CN114524850A - Organic electroluminescent material and device thereof - Google Patents

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material comprises L with a structure of formula 1_aMetal complexes of ligands by reaction at L_aFluorine substituents are introduced into specific positions of the ligands, and the novel compounds can provide more saturated luminescence and better device performance when being applied to electroluminescent devices, such as improvement of device efficiency and reduction of device voltage. Also disclosed are an electroluminescent device comprising the metal complex and a compound composition comprising the metal complex.

Description

Organic electroluminescent material and device thereof

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a composition comprising L having the structure of formula 1_aMetal complexes of ligands, and organic electroluminescent devices and compound combinations comprising the metal complexes.

Background

Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.

In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.

OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.

Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.

The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

Cyano substitution is not often introduced into phosphorescent metal complexes, such as iridium complexes. The application US20200251666a1, which was filed earlier by the applicant of the present application, discloses metal complexes with cyano-substituted ligands, which can be applied to organic electroluminescent devices to improve device performance and color saturation, although reaching the higher level in the industry, there is still room for improvement.

Disclosure of Invention

The present invention aims to provide a series of L containing structures having formula 1_aMetal complexes of ligands to solve at least part of the above problems. The metal complexes can be used as light-emitting materials in electroluminescent devices. The novel compounds can be applied to electroluminescent devices to provide more saturated luminescence and better device performance, such as improvement of device efficiency and reduction of device voltage.

According to one embodiment of the present invention, a metal complex comprising a metal M, and a ligand L coordinated to the metal M is disclosed_aWherein L is_aHas a structure represented by formula 1:

in the formula 1, the first and second groups,

the metal M is selected from metals having a relative atomic mass greater than 40;

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₁-X₈selected from C, CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_yeach occurrence, the same or different, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

X₁-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_xAnd R_yCan optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device, including:

an anode, a cathode, an anode and a cathode,

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of the previous embodiments.

According to another embodiment of the present invention, a combination of compounds is also disclosed, comprising the metal complex of the preceding embodiments.

The invention discloses a series of L containing structures with formula 1_aMetal complexation of ligandsThrough the reaction of L_aFluorine substituents are introduced into specific positions of the ligands, and the novel compounds can provide more saturated luminescence and better device performance when being applied to electroluminescent devices, such as improvement of device efficiency and reduction of device voltage.

Drawings

FIG. 1 is a schematic representation of an organic light emitting device that can contain the metal complexes and compound combinations disclosed herein.

FIG. 2 is a schematic representation of another organic light emitting device that may contain combinations of the metal complexes and compounds disclosed herein.

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. patent No. incorporated by reference in its entiretyExamples of cathodes are disclosed in U.S. Pat. Nos. 5,703,436 and 5,707,745, which include composite cathodes having a thin layer of a metal, such as Mg: Ag, with an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.

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

The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, which is incorporated herein by reference in its entirety.

Devices 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 device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.

The materials and structures described herein may also be used in other organic electronic devices as previously listed.

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

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

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

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.

The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)_S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ E_S-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).

Definitions for substituent terms

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

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

Cycloalkyl-as used herein, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl are preferable. In addition, the cycloalkyl group may be optionally substituted.

Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons 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 be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. In addition, heteroalkyl groups may be optionally substituted.

Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 3-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight chain alkynyl groups are contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Of the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl. In addition, alkynyl groups may be optionally substituted.

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, 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,

perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, 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, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzoselenophenepyridyl, selenophene bipyridine, selenobenzodipyridine, selenium benzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.

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

Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of the 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, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.

Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. In addition, the aralkyl group may be optionally substituted.

Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.

Arylsilyl-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, diphenyltert-butylsilyl group, tri-tert-butylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.

The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.

In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.

In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.

In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, 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 away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.

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

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

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

according to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal M_aWherein L is_aHas a structure represented by formula 1:

in the formula 1, the first and second groups,

the metal M is selected from metals having a relative atomic mass greater than 40;

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₁-X₈selected from C, CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_yeach occurrence, the same or different, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

X₁-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_xAnd R_yCan optionally be linked to form a ring.

As used herein, the "adjacent substituents R, R_x，R_yCan optionally be linked to form a ring ", is intended to denote a group in which adjacent substituents are present, for example, between two substituents R, two substituents R_xIn between, two substituents R_yIn between, two substituents R_yAnd R_xIn between, two substituents R and R_xAnd any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

According to an embodiment of the invention, wherein L_aHas a structure represented by one of formulas 1a-1 e:

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

in the formulae 1a and 1c, X₃-X₈Selected from CR, identically or differently at each occurrence_xOr N;

in formula 1b, X₁And X₄-X₈Selected from CR, identically or differently at each occurrence_xOr N;

in formula 1d and formula 1e, X₁-X₂And X₅-X₈Selected from CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_yeach occurrence, the same or different, 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, substituted or unsubstituted arylsilane groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

in formula 1a, X₃-X₈At least one of which isCR_xAnd said R is_xIs cyano;

in formula 1b, X₁And X₄-X₈At least one of which is CR_xAnd said R is_xIs cyano;

in the formulae 1c and 1d, X₁-X₂And X₅-X₈At least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_x，R_yCan optionally be linked to form a ring.

According to one embodiment of the invention, wherein the metal complex has M (L)_a)_m(L_b)_n(L_c)_qA general formula (II) of (I);

wherein the content of the first and second substances,

the metal M is selected from metals having a relative atomic mass greater than 40; preferably, M is selected, identically or differently on each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;

L_a、L_band L_cAre respectively a first, a second and a third ligand coordinated to the metal M, and L_cAnd said L_aOr L_bAre the same or different; wherein L is_a、L_bAnd L_cOptionally linked to form a multidentate ligand; for example, L_a、L_bAnd L_cAny two of which can be linked to form a tetradentate ligand; also for example, L_a、L_bAnd L_cCan be connected with each other to form a hexadentate ligand; or also for example L_a、L_b、L_cAre not linked so as not to form a multidentate ligand;

m1, 2 or 3, n 0, 1 or 2, q 0, 1 or 2, M + n + q being equal to the oxidation state of the metal M; when m is 2 or more, a plurality of L_aThe same or different; when n is equal to 2, two L_bThe same or different; when q is equal to 2, two L_cThe same or different;

L_band L_cA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:

wherein the content of the first and second substances,

R_a，R_band R_cThe same or different at each occurrence represents mono-, poly-, or no substitution;

X_beach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NR_N1，CR_C1R_C2；

R_a，R_b，R_c，R_N1，R_C1And R_C2Each occurrence, the same or different, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R_a，R_b，R_c，R_N1，R_C1And R_C2Can optionally be linked to form a ring.

As used herein, the "adjacent substituent R_a，R_b，R_c，R_N1，R_C1And R_C2Can optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents R_aIn between, two substituents R_bIn between, two substituents R_cOf a substituent R_aAnd R_bOf a substituent R_aAnd R_cOf a substituent R_bAnd R_cOf a substituent R_aAnd R_N1Of a substituent R_bAnd R_N1Of a substituent R_aAnd R_C1Of R is a substituent_aAnd R_C2Of a substituent R_bAnd R_C1Of a substituent R_bAnd R_C2And R is_C1And R_C2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

According to one embodiment of the present invention, wherein the metal complex has a structure represented by formula 2:

wherein the content of the first and second substances,

m is selected from 1,2 or 3; when m is 1, two L_bThe same or different; when m is 2 or 3, a plurality of L_aThe same or different;

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₃-X₈selected from CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_y，R₁-R₈each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or notA substituted 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 amine group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

X₃-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_x，R_y，R₁-R₈Can optionally be linked to form a ring.

In this example, the "adjacent substituents R, R_x，R_y，R₁-R₈Can optionally be linked to form a ring ", is intended to denote a group in which adjacent substituents are present, for example, between two substituents R, two substituents R_xIn between, two substituents R_yR is₁-R₈In the above formula (b), any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

According to one embodiment of the invention, wherein Z is selected from O and S.

According to one embodiment of the invention, wherein Z is O.

According to one embodiment of the inventionWherein Y is₁-Y₄Selected from CR, identically or differently at each occurrence_yAnd Y is₂And Y₃At least one of which is CR_yAnd said R is_yIs F.

According to an embodiment of the invention, wherein Y₁-Y₄Selected from CR, identically or differently at each occurrence_yOr N, and Y₂And Y₃At least one of which is CR_yAnd said R is_yIs F.

According to one embodiment of the present invention, wherein Y₂And Y₃At least one of which is CR_yAnd said R is_yIs F; y is₁-Y₄The others of (A) and (B) are selected from CR_yWhen R is_yEach occurrence, the same or different, 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 ring 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.

As used herein, "Y" or "Y" is defined as₁-Y₄The remainder of (1) refers to the following: when Y is₂Is CR_yAnd said R is_yWhen is F, "Y₁-Y₄The rest of (1) are Y₁And Y₃-Y₄(ii) a When Y is₃Is CR_yAnd said R is_yWhen is F, "Y₁-Y₄In the rest of R_y"then refers to Y₄And Y₁-Y₂(ii) a When Y is₂And Y₃Are all CR_yAnd said R is_yWhen is F, "Y₁-Y₄In the rest of R_y"then refers to Y₁And Y₄。

According to one embodiment of the present invention, wherein Y₂And Y₃At least one of which is CR_yAnd said R is_yIs F; y is₁-Y₄The others of (A) and (B) are selected from CR_yWhen R is_yEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted compounds having 1 to 20 carbon atomsSubstituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.

According to an embodiment of the invention, wherein Y₂And Y₃At least one of which is CR_yAnd said R is_yIs F; y is₁-Y₄The others of (A) and (B) are selected from CR_yWhen R is_ySelected from hydrogen, deuterium, methyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, tert-pentyl, or combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.

According to an embodiment of the invention, wherein Y₂And Y₃At least one of which is CR_yAnd said R is_yIs F; y is₁-Y₄At least one further one of (A) is selected from CR_yAnd at least one R_yIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring 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.

According to an embodiment of the invention, wherein Y₂Is CR_yAnd said R is_yIs fluorine; y is₃Is CR_y，R_ySelected 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 ring 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.

According to an embodiment of the invention, wherein Y₃Is CR_yAnd said R is_yIs fluorine; y is₂Is CR_y，R_ySelected from the group consisting of: deuterium, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and groups thereofAnd (6) mixing.

According to an embodiment of the invention, wherein X₁-X₈Selected from C or CR, identically or differently at each occurrence_x。

According to an embodiment of the invention, wherein X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino groups having from 0 to 20 carbon atoms, and combinations thereof.

According to an embodiment of the invention, wherein X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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, mercapto groups, and combinations thereof.

According to an embodiment of the invention, wherein X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring 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.

According to an embodiment of the invention, wherein X₇And X₈All are selected from CR_xAnd said one R_xIs cyano, another one of said R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring 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.

According to an embodiment of the invention, wherein X₅-X₈In (1), at least one is CR_xAnd said R is_xIs cyano.

According to an embodiment of the invention, wherein X₇Is CR_xAnd said R is_xIs cyano.

According to an embodiment of the invention, wherein X₈Is CR_xAnd said R is_xIs cyano.

According to one embodiment of the invention, wherein R₂，R₃，R₆，R₇At least one or at least two or at least three or all 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, 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.

According to one embodiment of the invention, wherein R₂，R₃，R₆，R₇At least one or at least two or at least three or all 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.

According to one embodiment of the invention, wherein R₂，R₃，R₆，R₇At least one or at least two or at least three or all selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.

According to one embodiment of the invention, wherein 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.

According to one embodiment of the invention, wherein R is methyl or deuterated methyl.

According to an embodiment of the invention, wherein L_aEach occurrence being selected identically or differently from L_a1-La₇₆₆Group of wherein L_a1-La₇₆₆The specific structure of (a) is as defined in claim 14.

According to an embodiment of the invention, wherein L_bEach occurrence being selected identically or differently from L_b1-L_b78Group of wherein L_b1-L_b78The specific structure of (A) is as defined in claim 15.

According to an embodiment of the invention, wherein L_bEach occurrence being selected identically or differently from L_b1-L_b80Group of wherein L_b1-L_b80The concrete structure of (3) is as described in claim 15.

According to one embodiment of the invention, wherein the metal complex has Ir (L)_a)₂(L_b) Structure of (1), L_aEach occurrence, identically or differently, of a group selected from L_a1To L_a766Any one or any two of the group consisting of,L_bis selected from the group consisting of L_b1To L_b78Any one of the group consisting of wherein L_a1-La₇₆₆According to claim 14, L_b1-L_b78The concrete structure of (3) is as described in claim 15.

According to one embodiment of the invention, wherein the metal complex has Ir (L)_a)₂(L_b) Structure of (1), L_aEach occurrence being selected identically or differently from L_a1To L_a766Any one or any two of the group consisting of, L_bIs selected from the group consisting of L_b1To L_b80Any one of the group consisting of wherein L_a1-La₇₆₆According to claim 14, L_b1-L_b80The specific structure of (A) is as defined in claim 15.

According to one embodiment of the invention, wherein the metal complex has Ir (L)_a)(L_b)₂Structure of (1), L_aIs selected from the group consisting of L_a1To L_a766Any one of the group consisting of L_bEach occurrence being selected identically or differently from L_b1To L_b78Any one or any two of the group consisting of, wherein L_a1-La₇₆₆According to claim 14, L_b1-L_b78The specific structure of (A) is as defined in claim 15.

According to one embodiment of the invention, the metal complex has Ir (L)_a)(L_b)₂Structure of (1), L_aIs selected from the group consisting of L_a1To L_a766Any one of the group consisting of L_bEach occurrence being selected identically or differently from L_b1To L_b80Any one or any two of the group consisting of, wherein L_a1-La₇₆₆According to claim 14, L_b1-L_b80The specific structure of (A) is as defined in claim 15.

According to one embodiment of the invention, wherein the metal complex has Ir (L)_a)₃Structure of (1), L_aEach occurrence, identically or differently, of a group selected from L_a1To L_a766Any of the groupOne or any two or any three, wherein L_a1-La₇₆₆The specific structure of (a) is as defined in claim 14.

According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 360, wherein the specific structures of metal complex 1 to metal complex 360 are described in claim 16.

According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 390, wherein the specific structures of metal complex 1 to metal complex 390 are as defined in claim 16.

According to one embodiment of the present invention, there is disclosed an electroluminescent device, including:

an anode, a cathode, a anode and a cathode,

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising a metal complex according to any of the preceding embodiments.

According to an embodiment of the present invention, wherein the organic layer including the metal complex in the electroluminescent device is a light-emitting layer.

According to an embodiment of the invention, wherein said light emitting layer of said electroluminescent device is emitting green light.

According to one embodiment of the present invention, wherein at least one first host compound is comprised in the light emitting layer of the electroluminescent device.

According to one embodiment of the present invention, wherein the light emitting layer of the electroluminescent device further comprises at least two host compounds.

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

According to an embodiment of the present invention, wherein the first host compound in the electroluminescent device has a structure represented by formula 3:

wherein the content of the first and second substances,

L_xeach occurrence identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

v is selected, identically or differently on each occurrence, from C, CR_vOr N, and at least one of V is C, and with L_xConnecting;

u is selected, identically or differently on each occurrence, from C, CR_uOr N, and at least one of U is C, and with L_xConnecting;

R_vand R_uEach occurrence, identically or differently, 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, 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, carboxylic acid groups,an ester group, a cyano group, an isocyano group, a hydroxy group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Ar₁each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

adjacent substituents R_vAnd R_uCan optionally be linked to form a ring.

In this embodiment, the "adjacent substituents R_vAnd R_uCan optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents R_vIn between, two substituents R_uIn between, two substituents R_vAnd R_uAnd any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

According to one embodiment of the present invention, wherein the second host compound in the electroluminescent device has a structure represented by formula 3-a to

A structure represented by one of formulas 3-j:

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

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

According to another embodiment of the present invention, a combination of compounds is disclosed, the combination of compounds comprising a metal complex according to any one of the preceding embodiments.

In combination with other materials

The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0161 (paragraph 0132-0161) of US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.

Materials synthesis example:

the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:

synthesis example 1: synthesis of Metal Complex 4

A dry 250mL round bottom flask was charged with intermediate 1(2.2g, 7.2mmol), iridium complex 1(3.5g, 5.2mmol), 2-ethoxyethanol (30mL) and DMF (30mL), N in that order₂Heating to react for 120h at 110 ℃ under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 4(0.94g, 22.4% yield) as a yellow solid. The product was identified as the target product and had a molecular weight of 805.2.

Synthesis example 2: synthesis of Metal Complex 14

A dry 250mL round bottom flask was charged with intermediate 2(1.5g, 4.9mmol), iridium complex 1(2.9g, 4.0mmol), 2-ethoxyethanol (30mL) and DMF (30mL), N in that order₂The reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 14(0.70g, 21.8% yield) as a yellow solid. The product is determined as target product, and has molecular weight805.2。

Synthetic example 3: synthesis of Metal Complex 44

A dry 250mL round bottom flask was charged with intermediate 2(1.6g, 5.2mmol), iridium complex 2(3.1g, 4.0mmol), 2-ethoxyethanol (25mL) and DMF (25mL), N in that order₂The reaction is heated for 144h at 90 ℃ under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 44(0.58g, 17.5% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 833.2.

Synthetic example 4: synthesis of Metal Complex 103

A dry 250mL round bottom flask was charged with intermediate 3(1.2g, 3.9mmol), iridium complex 3(2.5g, 3.2mmol), 2-ethoxyethanol (20mL) and DMF (20mL), N in that order₂The reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 103(0.85g, 30.9% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 861.2.

Synthesis example 5: synthesis of Metal Complex 389

A dry 250mL round bottom flask was charged with intermediate 4(1.6g, 4.2mmol), iridium complex 4(2.6g, 3.2mmol), 2-ethoxyethanol (25mL) and DMF (25mL) in that order,N₂the reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 389(0.48g, 15.1% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 993.3.

It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.

Device example 1

First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees^-8In the case of torr, the evaporation was carried out on the ITO anode in turn by thermal vacuum evaporation at a rate of 0.2-2 a/s. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). Compound H1 was used as Electron Blocking Layer (EBL). The metal complex 4 of the present invention is then doped in a compound H1 and a compound H2 and co-deposited as a light-emitting layer (EML). On EML, compound H3 acts as a Hole Blocking Layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.

Device example 2

Device example 2 was carried out in the same manner as in device example 1, except that the metal complex 14 of the present invention was used in place of the metal complex 4 of the present invention in the light-emitting layer (EML).

Device example 3

Device example 3 was carried out in the same manner as in device example 1 except that the metal complex 44 of the present invention was used in place of the metal complex 4 of the present invention in the light-emitting layer (EML).

Device example 4

Device example 4 was implemented in the same manner as in device example 1 except that the metal complex 389 of the present invention was used in the light-emitting layer (EML) instead of the metal complex 4 of the present invention.

Device comparative example 1

Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD1 in the light-emitting layer (EML).

Device comparative example 2

Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD2 in the light-emitting layer (EML).

Device comparative example 3

Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD3 in the light-emitting layer (EML).

The detailed device layer structure and thickness are shown in table 1 below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.

Table 1 device structure of device embodiments

The material structure used in the device is as follows:

the IVL characteristics of the device were measured. At 1000cd/m²The CIE data of the devices, the maximum emission wavelength lambda, were measured_maxFull width at half maximum (FWHM), voltage (V) and External Quantum Efficiency (EQE). These data are recorded and presented in table 2.

TABLE 2 device data

Discussion:

table 2 shows the device properties of the examples and comparative examples. From the data in Table 2 we find that_aIn comparison with comparative example 1 in which the ligand is not substituted, examples 1 and 2 have emission wavelengths blue-shifted by 4 to 5nm and have more saturated green emission. Moreover, the EQE of the devices of example 1 and example 2 reached 24.37% and 24.65%, respectively, which are both higher than 23.39% of comparative example 1, and further improved based on the fact that comparative example 1 is already in the field. In addition, the device voltages of example 1 and example 2 were both reduced by about 0.35V compared to comparative example 1.

At L_aY of the ligand₂And Y₃The spectrum of comparative example 3, in which all the positions are substituted with deuterated methyl groups, is similar to that of examples 1 and 2, but the EQE of comparative example 3 is reduced to a different extent than that of examples 1 and 2, and the device voltage is also higher than that of examples 1 and 2.

At L_aY of the ligand₁The maximum emission wavelength of comparative example 2 having fluorine substitution at the position was red-shifted by approximately 20nm as compared with examples 1 and 2, and the half-peak widths were respectively widened by 18.5nm and 23.9nm, so that the emission color of comparative example 2 was not saturated. In addition, the EQE of comparative example 2 is somewhat lower than both example 1 and example 2, and the device voltage of comparative example 2 is also slightly higher than that of example 1 and example 2.

The above results show that the metal complexes of the invention with ligands substituted at a specific position F are compared to L_aMetal complexation without substitution or substitution of other alkyl or fluorine at the same position of ligand improves device performance, especially reduces voltage and EQEAnd the improvement of the light emitting color saturation.

Examples 3 and 4 are both greatly enhanced, both exhibiting higher EQE, and lower driving voltage, compared to comparative examples 1-3. Among them, the driving voltage of example 3 was reduced by 0.5V, 0.22V and 0.21V, respectively, compared to comparative examples 1 to 3. Example 4 the EQE using a metal complex featuring the present invention reached 26.52%, which is about 13.4%, 15.2% and 14.6% higher than comparative examples 1 to 3, respectively, while the half-peak width of example 4 is much narrower, only 32.3nm, which is at a very high level in the industry.

The results show that compared with metal complexes with fluorine substitution at other positions of the ligand, the metal complex with the F-substituted ligand at a specific position of the invention also improves the device performance, especially improves the luminescent color saturation, narrows the half-peak width, improves the EQE and reduces the voltage.

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

Claims (23)

1. A metal complex comprising a metal M, and a ligand L coordinated to the metal M_aWherein L is_aHas a structure represented by formula 1:

in the formula 1, the first and second groups,

the metal M is selected from metals having a relative atomic mass greater than 40;

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₁-X₈selected from C, CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_yeach occurrence, the same or different, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

X₁-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_xAnd R_yCan optionally be linked to form a ring.

2. The metal complex of claim 1, wherein L_aHas a structure represented by one of formulas 1a-1 e:

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₁-X₈selected from CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_yeach occurrence, the same or different, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

X₁-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_xAnd R_yCan optionally be linked to form a ring.

3. The metal complex as claimed in claim 1 or 2, wherein the metal complex has M (L)_a)_m(L_b)_n(L_c)_qA general formula (II) of (I);

wherein the content of the first and second substances,

the metal M is selected from metals having a relative atomic mass greater than 40; preferably, M is selected, identically or differently on each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;

L_a、L_band L_cAre respectively a first, a second and a third ligand coordinated to the metal M, and L_cAnd said L_aOr L_bAre the same or different; wherein L is_a、L_bAnd L_cOptionally linked to form a multidentate ligand;

m1, 2 or 3, n 0, 1 or 2, q 0, 1 or 2, M + n + q being equal to the oxidation state of the metal M; when m is 2 or more, a plurality of L_aThe same or different; when n is equal to 2, two L_bThe same or different; when q is equal to 2, two L_cThe same or different;

L_band L_cA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:

wherein the content of the first and second substances,

R_a，R_band R_cThe same or different at each occurrence represents mono-, poly-, or no substitution;

X_beach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NR_N1，CR_C1R_C2；

R_a，R_b，R_c，R_N1，R_C1And R_C2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted hetero having 1 to 20 carbon atomsAn alkyl group, 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 carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, sulfinyl, sulfonyl, phosphino, and combinations thereof;

adjacent substituents R_a，R_b，R_c，R_N1，R_C1And R_C2Can optionally be linked to form a ring.

4. The metal complex according to any one of claims 1 to 3, wherein the metal complex has a structure represented by formula 2:

wherein the content of the first and second substances,

m is selected from 1,2 or 3; when m is 1, two L_bThe same or different; when m is 2 or 3, a plurality of L_aThe same or different;

z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;

X₃-X₈selected from CR, identically or differently at each occurrence_xOr N;

Y₁-Y₄selected from CR, identically or differently at each occurrence_yOr N;

R，R_x，R_y，R₁-R₈each occurrence, the same or different, is selected from the group consisting of: hydrogen, the presence of deuterium,halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

X₃-X₈at least one of which is CR_xAnd said R is_xIs cyano;

Y₂and Y₃At least one of which is CR_yAnd said R is_yIs F;

adjacent substituents R, R_x，R_y，R₁-R₈Can optionally be linked to form a ring.

5. The metal complex of any one of claims 1 to 4, wherein Z is selected from O and S; preferably, Z is O.

6. A metal complex as claimed in any one of claims 1 to 5, wherein Y is₁-Y₄Selected from CR, identically or differently at each occurrence_yAnd Y is₂And Y₃At least one of which is CR_yAnd said R is_yIs F.

7. The metal complex as claimed in any one of claims 1 to 6, wherein Y is₂And Y₃At least one of which is CR_yAnd said R is_yIs F; when Y is₁-Y₄The remainder of (B) are selected from CR_yWhen R is_yEach occurrence, the same or different, 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 ring 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;

preferably, when Y is₁-Y₄The others of (A) and (B) are selected from CR_yWhen R is_yEach occurrence, the same or different, 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 ring carbon atoms, and combinations thereof;

more preferably, when Y is₁-Y₄The others of (A) and (B) are selected from CR_yWhen R is_ySelected from hydrogen, deuterium, methyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, tert-pentyl, or combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.

8. The metal complex as claimed in any one of claims 1 to 6, wherein Y is₂And Y₃At least one of which is CR_yAnd said R is_yIs F; y is₁-Y₄At least one further one of (A) is selected from CR_yAnd at least one R_yIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring 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. The metal complex as claimed in any one of claims 1 to 6, wherein Y is₂Is CR_yAnd said R is_yIs fluorine; and Y is₃Is CR_ySaid R is_ySelected from the group consisting of: deuterium, substituted or unsubstituted with 1-10A carbon atom alkyl group, a substituted or unsubstituted cycloalkyl group having from 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 15 carbon atoms, and combinations thereof;

or, Y₃Is CR_yAnd said R is_yIs fluorine; and Y is₂Is CR_ySaid R is_ySelected 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 ring 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.

10. The metal complex of claim 1, wherein X₁-X₈Selected from C or CR, identically or differently at each occurrence_x。

11. A metal complex according to claim 1, wherein X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfo groups having from 0 to 20 carbon atomsAcyl, phosphino, and combinations thereof;

preferably, X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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, mercapto groups, and combinations thereof;

more preferably, X₁-X₈At least two of which are CR_xAnd said one R_xIs cyano, and additionally at least one R_xIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring 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.

12. A metal complex according to any one of claims 1 to 11, wherein X₅-X₈In (1), at least one is CR_xAnd said R is_xIs cyano;

preferably, X₇Is CR_xAnd said R is_xIs cyano, or X₈Is CR_xAnd said R is_xIs cyano.

13. A metal complex according to claim 4, wherein R₂，R₃，R₆，R₇At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;

preferably, R₂，R₃，R₆，R₇At least one or at least two or at least three or all 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;

more preferably, R₂，R₃，R₆，R₇At least one or at least two or at least three or all are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.

14. A metal complex as claimed in any one of claims 1 to 3, wherein L_aEach occurrence being the same or different and selected from any one of the group consisting of:

15. a metal complex as claimed in claim 3 or 14 wherein L_bEach occurrence, the same or different, is selected from the group consisting of:

16. the metal complex of claim 15, wherein the metal complex has Ir (L)_a)₂(L_b) Or Ir (L)_a)(L_b)₂Or Ir (L)_a)₃In which L is_aEach occurrence being selected identically or differently from L_a1To L_a766Any one or any two or any three of the group consisting of, L_bIs selected from the group consisting of L_b1To L_b80Any one or two of the group consisting of;

preferably, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 390, wherein metal complex 1 to metal complex 390 has IrL_a(L_b)₂Wherein two L are_bSame wherein L_aAnd L_bRespectively corresponding to the structures indicated in the following table:

17. an electroluminescent device, comprising:

an anode, a cathode, an anode and a cathode,

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of any one of claims 1 to 16.

18. The electroluminescent device of claim 17, wherein the organic layer comprising the metal complex is a light emitting layer.

19. The electroluminescent device of claim 18 wherein the light emitting layer is green emitting.

20. The electroluminescent device of claim 18 wherein the light-emitting layer comprises at least one first host compound;

preferably, the light-emitting layer further comprises at least two host compounds;

more preferably, 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, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

21. The electroluminescent device of claim 20, wherein the first host compound has a structure represented by formula 3:

wherein the content of the first and second substances,

L_xeach occurrence of a phaseOr different from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

v is selected, identically or differently on each occurrence, from C, CR_vOr N, and at least one of V is C, and with L_xConnecting;

u is selected, identically or differently on each occurrence, from C, CR_uOr N, and at least one of U is C, and with L_xConnecting;

R_vand R_uEach occurrence, identically or differently, 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, 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, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Ar₁each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

adjacent substituents R_vAnd R_uCan optionally be linked to form a ring;

preferably, wherein the second host compound has a structure represented by one of formulae 3-a to 3-j:

22. the electroluminescent device as claimed in claim 20, wherein a metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1-30% of the total weight of the light-emitting layer;

preferably, the weight of the metal complex accounts for 3% -13% of the total weight of the light-emitting layer.

23. A combination of compounds comprising the metal complex of any one of claims 1-16.

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