Organic electroluminescent material and device thereof
By using metal complexes with specific ligand structures, the problem of insufficient efficiency and lifetime of orange light OLED in the prior art is solved, and the orange light luminescence effect with high saturation and long life is achieved.
Patent Information
- Application Number
- CN202311722302.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-12-14
- Publication Date
- 2025-06-17
AI Technical Summary
It is difficult to develop efficient and long-lived orange phosphorescence organic light emitting diodes (OLEDs), especially to achieve high saturation luminescence while maintaining high efficiency and long life.
A metal complex with the general formula of M(La)m(Lb)n(Lc)q is used as the luminescent material, wherein the ligand of La has a specific structure, Lb has a fluorine substituent, and Lc is a monoanionic bidentate ligand. This complex is used to construct organic electroluminescent devices to meet the luminescence requirements of the orange light band, and to narrow the luminescence wavelength by optimizing the ligand structure and improve the luminescence saturation.
It realizes high saturation luminescence, improves the current efficiency and power efficiency of the device, and provides better device performance.
Smart Images

Figure CN120157710A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a metal complex having the general formula M(L a ) m (L b ) n (L c ) q , and an organic electroluminescent device and a compound composition comprising the metal complex. Background Art
[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 photoreceptors, organic field effect quantum dots (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between a cathode and an anode. Since OLEDs are a self-emitting solid state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.
[0004] OLEDs can be classified into three different types according to their light-emitting mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlet and triplet states, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, 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 and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain light-emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.
[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.
[0007] The emission color of OLEDs can be achieved through the structural design of the light-emitting materials. OLEDs can include one or more light-emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, there is a desire for a more saturated emission spectrum, higher efficiency, and longer device lifetime.
[0008] US20220363700A1 is a previous application of the applicant, which discloses a ligand metal complexes, and specific compounds are disclosed etc. This application focuses on the application of its compounds in red light emitting devices, and does not disclose or teach the special advantages of its polycyclic ligands when used in combination with phenylpyridine ligands having fluorine substituents on specific rings, nor does it disclose or teach the application of such complexes in orange light emitting devices.
[0009] For orange light-emitting phosphorescent materials, in-depth research and development are still needed to meet the increasing requirements of the industry for device performance, such as device emission color, emission saturation, voltage, device efficiency, device lifetime, etc. Summary of the Invention
[0010] The present invention aims to provide a series of metal complexes with the general formula of M(L a ) m (L b ) n (L c ) q to solve at least part of the above problems. The ligands L a in the metal complexes have substituents at specific positions, and the ligand L b has at least one fluorine substituent. The metal complexes can be used as luminescent materials in organic electroluminescent devices, can meet the desired luminescence requirements in the orange light band, and have an unexpectedly greatly narrowed full width at half maximum, enabling high-saturation luminescence; and can simultaneously endow the device with the advantages of high current efficiency and high power efficiency, and can provide more excellent device performance.
[0011] According to an embodiment of the present invention, a metal complex is disclosed, and the metal complex has the general formula of M(L a ) m (L b ) n (L c ) q , wherein the metal M is selected from metals with a relative atomic mass greater than 40, and L a , L b and L c are the first ligand, the second ligand, and the third ligand coordinated with the metal M respectively;
[0012] L a , L b and L c can optionally be connected to form a multidentate ligand;
[0013] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, and m + n + q is equal to the oxidation state of the metal M; when m is equal to 2, the two L a are the same or different; when n is equal to 2, the two L bSame or different;
[0014] The first ligand L a has a structure represented by Formula 1:
[0015]
[0016] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
[0017] W is the same or different each time it appears and is selected from B, N or P;
[0018] R is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0019] Ring A and ring D are the same or different each time they appear and are selected from a five - membered unsaturated carbon ring, an aromatic ring having 6 - 30 carbon atoms or a heteroaromatic ring having 3 - 30 carbon atoms;
[0020] Ring B is selected from a heterocyclic ring having 2 - 30 carbon atoms or a heteroaromatic ring having 2 - 30 carbon atoms;
[0021] R A 、R B and R D are the same or different each time they appear and represent mono - substitution, multi - substitution or no substitution;
[0022] R A 、R B and R DEach occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0023] Adjacent substituents R A 、R B and R D may optionally be joined to form a ring;
[0024] The second ligand L b has a structure represented by Formula 2:
[0025]
[0026] U1 - U4 are each the same as or different from and are selected from N or CR U ;
[0027] W1 - W4 are each the same as or different from and are selected from N or CR W ;
[0028] R U 、R WEach occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0029] and R W at least one of which is selected from fluorine;
[0030] Adjacent substituents R U 、R W can optionally be linked to form a ring;
[0031] The third ligand L c is selected from monoanionic bidentate ligands.
[0032] According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer containing the metal complex shown in the above embodiment.
[0033] According to another embodiment of the present invention, there is also disclosed a compound composition comprising the metal complex shown in the above embodiment.
[0034] The metal complex with a specific structure disclosed in the present invention can be used as a light-emitting material in an electroluminescent device. The metal complex can meet the desired light-emitting requirements in the orange light band, can unexpectedly greatly narrow the emission wavelength, greatly improve the saturation of device emission, and at the same time can greatly improve the current efficiency and power efficiency of the device, and can provide more excellent device performance. Description of the Drawings
[0035] Figure 1Schematic diagram of an organic light-emitting device that can contain the metal complexes and compound compositions disclosed herein.
[0036] Figure 2 Schematic diagram of another organic light-emitting device that can contain the metal complexes and compound compositions disclosed herein. Detailed Description
[0037] OLEDs can be fabricated on various substrates such as glass, plastic, and metal. Figure 1 Organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. Device 100 can 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 and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of the above patent being incorporated herein by reference.
[0038] There are more examples of each of these layers. For example, U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. 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. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued 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. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety, and include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and uses of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.
[0039] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can 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 can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve the desired emission spectrum.
[0040] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.
[0041] The OLED also requires a encapsulation layer, such as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which Figure 1 Differently, an encapsulation layer 102 can also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function 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 outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.
[0042] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
[0043] The materials and structures described herein can also be used in other organic electronic devices listed above.
[0044] As used herein, "top" means farthest from the substrate, and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" "on" the second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer "contacts" the second layer, there can be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed" "on" the anode.
[0045] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.
[0046] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be termed "photosensitive." When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be termed "auxiliary," but an auxiliary ligand can modify the properties of a photosensitive ligand.
[0047] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can be exceeded by delayed fluorescence beyond the 25% spin statistical limit. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0048] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the conversion between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay from the triplet state, then the fraction of the singlet excited state that is refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.
[0049] The characteristics of E-type delayed fluorescence can be found in an exciplex system or a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).
[0050] Definition of substituent terms
[0051] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.
[0052] Alkyl - As used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. 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 can be optionally substituted.
[0053] Cycloalkyl - As used herein, includes cyclic alkyls. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyls 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, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.
[0054] Heteroalkyl - As used herein, heteroalkyl is formed by substituting one or more carbons in the alkyl chain with heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyls include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.
[0055] Alkenyl - As used herein, it encompasses straight-chain, branched-chain, and cyclic olefin groups. The alkenyl can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.
[0056] Alkynyl - As used herein, it encompasses straight-chain alkynyl groups. The alkynyl can be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.
[0057] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl, and m-quaterphenyl. Additionally, the aryl can be optionally substituted.
[0058] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrothienyl. Additionally, the heterocyclic group may be optionally substituted.
[0059] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups having 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Heteroaryl also refers to heteroaromatic group. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole, and their nitrogen analogs. Additionally, the heteroaryl may be optionally substituted.
[0060] Alkoxy - As used herein, it is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyl-oxy, ethoxyethyl-oxy, methoxymethyl-oxy and ethoxymethyl-oxy. Additionally, the alkoxy can be optionally substituted.
[0061] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.
[0062] Aralkyl - As used herein, it encompasses aryl-substituted alkyl. The aralkyl can be an aralkyl having 7 to 30 carbon atoms, preferably an aralkyl having 7 to 20 carbon atoms, more preferably an aralkyl having 7 to 13 carbon atoms. Examples of aralkyl 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, 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 aralkyl can be optionally substituted.
[0063] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 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, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.
[0064] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.
[0065] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.
[0066] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.
[0067] In terms such as azadibenzofuran and azadibenzothiophene, the term "aza" means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and all such analogs are determined to be included within the terms described herein.
[0068] In the present disclosure, unless otherwise defined, when any one of the terms in the following group is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl group, substituted ester group, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl group, ester group, sulfinyl, sulfonyl, and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0069] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or a linking fragment are considered equivalent.
[0070] In the compounds mentioned in the present 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. Due to enhancing the efficiency and stability of the device, the replacement of other stable isotopes in the compound may be preferred.
[0071] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.
[0072] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, adjacent substituents in the compound cannot connect to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case 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 spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, 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.
[0073] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0074]
[0075] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0076]
[0077] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0078]
[0079] In addition, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be construed as meaning that, when one of two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following formula:
[0080]
[0081] According to one embodiment of the present invention, there is disclosed a metal complex having the general formula M(L a ) m (L b ) n (L c ) q , wherein the metal M is selected from metals having a relative atomic mass greater than 40, L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the metal M, respectively;
[0082] L a , L b and L c can optionally be linked to form a polydentate ligand;
[0083] m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, and m + n + q is equal to the oxidation state of the metal M; when m is equal to 2, the two L a are the same or different; when n is equal to 2, the two L b are the same or different;
[0084] The first ligand L a has a structure represented by Formula 1:
[0085]
[0086] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
[0087] W is the same or different each time it appears and is selected from B, N or P;
[0088] R is selected, at each occurrence, identically or differently, from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0089] Ring A and Ring D are identically or differently selected at each occurrence from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
[0090] Ring B is selected from a heterocyclic ring having 2 to 30 carbon atoms or a heteroaromatic ring having 2 to 30 carbon atoms;
[0091] R A , R B and R D Each occurrence of the same or different means mono-, poly- or no-substitution;
[0092] R A , R B and R DEach occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0093] Adjacent substituents R A 、R B and R D can optionally be joined to form a ring;
[0094] The second ligand L b has a structure represented by Formula 2:
[0095]
[0096] U1-U4 are each the same as or different from and are selected from N or CR U ;
[0097] W1-W4 are each the same as or different from and are selected from N or CR W ;
[0098] R U 、R WEach occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0099] And R W At least one of which is selected from fluorine;
[0100] Adjacent substituents R U 、R W Can optionally be joined to form a ring;
[0101] The third ligand L c Is selected from monoanionic bidentate ligands.
[0102] As used herein, adjacent substituents R A 、R B And R D Can optionally be joined to form a ring, which is intended to mean that in Formula 1, adjacent substituent groups, for example, between adjacent substituents R A Between adjacent substituents R B Between adjacent substituents R D Between adjacent substituents R A And R B And between adjacent substituents R A And R D Among them, any one or more of these substituent groups can be joined to form a ring. Obviously, these adjacent substituent groups can also not be joined to form a ring.
[0103] As used herein, adjacent substituents R U 、R Ware optionally linked to form a ring, which is intended to indicate that in Formula 2, adjacent substituent groups, for example, adjacent substituents R U among, adjacent substituents R W among, and adjacent substituents R U and R W among, any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring at all.
[0104] In this embodiment, L a , L b and L c are optionally linked to form a polydentate ligand. For example, any two or three of L a , L b and L c can be linked to form a tetradentate ligand or a hexadentate ligand. Obviously, L a , L b and L c can also not be linked to not form a polydentate ligand.
[0105] According to an embodiment of the present invention, wherein, in the first ligand L a , ring A and ring D are each independently selected from an aromatic ring having 6 - 18 carbon atoms or a heteroaromatic ring having 3 - 18 carbon atoms; ring B is selected from a heteroaromatic ring having 2 - 18 carbon atoms.
[0106] According to an embodiment of the present invention, ring A and ring D are each independently selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, a furan ring, a thiophene ring, an isoxazole ring, an isothiazole ring, a pyrrole ring, a pyrazole ring, a benzofuran ring, a benzothiophene ring, an azabenzofuran ring, or an azabenzothiophene ring; ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring, or an azaindole ring.
[0107] According to an embodiment of the present invention, ring A and ring D are each independently selected from a benzene ring, a naphthalene ring, a pyridine ring, or a pyrimidine ring; ring B is selected from a pyrrole ring, an indole ring, or an azaindole ring.
[0108] According to an embodiment of the present invention, ring B is a fused heteroaromatic ring.
[0109] According to an embodiment of the present invention, wherein, the first ligand L a is selected from the structures represented by any one of Formula 1 - 1 to Formula 1 - 8:
[0110]
[0111] wherein, Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
[0112] W is the same as or different from each occurrence and is selected from B, N or P;
[0113] A1 - A5 is the same as or different from each occurrence and is selected from N or CR A ;
[0114] B1 - B4 is the same as or different from each occurrence and is selected from N or CR B ;
[0115] D1 - D4 is the same as or different from each occurrence and is selected from N or CR D ;
[0116] Z3 is the same as or different from each occurrence and is selected from O, S, Se, NR Z , CR Z R Z , SiR Z R Z or PR Z ; When there are multiple Rs present simultaneously Z the multiple Rs Z are the same as or different from each other;
[0117] R A 、R B 、R D and R Z is the same as or different from each occurrence and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0118] Each occurrence of R is the same as or different from and is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0119] Adjacent substituents R A 、R B 、R D and R Z can optionally be linked to form a ring.
[0120] In this example, adjacent substituents R A 、R B 、R D and R Z can optionally be linked to form a ring, which is intended to represent groups of adjacent substituents. For example, between adjacent substituents R A 、between adjacent substituents R B 、between adjacent substituents R D 、between adjacent substituents R Z 、between adjacent substituents R A and R B 、between adjacent substituents R A and R D 、between adjacent substituents R A and R Z 、between adjacent substituents R D and R Z 、and between adjacent substituents R B and R Z Among these, any one or more of these groups of substituents can be linked to form a ring. Obviously, these groups of adjacent substituents can also not be linked to form a ring.
[0121] According to one embodiment of the present invention, the first ligand L a is selected from the structures represented by Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5 or Formula 1-6.
[0122] According to one embodiment of the present invention, the first ligand L a is selected from the structures represented by Formula 1-1, Formula 1-2 or Formula 1-3.
[0123] According to one embodiment of the present invention, wherein in the first ligand L a each occurrence of R is the same or different and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, and combinations thereof.
[0124] According to one embodiment of the present invention, each occurrence of R is the same or different and is selected from the group consisting of: deuterium, fluorine, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, neopentyl, deuterated neopentyl, cyclopentyl, deuterated cyclopentyl, and combinations thereof.
[0125] According to one embodiment of the present invention, each occurrence of R is the same or different and is selected from fluorine, methyl, or deuterated methyl.
[0126] According to one embodiment of the present invention, wherein W is selected from B or N.
[0127] According to one embodiment of the present invention, wherein W is N.
[0128] According to one embodiment of the present invention, in Formulas 1-1 to 1-3 and Formulas 1-5 to 1-8, Z1 is N, and at least one of D1 and D2 is N.
[0129] According to one embodiment of the present invention, in Formulas 1-1 to 1-3 and Formulas 1-5 to 1-8, Z1 is N and D2 is N.
[0130] According to one embodiment of the present invention, wherein in Formulas 1-1 to 1-8, A1 - A5 are each independently selected from CR A , B1 - B4 are each independently selected from CR B , D1 - D4 are each independently selected from CR D ; the R A , R B and R DEach occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0131] Adjacent substituents R A 、R B and R D can optionally be linked to form a ring.
[0132] In this embodiment, adjacent substituents R A 、R B and R D can optionally be linked to form a ring, which is intended to represent adjacent substituent groups among them. For example, between adjacent substituents R A , between adjacent substituents R B , between adjacent substituents R D , between adjacent substituents R A and R B , and between adjacent substituents R A and R D , any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring.
[0133] According to an embodiment of the present invention, in Formulas 1-1 to 1-8, A1-A5 are each independently selected from CR A , B1-B4 are each independently selected from CR B , D1-D4 are each independently selected from CR D ; the R A , R B and R DEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, and combinations thereof.
[0134] According to one embodiment of the present invention, wherein, in Formulas 1-1 to 1-8, A1-A5 are each independently selected from CR A , B1-B4 are each independently selected from CR B , D1-D4 are each independently selected from CR D ; said R A , R B and R D Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, cyano, and combinations thereof.
[0135] According to one embodiment of the present invention, wherein, in Formulas 1-1 to 1-8, at least one of A1-A n is the same or different each occurrence and is selected from CR A , said A n corresponding to the largest serial number among those where A1-A5 exist in any one of Formulas 1-1 to 1-8; and said R AEach occurrence is the same as or different from and is selected from the group consisting of deuterium, a halogen, a cyano group, a hydroxyl group, a mercapto group, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl group having 7-30 carbon atoms, a substituted or unsubstituted alkoxy group having 1-20 carbon atoms, a substituted or unsubstituted aryloxy group having 6-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3-20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6-20 carbon atoms, a substituted or unsubstituted amino group having 0-20 carbon atoms, and combinations thereof;
[0136] Adjacent substituents R A can optionally be joined to form a ring.
[0137] As used herein, adjacent substituents R A can optionally be joined to form a ring, which is intended to mean that any adjacent substituents R A can be joined to form a ring. Obviously, any adjacent substituents R A can also not be joined to form a ring.
[0138] In this embodiment, in the formulas 1-1 to 1-8, at least one of A1-A n is the same as or different from and is selected from CR A each occurrence, where A n corresponds to the largest serial number among those of A1-A5 present in any one of the formulas 1-1 to 1-8. For example, for the formula 1-1, A n corresponds to the largest serial number A3 among those of A1-A5 present in the formula 1-1. That is, in the formula 1-1, at least one of A1-A3 is the same as or different from and is selected from CR A each occurrence; for another example, for the formula 1-2, A n corresponds to the largest serial number A5 among those of A1-A5 present in the formula 1-2. That is, in the formula 1-2, at least one of A1-A5 is the same as or different from and is selected from CR A each occurrence; for still another example, for the formula 1-7, A n corresponds to the largest serial number A1 among those of A1-A5 present in the formula 1-7. That is, in the formula 1-7, A1 is the same as or different from and is selected from CR A each occurrence.
[0139] According to one embodiment of the present invention, in Formulas 1-1 to 1-6, at least one of A1 - A3 is the same or different each time it appears and is selected from CR A ; in Formulas 1-7 and 1-8, A1 is selected from CR A ; and said R A is the same or different each time it appears and is selected from the group consisting of deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, and combinations thereof.
[0140] According to one embodiment of the present invention, in Formulas 1-1, 1-4, 1-5, and 1-6, A2 is selected from CR A ; in Formula 1-2, A3 is selected from CR A ; in Formula 1-3, A2 or A3 is selected from CR A ; in Formulas 1-7 and 1-8, A1 is selected from CR A ; and said R AEach occurrence is the same or different and is selected from the group consisting of deuterium, a halogen, a cyano group, a hydroxyl group, a mercapto group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, and combinations thereof.
[0141] According to one embodiment of the present invention, the R A Each occurrence is the same or different and is selected from the group consisting of deuterium, fluorine, a cyano group, a hydroxyl group, a mercapto group, an amino group, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a neopentyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, a trimethylsilyl group, a triethylsilyl group, a phenyldimethylsilyl group, a trimethylgermyl group, a triethylgermyl group, a phenyl group, a 2,6-dimethylphenyl group, a 2,6-diisopropylphenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, and combinations thereof.
[0142] According to one embodiment of the present invention, in Formulas 1-1 to 1-8, at least one of B1-B n is selected from CR B , and the B n corresponds to the largest serial number among the serial numbers where B1-B4 exist in any one of Formulas 1-1 to 1-8; and / or, in Formulas 1-1 to 1-8, at least one of D1-D n is selected from CR D , and the D n corresponds to the largest serial number among the serial numbers where D1-D4 exist in any one of Formulas 1-1 to 1-8; the R B , R DEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, and combinations thereof.
[0143] In this embodiment, in the formulas 1-1 to 1-8, at least one of B1-B n is the same or different each occurrence and is selected from CR B , and the B n corresponds to the largest serial number among those where B1-B4 exist in any one of the formulas 1-1 to 1-8. For example, for formula 1-1, the B n corresponds to the largest serial number among those where B1-B4 exist in formula 1-1, which is B4. That is, in formula 1-1, at least one of B1-B4 is the same or different each occurrence and is selected from CR B ; again, for example, for formula 1-5, the B n corresponds to the largest serial number among those where B1-B4 exist in formula 1-5, which is B2. That is, in formula 1-5, at least one of B1-B2 is the same or different each occurrence and is selected from CR B .
[0144] In this embodiment, in the formulas 1-1 to 1-8, at least one of D1-D n is the same or different each occurrence and is selected from CR D , and the D n corresponds to the largest serial number among those where D1-D4 exist in any one of the formulas 1-1 to 1-8. For example, for formula 1-1, the D n corresponds to the largest serial number among those where D1-D4 exist in formula 1-1, which is D2. That is, in formula 1-1, at least one of D1-D2 is the same or different each occurrence and is selected from CR D ; again, for example, for formula 1-4, the D nCorresponding to the largest serial number D4 among D1 - D4 existing in Formulas 1 - 4, that is, in Formulas 1 - 4, at least one of D1 - D4 is the same or different and is selected from CR each time it appears D 。
[0145] According to an embodiment of the present invention, in Formulas 1 - 1 to 1 - 4, Formulas 1 - 6 to 1 - 8, B2 and / or B3 are selected from CR B ; in Formula 1 - 5, B1 and / or B2 are selected from CR B ; in the above - mentioned Formulas 1 - 1 to 1 - 8, D1 and / or D2 are selected from CR D ; the R B 、R D each time it appears is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, and combinations thereof.
[0146] According to an embodiment of the present invention, in Formulas 1 - 1 to 1 - 4, Formulas 1 - 6 to 1 - 8, B2 and / or B3 are selected from CR B ; in Formula 1 - 5, B1 and / or B2 are selected from CR B ; in the above - mentioned Formulas 1 - 1 to 1 - 8, D1 and / or D2 are selected from CR D ; the R B 、R D each time it appears is the same or different and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, amino, methyl, ethyl, isopropyl, isobutyl, tert - butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert - butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
[0147] According to an embodiment of the present invention, wherein, in Formulas 1 - 5 and 1 - 8, Z3 each time it appears is the same or different and is selected from O, S or Se.
[0148] According to an embodiment of the present invention, in Formula 1-5 and Formula 1-8, Z3 is the same or different each time it appears and is selected from O or S.
[0149] According to an embodiment of the present invention, wherein the first ligand L a is the same or different each time it appears and is selected from the group consisting of L a1 to L a632 ; the specific structures of L a1 to L a632 are shown in Claim 10.
[0150] According to an embodiment of the present invention, wherein in the structure of L a1 to L a632 , part or all of the hydrogen atoms can be replaced by deuterium.
[0151] According to an embodiment of the present invention, wherein the second ligand L b has a structure represented by Formula 2-1:
[0152]
[0153] Wherein, R1-R8 are the same or different each time they appear and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0154] And at least one of R1-R4 is selected from fluorine;
[0155] Adjacent substituents R1-R8 can optionally be connected to form a ring.
[0156] In this text, adjacent substituents R1 - R8 can optionally be connected to form a ring, which is intended to represent groups of adjacent substituents, such as adjacent substituents R1 and R2, adjacent substituents R2 and R3, adjacent substituents R3 and R4, adjacent substituents R4 and R5, adjacent substituents R5 and R6, adjacent substituents R6 and R7, and adjacent substituents R7 and R8. Any one or more of these groups of adjacent substituents can be connected to form a ring. Obviously, none of these groups of adjacent substituents may also be connected to form a ring.
[0157] According to one embodiment of the present invention, each occurrence of R1 - R8 is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof; and at least one of R1 - R4 is selected from fluorine.
[0158] According to one embodiment of the present invention, at least one or two of R1 - R8 each occurrence is the same or different and is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or combinations thereof; and at least one of R1 - R4 is selected from fluorine.
[0159] According to one embodiment of the present invention, wherein the second ligand L b is selected from the structures represented by any one of Formula 2 - 2 to Formula 2 - 5:
[0160]
[0161] Wherein, each occurrence of R1-R8 is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0162] Adjacent substituents R1-R8 can optionally be joined to form a ring.
[0163] According to one embodiment of the present invention, each occurrence of R1-R8 is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0164] According to one embodiment of the present invention, at least one or two of R1-R8 each occurrence is the same as or different from each other and is selected from deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, or combinations thereof.
[0165] According to one embodiment of the present invention, in Formula 2-2 and Formula 2-5, at least one or at least two or at least three or all of R2, R3, R6, R7 each occurrence is the same as or different from each other and is selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0166] According to one embodiment of the present invention, in Formula 2-2 and Formula 2-5, at least one or at least two or at least three or all of R2, R3, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.
[0167] According to one embodiment of the present invention, in Formula 2-2 and Formula 2-5, at least one or at least two or at least three or all of R2, R3, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and a partially or fully deuterated one of the foregoing groups.
[0168] According to one embodiment of the present invention, in Formula 2-3, at least one or at least two or all of R3, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
[0169] According to one embodiment of the present invention, in Formula 2-3, at least one or at least two or all of R3, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.
[0170] According to one embodiment of the present invention, in Formula 2-3, at least one or at least two or all of R3, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and a partially or fully deuterated one of the foregoing groups.
[0171] According to one embodiment of the present invention, in Formula 2-4, at least one or at least two or all of R2, R6, and R7 are each independently selected, each time they appear, from the group consisting of deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
[0172] According to one embodiment of the present invention, in Formula 2-4, at least one, at least two, or all of R2, R6, and R7 are each independently selected, each time they appear, from the group consisting of: deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof.
[0173] According to one embodiment of the present invention, in Formula 2-4, at least one, at least two, or all of R2, R6, and R7 are each independently selected, each time they appear, from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and a partially or fully deuterated one of the foregoing groups.
[0174] According to one embodiment of the present invention, wherein the second ligand L b is each independently selected, each time it appears, from the group consisting of L b1 to L b433 ; the specific structures of L b1 to L b433 are shown in claim 12.
[0175] According to one embodiment of the present invention, wherein the hydrogen in the structure of L b1 to L b433 can be partially or completely replaced by deuterium.
[0176] According to one embodiment of the present invention, wherein the third ligand L c is each independently selected, each time it appears, from the group consisting of the following structures:
[0177]
[0178] wherein R a , R b , and R c are each independently selected, each time they appear, to represent mono-substitution, multi-substitution, or no substitution;
[0179] X b is each independently selected, each time it appears, from the group consisting of: O, S, Se, NR N1 , and CR C1 R C2 ;
[0180] R a , R b , R c , R N1 , R C1 , and R C2The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0181] Adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 Can optionally be linked to form a ring.
[0182] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 can be optionally connected to form a ring, and is intended to indicate that in the L c Adjacent substituent groups in the structure of a Between adjacent substituents R b Between adjacent substituents R c Between adjacent substituents R a With R b Between adjacent substituents R b With R c Between adjacent substituents R a With R c Between adjacent substituents R a With R N1 Between adjacent substituents R a With R C1 Between adjacent substituents Ra Between R C2 and adjacent substituents R b and R N1 and adjacent substituents R c and R N1 and adjacent substituents R b and R C1 and adjacent substituents R b and R C2 and adjacent substituents R c and R C1 and adjacent substituents R c and R C2 and adjacent substituents R C1 and R C2 and any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may also not be connected to form a ring at all. For example, adjacent substituents R a , R b can optionally be connected to form a ring, which can form one or more of the following structures including but not limited to: wherein T is selected from O, S, Se, NR' or CR'R'; wherein said R', R a ', R b ' has the same definition as said R a . Obviously, these substituents may also not be connected to form a ring.
[0183] According to one embodiment of the present invention, wherein said third ligand L c is the same or different each time it appears and is selected from the group consisting of L c1 to L c329 ; for the specific structures of said L c1 to L c329 see claim 13.
[0184] According to one embodiment of the present invention, wherein the hydrogen in the structure of said L c1 to L c329 can be partially or completely replaced by deuterium.
[0185] According to one embodiment of the present invention, wherein said metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
[0186] According to one embodiment of the present invention, wherein said metal M is selected from Ir, Pt or Os.
[0187] According to an embodiment of the present invention, wherein the metal M is Ir.
[0188] According to an embodiment of the present invention, wherein the metal complex has the general formula Ir(L a ) m (L b ) 3-m and has a structure represented by
[0189] Formula 3:
[0190]
[0191] wherein m is 1 or 2;
[0192] Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
[0193] W is the same or different each time it appears and is selected from B, N or P;
[0194] R is the same or different each time it appears and is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, and combinations thereof;
[0195] A1 - A3 are the same or different each time they appear and are selected from N or CR A ;
[0196] B1 - B4 are the same or different each time they appear and are selected from N or CR B ;
[0197] D1 - D2 are the same or different each time they appear and are selected from N or CR D ;
[0198] U1 - U4 are the same or different each time they appear and are selected from N or CR U ;
[0199] W1 - W4 are the same or different each time they appear and are selected from N or CR W ;
[0200] R A 、R B 、R D 、R U and RW Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0201] and R W at least one of which is selected from fluorine;
[0202] Adjacent substituents R A 、R B 、R D can optionally be joined to form a ring;
[0203] Adjacent substituents R U 、R W can optionally be joined to form a ring.
[0204] According to one embodiment of the present invention, each occurrence of said R is the same or different and is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms; at least one of A1 - A3 is selected from CR A , and / or at least one of B1 - B4 is selected from CR B , and said R A , R BEach occurrence is the same as or different from and is selected from the group consisting of: deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a mercapto group, and combinations thereof.
[0205] According to one embodiment of the present invention, A2 is selected from CR A , and / or one of B2 and B3 is selected from CR B ; and said R A , R B Each occurrence is the same as or different from and is selected from the group consisting of: deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a mercapto group, and combinations thereof.
[0206] According to one embodiment of the present invention, each occurrence of said R is the same as or different from and is selected from the group consisting of: deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclopentyl; said R A , R BEach occurrence is the same or different and is selected from the group consisting of: deuterium, fluorine, cyano, hydroxy, mercapto, amino, methoxy, phenoxy, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuryl, tetrahydropyranyl, tetrahydrothienyl, piperidinyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermyl, triethylgermyl, phenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, pyridyl, pyrimidinyl, triazinyl, and combinations thereof.
[0207] According to one embodiment of the present invention, wherein the metal complex has the structure of Ir(L a )(L b )2 or Ir(L a )2(L b ) or Ir(L a )(L b )(L c );
[0208] Wherein, when the metal complex has the structure of Ir(L a )(L b )2, the L a is selected from any one of the group consisting of L a1 to L a632 , and the L b is the same or different each occurrence and is selected from any one or two of the group consisting of L b1 to L b433 ; when the metal complex has the structure of Ir(L a )2(L b ), the L a is the same or different each occurrence and is selected from any one or any two of the group consisting of L a1 to L a632 , and the L b is selected from any one of the group consisting of L b1 to L b433 ; when the metal complex has the structure of Ir(L a )(L b )(L c ), the L a is selected from any one of the group consisting of L a1 to L a632 , the L b is selected from any one of the group consisting of L b1 to L b433 , and the L c is selected from the group consisting of Lc1 to L c329 any one of the groups consisting of; optionally, the hydrogen atoms in the structure of the metal complex can be partially or fully replaced by deuterium.
[0209] According to an embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 1204; for the specific structures of Compound 1 to Compound 1204, see Claim 16.
[0210] According to an embodiment of the present invention, the hydrogen in the structures of Compound 1 to Compound 1204 can be partially or fully replaced by deuterium.
[0211] According to an embodiment of the present invention, an electroluminescent device is also disclosed, which includes:
[0212] an anode,
[0213] a cathode,
[0214] and an organic layer disposed between the anode and the cathode, the organic layer containing a metal complex, and the specific structure of the metal complex being as shown in any of the foregoing embodiments.
[0215] According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.
[0216] According to an embodiment of the present invention, the electroluminescent device emits orange-red light.
[0217] According to an embodiment of the present invention, the electroluminescent device emits white light.
[0218] According to an embodiment of the present invention, wherein the maximum emission wavelength of the photoluminescence spectrum of the metal complex is between 580 nm and 595 nm.
[0219] According to an embodiment of the present invention, in the electroluminescent device, the light-emitting layer further includes at least one host material.
[0220] According to an embodiment of the present invention, the at least one host material contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0221] According to an embodiment of the present invention, in the electroluminescent device, the light-emitting layer further includes a first host material and a second host material.
[0222] According to one embodiment of the present invention, the first host material has a structure represented by Formula 4-1, Formula 4-2, or Formula 4-3:
[0223]
[0224] wherein X1 is the same or different each occurrence and is selected from CR x or N;
[0225] X2 is the same or different each occurrence and is selected from C, CR x or N;
[0226] L is the same or different each occurrence and is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
[0227] Ar 21 Ar 22 Ar 31 Ar 32 Ar 33 is the same or different each occurrence and is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
[0228] R x is the same or different each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0229] Adjacent substituents R x can optionally be joined to form a ring.
[0230] In this text, adjacent substituents R x can optionally be linked to form a ring, which is intended to represent a group of adjacent substituents. For example, adjacent substituents R x can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring at all.
[0231] According to an embodiment of the present invention, wherein the second host material has a structure represented by Formula 4-1-1, 4-2-1 or Formula 4-3-1:
[0232]
[0233] wherein X1, X2, X3 are each independently the same or different and are selected from CR x or N;
[0234] Ar 21 , Ar 22 , Ar 32 , Ar 33 are each independently the same or different and are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0235] L is each independently the same or different and is selected from a single bond, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof;
[0236] R xEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0237] Adjacent substituents R x Can optionally be linked to form a ring.
[0238] According to one embodiment of the present invention, wherein the first host material is selected from the group consisting of Compound 1-1-1 to Compound 1-1-104, Compound 1-2-1 to Compound 1-2-100, and Compound 1-3-1 to Compound 1-3-62:
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259] According to an embodiment of the present invention, in the compounds 1-1-1 to 1-1-104, compounds 1-2-1 to 1-2-100, and compounds 1-3-1 to 1-3-62, the hydrogen can be partially or completely replaced by deuterium.
[0260] According to an embodiment of the present invention, the second host material has a structure represented by Formula 5:
[0261]
[0262] Wherein, each occurrence of L1 to L3 is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;
[0263] Each occurrence of Ar1 to Ar3 is the same or different and is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof.
[0264] According to an embodiment of the present invention, the second host material has a structure represented by Formula 5-1 or Formula 5-2:
[0265]
[0266] Wherein, in Formula 5-1, each occurrence of V1 to V5 is the same or different and is selected from C, N or CRv and V 11 to V 15 is independently selected from N or CR each time it appears v1 and one of V1 to V5 is C and is linked to L 43 ;
[0267] In Formula 5-2, V1 to V4 is independently selected from C, N or CR each time it appears v and V 11 to V 14 is independently selected from N or CR each time it appears v1 and one of V1 to V4 is C and is linked to L 43 ;
[0268] V is selected from O, S or Se;
[0269] L 41 to L 43 is independently selected from a single bond, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof each time it appears
[0270] Ar 41 and Ar 42 is independently selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof each time it appears
[0271] R v and R v1Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0272] Adjacent substituents R v , R v1 can optionally be joined to form a ring.
[0273] As used herein, adjacent substituents R v , R v1 can optionally be joined to form a ring, which is intended to mean that among adjacent substituent groups, for example, among adjacent substituents R v , among adjacent substituents R v1 , and among adjacent substituents R v and R v1 , any one or more of these substituent groups can be joined to form a ring. Obviously, these substituents may also not be joined to form a ring.
[0274] According to one embodiment of the present invention, wherein at least one of said Ar 41 and Ar 42 is a fused ring structure of two or three rings.
[0275] According to one embodiment of the present invention, wherein said Ar 41 and Ar 42 are each the same as or different from and are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted a radical, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted indolocarbazolyl group, or a combination thereof.
[0276] According to one embodiment of the present invention, wherein, in the third compound, L 41 to L 43 each occurrence is the same or different and is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
[0277] According to one embodiment of the present invention, wherein the second host material is selected from the group consisting of Compound B-1 to Compound B-227:
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290]
[0291]
[0292]
[0293]
[0294]
[0295]
[0296]
[0297] According to one embodiment of the present invention, in which, the hydrogen in the compounds B-1 to B-227 can be partially or completely replaced by deuterium.
[0298] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises a metal complex, and the specific structure of the metal complex is as shown in any one of the foregoing embodiments.
[0299] Combined with other materials
[0300] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132-0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0301] The materials described herein as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the devices. For example, the compounds disclosed herein can be combined with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080-0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0302] In the examples of material synthesis, unless otherwise specified, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized products were subjected to structure confirmation and property testing using one or more conventional devices in the art (including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters from Shimadzu, fluorescence spectrophotometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc.) by methods well-known to those skilled in the art. In the examples of devices, the properties of the devices were also tested using conventional devices in the art (including but not limited to evaporation coaters produced by Angstrom Engineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc.) by methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and testing methods and can obtain the inherent data of the samples determinately and without being affected, the above relevant content will not be elaborated further in this patent.
[0303] There is no limitation on the preparation method of the electroluminescent device. The preparation methods in the following examples are only examples and should not be construed as limitations. Those skilled in the art can reasonably improve the preparation methods in the following examples based on the prior art. Exemplarily, the ratios of various materials in the light-emitting layer are not particularly limited, and those skilled in the art can reasonably select within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer materials, the host material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the host material can account for 90%-99%, and the light-emitting material can account for 1%-10%; or the host material can account for 95%-99%, and the light-emitting material can account for 1%-5%. In addition, the host material can be one or two materials, and the ratio of the two host materials to the host material can be 99:1 to 1:99; or the ratio can be 80:20 to 20:80; or the ratio can be 60:40 to 40:60; or the ratio can be 50:50.
[0304] Examples of material synthesis:
[0305] There is no limitation on the preparation method of the compounds of the present invention. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:
[0306] Synthesis Example 1: Synthesis of Compound 62
[0307]
[0308] Iridium complex I (1.4 g, 1.8 mmol) and intermediate A (1.0 g, 2.7 mmol) were added to a 250 mL three-necked flask, and a mixed solvent of ethoxyethanol (50 mL) and N,N-dimethylformamide (50 mL) was added. Under nitrogen protection, the reaction was carried out at 100 °C for 120 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and purified by column chromatography, eluting with petroleum ether:dichloromethane (3:1, v / v) to obtain product compound 62 (200 mg, yield 11.4%). The product was confirmed to be the target product with a molecular weight of 968.32.
[0309] Synthesis Example 2: Synthesis of Compound 119
[0310]
[0311] Iridium complex II (1.4 g, 1.8 mmol) and intermediate A (1.0 g, 2.7 mmol) were added to a 500 mL three-necked flask, and a mixed solvent of ethoxyethanol (50 mL) and N,N-dimethylformamide (50 mL) was added. Under nitrogen protection, the reaction was carried out at 100 °C for 120 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and purified by column chromatography, eluting with petroleum ether:dichloromethane (2:1, v / v) to obtain product compound 119 (220 mg, yield 13.4%). The product was confirmed to be the target product with a molecular weight of 946.33.
[0312] Synthesis Example 3: Synthesis of Compound 178
[0313]
[0314] Iridium complex III (1.6 g, 1.8 mmol) and intermediate A (1.0 g, 2.7 mmol) were added to a 250 mL three-necked flask, and a mixed solvent of ethoxyethanol (50 mL) and N,N-dimethylformamide (50 mL) was added. Under nitrogen protection, the reaction was carried out at 100 °C for 120 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and purified by column chromatography, eluting with petroleum ether:dichloromethane (2:1, v / v) to obtain product compound 178 (200 mg, yield 10.9%). The product was confirmed to be the target product with a molecular weight of 1024.39.
[0315] Synthesis Example 4: Synthesis of Compound 931
[0316]
[0317] Iridium complex Ⅳ (900 mg, 1.0 mmol) and intermediate A (564 mg, 1.5 mmol) were added to a 100 mL three-necked flask, and a mixed solvent of ethoxyethanol (25 mL) and N,N-dimethylformamide (25 mL) was added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 120 hours, then cooled to room temperature. The solvent was removed by rotary evaporation and purified by column chromatography, eluting with petroleum ether:dichloromethane (2:1, v / v) to obtain product compound 931 (150 mg, yield 13.7%). The product was confirmed to be the target product with a molecular weight of 1092.52.
[0318] Synthesis Example 5: Synthesis of Compound 206
[0319]
[0320] Iridium complex Ⅲ (1.2 g, 1.4 mmol) and intermediate B (800 mg, 2.1 mmol) were added to a 250 mL three-necked flask, and a mixed solvent of ethoxyethanol (30 mL) and N,N-dimethylformamide (30 mL) was added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 120 hours, then cooled to room temperature. The solvent was removed by rotary evaporation and purified by column chromatography, eluting with petroleum ether:dichloromethane (2:1, v / v) to obtain product compound 206 (120 mg, yield 8.3%). The product was confirmed to be the target product with a molecular weight of 1028.36.
[0321] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0322] Spectral data
[0323] In the present invention, the method for measuring the photoluminescence spectrum (PL) of a compound is as follows:
[0324] The compound to be measured was formulated into a solution with a concentration of 3×10 -5 mol / L using HPLC-grade dichloromethane, and then excited with light at a wavelength of 500 nm and its emission spectrum was measured at room temperature (298 K). The spectrum was measured using a spectrophotometer model F98 produced by Shanghai Lengguang Technology Co., Ltd.
[0325] The photoluminescence spectrum (PL) data of the compounds of the present invention and the comparative compounds were measured by the above method, and the results are shown in Table 1.
[0326] Table 1 PL data of the compounds of the present invention and the comparative compounds
[0327] Compound Number <![CDATA[λ max (nm)]]> FWHM (nm) Compound 62 589 22.8 Compound 119 590 24.1 Compound 178 590 25.6 Compound 931 592 23.2 Compound 206 591 25.6 Compound RD - A 597 26.5 Compound RD - B 596 26.9 Compound RD - C 601 29.5 Compound RD - D 600 27.1
[0328] The structures of the related compounds in Table 1 are as follows:
[0329]
[0330]
[0331] From the data in Table 1, it can be seen that the compounds of the present invention have a maximum emission wavelength of about 590 nm, can meet the desired orange light emission requirements, and all have a very narrow full width at half maximum. Among them, compared with the comparative compound RD-A, the only difference between Compound 178 of the present invention and Compound 206 of the present invention lies in whether there is a substituent R at a specific position of the L a ligand. Compounds 178 and 206 of the present invention introduce a substituent R at a specific position of the L a ligand, which can significantly blue-shift the maximum emission wavelength of the compound by more than 6 nm, achieving the desired orange light emission of about 590 nm, and the full width at half maximum is narrowed by 0.9 nm; compared with the comparative compound RD-B, the only difference between Compound 178 of the present invention lies in whether there is a fluorine substitution on a specific ring of the L b ligand. Compound 178 of the present invention introduces a fluorine substituent on a specific ring of the L b ligand, achieving the desired orange light emission of 590 nm, and the full width at half maximum is narrowed by 1.3 nm; although the comparative compound RD-C introduces a substituent R at a specific position of the L a ligand, a methyl group is introduced at the ortho position of the substituent R, which causes the emission wavelength of the comparative compound RD-C to red-shift to the red light emission region of 601 nm, unable to achieve the desired orange light emission, and the full width at half maximum is relatively wide; the comparative compound RD-D does not introduce a substituent R at a specific position of the L a ligand, and at the same time, no fluorine substitution is introduced on a specific ring of the L b ligand, which causes the emission wavelength of the comparative compound RD-D to red-shift to the red light emission region of 600 nm, and the full width at half maximum is also relatively wide. The above analysis shows that the compounds of the present invention can achieve the desired saturated orange light emission by introducing a substituent R at a specific position of the L a ligand, and there is no substituent at the ortho position of the substituent R. At the same time, the design of introducing a fluorine substituent on a specific ring of the L b ligand can achieve the desired saturated orange light emission, and its full width at half maximum is also quite narrow, which is a level that most current commercial materials cannot reach. These advantages highlight the uniqueness of the present invention and the commercial application potential of the compounds of the present invention as the desired orange light emitting materials. To further verify the performance of the metal complexes of the present invention in devices, device examples using the metal complexes of the present invention as light emitting materials are provided herein.
[0332] Device Example
[0333] Device Example 1
[0334] First, a glass substrate having a 120 nm thick indium tin oxide (ITO) anode is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. Then the substrate is mounted on a substrate holder and loaded into a vacuum chamber. The following specified organic layers are sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / sec under a vacuum of about 10 -8 Torr. Compound HT and HI as a dopant are used as a hole injection layer (HIL, weight ratio 97:3), with a thickness Compound HT is used as a hole transport layer (HTL), with a thickness Compound EB is used as an electron blocking layer (EBL), with a thickness Then, Compound 62 of the present invention is doped in Compound 1 - 2 - 2 as the first host and Compound B - 227 as the second host and used as an emitting layer (EML, weight ratio 2:49:49), with a thickness Compound HB is used as a hole blocking layer (HBL), with a thickness On the HBL, Compound ET and lithium 8 - hydroxyquinoline (Liq) are co - deposited as an electron transport layer (ETL, weight ratio 40:60), with a thickness Finally, 1 nm thick Liq is deposited as an electron injection layer, and 120 nm of Al is deposited as a cathode. Then the device is transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
[0335] Device Example 2
[0336] The preparation method of Device Example 2 is the same as that of Device Example 1, except that Compound 931 of the present invention is used instead of Compound 62 in the emitting layer (EML).
[0337] Device Comparative Example 1
[0338] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that Compound RD - C is used instead of Compound 62 in the emitting layer (EML).
[0339] Device Comparative Example 2
[0340] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that Compound RD - D is used instead of Compound 62 in the emitting layer (EML).
[0341] The partial layer structure and thickness of the device are shown in the following table. For those where more than one material is used, different compounds are doped in the recorded weight ratios.
[0342] Table 2 Partial device structures of device examples and comparative examples
[0343]
[0344] The structures of the materials used in the device are as follows:
[0345]
[0346]
[0347] The IVL characteristics of the device were measured. Table 3 shows the data of CIE chromaticity coordinates, maximum emission wavelength (λ 2 ), full width at half maximum (FWHM), current efficiency (CE), and power efficiency (PE) measured at a current density of 15 mA / cm max 2.
[0348] Table 3 Device data
[0349]
[0350] Discussion:
[0351] From the data in Table 3, it can be seen that the metal complex with a specific structure of the present invention can endow the device with very excellent performance. In Examples 1 and 2, due to the use of the metal complex with a specific structure of the present invention as the luminescent material, the maximum emission wavelength can be blue-shifted to the desired orange light emission region of less than 595 nm, and it has an extremely narrow full width at half maximum of less than 23 nm, which can meet the application requirements of better desired orange light emission.
[0352] Compound RD-C used in Comparative Example 1 has 2 substituents on the benzene ring connected to the metal in the polycyclic ligand, and there is no fluorine substituent on the benzene ring connected to the metal in its phenylpyridine ligand. Compound RD-D used in Comparative Example 2 has no substituent at a specific position in the polycyclic ligand, and there is also no fluorine substituent on the benzene ring connected to the metal in its phenylpyridine ligand. However, the metal complexes used in Examples 1 - 2 of the present invention introduce substituents (there is no substituent at the ortho position of the said substituent) at specific positions in the polycyclic ligand (L a ligand), and at the same time in the phenylpyridine ligand (L bIntroducing a fluorine substituent on the benzene ring connected to the metal in the ligand can shift the maximum emission wavelength of the device to less than 595 nm and narrow the full width at half maximum by more than 5 nm, enabling extremely high-saturation desired orange light emission. At the same time, the device efficiencies of Example 1 and Example 2 are further improved. Specifically, compared with Comparative Example 1, the current efficiency and power efficiency of Example 1 are significantly increased by 10.9% and 11.0% respectively, and the current efficiency and power efficiency of Example 2 are significantly increased by 31.6% and 26.8% respectively; compared with Comparative Example 2, the current efficiency and power efficiency of Example 1 are significantly increased by 18.8% and 24.1% respectively, and the current efficiency and power efficiency of Example 2 are significantly increased by 41.0% and 41.8% respectively. This shows that the metal complex with a specific structure of the present invention has very excellent properties.
[0353] In summary, the metal complex with a specific structure of the present invention can meet the requirements of the desired orange light emission, can unexpectedly narrow the full width at half maximum significantly, and can achieve high-saturation light emission; moreover, when the metal complex of the present invention is used as a light-emitting material in an electroluminescent device, it can endow the device with the advantages of high current efficiency and high power efficiency, and can provide more excellent device performance. This proves the excellent properties and broad application prospects of the metal complex with a specific structure of the present invention.
[0354] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims
1. A metal complex having the general formula M(L a ) m (L b ) n (L c ) q , where The metal M is selected from metals with a relative atomic mass greater than 40, L a , L b and L c are the first ligand, the second ligand, and the third ligand coordinated with the metal M, respectively; L a ,L b and L c can optionally be linked to form a polydentate ligand; m is selected from 1 or 2, n is selected from 1 or 2, q is selected from 0 or 1, and m + n + q is equal to the oxidation state of metal M; when m is equal to 2, two Ls a are the same or different; when n is equal to 2, two Ls b are the same or different; The first ligand L a has a structure represented by Formula 1: Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different; W is the same or different each time it appears and is selected from B, N or P; R is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ring A and ring D are the same or different each time they appear and are selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms or a heteroaromatic ring having 3-30 carbon atoms; Ring B is selected from a heterocyclic ring having 2-30 carbon atoms or a heteroaromatic ring having 2-30 carbon atoms; R A , R B and R D each time it appears, independently represents mono-substitution, multi-substitution or no substitution; R A 、R B and R D are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R A 、R B and R D can optionally be linked to form a ring; The second ligand L b has a structure represented by Formula 2: U1 - U4 are each independently selected from N or CR, either the same or different, each time they appear U ; W1 - W4, each time they appear, are the same as or different from each other and are selected from N or CR W ; R U 、R W each occurrence of which is the same as or different from one another and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and R W at least one of which is selected from fluorine; Adjacent substituents R U and R W may optionally be linked to form a ring; The third ligand L c is selected from monoanionic bidentate ligands.
2. The metal complex according to claim 1, wherein The first ligand L a wherein each occurrence of ring A and ring D is independently selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; ring B is selected from a heteroaromatic ring having 2 to 18 carbon atoms; Preferably, ring A and ring D are the same or different each time they appear and are selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, a furan ring, a thiophene ring, an isoxazole ring, an isothiazole ring, a pyrrole ring, a pyrazole ring, a benzofuran ring, a benzothiophene ring, an azabenzofuran ring, or an azabenzothiophene ring; ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring, or an azaindole ring; More preferably, ring A and ring D are the same or different each time they appear and are selected from a benzene ring, a naphthalene ring, a pyridine ring, or a pyrimidine ring; ring B is selected from a pyrrole ring, an indole ring, or an azaindole ring.
3. The metal complex according to claim 1, wherein The first ligand L a is selected from the structures represented by any one of Formula 1-1 to Formula 1-8: Wherein, Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different; W is the same or different each time it appears and is selected from B, N or P; A1 - A5 are each, independently upon each occurrence, selected from N or CR A ; B1 - B4 are each independently selected from N or CR, the same or different each time they appear B ; D1 - D4 are the same as or different from each other each time they appear, and are selected from N or CR D ; Z3 is the same as or different from each other each time it appears and is selected from O, S, Se, NR Z , CR Z R Z , SiR Z R Z or PR Z ; when there are multiple R Z at the same time, the multiple R Z are the same as or different from each other; R A 、R B 、R D and R Z are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Each occurrence of R is the same as or different from each other and is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, a substituted or unsubstituted amino having 0 - 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R A 、R B 、R D and R Z may optionally be linked to form a ring; Preferably, L a is selected from the structures represented by Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5 or Formula 1-6; More preferably, L a is selected from the structures represented by Formula 1-1, Formula 1-2 or Formula 1-3.
4. The metal complex according to claim 1 or 3, wherein, The first ligand L a wherein each occurrence of R is the same or different and is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; Preferably, each occurrence of R is the same as or different from each other and is selected from the group consisting of deuterium, fluorine, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert - butyl, deuterated tert - butyl, neopentyl, deuterated neopentyl, cyclopentyl, deuterated cyclopentyl, and combinations thereof; More preferably, each occurrence of R is the same as or different from each other and is selected from fluorine, methyl, or deuterated methyl.
5. The metal complex according to claim 1 or 3, wherein, W is selected from B or N; preferably, W is N.
6. The metal complex according to claim 3, wherein, In Formulas 1 - 1 to 1 - 3 and Formulas 1 - 5 to 1 - 8, Z1 is N, and at least one of D1 and D2 is N; Preferably, in Formulas 1 - 1 to 1 - 3 and Formulas 1 - 5 to 1 - 8, Z1 is N and D2 is N.
7. The metal complex according to claim 3, wherein, In Formulas 1-1 to 1-8, each of A1 - A5 is independently selected from CR A , each of B1 - B4 is independently selected from CR B , each of D1 - D4 is independently selected from CR D ; said R A , R B and R D are the same or different each time they appear and are independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R A 、R B and R D can optionally be linked to form a ring; Preferably, the R A , R B and R D are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, and combinations thereof; More preferably, said R A , R B and R D are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, cyano, and combinations thereof.
8. The metal complex according to claim 3, wherein, In Formulas 1-1 to 1-8, each occurrence of at least one of A1-A n is the same as or different from each other and is independently selected from CR A , where the A n corresponds to the largest serial number among those where A1-A5 exist in any one of Formulas 1-1 to 1-8; and each occurrence of the R A is the same as or different from each other and is independently selected from the group consisting of deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, and combinations thereof; Adjacent substituents R A can optionally be linked to form a ring; Preferably, in Formulae 1-1 to 1-6, at least one of A1 - A3 is the same or different and is independently selected from CR each time it appears A ; in Formulae 1-7 and 1-8, A1 is selected from CR A ; More preferably, in Formula 1-1, Formula 1-4, Formula 1-5, and Formula 1-6, A2 is selected from CR A ; in Formula 1-2, A3 is selected from CR A ; in Formula 1-3, A2 or A3 is selected from CR A ; in Formula 1-7 and Formula 1-8, A1 is selected from CR A ; Most preferably, said R A is the same or different each time it appears and is selected from the group consisting of deuterium, fluorine, cyano, hydroxy, mercapto, amino, methyl, ethyl, isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermyl, triethylgermyl, phenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, pyridyl, pyrimidyl, triazinyl, and combinations thereof.
9. The metal complex according to claim 3, wherein, In Formulas 1-1 to 1-8, at least one of B1-B n is selected from CR B , and the B n corresponds to the largest serial number among those where B1-B4 exist in any one of Formulas 1-1 to 1-8; and / or, in Formulas 1-1 to 1-8, at least one of D1-D n is selected from CR D , and the D n corresponds to the largest serial number among those where D1-D4 exist in any one of Formulas 1-1 to 1-8; the R B , R D is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, and combinations thereof; Preferably, in Formula 1-1 to Formula 1-4, Formula 1-6 to Formula 1-8, B2 and / or B3 are selected from CR B ; in Formula 1-5, B1 and / or B2 are selected from CR B ; in the said Formula 1-1 to Formula 1-8, D1 and / or D2 are selected from CR D ; More preferably, said R B , R D is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, amino, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, triethylsilyl, trimethylgermyl, triethylgermyl, phenyl, pyridyl, triazinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, and combinations thereof.
10. The metal complex according to claim 1, wherein, The first ligand L a is the same or different each time it appears and is selected from the group consisting of the following structures: In the structure, TMS represents trimethylsilyl; Optionally, the hydrogen in the structure of L a1 to L a632 is partially or completely replaced by deuterium.
11. The metal complex according to claim 1 or 10, wherein, The second ligand L b has a structure represented by Formula 2-1: Wherein, each occurrence of R1 - R8 is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; And at least one of R1 - R4 is selected from F; Adjacent substituents R1 - R8 can optionally be joined to form a ring; Preferably, each occurrence of R1 - R8 is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, and combinations thereof; and at least one of R1 - R4 is selected from F; More preferably, at least one or two of R1 - R8, each occurrence being the same as or different from each other, are selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or combinations thereof; and At least one of R1 - R4 is selected from F.
12. The metal complex according to claim 11, wherein, The second ligand L b is the same or different each time it appears and is selected from the group consisting of: Optionally, the hydrogen in the ligand L b1 to L b433 structure may be partially or fully substituted with deuterium.
13. The metal complex according to claim 12, wherein, The third ligand L c is the same as or different from each other every time it appears and is selected from the group consisting of the following structures: wherein, R a , R b and R c each independently represents, when occurring each time, mono-substitution, poly-substitution, or no substitution; X b is the same as or different from each occurrence and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; R a 、R b 、R c 、R N1 、R C1 and R C2 each occur the same or different and are independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R a 、R b 、R c 、R N1 、R C1 and R C2 can optionally be linked to form a ring; Preferably, the third ligand L c is the same or different each time it appears and is selected from the group consisting of the following structures: Optionally, the hydrogen in the ligand L c1 to L c329 in the structure may be partially or fully replaced by deuterium.
14. The metal complex according to claim 1, wherein, The metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; preferably, the metal M is selected from Ir, Pt or Os; more preferably, the metal M is Ir.
15. The metal complex according to claim 1, wherein, The metal complex has the general formula of Ir(L a ) m (L b ) 3-m and has a structure represented by Formula 3: Wherein, m is 1 or 2; Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different; Each occurrence of W is the same as or different from each other and is selected from B, N or P; Each occurrence of R is the same or different and is selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, and combinations thereof; A1 - A3, each occurrence independently and identically or differently, is selected from N or CR A ; B1 - B4, each occurrence of which is the same as or different from the others, is selected from N or CR B ; D1 - D2, each time it appears, is the same as or different from, and is selected from N or CR D ; U1 - U4 are the same as or different from each other each time they appear and are each selected from N or CR U ; W1 - W4, each occurrence of which is the same as or different from one another, is independently selected from N or CR W ; R A 、R B 、R D 、R U and R W each time it appears is the same as or different from and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and R W at least one of which is selected from F; Adjacent substituents R A 、R B 、R D may optionally be linked to form a ring; Adjacent substituents R U and R W can optionally be linked to form a ring; Preferably, each occurrence of R is the same or different and is selected from the group consisting of deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms; At least one of A1 - A3 is selected from CR A , and / or at least one of B1 - B4 is selected from CR B , and said R A , R B is the same or different each time it appears and is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, cyano, hydroxy, mercapto, and combinations thereof; More preferably, A2 is selected from CR A , and / or one of B2 and B3 is selected from CR B ; Most preferably, each occurrence of said R is the same or different and is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclopentyl; The R A , R B is the same or different each time it appears and is selected from the group consisting of: deuterium, fluorine, cyano, hydroxy, mercapto, amino, methoxy, phenoxy, methylthio, phenylthio, dimethylamino, diphenylamino, phenylmethylamino, vinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, piperidinyl, morpholinyl, benzyl, methyl, ethyl, isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, phenyldimethylsilyl, trimethylgermyl, triethylgermyl, phenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, pyridyl, pyrimidyl, triazinyl, and combinations thereof.
16. The metal complex according to claim 13, wherein, The metal complex has a structure of Ir(L a )(L b )2 or Ir(L a )2(L b ) or Ir(L a )(L b )(L c ); Wherein, when the metal complex has the structure of Ir(L a )(L b )2, the L a is selected from any one of the group consisting of L a1 to L a632 , and each occurrence of the L b is the same as or different from each other and is selected from any one or two of the group consisting of L b1 to L b433 ; when the metal complex has the structure of Ir(L a )2(L b ), each occurrence of the L a is the same as or different from each other and is selected from any one or any two of the group consisting of L a1 to L a632 , and the L b is selected from any one of the group consisting of L b1 to L b433 ; when the metal complex has the structure of Ir(L a )(L b )(L c ), the L a is selected from any one of the group consisting of L a1 to L a632 , the L b is selected from any one of the group consisting of L b1 to L b433 , and the L c is selected from any one of the group consisting of L c1 to L c329 ; optionally, the hydrogen atoms in the structure of the metal complex can be partially or completely replaced by deuterium; Preferably, the metal complex is selected from the group consisting of Compound 1 to Compound 1204; Among them, the compounds 1 to 1044 have the structure of Ir(L a )(L b )2, wherein the two L b are the same, and L a and L b are respectively selected from the structures listed in the following table: Compounds 1045 to 1144 have the structure of Ir(L a )2(L b ), where two L a are the same, and L a and L b are respectively selected from the structures listed in the following table: Compounds 1145 to 1204 have the structure of Ir(L a )(L b )(L c ), where L a , L b and L c are respectively selected from the structures listed in the following table:
17. An electroluminescent device, comprising: Anode, Cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer contains the metal complex according to any one of claims 1-16.
18. The electroluminescent device according to claim 17, wherein, The organic layer is a light-emitting layer, and the metal complex is a light-emitting material.
19. The electroluminescent device according to claim 18, wherein, The electroluminescent device emits orange-red light or white light.
20. The electroluminescent device according to claim 18, wherein, The light-emitting layer further includes at least one host material; Preferably, the at least one host material contains at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silifluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
21. A compound composition comprising the metal complex according to any one of claims 1-16.
Citation Information
Patent Citations
Isaac t
US1320161A
Very low voltage, high efficiency phosphorescent OLED in a p-i-n structure
US20030230980A1
Transparent electrodes
US20040174116A1
Organic electroluminescent materials and devices
US20150349273A1
Organic electroluminescent materials and devices
US20160359122A1