Organic electroluminescent materials and devices

Abstract

This invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a novel metal complex containing ligands with a specific fused-ring structure. This metal complex, when used as a luminescent material in organic light-emitting devices, exhibits narrow local peak width and high external quantum efficiency, resulting in excellent device performance, particularly in yellow and white light-emitting devices. An organic electroluminescent device containing this metal complex and a compound composition containing this metal complex are also disclosed.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a metal complex having the structure of Formula 1, and organic electroluminescent devices and compound compositions comprising the metal complex. Background Technology

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

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

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

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] EP3450441A1 discloses a metal complex having the following general formula structure: The following specific structure was further disclosed: The application does not disclose the device performance of this compound, nor does it disclose or teach the metal complexes having the structure of Formula 1.

[0009] US20190214584A1 discloses a metal complex having the following general formula structure: Where Y 1 Selected from CRR, SiRR, BR, NR, O, or S, the following specific structures are further disclosed: This application discloses metal complexes with imidazole carbene fused-ring ligands and metal coordination via imidazole carbene, but does not disclose or teach metal complexes having the structure of Formula 1 in this application.

[0010] CN112940041A discloses a platinum metal complex having the following general formula structure: Where L1 is independently selected from C=O, S=O, or S(=O)2, and L2 is independently selected from O, N-R6, or S. The following specific structure is further disclosed: The application discloses that ligands in platinum or palladium metal complexes are bonded to metals through carbonyl ester groups, amide bonds, etc. to form metal complexes, but does not disclose or teach the metal complexes of Formula 1 in this application. Summary of the Invention

[0011] This invention aims to provide a novel phosphorescent metal complex containing a ligand with a specific fused ring structure by introducing such ligand into the metal complex. This metal complex can be used as a luminescent material in organic electroluminescent devices, which can achieve narrow full width at half maximum (FWHM) and high external quantum efficiency.

[0012] According to one embodiment of the present invention, a metal complex is disclosed having a structure represented by Formula 1:

[0013]

[0014] in,

[0015] Metal M is selected from the following groups, either the same or different, each time it appears: Cu, Au, Co, Ru, Rh, Pd, Os, Pt;

[0016] L1 and L2 are selected from single bonds, O, S, and NR each time they appear, either the same or different.

[0017] When T1 and T2 appear, they are selected from the following groups, either identically or differently: single bond, O, S, Se, BR', NR', PR', CR'R', SiR'R', GeR'R', substituted or unsubstituted alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted ynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, and combinations thereof;

[0018] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0019] a and b are selected from 0 or 1 each time they appear, either the same or different.

[0020] X1 to X5 are selected from C and CR each time they appear, either identically or differently. x Or N; when a is selected from 1, X1 is selected from C; when b is selected from 1, X5 is selected from C;

[0021] Y1 is selected from O, S, Se, BR each time it appears, either identically or differently. y NR y PR y SiR y R y or GeR y R y When two Rs appear at the same time y At that time, two R y Same or different;

[0022] Rings A, B, and D are selected, in the same or different ways, from carbon rings having 5 to 30 ring atoms, heterocycles having 5 to 30 ring atoms, or combinations thereof;

[0023] R A R B and R D Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0024] R, R', R A R B R D R x and R yEach time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0025] Adjacent substituents R, R', R A R B R D R x and R y They can be arbitrarily connected to form a ring.

[0026] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises the metal complex described in the foregoing embodiments.

[0027] According to another embodiment of the present invention, a compound combination comprising the metal complexes described in the foregoing embodiments is also disclosed.

[0028] This invention discloses a series of metal complexes having the structure of Formula 1. These metal complexes are a novel class of metal complexes containing ligands with specific fused-ring structures. They can be used as luminescent materials in organic electroluminescent devices and exhibit excellent performance, such as narrow full width at half maximum (FWHM) and high external quantum efficiency. These metal complexes can achieve excellent device performance in organic electroluminescent devices, especially showing promising applications in the fields of yellow and white light emission. Attached Figure Description

[0029] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain combinations of metal complexes and compounds disclosed herein.

[0030] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain combinations of metal complexes and compounds disclosed herein. Detailed Implementation

[0031] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0032] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0033] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0034] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0035] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0036] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). 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, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0037] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0038] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0039] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0040] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0041] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0042] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0043] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0044] Definition of the term "substituent group"

[0045] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0046] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0047] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 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, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0048] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0049] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0050] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0051] Aryl or aromatic group or aromatic ring – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. 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, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0052] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0053] A heteroaryl or heterocyclic ring—as used herein—may comprise 1 to 5 heteroatoms, either non-fused or fused, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. A heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include nitrogen-containing heterocyclic carbenes, dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, imidazolecarbene, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, benzimidazolecarbene, indazole, indazine, benzoxazole, benzoisoxazole, benzyl Thiazoles, quinolines, isoquinolines, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuran-pyridine, furan-dipyridine, benzothiophene-pyridine, thiophene-dipyridine, benzoselene-pyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0054] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0055] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0056] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as 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 preferred. Additionally, the alkyl group may optionally be substituted.

[0057] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0058] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0059] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0060] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0061] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0062] In this disclosure, unless otherwise defined, the terms any one of the following groups shall be used interchangeably: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted... Carboxylic acid group, substituted ester group, substituted sulfinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl group, sulfonyl group, and phosphinyl group. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having 3-20 carbon atoms. Cycloalkyl groups with a ring carbon atom, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 ring atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0063] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0064] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0065] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0066] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0067] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0068]

[0069] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0070]

[0071] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0072]

[0073] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0074]

[0075] According to one embodiment of the present invention, a metal complex is disclosed having a structure represented by Formula 1:

[0076]

[0077] in,

[0078] Metal M is selected from the following groups, either the same or different, each time it appears: Cu, Au, Co, Ru, Rh, Pd, Os, Pt;

[0079] L1 and L2 are selected from single bonds, O, S, and NR each time they appear, either the same or different.

[0080] When T1 and T2 appear, they are selected from the following groups, either identically or differently: single bond, O, S, Se, BR', NR', PR', CR'R', SiR'R', GeR'R', substituted or unsubstituted alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted ynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, and combinations thereof;

[0081] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;

[0082] a and b are selected from 0 or 1 each time they appear, either the same or different.

[0083] X1 to X5 are selected from C and CR each time they appear, either identically or differently. x Or N; when a is selected from 1, X1 is selected from C; when b is selected from 1, X5 is selected from C;

[0084] Y1 is selected from O, S, Se, BR each time it appears, either identically or differently. y NR y PR y SiR y R y or GeR y R y When two Rs appear at the same time y At that time, two R y Same or different;

[0085] Rings A, B, and D are selected, in the same or different ways, from carbon rings having 5 to 30 ring atoms, heterocycles having 5 to 30 ring atoms, or combinations thereof;

[0086] R A R B and R D Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0087] R, R', R A R B R D R x and R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0088] Adjacent substituents R, R', R A R B R D R x and R y They can be arbitrarily connected to form a ring.

[0089] In this paper, "adjacent substituents R, R', R" A R B R D R x and R y The phrase "can be optionally linked to form a ring" is intended to describe adjacent sets of substituents, such as between two substituents R' and two substituents R'. A Between the two substituents R B Between the two substituents RD Between the two substituents R y Between the two substituents R x Between, substituents R and R A Between, substituents R and R B Between, substituents R' and R A Between, substituents R' and R B Between, substituent R x Between R and R', substituent R x and R D Between, substituent R y and R D Between, substituent R x and R y Between these substituent groups, one or more of them can be connected to form a ring. It is also obvious that these substituent groups can be left unconnected to form a ring.

[0090] In this paper, when L1 is selected as a single bond, it means that ring B is directly connected to metal M; when L2 is selected as a single bond, it means that ring A is directly connected to metal M.

[0091] In this paper, when a is selected as 0, it means that T1 does not exist, that is, X1 is not connected to ring A. Then Equation 1 has the following structure: When b is selected as 0, it means that T2 does not exist, that is, X5 is not connected to ring B. Then Equation 1 has the following structure: When both a and b are 0, it means that T1 and T2 do not exist, that is, X1 is not connected to ring A and X5 is not connected to ring B. Then Equation 1 has the following structure:

[0092] In this paper, when a is selected from 1 and T1 is selected from a single bond, it means that X1 is directly connected to ring A through a single bond. In this case, X1 is selected from C, and Equation 1 has the following structure: When b is selected from 1 and T2 is selected from a single bond, it means that X5 is directly connected to ring B through a single bond. In this case, X5 is selected from C, and Equation 1 has the following structure: When a is selected from 1 and T1 is selected from a single bond, and b is selected from 1 and T2 is selected from a single bond, it means that X1 is directly connected to ring A and X5 is directly connected to ring B through single bonds. In this case, X1 and X5 are both selected from C, that is, Equation 1 has the following structure:

[0093] According to one embodiment of the present invention, rings A, B, and D are selected, each time they appear, from the same or different aromatic rings having 5 to 30 ring atoms, heteroaromatic rings having 5 to 30 ring atoms, or combinations thereof.

[0094] According to one embodiment of the present invention, rings A, B, and D are selected, in the same or different ways, from aromatic rings having 6-18 ring atoms, heteroaromatic rings having 5-18 ring atoms, or combinations thereof.

[0095] According to one embodiment of the present invention, rings A, B, and D are selected, in the same or different ways, from aromatic rings having 6-12 ring atoms, heteroaromatic rings having 5-12 ring atoms, or combinations thereof.

[0096] According to one embodiment of the present invention, rings A, B, and D are selected, each time they appear, from an aromatic ring having 6 ring atoms, a heteroaromatic ring having 5-6 ring atoms, or a combination thereof.

[0097] According to one embodiment of the present invention, rings A, B, and D, each time they appear, are selected from the group consisting of: pyrrole ring, furan ring, thiophene ring, selenophene ring, imidazole ring, imidazole carbene ring, oxazole ring, thiazole ring, selenophene ring, benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, naphthylene ring, quinoline ring, isoquinoline ring, benzopyrrole ring, benzofuran ring, benzothiophene ring, benzoselenophene ring, benzoimidazolium ring, benzoimidazolium carbene ring, benzoxazole ring, benzothiazole ring, benzoselenophene ring, fluorene ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzoselenophene ring, azafluorene ring, azacarbazole ring, azadibenzofuran ring, azadibenzothiophene ring, azadibenzoselenophene ring, and combinations thereof.

[0098] According to one embodiment of the present invention, rings A, B, and D are selected from benzene rings, naphthalene rings, pyridine rings, pyrrole rings, furan rings, thiophene rings, imidazole rings, pyridine rings, imidazole carbene rings, benzimidazole rings, benzimidazole carbene rings, benzopyrrole rings, benzofuran rings, or benzothiophene rings each time they appear.

[0099] According to one embodiment of the present invention, L1 and L2 are selected from single bonds, O or S each time they appear.

[0100] According to one embodiment of the present invention, at least one of L1 and L2 is selected from O or S.

[0101] According to one embodiment of the present invention, one of L1 and L2 is selected from a single bond, and the other of L1 and L2 is selected from O or S.

[0102] According to one embodiment of the present invention, L1 is selected from a single bond, and L2 is selected from O or S.

[0103] According to one embodiment of the present invention, both L1 and L2 are selected from single bonds.

[0104] According to one embodiment of the present invention, the metal M is selected from Pt or Pd each time it appears, either the same or different.

[0105] According to one embodiment of the present invention, the metal complex has a structure represented by any one of Formulas 2 to 13:

[0106]

[0107]

[0108] in,

[0109] In equations 2 and 9, X2-X 15 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0110] In equations 3, 10, and 13, X2-X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0111] In Equation 4, X2-X 18 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0112] In Equations 5 and 11, X1-X4 and X6-X 15 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0113] In Equations 6 and 12, X1-X4 and X6-X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0114] In Equation 7, X1-X4 and X6-X 18 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0115] In Equation 8, X2-X 16 Each time it appears, it is selected from CR in the same or different ways. x Or N;

[0116] Y1-Y3 are selected from O, S, Se, BR each time they appear, either identically or differently. y NR y PR y SiR y R y or GeR y R y When two Rs appear at the same time y At that time, two R ySame or different;

[0117] When T1 and T2 appear, they are selected from the following groups, either identically or differently: single bond, O, S, Se, BR', NR', PR', CR'R', SiR'R', GeR'R', substituted or unsubstituted alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted ynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, and combinations thereof;

[0118] R', R x R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0119] Adjacent substituents R', R x R y They can be arbitrarily connected to form a ring.

[0120] In this paper, "adjacent substituents R', R x R y The phrase "can be optionally linked to form a ring" is intended to describe adjacent sets of substituents, such as between two substituents R' and two substituents R'. y Between the two substituents R x Between, substituent R x Between R and R', substituent R x and R y Between these substituent groups, one or more of them can be connected to form a ring. It is also obvious that these substituent groups can be left unconnected to form a ring.

[0121] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 2.

[0122] According to one embodiment of the present invention, in formula 2, X2-X 15 Each time it appears, it is selected from CR in the same or different ways. x .

[0123] According to one embodiment of the present invention, in formula 2, X2-X 15 Each time it appears, it is selected from CR in the same or different ways. x Or N, and at least one of them is selected from N, for example, X2-X 15 One of them is selected from N or X2-X 15 Two of them are selected from N.

[0124] According to one embodiment of the present invention, in Formula 2, X4 is selected from N.

[0125] According to one embodiment of the present invention, in formula 2, X3, X7, X9 and X 11 At least one, two, three, or all of them are selected from CR x And R x It is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, or combinations thereof.

[0126] According to one embodiment of the present invention, in formula 2, Y2 is selected from NR. y And the R y Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.

[0127] According to one embodiment of the present invention, at least one of a and b is selected from 1.

[0128] According to one embodiment of the present invention, a is selected from 1 and b is selected from 0.

[0129] According to one embodiment of the present invention, b is selected from 1 and a is selected from 0.

[0130] According to one embodiment of the invention, T1 and T2, each time they appear, are selected from the group consisting of: single bonds, O, S, Se, BR', NR', PR', CR'R', SiR'R', GeR'R', substituted or unsubstituted alkenyl groups having 2-6 carbon atoms, substituted or unsubstituted ynyl groups having 2-6 carbon atoms, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and combinations thereof.

[0131] According to one embodiment of the invention, T1 and T2, each time they appear, are selected from single bonds, O, S, Se, NR', PR', substituted or unsubstituted vinylenes, substituted or unsubstituted phenylenes, or substituted or unsubstituted pyridylenes.

[0132] According to one embodiment of the present invention, at least one of T1 and T2 is selected from single bonds, O, S, Se, BR', NR', SiR'R' or PR'.

[0133] According to one embodiment of the present invention, at least one of T1 and T2 is selected from a single bond.

[0134] According to one embodiment of the present invention, a is selected from 1, b is selected from 0, and T 1, Selected from single keys.

[0135] According to one embodiment of the present invention, b is selected from 1, a is selected from 0, and T 2, Selected from single keys.

[0136] According to one embodiment of the present invention, Y1 is selected from O or S.

[0137] According to one embodiment of the present invention, Y2-Y3 are selected from O, S, and BR each time they appear, either identically or differently. y or NR y .

[0138] According to one embodiment of the present invention, Y2-Y3 are selected from O, S or NR each time they occur, either identically or differently. y .

[0139] According to one embodiment of the present invention, Y2 is selected from NR. y .

[0140] According to one embodiment of the present invention, wherein R', R x and R yEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof.

[0141] According to one embodiment of the present invention, wherein R', R x and R y Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, and combinations thereof.

[0142] According to one embodiment of the present invention, wherein R', R x and R y Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 18 carbon atoms, and combinations thereof.

[0143] According to one embodiment of the present invention, R x and R y At least one, at least two, or at least three of them are selected from substituted or unsubstituted alkyl groups having 3-12 carbon atoms, or substituted or unsubstituted aryl groups having 6-20 carbon atoms.

[0144] According to one embodiment of the present invention, R x and R y At least one, at least two, or at least three of them are selected from substituted or unsubstituted alkyl groups having 4-12 carbon atoms, or substituted or unsubstituted aryl groups having 6-20 carbon atoms.

[0145] According to one embodiment of the present invention, R x and R yAt least one, at least two, or at least three of them are selected from substituted or unsubstituted alkyl groups having 3 to 6 carbon atoms, or substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0146] According to one embodiment of the present invention, X1-X 18 At least two of them are selected from CR x And the R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 6-30 carbon atoms. Aryl groups with -30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms.

[0147] According to one embodiment of the present invention, wherein the R x Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted cyano groups having 1-20 carbon atoms, and combinations thereof.

[0148] According to one embodiment of the present invention, wherein the R x Each time it appears, it is selected from the group consisting of the following, either the same or different: deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, phenyl, pyridyl, triazine, cyano, and combinations thereof.

[0149] According to one embodiment of the present invention, R A RB and R D Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof.

[0150] According to one embodiment of the present invention, R A R B and R D Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, and combinations thereof.

[0151] According to one embodiment of the present invention, R A R B and R D Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 18 carbon atoms, and combinations thereof.

[0152] According to one embodiment of the present invention, the metal complex is selected from metal complexes C1 to C2. 900 The group consisting of metal complexes C1 to C 900 The specific structure is shown in claim 12.

[0153] According to one embodiment of the present invention, the metal complexes C1 to C 900 In this process, hydrogen energy can be partially or completely replaced by deuterium.

[0154] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises the metal complex described in any of the foregoing embodiments.

[0155] According to one embodiment of the present invention, the organic layer comprising the metal complex is a light-emitting layer.

[0156] According to one embodiment of the present invention, the organic electroluminescent device emits white light.

[0157] According to one embodiment of the present invention, the organic electroluminescent device emits yellow light.

[0158] According to one embodiment of the present invention, the light-emitting layer contains at least one host compound.

[0159] According to one embodiment of the present invention, wherein the main compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0160] According to one embodiment of the present invention, a compound composition comprising the metal complex described in any of the foregoing embodiments is also disclosed.

[0161] Combination with other materials

[0162] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0163] Materials described herein for use in specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the metal complexes disclosed herein can be used in combination with a variety of hosts, delivery layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0164] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0165] Material synthesis examples:

[0166] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0167] Synthesis Example 1: Metal Complex C 240 Synthesis:

[0168] Step 1: Synthesis of intermediate 2:

[0169]

[0170] Dissolve NaH (2.70 g, 67.33 mmol) in 80 mL of DMF. Add intermediate 1 (8.00 g, 56.11 mmol) in DMF solution at 0 °C and stir for 30 minutes. Add ethoxychloromethane (MOECl, 6.30 g, 67.37 mmol) and stir overnight. TLC shows complete disappearance of the starting material. Quench the reaction with ammonium chloride solution. Extract with PE:EA = 15:1 (80 mL * 3). Combine the organic phases, dry to anhydrous magnesium sulfate, and purify by column chromatography (eluent: PE:EA = 15:1, v / v) to give colorless liquid intermediate 2 (10.10 g, 90%).

[0171] Step 2: Synthesis of intermediate 3:

[0172]

[0173] Intermediate 2 (7.20 g, 35.88 mmol) was dissolved in 70 mL of THF. Under a nitrogen atmosphere, a solution of n-butyllithium (27 mL, 43.06 mmol) was slowly added dropwise at 0 °C, and the mixture was stirred at room temperature for 5 hours. Isopropanol pinacol borate (B2Pin2, 8.68 g, 46.64 mmol) was added, and the mixture was stirred overnight. The reaction was quenched with ammonium chloride solution, and the mixture was extracted with EA (70 mL * 3). The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified by column chromatography (eluent: PE:EA = 50:1, v / v) to give intermediate 3 (4.10 g, 43.5%).

[0174] Step 3: Synthesis of intermediate 5:

[0175]

[0176] Tetraphenylphosphine palladium (Pd(PPh3)4, 0.90 g, 0.77 mmol), intermediate 3 (4.10 g, 15.57 mmol), intermediate 4 (5.30 g, 15.57 mmol), and potassium carbonate (4.30 g, 31.14 mmol) were dissolved in 40 mL toluene, 10 mL ethanol, and 5 mL water. The mixture was heated to 85 °C under nitrogen protection and reacted overnight. After the reaction was complete as shown by TLC, the mixture was cooled to room temperature. The solution was diluted with water, extracted with EA (40 mL * 3), and the organic phases were combined, dried over anhydrous magnesium sulfate, and purified by column chromatography (eluent: EA:PE = 1:30, v / v) to give intermediate 5 (3.70 g, 70.3%).

[0177] Step 4: Synthesis of Intermediate 6:

[0178]

[0179] Intermediate 5 (3.70 g, 10.95 mmol), palladium acetate (0.12 g, 0.55 mmol), S-phos (0.45 g, 1.1 mmol), potassium acetate (2.15 g, 21.90 mmol), and bipinacol borate (5.56 g, 21.90 mmol) were dissolved in 40 mL of 1,4-dioxane. The mixture was heated to 110 °C under nitrogen protection and reacted for 6 hours. After the reaction was complete as shown by TLC, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the mixture was purified by column chromatography (eluent: EA:PE = 1:30, v / v) to give intermediate 6 (1.68 g, 35.7%).

[0180] Step 5: Synthesis of intermediate 8:

[0181]

[0182] Intermediate 6 (1.68 g, 3.91 mmol), intermediate 7 (2.2 g, 3.91 mmol), palladium acetate (0.04 g, 0.19 mmol), S-phos (0.16 g, 0.39 mmol), and potassium carbonate (1.08 g, 7.82 mmol) were dissolved in 20 mL of 1,4-dioxane and 5 mL of water. The mixture was heated to 100 °C under nitrogen protection and reacted for 16 hours. After the reaction was confirmed by TLC, the mixture was cooled to room temperature. The solvent was removed under reduced pressure, and the mixture was purified by column chromatography (eluent: EA:PE = 1:30, v / v) to give intermediate 8 (0.2 g, 6%).

[0183] Step 6: Metal Complex C 240 Synthesis:

[0184]

[0185] Intermediate 8 (0.2 g, 0.24 mmol) and potassium chloroplatinate (0.09 g, 0.22 mmol) were dissolved in 5 mL of acetic acid and heated to 130 °C under nitrogen protection for 60 hours. After cooling to room temperature, the mixture was diluted with water, filtered through diatomaceous earth, and the resulting solid was dissolved in dichloromethane. The solvent was removed under reduced pressure, and the mixture was purified by column chromatography (eluent: DCM:PE = 1:2, v / v) to give the metal complex C. 240 (0.17g, 75.37%). The structure of this product was determined to be the target product, with a molecular weight of 1024.4.

[0186] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0187] Device Example 1

[0188] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is sequentially deposited onto the ITO anode by thermal vacuum evaporation at a rate of 0.2–2 Å / s under a vacuum of approximately 10⁻⁸ Torr. Compound HI is used as the hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound EB is used as an electron blocking layer (EBL). Then, the metal complex C of the present invention. 240 Doping was co-deposited in compounds H1 and EB as an emissive layer (EML). H1:EB: Metal complex C 240 =47:47:6). Compound HB is used as a hole blocking layer (HBL). On the HBL, a mixture of the deposited compound ET and 8-hydroxyquinoline-lithium (Liq) serves as an electron transport layer (ETL). (ET:Liq = 40:60). Finally, a 1 nm thick Liq layer was deposited as the electron injection layer, and a 120 nm thick Al layer was deposited as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device. The materials used in the device layer structure were not a single type; different compounds were doped in their stated weight ratios.

[0189] The material structure used in the device is shown below:

[0190]

[0191] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured under varying brightness, including the maximum emission wavelength λ. max External quantum efficiency (EQE) and full width at half maximum (FWHM) data are shown in Table 1.

[0192] Table 1 Device data for Device Example 1

[0193] Device Number CIEx CIEy <![CDATA[λ max (nm)]]> EQE (%) FWHM(nm) Example 1 0.502 0.495 558 20.74 25.9

[0194] discuss:

[0195] As can be seen from Table 1, Device Example 1 uses the metal complex C of this application. 240As a dopant material for the emitting layer, its maximum emission wavelength is 558 nm, exhibiting typical yellow light emission. Currently, most platinum-based phosphorescent complexes have wide full width at half maximum (FWHM) and low device efficiency, making them unsuitable for commercial applications. However, the FWHM of Example 1 of this invention is only 25.9 nm, and its EQE reaches 20.74%, which is at a relatively high efficiency level.

[0196] Currently, the white OLED lights used in daily life mainly produce white light by the combined action of yellow and blue light emitting units. Devices containing metal complexes with the structure of Formula 1 of this invention show excellent device performance and have broad prospects for commercial application in yellow or white light.

[0197] In summary, the metal complexes of the present invention exhibit good overall performance in device applications, especially their excellent full width at half maximum (FWHM) and EQE, and have certain advantages and application prospects in commercial applications.

[0198] The metal complexes of this application will be further illustrated below using DFT calculations. DFT calculations were performed on metal complexes RD1, RD2, RD3, and C. 240 The dipole moment was calculated using Gauss16 software and the B3LYP method, with geometric optimization performed using the CEP-31G basis set.

[0199] Metal complexes RD1, RD2, RD3, C 240 The structure is as follows:

[0200]

[0201] Table 2 Metal complexes RD1, RD2, RD3 and C 240 Dipole moment calculation data

[0202] Metal complexes dipole moment Metal complexes dipole moment RD1 1.855 <![CDATA[C 240 ]]> 1.332 RD2 2.838 RD3 1.498

[0203] Table 2 lists the metal complexes RD1, RD2, RD3 and C. 240 The dipole moment was obtained through DFT calculation. Metal complexes RD1, RD2, and RD3 are all known metal complexes, among which metal complexes RD1 and RD2, RD3, and C... 240 The only difference lies in whether the phenylisoquinoline ligand is linked through oxygen atoms to form a fused ring structure. The dipole moments of metal complexes RD1 and RD2 are 1.855 and 2.838, respectively. The dipole moment of RD2, after forming a fused ring structure through oxygen atom linkage, is significantly larger than that of RD1. However, the dipole moments of metal complexes RD3 and C... 240 The dipole moments are 1.498 and 1.332, respectively. The C atoms, after forming a fused ring structure through oxygen atom bonding... 240The dipole moment decreases relative to RD3, a conclusion that is completely opposite to that of RD1 and RD2.

[0204] Metal complexes RD3 and C 240 This is a metal complex of the Pt(II) system. Those skilled in the art know that Pt(II) system metal complexes have planar structural characteristics, and these metal complexes are significantly affected by their dipole moment. In these phosphorescent luminescent materials, it is generally believed that a large dipole moment indicates that the luminescent material is prone to molecular aggregation in the device, leading to triplet annihilation and thus reducing device efficiency. When the dipole moment is relatively large, aggregation effects are more likely to occur in the device, resulting in more severe luminescence quenching. Therefore, reducing the dipole moment of the platinum complex is of great significance for improving the performance of Pt(II) system metal complex luminescent materials. The calculation results show that the metal complex of this invention is a type of metal complex suitable for organic electroluminescent devices.

[0205] In summary, the metal complexes of the present invention, which connect different aromatic ring systems by heteroatoms, can reduce the dipole moment and exhibit superior device performance, especially narrow half-width and high external quantum efficiency.

[0206] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A metal complex having a structure represented by Formula 2: Formula 2 wherein, Y1is selected from O; In formula 2, X1-X 15 are each, identically or differently at each occurrence, selected from CR x ; the substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl means that any one of the alkyl, cycloalkyl, aryl, heteroaryl groups can be substituted with one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, and combinations thereof. Y2is selected from NR y ; R x each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having from 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, and combinations thereof; R y each occurrence is the same or different selected from the group consisting of substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; wherein tBu represents tert-butyl, iBu represents iso-butyl, and iPr represents iso-propyl; 2. The metal complex of claim 1, wherein, R x each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having from 1-20 carbon atoms, and combinations thereof; R y is selected from a substituted or unsubstituted aryl having from 6-30 carbon atoms.

3. The metal complex of claim 1, wherein, R x each occurrence is the same or different member selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having from 1 to 6 carbon atoms, and combinations thereof; R y each occurrence is the same or different member selected from the group consisting of a substituted or unsubstituted aryl having from 6 to 18 carbon atoms.

4. The metal complex of claim 1, wherein, R x at least one or at least two or at least three of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R 5. The metal complex of claim 1, wherein, R x at least one or at least two or at least three of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R 6. The metal complex of claim 1, wherein, X1-X 15 at least two of which are selected from CR x and the R x each occurrence is the same or different and is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3-20 ring carbon atoms, and combinations thereof.

7. The metal complex of claim 6, wherein, X1-X 15 at least two of R x , and the R x each occurrence is the same or different, selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, and combinations thereof.

8. The metal complex of claim 6, wherein, X1-X 15 at least two of which are selected from CR x and said R x are the same or different at each occurrence and are selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, cyclopentyl, neopentyl, cyclohexyl, trifluoromethyl, and combinations thereof.

9. The metal complex of claim 1, wherein, The metal complex is selected from any one of the group consisting of metal complexes C 11 to C 50 , C 61 to C 100 , C 111 to C 150 , C 153 to C 154 , C 159 to C 162 , C 173 to C 178 , C 185 to C 186 , C 193 to C 194 , C 199 to C 202 , C 213 to C 218 , C 223 to C 224 , C 233 to C 234 , C 239 to C 242 , C 253 to C 258 , C 265 to C 266 , C 785 to C 786 , C 793 to C 794 ​ wherein " indicates the point of attachment of the group; 10. An organic electroluminescent device comprising: Optionally, the metal complex C 11 to C 50 , C 61 to C 100 , C 111 to C 150 , C 153 , C 154 , C 159 to C 162 , C 173 to C 178 , C 185 , C 186 , C 193 , C 194 , C 199 to C 202 , C 213 to C 218 , C 223 , C 224 , C 233 , C 234 , C 239 to C 242 , C 253 to C 258 , C 265 , C 266 , C 785 , C 786 , C 793 , C 794 the hydrogens in C an anode, 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 1-9. The organic layer comprising the metal complex is an emissive layer.

11. The organic electroluminescent device according to claim 10, wherein The organic electroluminescent device emits white light or yellow light.

12. The organic electroluminescent device according to claim 10, wherein The emissive layer comprises at least one host compound.

13. The organic electroluminescent device according to claim 11, wherein At least one of the host compounds comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dithiophene, azadithiophene, difuran, azadifuran, diseladiazole, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

14. The organic electroluminescent device according to claim 13, wherein 15. A compound composition comprising the metal complex of any one of claims 1-9. ​

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