Organic electroluminescent material and device thereof
By using La-ligand metal complexes of Formula 1 in OLED devices, the problems of unsaturation and short lifetime of blue phosphorescent devices are solved, the efficiency and color control capability of electroluminescent devices are improved, and better overall performance is achieved.
Patent Information
- Application Number
- CN202411862929.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-06-07
- Filing Date
- 2024-12-17
- Publication Date
- 2025-12-09
AI Technical Summary
Existing OLED devices suffer from problems such as blue unsaturation, short device lifespan, and high operating voltage in blue phosphorescent devices. Furthermore, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, affecting the performance of full-color OLED displays.
A novel metal complex with a La ligand having a structure of Formula 1 is used as a charge transport material and a light-emitting material in electroluminescent devices, and the device performance is improved by controlling the emission color.
It achieves better device performance, especially in terms of current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE), while effectively controlling the emission color and improving the overall performance of electroluminescent devices.
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Figure CN121085960A_ABST
Abstract
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 comprising a La ligand having the structure of Formula 1, and an electroluminescent device and compound combination 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 layer and a light-emitting 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 light-emitting 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 fabrication on 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] CN115710290A discloses a metal complex comprising a ligand structure having the following structure: The following metal complexes were disclosed: However, the application did not disclose or teach about the specific structure of the adjacent substituents on the Cy ring, nor did it explain the effect of X4 substitution on device performance.
[0009] This invention provides a novel metal complex comprising a La ligand having a structure of Formula 1, which can be used as a charge transport material, luminescent material, or host material in electroluminescent devices. These novel metal complexes can provide better device performance. Summary of the Invention
[0010] This invention aims to provide a series of novel metal complexes (compounds) with La ligands having the structure of Formula 1 to solve at least some of the above-mentioned problems. These metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can provide better device performance.
[0011] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand La coordinated to the metal M;
[0012] Wherein, metal M is selected from metals with a relative atomic mass greater than 40; La has a structure represented by Equation 1:
[0013]
[0014] in,
[0015] G1 is selected from single bonds, O or S each time it appears, either the same or different;
[0016] X1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0017] X2-X6 are selected from CR each time they appear, either the same or different. x 'or N;
[0018] Y1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0019] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0020] Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different.
[0021] Each time the Cy ring appears, it is selected from an aromatic ring containing Y1 with 6-24 ring atoms, a heteroaromatic ring containing Y1 with 5-24 ring atoms, or a combination thereof;
[0022] Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0023] R 1 R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0024] There exists at least one R 1 It is adjacent to Cy1 in the Cy ring;
[0025] R 3 It is adjacent to ring Cy in ring Cy1;
[0026] R 1 R 2 R 3 R 4 R 5 、R'、R x Each time 'and R' appears, it is selected from the group consisting of the same or different groups of the following: 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... Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0027] And there exists at least one R. 1 and / or R 3Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0028] Among them, at least one of X3-X6 is selected from CR. x ', and the R x Each occurrence has the same or different structure as Equation 2; wherein at least one of X3-X6 is selected from CR x ', and the R x Selected from cyano or fluorine;
[0029] R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0030] Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a loop;
[0031] "---" indicates the connection position.
[0032] According to another embodiment of the present invention, the application of the metal complex in electroluminescent devices is also disclosed.
[0033] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex having a La ligand having a structure of Formula 1.
[0034] According to another embodiment of the invention, a compound combination comprising the metal complex having a La ligand of Formula 1 is also disclosed.
[0035] The novel metal complexes disclosed in this invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes can provide better device performance; in particular, they have significant advantages in terms of CE, PE, and EQE, and enable effective control of emission color, thereby improving the overall performance of electroluminescent devices. Attached Figure Description
[0036] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and combinations of compounds disclosed herein.
[0037] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain compounds and combinations of compounds disclosed herein. Detailed Implementation
[0038] 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.
[0039] 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.
[0040] 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.
[0041] 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.
[0042] 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 1The 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.
[0043] 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.
[0044] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0045] 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.
[0046] 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.
[0047] 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.
[0048] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0049] On the other hand, E-type delayed fluorescence does not 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.
[0050] 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).
[0051] Definition of the term "substituent group"
[0052] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0053] 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.
[0054] 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.
[0055] 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.
[0056] 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.
[0057] 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.
[0058] Aryl or aromatic group – 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.
[0059] 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.
[0060] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. 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 dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] 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.
[0066] 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.
[0067] 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.
[0068] 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.
[0069] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.
[0070] 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.
[0071] 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.
[0072] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, 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.
[0073] 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.
[0074] 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:
[0075]
[0076] 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:
[0077]
[0078] 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:
[0079]
[0080] 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:
[0081]
[0082] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand La coordinated to the metal M;
[0083] Wherein, metal M is selected from metals with a relative atomic mass greater than 40; La has a structure represented by Equation 1:
[0084]
[0085] in,
[0086] G1 is selected from single bonds, O or S each time it appears, either the same or different;
[0087] X1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0088] X2-X6 are selected from CR each time they appear, either the same or different. x 'or N;
[0089] Y1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0090] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0091] Z1 is selected from N, B, P, CR, and SiR each time it appears, either the same or different.
[0092] Or GeR”;
[0093] Each time the Cy ring appears, it is selected from an aromatic ring containing Y1 with 6-24 ring atoms, a heteroaromatic ring containing Y1 with 5-24 ring atoms, or a combination thereof;
[0094] Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0095] R 1 R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0096] There exists at least one R 1 It is adjacent to Cy1 in the Cy ring;
[0097] R 3 It is adjacent to ring Cy in ring Cy1;
[0098] R 1 R 2 R 3 R 4 R 5 、R'、R x Each time 'and R' appears, it is selected from the group consisting of the same or different groups of the following: 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... Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0099] And there exists at least one R. 1 and / or R 3Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0100] Among them, at least one of X3-X6 is selected from CR. x ', and the R x Each occurrence has the same or different structure as Equation 2; and at least one of X3-X6 is selected from CR. x ', and the R x Selected from cyano or fluorine;
[0101] R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0102] Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a loop;
[0103] "---" indicates the connection position.
[0104] In this article, "at least one R" 1 "Adjacent to ring Cy1 in ring Cy" means that there is at least one R in ring Cy. 1 It is adjacent to Cy1, meaning it has at least one R. 1 Cy1 is an adjacent group on the Cy ring.
[0105] R 1 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted; among which,
[0106] When R 1 When it is a monosubstitution, R 1 It is adjacent to Cy1 in the Cy ring;
[0107] When R 1 When there is multiple substitution, at least one R 1 It is adjacent to Cy1 in the ring Cy, and the rest are R. 1 It is either adjacent to or not adjacent to Cy1 in the Cy ring.
[0108] In this article, "R" 3 "Adjacent to ring Cy in ring Cy1" means that R is on ring Cy1. 3 It is adjacent to the ring Cy, i.e., R 3 It is an adjacent group on the cyclic Cy1.
[0109] In this paper, "adjacent substituent R" 2 R 3 R 4 R 5 "Optionally connected to form a ring" is intended to indicate that adjacent sets of substituents, such as two substituents R, are involved. 2 Between the two substituents R 4 Between the two substituents R 5 Between, substituent R 2 and R 3 Between, substituent R 4 and R 5 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0110] According to one embodiment of the present invention, at least one of X5-X6 is selected from CR.x ', and R x Each time it appears, it has the same or different structure as Equation 2.
[0111] According to one embodiment of the present invention, X6 is selected from CR x ', and R x Each time it appears, it has the same or different structure as Equation 2.
[0112] According to one embodiment of the present invention, at least one of X5-X6 is selected from CR. x ', and R x 'Selected from cyano or fluorine.'
[0113] According to one embodiment of the present invention, X5 is selected from CR x ', and R x 'Selected from cyano or fluorine.'
[0114] According to one embodiment of the present invention, a metal complex is disclosed, comprising a metal M and a ligand La coordinated to the metal M; wherein the metal M is selected from metals with a relative atomic mass greater than 40; and La has a structure represented by formula 1-a:
[0115]
[0116] in,
[0117] Ar has the same or different structure as Equation 2 each time it appears;
[0118] G1 is selected from single bonds, O or S each time it appears, either the same or different;
[0119] X1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0120] X2, X3, and X4 are selected from CR each time they appear, either in the same or different ways. x 'or N; Y1 is selected from C or N each time it appears, and is connected to metal M through G1;
[0121] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0122] Z1 is selected from N, B, P, CR, and SiR each time it appears, either the same or different.
[0123] Or GeR”;
[0124] Each time the Cy ring appears, it is selected from an aromatic ring containing Y1 with 6-24 ring atoms, a heteroaromatic ring containing Y1 with 5-24 ring atoms, or a combination thereof;
[0125] Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0126] R 1 R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0127] There exists at least one R 1 It is adjacent to Cy1 in the Cy ring;
[0128] R 3 It is adjacent to ring Cy in ring Cy1;
[0129] R 1 R 2 R 3 R 4 R 5 、R'、R x Each time 'and R' appears, it is selected from the group consisting of the same or different groups of the following: 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... Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0130] And there exists at least one R. 1 and / or R 3Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0131] R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0132] Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a loop;
[0133] "---" indicates the connection position.
[0134] According to one embodiment of the present invention, each occurrence of the ring Cy is selected from a heteroaromatic ring containing Y1 having 5-24 ring atoms, wherein Y1 is C or N, preferably N; each occurrence of the ring Cy1, ring Cy2 and Cy3 is selected from substituted or unsubstituted aromatic rings having 6-24 ring atoms.
[0135] According to one embodiment of the present invention, wherein the rings Cy, Cy1, Cy2, and Cy3, each time they appear, are selected from the group consisting of: pyrrole ring, furan ring, thiophene ring, imidazole ring, pyrazole ring, thiazole ring, oxazole ring, benzene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, indole ring, benzimidazole ring, benzofuran ring, benzothiophene ring, benzothiazole ring, benzoxazole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, and pyridoindole ring.
[0136] According to one embodiment of the present invention, wherein the rings Cy1, Cy2 and Cy3, each time they appear, are selected from the group consisting of: benzene ring, pyridine ring, indole ring, benzimidazole ring, carbazole ring, pyridoindole ring, benzofuran ring, benzothiophene ring, benzothiazole ring, benzoxazole ring, dibenzofuran ring, and dibenzothiophene ring.
[0137] According to one embodiment of the present invention, the rings Cy1, Cy2 and Cy3 are selected from the group consisting of benzene rings and pyridine rings, respectively, each time they appear.
[0138] According to an embodiment of the present invention, wherein, in Formula 1 Each time it appears, choose the same or different structure from any of the following groups:
[0139]
[0140]
[0141] In each occurrence, G1 is selected from single bonds, O or S, and is connected to the metal M;
[0142] Cy1 is selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0143] R 1 R 2 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0144] Among them, there exists at least one R 1 Adjacent to Cy1;
[0145] R 1 R 2 R 3 R g Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0146] And there exists at least one R. 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0147] Indicates the connection location.
[0148] According to an embodiment of the present invention, wherein, in Formula 1 Each time it appears, choose the same or different structure from any of the following groups:
[0149]
[0150] In each occurrence, G1 is selected from single bonds, O or S, and is connected to the metal M;
[0151] Cy1 is selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0152] R 1 R 2 R y Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0153] Among them, R 1 Adjacent to Cy1;
[0154] R 1 R 2 R 3 R y and R g Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0155] And there exists at least one R.1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0156] This indicates the connection location. According to one embodiment of the invention, the metal complex has M(La). m (Lb) n The general formula;
[0157] La and Lb are the first and second ligands that coordinate with metal M, respectively. La and Lb can be optionally linked to form a polydentate ligand.
[0158] m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m+n equals the oxidation state of metal M; when m is greater than or equal to 2, multiple Las may be the same or different; when n is equal to 2, two Lbs may be the same or different; each occurrence of Lb is selected from any of the following groups of structures:
[0159]
[0160] in,
[0161] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 CR C1 R C2 ;
[0162] R a and R bEach occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0163] R a R b R c R N1 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0164] Adjacent substituent R a R b R c R N1 R C1 and R C2 They can be arbitrarily connected to form a ring.
[0165] In this paper, "adjacent substituent R" a R b R c R N1 R C1 and R C2 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a Between the two substituents R b Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R cBetween, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, and R C1 and R C2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring. For example, adjacent substituents R a R b They can be arbitrarily connected to form a loop, when R a When arbitrarily connected to form a loop, It can form The structure.
[0166] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.
[0167] According to one embodiment of the present invention, M is selected from Pt or Ir.
[0168] According to one embodiment of the present invention, the metal complex Ir(La) m (Lb) n It has a structure represented by Equation 3A or Equation 3B:
[0169]
[0170]
[0171] in,
[0172] m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m + n = 3; when m is greater than or equal to 2, multiple La are the same or different; when n is equal to 2, two Lb are the same or different.
[0173] Ar has the same or different structure as Equation 2 each time it appears;
[0174] G1 is selected from single bonds, O or S each time it appears, either the same or different;
[0175] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0176] Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different.
[0177] U1-U4 are selected from CR each time they appear, either in the same or different ways. a Or N;
[0178] U5-U8 are selected from CR each time they appear, either the same or different. b Or N;
[0179] Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0180] R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0181] R 3 It is adjacent to the pyridine ring in the Cy1 ring;
[0182] R 1 R 2 R 3 R 4 R 5 R a R bR' and R" are selected, in the same or different groups of the following: 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, and so on. Alkyne groups having 2-20 carbon atoms, 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), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.
[0183] And there exists at least one R. 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0184] R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0185] Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a ring.
[0186] According to one embodiment of the present invention, wherein adjacent substituents R a R b They can be arbitrarily connected to form a ring.
[0187] In this paper, "adjacent substituent R" a R b "Optionally connected to form a ring" is intended to indicate that adjacent sets of substituents, such as two substituents R, are involved. a Between the two substituents R b Between, substituent R a and R b Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0188] According to one embodiment of the present invention, the metal complex Ir(La) m (Lb) n It has a structure represented by Equation 3C or Equation 3D:
[0189]
[0190]
[0191] in,
[0192] m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m + n = 3; when m is greater than or equal to 2, multiple La are the same or different; when n is equal to 2, two Lb are the same or different.
[0193] Ar has the same or different structure as Equation 2 each time it appears;
[0194] G1 is selected from single bonds, O or S each time it appears, either the same or different;
[0195] Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different.
[0196] Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different.
[0197] U1-U4 are selected from CR each time they appear, either in the same or different ways. a Or N;
[0198] U5-U8 are selected from CR each time they appear, either the same or different. b Or N;
[0199] Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof;
[0200] R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.
[0201] R 3 It is adjacent to the pyridine ring in the Cy1 ring;
[0202] R 1 R 2 R 3 R 4 R 5 R y R a R bR' and R" are selected, in the same or different groups of the following: 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, and so on. Alkyne groups having 2-20 carbon atoms, 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), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.
[0203] And there exists at least one R. 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0204] R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms;
[0205] Adjacent substituent R 2 R 3 R 4 R 5 R a R b They can optionally connect to form a ring. In this paper, "adjacent substituents R..." 2 R 3 R 4 R 5 R a R b "Optionally connected to form a ring" is intended to indicate that adjacent sets of substituents, such as two substituents R, are involved. 2 Between the two substituents R 4 Between the two substituents R 5 Between, substituent R 2 and R 3 Between, substituent R 4 and R 5 Between, substituent R a and R b Between these substituent groups, any one or more of them can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring. According to one embodiment of the invention, G1 is selected from single bonds each time it appears, either identically or differently.
[0206] According to one embodiment of the invention, Z is selected from O or S each time it appears, either the same or different.
[0207] According to one embodiment of the present invention, R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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 alkylgermanium groups having 3 to 20 carbon atoms, and combinations thereof.
[0208] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms.
[0209] According to one embodiment of the present invention, R 1 R 3 Each occurrence is selected, either identically or differently, from the group consisting of: hydrogen, deuterium, fluorine, 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, and combinations thereof; and at least one R is present. 1 and / or R 3 Each time it appears, it is selected from the group consisting of the following, either identically or differently: 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.
[0210] According to one embodiment of the present invention, R 1 R 3 Each occurrence is selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, and combinations thereof; and at least one R is present. 1 and / or R 3 Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.
[0211] According to one embodiment of the present invention, there are one or more R 2 The R 2 Each time it appears, it is selected from the group consisting of the same or different groups of: deuterium, fluorine, 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.
[0212] According to one embodiment of the present invention, there are one or more R 2 The R 2 Each time it appears, it is 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 cyclic carbon atoms, and combinations thereof.
[0213] According to one embodiment of the present invention, R 1 R 3 and at least one R 2 Each time it appears, it is selected from the group consisting of the following, either identically or differently: 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof.
[0214] According to one embodiment of the present invention, R 1 R 3 and at least one R 2 Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.
[0215] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR a And / or at least one of U5-U8 is selected from CR b The R a R b Selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), cycloalkyl groups of 3-20 ring carbon atoms (substituted or unsubstituted), or combinations thereof; and said R a R bThe total number of carbon atoms is greater than or equal to 2.
[0216] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR a And / or at least one of U5-U8 is selected from CR b The R a R b Selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), cycloalkyl groups of 3-20 ring carbon atoms (substituted or unsubstituted), or combinations thereof; and said R a R b The total number of carbon atoms is greater than or equal to 4.
[0217] According to one embodiment of the present invention, Z1 is selected from N each time it occurs.
[0218] According to one embodiment of the present invention, R 4 R 5 Each occurrence is selected, either identically or differently, from the group consisting of: 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, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, and combinations thereof; adjacent substituent R 4 R 5 They can be arbitrarily connected to form a ring.
[0219] According to one embodiment of the present invention, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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.
[0220] According to one embodiment of the present invention, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof.
[0221] According to one embodiment of the present invention, R4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof;
[0222] According to one embodiment of the present invention, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 cyclic carbon atoms, and combinations thereof.
[0223] According to one embodiment of the present invention, Ar is selected from the group consisting of Ar1-Ar104 each time it appears, either the same or different; the structure of Ar1-Ar104 is as described in claim 16.
[0224] According to another embodiment of the invention, each occurrence of La is selected from the group consisting of La-1-k and La-2-k, either identically or differently; the structure of La-1-k and La-2-k is as described in claim 17.
[0225] According to one embodiment of the present invention, Lb is selected from the group consisting of Lb1-Lb167 each time it appears, either the same or different; the structure of Lb1-Lb167 is as described in claim 18.
[0226] According to another embodiment of the invention, the metal complex has the structure IrLa(Lb)2, with two identical Lb; La is selected from the group consisting of La-1-k and La-2-k, k is selected from 1 to 5080, and Lb is selected from the group consisting of Lb1 to Lb167.
[0227] According to another embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 3815 as described in claim 19.
[0228] According to another embodiment of the invention, metal complex 1 to metal complex 3815 may optionally be partially or completely deuterated.
[0229] According to another embodiment of the present invention, the application of the metal complex in electroluminescent devices is also disclosed.
[0230] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a structure having Formula 1. aMetal complexes of ligands.
[0231] According to another embodiment of the present invention, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.
[0232] According to another embodiment of the present invention, the light-emitting layer emits green light or white light.
[0233] According to one embodiment of the present invention, the organic layer further includes a host material.
[0234] According to another embodiment of the present invention, the light-emitting layer comprises a first host compound;
[0235] According to another embodiment of the present invention, the light-emitting layer further comprises a second host compound;
[0236] According to another embodiment of the invention, wherein the first host compound and / or the second host 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.
[0237] According to another embodiment of the present invention, the first host compound has a structure represented by Formula 4:
[0238]
[0239] in,
[0240] E1-E6 are selected from C or CR each time they appear, either identically or differently. e Or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and connected to equation A;
[0241]
[0242] in,
[0243] When Q appears repeatedly, the same or different choices are made from the group consisting of O, S, Se, N, NR", CR”R", SiR”R", GeR”R” and R”C=CR”; when two R” exist simultaneously, the two R” can be the same or different.
[0244] p is 0 or 1; r is 0 or 1;
[0245] When Q is selected from N, p is 0 and r is 1;
[0246] When Q is selected from the group consisting of O, S, Se, NR", CR”R", SiR”R", GeR”R" and R”C=CR”, p is 1 and r is 0;
[0247] L, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.
[0248] Q1-Q8 are selected from C and CR each time they appear, either identically or differently. q Or N;
[0249] R e ,R” and R q 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 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;
[0250] "*" represents the connection position between equation A and equation 4;
[0251] Adjacent substituent R e ,R”R q They can be arbitrarily connected to form a ring.
[0252] In this paper, "adjacent substituent R" e ,R”R q "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R e Between, between the two substituents R”, between the two substituents R qBetween the two substituents R” and R” q Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0253] According to another embodiment of the invention, E1-E6 are selected from C, CR each time they appear, either identically or differently. e Or N, and three of E1-E6 are N, and at least one of E1-E6 is CR. e And the R e Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;
[0254] And / or Q is selected from O, S, N or NR each time it appears, either the same or different;
[0255] And / or at least one or at least two of Q1-Q8 are selected from CR q And the R q Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 5-30 carbon atoms, or combinations thereof;
[0256] And / or L, each time appearing, is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.
[0257] According to another embodiment of the present invention, the first host compound is selected from the group consisting of H-1 to H-243, the structures of which are shown below:
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268]
[0269]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277] According to another embodiment of the present invention, the first host compound is selected from the group consisting of H-244 to H-308, the structures of which are shown below:
[0278]
[0279]
[0280]
[0281]
[0282] According to another embodiment of the present invention, the hydrogen in compounds H-1 to H-308 may be partially or completely replaced by deuterium.
[0283] According to another embodiment of the invention, the second host compound has a structure represented by Formula 5 or Formula 6:
[0284]
[0285] in,
[0286] L x Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.
[0287] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;
[0288] V is selected from C and CR each time it appears, either identically or differently. v Or N, and at least one of V is C, and with L x connect;
[0289] U is selected from C, CR each time it appears, either identically or differently. u Or N, and at least one of U is C, and with L x connect;
[0290] R g R v and R u 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 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;
[0291] Ar6, each time it appears, is selected from the same or different aryl groups with 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 3-30 carbon atoms (substituted or unsubstituted), or combinations thereof.
[0292] Adjacent substituent R g R v and R u They can be arbitrarily connected to form a ring.
[0293] According to another embodiment of the invention, wherein the second host compound has a structure represented by one of formulas 5-a to 5-p:
[0294]
[0295]
[0296] in,
[0297] L x Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.
[0298] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;
[0299] V is selected from C and CR each time it appears, either identically or differently. v Or N, and at least one of V is C, and with L x connect;
[0300] U is selected from C, CR each time it appears, either identically or differently. u Or N, and at least one of U is C, and with L x connect;
[0301] R g R v and R u 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 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;
[0302] Ar6, each time it appears, is selected from the same or different aryl groups with 6-30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 3-30 carbon atoms (substituted or unsubstituted), or combinations thereof.
[0303] Adjacent substituent R g R v and R u They can be arbitrarily connected to form a ring.
[0304] In this article, "adjacent substituent R" g R v and R u "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R g Between the two substituents R v Between the two substituents R u Between, substituent R v and R u Between, substituent R v and R g Between, substituent R g and R u Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0305] According to another embodiment of the present invention, the second main compound is selected from the group consisting of PH-1 to PH-50, the structures of which are shown below:
[0306]
[0307]
[0308]
[0309] According to another embodiment of the present invention, the second main compound is selected from the group consisting of PH-51 to PH-107, the structures of which are shown below:
[0310]
[0311]
[0312]
[0313]
[0314] According to one embodiment of the present invention, the hydrogen in the above-mentioned compounds PH-1 to PH-107 can be partially or completely replaced by deuterium.
[0315] According to one embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer. The hole injection layer can be a single-material functional layer or a functional layer containing multiple materials. The most commonly used multiple materials are hole transport materials doped with a certain proportion of p-type conductive doped materials. Common p-type doped materials include:
[0316]
[0317] According to another embodiment of the present invention, in the light-emitting layer, 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.
[0318] According to another embodiment of the present invention, the metal complex accounts for 3%-13% of the total weight of the luminescent layer.
[0319] According to another embodiment of the invention, a compound combination comprising the metal complex having a La ligand of Formula 1 is also disclosed.
[0320] Combination with other materials
[0321] 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.
[0322] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation 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.
[0323] 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.
[0324] Material synthesis examples:
[0325] 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:
[0326] Synthesis Example 1: Synthesis of Metal Complex 2186
[0327] Step 1:
[0328]
[0329] In a dry 500 mL round-bottom flask, 4.7 g (17.6 mmol) of 5-tert-butyl-2-(3-tert-butylphenyl)-pyridine, 1.5 g (4.2 mmol) of iridium trichloride trihydrate, 120 mL of 2-ethoxyethanol, and 40 mL of water were added sequentially. The mixture was purged three times with nitrogen and kept under nitrogen protection. The mixture was heated and stirred at 130 °C for 24 h. After cooling, the mixture was filtered, washed three times each with methanol and n-hexane, and dried to obtain 3.0 g of intermediate 1 (96% yield).
[0330] Step 2:
[0331]
[0332] In a dry 250 mL round-bottom flask, intermediate 1 (3.0 g, 2.0 mmol), 100 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (1.1 g, 4.3 mmol) were added sequentially. The mixture was purged three times with nitrogen and kept under nitrogen protection. The mixture was stirred overnight at room temperature. The mixture was filtered through diatomaceous earth, washed twice with dichloromethane, and the organic phase was collected and concentrated under reduced pressure to give 3.7 g of yellow solid intermediate 2 (100% yield).
[0333] Step 3:
[0334]
[0335] Intermediate 2 (3.6 g, 3.9 mmol), intermediate 3 (3.8 g, 5.4 mmol), 2-ethoxyethanol (50 mL), and DMF (50 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 100 h under N2 protection. After cooling, the mixture was concentrated under reduced pressure and purified by column chromatography to give a yellow solid metal complex 2186 (3.1 g, 56% yield).
[0336] Synthesis Example 2: Synthesis of Metal Complex 2176
[0337] Step 1:
[0338]
[0339] In a dry 250 mL round-bottom flask, intermediate 2 (1.9 g, 2.2 mmol), intermediate 4 (0.9 g, 2.0 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added sequentially. The mixture was heated at 100 °C for 120 h under N2 protection. After cooling, the mixture was filtered through diatomaceous earth. The solution was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain a yellow solid metal complex 2176 (1.0 g, 40.3% yield). Synthesis Example 3: Synthesis of Metal Complex 2920
[0340] Step 1:
[0341]
[0342] Intermediate 2 (1.6 g, 1.7 mmol), intermediate 5 (1.6 g, 2.1 mmol), 2-ethoxyethanol (30 mL), and DMF (30 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 120 h under N2 protection. After the reaction cooled, the mixture was filtered through diatomaceous earth. The solution was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid metal complex 2920 (1.0 g, 39.9% yield).
[0343] Synthesis Example 4: Synthesis of Metal Complex 3797
[0344] Step 1:
[0345]
[0346] Intermediate 2 (3.3 g, 3.6 mmol), intermediate 6 (3.5 g, 5.0 mmol), 2-ethoxyethanol (60 mL), and DMF (60 mL) were added sequentially to a dry 250 mL round-bottom flask. The mixture was heated at 100 °C for 120 h under N2 protection. After the reaction mixture cooled, it was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved in dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give a yellow solid metal complex 3797 (3.6 g, 71% yield).
[0347] 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.
[0348] Device Examples
[0349] Device Example 1
[0350] First, the glass substrate, which has an 80 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 applied at a vacuum degree of approximately 10... -8Under the condition of Turbo evaporation, ITO anodes are sequentially deposited at a rate of 0.2-2 Å / s via thermal vacuum evaporation. Compounds HT and PD are simultaneously deposited as hole injection layers (HIL). Compound HT is used as a hole transport layer (HTL). Compound PH-1 is used as an electron blocking layer (EBL). Then, the metal complex 2186 of this invention is co-deposited on compounds PH-1 and H-91 as an emissive layer (EML). On the EML, compound H-1 serves as a hole blocking layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) is deposited as an electron injection layer, and a 120 nm thick layer of aluminum is deposited as a cathode. The device is then transferred back to a glove box and encapsulated with a glass cover and desiccant to complete the device.
[0351] Device Example 2
[0352] The implementation method of Device Example 2 is the same as that of Device Example 1, except that the metal complex 2186 of the present invention is replaced by the metal complex 2176 of the present invention in the light-emitting layer.
[0353] Device Comparison Example 1
[0354] The implementation of Comparative Example 1 is the same as that of Example 1, except that GD1 is used instead of metal complex 2186 in the light-emitting layer.
[0355] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.
[0356] Table 1. Device structures of Device Examples 1-2 and Device Comparative Example 1
[0357]
[0358] The material structure used in the device is shown below:
[0359]
[0360]
[0361] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured, including the maximum emission wavelength λ. max Current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) are recorded and presented in Table 2.
[0362] Table 2 Device structure and device data for Device Examples 1-2 and Device Comparative Example 1
[0363] Device ID CIE(x, y) λmax(nm) CE(cd / A) PE (lm / W) EQE (%) Example 1 (0.322,0.651) 531 114.33 118.25 28.44 Example 2 (0.331,0.643) 530 114.59 122.48 28.82 Comparative Example 1 (0.281,0.671) 524 106.00 109.55 27.34
[0364] As can be seen from the data in Table 2, the metal complex 2186 used in Example 1 and the metal complex 2176 used in Example 2 differ from the GD1 used in Comparative Example 1 only in that the metal complex 2186 used in Example 1 and the metal complex 2176 used in Example 2 have the La-specific structure of the present invention, wherein the pyridine linking the dibenzofuran structure also contains ortho-substituted alkyl and aryl structures, while the GD1 used in Comparative Example 1 has two alkyl groups on the pyridine linking the dibenzofuran structure. The results show that, based on the high CE, PE, and EQE of Comparative Example 1, the device performance of Examples 1 and 2 of the present invention has been significantly improved in terms of CE, PE, and EQE compared to Comparative Example 1; at the same time, compared to Comparative Example 1, Examples 1 and 2 have a more obvious red shift in emission color and have also achieved effective control of emission color.
[0365] Device Example 3
[0366] The implementation method of Device Example 3 is the same as that of Device Example 1, except that compound PH-75 is used instead of compound PH-1 in the light-emitting layer (EML); and compound H-250 is used instead of compound H-91.
[0367] Device Comparison Example 2
[0368] The implementation of Comparative Example 2 is the same as that of Example 3, except that GD1 is used instead of metal complex 2186.
[0369] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.
[0370] Table 3. Device structures of Device Example 3 and Device Comparative Example 2
[0371]
[0372] The material structure used in the device is shown below:
[0373]
[0374] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2 The CIE data of the device were measured, including the maximum emission wavelength λ. max Current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) are recorded and presented in Table 4.
[0375] Table 4. Device structures of Device Example 3 and Device Comparative Example 2
[0376] Device ID CIE(x, y) λmax(nm) CE(cd / A) PE (lm / W) EQE (%) Example 3 (0.328,0.646) 531 112 106 27.97 Comparative Example 2 (0.281,0.672) 524 105 98 26.96
[0377] As can be seen from the data in Table 4, the metal complex 2186 used in Example 3 and GD1 used in Comparative Example 2 differ only in structure. The metal complex 2186 used in Example 1 has the La-specific structure of the present invention, wherein the pyridine linking the dibenzofuran structure also contains ortho-substituted alkyl and aryl structures. In contrast, GD1 used in Comparative Example 1 has two alkyl groups on the pyridine linking the dibenzofuran structure. The results show that, based on the high CE, PE, and EQE of Comparative Example 1, the device performance of Example 3 of the present invention has been significantly improved in terms of CE, PE, and EQE compared to Comparative Example 1. At the same time, compared to Comparative Example 2, Example 3 has a more obvious red shift in emission color and also achieves effective control of emission color.
[0378] The above data shows that, in devices with different host materials, the metal complexes with the features of this invention exhibit superior CE, PE, and EQE effects, and achieve effective control of the emitted color, thereby better improving the overall performance of electroluminescent devices.
[0379] Device Example 4
[0380] The implementation method of Device Example 4 is the same as that of Device Example 1, except that the metal complex 2186 is replaced by the metal complex 2920 of the present invention in the light-emitting layer.
[0381] Device Example 5
[0382] The implementation method of Device Example 5 is the same as that of Device Example 1, except that the metal complex 2186 is replaced by the metal complex 3797 of the present invention in the light-emitting layer.
[0383] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.
[0384] Table 5 Device structures of Examples 4-5
[0385]
[0386] The structure of the new material used in the device is shown below:
[0387]
[0388] The IVL characteristics of the device were measured. (At 1000 cd / m²) 2The CIE data of the device were measured, including the maximum emission wavelength λ. max Current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) are recorded and presented in Table 6.
[0389] Table 6 Device Structure and Device Data for Examples 4-5
[0390] Device ID CIE(x, y) λmax(nm) CE(cd / A) PE (lm / W) EQE (%) Example 4 (0.317,0.654) 530 112.78 122.73 28.32 Example 5 (0.320,0.652) 531 114.75 120.32 28.30
[0391] As can be seen from the data in Table 6, both Example 4 using metal complex 2920 with the La-specific structure of the present invention and Example 5 using metal complex 3797 with the La-specific structure of the present invention achieved excellent device performance. The above data indicates that the metal complexes with the characteristics of the present invention have superior CE, PE, and EQE effects, and achieve effective control of the emitted color, thereby better improving the overall performance of the electroluminescent device.
[0392] 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 comprising a metal M and a ligand La coordinated to the metal M; in, Metal M is selected from metals with a relative atomic mass greater than 40; La has a structure represented by Equation 1: in, G1 is selected from single bonds, O or S each time it appears, either the same or different; X1 is selected from C or N each time it appears, and is connected to metal M through G1; X2-X6 are selected from CR each time they appear, either the same or different. x 'or N; Y1 is selected from C or N each time it appears, and is connected to metal M through G1; Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. Z1 is selected from N, B, P, CR each time it appears, either the same or different. SiR” or GeR”; Each time the Cy ring appears, it is selected from an aromatic ring containing Y1 with 6-24 ring atoms, a heteroaromatic ring containing Y1 with 5-24 ring atoms, or a combination thereof; Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; R 1 R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted; at least one R exists. 1 It is adjacent to Cy1 in the Cy ring; R 3 It is adjacent to ring Cy in ring Cy1; R 1 R 2 R 3 R 4 R 5 、R'、R x Each time "and R" appears, it is selected from the following groups, 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 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, and substituted or unsubstituted alkynes having 2-20 carbon atoms. alkyl, 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphin groups, and combinations thereof having 0-20 carbon atoms; And there exists at least one R 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; Among them, at least one of X3-X6 is selected from CR. x ', and the R x Each occurrence has the same or different structure as Equation 2; and at least one of X3-X6 is selected from CR. x ', and the R x Selected from cyano or fluorine; R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a loop; "---" indicates the connection position.
2. The metal complex as described in claim 1, wherein, La has a structure represented by equation 1-a: in, Ar has the same or different structure as Equation 2 each time it appears; G1 is selected from single bonds, O or S each time it appears, either the same or different; X1 is selected from C or N each time it appears, and is connected to metal M through G1; X2, X3, and X4 are selected from CR each time they appear, either in the same or different ways. x 'or N; Y1 is selected from C or N each time it appears, and is connected to metal M through G1; Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different. Each time the Cy ring appears, it is selected from an aromatic ring containing Y1 with 6-24 ring atoms, a heteroaromatic ring containing Y1 with 5-24 ring atoms, or a combination thereof; Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; R 1 R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. There exists at least one R 1 It is adjacent to Cy1 in the Cy ring; R 3 It is adjacent to ring Cy in ring Cy1; R 1 R 2 R 3 R 4 R 5 R x Each time ', R', and R' appear, they are selected from the group consisting of the same or different groups of the following: 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, etc. Alkyne groups having 2-20 carbon atoms, 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), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms. And there exists at least one R 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a loop; "---" indicates the connection position.
3. The metal complex as described in claim 1 or 2, wherein, Each time Cy appears, it is selected from the same or different heteroaromatic rings containing Y1 with 5-24 ring atoms, wherein Y1 is selected from C or N, preferably N; each time Cy1, Cy2 and Cy3 appear, they are selected from substituted or unsubstituted aromatic rings with 6-24 ring atoms. Preferably, the rings Cy, Cy1, Cy2, and Cy3 are selected from the group consisting of the following, either identically or differently each time they appear: pyrrole ring, furan ring, thiophene ring, imidazole ring, pyrazole ring, thiazole ring, oxazole ring, benzene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, indole ring, benzimidazole ring, benzofuran ring, benzothiophene ring, benzothiazole ring, benzoxazole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, pyridoindole ring; Preferably, the rings Cy1, Cy2, and Cy3 are selected from the group consisting of the following, either identically or differently each time they appear: benzene ring, pyridine ring, indole ring, benzimidazole ring, carbazole ring, pyridoindole ring, benzofuran ring, benzothiophene ring, benzothiazole ring, benzoxazole ring, dibenzofuran ring, and dibenzothiophene ring. Preferably, the rings Cy1, Cy2, and Cy3 are selected from the group consisting of the following groups each time they appear, either identically or differently: Benzene ring, pyridine ring.
4. The metal complex as described in claim 1 or 2, wherein, Metal complexes possess M(La) m (Lb) n The general formula; La and Lb are the first and second ligands that coordinate with metal M, respectively. La and Lb can be optionally linked to form a polydentate ligand. m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m+n equals the oxidation state of metal M; when m is greater than or equal to 2, multiple La may be the same or different; when n is equal to 2, two Lb may be the same or different. Lb is selected, either identically or differently, from any of the following groups of structures: in, X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 CR C1 R C2 ; R a and R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R a R b R c R N1 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 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 alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R a R b R c R N1 R C1 and R C2 They can be arbitrarily connected to form a ring.
5. The metal complex as described in claim 1 or 2, wherein, Metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; preferably, M is selected from Pt or Ir.
6. The metal complex according to any one of claims 1-5, wherein, Metal complexes possess Ir(La) m (Lb) n The general formula is given by Ir(La). m (Lb) n It has a structure represented by Equation 3A or Equation 3B: in, m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m + n = 3; when m is greater than or equal to 2, multiple La are the same or different; when n is equal to 2, two Lb are the same or different. Ar has the same or different structure as Equation 2 each time it appears; G1 is selected from single bonds, O or S each time it appears, either the same or different; Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different. U1-U4 are selected from CR each time they appear, either in the same or different ways. a Or N; U5-U8 are selected from CR each time they appear, either the same or different. b Or N; Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. R 3 It is adjacent to the pyridine ring in the Cy1 ring; R 1 R 2 R 3 R 4 R 5 R a R b R' and R" are selected, in the same or different manner, from the group consisting of: 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 groups having 2- Alkenyl groups with 20 carbon atoms, substituted or unsubstituted 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, and ester groups with 0-20 carbon atoms. Cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof; And there exists at least one R 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; Adjacent substituent R 2 R 3 R 4 R 5 They can be arbitrarily connected to form a ring.
7. The metal complex according to any one of claims 1-5, wherein, Metal complexes possess Ir(La) m (Lb) n The general formula is given by Ir(La). m (Lb) n It has a structure represented by Equation 3A or Equation 3B: in, m is selected from 1, 2, or 3, n is selected from 0, 1, or 2, and m + n = 3; when m is greater than or equal to 2, multiple La are the same or different; when n is equal to 2, two Lb are the same or different. Ar has the same or different structure as Equation 2 each time it appears; G1 is selected from single bonds, O or S each time it appears, either the same or different; Each time Z appears, it is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', either the same or different; when two R's exist at the same time, the two R's are the same or different. Z1 is selected from N, B, P, CR", SiR", or GeR" each time it appears, either the same or different. U1-U4 are selected from CR each time they appear, either in the same or different ways. a Or N; U5-U8 are selected from CR each time they appear, either the same or different. b Or N; Cy1, Cy2 and Cy3 are selected, in the same or different ways, from substituted or unsubstituted aromatic rings having 6-24 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-24 ring atoms, or combinations thereof; R 2 R 4 R 5 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. R 3 It is adjacent to the pyridine ring in the Cy1 ring; R 1 R 2 R 3 R 4 R 5 R y R a R b R' and R" are selected, in the same or different groups of the following: 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, and so on. Alkyne groups having 2-20 carbon atoms, 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), alkylgermanium groups having 3-20 carbon atoms (substituted or unsubstituted), arylgermanium groups having 6-20 carbon atoms (substituted or unsubstituted), and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms. And there exists at least one R 1 and / or R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic 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 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-30 carbon atoms. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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 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 2-20 carbon atoms, etc. -Alkyne group with 20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium group with 3-20 carbon atoms, substituted or unsubstituted arylgermanium group with 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof with 0-20 carbon atoms; Adjacent substituent R 2 R 3 R 4 R 5 R a R b They can be arbitrarily connected to form a ring.
8. The metal complex according to any one of claims 1-7, wherein, G1 is selected from a single key each time it appears, either the same or different.
9. The metal complex according to any one of claims 1-7, wherein, Z1 is selected from N each time it appears; Z is selected from O, S or Se each time it appears; preferably, Z is selected from O or S each time it appears, either the same or different; more preferably, Z is selected from O each time it appears.
10. The metal complex according to any one of claims 1-7, wherein, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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 alkylgermanyl groups having 3 to 20 carbon atoms, and combinations thereof; Preferably, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms.
11. The metal complex according to any one of claims 1-7, wherein, R 1 R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; And there exists at least one R 1 and / or R 3 Each time it appears, it is selected from the group consisting of the following, either identically or differently: 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; Preferably, R 1 R 3 Each occurrence is selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, and combinations thereof; and at least one R is present. 1 and / or R 3 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.
12. The metal complex according to any one of claims 1-7, wherein, There are one or more R 2 The R 2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, fluorine, 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; Preferably, there are one or more R 2 The R 2 Each time it appears, it is 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 cyclic carbon atoms, and combinations thereof.
13. The metal complex according to any one of claims 1-7, wherein, R 1 R 3 and at least one R 2 Each time it appears, it is selected from the group consisting of the following, either identically or differently: 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 alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, and combinations thereof; Preferably, R 1 R 3 and at least one R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof.
14. The metal complex as described in claim 6 or 7, wherein, At least one of U1-U4 is selected from CR. a And / or at least one of U5-U8 is selected from CR b The R a R b Selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), cycloalkyl groups of 3-20 ring carbon atoms (substituted or unsubstituted), or combinations thereof; and said R a R b The total number of carbon atoms is greater than or equal to 2; Preferably, at least one of U1-U4 is selected from CR. a And / or at least one of U5-U8 is selected from CR b The R a R b Selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), cycloalkyl groups of 3-20 ring carbon atoms (substituted or unsubstituted), or combinations thereof; and said R a R b The total number of carbon atoms is greater than or equal to 4.
15. The metal complex as described in claim 6 or 7, wherein, R 4 R 5 Each occurrence is selected, either identically or differently, from the group consisting of: 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, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, and combinations thereof; adjacent substituent R 4 R 5 They can be arbitrarily connected to form a loop; Preferably, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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. More preferably, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof. More preferably, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, and combinations thereof; More preferably, R 4 R 5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 cyclic carbon atoms, and combinations thereof.
16. The metal complex according to any one of claims 2-7, wherein, Ar is selected from the group consisting of Ar1-Ar104 each time it appears, either the same or different; the structure of Ar1-Ar104 is as follows: Optionally, the hydrogen in the Ar1-Ar104 can be partially or completely replaced by deuterium.
17. The metal complex of claim 16, wherein, Each occurrence of La is selected, either identically or differently, from the group consisting of La-1-k and La-2-k; the structures of La-1-k and La-2-k are as follows: La-1-k has the following structure: La-2-k has the following structure: Where k, Z, Ar, R 1 R 20 R 3 R 21 R 22 R 23 and R x Details are as follows: Among them, P1-P28 have the following structure: Optionally, the hydrogen in the La-1-k, La-2-k structures can be partially or completely replaced by deuterium.
18. The metal complex of claim 17, wherein, Each time Lb appears, it is selected from the group consisting of Lb1-Lb167, either the same or different; the structure of Lb1-Lb167 is as follows: Optionally, the hydrogen in Lb1-Lb167 can be partially or completely replaced by deuterium.
19. The metal complex of claim 18, wherein, The metal complex has the structure IrLa(Lb)2, with two identical Lb; La is selected from the group consisting of La-1-k and La-2-k, k is selected from 1 to 5080, and Lb is selected from the group consisting of Lb1 to Lb167; Preferably, the metal complex is selected from the group consisting of metal complex 1 to metal complex 3815, wherein the metal complex 1 to metal complex 3796 have the structure IrLa(Lb)2, wherein the two Lb are identical, and La and Lb correspond to the structures shown in the table below: The metal complexes 3797 to 3815 have the following structures: The hydrogen in the metal complexes 1 to 3815 may optionally be partially or completely deuterated.
20. An electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex according to any one of claims 1-19.
21. The electroluminescent device of claim 20, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.
22. The electroluminescent device of claim 21, wherein the light-emitting layer emits green light or white light.
23. The electroluminescent device of claim 20, wherein the organic layer further comprises a host material.
24. The electroluminescent device of claim 21, wherein the light-emitting layer comprises a first host compound; Preferably, the light-emitting layer further comprises a second host compound; Preferably, the first host compound and / or the second host 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.
25. The electroluminescent device of claim 24, wherein the metal complex is doped in the first host compound and the second host compound in the light-emitting layer, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer; Preferably, the metal complex accounts for 3%-13% of the total weight of the light-emitting layer.
26. A compound composition comprising the metal complex of any one of claims 1-19.
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