Organic electroluminescent device
By using a novel material combination of the first compound and the second compound of a specific structure in the organic layer of the organic electroluminescent device, the problems of reduced efficiency in the case of high brightness and blue phosphorescent devices are solved, and a higher efficiency, longer life and more saturated luminescence effect is achieved.
Patent Information
- Application Number
- CN202411258652.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-12-11
- Filing Date
- 2024-09-09
- Publication Date
- 2025-06-13
AI Technical Summary
The efficiency of existing organic light emitting diodes (OLEDs) rapidly decrease under high brightness conditions, and blue phosphorescent devices have problems such as blue unsaturation, short device life and high operating voltage, making it difficult to meet the needs of higher efficiency, longer life and more saturated luminescence spectrum.
A novel material combination of the first compound and the second compound having a specific structure is used as the light emitting layer main material of the organic electroluminescent device, and the efficiency and lifetime of the device are improved by including these compounds in the organic layer between the anode and the cathode.
It achieves higher efficiency, longer life, and provides better device performance, meeting the needs of higher efficiency, longer life and more saturated luminescence spectrum.
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Figure CN120152598A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to organic electronic devices, such as organic light-emitting devices. More particularly, it relates to an organic electroluminescent device having a first compound represented by Formula 1 and a second compound represented by Formula 2, an electronic device including the organic electroluminescent device, and a compound composition having a first compound represented by Formula 1 and a compound represented by Formula 2. Background Art
[0002] Organic electronic devices include but are not limited to the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-effect quantum dots (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between a cathode and an anode. Since OLEDs are a self-luminous solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.
[0004] OLEDs can be classified into three different types according to their emission mechanisms. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlet and triplet states, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.
[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.
[0007] The emission color of OLEDs can be achieved through the structural design of the emitting materials. OLEDs can include one or more emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.
[0008] CN112538060A discloses a compound for a cover layer, which has the following general formula Structure, and specifically discloses in its specific structure It focuses on placing triarylamine compounds containing benzoxazole structures above the cathode of an electroluminescent device and using them as a covering layer material with the optical characteristics of a high refractive index to improve the light extraction efficiency of the device. It does not disclose or teach the combination of benzoxazole triarylamine compounds and triazine compounds as the host material in the light-emitting layer of an electroluminescent device and the impact on device performance when applied.
[0009] WO2022216018A1 discloses an organic light-emitting device that includes a first compound and a second compound. The first compound has the following general formula The second compound has the following general formula Wherein A'1 has It focuses on the combination of dibenzofuranobenzoxazole triarylamine compounds and triazine compounds. It does not focus on triarylamine compounds with a benzoxazole skeletal structure and does not disclose or teach the impact on device performance of the combination of benzoxazole triarylamine structures and triazine compounds as the host material.
[0010] However, there is still room for improvement in the numerous host materials reported currently. To meet the increasing demands of the industry, especially for higher device efficiency and longer device life performance, new material combinations still require further research and development. Summary of the Invention
[0011] The present invention aims to provide a novel organic electroluminescent device to solve at least part of the above problems. The organic layer of the organic electroluminescent device contains a novel material combination composed of a first compound represented by the structure of Formula 1 and a second compound represented by the structure of Formula 2. This novel material combination is used as the host material in the light-emitting layer of the organic electroluminescent device, and this novel material combination can achieve higher efficiency and longer life in the organic electroluminescent device and can provide better device performance.
[0012] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:
[0013] An anode,
[0014] A cathode,
[0015] And an organic layer disposed between the anode and the cathode, wherein the organic layer at least includes a first compound and a second compound;
[0016] The first compound has the structure represented by Formula 1:
[0017]
[0018] Wherein,
[0019] X is selected from NR n , O or S;
[0020] Ar is selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms;
[0021] Z 1 to Z 4 is the same or different each time it appears and is selected from C, CR z or N, and one of Z 1 to Z 4 is selected from C and is linked to a six - membered ring containing W 1 to W 5 ;
[0022] W 1 to W 5 is the same or different each time it appears and is selected from C, CR w or N, and one of W 1 to W 5 is selected from C and is linked to L;
[0023] L is selected from a single bond, substituted or unsubstituted arylene having 6 - 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;
[0024] Ar 1 ,Ar 2 is selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or a combination thereof; and when Ar 1 ,Ar 2 contains a heteroatom in its ring atoms, the heteroatom is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom;
[0025] R w ,R nEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0026] R z Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R zWhen selected from a substituted aryl having 6 - 30 carbon atoms or a substituted heteroaryl having 3 - 30 carbon atoms, the aryl or heteroaryl is substituted by one or more groups selected from the group consisting of deuterium, halogen, an unsubstituted alkyl having 1 - 20 carbon atoms, an unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, an unsubstituted heteroalkyl having 1 - 20 carbon atoms, an unsubstituted heterocyclic group having 3 - 20 ring atoms, an unsubstituted aralkyl having 7 - 30 carbon atoms, an unsubstituted alkoxy having 1 - 20 carbon atoms, an unsubstituted aryloxy having 6 - 30 carbon atoms, an unsubstituted alkenyl having 2 - 20 carbon atoms, an unsubstituted alkynyl having 2 - 20 carbon atoms, an unsubstituted aryl having 6 - 30 carbon atoms, an unsubstituted heteroaryl having 3 - 30 carbon atoms, an unsubstituted alkylsilyl having 3 - 20 carbon atoms, an unsubstituted arylsilyl having 6 - 20 carbon atoms, an unsubstituted alkylgermyl having 3 - 20 carbon atoms, an unsubstituted arylgermyl having 6 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0027] Adjacent substituents R w may optionally be joined to form a ring;
[0028] The second compound has a structure represented by Formula 2:
[0029]
[0030] In Formula 2,
[0031] L 21 to L 23 each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 - 20 carbon atoms, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;
[0032] Ar 21 to Ar 23 each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof.
[0033] According to another embodiment of the present invention, an electronic device is also disclosed, which includes the organic electroluminescent device described in the foregoing embodiment.
[0034] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0035]
[0036] Wherein,
[0037] X is selected from NR n , O or S;
[0038] Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms;
[0039] Z 1 to Z 4 are the same or different each time they appear and are selected from C, CR z or N, and one of Z 1 to Z 4 is selected from C and is linked to a six - membered ring containing W 1 to W 5 ;
[0040] W 1 to W 5 are the same or different each time they appear and are selected from C, CR w or N, and one of W 1 to W 5 is selected from C and is linked to L;
[0041] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms, or a combination thereof;
[0042] Ar 1 , Ar 2 are selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, or a combination thereof; and when the ring atoms of Ar 1 , Ar 2 contain heteroatoms, the heteroatoms are selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom;
[0043] R w , R nEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0044] R z Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R zWhen selected from a substituted aryl having 6 - 30 carbon atoms or a substituted heteroaryl having 3 - 30 carbon atoms, the aryl or heteroaryl is substituted by one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 - 20 carbon atoms, unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, unsubstituted heteroalkyl having 1 - 20 carbon atoms, unsubstituted heterocyclic group having 3 - 20 ring atoms, unsubstituted aralkyl having 7 - 30 carbon atoms, unsubstituted alkoxy having 1 - 20 carbon atoms, unsubstituted aryloxy having 6 - 30 carbon atoms, unsubstituted alkenyl having 2 - 20 carbon atoms, unsubstituted alkynyl having 2 - 20 carbon atoms, unsubstituted aryl having 6 - 30 carbon atoms, unsubstituted heteroaryl having 3 - 30 carbon atoms, unsubstituted alkylsilyl having 3 - 20 carbon atoms, unsubstituted arylsilyl having 6 - 20 carbon atoms, unsubstituted alkylgermyl having 3 - 20 carbon atoms, unsubstituted arylgermyl having 6 - 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0045] Adjacent substituents R w may optionally be joined to form a ring;
[0046] The second compound has a structure represented by Formula 2:
[0047]
[0048] In Formula 2,
[0049] L 21 to L 23 each occurrence is the same or different and is selected from a single bond, substituted or unsubstituted alkylene having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 - 20 carbon atoms, substituted or unsubstituted arylene having 6 - 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or combinations thereof;
[0050] Ar 21 to Ar 23 each occurrence is the same or different and is selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or combinations thereof.
[0051] According to another embodiment of the present invention, there is also disclosed the use of a combination of a compound having a structure of Formula 1 and a compound having a structure of Formula 2 as a host material, and the specific structures of the compounds are as shown in the foregoing embodiments.
[0052] According to another embodiment of the present invention, an application of a combination of a compound having a structure of Formula 1 and a compound having a structure of Formula 2 as an organic light-emitting layer is also disclosed, and the specific structures of the compounds are as shown in the foregoing embodiments.
[0053] The present invention provides a novel organic electroluminescent device including a first compound represented by a structure of Formula 1 and a second compound represented by a structure of Formula 2 in an organic layer. The organic electroluminescent device can obtain higher efficiency, longer lifespan, and better device performance. BRIEF DESCRIPTION OF THE DRAWINGS
[0054] Figure 1 FIG. is a schematic diagram of an organic light-emitting device that may include the organic electroluminescent device disclosed herein.
[0055] Figure 2 FIG. is a schematic diagram of another organic light-emitting device that may include the organic electroluminescent device disclosed herein. DETAILED DESCRIPTION
[0056] OLEDs can be fabricated on various substrates such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures may also be omitted as needed. 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 fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of which is incorporated herein by reference.
[0057] 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 herein by reference in its entirety. Examples of a p-doped hole transport layer are doped with F at a molar ratio of 50:1 4m-MTDATA of -TCNQ is disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties, and include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of a blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entireties. Examples of an injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.
[0058] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not specifically described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.
[0059] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.
[0060] The OLED also requires a encapsulation layer, such as Figure 2 Schematically and non-limitingly shows an organic light-emitting device 200, which Figure 1 Differently, an encapsulation layer 102 can also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.
[0061] Devices fabricated in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) incorporating the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
[0062] The materials and structures described herein can also be used in other organic electronic devices listed above.
[0063] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In cases where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, there can be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as "disposed on" the anode.
[0064] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.
[0065] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.
[0066] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistical limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0067] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay from the triplet state, the fraction of the singlet excited state refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.
[0068] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).
[0069] Definition of substituent terms
[0070] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.
[0071] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.
[0072] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The 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. Additionally, the cycloalkyl can be optionally substituted.
[0073] Heteroalkyl - as used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.
[0074] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - methylvinyl, styryl, 2,2 - diphenylethylene, 1,2 - diphenylethylene, 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, cycloheptatriene, cyclooctenyl, cyclooctatetraene, and norbornenyl. Additionally, the alkenyl can be optionally substituted.
[0075] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.
[0076] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.
[0077] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.
[0078] Heteroaryl - As used herein, non - fused and fused heteroaromatic groups that can contain 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Heteroaryl also refers to heteroaromatic group. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and their nitrogen - containing analogs. Additionally, the heteroaryl can be optionally substituted.
[0079] Alkoxy - As used herein, represented by -O - alkyl, -O - cycloalkyl, -O - heteroalkyl or -O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.
[0080] Aryloxy - As used herein, represented by -O - aryl or -O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.
[0081] 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,
[0082] 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.
[0083] 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.
[0084] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.
[0085] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.
[0086] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0087] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocycloalkyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0088] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
[0089] In the compounds mentioned in the present 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. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.
[0090] Among the compounds mentioned in the present disclosure, polysubstituted refers to the range including disubstituted up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.
[0091] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, otherwise adjacent substituents in the compound cannot connect to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), as well as an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0092] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0093]
[0094] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0095]
[0096] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:
[0097]
[0098] In addition, the expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to the case where, when one of the adjacent two substituents represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0099]
[0100] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:
[0101] An anode,
[0102] A cathode,
[0103] And an organic layer disposed between the anode and the cathode, wherein the organic layer at least contains a first compound and a second compound;
[0104] The first compound has a structure represented by Formula 1:
[0105]
[0106] Wherein,
[0107] X is selected from NR n , O or S;
[0108] Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms;
[0109] Z 1 to Z 4 Each occurrence is the same or different and is selected from C, CR z or N, and one of Z 1 to Z 4 is selected from C and is connected to a six - membered ring containing W 1 to W 5 ;
[0110] W 1 to W 5 Each occurrence is the same or different and is selected from C, CR w or N, and one of W 1 to W 5 is selected from C and is connected to L;
[0111] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms, or a combination thereof;
[0112] Ar 1 , Ar 2 is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, or a combination thereof; and when Ar 1 , Ar 2When the ring atoms contain heteroatoms, the heteroatoms are selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom;
[0113] R w , R n is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0114] R z is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R zWhen selected from a substituted aryl having 6 - 30 carbon atoms or a substituted heteroaryl having 3 - 30 carbon atoms, the aryl or heteroaryl is substituted by one or more groups selected from the group consisting of deuterium, halogen, an unsubstituted alkyl having 1 - 20 carbon atoms, an unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, an unsubstituted heteroalkyl having 1 - 20 carbon atoms, an unsubstituted heterocyclic group having 3 - 20 ring atoms, an unsubstituted aralkyl having 7 - 30 carbon atoms, an unsubstituted alkoxy having 1 - 20 carbon atoms, an unsubstituted aryloxy having 6 - 30 carbon atoms, an unsubstituted alkenyl having 2 - 20 carbon atoms, an unsubstituted alkynyl having 2 - 20 carbon atoms, an unsubstituted aryl having 6 - 30 carbon atoms, an unsubstituted heteroaryl having 3 - 30 carbon atoms, an unsubstituted alkylsilyl having 3 - 20 carbon atoms, an unsubstituted arylsilyl having 6 - 20 carbon atoms, an unsubstituted alkylgermyl having 3 - 20 carbon atoms, an unsubstituted arylgermyl having 6 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0115] Adjacent substituents R w May optionally be linked to form a ring;
[0116] The second compound has the structure represented by Formula 2:
[0117]
[0118] In Formula 2,
[0119] L 21 To L 23 Each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 - 20 carbon atoms, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;
[0120] Ar 21 To Ar 23 Each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof.
[0121] As used herein, "adjacent substituents R w Can optionally be linked to form a ring" is intended to mean that any adjacent substituents R w Can be linked to form a ring. Obviously, any adjacent substituents R w Can also not be linked to form a ring.
[0122] As used herein, "Ar 1 , Ar 2 ring atoms" refers to the atoms in the ring of Ar 1 , Ar 2 . For example, the nitrogen atoms in azacycle groups such as pyridine, carbazole, quinazoline, etc. belong to the ring atoms. Therefore, Ar 1 , Ar 2 is not selected from any azacycle group. Also, for example, the nitrogen atom in an amino group does not belong to the ring atoms of Ar 1 , Ar 2 . Therefore, Ar 1 , Ar 2 can be selected from an aryl group having 6 - 30 carbon atoms substituted with an amino group, a heteroaryl group having 3 - 30 carbon atoms substituted with an amino group, a cycloalkyl group having 3 - 20 ring carbon atoms substituted with an amino group, or a combination thereof.
[0123] According to one embodiment of the present invention, wherein R w , R n is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 - 20 carbon atoms, a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 - 20 carbon atoms, a substituted or unsubstituted amino group having 0 - 20 carbon atoms, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0124] R zEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R z is selected from substituted groups, the group is substituted by one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0125] According to one embodiment of the present invention, wherein the first compound has a structure represented by Formula 1-1:
[0126]
[0127] Wherein,
[0128] X is selected from NR n , O or S;
[0129] T 1 to T 5CR is selected the same or differently each time it appears t or N;
[0130] Z 1 to Z 4 C, CR are selected the same or differently each time they appear z or N, and Z 1 to Z 4 One of them is selected from C and is linked to a six-membered ring containing W 1 to W 5 ;
[0131] W 1 to W 5 C, CR are selected the same or differently each time they appear w or N, and W 1 to W 5 One of them is selected from C and is linked to L;
[0132] L is selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;
[0133] Ar 1 , Ar 2 is selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, or a combination thereof; and when Ar 1 , Ar 2 contains a heteroatom in its ring atoms, the heteroatom is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom;
[0134] R t , R w , R nEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0135] R z Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R zWhen selected from a substituted aryl having 6 to 30 carbon atoms or a substituted heteroaryl having 3 to 30 carbon atoms, the aryl or heteroaryl is substituted by one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclic group having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 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 alkylgermyl having 3 to 20 carbon atoms, unsubstituted arylgermyl having 6 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0136] Adjacent substituents R t may optionally be linked to form a ring;
[0137] Adjacent substituents R w may optionally be linked to form a ring.
[0138] As used herein, "adjacent substituents R t can optionally be linked to form a ring" is intended to mean that any adjacent substituents R t can be linked to form a ring. Obviously, any adjacent substituents R t may not be linked to form a ring either.
[0139] According to one embodiment of the present invention, wherein Z 1 to Z 4 are each independently selected from C, CR z or N each time they appear, and one of Z 1 , Z 2 , Z 4 is selected from C and is linked to a six-membered ring containing W 1 to W 5 .
[0140] According to one embodiment of the present invention, wherein Z 1 to Z 4 are each independently selected from C, CR z or N each time they appear, and one of Z 1 , Z 2 is selected from C and is linked to a six-membered ring containing W1 to W 5 are connected to a six-membered ring.
[0141] According to one embodiment of the present invention, wherein Ar 1 , Ar 2 at least one of which is selected from substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms; and when Ar 1 , Ar 2 contains a heteroatom in the ring atoms thereof, the heteroatom is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom.
[0142] According to one embodiment of the present invention, wherein X is selected from O or S.
[0143] According to one embodiment of the present invention, wherein X is selected from O.
[0144] According to one embodiment of the present invention, wherein L is selected from a single bond, substituted or unsubstituted arylene having 6 to 24 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 24 carbon atoms, or a combination thereof.
[0145] According to one embodiment of the present invention, wherein L is selected from a single bond or substituted or unsubstituted arylene having 6 to 20 carbon atoms.
[0146] According to one embodiment of the present invention, wherein L is selected from a single bond, phenylene, naphthylene, biphenylene, phenanthrylene.
[0147] According to one embodiment of the present invention, wherein W 1 to W 5 are each independently selected from C or CR w , and one of W 1 to W 5 is selected from C and is connected to L.
[0148] According to one embodiment of the present invention, wherein W 1 to W 5 are each independently selected from C or R w , and one of W 2 , W 3 , W 4 is C and is connected to L.
[0149] According to one embodiment of the present invention, wherein W 1 to W 5 are each independently selected from C or R w , and W 4 is C and is connected to L.
[0150] According to one embodiment of the present invention, wherein W1 to W 5 each occurrence is the same as or different from and is selected from C or R w and W 3 is C and is connected to L
[0151] According to one embodiment of the present invention, wherein Z 1 to Z 3 each occurrence is the same as or different from and is selected from CR z .
[0152] According to one embodiment of the present invention, wherein R w R z R n each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, and combinations thereof
[0153] According to one embodiment of the present invention, wherein R w R z R n each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, yl, methyl, ethyl, tert - butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof
[0154] According to one embodiment of the present invention, wherein Ar 1 Ar 2 is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted cycloalkyl having 4 - 10 ring carbon atoms, or combinations thereof;
[0155] Ar is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, or substituted or unsubstituted heteroaryl having 3 - 18 carbon atoms
[0156] According to one embodiment of the present invention, wherein Ar 1 Ar 2each occurrence is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silofluorene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted spirosilofluorene, substituted or unsubstituted group, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or a combination thereof;
[0157] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silofluorene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted spirosilofluorene, substituted or unsubstituted group, or a combination thereof.
[0158] According to one embodiment of the present invention, wherein Ar, Ar 1 , Ar 2 each occurrence is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silofluorene, substituted or unsubstituted group, or a combination thereof.
[0159] According to one embodiment of the present invention, wherein Ar, Ar 1 , Ar 2 each occurrence is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted silofluorene, substituted or unsubstituted group, or a combination thereof.
[0160] According to one embodiment of the present invention, wherein Ar, Ar 1 , Ar 2each occurrence being the same as or different from each other and being selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, fluorenyl, silylfluorenyl, group, or a combination thereof.
[0161] According to one embodiment of the present invention, wherein R t each occurrence being the same as or different from each other and being selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, and combinations thereof.
[0162] According to one embodiment of the present invention, wherein R t each occurrence being the same as or different from each other and being selected from the group consisting of: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, group, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.
[0163] According to one embodiment of the present invention, wherein the first compound is selected from the group consisting of compound A-1 to compound A-603.
[0164] According to one embodiment of the present invention, wherein the hydrogen in the structures of compound A-1 to compound A-603 can be partially or completely replaced by deuterium.
[0165] According to one embodiment of the present invention, wherein the first compound is selected from the group consisting of compound A-1 to compound A-617; the specific structures of compound A-1 to compound A-617 are as follows:
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211] According to one embodiment of the present invention, the hydrogen in the structures of Compounds A-1 to A-617 can be partially or completely replaced by deuterium.
[0212] According to one embodiment of the present invention, the second compound has the structure shown in Formula 2-1:
[0213]
[0214] V 1 -V 6 Each occurrence is independently selected from C, N, or CR v , and one of V 1 -V 6 is C and is connected to L 23 ;
[0215] L 21 to L 23 Each occurrence is independently selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;
[0216] Ar 21 and Ar 22Same or different each time it appears, selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof;
[0217] R v Same or different each time it appears, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0218] Adjacent substituents R v Can optionally be linked to form a ring.
[0219] As used herein, adjacent substituents R v Can optionally be linked to form a ring, which is intended to mean that any adjacent substituents R v Can be linked to form a ring. Obviously, any adjacent substituents R v Can also not be linked to form a ring.
[0220] According to an embodiment of the present invention, wherein at least one of V 1 to V 6 is selected from CR v , and said R v Same or different each time it appears, selected from substituted or unsubstituted aryl having 6 - 30 carbon atoms.
[0221] According to an embodiment of the present invention, wherein the second compound has the structure shown in Formula 2 - 1 - 1 or Formula 2 - 1 - 2:
[0222]
[0223] Wherein in Formula 2 - 1 - 1, V 1 -V5 each occurrence is independently selected from C, N, or CR v , V 11 -V 15 each occurrence is independently selected from N or CR v1 , and one of the V 1 -V 5 is C and is linked to L 23 ; in Formula 2-1-2, V 1 -V 4 each occurrence is independently selected from C, N, or CR v , V 11 -V 14 each occurrence is independently selected from N or CR v1 , and one of the V 1 -V 4 is C and is linked to L 23 ;
[0224] V is selected from O, S, or Se;
[0225] L 21 to L 23 each occurrence is independently selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof;
[0226] Ar 21 and Ar 22 each occurrence is independently selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof;
[0227] R v , R v1Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0228] Adjacent substituents R v , R v1 can optionally be linked to form a ring.
[0229] As used herein, adjacent substituents R v , R v1 can optionally be linked to form a ring, which is intended to mean any adjacent group of substituents, for example, between adjacent substituents R v , between adjacent substituents R v1 , and between adjacent substituents R v and R v1 , any one or more of these groups of substituents can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring.
[0230] According to one embodiment of the present invention, in Formula 2-1-2, V is selected from O or S.
[0231] According to one embodiment of the present invention, in Formula 2-1-2, V is selected from O.
[0232] According to one embodiment of the present invention, in Formula 2-1-1, V 1 to V 5 are each occurrence the same as or different from and are selected from C or CR v , V 11 to V 15 are each occurrence the same as or different from and are selected from CR v1 ; in Formula 2-1-2, V 1 to V4 Each occurrence is the same as or different from and is selected from C or CR v , V 11 to V 14 Each occurrence is the same as or different from and is selected from CR v1。
[0233] According to one embodiment of the present invention, wherein the R v , R v1 Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0234] According to one embodiment of the present invention, wherein in Formula 2-1-1, at least one of V 1 to V 5 is selected from CR v , or at least one of V 11 to V 15 is selected from CR v1 ; in Formula 2-1-2, at least one of V 1 to V 4 is selected from CR v , or at least one of V 11 to V 14 is selected from CR v1 ; and the R v , R v1 Each occurrence is the same as or different from and is selected from substituted or unsubstituted aryl having 6-30 carbon atoms.
[0235] According to one embodiment of the present invention, wherein the R v , R v1 Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.
[0236] According to one embodiment of the present invention, wherein at least one of the Ar 21 and Ar 22 has a structure with two fused rings or three fused rings.
[0237] According to one embodiment of the present invention, wherein the Ar 21 and Ar 22 Each occurrence is the same as or different from and is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, or combinations thereof.
[0238] According to one embodiment of the present invention, wherein said Ar 21 and Ar 22 are each independently selected, each time they appear, from substituted or unsubstituted aryl having 6 - 16 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms, or a combination thereof.
[0239] According to one embodiment of the present invention, wherein said Ar 21 and Ar 22 are each independently selected, each time they appear, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted yl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted indolocarbazolyl, or a combination thereof.
[0240] According to one embodiment of the present invention, wherein said L 21 to L 23 are each independently selected, each time they appear, from a single bond, substituted or unsubstituted arylene having 6 - 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 20 carbon atoms, or a combination thereof.
[0241] According to one embodiment of the present invention, wherein said L 21 to L 23 are each independently selected, each time they appear, from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or a combination thereof.
[0242] According to one embodiment of the present invention, wherein said second compound is selected from the group consisting of compound B - 1 to compound B - 255.
[0243] According to one embodiment of the present invention, wherein the hydrogen in the structures of compound B - 1 to compound B - 255 can be partially or completely replaced by deuterium.
[0244] According to one embodiment of the present invention, wherein said second compound is selected from the group consisting of compound B - 1 to compound B - 260; the specific structures of compound B - 1 to compound B - 260 are as follows:
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266] According to an embodiment of the present invention, in the structures of Compounds B-1 to B-260, the hydrogen can be partially or completely replaced by deuterium.
[0267] According to an embodiment of the present invention, in the preparation of a device, when using the first compound and the second compound selected by the present invention and co-evaporating with a luminescent material to form a light-emitting layer, the light-emitting layer can be formed by co-evaporating the first compound, the second compound, and the luminescent material in different evaporation sources respectively, or by placing a mixture of the first compound and the second compound pre-mixed in the same evaporation source and then co-evaporating with the luminescent material placed in another evaporation source. This pre-mixing method can further save evaporation sources.
[0268] According to an embodiment of the present invention, wherein the organic layer is a light-emitting layer, and the first compound and the second compound are host materials.
[0269] According to an embodiment of the present invention, wherein the light-emitting layer further comprises at least one phosphorescent material.
[0270] According to an embodiment of the present invention, wherein the phosphorescent material is a metal complex having the general formula M(L a ) m (L b ) n (L c ) q ;
[0271] M is selected from metals having a relative atomic mass greater than 40;
[0272] L a , L b and L c are the first ligand, the second ligand, and the third ligand coordinated to the M, respectively; L a , L b and L c can optionally be connected to form a multidentate ligand;
[0273] L a , L b and L c are the same or different; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q is equal to the oxidation state of the M; when m is greater than or equal to 2, the plurality of L a are the same or different; when n is 2, the two L b are the same or different; when q is 2, the two L c are the same or different;
[0274] L a is the same or different each time it appears and is selected from the structure shown in Formula 3:
[0275]
[0276] wherein,
[0277] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0278] Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
[0279] Ring D and Ring E are fused via U a and U b ;
[0280] Ua and U b is the same as or different from each other each time it appears, and is selected from C or N;
[0281] R d and R e each time it appears, it represents single-substituted, multi-substituted or unsubstituted;
[0282] V 31 to V 34 each time it appears, it is the same as or different from each other, and is selected from CR v3 or N;
[0283] R d , R e and R v3 each time it appears, it is the same as or different from each other, and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
[0284] Adjacent substituents R d , R e and R v3 can optionally be connected to form a ring;
[0285] L b and L c each time it appears, it is the same as or different from each other, and is selected from any one of the following structures:
[0286]
[0287]
[0288] wherein,
[0289] R a , Rb and R c represents, each time it appears, the same or differently, mono-substitution, multi-substitution, or no substitution;
[0290] X b is, each time it appears, the same or differently, selected from the group consisting of O, S, Se, NR N1 and CR C1 R C2 ;
[0291] X c and X d is, each time it appears, the same or differently, selected from the group consisting of O, S, Se and NR N2 ;
[0292] R a , R b , R c , R N1 , R N2 , R C1 and R C2 is, each time it appears, the same or differently, selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0293] the ligand L b , L c in the structure of, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2can optionally be linked to form a ring.
[0294] In this text, adjacent substituents R d , R e , R v3 can optionally be linked to form a ring, which is intended to mean that when there are substituents R d , substituent R e , substituent R v3 , among which adjacent substituent groups, such as between adjacent substituents R d , between adjacent substituents R e , between adjacent substituents R v3 , between adjacent substituents R d and R e , between adjacent substituents R d and R v3 , and between adjacent substituents R e and R v3 , any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when there are substituents R d , substituent R e , substituent R v3 , these substituent groups may also not be linked to form a ring.
[0295] In this text, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring, which is intended to mean that among the adjacent substituent groups, for example, between two substituents R a , between two substituents R b , between two substituents R c , between substituent R a and R b , between substituent R a and R c , between substituent R b and R c , between substituent R a and R N1 , between substituent R b and R N1 , between substituent R a and R C1 , between substituent R a and R C2 , between substituent R b and R C1 , between substituent R b and RC2 between, substituent R a and R N2 between, substituent R b and R N2 between, and R C1 and R C2 between, any one or more of these substituent groups may be connected to form a ring. For example, adjacent substituents R a , R b can optionally be connected to form a ring, which can form one or more of the following structures including but not limited to:
[0296] wherein, W is selected from O, S, Se, NR w1 or CR w1 R w1 ; wherein said R w1 , R a ’, R b ’ are defined the same as said R a . Obviously, these substituents may also not be connected to form a ring with each other.
[0297] According to an embodiment of the present invention, wherein, in Formula 3, two adjacent substituents R e are connected to form a ring.
[0298] According to an embodiment of the present invention, wherein, in Formula 3, two adjacent substituents R e are connected to form a 5-membered unsaturated carbon ring, a 5-membered heteroaromatic ring or a benzene ring.
[0299] According to an embodiment of the present invention, wherein, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring.
[0300] According to an embodiment of the present invention, wherein, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.
[0301] According to an embodiment of the present invention, wherein, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring, and two adjacent substituents R e are connected to form a benzene ring or a 6-membered heteroaromatic ring.
[0302] According to an embodiment of the present invention, wherein, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring, and two adjacent substituents R e are connected to form a benzene ring or a 6-membered heteroaromatic ring.
[0303] According to an embodiment of the present invention, in Formula 3, R d , R e , R v3 in at least one or two groups of adjacent substituents are connected to form a ring. For example, two substituents R d are connected to form a ring, or two substituents R e are connected to form a ring, or two substituents R v3 are connected to form a ring, or the substituent R d and the substituent R e are connected to form a ring, or the substituent R d and the substituent R v3 are connected to form a ring, or the substituent R e and the substituent R v3 are connected to form a ring, or two substituents R d are connected to form a ring while two substituents R e are connected to form a ring, or two substituents R d are connected to form a ring while two substituents R v3 are connected to form a ring, or two substituents R e are connected to form a ring while two substituents R v3 are connected to form a ring, the substituent R e and the substituent R v3 are connected to form a ring while 2 substituents R v3 are connected to form a ring, or the substituent R d and the substituent R v3 are connected to form a ring while 2 substituents R v3 are connected to form a ring; R d , R e , R v3 in more groups of adjacent substituents are connected to form a ring, and the situation is similar.
[0304] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is a metal complex, and the metal complex has the general formula of M(L a ) m (L b ) n ;
[0305] M is selected from metals with a relative atomic mass greater than 40;
[0306] L a , L b are the first ligand and the second ligand coordinated with the M respectively; L a , L b can optionally be connected to form a polydentate ligand;
[0307] m is 1, 2 or 3; n is 0, 1 or 2; the sum of m and n is equal to the oxidation state of said M; when m is greater than or equal to 2, a plurality of Ls a can be the same or different; when n is 2, two Ls b can be the same or different;
[0308] L a each occurrence is the same or different and is selected from the structures shown in Formula 3:
[0309]
[0310] wherein,
[0311] ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0312] ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
[0313] ring D and ring E are fused via U a and U b ;
[0314] U a and U b each occurrence is the same or different and is selected from C or N;
[0315] R d and R e each occurrence is the same or different and represents mono-substitution, multi-substitution or no substitution;
[0316] V 31 to V 34 each occurrence is the same or different and is selected from CR v3 or N;
[0317] R d , R e and R v3Each occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0318] Adjacent substituents R d , R e and R v3 can optionally be linked to form a ring;
[0319] wherein the ligand L b each occurrence is the same as or different from each other and is selected from the following structures:
[0320]
[0321] wherein, R 1 to R 7Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
[0322] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is selected from the following structures:
[0323]
[0324] wherein, R 1 to R 3 at least one of which is selected from 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, or a combination thereof; and / or R 4 to R 6 at least one of which is selected from 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, or a combination thereof.
[0325] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is selected from the following structures:
[0326]
[0327] wherein, R 1 to R 3at least two of which are the same or different each time they appear and are independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or R 4 to R 6 at least two of which are the same or different each time they appear and are independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.
[0328] According to one embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b is the same or different each time it appears and is independently selected from the following structures:
[0329]
[0330] wherein, R 1 to R 3 at least two of which are the same or different each time they appear and are independently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or R 4 to R 6 at least two of which are the same or different each time they appear and are independently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.
[0331] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex, a Pt complex or an Os complex.
[0332] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and has the formula Ir(L a )(L b )(L c ), Ir(L a )(L 2 )(L b ), Ir(L a )(L b ), Ir(L 2 )(L a ), Ir(L 2 )(L c ), or Ir(L a )(L c ) 2The structure shown in any of them.
[0333] According to an embodiment of the present invention, wherein L a Has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of a 6-membered fused 6-membered aromatic ring, a 6-membered fused 6-membered heteroaromatic ring, a 6-membered fused 5-membered aromatic ring, and a 6-membered fused 5-membered heteroaromatic ring.
[0334] According to an embodiment of the present invention, in the organic electroluminescent device, wherein L a Has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline, and aza-phenanthrene.
[0335] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent emitting material is an Ir complex and contains a ligand L a , the L a Each occurrence is the same or different and is optionally selected from any one of the group consisting of the following structures:
[0336]
[0337]
[0338]
[0339] In the structure, TMS represents trimethylsilyl.
[0340] According to an embodiment of the present invention, wherein, in the organic electroluminescent device, the phosphorescent emitting material is an Ir complex and contains a ligand L b , the L b Each occurrence is the same or different and is optionally selected from any one of the group consisting of the following structures:
[0341]
[0342] According to an embodiment of the present invention, wherein, in the organic electroluminescent device, the phosphorescent emitting material is selected from the group consisting of the following structures:
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351] In the said structure, TMS represents trimethylsilyl.
[0352] According to another embodiment of the present invention, an electronic device is also disclosed, which comprises the organic electroluminescent device described in the foregoing embodiment.
[0353] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises a first compound and a second compound, wherein the first compound has a structure represented by Formula 1:
[0354]
[0355] Wherein,
[0356] X is selected from NR n , O or S;
[0357] Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms;
[0358] Z 1 to Z 4 Each occurrence is the same or different and is selected from C, CR z or N, and one of Z 1 to Z 4 is selected from C and is connected to a six - membered ring containing W 1 to W 5 ;
[0359] W 1 to W 5 Each occurrence is the same or different and is selected from C, CR w or N, and one of W 1 to W 5 is selected from C and is connected to L;
[0360] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms, or a combination thereof;
[0361] Ar 1 ,Ar 2 is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, or a combination thereof; and when Ar 1, Ar 2 When the ring atoms of 2 contain heteroatoms, the heteroatoms are selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom;
[0362] R w , R n Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 - 20 carbon atoms, a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 - 20 carbon atoms, a substituted or unsubstituted amino group having 0 - 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0363] R z Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 - 20 carbon atoms, a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 - 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and when Rz When selected from a substituted aryl having 6 to 30 carbon atoms or a substituted heteroaryl having 3 to 30 carbon atoms, the aryl or heteroaryl is substituted by one or more groups selected from the group consisting of deuterium, halogen, an unsubstituted alkyl having 1 to 20 carbon atoms, an unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl having 7 to 30 carbon atoms, an unsubstituted alkoxy having 1 to 20 carbon atoms, an unsubstituted aryloxy having 6 to 30 carbon atoms, an unsubstituted alkenyl having 2 to 20 carbon atoms, an unsubstituted alkynyl having 2 to 20 carbon atoms, an unsubstituted aryl having 6 to 30 carbon atoms, an unsubstituted heteroaryl having 3 to 30 carbon atoms, an unsubstituted alkylsilyl having 3 to 20 carbon atoms, an unsubstituted arylsilyl having 6 to 20 carbon atoms, an unsubstituted alkylgermyl having 3 to 20 carbon atoms, an unsubstituted arylgermyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
[0364] Adjacent substituents R w may optionally be joined to form a ring;
[0365] The second compound has a structure represented by Formula 2:
[0366]
[0367] In Formula 2,
[0368] L 21 to L 23 each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
[0369] Ar 21 to Ar 23 each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
[0370] According to another embodiment of the present invention, there is also disclosed an application of a combination of a compound having a structure of Formula 1 and a compound having a structure of Formula 2 as a host material, and the specific structures of the compounds are as shown in the foregoing embodiments.
[0371] According to another embodiment of the present invention, an application of a combination of a compound having a structure of Formula 1 and a compound having a structure of Formula 2 as an organic light-emitting layer is also disclosed, and the specific structures of the compounds are as shown in the foregoing embodiments.
[0372] Combined with other materials
[0373] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132-0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0374] The materials described herein as being useful for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the devices. For example, the compounds disclosed herein can be combined with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080-0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0375] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art (including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc.) by methods well known to those skilled in the art.
[0376] Material synthesis example:
[0377] The present invention places no restrictions on the preparation method of the second compound selected. Those skilled in the art can use conventional synthesis methods for preparation, or can refer to the preparation methods in patent applications such as CN111095586A and CN202310523364.7, and the preparation methods will not be elaborated herein.
[0378] The present invention places no restrictions on the preparation method of the selected first compound, and those skilled in the art can prepare it using conventional synthesis methods or can easily obtain it by referring to the following synthesis routes and preparation methods of the compounds.
[0379] Synthesis Example 1: Synthesis of Compound A-14
[0380] Step 1: Synthesis of Intermediate 3
[0381]
[0382] Under nitrogen protection, Intermediate 1 (5.0 g, 18.24 mmol), Intermediate 2 (3.42 g, 21.87 mmol), tetrakis(triphenylphosphine)palladium (420 mg, 0.36 mmol), potassium carbonate (5.04 g, 36.47 mmol), toluene (100 mL), ethanol (20 mL), and water (20 mL) were added to a three-necked flask and reacted at 100 °C for 16 h. After the reaction was completed, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the solvent was removed by concentration, and the crude product was purified by column chromatography using PE / DCM = 1 / 1 to obtain white solid Intermediate 3 (5 g, yield: 90%).
[0383] Step 2: Synthesis of Compound A-14
[0384]
[0385] Under nitrogen protection, Intermediate 3 (3.00 g, 9.81 mmol), Intermediate 4 (2.90 g, 9.81 mmol), bis(dibenzylideneacetone)palladium (111.25 mg, 0.193 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (111.25 mg, 0.27 mmol), sodium tert-butoxide (1.89 g, 19.67 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was completed, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed by concentration, and the crude product was purified by column chromatography using PE / DCM = 2 / 1 to obtain yellow solid Compound A-14 (4 g, yield: 72%). The product was confirmed to be the target product with a molecular weight of 564.2.
[0386] Synthesis Example 2: Synthesis of Compound A-525
[0387] Step 1: Synthesis of Intermediate 7
[0388]
[0389] Under nitrogen protection, intermediate 5 (5 g, 26.59 mmol), intermediate 6 (3.1 g, 29.21 mmol), and methanol (100 mL) were added to a three-necked flask, and the reaction was carried out at room temperature for 2 h. After the reaction was completed, the solid was filtered, washed three times with methanol, dissolved in dichloromethane (100 mL), and 2,3-dichloro-5,6-dicyanobenzoquinone (5.13 g, 22.60 mmol) was added, and the reaction was carried out at room temperature for 2 h. After the reaction was completed, the reaction solution was extracted with dichloromethane, the organic phase was washed with water, and the crude product obtained after removing the solvent was purified by column chromatography with PE / DCM = 1 / 1 to obtain white solid intermediate 7 (4 g, yield: 55%).
[0390] Step 2: Synthesis of intermediate 8
[0391]
[0392] Under nitrogen protection, intermediate 8 (4.0 g, 14.59 mmol), intermediate 2 (2.51 g, 16.05 mmol), tetrakis(triphenylphosphine)palladium (168.63 mg, 0.15 mmol), potassium carbonate (4.03 g, 29.16 mmol), toluene (100 mL), ethanol (20 mL), and water (20 mL) were added to a three-necked flask, and the reaction was carried out at 100 °C for 16 h. After the reaction was completed, it was extracted with ethyl acetate, the organic phase was washed with water, the solvent was concentrated and removed, and the crude product was purified by column chromatography with PE / DCM = 1 / 1 to obtain white solid intermediate 9 (3 g, yield: 67%).
[0393] Step 3: Synthesis of compound A-525
[0394]
[0395] Under nitrogen protection, intermediate 9 (3.00 g, 9.81 mmol), intermediate 4 (2.13 g, 7.21 mmol), bis(dibenzylideneacetone)palladium (37.08 mg, 0.07 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (53.71 mg, 0.13 mmol), sodium tert-butoxide (1.26 g, 13.11 mmol), and xylene (100 mL) were added to a three-necked flask, and the reaction was carried out at 140 °C for 2 h. After the reaction was completed, it was filtered, and the crude product after removing the solvent from the filtrate was purified by column chromatography with PE / DCM = 2 / 1 to obtain light yellow solid compound A-525 (3 g, yield: 74%). The product was confirmed to be the target product, and the molecular weight was 564.2.
[0396] Synthesis Example 3: Synthesis of compound A-387
[0397] Step 1: Synthesis of intermediate 11
[0398]
[0399] Under nitrogen protection, intermediate 10 (50.00 g, 265.92 mmol), benzaldehyde (31.04 g, 292.52 mmol), and ethanol (500 mL) were added to a three-necked flask, and the reaction was carried out at 80 °C for 16 h. After the reaction was completed, the solvent was concentrated and removed. The solid was washed three times with petroleum ether and then dissolved in dichloromethane (500 mL). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 90.55 g, 398.89 mmol) was added and the reaction was carried out at room temperature for 12 h. After the reaction was completed, the reaction solution was extracted with dichloromethane, and the organic phase was washed with water. After removing the solvent, the obtained crude product was purified by column chromatography with PE / DCM = 1 / 1 to obtain white solid intermediate 11 (50 g, yield: 69%).
[0400] Step 2: Synthesis of intermediate 12
[0401]
[0402] Under nitrogen protection, intermediate 11 (40.00 g, 145.92 mmol), intermediate 2 (25.10 g, 160.52 mmol), tetrakis(triphenylphosphine)palladium (1.69 g, 1.46 mmol), potassium carbonate (40.33 g, 291.85 mmol), toluene (200 mL), ethanol (50 mL), and water (50 mL) were added to a three-necked flask, and the reaction was carried out at 100 °C for 16 h. After the reaction was completed, it was extracted with ethyl acetate, and the organic phase was washed with water. The solvent was concentrated and removed, and the crude product was purified by column chromatography with PE / DCM = 1 / 1 to obtain white solid intermediate 12 (35 g, yield: 78%).
[0403] Step 3: Synthesis of compound A-387
[0404]
[0405] Under nitrogen protection, intermediate 12 (4.00 g, 13.08 mmol), intermediate 4 (4.25 g, 14.39 mmol), bis(dibenzylideneacetone)palladium (148.34 mg, 0.26 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (214.83 mg, 0.52 mmol), sodium tert-butoxide (2.51 g, 26.16 mmol), and xylene (100 mL) were added to a three-necked flask, and the reaction was carried out at 140 °C for 2 h. After the reaction was completed, it was filtered, and the crude product after removing the solvent from the filtrate was purified by column chromatography with PE / DCM = 1 / 1 to obtain pale yellow solid compound A-387 (5 g, yield: 68%). The product was confirmed to be the target product, and the molecular weight was 564.2.
[0406] Synthesis Example 4: Synthesis of Compound A-431
[0407]
[0408] Under nitrogen protection, intermediate 12 (3.00 g, 9.81 mmol), intermediate 13 (3.78 g, 9.81 mmol), bis(dibenzylideneacetone)palladium (II) (111.25 mg, 0.20 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (161.12 mg, 0.39 mmol), sodium tert-butoxide (1.89 g, 19.67 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was completed, the mixture was filtered. The crude product obtained after removing the solvent from the filtrate was purified by column chromatography using PE / DCM = 1 / 1 to obtain a pale yellow solid compound A-431 (5 g, yield: 78%). The product was confirmed to be the target product with a molecular weight of 654.2.
[0409] Synthesis Example 5: Synthesis of Compound A-164
[0410]
[0411] Under nitrogen protection, intermediate 14 (3.00 g, 8.43 mmol), intermediate 4 (2.74 g, 9.27 mmol), bis(dibenzylideneacetone)palladium (II) (47.80 mg, 0.08 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (69.23 mg, 0.17 mmol), sodium tert-butoxide (1.62 g, 16.86 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was completed, the mixture was filtered. The crude product obtained after removing the solvent from the filtrate was purified by column chromatography using PE / DCM = 1 / 1 to obtain a pale yellow solid compound A-164 (3.5 g, yield: 68%). The product was confirmed to be the target product with a molecular weight of 614.2.
[0412] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain the structures of other first compounds selected by the present invention by improving it.
[0413] The preparation method of the organic electroluminescent device is not limited. The preparation methods in the following examples are only examples and should not be construed as limitations. Those skilled in the art can reasonably improve the preparation methods in the following examples based on the prior art. Exemplarily, the ratios of various materials in the light-emitting layer are not particularly limited, and those skilled in the art can reasonably select within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer materials, the host material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the host material can account for 90%-98%, and the light-emitting material can account for 2%-10%. In addition, the host material can be the first compound selected in this application and the second compound selected in this application, and the ratio of the first compound selected in this application and the second compound selected in this application in the host material can be 99:1 to 1:99; or the ratio can be 80:20 to 20:80; or the ratio can be 60:40 to 40:60. The characteristics of the light-emitting devices prepared in the examples are tested by using conventional equipment in the art and methods well-known to those skilled in the art. In the examples of the devices, the characteristics of the devices are also tested by using conventional equipment in the art (including but not limited to evaporation machines produced by Angstrom Engineering, optical test systems and life test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc.) and methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above equipment and test methods, and can obtain the inherent data of the samples determinately and without being affected, the above relevant content will not be elaborated in this patent.
[0414] Device Example 1
[0415] First, a glass substrate with a 120-nm-thick indium tin oxide (ITO) anode is cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then the substrate is mounted on a substrate holder and loaded into a vacuum chamber. The following specified organic layers are sequentially evaporated onto the ITO anode by thermal vacuum at a rate of -8 under a vacuum of about 10 Torr. Compounds HT and HI are co-evaporated and used as the hole injection layer (HIL, weight ratio 97:3), with a thickness of Compound HT is used as the hole transport layer (HTL), with a thickness of Compound EB is used as the electron blocking layer (EBL), with a thickness of Then, the compound A-14 of the present invention as the first host, the compound B-227 as the second host, and the compound RD as the dopant are co-evaporated and used as the light-emitting layer (EML, weight ratio 68.6:29.4:2), with a thickness of The compound HB is used as a hole blocking layer (HBL) with a thickness of On the hole blocking layer, the compounds ET and lithium 8-hydroxyquinolate (Liq) are co-evaporated as an electron transport layer (ETL, weight ratio 40:60) with a thickness of Finally, Lithium 8-hydroxyquinolate (Liq) with a thickness of is evaporated as an electron injection layer (EIL), and
[0416] Device Example 2
[0417] The implementation of Device Example 2 is the same as that of Device Example 1, except that compound A-525 is used instead of the compound A-14 of the present invention as the first host in the emission layer (EML).
[0418] Device Example 3
[0419] The implementation of Device Example 3 is the same as that of Device Example 1, except that compound A-387 is used instead of the compound A-14 of the present invention as the first host in the emission layer (EML).
[0420] Device Example 4
[0421] The implementation of Device Example 4 is the same as that of Device Example 1, except that compound A-431 is used instead of the compound A-14 of the present invention as the first host in the emission layer (EML).
[0422] Device Example 5
[0423] The implementation of Device Example 5 is the same as that of Device Example 1, except that compound A-164 is used instead of the compound A-14 of the present invention as the first host in the emission layer (EML).
[0424] Device Comparative Example 1
[0425] The implementation of Device Comparative Example 1 is the same as that of Device Example 1, except that compound C is used instead of the compound A-14 of the present invention as the first host in the emission layer (EML).
[0426] The detailed device layer structures and thicknesses are shown in the following table. For the layers where more than one material is used, they are doped with different compounds in the recorded weight ratios.
[0427] Table 1 Partial Device Structures of Device Examples and Comparative Examples
[0428]
[0429]
[0430] The material structure used in the device is shown below:
[0431]
[0432]
[0433] Table 2 lists the 2 The maximum emission wavelength λ measured at max , power efficiency (PE) and initial brightness at 7500cd / m 2 The device life (LT97) is measured under the following conditions. The device life (LT97) refers to the time required for the device brightness to decay to 97% of its initial brightness.
[0434] Table 2 Device data
[0435] Device ID <![CDATA[λ max (nm)]]> PE [lm / W] LT97 (h) Example 1 622 28.5 1100 Example 2 623 28.5 731 Example 3 622 25.6 1022 Example 4 622 27.7 1379 Example 5 622 28.6 936 Comparative Example 1 623 21.5 14
[0436] discuss:
[0437] It can be seen from the data in Table 2 that the maximum emission wavelengths of the device embodiment and the device comparative example are substantially consistent.
[0438] The main difference between device Example 1 and device Comparative Example 1 is that the first compound is different. Comparative Example 1 uses a common triarylamine compound. Compared with Comparative Example 1, in terms of power efficiency, Example 1 has been greatly improved by 32.6%. Surprisingly, in terms of life, Example 1 has been improved by 78 times. These data show that the combination of the first compound selected by the present invention and the second compound selected by the present invention can obtain excellent device performance, especially life, when applied to an organic electroluminescent device relative to the combination of the first compound not selected by the present invention and the second compound selected by the present invention, which shows that the compound combination selected by the present invention is an excellent material combination.
[0439] Device Examples 2 to 5 use different first compounds selected by the present invention. Compared with Comparative Example 1, in terms of power efficiency, Examples 2 to 5 are also greatly improved, with the improvement rates being 32.6%, 19.1%, 28.8%, and 33%, respectively. In terms of life, Examples 2 to 4 are also unexpectedly greatly improved, with the improvement rates being 51 times, 72 times, 98 times, and 66 times. These data once again prove that the combination of the first compound selected by the present invention and the second compound selected by the present invention is an excellent material combination.
[0440] As can be seen from the above data, for an organic electroluminescent device using the combination of the first compound selected by the present invention and the second compound selected by the present invention, the hole transport and electron transport in the device can reach a more balanced state, enabling better recombination of electrons and holes in the device, thereby greatly improving the efficiency and lifespan of the device and exhibiting excellent device performance.
[0441] Based on the above results, it can be seen that an organic electroluminescent device containing the combination of the first compound selected by the present invention and the second compound selected by the present invention can achieve better device performance. Therefore, it has broad commercial development prospects and application value.
[0442] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be limiting.
Claims
1. An organic electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound; The first compound has a structure represented by Formula 1: in, X is selected from NR n , O or S; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Each time Z1 to Z4 appears, choose C, CR, or both. z or N, and one of Z1 to Z4 is selected from C and is connected to a six-membered ring containing W1 to W5; Each time W1 to W5 appears, choose C, CR, the same or different. w or N, and one of W1 to W5 is selected from C and connected to L; L 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, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof; and when the ring atoms of Ar1, Ar2 contain heteroatoms, the heteroatoms are selected from the group consisting of oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms; R w , 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; R z each occurrence is identically or differently 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 alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R z When the aryl group is selected from substituted aryl groups having 6 to 30 carbon atoms or substituted heteroaryl groups having 3 to 30 carbon atoms, the aryl group or heteroaryl group is substituted by one or more selected from deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclyl groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted Alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R w may optionally be linked to form a ring; The second compound has a structure represented by Formula 2: In formula 2, L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, 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; Ar 21 To Ar 23 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
2. The organic electroluminescent device according to claim 1, wherein R w , R n each occurrence is identically or differently 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 alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; R z each occurrence is identically or differently 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 cycloalkyl having 2 to 20 carbon atoms substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R z When selected from substituted groups, the group is substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted 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 The present invention is substituted by an alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, an unsubstituted arylgermanyl group having 6 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 a combination thereof.
3. The organic electroluminescent device according to claim 2, wherein X is selected from O or S; Preferably, X is selected from O.
4. The organic electroluminescent device according to claim 1 or 2, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, or a combination thereof; Preferably, wherein L is selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; More preferably, L is selected from a single bond, phenylene, naphthylene, biphenylene, or phenanthrenyl.
5. The organic electroluminescent device according to claim 1 or 2, wherein W1 to W5 are selected from C or CR w , and one of W1 to W5 is selected from C and connected to L; Preferably, one of W2, W3, W4 is C and connected to L.
6. The organic electroluminescent device according to claim 1 or 2, wherein R w , R z , R n each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, and combinations thereof; Preferably, R w , R z , R n is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, yl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.
7. The organic electroluminescent device according to claim 1 or 2, wherein Ar1, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4 to 10 ring carbon atoms, or a combination thereof; Ar is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms; Preferably, Ar1, Ar2 are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted silanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilanyl, substituted or unsubstituted , substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or a combination thereof; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted silanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilanyl, substituted or unsubstituted base, or a combination thereof; More preferably, Ar, Ar1, Ar2 are each identically or differently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, fluorenyl, silyl, base, or a combination thereof.
8. The organic electroluminescent device according to claim 1, wherein the first compound is selected from the group consisting of the following compounds: Optionally, hydrogen in the structures of Compound A-1 to Compound A-603 can be partially or completely replaced by deuterium.
9. The organic electroluminescent device according to claim 1, wherein the second compound has a structure shown in Formula 2-1: V1-V6 are selected from C, N or CR at each occurrence, either identically or differently v , and one of V1-V6 is C and connected to L 23 connected; L 21 To L 23 is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, 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; Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, 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, or a combination thereof; R v The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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; Adjacent substituent R v can optionally be linked to form a ring; Preferably, the second compound has a structure shown in Formula 2-1-1 or Formula 2-1-2: Wherein in formula 2-1-1, V1-V5 are selected from C, N or CR at each occurrence, the same or different v , V 11 -V 15 Each occurrence is selected from N or CR, either identically or differently v1 , and one of V1-V5 is C and connected to L 23 In formula 2-1-2, V1-V4 are selected from C, N or CR each time they appear, either identically or differently. v , V 11 -V 14 Each occurrence is selected from N or CR, either identically or differently v1 , and one of V1-V4 is C and connected to L 23 connected; V is selected from O, S or Se; L 21 To L 23 is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, 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; Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, 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, or a combination thereof; R v , R v1 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl radicals having 3 to 20 ring atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted alkene radicals 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; Adjacent substituent R v , R v1 Can optionally be linked to form a ring. 10 . The organic electroluminescent device according to claim 9 , wherein in formula 2-1-2, V is selected from O or S; preferably, V is O.
11. The organic electroluminescent device according to claim 9, wherein in formula 2-1-1, V1 to V5 are selected from C or CR v , V 11 To V 15 Each occurrence is the same or different selection from CR v1 In formula 2-1-2, V1 to V4 are selected from C or CR each time they appear, either identically or differently. v , V 11 To V 14 Each occurrence is the same or different selection from CR v1 ; Preferably, wherein said R v , R v1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; More preferably, in Formula 2-1-1, at least one of V1 to V5 is selected from CR v , or V 11 To V 15 At least one of CR v1 In formula 2-1-2, at least one of V1 to V4 is selected from CR v , or V 11 To V 14 At least one of CR v1 ; and said R v , R v1 and is selected, identically or differently on each occurrence, from substituted or unsubstituted aryl having 6 to 30 carbon atoms.
12. The organic electroluminescent device according to claim 9, wherein Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof; Preferably, wherein Ar 21 and Ar 22 is selected, at each occurrence, identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted indolocarbazolyl, or a combination thereof.
13. The organic electroluminescent device according to claim 9, wherein: L 21 To L 23 is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Preferably, wherein L 21 To L 23 Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, or a combination thereof.
14. The organic electroluminescent device according to claim 1, wherein the second compound is selected from the group consisting of: in, Optionally, hydrogen in the structures of Compound B-1 to Compound B-255 can be partially or completely replaced by deuterium. 15 . The organic electroluminescent device according to claim 1 , wherein the organic layer is a light-emitting layer, and the first compound and the second compound are host materials.
16. The organic electroluminescent device according to claim 15, wherein the light-emitting layer further comprises at least one phosphorescent light-emitting material.
17. The organic electroluminescent device according to claim 16, wherein the phosphorescent material is a metal complex having M(L a ) m (L b ) n (L c ) q The general formula of M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are respectively the first ligand, the second ligand and the third ligand coordinated with the M; L a , L b and L c can optionally be linked to form a multidentate ligand; L a , L b and L c can be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c Can be the same or different; L a Each occurrence is identical or different and is selected from the structure shown in Formula 3: in, Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring; Ring D and Ring E via U a and U b condense; U a and U b is selected identically or differently at each occurrence from C or N; R d and R e Each occurrence of the same or different means mono-, poly- or no-substitution; V 31 To V 34 Each occurrence is the same or different selection from CR v or N; R d , R e and R v Each occurrence is identically or differently 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 Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R d , R e and R v can optionally be linked to form a ring; L b and L c Each occurrence is identically or differently selected from any one of the following structures: in, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 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; Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
18. The organic electroluminescent device according to claim 1, which emits red light.
19. A compound composition comprising a first compound and a second compound, wherein the first compound has a structure represented by Formula 1: in, X is selected from NR n , O or S; Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Each time Z1 to Z4 appears, choose C, CR, or both. z or N, and one of Z1 to Z4 is selected from C and is connected to a six-membered ring containing W1 to W5; Each time W1 to W5 appears, choose C, CR, the same or different. w or N, and one of W1 to W5 is selected from C and connected to L; L 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, Ar2 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or a combination thereof; and when the ring atoms of Ar1, Ar2 contain heteroatoms, the heteroatoms are selected from the group consisting of oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms; R w , 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; R z each occurrence is identically or differently 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 alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; and when R z When the aryl group is selected from substituted aryl groups having 6 to 30 carbon atoms or substituted heteroaryl groups having 3 to 30 carbon atoms, the aryl group or heteroaryl group is substituted by one or more selected from deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclyl groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted Alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R w may optionally be linked to form a ring; The second compound has a structure represented by Formula 2: In formula 2, L 21 To L 23 is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, 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; Ar 21 To Ar 23 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
20. An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 18.
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