Organic electroluminescent materials and their elements

Abstract

To provide an organic electroluminescent material and a device thereof.SOLUTION: There is provided an organic electroluminescent material which is a metal complex containing a La ligand having the structure represented by the formula 1. By introducing a fluorine substituent at a specific position of the La ligand, this novel compound can be applied to an electroluminescent device and can provide more saturated luminescence and better device performance such as improvement in element efficiency and device voltage reduction. There are further provided an electroluminescent device containing a metal complex and a compound containing a metal complex.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to compounds used in organic electronic devices such as organic light-emitting devices. More particularly, to L having a structure represented by formula 1. a This invention relates to a combination of a metal complex containing a ligand, an organic electroluminescent element containing the metal complex, and a compound. [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 electromotive cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect elements (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting elements.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a two-layer organic electroluminescent device containing an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as electron transport and light-emitting layers (Applied Physics Letters, 1987, 51(12):913~915). Once a bias is applied to the device, green light is emitted from it. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may include multiple layers, such as a charge injection / transport layer, a charge / exciton blocking layer, and one or more light-emitting layers between the cathode and anode. Because OLEDs are self-luminous solid-state devices, they offer enormous potential for display and illumination applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for special applications, such as manufacturing on flexible substrates.

[0004] OLEDs are divided into three different types according to their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. The triplet emission generated in the device is wasted through a non-radiative decay path, and this limitation, which limits the internal quantum efficiency (IQE) of fluorescent OLEDs to only 25%, has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs that use triplet emission from complex-containing heavy metals as the emitter. Therefore, it is possible to harvest singlet and triplet emission and achieve 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contribute to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency with thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, which allows for a transition of excitons back from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons through the penetration of triplet excitons between reverse systems (reverse intersystem crossing).

[0005] OLEDs may be further classified into small molecule OLEDs and polymer OLEDs, depending on the form of the material required. Small molecule refers to an organic or organometallic material that is not a polymer, and may have a large molecular weight as long as it has a precise structure. Dendrimers with a clear structure are recognized as small molecules. Polymer OLEDs include conjugated polymers and unconjugated polymers having luminescent groups in the side chains. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can become polymer OLEDs.

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

[0007] The emission color of an OLED can be achieved through the structural design of the light-emitting material. An OLED may contain one or more light-emitting layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized for green, yellow, and red OLEDs, blue phosphorescent elements still have problems such as insufficient blue saturation, short lifespan, and high operating voltage. Commercially available full-color OLED displays generally employ a mixed strategy, using blue fluorescence and yellow, red, or green phosphorescence. Currently, there is a problem in that the efficiency of phosphorescent OLEDs rapidly decreases at high brightness. Furthermore, there is a desire for a more saturated emission spectrum, higher efficiency, and a longer device lifespan.

[0008] Cyano group substitution is not always introduced into phosphorescent metal complexes, such as iridium complexes. The applicant's basic application US20200251666A1 discloses metal complexes having cyano group-substituted ligands, which, when used in organic electroluminescent devices, can improve the performance and color saturation of the devices, reaching a high level in the industry, but still leaving room for improvement. [Prior art documents] [Patent Documents]

[0009] [Patent Document 1] U.S. Patent Application Publication No. 20200251666A1 [Non-patent literature]

[0010] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 [Overview of the Initiative] [Problems that the invention aims to solve]

[0011] To solve at least some of the above-mentioned problems, the present invention provides an L having a structure represented by formula 1. a The objective is to provide a series of metal complexes including ligands. These metal complexes can be used as light-emitting materials in electroluminescent devices. These novel compounds can be applied to electroluminescent devices and can provide better device performance, such as more saturated light emission, improved device efficiency, and reduced device voltage. [Means for solving the problem]

[0012] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal M. a A metal complex containing L a A metal complex having the structure represented by formula 1 is disclosed. [ka] (In Equation 1, metal M is selected from metals with a relative atomic mass greater than 40.) Z is selected from the group consisting of O, S, Se, NR, CRR, and SiRR, and if two Rs exist simultaneously, the two Rs are either identical or different. X1~X8 are either the same or different each time they appear, C, CR x Or selected from N, Y1-Y4 are either the same or different each time they appear in CR y Or selected from N, R, R x , R yis, each time it appears, the same or different and is 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 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 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 of X1 to X8 is CR x and said R x is a cyano group, At least one of Y2 and Y3 is CR y and said R y is F, Adjacent substituents R, R x and R y may be bonded to form a ring.)

[0013] According to another embodiment of the present invention, there is provided an electroluminescence device including an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein at least one layer of the organic layer contains the metal complex described in the above-described embodiment. An electroluminescence device is further disclosed.

[0014] According to another embodiment of the present invention, a combination of compounds containing the metal complex described in the above-described embodiment is further disclosed.

[0015] L having the structure represented by Formula 1 according to the present invention a A series of metal complexes including ligands are L a By introducing fluorine substituents at specific positions on the ligand, these novel compounds can be applied to electroluminescent devices, providing better device performance such as more saturated light emission, improved device efficiency, and reduced device voltage. [Brief explanation of the drawing]

[0016] [Figure 1] This is a schematic diagram of an organic light-emitting device which may include a combination of metal complexes and compounds according to the present invention. [Figure 2] This is a schematic diagram of another organic light-emitting device which may include a combination of metal complexes and compounds according to the present invention. [Modes for carrying out the invention]

[0017] OLEDs can be manufactured on a variety of substrates, including glass, plastic, and metal. Figure 1 shows an organic light-emitting apparatus 100 as an example without limitation. The apparatus is not necessarily manufactured to scale, and some layer structures may be omitted in the figure as necessary. The apparatus 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The apparatus 100 may be manufactured by sequentially depositing the described layers. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Patent US7279704B2, all of which are incorporated herein by reference.

[0018] There are many more examples for each of these layers. Exemplarily, a flexible, transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, incorporated entirely by reference. For example, in U.S. Patent Application Publication No. 2003 / 0230980, incorporated entirely by reference, an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 by Thompson et al., incorporated entirely by reference. For example, in U.S. Patent Application Publication No. 2003 / 0230980, incorporated entirely by reference, an example of an n-type doped electron transport layer is BPhen doped with Li in a 1:1 molar ratio. Examples of cathodes, including composite cathodes having a thin metal layer such as Mg:Ag and a sputter-deposited transparent conductive ITO layer coated thereon, are disclosed in U.S. Patents 5,703,436 and 5,707,745, which are incorporated by full text. The principle and use of blocking layers are described in more detail in U.S. Patents 6,097,147 and U.S. Patent Publication 2003 / 0230980, which are incorporated by full text. Examples of injection layers are provided in U.S. Patent Publication 2004 / 0174116, which is incorporated by full text. Protective layers are described in U.S. Patent Publication 2004 / 0174116, which is incorporated by full text.

[0019] The layered structures described above are provided by non-limiting embodiments. The functions of an OLED can be realized 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 various materials can be used to achieve optimal performance. Any functional layer may include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0020] In one embodiment, the OLED may be described as having an "organic layer" provided between the cathode and the anode. The organic layer may consist of one or more layers.

[0021] An encapsulation layer is also required for OLEDs, and an organic light-emitting device 200 is shown exemplarily and without limitation as shown in Figure 2. The difference from Figure 1 is that an encapsulation layer 102 may be included on the cathode 190 to prevent harmful substances from the outside, such as moisture and oxygen. Any material capable of providing encapsulation functionality, such as glass or an organic-inorganic mixed layer, may be used as the encapsulation layer. The encapsulation layer should be located directly or indirectly outside the OLED element. Multilayer thin-film encapsulation is described in U.S. Patent US7968146B2, the entirety of which is incorporated herein by reference.

[0022] The elements manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the elements. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting lamps and / or signal lamps, head-up displays, all or part transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable elements, smartwatches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and taillights.

[0023] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0024] "Top" refers to the point furthest from the substrate, and "bottom" refers to the point closest to the substrate. When it is stated that the first layer is located "on" the second layer, the first layer is located relatively far from the substrate. Unless it is specified that the first layer "is in contact" with the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, it can still be stated that the cathode is located "on" the anode.

[0025] "A solution is processable" means that it is dissolvable, dispersed, or transportable in a liquid medium in the form of a solution or suspension, and / or can be deposited from a liquid medium.

[0026] It is believed that a ligand that directly enhances the photosensitivity of the propellant material may be called "photosensitive." If a ligand does not enhance the photosensitivity of the propellant material, it may be called "auxiliary." However, it is believed that auxiliary ligands can alter the properties of photosensitive ligands.

[0027] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin statistical limit due to the presence of delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet annihilation (TTA).

[0028] On the other hand, E-type delayed fluorescence relies on the conversion of excited states between triplet and singlet states, rather than on the collision of two triplet states. Compounds capable of producing E-type delayed fluorescence must have an extremely small singlet-triplet gap to facilitate 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 penetration rate between reverse systems (RISCs) is sufficiently fast, non-radiative decay from the triplet state can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlet states may even be 100%, far exceeding the 25% exciton spin statistics due to electro.

[0029] The characteristic of E-type delayed fluorescence is that it can be observed from an excited complex system or a single compound. Not limited to theory, E-type delayed fluorescence is observed when the luminescent material has a small singlet-triplet energy gap (ΔE S-T ) must be present. Organic nonmetal-containing donor-receptor luminescent materials can achieve this. The emission of these materials is typically characterized as donor-receptor charge transition (CT) emission. In these donor-receptor compounds, the spatial separation of HOMO and LUMO is generally small ΔE S-T This will generate the following states. These states may include the CT state. Typically, donor-acceptor luminescent materials are constructed by bonding an electron-donor moiety (e.g., an amino group or carbazole derivative) to an electron-acceptor moiety (e.g., a nitrogen-containing six-membered aromatic ring).

[0030] Definitions of technical terms related to substituents

[0031] Halogens or halides include fluorine, chlorine, bromine, and iodine, as used herein.

[0032] Alkyl groups include linear and branched alkyl groups as used herein. Alkyl groups may have 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexane are preferred. The alkyl group may also be substituted.

[0033] A cycloalkyl group includes a cyclic alkyl group as used herein. The cycloalkyl group may be a cycloalkyl group having 3 to 20 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 group, and 2-norbornyl group. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may also be substituted.

[0034] A heteroalkyl group, as used herein, is defined as an alkyl chain in which one or more carbon atoms are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may have 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl group, ethoxymethyl group, ethoxyethyl group, methylthiomethyl group, ethylthiomethyl group, ethylthioethyl group, methoxymethoxymethyl group, ethoxymethoxymethyl group, ethoxyethoxyethyl group, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, mercaptomethyl group, mercaptoethyl group, mercaptopropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, tert-butyldimethylsilyl group, triethylsilyl group, triisopropylsilicone group, trimethylsilylmethyl group, trimethylsilylethyl group, and trimethylsilylisopropyl group. Furthermore, heteroalkyl groups may be substituted.

[0035] As used herein, an 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 is 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 norbornyl alkenyl groups. Alkenyl groups may also be substituted.

[0036] The alkynyl group, as used herein, includes a linear alkynyl group. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, and is preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3,3-dimethyl-1-butynyl group, 3-ethyl-3-methyl-1-pentynyl group, 3,3-diisopropyl-1-pentynyl group, phenylethynyl group, and phenylpropynyl group. Of these, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, and phenylethynyl group are preferred. The alkynyl group may also be substituted.

[0037] As used herein, aryl groups or aromatic groups refer to non-condensed and condensed 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-condensed 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.

[0038] As used herein, a heterocyclic group or heterocycle refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups with 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups with 3 to 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. 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 oxyranil, oxetanil, tetrahydrofuranil, tetrahydropyranil, dioxopentyl, dioxanil, azilidinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinil, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Furthermore, the heterocyclic groups may be substituted.

[0039] A heteroaryl group, as used herein, may include non-condensed and condensed heteroaromatic groups having 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. An isoaryl group also refers to a heteroaryl group. A heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and more preferably a heteroaryl group having 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, oxathiaidine, oxadiazine, indole, benzimidazole, indazole, indenodine, benzoxazole, benzisoxazole, The formula preferably contains benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, frangipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and seleniumbenzopyridine, and preferably also contains dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and its aza-like compounds. Furthermore, the heteroaryl group may be substituted.

[0040] As used herein, an alkoxy group is represented by an -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group, or -O-heterocyclic group. Examples and preferred examples of alkyl groups, cycloalkyl groups, heteroalkyl groups, and heterocyclic groups are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may also be substituted.

[0041] An aryloxy group is represented as an -O-aryl group or an -O-heteroaryl group as used herein. Examples and preferred examples of aryl and heteroaryl groups 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 aryloxy groups include phenoxy and biphenoxy. The aryloxy group may also be substituted.

[0042] An aralkyl group, as used herein, 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 aralkyl groups are 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-methylbenzyl This includes lolobenzyl, 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. Of 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.

[0043] The alkylsilyl group, as used herein, includes a silyl group substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and 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.

[0044] The arylsilyl group, as used herein, includes 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 preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may also be substituted.

[0045] In azadibenzofuran, azadibenzothiophene, etc., "aza" refers to the substitution of one or more CH groups in the corresponding aromatic fragment with nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogues having two or more nitrogen atoms in the ring system. Those skilled in the art will readily conceive of other nitrogen analogues of the aza derivatives described above, and all of these analogues will be defined as being included in the terminology used herein.

[0046] In the present invention, unless otherwise specified, when using any term from the group consisting of substituted alkyl groups, substituted cycloalkyl groups, substituted heteroalkyl groups, substituted heterocyclic groups, substituted aralkyl groups, substituted alkoxy groups, substituted aryloxy groups, substituted alkenyl groups, substituted alkynyl groups, substituted aryl groups, substituted heteroaryl groups, substituted alkylsilyl groups, substituted arylsilyl groups, substituted amino groups, substituted acyl groups, substituted carbonyl groups, substituted carboxyl groups, substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, and substituted phosphino groups, any one of the groups consisting of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclyl groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups, and phosphino groups is used. , deuterium, halogens, unsubstituted alkyl groups with 1 to 20 carbon atoms, unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, unsubstituted heterocyclic groups with 3 to 20 carbon atoms, unsubstituted aralkyl groups with 7 to 30 carbon atoms, unsubstituted alkoxy groups with 1 to 20 carbon atoms, unsubstituted aryloxy groups with 6 to 30 carbon atoms, unsubstituted alkenyl groups with 2 to 20 carbon atoms, unsubstituted alkynyl groups with 2 to 20 carbon atoms, unsubstituted 6 carbon atoms This means that the group may be substituted with one or more of the following: ~30 aryl groups, unsubstituted heteroaryl groups with 3 to 30 carbon atoms, unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, unsubstituted arylsilyl groups with 6 to 20 carbon atoms, unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

[0047] When describing molecular fragments that are bonded to other parts by substituents or other forms, it should be understood that the name can be determined by whether it is a fragment (e.g., a phenyl group, a phenylene group, a naphthyl group, a dibenzofuranyl group) or a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designation of substituents or different forms of fragment bonding are considered equivalent.

[0048] In the compounds referred to herein, hydrogen atoms may be partially or completely substituted with deuterium. Other atoms, such as carbon and nitrogen, may also be substituted with other stable isotopes of those atoms. Substitution of other stable isotopes in the compounds may be preferable to improve the efficiency and stability of the device.

[0049] In the compounds referred to herein, multiple substitution means a range up to the number of available substitutions, including double substitutions. When a substituent in a compound referred to herein is multiple-substituted (including double, triple, quadruple substitutions, etc.), it means that the substituent may be present at multiple available substitutional positions on its bond structure, and the substituent present at all of the multiple available substitutional positions may have the same structure or different structures.

[0050] Unless otherwise specifically limited to the fact that adjacent substituents may bond to form a ring in the compounds referred to herein, adjacent substituents in such compounds cannot bond to form a ring. The phrase "adjacent substituents may bond to form a ring in the compounds referred to herein" includes not only the case where adjacent substituents may bond to form a ring, but also the case where adjacent substituents do not bond to form a ring. If adjacent substituents may bond to form a ring, the resulting ring may be monocyclic or polycyclic, and may be alicyclic, heteroalicyclic, aryl, or heteroaryl. 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.

[0051] The statement that adjacent substituents may bond to form a ring is understood to mean that two substituents bonded to the same carbon atom are chemically bonded to each other to form a ring, and this can be illustrated by the following formula. [ka]

[0052] The statement that adjacent substituents may bond to form a ring can also be interpreted as meaning that two substituents bonded to carbon atoms directly bonded to each other chemically form a ring, and this can be illustrated by the following formula. [ka]

[0053] Furthermore, the statement that adjacent substituents may bond to form a ring is understood to mean 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 where the hydrogen atom is bonded, thereby forming a ring. This is illustrated in the following formula. [ka]

[0054] According to one embodiment of the present invention, a metal M and a ligand L that coordinates with the metal M. a A metal complex containing L a A metal complex having the structure represented by formula 1 is disclosed. [ka] (In Equation 1, metal M is selected from metals with a relative atomic mass greater than 40.) Z is selected from the group consisting of O, S, Se, NR, CRR, and SiRR, and if two Rs exist simultaneously, the two Rs are either identical or different. X1~X8 are either the same or different each time they appear, C, CR x Or selected from N, Y1-Y4 are either the same or different each time they appear in CR y Or selected from N, R, R x , R yEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, or substituted or unsubstituted aryloxy groups with 2 to 20 carbon atoms. Selected from the group consisting of kenyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, At least one of X1 to X8 is CR x and the R x It is a cyano group, At least one of Y2 and Y3 is CR y and the R y F is, Adjacent substituents R, R x and R y (They may be joined together to form a ring.)

[0055] In this specification, "adjacent substituents R, R x , R y The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R together, or two substituents R together. x The two substituents R y The two substituents R y and R x The two substituents R and R xThis means that one or more of these substituents may be bonded together to form a ring. Clearly, none of these substituents are required to be bonded together to form a ring.

[0056] According to one embodiment of the present invention, L a It has a structure represented by one of the formulas 1a to 1e. [ka] (Z is selected from the group consisting of O, S, Se, NR, CRR and SiRR, and if two Rs exist simultaneously, the two Rs are either the same or different.) In equations 1a and 1c, X3 to X8 are either the same or different each time they appear in CR. x Or selected from N, In formula 1b, X1 and X4-X8 are either the same or different each time they appear in CR. x Or selected from N, In equations 1d and 1e, X1-X2 and X5-X8 are either the same or different each time they appear. x Or selected from N, Y1-Y4 are either the same or different each time they appear in CR y Or selected from N, R, R x , R yEach occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, or substituted or unsubstituted aryloxy groups with 2 to 20 carbon atoms. Selected from the group consisting of kenyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, In equations 1a and 1c, at least one of X3 to X8 is CR x and the R x It is a cyano group, In equation 1b, X1 and at least one of X4 to X8 are CR x and the R x It is a cyano group, In equations 1d and 1e, at least one of X1-X2 and X5-X8 is CR x and the R x It is a cyano group, At least one of Y2 and Y3 is CR y and the R y F is, Adjacent substituents R, R x , R y (They may be joined together to form a ring.)

[0057] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b )n (L c ) q It has the general formula, Metal M is selected from metals with a relative atomic mass greater than 40, preferably M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt, with the same or different selections for each occurrence, and more preferably M is selected from Pt or Ir, with the same or different selections for each occurrence. L a , L b and L c These are the first, second, and third ligands that coordinate with metal M, respectively, and L c and the aforementioned L a or L b This means that they are the same or different, L a , L b and L c These may be combined to form a polydentate ligand, for example, L a , L b and L c Any two of these may be combined to form a tetradentate ligand, and also, for example, L a , L b and L c These may be bonded to each other to form a hexadentate ligand, or, for example, L a , L b , L c None of these necessarily need to combine to form a polydentate ligand. m=1, 2 or 3, n=0, 1 or 2, q=0, 1 or 2, m+n+q is equal to the oxidation state of metal M, and if m is 2 or greater, there are multiple L a If n is 2, then the two L b If they are the same or different, and q is 2, then the two L c They are the same or different. L b and L c Each occurrence may be the same or different [ka] A structure is selected from any one of the groups consisting of the following: R a , Rb and R c represents mono - substitution, multi - substitution, or no substitution, either the same or different for each occurrence, X b represents, either the same or different for each occurrence, O, S, Se, NR N1 , CR C1 R C2 and is selected from the group consisting of R a , R b , R c , R N1 , R C1 and R C2 represents, either the same or different for each occurrence, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 - 20 carbon atoms, a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 - 20 carbon atoms, a substituted or unsubstituted amino group having 0 - 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, and is selected from the group consisting of Adjacent substituents R a , R b , R c , R N1 , R C1 and R C2 may combine to form a ring.

[0058] As used herein, "adjacent substituents R a , R b , R c , R N1 , R C1and R C2 The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a The two substituents R b The two substituents R c Mutual, substituent R a and R b Mutual, substituent R a and R c Mutual, substituent R b and R c Mutual, substituent R a and R N1 Mutual, substituent R b and R N1 Mutual, substituent R a and R C1 Mutual, substituent R a and R C2 Mutual, substituent R b and R C1 Mutual, substituent R b and R C2 Allies, and R C1 and R C2 This means that one or more of these substituents may be bonded together to form a ring. Clearly, none of these substituents are required to be bonded together to form a ring.

[0059] According to one embodiment of the present invention, the metal complex has a structure represented by formula 2. [ka] (m is chosen from 1, 2 or 3, and if m=1, two L b If m=2 or 3, then multiple L a They are the same or different. Z is selected from the group consisting of O, S, Se, NR, CRR, and SiRR, and if two Rs exist simultaneously, the two Rs are either identical or different. X3~X8 are either the same or different each time they appear in CR x Or selected from N, Y1-Y4 are either the same or different each time they appear in CR y Or selected from N, R, R x , R y R1~R8 may be the same or different each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted 2 to 20 carbon atoms Selected from the group consisting of alkenyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, At least one of X3 to X8 is CR x and the R x It is a cyano group, At least one of Y2 and Y3 is CR y and the R y F is, Adjacent substituents R, R x , R y R1 to R8 may be bonded together to form a ring.

[0060] In this embodiment, "adjacent substituents R, R x , R y The phrase "R1~R8 may be bonded together to form a ring" means that adjacent substituent groups, for example, two substituents R1 and two substituents R1 and R2, may be bonded together. x The two substituents R yThis means that any one or more of the substituents from R1 to R8 may bond to each other to form a ring. Clearly, none of these substituents may bond to each other to form a ring.

[0061] According to one embodiment of the present invention, Z is selected from O and S.

[0062] According to one embodiment of the present invention, Z is O.

[0063] According to one embodiment of the present invention, Y1 to Y4 are the same or different each time they appear in CR y Selected from and at least one of Y2 and Y3 is CR y and the R y It is F.

[0064] According to one embodiment of the present invention, Y1 to Y4 are the same or different each time they appear in CR y Or selected from N, and at least one of Y2 and Y3 is CR y and the R y It is F.

[0065] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y It is F, and the others among Y1 to Y4 are CR y If selected from, R y Each occurrence is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof, and is the same or different each time it appears.

[0066] In this specification, "other than Y1 to Y4" refers to the following situation: Y2 is CR y and the R yIf it is F, then "other than Y1-Y4" refers to Y1 and Y3-Y4. If Y3 is CR y and the R y If it is F, then "other than Y1-Y4" refers to Y4 and Y1-Y2. If both Y2 and Y3 are CR y and the R y If the value is F, then "other than Y1 to Y4" refers to Y1 and Y4.

[0067] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y It is F, and the others among Y1 to Y4 are CR y If selected from, R y Each occurrence is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, and combinations thereof, and is the same or different each time it appears.

[0068] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y It is F, and the others among Y1 to Y4 are CR y If selected from, R y The group is selected from hydrogen, deuterium, methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, or a combination thereof, and the hydrogen in the above group may be partially or completely deuterated.

[0069] According to one embodiment of the present invention, at least one of Y2 and Y3 is CR y and the R y F is F, and at least one of Y1 to Y4 is CR y Selected from and at least one R yThe group is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

[0070] According to one embodiment of the present invention, Y2 is CR y and the R y is fluorine, and Y3 is CR y And R y This is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

[0071] According to one embodiment of the present invention, Y3 is CR y and the R y is fluorine, and Y2 is CR y And R y This is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

[0072] According to one embodiment of the present invention, X1 to X8 are identical or different C or CR each time they appear. x They are selected from among them.

[0073] According to one embodiment of the present invention, at least two of X1 to X8 are CR x And the one R x is a cyano group and at least one other R xThis includes deuterium, halogens, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, and substituted or The group is selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

[0074] According to one embodiment of the present invention, at least two of X1 to X8 are CR x And the one R x is a cyano group and at least one other R x The group is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof.

[0075] According to one embodiment of the present invention, at least two of X1 to X8 are CR x And the one R x is a cyano group and at least one other R xThe group is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

[0076] According to one embodiment of the present invention, X7 and X8 are both CR x Selected from and the one R x is a cyano group, and the other one R x The group is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

[0077] According to one embodiment of the present invention, at least one of X5 to X8 is CR x and the R x It is a cyano group.

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

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

[0080] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0081] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

[0082] According to one embodiment of the present invention, at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, and combinations thereof, and some or all of the hydrogen in the above groups may be deuterated.

[0083] According to one embodiment of the present invention, R is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

[0084] According to one embodiment of the present invention, R is a methyl group or a deuterated methyl group.

[0085] According to one embodiment of the present invention, L a Each occurrence is either the same or different L a1 ~La 766 It is selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14.

[0086] According to one embodiment of the present invention, L b Each occurrence is either the same or different L b1 ~L b78 It is selected from the group consisting of L. b1 ~L b78 The specific structure is shown in claim 15.

[0087] According to one embodiment of the present invention, L b Each occurrence is either the same or different Lb1 ~L b80 It is selected from the group consisting of L. b1 ~L b80 The specific structure is shown in claim 15.

[0088] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) has the structure, L a Each occurrence is either the same or different L a1 ~L a766 One or two of the following are selected from the group consisting of L b L b1 ~L b78 It is one of the following selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14, L b1 ~L b78 The specific structure is shown in claim 15.

[0089] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) has the structure, L a Each occurrence is either the same or different L a1 ~L a766 One or two of the following are selected from the group consisting of L b L b1 ~L b80 It is one of the following selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14, L b1 ~L b80 The specific structure is shown in claim 15.

[0090] According to one embodiment of the present invention, the metal complex is Ir(L a )(L b ) has the structure of L a L a1 ~L a766 It is one of the groups consisting of L b Each occurrence is either the same or different L b1~L b78 It is one or two of the following selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14, L b1 ~L b78 The specific structure is shown in claim 15.

[0091] According to one embodiment of the present invention, the metal complex is Ir(L a )(L b ) has the structure of L a L a1 ~L a766 It is one of the groups consisting of L b Each occurrence is either the same or different L b1 ~L b80 It is one or two of the following selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14, L b1 ~L b80 The specific structure is shown in claim 15.

[0092] According to one embodiment of the present invention, the metal complex is Ir(L a ) has a structure of L a Each occurrence is either the same or different L a1 ~L a766 It is one, two, or three of the following selected from the group consisting of L. a1 ~La 766 The specific structure is shown in claim 14.

[0093] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 360. The specific structures of metal complex 1 to metal complex 360 are shown in claim 16.

[0094] According to one embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 390. The specific structures of metal complex 1 to metal complex 390 are shown in claim 16.

[0095] According to one embodiment of the present invention, an electroluminescent element is disclosed comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein at least one layer of the organic layer contains a metal complex as described in any one of the embodiments described above.

[0096] According to one embodiment of the present invention, the organic layer containing the metal complex in the electroluminescent element is a light-emitting layer.

[0097] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element emits green light.

[0098] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element comprises at least one first host compound.

[0099] According to one embodiment of the present invention, the light-emitting layer in the electroluminescent element further comprises at least two host compounds.

[0100] According to one embodiment of the present invention, the at least one host compound in the electroluminescent element contains 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, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0101] According to one embodiment of the present invention, the first host compound in the electroluminescent element has a structure represented by formula 3. [ka] (L xEach occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups with 3 to 20 carbon atoms, substituted or unsubstituted arylene groups with 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 20 carbon atoms, or combinations thereof. V is the same or different each time it appears, C, CR v Or selected from N, and at least one of V is C, L x Combined, U is the same or different each time it appears, C, CR u Or selected from N, and at least one of U is C, L x Combined, R v and R u Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, or substituted or unsubstituted aryloxy groups with 2 to 20 carbon atoms. Selected from the group consisting of kenyl groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Ar1 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or combinations thereof, with each occurrence being identical or different. adjacent substituent R v and R u(They may be joined together to form a ring.)

[0102] In this embodiment, "adjacent substituent R v and R u The phrase "may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v The two substituents R u The two substituents R v and R u This means that one or more of these substituents may be bonded together to form a ring. Clearly, none of these substituents are required to be bonded together to form a ring.

[0103] According to one embodiment of the present invention, the first host compound in the electroluminescent element has a structure represented by one of formulas 3-a to 3-j. [ka]

[0104] According to one embodiment of the present invention, in the electroluminescent element, when a 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.

[0105] According to one embodiment of the present invention, in the electroluminescent element, when a metal complex is doped into the first host compound and the second host compound, the weight of the metal complex is 3% to 13% of the total weight of the light-emitting layer.

[0106] According to other embodiments of the present invention, combinations of compounds containing the metal complex described in any one of the embodiments described above are disclosed.

[0107] Combination with other materials

[0108] The materials of the specific layers used in the organic light-emitting devices described herein can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, and their contents are incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily identify other materials that can be used in combination by referring to the literature.

[0109] In this specification, the materials of specific layers used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. Exemplarily, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080-0101 of patent application US2015 / 0349273A1, and are incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily identify other materials that can be used in combination by referring to the literature.

[0110] In the examples of material synthesis, unless otherwise specified, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used in their commercially available form. The synthesized products were subjected to structural verification and characterization tests in a manner familiar to those skilled in the art, using one or more instruments of the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatograph, a liquid chromatograph / mass spectrometer, a gas chromatograph / mass spectrometer, a differential thermal scanning calorimetry system, a Shanghai Liang Optics Technology fluorescence spectrophotometer, a Wuhan Cosit electrochemical workstation, an Anhui Beik sublimation apparatus, etc.). In the examples of devices, the characteristics of the devices were also tested in a manner familiar to those skilled in the art, using instruments of the art (including, but not limited to, an Angstrom Engineering vapor deposition machine, a Suzhou Fluorida optical test system, a service life test system, a Beijing Liangtuo ellipsometer, etc.). Those skilled in the art are familiar with the use of the equipment, test methods, and other related matters, and can reliably and unaffected obtain sample-specific data; therefore, these related matters will not be repeatedly described in this specification.

[0111] Examples of material synthesis

[0112] The method for preparing the compounds according to the present invention is not limited. Typical but non-limiting examples of the following compounds are given below, along with their synthesis routes and preparation methods.

[0113] Synthesis Example 1: Synthesis of Metal Complex 4 [ka] In a 250 mL dry round-bottom flask, intermediate 1 (2.2 g, 7.2 mmol), iridium complex 1 (3.5 g, 5.2 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added in order. The reaction was heated at 110 °C for 120 h under the protection of N2. After the reaction cooled, the mixture was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, and the mixture was concentrated under reduced pressure. Purification by column chromatography yielded metal complex 4 (0.94 g, 22.4% yield), a yellow solid. This product was identified as the target product with a molecular weight of 805.2.

[0114] Synthesis Example 2: Synthesis of Metal Complex 14 [ka] In a 250 mL dry round-bottom flask, intermediate 2 (1.5 g, 4.9 mmol), iridium complex 1 (2.9 g, 4.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added in order. The reaction was heated at 90 °C for 144 hours under the protection of N2. After the reaction cooled, the solution was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, and the solution was concentrated under reduced pressure. Purification by column chromatography yielded metal complex 14 (0.70 g, 21.8% yield), a yellow solid. The structure of the product was confirmed to be the target product with a molecular weight of 805.2.

[0115] Synthesis Example 3: Synthesis of Metal Complex 44 [ka] In a 250 mL dry round-bottom flask, intermediate 2 (1.6 g, 5.2 mmol), iridium complex 2 (3.1 g, 4.0 mmol), 2-ethoxyethanol (25 mL), and DMF (25 mL) were added in order. The reaction was carried out at 90 °C for 144 hours under the protection of N2. After the reaction cooled, the mixture was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved with dichloromethane, the organic phase was collected, and the mixture was concentrated under reduced pressure. Purification by column chromatography yielded metal complex 44 (0.58 g, 17.5% yield), a yellow solid. The structure of the product was confirmed to be the target product with a molecular weight of 833.2.

[0116] Synthesis Example 4: Synthesis of Metal Complex 103 [ka] In a 250 mL dry round-bottom flask, intermediate 3 (1.2 g, 3.9 mmol), iridium complex 3 (2.5 g, 3.2 mmol), 2-ethoxyethanol (20 mL), and DMF (20 mL) were added in order. The reaction was heated at 90 °C for 144 h under the protection of N2. After the reaction cooled, the solution was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved with dichloromethane, the organic phase was collected, and the solution was concentrated under reduced pressure. Purification by column chromatography yielded metal complex 103 (0.85 g, 30.9% yield), a yellow solid. The structure of the product was confirmed to be the target product with a molecular weight of 861.2.

[0117] Synthesis Example 5: Synthesis of Metal Complex 389 [ka] In a 250 mL dry round-bottom flask, intermediate 4 (1.6 g, 4.2 mmol), iridium complex 4 (2.6 g, 3.2 mmol), 2-ethoxyethanol (25 mL), and DMF (25 mL) were added in order. The reaction was heated at 90 °C for 144 h under the protection of N2. After the reaction cooled, the solution was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane. The yellow solid on the diatomaceous earth was dissolved in dichloromethane, the organic phase was collected, and the solution was concentrated under reduced pressure. Purification by column chromatography yielded metal complex 389 (0.48 g, 15.1% yield), a yellow solid. The structure of the product was confirmed to be the target product with a molecular weight of 993.3.

[0118] Those skilled in the art should know that the above preparation method is merely illustrative, and that the structures of other compounds of the present invention can be obtained by improving it.

[0119] Element Example 1

[0120] 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. Then, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Subsequently, the specified organic layer was subjected to a vacuum of approximately 10°C. -8In the case of Toll, deposition was carried out sequentially on the ITO anode by hot vacuum deposition at a speed of 0.2 to 2 angstroms / second. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound H1 was used as the electron blocking layer (EBL). Subsequently, the metal complex 4 of the present invention was doped into compounds H1 and H2 and used as the light-emitting layer (EML). On the EML, compound H3 was used as the hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm was deposited as the electron injection layer, and 120 nm of aluminum was deposited as the cathode. The device was then transferred to a glove box and encapsulated using a glass cover and a desiccant to complete the device.

[0121] Element Example 2

[0122] The embodiment of the device in embodiment 2 is the same as that of the device in embodiment 1, except that the metal complex 4 according to the present invention is replaced with the metal complex 14 according to the present invention in the light-emitting layer (EML).

[0123] Element Example 3

[0124] The embodiment of the third example of the device is the same as that of the first example of the device, except that the metal complex 4 according to the present invention is replaced with the metal complex 4 according to the present invention in the light-emitting layer (EML).

[0125] Element Example 4

[0126] The embodiment of the fourth example of the device is the same as that of the first example of the device, except that the metal complex 4 according to the present invention is replaced with the metal complex 389 according to the present invention in the light-emitting layer (EML).

[0127] Comparative Example 1 of the Element

[0128] The embodiment of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that the metal complex 4 according to the present invention is replaced with compound GD1 in the light-emitting layer (EML).

[0129] Comparative Example 2 of the Element

[0130] The embodiment of Comparative Example 2 of the device is the same as that of Example 1 of the device, except that the metal complex 4 according to the present invention is replaced with compound GD2 in the light-emitting layer (EML).

[0131] Comparative Example 3 of the Element

[0132] The embodiment of Comparative Example 3 of the device is the same as that of Example 1 of the device, except that the metal complex 4 according to the present invention is replaced with compound GD3 in the light-emitting layer (EML).

[0133] The detailed layer structure and thickness of the element are shown in Table 1 below. Layers using more than one type of material are obtained by doping with different compounds in the aforementioned weight ratio.

[0134] [Table 1]

[0135] The structure of the material used in the element is represented as follows: [ka] TIFF0007843510000018.tif43168

[0136] The IVL characteristics of the element were measured. 1000 cd / m² 2 So, the CIE data for the element, maximum emission wavelength λ max The full width at half maximum (FWHM), voltage (V), and external quantum efficiency (EQE) were measured. These data are recorded and presented in Table 2.

[0137] [Table 2]

[0138] summary

[0139] Table 2 shows the performance of the elements in the examples and comparative examples. As can be seen from the data in Table 2, L a Compared to Comparative Example 1, which had no ligand substitution, Examples 1 and 2 exhibited a 4-5 nm blue shift in emission wavelength and more saturated green emission. Furthermore, Examples 1 and 2 achieved element EQE of 24.37% and 24.65%, respectively, both higher than Comparative Example 1's 23.39%, representing an improvement over Comparative Example 1, which was already at a high level in the industry. In addition, the element voltage of Examples 1 and 2 was approximately 0.35 V lower than that of Comparative Example 1.

[0140] L a The spectra of Comparative Example 3, in which deuterated methyl groups are substituted at the Y2 and Y3 positions of the ligand, are similar to those of Examples 1 and 2. However, the EQE of Comparative Example 3 is lower to a different degree than that of Examples 1 and 2, and the device voltage is also higher than that of Examples 1 and 2.

[0141] L a Comparative Example 2, which has a fluorine substitution at the Y1 position of the ligand, exhibits a maximum emission wavelength redshift of approximately 20 nm and a full width at half maximum that is 18.5 nm and 23.9 nm wider, respectively, compared to Examples 1 and 2, indicating that the emission color of Comparative Example 2 is unsaturated. Furthermore, Comparative Example 2 shows a certain degree of EQE reduction and a slightly higher device voltage compared to Examples 1 and 2.

[0142] As can be seen from the above results, the metal complex having an F-substituted ligand at a specific position according to the present invention is L a For metal complexes where the ligand is either unsubstituted at the same position, substituted with another alkyl group, or fluorine substituted at another position, the device performance improved, particularly with a decrease in device voltage, an improvement in EQE, and an improvement in the saturation of the luminescent color.

[0143] Examples 3 and 4 showed significant improvements over Comparative Examples 1-3, exhibiting higher EQE and lower drive voltages. The drive voltage of Example 3 was 0.5V, 0.22V, and 0.21V lower than that of Comparative Examples 1-3, respectively. Example 4, using the metal complex according to the present invention, achieved an EQE of 26.52%, an improvement of approximately 13.4%, 15.2%, and 14.6% compared to Comparative Examples 1-3, respectively. Simultaneously, the full width at half maximum of Example 4 was extremely narrow, at only 32.3 nm, which is at a very high level in the industry.

[0144] As can be seen from the above results, the metal complex having a fluorine substitution ligand at a specific position according to the present invention shows improved device performance compared to metal complexes with fluorine substitution at other positions of the ligand. In particular, the luminescence color saturation is improved, the full width at half maximum is narrowed, the EQE is improved, and the voltage is reduced.

[0145] It should be understood that the various embodiments described herein are illustrative only and not intended to limit the scope of the invention. Therefore, it will be obvious to those skilled in the art that the invention to be protected includes variations of the specific and preferred embodiments described herein. Without departing from the concept of the invention, many of the materials and structures described herein can be substituted with other materials and structures. It should be understood that the various theories regarding why the invention works are not limiting.

Claims

1. An organic layer comprising a metal complex having the general formula Ir(La)m(Lb)n, L a and L b are the first and second ligands that coordinate with metal Ir, respectively, where m = 1 or 2, n = 1 or 2, and m + n is equal to the oxidation state of metal Ir. When m is 2 or greater, multiple L a are the same or different, and when n is 2, the two L b are the same or different. ａ It has a structure represented by formula 1a, 【Chemistry 1】 (In formula 1a, Z was chosen from O, X3 to X ８ Each appearance is either the same or different CR ｘ Or selected from N, Y １ ~Y ４ Each appearance is either the same or different CR ｙ Or selected from N, R ｘ , R ｙ Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, isocyano groups, and combinations thereof, and is the same or different each time it appears. X7 is CRx and Rx is a cyano group, or X8 is CRx and Rx is a cyano group, Y ２ and Y ３ At least one of them is CR ｙ and the said R ｙ is F.) Lb is an organic layer selected from the following structures. 【Chemistry 2】 (However, R a and R b are identical or different each time they appear, representing one substitution, multiple substitutions, or no substitution.) R a and R b are selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, isocyano groups, and combinations thereof, each time they appear, either identically or differently.

2. R ａ The organic layer according to claim 1, wherein Rb is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof, with each occurrence being the same or different.

3. The organic layer according to claim 1, wherein the metal complex has a structure represented by formula 2. 【Transformation 3】 (m=1, two L ｂ They are the same or different. Z was chosen from O, X ３ ~X ８ Each occurrence is selected from CRx, either identically or differently. Y １ ~Y ４ Each occurrence is selected from CRy, either identically or differently. R ｘ , R ｙ , R １ ~R ８ Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof, and is the same or different each time it appears. X7 is CRx and Rx is a cyano group, or X8 is CRx and Rx is a cyano group, Y ２ and Y ３ At least one of them is CR ｙ and R ｙ (This is F.)

4. Y １ ~Y ４ Each appearance is either the same or different CR ｙ Selected from and Y ２ and Y ３ At least one of them is CR ｙ and R ｙ The organic layer according to claim 1, wherein F is present.

5. Y ２ and Y ３ At least one of them is CR ｙ and R ｙ F is Y １ ~Y ４ The others are CR ｙ If selected from, R ｙ The organic layer according to claim 1 or 3, wherein each occurrence is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof, either identical or different each time they appear.

6. The organic layer according to claim 1 or 3, wherein at least one of Y2 and Y3 is CRy, and Ry is F, and the others of Y1 to Y4 are selected from CRy, and Ry is selected from hydrogen, deuterium, methyl group, propyl group, isopropyl group, butyl group, tert-butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, or a combination thereof, and the hydrogen in the above groups may be partially or completely deuterated.

7. Y ２ and Y ３ At least one of them is CR ｙ and R ｙ F is Y １ ~Y ４ At least one of them is CR ｙ Selected from and at least one R ｙ The organic layer according to claim 1 or 3, wherein is selected from the group consisting of deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

8. Y ２ CR ｙ and R ｙ Fluorine is Y ３ CR ｙ and R ｙ This is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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. Alternatively, Y ３ CR ｙ and R ｙ Fluorine is Y ２ CR ｙ , and the R ｙ The organic layer according to claim 1 or 3, wherein is selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, 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.

9. X3 to X ８ Each appearance is either the same or different CR ｘ The organic layer according to claim 1, selected from the above.

10. X3 to X ８ At least two of them are CR ｘ And here, the one R ｘ is a cyano group, and other R groups other than cyano groups ｘ The organic layer according to claim 1, wherein is selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, isocyano groups, and combinations thereof.

11. The organic layer according to claim 10, wherein at least two of X3 to X8 are CRx, where one Rx is a cyano group, and at least one other Rx is selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted ring C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C15 aryl groups, substituted or unsubstituted C3-C15 heteroaryl groups, and combinations thereof.

12. R ２ , R ３ , R ６ , R ７ The organic layer according to claim 3, wherein at least one, at least two, at least three, or all of the members are selected from the group consisting of deuterium, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted ring C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and combinations thereof.

13. The organic layer according to claim 12, wherein at least one, at least two, at least three, or all of R2, R3, R6, and R7 are selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, and combinations thereof, and the hydrogen in the above groups may be partially or entirely deuterated.

14. L ａ Each occurrence may be the same or different. 【Chemistry 4-1】 【Chemistry 4-2】 【Chemistry 4-3】 【Chemistry 4-4】 [Chemistry 4-5] [Chemistry 4-6] 【Chemistry 4-7】 【Chemistry 4-8】 【Chemistry 4-9】 【Chemistry 4-10】 【Chemistry 4-11】 【Chemistry 4-12】 【Chemistry 4-13】 【Chemistry 4-14】 【Chemistry 4-15】 【Chemistry 4-16】 【Chemistry 4-17】 【Chemistry 4-18】 【Chemistry 4-19】 【Chemistry 4-20】 【Chemistry 4-21】 【Chemistry 4-22】 The organic layer according to claim 1, which is one selected from the group consisting of the following.

15. L ｂ Each occurrence may be the same or different. 【Chemistry 5-1】 【Chemistry 5-2】 【Chemistry 5-3】 The organic layer according to claim 14, selected from the group consisting of the following.

16. The aforementioned metal complex is Ir(L ａ ) ２ (L ｂ ) or Ir(L ａ ) (L ｂ ) It has the structure of L ａ Each appearance is either the same or different L ａ１ , L a2 , L a5 , L a6 , L a9 , L a10 , L a13 , L a14 , L a17 , L a18 , L a21 , L a22 , L a25 , L a26 , L a29 , L a30 , L a33 , L a34 , L a37 , L a38 , L a41 , L a42 , L a45 , L a46 , L a49 , L a50 , L a53 , L a54 , L a57 , L a58 , L a61 , L a62 , L a65 , L a66 , L a69, L a70, L a73 , La74 , La77 , La78 , La81 , La82 , La85 , La86 , La89 , La90 , La93 , La94 , La97 , La98 , La101 , La102 , L a105 , L a106 , L a109 , L a110 , L a113 to L a288 , L a381 to L a556 , L a711 , L a712 , L a715 , L a716 , L a719 , L a720 , L a723 , L a724, L a727 L a728, L a731, L a732, L a735, L a736, L a739, L a740, L a743, L a744, L a747, L a748, L a751, L a752, L a755 and L a756 are selected from the group, one or two of which are L ｂ is, L ｂ１ ~L ｂ８０ The organic layer according to claim 15, which is one or two selected from the group consisting of the following.

17. The metal complex consists of metal complex 1 to metal complex 24, metal complex 26 to metal complex 54, metal complex 56 to metal complex 84, metal complex 86 to metal complex 114, metal complex 116 to metal complex 144, metal complex 146 to metal complex 174, metal complex 176 to metal complex 204, metal complex 206 to metal complex 234, metal complex 236 to metal complex 264, metal complex 266 to metal complex 294, metal complex 296 to metal complex 324, metal complex 326 to metal complex 354, metal complex 356 to metal complex 384, and metal complex 386 to metal complex 390. Selected from the group, metal complexes 1 to 24, 26 to 54, 56 to 84, 86 to 114, 116 to 144, 146 to 174, 176 to 204, 206 to 234, 236 to 264, 266 to 294, 296 to 324, 326 to 354, 356 to 384, and 386 to 390 have the structure IrLa(Lb)2, where the two Lb are identical, and La and Lb correspond to the structures shown in the table below, respectively, according to claim 16. Table 1 Table 2 Table 3 Table 4 Table 5

18. Anode and, Cathode and, An electronic component module comprising an electroluminescent element comprising an organic layer according to any one of claims 1 to 17 provided between an anode and a cathode.

19. The electronic component module according to claim 18, wherein the organic layer is a light-emitting layer.

20. The electronic component module according to claim 19, wherein the light-emitting layer emits green light.

21. The electronic component module according to claim 19, wherein the light-emitting layer comprises at least one first host compound.

22. The electronic component module according to claim 21, wherein the light-emitting layer further comprises at least two host compounds.

23. The electronic component module according to claim 22, wherein at least one of the host compounds 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, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

24. The first host compound has a structure represented by formula 3, 【Transformation 6】 L ｘ Each occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof. V is the same or different each time it appears as C, CR ｖ Or selected from N, and at least one of V is C, L ｘ Combined, U is the same or different each time it appears as C, CR ｕ Or selected from N, and at least one of U is C, L ｘ Combined, R ｖ and R ｕ are each independently 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 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 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 Each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof, and is identical or different each time it appears. Adjacent substituent R ｖ and R ｕ The electronic component module according to claim 21, wherein the components may be joined together to form a ring.

25. A display comprising the organic layer described in claim 1 or the electronic component module described in claim 18.

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