Organic light-emitting device
By introducing alkyl metal complexes at specific locations of benzimidazole aromatic rings and combining high-triplet energy-level materials, the problem of insufficient performance of blue phosphorescent devices is solved, and higher quantum efficiency and better comprehensive performance are achieved.
Patent Information
- Application Number
- CN202310719331.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-06-16
- Publication Date
- 2024-12-17
AI Technical Summary
Existing blue phosphorescent light emitting devices have insufficient performance, especially in terms of quantum efficiency, lifetime and operating voltage, and lack of effective material combination solutions.
A metal complex with alkyl groups introduced at a specific position of the benzimidazole aromatic ring is used as a luminescent material and mixed with hole-transport and electron-transporting host materials with triplet energy levels higher than 2.69 eV to form a new type of organic electricity The luminescent layer material of the electroluminescent device.
It significantly improves the quantum efficiency and comprehensive performance of blue phosphorescence devices, improves the level of devices, and solves the problem of insufficient performance of traditional blue phosphorescence devices.
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Figure CN119156040A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic electronic device, such as an organic electroluminescent device. More particularly, it relates to an organic electroluminescent device comprising a first compound having a structure of Formula 1 and a first host material and a second host material having triplet energy levels higher than 2.69 eV in a light-emitting layer, and an electronic device comprising the organic electroluminescent device, and a compound composition comprising a first compound having a structure of Formula 1 and a first host material and a second host material having triplet energy levels higher than 2.69 eV. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: 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 devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-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 is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.
[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). 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 triplet to singlet. 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 based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.
[0006] There are various OLED manufacturing methods. 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. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.
[0008] US20190119312A1 discloses a metal complex, the general structure of which is: Specific compounds are disclosed in the device examples The metal complex is used as a compound of a light-emitting material and a single host The application does not disclose or teach the combination of the metal complex and the dual host material, and does not disclose or teach the application of the combination of the metal complex and the dual host material in an organic electroluminescent device.
[0009] US20220112231A1 discloses a light-emitting device, wherein the light-emitting layer contains a compound of the following general formula wherein CY1 to CY6 are each independently selected from C3-C 60 Carbon ring or C1-C 60 The heterocyclic ring disclosed is a metal complex of benzimidazole having a specific condensed ring structure, and the specific structure disclosed is the following structure: In the device embodiment, the metal complex is disclosed as a light-emitting material and a single host compound CBP is used in a light-emitting device. However, it does not disclose or teach the metal complex with a saturated group introduced at a specific position of benzimidazole, and does not disclose or teach the application of such a combination of a metal complex and a dual host material in an organic electroluminescent device.
[0010] US20230065887A1 discloses a metal complex having a general structure of Where R 1 ,R 2 ,R A ,R B ,R C ,R D and R E At least one of them is selected from Q(R 3 )(R 4 ) a (R) b , or Q is selected from C, Si, N, O or B. Although the following structure is disclosed in the specific structure: In the device embodiment, the metal complex is disclosed as a light-emitting material and as a host compound. It is applied in organic light-emitting devices. However, it does not teach that the metal complex with a specific aromatic group at the N position of benzimidazole can improve the device performance when used in combination with a high triplet dual host.
[0011] US20230117263A1 discloses a light-emitting device, wherein the light-emitting layer contains a compound of the following general structure Wherein ring A1, A2 and A3 are each independently a hydrocarbon ring of 5 to 60 carbon atoms, a heterocyclic ring of 1 to 60 carbon atoms, and A4 is selected from the following structures: R1 is selected from hydrogen, deuterium, halogen, alkyl, aryl, heteroaryl. and as the main material However, it does not focus on compounds in which the A4 ring is an unsaturated carbocyclic ring or a heteroaromatic ring, nor does it teach that compounds in which the A4 ring is an unsaturated carbocyclic ring or a heteroaromatic ring can improve device performance when used in combination with a high triplet dual host.
[0012] Currently, the performance of blue phosphorescent light-emitting devices still needs to be improved, such as higher quantum efficiency. Summary of the invention
[0013] The present invention aims to provide a novel organic electroluminescent device to solve at least part of the above problems. After in-depth research, the inventors have discovered a novel material combination, which introduces a metal complex with an alkyl group at a specific position of the benzimidazole aromatic ring as a luminescent material, and mixes a hole transport type host material with a triplet energy level higher than 2.69eV and an electron transport type host material with a triplet energy level higher than 2.69eV as a host material. This novel material combination can unexpectedly achieve better device performance, such as higher quantum efficiency, in a blue phosphorescent light-emitting device. These advantages are of great help in improving the level of blue light devices.
[0014] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0015] anode,
[0016] cathode,
[0017] and an organic layer disposed between the anode and the cathode comprises a light-emitting layer, the light-emitting layer comprising a first compound, a first host material and a second host material;
[0018] wherein the triplet energy levels of the first host material and the second host material are both higher than 2.69 eV;
[0019] Wherein the first compound has a structure represented by Formula 1:
[0020]
[0021] In Formula 1, Ring A and Ring D are selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or combinations thereof, the same or different when they appear each time; Ring B is selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, or heteroaromatic rings having 3 to 30 carbon atoms;
[0022] X1-X4 are selected from CR in the same or different way each time they appear.x , CR x1 or N, and at least one of X1-X4 is CR x1 ;
[0023] The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof;
[0024] The R x 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0025] The metal M is selected from metals with a relative atomic mass greater than 40;
[0026] L1, L2 are each independently selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof;
[0027] y is 1, 2, 3, 4, or 5;
[0028] K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S;
[0029] Z1-Z3 are selected from C or N at each occurrence, identically or differently;
[0030] R in Formula 1 has a structure represented by Formula 2:
[0031]
[0032] In Formula 2, Ring F, Ring G, and Ring N are each independently selected from an aromatic ring having 6 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof;
[0033] Z4-Z7 are selected, at each occurrence, identically or differently, from C or N;
[0034] R a , R b , R d , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted;
[0035] R', R a , R b , R d , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0036] The adjacent substituents R', R a , R d , R n can optionally be linked to form a ring;
[0037] “*” indicates the connection position of Formula 2.
[0038] According to another embodiment of the present invention, an electronic device is disclosed, which includes the organic electroluminescent device as described above.
[0039] According to another embodiment of the present invention, a compound composition is disclosed, which at least includes a first compound, a first host material and a second host material.
[0040] The present invention discloses a novel organic electroluminescent device, wherein a novel material combination consisting of a first compound, a first host material and a second host material is used in the organic electroluminescent device, and the novel material combination can be used in the light-emitting layer of the electroluminescent device. The novel material combination can exhibit excellent comprehensive device performance in the device, such as higher quantum efficiency. BRIEF DESCRIPTION OF THE DRAWINGS
[0041] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent device disclosed herein.
[0042] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0043] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.
[0044] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.
[0045] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.
[0046] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
[0047] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0048] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.
[0049] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0050] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.
[0051] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0052] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
[0053] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0054] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable 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 by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.
[0055] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the 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 by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).
[0056] Definition of Substituent Terms
[0057] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0058] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-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. In addition, the alkyl group may be optionally substituted.
[0059] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl 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. In addition, cycloalkyl can be optionally substituted.
[0060] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.
[0061] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 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-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.
[0062] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 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, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.
[0063] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.
[0064] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.
[0065] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.
[0066] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. 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, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.
[0067] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.
[0068] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,
[0069] 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.
[0070] 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.
[0071] 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.
[0072] 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.
[0073] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0074] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, Substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups refer to any one of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylgermanyl groups, arylgermanyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups and phosphino groups, which may be substituted by one or more of deuterium, halogen groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, Cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl 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 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0075] It should be understood that when describing a molecular fragment 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 a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.
[0076] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
[0077] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.
[0078] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, 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.
[0079] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0080]
[0081] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0082]
[0083] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0084]
[0085] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0086]
[0087] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0088] anode,
[0089] cathode,
[0090] and an organic layer disposed between the anode and the cathode comprises a light-emitting layer, the light-emitting layer comprising a first compound, a first host material and a second host material;
[0091] wherein the triplet energy levels of the first host material and the second host material are both higher than 2.69 eV;
[0092] Wherein the first compound has a structure represented by Formula 1:
[0093]
[0094] In Formula 1, Ring A and Ring D are selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or combinations thereof, the same or different when they appear each time; Ring B is selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, or heteroaromatic rings having 3 to 30 carbon atoms;
[0095] X1-X4 are selected from CR in the same or different way each time they appear. x , CR x1 or N, and at least one of X1-X4 is CR x1 ;
[0096] The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof;
[0097] The R xThe group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0098] The metal M is selected from metals with a relative atomic mass greater than 40;
[0099] L1, L2 are each independently selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof;
[0100] y is 1, 2, 3, 4, or 5;
[0101] K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S;
[0102] Z1-Z3 are selected from C or N at each occurrence, identically or differently;
[0103] R in Formula 1 has a structure represented by Formula 2:
[0104]
[0105] In Formula 2, Ring F, Ring G, and Ring N are each independently selected from an aromatic ring having 6 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof;
[0106] Z4-Z7 are selected, at each occurrence, identically or differently, from C or N;
[0107] R a , R b , R d , Rf , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted;
[0108] R', R a , R b , R d , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0109] The adjacent substituents R', R a , R d , R n can optionally be linked to form a ring;
[0110] “*” indicates the connection position of Formula 2.
[0111] Herein, the “unsaturated carbocycle having 5 to 30 carbon atoms” includes aromatic unsaturated carbocycles and non-aromatic unsaturated carbocycles having 5 to 30 carbon atoms; and the “unsaturated heterocycle having 3 to 30 carbon atoms” includes aromatic unsaturated heterocycles and non-aromatic unsaturated heterocycles having 3 to 30 carbon atoms.
[0112] Herein, "Ring B is selected identically or differently each time it occurs from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms" indicates that Ring B is an unsaturated carbocyclic ring having aromaticity, or an unsaturated carbocyclic ring not having aromaticity, or a heterocyclic ring having aromaticity. Thus, a heterocyclic ring not having aromaticity, for example It is not within the scope of Ring B defined in this application.
[0113] In this context, adjacent substituents R', R a , R d , R n can be optionally connected to form a ring, which is intended to indicate adjacent substituent groups, for example, between two substituents R', between two substituents R a Between the two substituents R d Between the two substituents R n Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring. According to one embodiment of the present invention, the adjacent substituent groups R f , R g Cannot connect to form a ring.
[0114] In this context, adjacent substituents R f , R g cannot be connected to form a ring, and is intended to indicate that adjacent substituent groups, for example, two substituents R f Between the two substituents R g These adjacent substituent groups are not connected to form a ring.
[0115] According to one embodiment of the present invention, the M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.
[0116] According to one embodiment of the present invention, the M is selected from Pt or Pd.
[0117] According to one embodiment of the present invention, wherein the M is selected from Pt.
[0118] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms.
[0119] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms.
[0120] According to one embodiment of the present invention, the ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolecarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, a benzofurancarbazole ring, or a benzimidazole and benzimidazole ring.
[0121] According to one embodiment of the present invention, wherein said L1 is selected from a single bond, O, S, (SiR'R') y , NR', or a combination thereof.
[0122] According to one embodiment of the present invention, wherein said L1 is selected from a single bond, O or S.
[0123] According to one embodiment of the present invention, wherein said L1 is selected from a single bond.
[0124] According to one embodiment of the present invention, wherein said K1-K4 is selected from a single bond.
[0125] According to one embodiment of the present invention, Z1 is selected from N, and Z2 and Z3 are selected from C.
[0126] According to one embodiment of the present invention, the first compound has a structure represented by one of Formula 1-1 to Formula 1-7:
[0127]
[0128] L2 is selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', substituted or unsubstituted arylene having 6 to 30 carbon atoms, or a combination thereof;
[0129] y is 1, 2, 3, 4, or 5;
[0130] X1-X4 are selected from CR in the same or different way each time they appear. x , CR x1 or N, and at least one of X1-X4 is CR x1 ;
[0131] In Formulas 1-1 to 1-3, 1-5 to 1-7, Y a1 -Y a4 Each time it appears, the same or different selection is made from CR ya or N; in formula 1-4, Y a1 and Y a2 Each time it appears, the same or different selection is made from CR ya or N;
[0132] In Formula 1-1, Formula 1-5, Formula 1-6 and Formula 1-7, Y b1 -Y b6 Each time it appears, the same or different selection is made from CR yb or N; in Formula 1-2 and Formula 1-4, Y b1 -Y b3 Each time it appears, the same or different selection is made from CR yb or N; in formula 1-3, Y b1 -Y b9 Each time it appears, the same or different selection is made from CR yb or N;
[0133] In Formula 1-1 to Formula 1-7, Y d1 -Y d3 Each time it appears, the same or different selection is made from CR yd or N;
[0134] The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof;
[0135] R has the structure shown in formula 2-1:
[0136]
[0137] In Formula 2-1, 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;
[0138] The R', R", R x , R ya , R yb , R yd , R f , R g , R nThe group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0139] The adjacent substituents R', R n , R ya , R yd Can optionally be linked to form a ring.
[0140] In this context, adjacent substituents R', R n , R ya , R yd can be optionally connected to form a ring, which is intended to indicate adjacent substituent groups, for example, between two substituents R', between two substituents R n Between the two substituents R ya Between the two substituents R yd Any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, these adjacent substituent groups can also not be connected to form a ring.
[0141] According to an embodiment of the present invention, at least one of N1 to N3 is CR n , the R nselected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl 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 cycloalkyl ... atom, an alkynyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof. According to one embodiment of the present invention, wherein said R x1 Each occurrence is identically or differently selected from the group consisting of methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, and combinations thereof.
[0142] According to one embodiment of the present invention, X3 is selected from CR x1 ;
[0143] The R x1 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1-7 carbon atoms, substituted or unsubstituted cycloalkyl having 3-8 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-7 carbon atoms, and combinations thereof.
[0144] According to one embodiment of the present invention, X3 is selected from CR x1 ;
[0145] The R x1Each occurrence is identically or differently selected from the group consisting of methyl, deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, and combinations thereof.
[0146] According to one embodiment of the present invention, wherein R', R", R x , R ya , R yb , R yd , R f , R g , R n Each occurrence is identically or differently 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.
[0147] According to one embodiment of the present invention, wherein R', R", R x , R ya , R yb , R yd , R f , R g , R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.
[0148] According to one embodiment of the present invention, each time R appears, it is identically or differently selected from the group consisting of An-1 to An-55, and the specific structures of An-1 to An-55 are shown in claim 10.
[0149] According to one embodiment of the present invention, the hydrogen in the structures of An-1 to An-55 can be partially or completely replaced by deuterium.
[0150] According to one embodiment of the present invention, the first compound has Pt(L a )(L b ) represents the structure, L a and L b are the first ligand and the second ligand coordinated with the metal Pt, respectively. a Choose from L a 1-1 to L a 1-22, L a 2-1 to L a 2-19, and L a 3-1 to L a For a group consisting of 3-13 people, the L b Choose from L b 1-1 to L b 1-8, L b 2-1 to L b 2-22, L b 3-1 to L b For a group consisting of 3-13 people, the L a 1-1 to L a 1-22, L a 2-1 to L a 2-19, and L a 3-1 to L a 3-13, L b 1-1 to L b 1-8, L b 2-1 to L b 2-22, L b 3-1 to L b The specific structure of 3-13 is shown in claim 11.
[0151] According to one embodiment of the present invention, the first compound is selected from the group consisting of compound Pt1 to compound Pt198, and the specific structures of compound Pt1 to compound Pt198 are shown in claim 11.
[0152] According to one embodiment of the present invention, the triplet energy level of the first host material is higher than 2.69 eV and has
[0153] The structure represented by any one of Formula 3 to Formula 4:
[0154]
[0155] In Formula 3, U1 to U3 are selected from CR4 or N at each occurrence, the same or different, and at least one of U1 to U3 is N;
[0156] L3 is identically or differently selected at each occurrence from the group consisting of 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, and combinations thereof;
[0157] In Formula 4, each occurrence of U4 is identically or differently selected from CR4 or N, and at least one U4 is N;
[0158] Z is selected from O, S or NR5;
[0159] R1 to R5 are selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0160] Adjacent substituents R4 can be optionally linked to form a ring.
[0161] In this article, adjacent substituents R4 can be optionally connected to form a ring, which is intended to mean that any two substituents R4 can be connected to form a ring. Obviously, any two substituents R4 may not be connected to form a ring.
[0162] According to one embodiment of the present invention, R5 is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a combination thereof.
[0163] According to one embodiment of the present invention, the triplet energy level of the first host material is higher than 2.69 eV and has
[0164] The structure represented by formula 4-1:
[0165]
[0166] In formula 4-1,
[0167] Z is selected from O or S;
[0168] U 41 -U 48 Each occurrence is identically or differently selected from CR4, CR4' or N, and U 41 -U 48 At least one of them is selected from N, and at least one of them is selected from CR4';
[0169] The R4' is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or a combination thereof, at each occurrence, the same or different;
[0170] U 41 '-U 48 ',U 41 ”-U 45 " is selected identically or differently at each occurrence from CR4 or N;
[0171] R4 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0172] Adjacent substituents R4 can be optionally linked to form a ring.
[0173] According to one embodiment of the present invention, in Formula 4-1, the U 41 -U 48At least one of them is selected from N, and at least two of them are selected from CR4'.
[0174] According to one embodiment of the present invention, in Formula 4-1, the U 41 -U 48 Only one of them is selected from N and only two of them are selected from CR4'.
[0175] According to one embodiment of the present invention, in Formula 4-1, the U 42 Selected from N, U 41 and U 46 Selected from CR4'.
[0176] According to one embodiment of the present invention, the triplet energy level of the first host material is higher than 2.69 eV and has
[0177] The structure represented by any one of Formula 4-1-1 to Formula 4-1-4:
[0178]
[0179] U 41 toU 48 Each occurrence is identically or differently selected from CR4 or N, and U 41 toU 48 At least one of them is N;
[0180] Z is selected from O or S;
[0181] R4 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0182] Adjacent substituents R4 can be optionally linked to form a ring.
[0183] According to an embodiment of the present invention, in Formula 3, at least two of U1 to U3 are N.
[0184] According to an embodiment of the present invention, in Formula 3, U1 to U3 are N.
[0185] According to one embodiment of the present invention, in Formula 3, L3 is selected from the group consisting of: a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and combinations thereof, at each occurrence thereof.
[0186] According to one embodiment of the present invention, in Formula 3, L3 is selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a fluorenyl group, a triphenylene group, a furanyl group, a thienyl group, a dibenzofuranyl group, a dibenzothienyl group, and combinations thereof, the same or different each time it appears.
[0187] According to one embodiment of the present invention, each time R1 to R5 appears, they are identically or differently 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, and combinations thereof.
[0188] According to one embodiment of the present invention, each time R1 to R5 appears, they are identically or differently 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.
[0189] According to one embodiment of the present invention, each time R1 to R5 appears, they are selected from the group consisting of hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiole, dibenzothiole, benzothiophene, dibenzothiophene, dibenzoselenophene, triazine, and combinations thereof.
[0190] According to one embodiment of the present invention, the first main material is selected from the group consisting of compound N-1-1 to compound N-1-53, compound N-2-1 to compound N-2-32, and compound N-3-1 to compound N-3-11; the specific structures of compound N-1-1 to compound N-1-53, compound N-2-1 to compound N-2-32, and compound N-3-1 to compound N-3-11 are shown in claim 16.
[0191] According to one embodiment of the present invention, the hydrogen in the structures of the compounds N-1-1 to N-1-53, N-2-1 to N-2-32, and N-3-1 to N-3-11 can be partially or completely replaced by deuterium.
[0192] According to one embodiment of the present invention, the triplet energy level of the second host material is higher than 2.69 eV and has a structure represented by Formula 5:
[0193]
[0194] In formula 5,
[0195] L4 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;
[0196] Ar1 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 20 carbon atoms, or a combination thereof;
[0197] R6, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution;
[0198] R6 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0199] Adjacent substituents R6 can be optionally linked to form a ring.
[0200] In this article, adjacent substituents R6 can be optionally connected to form a ring, which is intended to mean that any adjacent substituents R6 can be connected to form a ring. Obviously, any adjacent substituents R6 may not be connected to form a ring.
[0201] According to one embodiment of the present invention, the triplet energy level of the second host material is higher than 2.69 eV and has
[0202] The structure represented by Formula 5-1 or Formula 5-2:
[0203]
[0204] L4, L5 are each independently 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;
[0205] Ar1 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 20 carbon atoms, or a combination thereof;
[0206] R6, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution;
[0207] R6 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0208] Adjacent substituents R6 can be optionally linked to form a ring.
[0209] According to one embodiment of the present invention, the triplet energy level of the second host material is higher than 2.69 eV and has
[0210] The structure represented by Formula 5-3 or Formula 5-4:
[0211]
[0212] Ar1 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;
[0213] L4 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;
[0214] R6, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution;
[0215] R6 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0216] Adjacent substituents R6 can be optionally linked to form a ring.
[0217] According to one embodiment of the present invention, wherein said R6 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 at each occurrence.
[0218] According to one embodiment of the present invention, wherein said R6 is identically or differently 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 at each occurrence.
[0219] According to one embodiment of the present invention, wherein said R6 is selected from the group consisting of hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiole, dibenzothiole, benzothiophene, dibenzothiophene, dibenzoselenophene, and combinations thereof, in each occurrence, the same or different.
[0220] According to one embodiment of the present invention, the second host material is selected from the group consisting of compound P-1 to compound P-32, and the specific structures of compound P-1 to compound P-32 are shown in claim 20.
[0221] According to one embodiment of the present invention, the hydrogen in the structures of the compounds P-1 to P-32 can be partially or completely replaced by deuterium.
[0222] According to one embodiment of the present invention, the triplet energy levels of the first host material and the second host material are both higher than 2.77 eV.
[0223] According to an embodiment of the present invention, the first compound is a phosphorescent light-emitting material, the first host material is an n-type host material, and the second host material is a p-type host material.
[0224] According to an embodiment of the present invention, the organic electroluminescent device emits blue light.
[0225] According to another embodiment of the present invention, an electronic device is disclosed, which includes the organic electroluminescent device as described in any of the above embodiments.
[0226] According to another embodiment of the present invention, a compound composition is also disclosed, which includes a first compound, a first host material, and a second host material;
[0227] wherein the triplet energy levels of the first host material and the second host material are both higher than 2.69 eV;
[0228] The first compound has a structure represented by Formula 1:
[0229]
[0230] In Formula 1, Ring A and Ring D are each independently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; Ring B is selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;
[0231] X1-X4 are selected from CR in the same or different way each time they appear. x , CR x1 or N, and at least one of X1-X4 is CR x1 ;
[0232] The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof;
[0233] The R x 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0234] The metal M is selected from metals with a relative atomic mass greater than 40;
[0235] L1, L2 are each independently selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof;
[0236] y is 1, 2, 3, 4, or 5;
[0237] K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S;
[0238] Z1-Z3 are selected from C or N at each occurrence, identically or differently;
[0239] R in Formula 1 has a structure represented by Formula 2:
[0240]
[0241] In Formula 2, Ring F, Ring G, and Ring N are each independently selected from an aromatic ring having 6 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof;
[0242] Z4-Z7 are selected, at each occurrence, identically or differently, from C or N;
[0243] R a, R b , R d , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted;
[0244] R', R a , R b , R d , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0245] The adjacent substituents R', R a , R d , R n can optionally be linked to form a ring;
[0246] “*” indicates the connection position of Formula 2.
[0247] Combination with other materials
[0248] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.
[0249] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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.
[0250] Determination of triplet energy levels:
[0251] The triplet energy level (T1) is measured at ultra-low temperature using the characteristics of triplet excitons with a long lifetime. Specifically, the compound to be tested is dissolved in 2-methyltetrahydrofuran solvent to prepare 10 -5 The solution is placed in a quartz sample tube and then placed in a Dewar flask and cooled to 77 K. The solution of the compound to be tested is irradiated with a 350 nm light source to measure the phosphorescence spectrum. The spectrum is measured using a spectrophotometer model F98 produced by Shanghai Lingguang Technology Co., Ltd.
[0252] The phosphorescence spectrum has a vertical axis representing phosphorescence intensity and a horizontal axis representing wavelength. After taking the minimum value λ1 (nm) relative to the peak on the short wavelength side of the phosphorescence spectrum, the wavelength value is substituted into the following conversion formula F1 to calculate the triplet energy.
[0253] Conversion formula F1: T1 (eV) = 1240 / λ1
[0254] The triplet energy levels T1 (eV) of the following compounds were measured by the above method. The specific results are shown in Table 1.
[0255] Table 1 Triplet energy level data of compounds
[0256] Compound No. <![CDATA[T1(eV)]]> P-24 2.95 N-1-15 2.89
[0257] The material structure used in the triplet energy level data test is shown below:
[0258]
[0259] It can be seen from the data in Table 1 that the triplet energy levels of the first host material and the second host material of the present invention are both higher than 2.69 eV, and such materials can be used as excellent host materials in blue phosphorescent devices. Device examples are provided below for verification.
[0260] In the example of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.
[0261] Material synthesis example:
[0262] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:
[0263] Synthesis Example 1: Synthesis of Compound Pt16
[0264] Step 1: Synthesis of Intermediate 1
[0265]
[0266] Under nitrogen, 2,6-dibromoaniline (7.4 g, 29.5 mmol), phenyl-D5-boric acid (10.4 g, 70.8 mmol), Pd(PPh3)4 (1.7 g, 1.5 mmol) and potassium carbonate (16.3 g, 118.0 mmol) were dissolved in (toluene: ethanol: water = 4:1:1) for a total of 145 mL, heated to reflux, and reacted overnight. After the reaction was complete, it was extracted with dichloromethane and water, the organic layer was washed several times with sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, and column chromatography was performed to obtain intermediate 1 (4.7 g, 18.4 mmol).
[0267] Step 2: Synthesis of Intermediate 2
[0268]
[0269] Under nitrogen conditions, intermediate 1 (6.3 g, 24.7 mmol), 3-bromo-4-nitro-tert-butylbenzene (9.11 g, 35.2 mmol), Pd(OAc)2 (2.3 g, 2.47 mmol), S-Phos (2.0 g, 4.9 mmol), NaOt-Bu (4.7 g, 49.4 mmol) and toluene (125 mL) were added to a flask. The reaction was heated to 115°C and stirred overnight. The mixture was cooled to room temperature, and the solvent was removed and then column chromatography was used to obtain intermediate 2 (7.4 g, 17.1 mmol).
[0270] Step 3: Synthesis of Intermediate 3
[0271]
[0272] Intermediate 2 (7.4 g, 17.1 mmol) was dissolved in EtOH (30 mL) and water (30 mL), iron powder (5.7 g, 102.0 mmol) and NH4Cl (5.4 g, 101.9 mmol) were added, the reaction temperature was raised to reflux, and the reaction was allowed to react overnight. After the reaction was complete, the mixture was filtered through diatomaceous earth, evaporated to dryness under reduced pressure, and extracted with ethyl acetate (EA) and water. The organic layer was washed twice with sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Intermediate 3 (5.1 g, 12.6 mmol) was obtained by column chromatography.
[0273] Step 4: Synthesis of intermediate 4
[0274]
[0275] Under nitrogen conditions, 2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (7.0 g, 18.0 mmol), m-chlorophenol (3.0 g, 23.3 mmol), cuprous iodide (0.34 g, 1.8 mmol), 2-picolinic acid (0.44 g, 3.6 mmol) and potassium phosphate (7.6 g, 36.0 mmol) were added to a 500 mL flask, and dimethyl sulfoxide (72 mL) was added. The reaction was heated to 150° C. and stirred overnight. After the reaction was completed, it was purified by column chromatography to obtain intermediate 4 (5.6 g, 13.1 mmol).
[0276] Step 4: Synthesis of Intermediate 5
[0277]
[0278] Under nitrogen conditions, intermediate 3 (5.1 g, 12.6 mmol), intermediate 4 (5.6 g, 13.1 mmol), Pd(OAc)2 (141.1 mg, 0.63 mmol), S-Phos (516.6 mg, 1.3 mmol), NaOt-Bu (2.4 g, 25.2 mmol) and xylene (77 mL) were added to a flask, the reaction was heated to 140°C and stirred overnight, cooled to room temperature, and the solvent was removed and then intermediate 5 (7.0 g, 8.8 mmol) was obtained by column chromatography.
[0279] Step 5: Synthesis of Intermediate 6
[0280]
[0281] Under nitrogen conditions, intermediate 5 (7.0 g, 8.8 mmol), triethyl orthoformate (70.0 g, 472.9 mmol) and concentrated HCl (1.3 mL) were added to a flask. The reaction was heated to 100°C and stirred overnight. After the reaction was completed, it was detected by TLC. The mixture was cooled to room temperature, the solvent was removed, and intermediate 6 (5.0 g, 6.0 mmol) was obtained by column chromatography.
[0282] Step 6: Synthesis of compound Pt16
[0283]
[0284] Under nitrogen, intermediate 6 (5.0 g, 6.0 mmol), Ag2O (0.7 g, 3.0 mmol), and DCE (60 mL) were added to a flask and reacted at room temperature for 12 h. After the reaction was complete, the solvent was removed under reduced pressure, (1,5-cyclooctadiene) platinum dichloride (2.2 g, 6.0 mmol) was added, and o-dichlorobenzene (60 mL) was added. The reaction temperature was raised to 190 ° C and stirred for 72 h. After the reaction was cooled to room temperature, compound Pt16 (4.5 g, 4.5 mmol) was obtained by column chromatography. The product was identified as the target product with a molecular weight of 995.4.
[0285] Synthesis Example 2: Synthesis of Compound Pt27
[0286] Step 1: Synthesis of intermediate 7
[0287]
[0288] Under nitrogen, 2,6-dibromo-4-tert-butylaniline (10.0 g, 32.8 mmol), phenyl-D5-boric acid (9.9 g, 78.0 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol) and potassium carbonate (18.0 g, 130.4 mmol) were dissolved in (toluene: ethanol: water = 4:1:1) for a total of 165 mL, heated to reflux, and reacted overnight. After the reaction was complete, it was extracted with dichloromethane and water, the organic layer was washed several times with sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, and column chromatography was performed to obtain intermediate 7 (7.0 g, 22.5 mmol).
[0289] Step 2: Synthesis of intermediate 8
[0290]
[0291] Under nitrogen conditions, intermediate 7 (7.0 g, 22.5 mmol), 3-bromo-4-nitro-tert-butylbenzene (8.6 g, 33.3 mmol), Pd(OAc)2 (253 mg, 1.1 mmol), S-Phos (944 mg, 2.3 mmol), NaOt-Bu (4.5 g, 46.9 mmol) and toluene (117 mL) were added to a flask. The reaction was heated to 115°C and stirred overnight. The mixture was cooled to room temperature, and the solvent was removed and then column chromatography was used to obtain intermediate 8 (10.0 g, 20.5 mmol).
[0292] Step 3: Synthesis of intermediate 9
[0293]
[0294] Intermediate 8 (10.0 g, 20.5 mmol) was dissolved in EtOH (50 mL) and water (50 mL), iron powder (3.3 g, 58.9 mmol) and NH4Cl (10.4 g, 196.2 mmol) were added, the reaction was heated to reflux, and the reaction was allowed to proceed overnight. After the reaction was complete, the mixture was filtered through diatomaceous earth, the solvent was removed under reduced pressure, and then extracted with EA and water. The organic layer was washed twice with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain intermediate 9 (6.0 g, 13.1 mmol).
[0295] Step 4: Synthesis of intermediate 10
[0296]
[0297] Under nitrogen conditions, intermediate 9 (6.0 g, 13.1 mmol), intermediate 4 (5.6 g, 13.1 mmol), Pd(OAc)2 (146.7 mg, 0.66 mmol), X-Phos (624.4 mg, 1.3 mmol), Cs2CO3 (8.5 g, 26.1 mmol) and xylene (65 mL) were added to a flask, the reaction was heated to 140°C and stirred overnight, cooled to room temperature, and the solvent was removed and then intermediate 10 (8.6 g, 10.1 mmol) was obtained by column chromatography.
[0298] Step 5: Synthesis of intermediate 11
[0299]
[0300] Under nitrogen conditions, intermediate 10 (8.6 g, 10.1 mmol), triethyl orthoformate (86.0 g, 581.0 mmol) and concentrated hydrochloric acid (1.5 mL) were added to a flask. The reaction was heated to 100 °C and stirred overnight. After the reaction was completed by TLC, the mixture was cooled to room temperature. After removing the solvent, intermediate 11 (7.2 g, 8.1 mmol) was obtained by column chromatography.
[0301] Step 6: Synthesis of compound Pt27
[0302]
[0303] Under nitrogen conditions, intermediate 11 (7.2 g, 8.1 mmol), Ag2O (0.94 g, 4.1 mmol), and DCE (20 mL) were added to a flask and reacted at room temperature for 12 h. After the reaction was complete, the solvent was removed under reduced pressure, (1,5-cyclooctadiene) platinum dichloride (3.0 g, 8.1 mmol) was added, and o-dichlorobenzene (81 mL) was added. The reaction temperature was raised to 190 ° C and stirred for 72 h. After the reaction was cooled to room temperature, compound Pt27 (5.1 g, 4.9 mmol) was obtained by column chromatography. The product was identified as the target product with a molecular weight of 1051.4.
[0304] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0305] Device Example 1
[0306] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -7 Compound HT and compound HI were co-deposited (weight ratio 97:3) as a hole injection layer (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound P-21 was used as an electron blocking layer (EBL) with a thickness of Then, the compound N-1-15 as the first host, the compound P-24 as the second host, and the first compound Pt16 as the dopant were co-evaporated (weight ratio 26.4:61.6:12) to serve as the light-emitting layer (EML) with a thickness of Compound N-1-15 was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated (weight ratio 40:60) as an electron transport layer (ETL) with a thickness of Finally, evaporation LiF with a thickness of 1000 nm was used as an electron injection layer, and the The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture getter to complete the device.
[0307] Device Example 2
[0308] The implementation of Device Example 2 is the same as that of Device Example 1, except that Compound Pt27 is used instead of Compound Pt16 in the light emitting layer (EML).
[0309] Device Comparison Example 1
[0310] The implementation of Comparative Device Example 1 is the same as that of Example 1, except that the compound Pt-A is used instead of the compound Pt16 in the light emitting layer (EML).
[0311] Device Comparison Example 2
[0312] The implementation method of device comparison example 2 is the same as that of device example 1, except that compound P-24 is used instead of compound P-24 and compound N-1-15 as the main material in the light-emitting layer (EML), and is co-evaporated with compound Pt16 as the light-emitting layer (the weight ratio of compound P-24 and compound Pt16 is 88:12).
[0313] Device Comparison Example 3
[0314] The implementation method of device comparison example 3 is the same as that of device example 1, except that compound N-1-15 is used as the main material instead of compound P-24 and compound N-1-15 in the light-emitting layer (EML), and is co-evaporated with compound Pt16 as the light-emitting layer (the weight ratio of compound N-1-15 and compound Pt16 is 88:12).
[0315] Device Comparison Example 4
[0316] The implementation method of device comparison example 4 is the same as that of device example 1, except that compound H-1 is used as the main material instead of compound P-24 and compound N-1-15 in the light-emitting layer (EML), and is co-evaporated with compound Pt16 as the light-emitting layer (the weight ratio of compound H-1 and compound Pt16 is 88:12).
[0317] Device Comparison Example 5
[0318] The implementation method of device comparison example 5 is the same as that of device comparison example 1, except that compound P-24 is used instead of compound P-24 and compound N-1-15 as the main material in the light-emitting layer (EML), and is co-evaporated with compound Pt-A as the light-emitting layer (the weight ratio of compound P-24 and compound Pt-A is 88:12).
[0319] Device Comparison Example 6
[0320] The implementation method of device comparison example 6 is the same as that of device comparison example 1, except that compound N-1-15 is used as the main material instead of compound P-24 and compound N-1-15 in the light-emitting layer (EML), and is co-evaporated with compound Pt-A as the light-emitting layer (the weight ratio of compound N-1-15 and compound Pt-A is 88:12).
[0321] Device Comparison Example 7
[0322] The implementation method of device comparison example 7 is the same as that of device comparison example 1, except that compound H-1 is used as the main material instead of compound P-24 and compound N-1-15 in the light-emitting layer (EML), and is co-evaporated with compound Pt-A as the light-emitting layer (the weight ratio of compound H-1 and compound Pt-A is 88:12).
[0323] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0324] Table 2 Partial device structures of device embodiments and comparative examples
[0325]
[0326]
[0327] The material structure used in the device is shown below:
[0328]
[0329]
[0330] At 10mA / cm 2 The CIE values of Examples 1-2 and Comparative Examples 1-7 were measured, and the maximum emission wavelength (λ max ), external quantum efficiency (EQE). The relevant data are shown in Table 3.
[0331] Table 3 Device data
[0332]
[0333] discuss:
[0334] From the data in Table 3, it can be seen that the maximum emission wavelengths of the embodiment and the comparative example are substantially consistent, and the embodiment has excellent device performance relative to the comparative example, specifically:
[0335] Examples 1 and 2 respectively use the first compounds Pt16 and Pt27 selected by the present invention with specific substitution structures at specific positions and the specific combination of the first host material and the second host material selected by the present invention. Comparative Example 1 uses the compound Pt-A without specific substitution structures and the combination of the first host material and the second host material selected by the present invention. Compared with the already high EQE level of Comparative Example 1, the EQE of Example 1 is significantly improved by 8.7%, and the EQE of Example 2 is more significantly improved by 16.2%. These data show that the combination of the first compound, the first host material and the second host material selected by the present invention can significantly improve the external quantum efficiency of the device compared with the combination of the first host material, the second host material selected by the present invention and the first compound not belonging to the present invention, proving that the compound combination selected by the present invention is an excellent material combination.
[0336] Example 1 uses the first compound Pt16 selected by the present invention and the specific combination of the first host material and the second host material selected by the present invention. Comparative Examples 2 and 3 respectively use the first compound Pt16 selected by the present invention and the second host material of the present invention as a combination of a single host, and the first compound Pt16 selected by the present invention and the first host material of the present invention as a combination of a single host. Compared with Comparative Examples 2 and 3, the EQE of Example 1 is greatly improved by 149.0% and 43.9%, respectively. Comparative Example 4 uses the first compound Pt16 selected by the present invention and compound H-1 as a combination of a single host. Compared with Comparative Example 4, the EQE of Example 1 is greatly improved by 93.0%. These data once again illustrate that the specific combination of the first compound, the first host material, and the second host material selected by the present invention is an excellent combination of materials, which can obtain extremely excellent device performance.
[0337] Comparative Example 5 uses the second host material P-24 selected by the present invention as a combination of a single host and a compound Pt-A that does not belong to the present invention, and Comparative Example 6 uses the first host material N-1-15 selected by the present invention as a combination of a single host and a compound Pt-A that does not belong to the present invention. Compared with Comparative Example 1, the EQE of Comparative Examples 5 and 6 are greatly improved by 126.7% and 42.2%, respectively. Compared with Comparative Example 1, the embodiment uses the first compound selected by the present invention, the combination of the first host material and the second host material, and the EQE of the embodiment 1 is further improved, and extremely excellent device performance can be obtained. These data once again illustrate that the specific combination of the first compound, the first host material, and the second host material selected by the present invention is an excellent material combination, which can obtain extremely excellent device performance.
[0338] Comparative Example 7 uses the combination of compound Pt-A and compound H-1 which are not selected by the present invention as a single host, and Comparative Example 4 uses the combination of the first compound Pt16 and compound H-1 selected by the present invention as a single host. Compared with Comparative Example 7, the EQE of Comparative Example 4 is slightly improved. Example 1 uses the first compound Pt16 selected by the present invention, and Comparative Example 1 uses Pt-A. Compared with Comparative Example 1, Example 1 obtains a significantly improved external quantum efficiency of the device. This shows that the specific combination of the first compound, the first host material, and the second host material selected by the present invention is an excellent combination of materials.
[0339] In summary, the first compound selected by the present invention, which introduces a specific substituent on the imidazole-fused aromatic ring of Formula 1, and the novel material combination consisting of the first host material and the second host material having triplet energy levels higher than 2.69 eV, are used in blue light phosphorescent electroluminescent devices to obtain a higher EQE. These advantages are of great help in improving the level of blue light devices. It is proved that the combination of the first host material, the second host material selected by the present invention and the first compound selected by the present invention has excellent application prospects.
[0340] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific 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 about why the present invention works are not intended to be restrictive.
Claims
1. An organic electroluminescent device, comprising: anode, cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising a first compound, a first host material and a second host material; wherein the triplet energy levels of the first host material and the second host material are both higher than 2.69 eV; Wherein the first compound has a structure represented by Formula 1: In Formula 1, Ring A and Ring D are each independently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; Ring B is selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; X1-X4 are selected from CR in the same or different ways each time they appear x , CR x1 or N, and at least one of X1-X4 is selected from CR x1 ; The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof; The R x 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The metal M is selected from metals with a relative atomic mass greater than 40; L1, L2 are each independently selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4, or 5; K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S; Z1-Z3 are selected from C or N at each occurrence, identically or differently; R in Formula 1 has a structure represented by Formula 2: In Formula 2, Ring F, Ring G, and Ring N are each independently selected from an aromatic ring having 6 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; Z4-Z7 are selected, at each occurrence, identically or differently, from C or N; R a , R b , R d , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted; R', R a , R b , R d , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The adjacent substituents R', R a , R d , R n can optionally be linked to form a ring; "*" indicates the connection position of Formula 2.
2. The organic electroluminescent device according to claim 1, wherein M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; Preferably, M is selected from Pt or Pd; More preferably, M is selected from Pt.
3. The organic electroluminescent device according to claim 1, wherein ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a five-membered unsaturated carbon ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; Preferably, ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms; More preferably, ring A, ring B, ring D, ring F, ring G and ring N are each independently selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolecarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, a benzofuranocarbazole ring, or a benzimidazole and benzimidazole ring.
4. The organic electroluminescent device according to claim 1, wherein L1 is selected from a single bond, O, S, (SiR'R') y , NR', or a combination thereof; Preferably, L1 is selected from a single bond, O or S; More preferably, L1 is selected from a single bond. The organic electroluminescent device as claimed in claim 1 , wherein K1 to K4 are selected from single bonds. The organic electroluminescent device as claimed in claim 1 , wherein Z1 is selected from N, and Z2 and Z3 are selected from C. 7 .
7. The organic electroluminescent device according to claim 1, wherein: The first compound has a structure represented by one of Formula 1-1 to Formula 1-7: L2 is selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4, or 5; X1-X4 are selected from CR in the same or different ways each time they appear x , CR x1 or N, and at least one of X1-X4 is selected from CR x1 ; In Formulas 1-1 to 1-3, 1-5 to 1-7, Y a1 -Y a4 Each time it appears, the same or different selection is made from CR ya or N; in formula 1-4, Y a1 and Y a2 Each time it appears, the same or different selection is made from CR ya or N; In Formula 1-1, Formula 1-5, Formula 1-6 and Formula 1-7, Y b1 -Y b6 Each time it appears, the same or different selection is made from CR yb or N; in Formula 1-2 and Formula 1-4, Y b1 -Y b3 Each time it appears, the same or different selection is made from CR yb or N; in formula 1-3, Y b1 -Y b9 Each time it appears, the same or different selection is made from CR yb or N; In Formula 1-1 to Formula 1-7, Y d1 -Y d3 Each time it appears, the same or different selection is made from CR yd or N; The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof; R has the structure shown in formula 2-1: In Formula 2-1, 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; The R', R", R x , R ya , R yb , R yd , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The adjacent substituents R', R n , R ya , R yd Can optionally be linked to form a ring.
8. The organic electroluminescent device according to claim 1 or 7, wherein X3 is selected from CR x1 ; The R x1 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 7 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 8 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 7 carbon atoms, and combinations thereof; Preferably, R x1 Each occurrence is identically or differently selected from the group consisting of methyl, partially or fully deuterated methyl, ethyl, partially or fully deuterated ethyl, n-propyl, partially or fully deuterated n-propyl, isopropyl, partially or fully deuterated isopropyl, cyclopropyl, partially or fully deuterated cyclopropyl, n-butyl, partially or fully deuterated n-butyl, isobutyl, partially or fully deuterated isobutyl, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl, partially or fully deuterated cyclopentyl, cyclohexyl, partially or fully deuterated cyclohexyl, and combinations thereof.
9. The organic electroluminescent device according to claim 7, wherein R', R", R x , R ya , R yb , R yd , R f , R g , R n each occurrence is identically or differently 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; Preferably, R', R", R x , R ya , R yb , R yd , R f , R g , R n Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.
10. The organic electroluminescent device according to claim 1, wherein: R is selected, at each occurrence, identically or differently, from the group consisting of An-1 to An-55: Optionally, the above An1 to An 55 The hydrogen in the ion can be partially or completely replaced by deuterium.
11. The organic electroluminescent device as claimed in claim 1, wherein the first compound has Pt(L a )(L b ) represents the structure, L a and L b are the first ligand and the second ligand coordinated with the metal Pt, respectively. a Selected from the group consisting of: The L a The "#" in the structure indicates that the structure is consistent with L b The position of the connection; wherein the ligand L b Selected from the group consisting of: The L b In the structure, "t-Bu" represents tert-butyl, and "i-Pr" represents isopropyl; The L b In the structure Indicates that the structure and L a The position of the "#" connection in the Preferably, the first compound is selected from the group consisting of compounds Pt1 to Pt198, wherein the compounds Pt1 to Pt198 have Pt(L a )(L b ) represents a structure, wherein L a and the L b The corresponding structures are selected from the following table:
12. The organic electroluminescent device according to claim 1, wherein the triplet energy level of the first host material is higher than 2.69 eV and has a structure represented by any one of Formula 3 to Formula 4: In Formula 3, U1 to U3 are selected from CR4 or N at each occurrence, the same or different, and at least one of U1 to U3 is N; L3 is identically or differently selected at each occurrence from the group consisting of 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, and combinations thereof; In Formula 4, each occurrence of U4 is identically or differently selected from CR4 or N, and at least one U4 is N; Z is selected from O, S or NR5; R1 to R5 are selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R4 can be optionally linked to form a ring.
13. The organic electroluminescent device according to claim 12, wherein: In Formula 3, at least two of U1 to U3 are N; preferably, U1 to U3 are N.
14. The organic electroluminescent device according to claim 12, wherein: In Formula 3, L3 is identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and combinations thereof at each occurrence; Preferably, L3 is identically or differently selected at each occurrence from the group consisting of a single bond, phenylene, biphenylene, fluorenylene, triphenylene, furanylene, thienylene, dibenzofuranylene, dibenzothienylene, and combinations thereof.
15. The organic electroluminescent device according to claim 12, wherein R1 to R5 are selected from the group consisting of hydrogen, deuterium, halogen, cyano, 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, and combinations thereof at each occurrence; Preferably, R1 to R5 are selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, and combinations thereof, at each occurrence, the same or different. More preferably, R1 to R5 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiole, dibenzothiole, benzothiophene, dibenzothiophene, dibenzoselenophene, triazine, and Its combination.
16. The organic electroluminescent device according to claim 1 or 12, wherein the first host material is selected from the group consisting of the following structures: Optionally, hydrogen in the structures of compound N-1-1 to compound N-1-53, compound N-2-1 to compound N-2-32, and compound N-3-1 to compound N-3-11 can be partially or completely replaced by deuterium.
17. The organic electroluminescent device according to claim 1, wherein the triplet energy level of the second host material is higher than 2.69 eV and has a structure represented by Formula 5: In formula 5, L4 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; Ar1 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 20 carbon atoms, or a combination thereof; R6, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution; R6 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R6 can be optionally linked to form a ring.
18. The organic electroluminescent device according to claim 17, wherein the second host material has a structure represented by Formula 5-1 or Formula 5-2: L4, L5 are each independently 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; Ar1 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 20 carbon atoms, or a combination thereof; R6, when present each time, is identical or different and represents mono-substitution, poly-substitution or no substitution; R6 is selected, at each occurrence, identically or differently, 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 2 to 20 carbon atoms, alkenyl, 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 alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R6 can be optionally linked to form a ring.
19. The organic electroluminescent device according to claim 17 or 18, wherein R6 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, cyano, 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; Preferably, R6 is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, and its combination; More preferably, R6 is selected, at each occurrence, the same or different from the group consisting of hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiole, dibenzothiole, benzothiophene, dibenzothiophene, dibenzoselenophene, and combinations thereof.
20. The organic electroluminescent device according to claim 1 or 17, wherein the second host material is selected from the group consisting of the following structures: in, Optionally, hydrogen in Compound P-1 to Compound P-32 can be partially or completely replaced by deuterium.
21. The organic electroluminescent device according to claim 1, wherein the first compound is a phosphorescent light-emitting material, the first host material is an n-type host material, and the second host material is a p-type host material.
22. The organic electroluminescent device according to any one of claims 1 to 21, which emits blue light.
23. A compound composition comprising a first compound, a first host material and a second host material; wherein the triplet energy levels of the first host material and the second host material are both higher than 2.69 eV; The first compound has a structure represented by Formula 1: In Formula 1, Ring A and Ring D are selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, unsaturated heterocyclic rings having 3 to 30 carbon atoms, or combinations thereof, the same or different when they appear each time; Ring B is selected from unsaturated carbocyclic rings having 5 to 30 carbon atoms, or heteroaromatic rings having 3 to 30 carbon atoms; X1-X4 are selected from CR in the same or different ways each time they appear x , CR x1 or N, and at least one of X1-X4 is CR x1 ; The R x1 Each occurrence is identically or differently selected from the group consisting of 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, and combinations thereof; The R x 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The metal M is selected from metals with a relative atomic mass greater than 40; L1, L2 are each independently selected from a single bond, O, S, Se, (SiR'R') y , PR', NR', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof; y is 1, 2, 3, 4, or 5; K1-K4 are selected, at each occurrence, identically or differently, from a single bond, O or S; Z1-Z3 are selected from C or N at each occurrence, identically or differently; R in Formula 1 has a structure represented by Formula 2: In Formula 2, Ring F, Ring G, and Ring N are each independently selected from an aromatic ring having 6 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; Z4-Z7 are selected, at each occurrence, identically or differently, from C or N; R a , R b , R d , R f , R g , R n Each occurrence represents identically or differently monosubstituted, polysubstituted or unsubstituted; R', R a , R b , R d , R f , R g , R n 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 heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The adjacent substituents R', R a , R d , R n can optionally be linked to form a ring; "*" indicates the connection position of Formula 2.
24. An electronic device comprising the organic electroluminescent device as claimed in claims 1 to 22.
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