitution positions may be the same structure or different structures.

[0051] Unless specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, and adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents are not bonded to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such descriptions, adjacent substituents may 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 apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0052] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0053] [ka]

[0054] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0055] [ka]

[0056] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. An example is shown in the following formula.

[0057] [ka]

[0058] According to one embodiment of the present invention, M(L a ) m (L b ) n (L c ) q Disclosed are metal complexes having the general formula: (L a , L b and L c are the primary, secondary, and tertiary ligands that coordinate with the metal M, respectively, and L c is the L a or L b Same or different from L a , L b and L c may be linked to form multidentate ligands, for example, L a , L b and L c Any two of may be linked to form a tetradentate ligand, and for example, L a , L b and L c may be linked together to form a hexadentate ligand, and for example, L a , L b , L c may not all be linked to form a multidentate ligand, the metal M is selected from metals with a relative atomic mass greater than 40, preferably the metal M is selected, identically or differently at each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, more preferably M is selected, identically or differently at each occurrence, from Pt or Ir; m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q is equal to the oxidation state of M. When m is 2, two L a are the same or different, and if n is 2, the two L b are the same or different, L a each occurrence may be the same or different and have the structure of Formula 1A; L b has the structure of Formula 1B, which may be the same or different at each occurrence, [ka] Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X1 to X8 are C or CR, each occurrence may be the same or different. x Selected from Y1 to Y4 may be the same or different for each occurrence. y or selected from N, U1 to U4 are the same or different CRs for each occurrence. u or selected from N, W1 to W4 are the same or different for each occurrence. w or selected from N, R, R x , R y , R u , R ware the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; At least one or more of U1 to U4 is CR u wherein R u is 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, or a combination thereof, and all of the R u The sum of the carbon atoms in R x at least one of is a cyano group; Adjacent substituents R and R x , R y , R u , R w may be bonded to form a ring, L c may be the same or different for each occurrence. [ka] and is selected from structures represented by any one of the groups consisting of: R a , R b and R care the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 , C.R. C1 R C2 selected from the group consisting of R a , R b , R c , R N1 , R C1 and R C2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may be bonded to form a ring.

[0059] As used herein, "all of the R u The sum of the carbon atoms of U1 to U4 is at least 4, and the sum of the carbon atoms of U1 to U4 is at least 4. u and wherein R uis 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, or a combination thereof. u This means that the sum of the carbon atoms in the substituents is 4 or more. When one of U1 to U4 satisfies the above condition, the number of carbon atoms in the substituent is 4 or more. When two of U1 to U4 satisfy the above condition, the sum of the carbon atoms in the two substituents is 4 or more. When three of U1 to U4 satisfy the above condition, the sum of the carbon atoms in the three substituents is 4 or more. When four of U1 to U4 satisfy the above condition, the sum of the carbon atoms in the four substituents is 4 or more. For example, when U2 is CR u and when the above conditions are satisfied, the substituent R u The sum of the carbon atoms in U3 is 4 or more. u and when the above conditions are satisfied, the substituent R u The sum of the carbon atoms in the aryl group is 4 or more. In other cases, the analogy is as follows:

[0060] In the examples, "adjacent substituents R, R x , R y , R u , R w may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R, two substituents R x two substituents R y two substituents R u two substituents R w two substituents R w and R u two substituents R y and R x This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0061] In the present specification, "adjacent substituents R a , R b , R c , R N1 , RC1 and R C2 may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a two substituents R b two substituents R c R a and R b R a and R c R b and R c R a and R N1 R b and R N1 R a and R C1 R a and R C2 R b and R C1 R b and R C2 R C1 and R C2 This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0062] According to one embodiment of the present invention, L b has a structure represented by formulas 1Ba to 1Bd.

[0063] [ka] (Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; In Formula 1Ba, X3 to X8 may be the same or different at each occurrence and may be CR x Selected from In formula 1Bb, X1 and X4 to X8 may be the same or different at each occurrence and may be CR x Selected from In Formula 1Bc and Formula 1Bd, X1 to X2 and X5 to X8 may be the same or different at each occurrence and may be CR x Selected from Y1 to Y4 may be the same or different for each occurrence. y or selected from N, R, R x , R y are the same or different at each occurrence and each represents hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R and R x , R y may be bonded to form a ring.

[0064] In the examples, "adjacent substituents R, R x , R y may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R, two substituents R x two substituents R y two substituents R y and R x This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0065] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 2:

[0066] [ka] (m is chosen from 1 or 2. When m=1, two L b are the same or different, and when m=2, two L a are the same or different, Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and when two R are present simultaneously, the two R are the same or different; X3 to X8 are the same or different CRs for each occurrence. x Selected from Y1 to Y4 may be the same or different for each occurrence. y or selected from N, U1 to U4 are the same or different CRs for each occurrence. u or selected from N, W1 to W4 are the same or different for each occurrence. w or selected from N, R, R x , R y , R u , R ware the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; At least one or more of U1 to U4 is CR u and wherein R u is 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, or a combination thereof, and all of the R u The sum of the carbon atoms in R x at least one of is a cyano group; Adjacent substituents R and R x , R y , R u may be bonded to form a ring.

[0067] In the examples, "adjacent substituents R, R x , R y , R u may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R, two substituents R x two substituents R y two substituents R utwo substituents R y and R x This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0068] According to one embodiment of the present invention, Z is selected from O and S.

[0069] According to one embodiment of the present invention, Z is O.

[0070] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R x is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring 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 is selected from the group consisting of an 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0071] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R xis selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.

[0072] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R x is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0073] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R x is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.

[0074] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R x is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0075] According to one embodiment of the present invention, the R x is a cyano group, and at least one other R xis selected from the group consisting of fluorine, deuterium, a methyl group, a deuterated methyl group, a deuterated isopropyl group, a cyclohexyl group, a deuterated cyclohexyl group, a phenyl group, a deuterated phenyl group, a methylphenyl group, and a deuterated methylphenyl group.

[0076] According to one embodiment of the present invention, CRs X5 to X8 x At least one of them is CR x and the R x is a cyano group.

[0077] According to one embodiment of the present invention, CRs X7 to X8 x At least one of the x and the R x is a cyano group.

[0078] According to one embodiment of the present invention, the X7 x and the R x is a cyano group.

[0079] According to one embodiment of the present invention, the X8 x and the R x is a cyano group.

[0080] According to one embodiment of the present invention, U1 to U4 may be the same or different for each occurrence. u and R u At least one of the R is selected from 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, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0081] According to one embodiment of the present invention, U1 to U4 may be the same or different for each occurrence and may be N or CR u and at least one is selected from CR u and R uis 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, or a combination thereof, and u The sum of the carbon atoms is at least 4.

[0082] According to one embodiment of the present invention, R u At least one of the groups is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof.

[0083] According to one embodiment of the present invention, R u At least one of [ka] and combinations thereof, preferably, the hydrogen atoms in the above groups are partially or completely deuterated; The symbol "*" indicates the bonding point between the substituent and the carbon.

[0084] According to one embodiment of the present invention, R u At least one of the groups is selected from a substituted or unsubstituted alkyl group having 4 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 6 carbon atoms, or a combination thereof.

[0085] According to one embodiment of the present invention, U2 or U3 is u and the R u is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, or a combination thereof.

[0086] According to one embodiment of the present invention, U2 or U3 is u and R u may be the same or different at each occurrence, and uis selected from a substituted or unsubstituted alkyl group having 4 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 6 carbon atoms, or a combination thereof.

[0087] According to one embodiment of the present invention, U2 and U3 are u and the R u are the same or different at each occurrence and are selected from 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, or a combination thereof, and at least one R u The substituent has 4 or more carbon atoms.

[0088] According to one embodiment of the present invention, U1 and U4 are u and R u is selected from hydrogen, deuterium, a methyl group, and a deuterated methyl group.

[0089] According to one embodiment of the present invention, W1 to W4 may be the same or different for each occurrence. w Y1 to Y4 are the same or different for each occurrence. y and R w and R y are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0090] According to one embodiment of the present invention, R w and R y are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and combinations thereof.

[0091] According to one embodiment of the present invention, Rw and R y and each occurrence may be the same or different and are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, and combinations thereof.

[0092] According to one embodiment of the present invention, W1 to W4 may be the same or different for each occurrence. w and at least one R w are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 ring 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, and combinations thereof, and / or Y1 to Y4 are the same or different at each occurrence and are selected from the group consisting of CR y and at least one R y is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0093] According to one embodiment of the present invention, R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0094] According to one embodiment of the present invention, R is selected from a methyl group or a deuterated methyl group.

[0095] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a206 L a1 ~L a206 The specific structure is shown in claim 17.

[0096] According to one embodiment of the present invention, Lb may be the same or different for each occurrence of L b1 ~L b972 L b1 ~L b972 The specific structure is shown in claim 18.

[0097] According to one embodiment of the present invention, the metal complex is Ir(L a )2L b It has a structure of two L a are identical, and L a L a1 ~L a206 L a1 ~L a206 A specific structure of is shown in claim 17. b L b1 ~L b972 L b1 ~L b972 The specific structure is shown in claim 18.

[0098] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 448. Specific structures of metal complex 1 to metal complex 448 are set forth in claim 19.

[0099] According to one embodiment of the present invention, there is further disclosed an electroluminescent device including an anode, a cathode, and organic layers disposed between the anode and the cathode, wherein at least one of the organic layers contains the metal complex described in any one of the above-described embodiments.

[0100] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent device is a light-emitting layer.

[0101] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element emits green light.

[0102] According to an embodiment of the present invention, the light-emitting layer in the electroluminescent device further comprises at least one first host compound.

[0103] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent device further comprises at least one first host compound and at least one second host compound.

[0104] According to one embodiment of the present invention, the at least one host compound in the electroluminescent device comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0105] According to one embodiment of the present invention, the first host compound has a structure represented by Formula 3:

[0106] [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; V may be the same or different for each occurrence. v or N, and at least one of V is C, and L x is combined with T may be the same or different for each occurrence, and may be C, CR t or N, and at least one of T is C, and Lx is combined with R v and R t are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is 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; Adjacent substituents R v and R t may be bonded to form a ring.

[0107] In the examples, "adjacent substituents R v and R t may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v two substituents R t two substituents R v and R t This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0108] According to one embodiment of the present invention, the first host compound has a structure represented by one of Formulas 3-a to 3-j.

[0109] [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; V may be the same or different for each occurrence. v or selected from N, T may be the same or different for each occurrence. t or selected from N, R v and R t are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is 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; Adjacent substituents R v and R t may be bonded to form a ring.

[0110] According to one embodiment of the present invention, in the electroluminescent device, when the metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 1% to 30% of the total weight of the light-emitting layer.

[0111] According to one embodiment of the present invention, in the electroluminescent device, when the metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 3% to 13% relative to the total weight of the light-emitting layer.

[0112] According to another embodiment of the present invention, there is further disclosed a combination of compounds containing a metal complex, the specific structure of which is shown in any one of the above-mentioned embodiments.

[0113] Combination with other materials

[0114] The materials of the specific layers used in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132 to 0161 of U.S. Patent Application No. US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. The materials described or referenced 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 refer to the literature to identify other materials that can be used in combination.

[0115] It is stated herein that the materials of specific layers used in organic light-emitting devices can be used in combination with various other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with various hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned 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 refer to the literature to identify other materials that can be used in combination.

[0116] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, a differential scanning calorimeter, a Shanghai Lingguang Technology fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system, a service life test system from Suzhou Fusida, an ellipsometer from Beijing Liangtuo, and the like) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification. [Example]

[0117] Examples of material synthesis:

[0118] The preparation method of the compound according to the present invention is not limited. Taking the following compound as a typical but non-limiting example, its synthetic route and preparation method are as follows:

[0119] Synthesis Example 1: Synthesis of Metal Complex 13 [ka]

[0120] Intermediate 1 (1.6 g, 4.6 mmol), iridium complex 1 (3.18 g, 3.8 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added to a dry 250 mL round-bottom flask in this order. The reaction was heated at 90 °C for 144 h under N2 protection. After the reaction cooled, it was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 13 (0.82 g, 22.3% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 958.3.

[0121] Synthesis Example 2: Synthesis of Metal Complex 7 [ka]

[0122] Intermediate 2 (1.0 g, 2.9 mmol), iridium complex 1 (2.2 g, 2.6 mmol), 2-ethoxyethanol (40 mL), and DMF (40 mL) were added to a dry 250 mL round-bottom flask in this order. The reaction was heated at 100 °C for 120 h under N2 protection. After the reaction cooled, it was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain metal complex 7 (0.45 g, 18.1% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 958.3.

[0123] Synthesis Example 3: Synthesis of Metal Complex 17 [ka]

[0124] Intermediate 3 (1.2 g, 4.5 mmol), iridium complex 1 (2.5 g, 3.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added to a dry 250 mL round-bottom flask in this order. The reaction was carried out at 90 °C under N2 protection for 144 h. After the reaction cooled, it was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain metal complex 17 (0.73 g, 25.3% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 963.3.

[0125] Synthesis Example 4: Synthesis of Metal Complex 163 [ka]

[0126] A 250 mL dry round-bottom flask was charged with intermediate 1 (1.3 g, 3.7 mmol), iridium complex 2 (2.2 g, 2.6 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), in that order. The reaction was heated at 90 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 163 (0.78 g, 30.4% yield) as a yellow solid. The product was confirmed to be the target product with a molecular weight of 986.3.

[0127] Synthetic Example 5: Synthesis of Metal Complex 43 [ka]

[0128] A 250 mL dry round-bottom flask was charged with intermediate 1 (1.5 g, 4.9 mmol), iridium complex 3 (3.0 g, 3.6 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL), in that order. The reaction was heated at 95 °C for 144 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth and washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 43 (1.23 g, 35.4% yield) as a yellow solid. The structure of the product was confirmed as the target product with a molecular weight of 964.4.

[0129] Those skilled in the art should know that the above preparation methods are merely exemplary and can be modified to obtain the structures of other compounds of the present invention.

[0130] Element Example 1

[0131] First, a glass substrate with 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 water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8In the case of a 1000-kV device, the following materials were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.2 to 2 Å / s. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transport layer (HTL). Compound H1 was used as an electron blocking layer (EBL). Then, metal complex 13 of the present invention was doped into compounds H1 and H2 to form an emitting layer (EML). Compound H2 was used as a hole blocking layer (HBL) on the EML. Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL to form an electron transport layer (ETL). Finally, a 1-nm-thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as an electron injection layer, and 120 nm of aluminum was deposited as a cathode. The device was then transferred to a glove box and encapsulated using a glass cover and a moisture absorbent to complete the device.

[0132] Element Example 3

[0133] The embodiment of Device Example 3 is similar to Device Example 1, except that Compound Metal Complex 17 replaces Metal Complex 13 according to the present invention in the light-emitting layer (EML).

[0134] Comparative Example 1 of the Element

[0135] The embodiment of Comparative Example 1 of the device is similar to that of Example 1 of the device, except that the compound GD1 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0136] Comparative example 2 of the element

[0137] The embodiment of Comparative Example 2 of the device is similar to that of Example 1 of the device, except that the compound GD2 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0138] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0139] [Table 1]

[0140] The structure of the material used in the element is represented as follows:

[0141] [ka]

[0142] The IVL characteristics of the element were measured. 2 The CIE data of the element, maximum radiation wavelength λ max The deposition temperature (Sub T) of the material was set at a vacuum level of approximately 10 -8 Torr is the temperature measured during hot vacuum deposition of metal complexes at a rate of 0.2 Å / s. Lifetime (LT97) data is based on 80 mA / cm 2 These data are recorded and displayed in Table 2.

[0143] [Table 2]

[0144] As can be seen from the data in Table 2, the full width at half maximum of Example 1 was 3.3 nm narrower than that of Comparative Example 1 and 3.0 nm narrower than that of Comparative Example 2. At the same time, the deposition temperature of Example 1 was approximately 33°C lower than that of Comparative Example 1 and approximately 29°C lower than that of Comparative Example 2. The lower deposition temperature contributes to maintaining the stability of the complex of the present invention during the deposition process, contributing to the industrial application of materials and reducing energy consumption. Furthermore, the service life of Example 1 was increased by 51.5% compared to Comparative Example 1, and the service life of Example 1 was also improved by 15.4% compared to Comparative Example 2. Similarly, in Example 3, the use of metal complex 17 in the device resulted in a full width at half maximum of 4.6 nm and 4.3 nm narrower than that of Comparative Example 1 and Comparative Example 2, respectively, and the service life of the device was improved by 88.5% and 43.6%, respectively, despite the deposition temperature being reduced by approximately 40°C and 37°C. That is, the overall performance of the device is greatly improved due to the narrower full width at half maximum, lower deposition temperature, and significantly improved device life.

[0145] Metal complex 13 used in Example 1 and metal complexes GD1 and GD2 used in Comparative Examples 1 and 2 have the same ligand L b and just L a The only difference was the substituents on the ligand. In the examples, L a The metal complex 17 used in Example 3 further contained L b The deuterium substitution in the ligand further improves each performance of the device, ultimately improving the overall performance of the device.

[0146] Element Example 2

[0147] The embodiment of Device Example 2 is similar to Device Example 1, except that Metal Complex 7 is replaced by Metal Complex 13 according to the present invention in the light-emitting layer (EML).

[0148] Comparative Example 3 of the Element

[0149] The embodiment of Comparative Example 3 of the device is similar to that of Example 1 of the device, except that the compound GD3 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0150] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0151] [Table 3]

[0152] The structure of the new material used in the device is represented as follows:

[0153] [ka]

[0154] The IVL characteristics of the element were measured. 2 The CIE data of the element, maximum radiation wavelength λ max The deposition temperature (Sub T) of the material was set at a vacuum level of approximately 10 -8 Torr is the temperature measured during hot vacuum deposition of metal complexes at a rate of 0.2 Å / s. Lifetime (LT97) data is based on 80 mA / cm 2 These data are recorded and displayed in Table 4.

[0155] [Table 4]

[0156] As can be seen from the data in Table 4, the full width at half maximum of the device in Example 2 is 2.3 nm narrower than that of the device in Comparative Example 3, and the deposition temperature is about 26°C lower than that of Comparative Example 3. In addition, the service life of Example 2 is improved by 16.4% compared to Comparative Example 3. Metal complex 7 used in Example 2 and metal complex GD3 used in Comparative Example 3 have the same ligand L b and just L a The only difference was the substituents on the ligands. Example 2 had a narrower full width at half maximum, a lower deposition temperature, and a better device life than Comparative Example 3, again demonstrating the superior effect of the present invention.

[0157] Sublimation Data

[0158] The metal complexes of the present invention and the comparative compounds were sublimated using a sublimation apparatus, model number BOF-A1-3-60, manufactured by Anhui Beike Equipment Co., Ltd. Metal complexes 13, 17, and 7 of the present invention, and comparative complexes GD1, GD2, and GD3 were each placed in the sublimation tube of the sublimation apparatus, and a molecular pump was used to create a vacuum of 9.9 × 10 in the sublimation tube. -4 The metal complexes were obtained by heating the materials to 300-370°C and stably sublimating them. The sublimation yields of these materials are shown in Table 5. The sublimation yield is the ratio of the mass after sublimation to the mass before sublimation.

[0159] [Table 5]

[0160] As can be seen from the data in Table 5, the L aMetal complexes 13 and 17, which have specific substituents on the ligands, exhibited good sublimation performance, with sublimation yields reaching 85.3% and 88.8%, respectively, which were approximately 1.6 and 1.7 times higher than the sublimation yield of comparative compound GD1 (32.8%). Similarly, the sublimation yield of comparative compound GD2 (58.9%) was improved by 44.8% and 50.7%, respectively. Furthermore, the sublimation yield of metal complex 7 reached 71.1%, which was improved by 45.6% compared to the sublimation yield of comparative compound GD3 (48.8%). As a result, the L a Metal complexes in which specific (cyclo)alkyl group substitutions have been introduced into the ligand structure have higher sublimation yields than metal complexes that do not have these specific substitutions, and a significant improvement in sublimation yield is not expected. Therefore, improvement in sublimation yield is of great significance for realizing industrialized mass production of metal complexes.

[0161] Element Example 4

[0162] The embodiment of Device Example 4 is similar to Device Example 1, except that Compound H3 replaces Compound H2 in the light-emitting layer (EML), and the ratio of Compound H1:Compound H3:Metal Complex 13 in the light-emitting layer is 63:31:6.

[0163] Comparative Example 4 of the Element

[0164] The embodiment of Comparative Example 4 of the device is similar to that of Example 4 of the device, except that the compound GD2 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0165] Comparative Example 5 of the Element

[0166] The embodiment of Comparative Example 5 of the device is similar to that of Example 4 of the device, except that the compound GD4 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0167] Comparative Example 6 of the Element

[0168] The embodiment of Comparative Example 6 of the device is similar to that of Example 4 of the device, except that the compound GD5 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0169] Comparative Example 7 of the Element

[0170] The embodiment of Comparative Example 7 of the device is similar to that of Example 4 of the device, except that the compound GD6 replaces the metal complex 13 according to the present invention in the light-emitting layer (EML).

[0171] The detailed layer structure and thickness of the device are shown in Table 6 below. Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0172] [Table 6]

[0173] The structure of the new material used in the device is represented as follows:

[0174] [ka]

[0175] The IVL characteristics of the element were measured. 2 The CIE data of the element, maximum radiation wavelength λ max The full width at half maximum (FWHM) was measured. The service life (LT95) was measured when the initial luminance was 10,000 cd / m 2 The time required for decay from 0.01 to 95% of the initial value is recorded and displayed in Table 7.

[0176] [Table 7]

[0177] As can be seen from the data in Table 7, 10000cd / m 2The service life of Example 4 reached 1159 hours, which was significantly improved compared to Comparative Examples 4 to 7. a The L b Compared to Comparative Examples 5 and 7, which do not have cyano group substitution in the ligand, the results are improved by approximately 15.8% and 23.3%, respectively. a and L b This is a 27.4% improvement over Comparative Example 6, which does not have any specific substitutions. Furthermore, the full width at half maximum of Example 4 is only 37.5 nm, which is much lower than the approximately 59 nm of Comparative Examples 5 and 7. This is very desirable for green phosphorescent devices.

[0178] L b If the ligand does not have a cyano group substitution, L a Comparative Example 5, where the ligand has a specific substitution, is L a Compared to Comparative Example 6, where the ligand does not have any specific substitution, the service life of the device was improved by 10%. b If the ligand has a cyano group substitution, L a Example 4, where the ligand has a specific substitution, is L a The service life of the device was improved by 39.8% compared to Comparative Example 4, which had no specific substitution in the ligand. a If there is L b Example 4, where the ligand has a cyano group substitution, is L b Compared to Comparative Example 5, which does not have a cyano group substitution in the ligand, the service life of the element is improved by 15.8%. b In Comparative Example 7, in which the ligand was substituted with fluorine, the service life of the element was actually shorter than that of Comparative Example 5. The above results indicate that the specific substitution of L a Ligand and cyano group substitution L b It is shown that metal complexes containing the ligands can obtain superior device performance, especially significantly improved device lifetime.

[0179] In short, L with specific substitutions according to the present invention a and L bThe metal complexes containing the ligands can be used as light-emitting materials in the light-emitting layer of electroluminescent devices, and when used in combination with host materials of different structures, they can all achieve excellent device performance. a and L b The metal complex containing the ligand can significantly improve the service life of the device while maintaining the full width at half maximum of the related device at a high level in the industry. In addition, the metal complex according to the present invention also has a significant improvement in terms of sublimation yield and deposition temperature, and has great advantages and broad prospects in industrial application.

[0180] It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Therefore, it will be apparent to those skilled in the art that the invention sought to be protected includes variations on the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims

1. The metal complex has a structure represented by formula 2: Ir(L a ) 2 L b . 【Chemistry 1】 (Two La are the same or different, Z is selected from O; X ３ ~X ８ is the same or different for each occurrence ｘ Selected from Y １ ~Y ４ is the same or different for each occurrence ｙ Selected from U １ ~U ４ is the same or different for each occurrence ｕ Selected from W １ ~W ４ is the same or different for each occurrence ｗ Selected from R ｙ , R ｕ , R ｗ are each occurrence the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups of 1 to 6 carbon atoms, and combinations thereof; R ｘ are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a cyano group, and combinations thereof; U ２ or U ３ is CR ｕ and wherein R ｕ is a substituted or unsubstituted tertiary alkyl group having 4 to 6 carbon atoms, X ７ is CRx, and the R ｘ is a cyano group, or X ８ is CR ｘ and the R ｘ is a cyano group.

2. At least one of R x in X 3 to X 8 other than the cyano group R x in X 7 or X 8 ｘ is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and combinations thereof.

3. At least one of R x in X 3 to X 8 other than the cyano group R x in X 7 or X 8 ｘ is selected from the group consisting of fluorine, deuterium, a methyl group, a deuterated methyl group, a deuterated isopropyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a methylphenyl group, and a deuterated methylphenyl group.

4. U ２ or U ３ is CR ｕ and wherein R ｕ is substituted or unsubstituted 【Chemistry 2】 and combinations thereof, wherein the hydrogen atoms in the groups may be partially or completely deuterated; The metal complex according to claim 1 , wherein “*” represents a bonding point between the substituent and the carbon.

5. U ２ is CR ｕ and wherein R ｕ is selected from a substituted or unsubstituted tertiary alkyl group having 4 to 6 carbon atoms, or a combination thereof.

6. U １ and U ４ is CR ｕ and R ｕ is selected from hydrogen, deuterium, a methyl group, and a deuterated methyl group.

7. R ｗ and R ｙ 2. The metal complex of claim 1, wherein each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and combinations thereof.

8. L ａ may be the same or different for each occurrence 【Transformation 3】 【change】 【change】 2. The metal complex of claim 1, selected from the group consisting of:

9. L ｂ may be the same or different for each occurrence 【Chemistry 4】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 9. The metal complex of claim 1, wherein the metal complex is selected from the group consisting of:

10. The metal complex is Ir(L ａ ) ２ L ｂ and two L ａ are identical, and L ａ Is, L ａ１ is selected from the group consisting of L a57 to L a96 , L a129 to L a153 , and L a168 to L a174; ｂ Is, L ｂ１ ~L ｂ２ , L ｂ５ ~L ｂ６ , L ｂ９ ~L ｂ１０ , L ｂ１３ ~L ｂ１４ , L ｂ１７ ~L ｂ１８ , L ｂ２１ ~L ｂ２２ , L ｂ２５ ~L ｂ２６ , L ｂ２９ ~L ｂ３０ , L ｂ３３ ~L ｂ３４ , L ｂ３７ ~L ｂ３８ , L ｂ４１ ~L ｂ４２ , L ｂ４５ ~L ｂ４６ , L ｂ４９ ~L ｂ５０ , L ｂ５３ ~L ｂ５４ , L ｂ５７ ~L ｂ５８ , L ｂ６１ ~L ｂ６２ , L ｂ６５ ~L ｂ６６ , L ｂ６９ ~L ｂ１６４ , L ｂ２２１ ~L ｂ３２４ , L ｂ３８１ ~L ｂ４２８ , L ｂ４７７ ~L ｂ４２８ , L ｂ４７７ ~L ｂ５９６ , L ｂ６２３ ~L ｂ８０５ , L ｂ８４１ ~L ｂ８７２ , L ｂ９４９ ~L ｂ９５０ , L ｂ９５３ ~L ｂ９５４ , L ｂ９５７ ~L ｂ９５８ , L ｂ９６１ ~L ｂ９７２ 10. The metal complex of claim 9, selected from the group consisting of:

11. The metal complex is selected from the group consisting of the following metal complexes, and the metal complex is Ir(L ａ ) ２ L ｂ and two L ａ are identical, and L ａ and L ｂ and each correspond to the structure shown in the table below.

12. an anode; A cathode; an organic layer provided between an anode and a cathode, An electroluminescence device, wherein at least one of the organic layers contains the metal complex according to any one of claims 1 to 11.

13. The electroluminescent device according to claim 12 , wherein the organic layer containing the metal complex is a light-emitting layer.

14. 14. The electroluminescent device according to claim 13, wherein the light-emitting layer emits green light.

15. the light-emitting layer further comprises at least one first host compound; 14. The electroluminescent device according to claim 13.

16. 14. The electroluminescent device according to claim 13, wherein the light-emitting layer further comprises at least two host compounds.

17. 17. The electroluminescent device of claim 16, wherein the at least one host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

18. The first host compound has a structure represented by Formula 3, 【Transformation 5】 L ｘ are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; V may be the same or different for each occurrence, and may be C, CR ｖ or N, and at least one of V is C; ｘ is combined with T may be the same or different for each occurrence, and may be C, CR ｔ or N, and at least one of T is C; ｘ is combined with R ｖ and R ｔ are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 2 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 3 ... 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, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar １ are the same or different at each occurrence and are 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; Adjacent substituents R ｖ and R ｔ The electroluminescence device according to claim 15 , wherein may be bonded to form a ring.

19. 14. The electroluminescent device according to claim 13, wherein the metal complex is doped into at least one host compound, and the weight of the metal complex is 1% to 30% based on the total weight of the light-emitting layer.

20. 14. The electroluminescent device according to claim 13, wherein the metal complex is doped into at least one host compound, and the weight of the metal complex is 3% to 13% relative to the total weight of the light-emitting layer.

21. A combination of compounds comprising the metal complex according to any one of claims 1 to 11.

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