Organic electroluminescent material and device thereof
By using metal complexes with a specific Formula 1 structure in blue phosphor devices, the limitations of existing blue phosphor devices in terms of half-maximum width, efficiency and lifetime are solved, and high-efficiency and long-life luminescent performance are achieved.
Patent Information
- Application Number
- CN202311822524.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-12-27
- Publication Date
- 2025-06-27
AI Technical Summary
Existing blue phosphorescent devices have limitations in half-maximum width, efficiency and life, making it difficult to achieve efficient and long-life luminous performance.
The luminescent performance of the device is optimized by introducing a fused (hetero)alkane ring on the benzimidazole carbene ring using a metal complex with a specific structure of Formula 1 as the luminescent material.
It achieves narrow half-maximum width, very high current efficiency and external quantum efficiency, improving the comprehensive performance of blue phosphorescent devices.
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Figure CN120209040A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to metal complexes for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a metal complex having a specific Formula 1 structure and an organic electroluminescent device and a 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 state-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between 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 in the fabrication of 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 singlets and triplets, 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 an exact structure, small molecules can have a large molecular weight. 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 in 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] US20230065887A1 discloses a metal complex comprising the structure of general formula I below and its application in an organic electroluminescent device: Each of ring B, ring C and ring D is independently a 5- or 6-membered carbocyclic or heterocyclic ring; R A and R D are independently substituents such as hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, etc.; at least one of R1, R2, R A , R B , R C , R D , R E contains the structure represented by formula II---Q(R 3 )(R 4 ) a (R 5 ) b , formula The application discloses some platinum metal compounds in specific structures such as However, it does not disclose or teach metal complexes with a fused (hetero)alkane ring introduced on the benzimidazole carbene ring, let alone disclose or teach the excellent effects brought by such metal complexes with a fused (hetero)alkane ring introduced on the benzimidazole carbene ring when used in devices.
[0009] Currently, in the research of blue phosphorescent devices, there are still certain limitations in their full width at half maximum, device efficiency, etc. Therefore, blue phosphorescent materials are worthy of further in-depth research and development. SUMMARY OF THE INVENTION
[0010] The present invention aims to provide a series of metal complexes having the structure of formula 1 to solve at least part of the above problems. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can provide excellent device performance, such as having a narrow full width at half maximum, very high current efficiency and external quantum efficiency. These advantages are of great help for improving the level of blue phosphorescent devices.
[0011] According to an embodiment of the present invention, a metal complex having the structure of formula 1 is disclosed:
[0012]
[0013] In formula 1,
[0014] Metal M is selected from metals with a relative atomic mass greater than 40;
[0015] Ring A, ring B, and ring D are each independently selected from unsaturated carbocyclic rings having 5-30 carbon atoms, unsaturated heterocyclic rings having 3-30 carbon atoms, or a combination thereof;
[0016] L1 and L2 are each independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’)y , an arylene group having 6 to 30 carbon atoms, substituted or unsubstituted, a heteroarylene group having 3 to 30 carbon atoms, substituted or unsubstituted, or a combination thereof; each occurrence of y is the same or different and is selected from 1, 2, 3, 4 or 5;
[0017] K1 - K4 are each independently selected from a single bond, O or S;
[0018] Z1 - Z3 are each independently selected from C or N;
[0019] R a , R b and R d each occurrence is the same or different and is represented as mono - substituted, multi - substituted or unsubstituted;
[0020] R a1 each occurrence is the same or different and is represented as mono - substituted or multi - substituted;
[0021] Said R a1 is selected from an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted, a cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted, or a combination thereof, and the number of carbon atoms in said R a1 is at least 5;
[0022] X1 - X4 each occurrence is the same or different and is selected from C, CR x or N, and any two directly - bonded ones of X1 - X4 are C and are respectively connected to the two “*” in Formula 2;
[0023]
[0024] In Formula 2,
[0025] “*” represents the connection position of said Formula 2;
[0026] T, T1 and T2 each occurrence is the same or different and is selected from C(R t )2, Si(R t )2, NR t , O, S or Se;
[0027] n is 0, 1, 2, 3, 4 or 5;
[0028] R, R’, R a , R b , R d , R x , R tEach 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] Adjacent substituents R, R’, R a , R b , R d , R x , R t can optionally be linked to form a ring.
[0030] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the metal complex having the structure of Formula 1.
[0031] According to one embodiment of the present invention, a composition is disclosed, which contains the metal complex having the structure of Formula 1.
[0032] The present invention discloses a series of metal complexes having the structure of Formula 1. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can provide excellent device performance, such as having a narrow full width at half maximum, very high current efficiency, and external quantum efficiency. These advantages are extremely helpful for improving the level of blue phosphorescent devices. BRIEF DESCRIPTION OF THE DRAWINGS
[0033] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the metal complexes and compositions disclosed herein.
[0034] Figure 2Another schematic diagram of an organic light-emitting device that may contain the metal complexes and compositions disclosed herein. Detailed Description
[0035] OLEDs can be fabricated on various substrates such as glass, plastic, and metal. Figure 1 An 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 may also be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of which is incorporated herein by reference.
[0036] 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, which include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer, are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. The principles and use 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 a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.
[0037] 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 completely omitted. 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.
[0038] 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.
[0039] 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.
[0040] 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) with 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.
[0041] The materials and structures described herein can also be used in other organic electronic devices listed above.
[0042] 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, other layers can exist 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.
[0043] 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.
[0044] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.
[0045] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical limit by delayed fluorescence. 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).
[0046] 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 a very small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also referred to 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 of the triplet state, then the fraction of singlet excited state backfilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.
[0047] The characteristics of E-type delayed fluorescence can be seen 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 usually 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).
[0048] Definition of substituent terms
[0049] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.
[0050] 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.
[0051] 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.
[0052] 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.
[0053] Alkenyl - As used herein, it encompasses straight-chain, branched-chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl 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.
[0054] Alkynyl - As used herein, it encompasses straight-chain alkynyl groups. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl 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, phenylpropargyl, 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.
[0055] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl 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.
[0056] Heterocyclic group - 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 nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and 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.
[0057] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and 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.
[0058] Alkoxy - As used herein, it is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl 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.
[0059] 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.
[0060] 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] In terms of azadibenzofuran, azadibenzothiophene, etc., 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-mentioned aza derivatives, and all such analogs are determined to be included in the terms described herein.
[0066] In the present disclosure, unless otherwise defined, when any one of the terms consisting of 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 of 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 can 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0067] 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.
[0068] 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 compounds may be preferred.
[0069] 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.
[0070] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring, adjacent substituents in the compounds cannot be linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, which includes both the case where adjacent substituents can be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be linked to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro rings, bridged rings, fused rings, 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.
[0071] The expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0072]
[0073] The expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0074]
[0075] In addition, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be considered as referring to the case where, when one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0076]
[0077] According to an embodiment of the present invention, a metal complex having the structure of Formula 1 is disclosed:
[0078]
[0079] In Formula 1,
[0080] metal M is selected from metals having a relative atomic mass greater than 40;
[0081] Ring A, Ring B, and Ring D are each independently selected from unsaturated carbocycles having 5 - 30 carbon atoms, unsaturated heterocycles having 3 - 30 carbon atoms, or a combination thereof;
[0082] L1 and L2 are each independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , substituted or unsubstituted arylene having 6 - 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof; y is the same or different each time it appears and is selected from 1, 2, 3, 4, or 5;
[0083] K1 - K4 are each independently selected from a single bond, O, or S;
[0084] Z1 - Z3 are each independently selected from C or N;
[0085] R a , R b and R d are the same or different each time they appear and are represented as mono - substituted, multi - substituted, or unsubstituted;
[0086] R a1 is the same or different each time it appears and is represented as mono - substituted or multi - substituted;
[0087] Said R a1 is selected from substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or a combination thereof, and the number of carbon atoms in said R a1 is at least 5;
[0088] X1 - X4 are the same or different each time they appear and are selected from C, CR x or N, and any two directly - bonded ones among X1 - X4 are C and are respectively connected to the two “*” in Formula 2;
[0089]
[0090] In Formula 2,
[0091] "*" represents the linking position of said formula 2;
[0092] T, T1 and T2 are each independently selected from C(R t )2, Si(R t )2, NR t , O, S or Se;
[0093] n is 0, 1, 2, 3, 4 or 5;
[0094] R, R’, R a , R b , R d , R x , R t are each 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;
[0095] Adjacent substituents R, R’, R a , R b , R d , R x , R t can optionally be linked to form a ring.
[0096] As used herein, "unsaturated carbocyclic ring" includes aromatic unsaturated carbocyclic rings (aryl rings) and non - aromatic unsaturated carbocyclic rings; "unsaturated heterocyclic ring" includes aromatic unsaturated heterocyclic rings (heteroaryl rings) and non - aromatic unsaturated heterocyclic rings.
[0097] As used herein, "adjacent substituents R, R’, R a , R b , Rd , R x , R t "can optionally be linked to form a ring", which is intended to indicate adjacent substituent groups. For example, between two substituents R', between two substituents R a , between two substituents R b , between two substituents R d , between two substituents R x , between two substituents R t , between substituents R a and R', between substituents R b and R', between substituents R d and R', between substituents R t and R x , between substituents R and R x , and between substituents R d and R x , between these substituents, any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituents can also not be linked to form a ring. For example, adjacent substituents R and R a are not linked to form a ring.
[0098] In this article, n is 0, 1, 2, 3, 4 or 5; when n is 0, T1 and T2 in Formula 2 are directly linked, and at this time the structure of Formula 2 is When n is 2, the structure of Formula 2 at this time is
[0099] In this article, any two directly bonded ones among X1 - X4 are C and are respectively connected to the two "*" in Formula 2, and there are the following three cases: one is that X1 and X2 are C and are respectively connected to the two "*" in Formula 2; the second is that X2 and X3 are C and are respectively connected to the two "*" in Formula 2; the third is that X3 and X4 are C and are respectively connected to the two "*" in Formula 2.
[0100] According to an embodiment of the present invention, wherein the compound has a structure represented by the general formula M(L a )(L b ), wherein L a and L b are respectively the first ligand and the second ligand coordinated with the metal M, and the L a has a structure represented by Formula A: wherein "#" in Formula A represents the position connected to L b ; the L b has a structure represented by Formula B: wherein in Formula B represents the position connected to L a .
[0101] According to one embodiment of the present invention, M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt.
[0102] According to one embodiment of the present invention, M is selected from Pt or Pd.
[0103] According to one embodiment of the present invention, M is selected from Pt.
[0104] According to one embodiment of the present invention, L1 is selected from a single bond, O, S, (CR’R’) y , (SiR’R’) y , NR’, or a combination thereof; y is 1 or 2.
[0105] According to one embodiment of the present invention, L1 is selected from a single bond, O or S.
[0106] According to one embodiment of the present invention, L1 is selected from a single bond.
[0107] According to one embodiment of the present invention, K1-K4 are selected from a single bond.
[0108] According to one embodiment of the present invention, Z1 is selected from N, and Z2 and Z3 are selected from C.
[0109] According to one embodiment of the present invention, ring A, ring B, and ring D are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6-30 carbon atoms, a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof.
[0110] According to one embodiment of the present invention, ring A, ring B, and ring D are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6-18 carbon atoms, a heteroaromatic ring having 3-18 carbon atoms, or a combination thereof.
[0111] According to one embodiment of the present invention, ring A, ring B, and ring D are each independently selected from a cyclopentadiene ring, a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolocarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.
[0112] According to one embodiment of the present invention, the metal complex has a structure represented by one of Formulas 1-1 to 1-6:
[0113]
[0114]
[0115] In Formulas 1-1 to 1-6,
[0116] L2 is selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , 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; y is the same or different each time it appears and is selected from 1, 2, 3, 4 or 5;
[0117] T, T1 and T2 are the same or different each time they appear and are selected from C(R t )2, Si(R t )2, NR t , O, S or Se;
[0118] n is 0, 1, 2, 3, 4 or 5;
[0119] X1 - X4 are each independently selected from C, CR x or N, and any two directly bonded to each other among X1 - X4 are C and are respectively connected to two “*”;
[0120] Y1 - Y4 are the same or different each time they appear and are selected from CR a , CR a1 or N, and at least one of Y1 - Y4 is selected from CR a1 , where the R a1 is selected from a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, or a combination thereof, and the number of carbon atoms of the R a1 is at least 5;
[0121] Y5 - Y 16 are the same or different each time they appear and are selected from CR y or N;
[0122] The R, R’, R x , R y , R a , R tEach 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;
[0123] Adjacent substituents R, R', R x , R y , R a , R t can optionally be linked to form a ring.
[0124] In this embodiment, "adjacent substituents R, R', R x , R y , R a , R t can optionally be linked to form a ring" is intended to mean that among the adjacent substituent groups, for example, between two substituents R', between two substituents R x , between two substituents R y , between two substituents R a , between two substituents R t , between two substituents R t and R x , between two substituents R y and R', between two substituents R x and R N , between two substituents R and R x , and between two substituents R y and R x , any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituents can also not be linked to form a ring, for example, adjacent substituents R and R a are not linked to form a ring.
[0125] According to an embodiment of the present invention, the metal complex has a structure represented by Formula 1-1.
[0126] According to an embodiment of the present invention, X2 and X3 are C and are respectively connected to two “*”, and X1 and X4 are each independently selected from CR x .
[0127] According to an embodiment of the present invention, the R x is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
[0128] According to an embodiment of the present invention, n is selected from 1 or 2.
[0129] According to an embodiment of the present invention, T, T1 and T2 are the same or different each time they appear and are selected from C(R t )2.
[0130] According to an embodiment of the present invention, the R t is the same or different each time it appears 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, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.
[0131] According to an embodiment of the present invention, the R t is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
[0132] According to an embodiment of the present invention, T1 is selected from C(R t )2, and the R tEach 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 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, and combinations thereof.
[0133] According to one embodiment of the present invention, T1 is selected from C(R t )2, where each R t 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.
[0134] According to one embodiment of the present invention, T1 is selected from C(R t )2, where each R t Each occurrence is the same as or different from and is selected from the group consisting of: deuterium, a halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
[0135] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R t 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 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, and combinations thereof.
[0136] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R t 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.
[0137] According to one embodiment of the present invention, T2 is selected from C(R t )2, where each R t Each occurrence is the same as or different from and is selected from the group consisting of: deuterium, a halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
[0138] According to one embodiment of the present invention, T1 and T2 are selected from C(Me)2.
[0139] According to one embodiment of the present invention, wherein each occurrence of Y1 - Y4 is the same or different and is independently selected from CR a or CR a1 , and at least one of Y1 - Y4 is selected from CR a1 .
[0140] According to one embodiment of the present invention, wherein Y2 is selected from CR a1 , the R a1 is independently selected from a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, or a combination thereof, and the number of carbon atoms of the R a1 is at least 5.
[0141] According to one embodiment of the present invention, wherein Y3 is selected from CR a1 , the R a1 is independently selected from a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, or a combination thereof, and the number of carbon atoms of the R a1 is at least 5.
[0142] According to one embodiment of the present invention, wherein the R a1 is selected from the group consisting of Ry - 1 to Ry - 53, and the specific structures of Ry - 1 to Ry - 53 are shown in claim 10.
[0143] According to one embodiment of the present invention, wherein the R has a structure represented by formula 3:
[0144]
[0145] In formula 3,
[0146] "**" represents the connecting position of formula 3;
[0147] Ring F, ring G and ring N are each independently selected from an unsaturated carbocyclic ring having 5 - 30 carbon atoms, an unsaturated heterocyclic ring having 3 - 30 carbon atoms, or a combination thereof each time they appear;
[0148] Z4 - Z7 are each independently selected from C or N each time they appear;
[0149] R f , R g , R n are each independently represented as mono - substituted, multi - substituted or unsubstituted each time they appear;
[0150] R f , R g , R nEach 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 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;
[0151] Adjacent substituents R f , R g , R n can optionally be linked to form a ring.
[0152] As used herein, "adjacent substituents R f , R g , R n can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between two substituents R f , between two substituents R g , and between two substituents R n , any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituents can also not be linked to form a ring.
[0153] According to one embodiment of the present invention, wherein said R has the structure shown in Formula 3-1:
[0154]
[0155] In Formula 3-1,
[0156] F1 to F5 are each independently selected from CR f or N; G1 to G5 are each independently selected from CR g or N; N1 to N3 are each independently selected from CR n or N;
[0157] Said R f ,R g ,R n is the same or different each time it appears 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;
[0158] Adjacent substituents R f ,R g ,R n can optionally be joined to form a ring.
[0159] According to one embodiment of the present invention, wherein each of said F1 to F5 is independently selected from CR f .
[0160] According to one embodiment of the present invention, wherein each of said G1 to G5 is independently selected from CR g .
[0161] According to one embodiment of the present invention, wherein each of said N1 to N3 is independently selected from CR n .
[0162] According to one embodiment of the present invention, wherein said R f 、R g and R nEach occurrence is the same as or different from each other 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, and combinations thereof.
[0163] According to one embodiment of the present invention, wherein said R f 、R g and R n Each occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, deuterated methyl, ethyl, n - propyl, isopropyl, cyclopropyl, n - butyl, isobutyl, tert - butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, triphenylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0164] According to one embodiment of the present invention, wherein said F1 to F5 are selected from CH or CD.
[0165] According to one embodiment of the present invention, wherein said G1 to G5 are selected from CH or CD.
[0166] According to one embodiment of the present invention, wherein said R is selected from the group consisting of An - 1 to An - 55:
[0167]
[0168]
[0169]
[0170] According to one embodiment of the present invention, wherein the hydrogen in the structures of An - 1 to An - 55 can be partially or completely replaced by deuterium.
[0171] According to one embodiment of the present invention, wherein said L2 is selected from a single bond, O, S, (SiR’R’) y , NR’, (CR’R’) y, or a combination thereof; y is 1 or 2; each occurrence of R' is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
[0172] According to one embodiment of the present invention, wherein L2 is selected from a single bond, O or S.
[0173] According to one embodiment of the present invention, wherein L2 is selected from O.
[0174] According to one embodiment of the present invention, wherein Y5-Y 16 each occurrence is the same or different and is selected from CR y .
[0175] According to one embodiment of the present invention, wherein R y each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
[0176] According to one embodiment of the present invention, wherein R y each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0177] According to one embodiment of the present invention, wherein the metal complex has the structure of Pt(L a )(L b ), wherein L a and L b are the first ligand and the second ligand coordinated to the metal Pt respectively, and L a is selected from L a 1-1 to L a 1-63, La 2-1 to L a 2-34, and L a 3-1 to L a a group consisting of 3-44, wherein the L b is selected from the group consisting of L b 1-1 to L b 1-33, L b 2-1 to L b 2-41, and L b 3-1 to L b a group consisting of 3-43, wherein the L a 1-1 to L a 1-63, L a 2-1 to L a 2-34, L a 3-1 to L a 3-44, L b 1-1 to L b 1-33, L b 2-1 to L b 2-41, and L b 3-1 to L b The specific structure of 3-43 is shown in claim 14.
[0178] According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complexes Pt1 to Pt597, and the specific structures of the metal complexes Pt1 to Pt597 are shown in claim 14.
[0179] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which comprises:
[0180] an anode,
[0181] a cathode,
[0182] and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a metal complex having the structure of Formula 1, and the metal complex having the structure of Formula 1 is as shown in any of the above embodiments.
[0183] According to an embodiment of the present invention, wherein the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.
[0184] According to an embodiment of the present invention, wherein the device emits blue light.
[0185] According to an embodiment of the present invention, wherein the device emits white light.
[0186] According to an embodiment of the present invention, wherein the light-emitting layer contains at least one host material.
[0187] According to one embodiment of the present invention, the light-emitting layer comprises at least two host materials.
[0188] According to one embodiment of the present invention, the host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicofluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0189] According to one embodiment of the present invention, the light-emitting layer comprises a first host material and a second host material.
[0190] According to one embodiment of the present invention, the first host material has a structure represented by Formula 4:
[0191]
[0192] In Formula 4,
[0193] L 11 is selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;
[0194] Ar 11 is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted amino group having 0 - 30 carbon atoms, or a combination thereof;
[0195] R 11 each occurrence is the same or different and represents mono-substitution, multi-substitution, or no substitution;
[0196] R 11Each 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;
[0197] Adjacent substituents R 11 can optionally be linked to form a ring.
[0198] As used herein, adjacent substituents R 11 can optionally be linked to form a ring, which is intended to mean that two substituents R 11 can be linked to form a ring. Obviously, two substituents R 11 may also not be linked to form a ring.
[0199] According to one embodiment of the present invention, wherein the first host material has a structure represented by Formula 4-1 or Formula 4-2:
[0200]
[0201] L 11 L 12 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0202] Ar 11 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a combination thereof;
[0203] R 11 Each occurrence is the same as or different from and represents mono-substitution, multi-substitution or no substitution;
[0204] R 11 Each 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;
[0205] Adjacent substituents R 11 Can optionally be joined to form a ring.
[0206] According to one embodiment of the present invention, wherein the first host material has a structure represented by Formula 4 - 3 or Formula 4 - 4:
[0207]
[0208] Ar 11 Selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted amino having 0 - 30 carbon atoms, or combinations thereof;
[0209] L 11 Selected from a single bond, substituted or unsubstituted arylene having 6 - 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or combinations thereof;
[0210] R 11 Each occurrence represents single - substitution, multi - substitution or no substitution, the same or different;
[0211] R 11Each 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;
[0212] Adjacent substituents R 11 Can optionally be linked to form a ring.
[0213] According to one embodiment of the present invention, wherein R 11 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
[0214] According to one embodiment of the present invention, wherein said R 11 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6-18 carbon atoms, substituted or unsubstituted heteroaryl having 3-18 carbon atoms, and combinations thereof.
[0215] According to one embodiment of the present invention, wherein said R 11 Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzosilole, dibenzosilole, benzothiophene, dibenzothiophene, dibenzoselenophene, and combinations thereof.
[0216] According to one embodiment of the present invention, in Formulas 4-1 to 4-4, there are a plurality of R 11 substituents, and at least one of the plurality of R 11 substituents is a carbazolyl group, for example, one or two of them are carbazolyl groups.
[0217] According to one embodiment of the present invention, in Formulas 4-1 to 4-4, there are a plurality of R 11 substituents, and at least one of the plurality of R 11 substituents and Ar 11 is a carbazolyl group, for example, one or two of them are carbazolyl groups.
[0218] According to one embodiment of the present invention, the first host material is selected from the group consisting of Compound P-1 to Compound P-31:
[0219]
[0220]
[0221]
[0222] According to one embodiment of the present invention, the second host material has a structure represented by Formula 5:
[0223]
[0224] In Formula 5,
[0225] Q1 to Q3 are the same or different each time they appear and are selected from CR4 or N, and at least one of Q1 to Q3 is N;
[0226] L is the same or different each time it appears and is selected from the group consisting of: a single bond, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, and combinations thereof;
[0227] Each occurrence of R1-R4 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;
[0228] Adjacent substituents R4 can optionally be joined to form a ring.
[0229] According to one embodiment of the present invention, in Formula 5, Q1 to Q3 are N.
[0230] According to one embodiment of the present invention, each occurrence of said R1 to R4 is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
[0231] According to one embodiment of the present invention, the second host material has a structure represented by Formula 5-1:
[0232]
[0233] In Formula 5-1,
[0234] R1 and R2 are each independently selected from substituted or unsubstituted heteroaryl having 3-30 carbon atoms;
[0235] L 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;
[0236] R L Each occurrence is the same or different 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, and combinations thereof.
[0237] According to one embodiment of the present invention, wherein each of said R1 and R2 is independently selected from the group consisting of carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, and combinations thereof.
[0238] According to one embodiment of the present invention, wherein said L is selected from a single bond, phenylene, biphenylene, terphenylenylene, or pyridinylene.
[0239] According to one embodiment of the present invention, wherein said R L Each occurrence is the same or different and is selected from the group consisting of 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.
[0240] According to one embodiment of the present invention, wherein said R L Each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms.
[0241] According to one embodiment of the present invention, wherein said R LEach occurrence is the same as or different from and is selected from the group consisting of: phenyl, biphenyl, triphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzosilolyl, dibenzosilolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0242] According to one embodiment of the present invention, wherein the second host material is selected from the group consisting of compounds N-2-1 to compound N-2-45:
[0243]
[0244]
[0245]
[0246]
[0247]
[0248] According to another embodiment of the present invention, a composition is disclosed, which comprises a metal complex having a structure of Formula 1, and the metal complex having the structure of Formula 1 is as shown in any of the above embodiments.
[0249] In combination with other materials
[0250] 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.
[0251] 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 used in combination with a variety of luminescent 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.
[0252] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. All reagents without further specification were used as received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art (including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beiyike, 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 test methods and can obtain the inherent data of the samples determinately and without influence, the above relevant content will not be elaborated further in this patent.
[0253] Examples of material synthesis:
[0254] The preparation method of the metal complexes of the present invention is not limited. Typically but not restrictively, the following metal complexes are taken as examples, and their synthetic routes and preparation methods are as follows:
[0255] Synthesis Example 1: Synthesis of metal complex Pt33
[0256] Step 1: Synthesis of intermediate 3
[0257]
[0258] Under nitrogen conditions, intermediate 1 (3.4 g, 13.3 mmol), intermediate 2 (4.0 g, 13.3 mmol), palladium acetate (149 mg, 0.67 mmol), BINAP (0.828 g, 1.33 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol) and toluene (133 mL) were added to a flask. After the reaction temperature was raised to 110 °C, the mixture was stirred overnight. After detecting the end of the reaction by TLC, it was cooled to room temperature. After concentrating and removing the solvent, intermediate 3 (4.6 g, 9.7 mmol) was obtained by column chromatography.
[0259] Step 2: Synthesis of intermediate 5
[0260]
[0261] Under nitrogen atmosphere, 3-bromo-N-acetylaniline (2.25 g, 10.5 mmol), Intermediate 4 (3.5 g, 10.5 mmol), copper(I) iodide (199.5 mg, 1.05 mmol), 2-pyridinecarboxylic acid (258.3 mg, 2.1 mmol), and potassium phosphate (4.45 g, 21.0 mmol) were added into a 100 mL flask, and then dimethyl sulfoxide (DMSO, 35 mL) was added thereto. The reaction was heated to 150 °C and stirred overnight. After the reaction was completed, it was cooled to room temperature, and the reaction was quenched by adding water. The reaction mixture was separated by liquid-liquid extraction, and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed three times with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated to remove the solvent, and then purified by column chromatography to obtain Intermediate 5 (4.9 g, 10.5 mmol).
[0262] Step 3: Synthesis of Intermediate 6
[0263]
[0264] Intermediate 5 (4.9 g, 10.5 mmol) and sodium hydroxide (2.9 g, 72.5 mmol) were added into a flask, and 44 mL of ethanol / water (4:1) mixed solvent was added. The reaction was heated to 90 °C and stirred overnight. After the reaction was completed, it was cooled to room temperature. The reaction mixture was separated by liquid-liquid extraction, and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed three times with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated to remove the solvent, and then purified by column chromatography to obtain Intermediate 6 (4.4 g, 10.4 mmol).
[0265] Step 4: Synthesis of Intermediate 7
[0266]
[0267] Under nitrogen atmosphere, Intermediate 3 (4.6 g, 9.7 mmol), Intermediate 6 (4.1 g, 9.7 mmol), palladium(II) acetate (86.9 mg, 0.388 mmol), S-Phos (318.2 mg, 0.776 mmol), sodium tert-butoxide (1.86 g, 19.4 mmol), and xylene (100 mL) were added into a flask. The reaction temperature was raised to 140 °C and stirred overnight. After the reaction was completed as detected by TLC, it was cooled to room temperature, concentrated to remove the solvent, and then Intermediate 7 (5.8 g, 6.7 mmol) was obtained by column chromatography.
[0268] Step 5: Synthesis of Intermediate 8
[0269]
[0270] Under nitrogen atmosphere, intermediate 7 (2.93 g, 3.4 mmol), triethyl orthoformate (22.3 g, 150.3 mmol) and concentrated hydrochloric acid (0.8 mL) were added to a flask. The reaction temperature was raised to 100 °C and stirred overnight. After the reaction was completed as detected by TLC, it was cooled to room temperature. The solvent was removed by concentration and intermediate 8 (1.8 g, 2.0 mmol) was obtained by column chromatography.
[0271] Step 6: Synthesis of metal complex Pt33
[0272]
[0273] Under nitrogen atmosphere, intermediate 8 (1.8 g, 2.0 mmol), Ag2O (231.7 mg, 1.0 mmol) and DCE (50 mL) were added to a flask. The reaction was carried out at room temperature for 24 h. After the reaction was complete, the solvent was removed under reduced pressure. Then, (1,5-cyclooctadiene) platinum dichloride (748 mg, 2.0 mmol) and dichlorobenzene (80 mL) were added to the flask. The reaction temperature was raised to 185 °C and stirred for 24 h. After cooling to room temperature, metal complex Pt33 (1.07 g, 1.0 mmol) was obtained by column chromatography. The product was identified as the target product with a molecular weight of 1065.48.
[0274] 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 metal complex structures of the present invention by improving it.
[0275] The preparation method of the electroluminescent device is not limited. The preparation method in the following examples is only an example and should not be construed as a limitation. Those skilled in the art can reasonably improve the preparation method in the following examples according to the prior art. Exemplarily, the ratio of various materials in the light-emitting layer is 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 85% - 99%, and the light-emitting material can account for 1% - 15%. 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.
[0276] Device Examples
[0277] Device Example 1
[0278] First, clean the glass substrate, which has an indium tin oxide (ITO) anode with a thickness of 80 nm, and then treat it with oxygen plasma and UV ozone. After the treatment, dry the substrate in a glove box to remove moisture. Then mount the substrate on a substrate holder and load it into a vacuum chamber. The following specified organic layers are deposited sequentially on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / sec under a vacuum of about 10 -7 Torr. Compounds HI and HT are co-evaporated and used as the hole injection layer (HIL) with a thickness of Compound HT is used as the hole transport layer (HTL) with a thickness of Compound P-21 is used as the electron blocking layer (EBL) with a thickness of Then, compound P-22 as the first host material, compound N-2-39 as the second host material, and the metal complex Pt33 of the present invention as the dopant are co-evaporated and used as the emitting layer (EML) with a thickness of Compound N-2-39 is used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compounds ET and lithium 8-hydroxyquinolate (Liq) are co-evaporated as the electron transport layer (ETL) with a thickness of Finally, deposit a thickness of LiF as the electron injection layer, and deposit aluminum of thickness as the cathode. Then transfer the device back to the glove box and encapsulate it with a glass cover and a moisture absorbent to complete the device.
[0279] Device Comparative Example 1
[0280] The preparation method of Device Comparative Example 1 is the same as that of Device Example 1, except that metal complex Pt-A is used instead of the metal complex Pt33 of the present invention in the emitting layer (EML).
[0281] Device Comparative Example 2
[0282] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that metal complex Pt-B is used instead of the metal complex Pt33 of the present invention in the emitting layer (EML).
[0283] Table 1 Partial device structures of device examples and comparative examples
[0284]
[0285] The material structures used in the device are as follows:
[0286]
[0287] At 10 mA / cm2 The CIE values, maximum emission wavelength (λ max ), full width at half maximum (FWHM), current efficiency (CE), and external quantum efficiency (EQE) of Example 1 and Comparative Examples 1-2 were measured. The relevant data are shown in Table 2.
[0288] Table 2 Device Data
[0289]
[0290] In the blue phosphorescent device, the FWHM, CE, and EQE of Comparative Example 1 and Comparative Example 2 were all at relatively high levels. Compared with Comparative Example 1, Example 1 had the same maximum emission wavelength, the FWHM was further narrowed by 0.9 nm, the CE was further increased by 9.5%, and the EQE was further increased by 7.6%. This indicates that due to the fused (hetero)alkane ring represented by Specific Formula 2 in the metal complex of Formula 1 of the present invention, the device performance has been further improved. Compared with Comparative Example 2, Example 1 had the same maximum emission wavelength, the FWHM was basically the same, the CE was further increased by 7.8%, and the EQE was further increased by 4.2%. This indicates that due to the specific R a1 substituent in the metal complex of Formula 1 of the present invention, the device performance has been further improved. The above data prove the advantages of the metal complex of Formula 1 of the present invention in the device. It is unexpected that the metal complex of Formula 1 of the present invention can further significantly improve the CE and EQE of the device while maintaining a narrow FWHM. Moreover, the CE of Example 1 was as high as 27.13 cd / A and the EQE was as high as 20.72%, which achieved very excellent device performance in blue phosphorescent devices and had great application potential.
[0291] The above results show that the metal complex of Formula 1 of the present invention can achieve a narrow FWHM, very high current efficiency, and external quantum efficiency when applied to blue phosphorescent devices, thereby improving the comprehensive performance of the devices. These advantages are extremely helpful for improving the level of blue phosphorescent devices.
[0292] 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 obvious to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein 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 regarding why the present invention works are not intended to be limiting.
Claims
1. A metal complex having the structure of Formula 1: In Formula 1, the metal M is selected from metals with a relative atomic mass greater than 40; Ring A, Ring B, and Ring D are each independently selected from unsaturated carbocycles having 5 - 30 carbon atoms, unsaturated heterocycles having 3 - 30 carbon atoms, or a combination thereof; L1 and L2 are each independently selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof; y is the same or different each time it appears and is selected from 1, 2, 3, 4 or 5; K1 - K4 are each independently selected from a single bond, O, or S; Z1 - Z3 are each independently selected from C or N; R a , R b and R d each occurrence is the same as or different from the others and represents mono-substitution, multi-substitution or no substitution; R a1 which is the same or different each time it appears and represents a mono-substitution or a multi-substitution; The R a1 is selected from 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, or a combination thereof, and the number of carbon atoms in the R a1 is at least 5; X1 - X4 are each independently selected from C, CR, x or N, and any two directly - bonded ones of X1 - X4 are C and are respectively connected to the two "*" in Formula 2; In Formula 2, "*” represents the connection position of Formula 2; T, T1, and T2 are each independently selected, each time they appear, from C(R t )2, Si(R t )2, NR t , O, S, or Se; n is 0, 1, 2, 3, 4, or 5; R, R’, R a , R b , R d , R x , R t each occurrence 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; Adjacent substituents R, R’, R a , R b , R d , R x , R t can optionally be linked to form a ring.
2. The metal complex according to claim 1, wherein the M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, or Pt; preferably, the M is selected from Pt or Pd; more preferably, the M is selected from Pt.
3. The metal complex according to claim 1 or 2, wherein the K1 - K4 are selected from a single bond.
4. The metal complex according to claim 1 or 2, wherein the Z1 is selected from N, and Z2 and Z3 are selected from C.
5. The metal complex according to claim 1 or 2, wherein Ring A, Ring B, and Ring D are each independently selected from five - membered unsaturated carbocycles, aromatic rings having 6 - 30 carbon atoms, heteroaromatic rings having 3 - 30 carbon atoms, or a combination thereof; preferably, Ring A, Ring B, and Ring D are each independently selected from five - membered unsaturated carbocycles, aromatic rings having 6 - 18 carbon atoms, heteroaromatic rings having 3 - 18 carbon atoms, or a combination thereof; more preferably, Ring A, Ring B, and Ring D are each independently selected from a cyclopentadiene ring, a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolocarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.
6. The metal complex according to claim 1, wherein the metal complex has a structure represented by one of Formula 1 - 1 to Formula 1 - 6: In Formula 1 - 1 to Formula 1 - 6, L2 is selected from a single bond, O, S, Se, (SiR’R’) y , PR’, NR’, (CR’R’) y , a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof; y is the same as or different from each occurrence and is selected from 1, 2, 3, 4, or 5; T, T1, and T2 are each independently selected, each time they appear, from C(R t )2, Si(R t )2, NR t , O, S, or Se; n is 0, 1, 2, 3, 4, or 5; X1-X4 are each independently selected from C, CR x or N, and any two directly linked among X1-X4 are C and are respectively connected to two "*"; Y1 - Y4 are each independently selected from CR, CR, or N, and at least one of Y1 - Y4 is selected from CR, where R is selected from substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or a combination thereof, and the number of carbon atoms of R is at least 5. a , CR a1 or N, and at least one of Y1 - Y4 is selected from CR a1 , where the R a1 is selected from substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or a combination thereof, and the R a1 has at least 5 carbon atoms; Y5-Y 16 each independently selected from CR y or N; each time it appears Said R, R’, R x , R y , R a , R t is each independently selected, when it appears each time, 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, R', R x , R y , R a , R t can optionally be linked to form a ring; preferably, the metal complex has a structure represented by Formula 1 - 1.
7. The metal complex according to claim 1 or 6, wherein X2 and X3 are C and are each connected to two "*", and X1 and X4 are each independently selected from CR x ; Preferably, said R x is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
8. The metal complex according to claim 1 or 6, wherein the n is selected from 1 or 2; Preferably, each occurrence of T, T1 and T2 is the same or different and is selected from C(R t )2, and each occurrence of said R t 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, and combinations thereof; More preferably, said R t is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
9. The metal complex according to claim 1 or 6, wherein each occurrence of T1 and / or T2 is the same or different and is selected from C(R t )2, and each occurrence of the said R t is the same or different and is selected from the group consisting of 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 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, and combinations thereof; More preferably, said R t is the same or different each time it appears and is selected from the group consisting of deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
10. The metal complex according to claim 6, wherein each occurrence of Y1 - Y4 is the same or different and is independently selected from CR a or CR a1 , and at least one of Y1 - Y4 is selected from CR a1 ; Preferably, the Y2 or Y3 is selected from CR a1 , the R a1 is selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, or a combination thereof, and the number of carbon atoms of the R a1 is at least 5; More preferably, said R a1 is selected from the group consisting of Ry-1 to Ry-53:
11. The metal complex according to claim 1 or 6, wherein the R has a structure represented by Formula 3: In Formula 3, "**” represents the connection position of Formula 3; Ring F, Ring G, and Ring N are each the same or different and are selected from unsaturated carbocycles having 5 - 30 carbon atoms, unsaturated heterocycles having 3 - 30 carbon atoms, or a combination thereof each time they appear; Z4 - Z7 are each the same or different and are selected from C or N each time they appear; R f ,R g ,R n which, each time it appears, is the same or different and represents mono-substitution, multi-substitution or no substitution; R f ,R g ,R n each occurrence of which 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, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R f ,R g ,R n may optionally be linked to form a ring; preferably, the R has the structure shown in Formula 3 - 1: In Formula 3 - 1, F1 to F5 are each independently selected from CR f or N; G1 to G5 are each independently selected from CR g or N; N1 to N3 are each independently selected from CR n or N; Said R f , R g , R n is the same as or different from each other each time it appears 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; Adjacent substituents R f , R g , R n can optionally be linked to form a ring; More preferably, each of F1 to F5 is independently selected from CR f , each of G1 to G5 is independently selected from CR g , each of N1 to N3 is independently selected from CR n , said R f , R g and R n is the same as or different from each other each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, 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, and combinations thereof.
12. The metal complex according to claim 1 or 6, wherein the L2 is selected from a single bond, O, S, (SiR’R’) y , NR’, (CR’R’) y , or a combination thereof; the y is 1 or 2; each occurrence of R’ is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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 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, and a combination thereof; preferably, the L2 is selected from a single bond, O, or S; more preferably, the L2 is selected from O.
13. The metal complex according to claim 6, wherein Y5-Y 16 is the same or different each time it appears and is selected from CR y ; Preferably, said R y is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, 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, and combinations thereof.
14. The metal complex according to claim 1, wherein the metal complex has the structure of Pt(L a )(L b ), where L a and L b are the first ligand and the second ligand coordinated to the metal Pt respectively, and the L a is selected from the group consisting of L a 1-1 to L a 1-63, L a 2-1 to L a 2-34, and L a 3-1 to L a 3-44: The "L" mentioned above a The "#" in the structure indicates the position where the "L" a structure is connected to the "L" b connection point; wherein the ligand L b selected from the group consisting of L b 1-1 to L b 1-33, L b 2-1 to L b 2-41, and L b 3-1 to L b 3-43: The L b in the structure indicates the position where the L b structure is connected to the "#" in L a ; Preferably, the metal complex is selected from the group consisting of metal complexes Pt1 to Pt597; the metal complexes Pt1 to Pt597 have the structure represented by Pt(L a )(L b ), and the L a and the L b are respectively selected from the structures shown in the following table:
15. An organic electroluminescent device, comprising: an anode, a 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 - 14.
16. The organic electroluminescent device according to claim 15, wherein the organic layer is a light-emitting layer and the metal complex is a light-emitting material.
17. The organic electroluminescent device according to claim 16, wherein the device emits blue light or white light.
18. The organic electroluminescent device according to claim 16, wherein the light-emitting layer comprises at least one host material; preferably, the light-emitting layer comprises at least two host materials; more preferably, the host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
19. A composition comprising the metal complex according to any one of claims 1-14.
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