Organic electroluminescent device
By using a combination of fluorescent luminescent materials with specific structures and phosphorescent photosensitizers in organic electroluminescent devices, the performance problems of blue OLEDs have been solved, achieving improved device performance with narrow half-width and high efficiency.
Patent Information
- Application Number
- CN202510552396.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-04-29
- Publication Date
- 2026-11-06
AI Technical Summary
Existing organic light-emitting devices (OLEDs) suffer from problems such as blue unsaturation, short device lifetime, and high operating voltage in blue phosphorescent devices. Furthermore, the impact of the combination of phosphorescent sensitizers and fluorescent luminescent materials on device performance has not been fully studied, making it difficult to meet the requirements for narrower full width at half maximum (FWHM), higher efficiency, and longer lifetime.
By combining fluorescent luminescent materials with specific structures with phosphorescent photosensitizers, and by using fluorescent luminescent materials with the structure of Formula 1 and phosphorescent photosensitizers with the structure of Formula 2 in the organic layer, an organic electroluminescent device with narrow half-width and high efficiency is formed.
This achieved narrow half-width and higher efficiency in organic electroluminescent devices, thus improving device performance.
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Figure CN123056532A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electronic devices, such as organic electroluminescent devices. More particularly, it relates to an organic electroluminescent device comprising at least a first compound and a second compound in an organic layer. Background Technology
[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.
[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.
[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.
[0008] US20240188419A1 discloses an electroluminescent device comprising a first compound, a second compound, and a third compound, wherein at least two of the first, second, and third compounds contain a substituent R*, and R* has a structure Wherein [X] is a chemical moiety comprising at least one six-membered carbide ring, silyl group, germanyl group, or heterocyclic ring. This application uses compounds in specific embodiments. As a phosphorus photosensitizer, a compound containing a single boron atom is used. As a fluorescent luminescent material, this application focuses on the effect of specific substituents R* contained in the three compounds on device performance, and does not focus on the effect of combinations of phosphorescent photosensitizers with other specific structures and fluorescent luminescent materials with other specific structures on device performance.
[0009] The combination of phosphorescent photosensitizers and fluorescent luminescent materials has a significant impact on device performance. To meet the industry's ever-increasing demands, especially for narrower full width at half maximum (FWHM), higher device efficiency, and longer lifetime, further research and development are needed on the combination of different phosphorescent photosensitizers and fluorescent luminescent materials. Summary of the Invention
[0010] This invention aims to provide a novel organic electroluminescent device that comprises at least a first compound and a second compound in an organic layer to solve at least some of the aforementioned problems. The first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2. In this invention, the first compound is a fluorescent luminescent material, and the second compound is a phosphorescent photosensitizer. The organic electroluminescent device of this invention uses a phosphorescent photosensitizer with a specific structure to sensitize a fluorescent luminescent material with a specific structure, resulting in an organic electroluminescent device with a narrow full width at half maximum (FWHM) and higher efficiency.
[0011] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0012] anode,
[0013] cathode,
[0014] 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;
[0015] The first compound has a structure represented by Formula 1:
[0016]
[0017] In Formula 1, rings A, B, C, D and E are each independently selected from unsaturated carbon rings having 5-30 carbon atoms or unsaturated heterocycles having 3-30 carbon atoms.
[0018] Y1 is selected from N, P, CR', SiR' or GeR' each time it appears;
[0019] Y2 and Y3 are selected from O, S, NR', PR', CR'R', SiR'R' or GeR'R' each time they appear; when two R's exist at the same time, the two R's are the same or different;
[0020] L1, L2, and L3 are selected from the following groups, either identically or differently, each time they appear: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof;
[0021] n1, n2, n3 are selected from 0 or 1 each time they appear, either in the same or different ways.
[0022] R a1 R a2 R a3 R a4 R a5 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0023] R', R L1 R a1 R a2 R a3 R a4 R a5Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0024] Adjacent substituents R', R L1 R a1 R a2 R a3 R a4 R a5 They can be arbitrarily connected to form a loop;
[0025] Wherein, the second compound has M(L) a (L) b It has the general formula and the structure represented by Equation 2:
[0026]
[0027] In Equation 2, M is selected from metals with a relative atomic mass greater than 40;
[0028] Ring F, ring G, and ring H are each independently selected from unsaturated carbon rings having 5-30 carbon atoms, unsaturated heterocycles having 3-30 carbon atoms, or combinations thereof; ring I is selected from unsaturated heterocycles having 1-30 carbon atoms.
[0029] A1 and A4 are each independently selected from single bonds, O, S, Se, (SiR) q R q ) y PR q NR q , (CR q R q ) y, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof; y is selected from 1, 2, 3, 4 or 5 each time it appears;
[0030] K1-K4 are each independently selected from a single bond, O or S;
[0031] X1-X3 are each independently selected from C or N;
[0032] R n Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0033] R q R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0034] Adjacent substituent R q R n They can be arbitrarily connected to form a loop;
[0035] Where R has the structure represented by Equation 2-1:
[0036]
[0037] In Formula 2-1, ring M and ring W are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof.
[0038] X5 and X6 are selected from C or N each time they appear, either the same or different.
[0039] X7 is selected from CR” or N each time it appears, either the same or different.
[0040] "*" indicates the connection position of Equation 2-1;
[0041] R m R w Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0042] R m R w The letter "R" is selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0043] Adjacent substituent R m R w They can be arbitrarily connected to form a ring.
[0044] According to another embodiment of the present invention, a display device is also disclosed, which includes an organic electroluminescent device, the specific structure of which is shown in any of the above embodiments.
[0045] This invention discloses a novel organic electroluminescent device, comprising at least a first compound and a second compound in an organic layer. The first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2. In this invention, the first compound is a fluorescent luminescent material, and the second compound is a phosphorus photosensitizer. The organic electroluminescent device of this invention uses a phosphorus photosensitizer with a specific structure to sensitize a fluorescent luminescent material with a specific structure, resulting in an organic electroluminescent device with a narrow full width at half maximum (FWHM) and higher efficiency. Attached Figure Description
[0046] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent devices disclosed herein.
[0047] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent devices disclosed herein. Detailed Implementation
[0048] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.
[0049] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.
[0050] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.
[0051] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.
[0052] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.
[0053] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.
[0054] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0055] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.
[0056] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0057] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.
[0058] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0059] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.
[0060] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
[0061] Definition of the term "substituent group"
[0062] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0063] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0064] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.
[0065] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.
[0066] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.
[0067] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.
[0068] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.
[0069] Heterocyclic groups – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. Additionally, heterocyclic groups may optionally be substituted.
[0070] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.
[0071] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.
[0072] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.
[0073] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0074] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.
[0075] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.
[0076] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. An alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.
[0077] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.
[0078] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.
[0079] In this disclosure, unless otherwise defined, the term "substituted alkyl", "substituted cycloalkyl", "substituted heteroalkyl", "substituted heterocyclic", "substituted aralkyl", "substituted alkoxy", "substituted aryl", "substituted alkenyl", "substituted alkynyl", "substituted heteroaryl", "substituted alkylsilyl", "substituted arylsilyl", "substituted alkylgermanium", "substituted arylgermanium", "substituted amino", "substituted acyl", "substituted carbonyl", and "substituted carboxylic acid" are used interchangeably. The substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl groups. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms. Cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, and unsubstituted alkyne groups having 6-30 carbon atoms. Aryl, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof with 0-20 carbon atoms.
[0080] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.
[0081] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.
[0082] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.
[0083] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0084] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:
[0085]
[0086] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:
[0087]
[0088] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:
[0089]
[0090] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:
[0091]
[0092] According to one embodiment of the present invention, an electroluminescent device is disclosed, comprising:
[0093] anode,
[0094] cathode,
[0095] 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;
[0096] The first compound has a structure represented by Formula 1:
[0097]
[0098] In Formula 1, rings A, B, C, D and E are each independently selected from unsaturated carbon rings having 5-30 carbon atoms or unsaturated heterocycles having 3-30 carbon atoms.
[0099] Y1 is selected from N, P, CR', SiR' or GeR' each time it appears;
[0100] Y2 and Y3 are selected from O, S, NR', PR', CR'R', SiR'R' or GeR'R' each time they appear; when two R's exist at the same time, the two R's are the same or different;
[0101] L1, L2, and L3 are selected from the following groups, either identically or differently, each time they appear: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof;
[0102] n1, n2, n3 are selected from 0 or 1 each time they appear, either in the same or different ways.
[0103] R a1 R a2 R a3 R a4 R a5 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0104] R', R L1 R a1 R a2 R a3 R a4 R a5Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0105] Adjacent substituents R', R L1 R a1 R a2 R a3 R a4 R a5 They can be arbitrarily connected to form a loop;
[0106] Wherein, the second compound has M(L) a (L) b It has the general formula and the structure represented by Equation 2:
[0107]
[0108] In Equation 2, M is selected from metals with a relative atomic mass greater than 40;
[0109] Ring F, ring G, and ring H are each independently selected from unsaturated carbon rings having 5-30 carbon atoms, unsaturated heterocycles having 3-30 carbon atoms, or combinations thereof; ring I is selected from unsaturated heterocycles having 1-30 carbon atoms.
[0110] A1 and A4 are each independently selected from single bonds, O, S, Se, (SiR) q R q ) y PR q NR q , (CR q R q ) y, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof; y is selected from 1, 2, 3, 4 or 5 each time it appears;
[0111] K1-K4 are each independently selected from a single bond, O or S;
[0112] X1-X3 are each independently selected from C or N;
[0113] R n Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0114] R q R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0115] Adjacent substituent R q R n They can be arbitrarily connected to form a loop;
[0116] Where R has the structure represented by Equation 2-1:
[0117]
[0118] In Formula 2-1, ring M and ring W are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof.
[0119] X5 and X6 are selected from C or N each time they appear, either the same or different.
[0120] X7 is selected from CR” or N each time it appears, either the same or different.
[0121] "*" indicates the connection position of Equation 2-1;
[0122] R m R w Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0123] R m R w The letter "R" is selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0124] Adjacent substituent R m R w They can be arbitrarily connected to form a ring.
[0125] In this paper, "unsaturated carbon ring" includes aromatic unsaturated carbon ring and non-aromatic unsaturated carbon ring, and "unsaturated heterocycle" includes aromatic unsaturated heterocycle and non-aromatic unsaturated heterocycle.
[0126] In this paper, in Equation 1, when n1 is 0, it means that ring B and ring D are not connected; when n2 is 0, it means that ring C and ring E are not connected; when n3 is 0, it means that ring B and ring C are not connected.
[0127] In this paper, "adjacent substituents R', R L1 R a1 R a2 R a3 Ra4 R a5 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R L1 Between the two substituents R a1 Between the two substituents R a2 Between the two substituents R a3 Between the two substituents R a4 Between the two substituents R a5 Between, substituent R a1 and R a4 Between, substituent R a1 and R a5 Between, substituent R a2 and R a3 Between, substituent R a2 and R a4 Between, substituent R a3 and R a5 Between, substituents R' and R a1 Between, substituents R' and R a2 Between, substituents R' and R a3 Between, substituents R' and R a4 Between, substituents R' and R a5 Between, substituent R L1 and R a1 Between, substituent R L1 and R a2 Between, substituent R L1 and R a3 Between, substituent R L1 and R a4 Between, and substituent R L1 and R a5 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0128] In this paper, in Equation 2, when A1 is selected as a single bond, it indicates that ring F and ring G are directly connected by a single bond. When K1 or K2 is selected as a single bond, it indicates that ring F or ring G is directly connected to metal M by a single bond.
[0129] In this paper, the connection of A1 with ring F and ring G in Equation 2 is intended to indicate that A1 in Equation 2 can be connected to any ring atom in ring F or ring G, and not only to the case where A1 is connected to the atom in ring F adjacent to X1 or the atom in ring G adjacent to X2.
[0130] In this paper, "adjacent substituent R" q R n"Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R q Between the two substituents R n Between, and substituent R q and R n Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0131] In this paper, "adjacent substituent R" m R w "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R m Between the two substituents R w Between, and substituent R m and R w Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0132] According to one embodiment of the present invention, in Formula 1, rings A, B, C, D and E are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-30 carbon atoms or heteroaromatic rings having 3-30 carbon atoms.
[0133] According to one embodiment of the present invention, in Formula 1, rings A, B, C, D and E are selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 3-18 carbon atoms each time they appear.
[0134] According to one embodiment of the present invention, wherein, in Formula 1, rings A, B, C, D, and E, each time they appear, are selected from the same or different groups of benzene rings, pyridine rings, naphthyl rings, phenanthrene rings, anthracene rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, dibenzofuran rings, benzothiophene rings, dibenzothiophene rings, dibenzothiophene rings, dibenzoselenene rings, cyclopentadiene rings, furan rings, thiophene rings, thiophene rings, or combinations thereof.
[0135] According to one embodiment of the present invention, the first compound has a structure represented by formula 1-1:
[0136]
[0137] Among them, Y1 is selected from N, P, CR', SiR' or GeR' each time it appears;
[0138] Y2 and Y3 are selected from O, S, NR', PR', CR'R', SiR'R' or GeR'R' each time they appear; when two R's exist at the same time, the two R's are the same or different.
[0139] L1, L2, and L3 are selected from the following groups, either identically or differently, each time they appear: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof;
[0140] n1, n2, n3 are selected from 0 or 1 each time they appear, either in the same or different ways.
[0141] R a2 R a3 R a4 R a5 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0142] R', R L1 R a1 R a2 R a3 R a4 R a5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0143] Adjacent substituents R', RL1 R a1 R a2 R a3 R a4 R a5 They can be arbitrarily connected to form a ring.
[0144] According to one embodiment of the present invention, Y1 is selected from N, P or CR'; Y2 and Y3 are selected from O, NR', PR' or CR'R' each time they appear.
[0145] According to one embodiment of the present invention, Y1 is selected from N; Y2 and Y3 are selected from O or NR' each time they appear.
[0146] According to one embodiment of the present invention, Y1 is selected from N; Y2 and Y3 are selected from NR'.
[0147] According to one embodiment of the present invention, L1, L2 or L3 is selected from single bonds.
[0148] According to one embodiment of the present invention, n1 and n2 are both 0, n3 is 1 and L3 is a single bond.
[0149] According to one embodiment of the present invention, the first compound contains at least two B atoms.
[0150] According to one embodiment of the present invention, the first compound contains only two B atoms.
[0151] According to one embodiment of the present invention, in Formula 1, when Y2 is selected from NR', PR', CR'R', SiR'R' or GeR'R', R' can be connected to ring D to form a ring.
[0152] According to one embodiment of the present invention, in Formula 1, when Y3 is selected from NR', PR', CR'R', SiR'R' or GeR'R', R' can be connected to ring E to form a ring.
[0153] According to one embodiment of the present invention, the first compound has a structure represented by formula 1-1-1:
[0154]
[0155] Among them, L1, L2, L3, L4, and L5 are selected from the following groups each time they appear, either identically or differently: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1, substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof;
[0156] n1, n2, n3, n4, and n5 are selected from 0 or 1 each time they appear;
[0157] R a2 R a3 R a4 R a5 R a6 R a7 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0158] R L1 R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0159] Adjacent substituent R L1 R a1 R a2 R a3 R a4 R a5 R a6 R a7 They can be arbitrarily connected to form a ring.
[0160] In this embodiment, "adjacent substituent R" L1 R a1 R a2 R a3 R a4 R a5 R a6 R a7 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a2 Between the two substituents R a3 Between the two substituents R a4 Between the two substituents R a5 Between the two substituents R a6 Between the two substituents R a7 Between, substituent R a1 and R a6 Between, substituent R a1 and R a7 Between, substituent R a2 and R a3 Between, substituent R a2 and R a4 Between, substituent R a3 and R a5 Between, substituent R a4 and R a6 Between, substituent R a5 and R a7 Between, substituent R a6 and R a7 Between, substituent R L1 and R a2 Between, substituent R L1 and R a3 Between, substituent R L1 and R a4 Between, and substituent R L1 and R a5 Between, substituent R L1 and R a6 Between, and substituent R L1 and R a7 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0161] According to one embodiment of the present invention, n1, n2 are selected from 0, and n3, n4, n5 are selected from 1.
[0162] According to one embodiment of the present invention, n1 and n2 are selected from 0, n3, n4 and n5 are selected from 1, and L3, L4 and L5 are all selected from single bonds.
[0163] According to one embodiment of the present invention, wherein the R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-12 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-6 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-12 carbon atoms, substituted or unsubstituted amino groups having 0-12 carbon atoms, and combinations thereof.
[0164] According to one embodiment of the present invention, wherein the R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, trimethylgermanyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthracene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.
[0165] According to one embodiment of the present invention, wherein the R a1 R a2 R a3 R a4 R a5 R a6 R a7At least one of them, each time appearing identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0166] According to one embodiment of the present invention, wherein the R a1 R a2 R a3 R a4 R a5 R a6 R a7 At least one of them, each time appearing identically or differently, is selected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl having 1-6 carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, substituted or unsubstituted arylsilyl having 6-12 carbon atoms, substituted or unsubstituted alkylgermanium having 3-6 carbon atoms, substituted or unsubstituted arylgermanium having 6-12 carbon atoms, substituted or unsubstituted amino having 0-12 carbon atoms, and combinations thereof.
[0167] According to one embodiment of the present invention, wherein the R a1 R a2 R a3 R a4 R a5 R a6 R a7At least one of them, each time appearing, is selected from the group consisting of: deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, trimethylgermanyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthracene, indyl, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.
[0168] According to one embodiment of the present invention, the first compound is selected from the group consisting of compounds BD1-1 to BD1-10, compounds BD2-1 to BD2-10, compounds BD3-1 to BD3-16, compounds BD4-1 to BD4-16, compounds BD5-1 to BD5-16, and compounds BD6-1 to BD6-13; the specific structures of compounds BD1-1 to BD1-10, BD2-1 to BD2-10, BD3-1 to BD3-16, BD4-1 to BD4-16, BD5-1 to BD5-16, and BD6-1 to BD6-13 are given in claim 9.
[0169] According to one embodiment of the present invention, the hydrogen in the structures of compounds BD1-1 to BD1-10, BD2-1 to BD2-10, BD3-1 to BD3-16, BD4-1 to BD4-16, BD5-1 to BD5-16, and BD6-1 to BD6-13 can be partially or completely replaced by deuterium.
[0170] According to one embodiment of the present invention, the maximum emission wavelength λ of the photoluminescence spectrum of the first compound is... max-PL-1 The wavelength range is 450nm to 500nm.
[0171] According to one embodiment of the present invention, the maximum emission wavelength λ of the photoluminescence spectrum of the first compound is... max-PL-1 The wavelength range is 450nm to 470nm.
[0172] According to one embodiment of the present invention, the maximum emission wavelength λ of the photoluminescence spectrum of the first compound is... max-PL-1 The wavelength range is 455nm to 465nm.
[0173] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 45nm.
[0174] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 35nm.
[0175] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 30nm.
[0176] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 25nm.
[0177] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 20nm.
[0178] According to one embodiment of the present invention, in Formula 2, the metal M is selected from the group consisting of Cu, Ag, Au, Zn, Ru, Rh, Pd, Os, Ir and Pt.
[0179] According to one embodiment of the present invention, in Formula 2, the metal M is selected from Pt or Pd.
[0180] According to one embodiment of the present invention, in Formula 2, the metal M is selected from Pt.
[0181] According to one embodiment of the present invention, in Formula 2, ring F, ring G, and ring H are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-30 carbon atoms, or heteroaromatic rings having 3-30 carbon atoms; ring I is selected from unsaturated heterocycles having 3-30 carbon atoms each time it appears.
[0182] According to one embodiment of the present invention, in Formula 2, ring F, ring G, and ring H are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms; ring I is selected from unsaturated heterocycles having 3-18 carbon atoms each time it appears.
[0183] According to one embodiment of the present invention, in Formula 2, ring F, ring G, and ring H are each independently selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, or a thiophene ring; and ring I is selected from an imidazole carbene ring or a benzoimidazole carbene ring each time it appears.
[0184] According to one embodiment of the present invention, in Formula 2, K1-K4 are selected from single bonds.
[0185] According to one embodiment of the present invention, the second compound has a structure represented by one of formulas 3-1 to 3-18:
[0186]
[0187]
[0188]
[0189] In this case, A4 is selected from single bonds, O, S, Se, (SiR) each time it appears, either the same or different. q R q ) y PR q NR q , substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof; y is selected from 1, 2 or 3 each time it appears, either identically or differently.
[0190] U1-U 20 Each time it appears, it is selected from CR in the same or different ways. n Or N;
[0191] R u Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0192] R N R q R n and R uEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0193] Adjacent substituent R N R q R n and R u They can be arbitrarily connected to form a loop;
[0194] Where R has the structure represented by Equation 2-1:
[0195]
[0196] In Formula 2-1, ring M and ring W are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof.
[0197] X5 and X6 are selected from C or N each time they appear, either the same or different.
[0198] X7 is selected from CR” or N each time it appears, either the same or different.
[0199] "*" indicates the connection position of Equation 2-1;
[0200] R m R w Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0201] R m R wThe letter "R" is selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0202] Adjacent substituent R m R w They can be arbitrarily connected to form a ring.
[0203] In this embodiment, "adjacent substituent R" N R q R n and R u "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R q Between the two substituents R n Between the two substituents R u Between, substituent R N and R n Between, substituent R n and R u Between, and substituent R q and R n Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0204] According to one embodiment of the present invention, the second compound has a structure represented by formula 3-1 or formula 3-2.
[0205] According to one embodiment of the present invention, the second compound has a structure represented by formula 3-2.
[0206] According to one embodiment of the present invention, the A4 is selected from a single bond, O or S.
[0207] According to one embodiment of the present invention, A4 is selected from O.
[0208] According to one embodiment of the present invention, wherein the U1-U 20 Each time it appears, it is selected from CR in the same or different ways. n And the R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof.
[0209] According to one embodiment of the present invention, wherein the R n Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazole, indolyl, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0210] According to one embodiment of the present invention, wherein U1-U 20 At least one of them is selected from CR each time it appears, either identically or differently. n ; and the R nEach time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. , substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0211] According to one embodiment of the present invention, at least one of U1-U4 is selected from CR each time it occurs, either identically or differently. n ; and the R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. , substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0212] According to one embodiment of the present invention, U3 is selected from CR n And the R nChoose from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... The following are substituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0213] According to one embodiment of the present invention, U3 is selected from CR n And the R n Choose from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, 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, and combinations thereof.
[0214] According to one embodiment of the present invention, U3 is selected from CR n And the R n Selected from substituted or unsubstituted alkyl groups having 4 to 20 carbon atoms.
[0215] According to one embodiment of the present invention, U3 is selected from CR n And the R n Selected from substituted or unsubstituted alkyl groups having 5 to 20 carbon atoms.
[0216] According to one embodiment of the present invention, U3 is selected from CR n And the R nChoose from the following groups: n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated neopentyl, and combinations thereof.
[0217] According to one embodiment of the present invention, wherein R has a structure represented by Equation 2-1-1:
[0218]
[0219] In Equation 2-1-1, M1 to M5 are each independently selected from CR. m Or N;
[0220] W1 to W4 are each independently selected from CR w Or N;
[0221] R m and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0222] Adjacent substituent R m R w They can be arbitrarily connected to form a ring.
[0223] According to one embodiment of the present invention, wherein R has a structure represented by equation 2-1-2:
[0224]
[0225] In Equation 2-1-2, M1 to M 10 Each independently selected from CR m Or N;
[0226] W1 to W3 are each independently selected from CR w Or N;
[0227] R m and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0228] According to one embodiment of the present invention, wherein M1 to M 10 Each independently selected from CR m .
[0229] According to one embodiment of the present invention, wherein W1 to W3 are each independently selected from CR w .
[0230] According to one embodiment of the present invention, wherein the R m and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof.
[0231] According to one embodiment of the present invention, wherein M1 to M 10 Each can be independently selected from CH or CD.
[0232] According to one embodiment of the present invention, at least one of W1 to W3 is selected from CR each time it occurs, either identically or differently. w And the R w Each time it appears, it is selected from the group consisting of the same or different groups: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted groups having Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms.
[0233] According to one embodiment of the present invention, W2 is selected from CR w And the R w The group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof.
[0234] According to one embodiment of the present invention, W2 is selected from CR w And the R wChoose from the group consisting of: substituted or unsubstituted alkyl groups having 4 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
[0235] According to one embodiment of the present invention, W2 is selected from CR w And the R w Choose from the group consisting of: n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, partially deuterated or fully deuterated n-butyl, partially deuterated or fully deuterated isobutyl, partially deuterated or fully deuterated tert-butyl, partially deuterated or fully deuterated cyclopentyl, partially deuterated or fully deuterated cyclohexyl, and partially deuterated or fully deuterated neopentyl.
[0236] According to one embodiment of the present invention, wherein the second compound has Pt(L) a (L) b The structure represented by the general formula, where L a and L b These are the first and second ligands that coordinate with metallic Pt, respectively. For example... In other words, the L a The structure represented by equation A: In formula A, "#" indicates a relationship with L. b The location of the connection; the L b The structure represented by equation B: In which equation B Indicates with L a The location of the connection.
[0237] According to one embodiment of the present invention, the second compound has Pt(L) a (L) b The structure is represented by ) where L a and L b These are the first and second ligands that coordinate with metallic Pt, respectively, and the L a Choose freely L a 1-1 to L a 1-25 and L a 2-1 to L a Groups consisting of 2-6, wherein L b Choose freely L b 1-1 to L b 1-8 and L b 2-1 to L b Group 2-22; the L a 1-1 to La 1-25 and L a 2-1 to L a 2-6, L b 1-1 to L b 1-8 and L b 2-1 to L b For the specific structure of 2-22, please refer to claim 20.
[0238] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds Pt1 to Pt83, wherein compounds Pt1 to Pt83 have Pt(L) a (L) b The specific structures of compounds Pt1 to Pt83 are described in claim 20.
[0239] According to one embodiment of the present invention, the maximum emission wavelength λ in the photoluminescence spectrum of the second compound is... max-PL-2 The wavelength range is 440nm to 500nm.
[0240] According to one embodiment of the present invention, the maximum emission wavelength λ in the photoluminescence spectrum of the second compound is... max-PL-2 The wavelength range is 440nm to 470nm.
[0241] According to one embodiment of the present invention, the maximum emission wavelength λ in the photoluminescence spectrum of the second compound is... max-PL-2 The wavelength range is 455nm to 465nm.
[0242] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the second compound is... PL-2 Less than or equal to 45nm.
[0243] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the second compound is... PL-2 Less than or equal to 35nm.
[0244] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the second compound is... PL-2 Less than or equal to 30nm.
[0245] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the second compound is... PL-2 Less than or equal to 25nm.
[0246] According to one embodiment of the present invention, the full width at half maximum (FWHM) of the photoluminescence spectrum of the second compound is... PL-2Less than or equal to 20nm.
[0247] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the first compound is a fluorescent light-emitting material, and the second compound is a phosphorescent photosensitizer.
[0248] According to one embodiment of the present invention, the first compound is a delayed fluorescence material.
[0249] According to one embodiment of the present invention, the light-emitting layer further comprises a first host compound and a second host compound.
[0250] According to one embodiment of the present invention, wherein the first host compound and the second host compound are each independently selected from compounds comprising at least one of the following chemical groups: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0251] According to one embodiment of the present invention, the first host compound has a structure represented by one of Formulas 5 to 7:
[0252]
[0253] In Equation 5, Z1 to Z3 are selected from CR4 or N each time they appear, and at least one of Z1 to Z3 is N;
[0254] Each time L appears, it is selected from the following groups, either the same or different: single bond, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof.
[0255] In Equations 6 and 7, Z4 is selected from CR4 or N each time it appears, and at least one Z4 is N;
[0256] Z is selected from O or S each time it appears, either identically or differently;
[0257] R1-R4, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0258] Adjacent substituents R4 can optionally connect to form a ring.
[0259] In this document, "adjacent substituents R4 can optionally connect to form a ring" is intended to mean that two adjacent substituents R4 can connect to form a ring. Obviously, two adjacent substituents R4 may also not connect to form a ring.
[0260] According to one embodiment of the present invention, the first host compound has a structure represented by formula 5-1 or formula 6-1:
[0261]
[0262] In Equation 5-1,
[0263] R1 and R2 are each independently selected from substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0264] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0265] In Equation 6-1,
[0266] Z is selected from O or S;
[0267] Z 41 -Z 48Each occurrence is either identical or different and is selected from CR4, CR4', or N, and Z 41 -Z 48 At least one of them is selected from N, and at least one is selected from CR4';
[0268] R4' is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0269] R L R4, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0270] Adjacent substituents R4 can optionally connect to form a ring.
[0271] According to one embodiment of the invention, the L is selected from the group consisting of the same or different groups each time it appears: single bond, substituted or unsubstituted aryl group having 6-18 carbon atoms, substituted or unsubstituted heteroaryl group having 3-18 carbon atoms, and combinations thereof.
[0272] According to one embodiment of the present invention, wherein the L is selected from the group consisting of the same or different each time it appears: single bond, phenylene, biphenylene, fluorene, triphenylene, furanyl, thiophene, dibenzofuranyl, dibenzothiophene, and combinations thereof.
[0273] According to one embodiment of the present invention, wherein the R LEach time it appears, it is selected from the group consisting of the same or different groups of the following: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
[0274] According to one embodiment of the present invention, wherein the R L Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, either identically or differently.
[0275] According to one embodiment of the present invention, wherein the R L Each time it appears, it is selected from the group consisting of the following, either the same or different: phenyl, biphenyl, triphenylene, indole, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0276] According to one embodiment of the invention, wherein R1 to R4, each time they appear, are selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
[0277] According to one embodiment of the invention, wherein R1 to R4 are selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof, each time they appear.
[0278] According to one embodiment of the present invention, wherein R1 to R4, each time they appear, are selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, triazineyl, and combinations thereof.
[0279] According to an embodiment of the present invention, in formula 6-1, the Z 41 -Z 48 At least one of them is selected from N, and at least two are selected from CR4'.
[0280] According to an embodiment of the present invention, in formula 6-1, the Z 41 -Z 48Only one of them is selected from N, and only two are selected from CR4'.
[0281] According to an embodiment of the present invention, in formula 6-1, the Z 42 Selected from N, the Z 41 and Z 46 Selected from CR4'.
[0282] According to one embodiment of the present invention, the first host compound is selected from the group consisting of compounds N-1-1 to N-1-60, compounds N-2-1 to N-2-35, and compounds N-3-1 to N-3-9.
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290] According to one embodiment of the present invention, the hydrogen in the structures of compounds N-1-1 to N-1-53, N-1-58, N-2-1 to N-2-32, and N-3-1 to N-3-7 can be partially or completely replaced by deuterium.
[0291] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 8:
[0292]
[0293] In Equation 8,
[0294] L 11 Selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0295] Ar 11 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino groups having 0-30 carbon atoms, or combinations thereof;
[0296] R6, when appearing in the same or different instances, indicates monosubstitution, polysubstitution, or no substitution.
[0297] R6, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0298] Adjacent substituents R6 can optionally connect to form a ring.
[0299] In this document, "adjacent substituents R6 can optionally connect to form a ring" is intended to mean that two adjacent substituents R6 can connect to form a ring. Obviously, two adjacent substituents R6 may also not connect to form a ring.
[0300] According to one embodiment of the present invention, the second host compound has a structure represented by formula 8-1 or formula 8-2:
[0301]
[0302] L 11 L 12 Selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0303] Ar 11 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino groups having 0-30 carbon atoms, or combinations thereof;
[0304] R6, when appearing in the same or different instances, indicates monosubstitution, polysubstitution, or no substitution.
[0305] R6, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0306] Adjacent substituents R6 can optionally connect to form a ring.
[0307] According to one embodiment of the present invention, the second host compound has a structure represented by formula 8-3 or formula 8-4:
[0308]
[0309] Ar 11 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino groups having 0-30 carbon atoms, or combinations thereof;
[0310] L 11 Selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0311] R6, when appearing in the same or different instances, indicates monosubstitution, polysubstitution, or no substitution.
[0312] R6, each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0313] Adjacent substituents R6 can optionally connect to form a ring.
[0314] According to one embodiment of the invention, R6, each time it appears, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof.
[0315] According to one embodiment of the invention, wherein R6 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof, each time it appears.
[0316] According to one embodiment of the invention, wherein R6, each time it appears, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
[0317] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compounds P-1 to P-38:
[0318]
[0319]
[0320]
[0321]
[0322] According to one embodiment of the present invention, the hydrogen in the structure of compounds P-1 to P-23, and compounds P-27 to P-38 can be partially or completely replaced by deuterium.
[0323] According to one embodiment of the present invention, the weight of the first main compound and the second main compound accounts for 65%-98.9% of the total weight of the light-emitting layer material, the weight of the second compound accounts for 1%-30% of the total weight of the light-emitting layer material, and the weight of the first compound accounts for 0.1%-5% of the total weight of the light-emitting layer material.
[0324] According to one embodiment of the present invention, the weight ratio of the first main compound and the second main compound to the total weight of the luminescent layer material is 82%-94.5%, the weight ratio of the second compound to the total weight of the luminescent layer material is 5%-15%, and the weight ratio of the first compound to the total weight of the luminescent layer material is 0.5%-3%.
[0325] According to one embodiment of the present invention, the weight ratio of the first main compound and the second main compound to the total weight of the luminescent layer material is 86.5%-91.5%, the weight ratio of the second compound to the total weight of the luminescent layer material is 8%-12%, and the weight ratio of the first compound to the total weight of the luminescent layer material is 0.5%-1.5%.
[0326] According to one embodiment of the present invention, the device emits blue light.
[0327] According to one embodiment of the present invention, the device emits deep blue light.
[0328] According to one embodiment of the present invention, the device emits white light.
[0329] According to one embodiment of the present invention, the maximum emission wavelength of the device is 460nm-470nm.
[0330] According to one embodiment of the present invention, the organic electroluminescent device emits fluorescence.
[0331] According to one embodiment of the present invention, the organic electroluminescent device emits delayed fluorescence.
[0332] According to one embodiment of the present invention, the fluorescent luminescent material is a light emitter.
[0333] According to one embodiment of the present invention, a display device is disclosed, which includes an organic electroluminescent device as described in any of the foregoing embodiments.
[0334] Combination with other materials
[0335] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0336] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0337] The present invention does not limit the preparation methods of the selected first and second compounds. Those skilled in the art can prepare them using conventional synthetic methods, or they can be easily obtained by referring to the preparation methods in the prior art. For example, the first compound can be prepared by referring to the Journal of the American Chemical Society, 2020, 142(46), 19468-19472 (DOI:10.1021 / jacs.0c10081), and the second compound can be prepared by referring to US20210284672A1, US20190119312A1, US20210359227A1, etc. The preparation methods will not be described in detail here.
[0338] The fabrication method of organic electroluminescent devices is not limited. The fabrication method of the following device embodiments is merely an example and should not be construed as limiting. Those skilled in the art can reasonably improve the fabrication method of the following device embodiments based on existing technology. For example, the proportion of various materials in the light-emitting layer is not particularly limited. Those skilled in the art can reasonably select within a certain range based on existing technology. For instance, based on the total weight of the light-emitting layer materials, the main material can account for 75%-98%, the metal complex can account for 1%-20%, and the fluorescent light-emitting material can account for 1%-5%; or the main material can account for 85%-98%, the metal complex can account for 1%-13%, and the fluorescent light-emitting material can account for 1%-2%. Furthermore, the main material consists of two materials, wherein the ratio of the two main materials to the main material can be 99:1 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 70:30 to 30:70. In the embodiments of the device, the characteristics of the device are also tested using conventional equipment in the art (including but not limited to vapor deposition machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) and methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the sample reliably and unaffected, the above-mentioned related content will not be elaborated in this patent.
[0339] In this invention, the maximum emission wavelength λ of the photoluminescence spectrum max-PL and half-height full-width FWHM- PL The testing method is as follows:
[0340] The photoluminescence (PL) spectra of the test compounds were determined using a Prism F98 fluorescence spectrophotometer manufactured by Shanghai Prism Technology Co., Ltd. The test compounds were dissolved in toluene to prepare 1×10⁻⁶ ppm solutions. -6 A solution with a concentration of mol / L was prepared by purging nitrogen gas into the test solution for 5 minutes to remove oxygen. The test solution was then placed in a quartz sample tube and excited at room temperature (298 K) using light of the maximum absorption wavelength of the test compound, and its emission spectrum was measured. The emission spectrum has a maximum emission wavelength λ. max-PL and half-height full-width FWHM- PL (Also known as half-peak width or half-peak height, it is the width of the peak at half its height. It is the distance between two points where the straight line drawn through the midpoint of the peak height intersects the two sides of the peak.)
[0341] As an example, the maximum emission wavelength λ of the photoluminescence spectrum of the following compounds was determined using the method described above. max-PL Full width at half maximum (FWHM) in photoluminescence spectrum PLThe specific results are shown in Table 1:
[0342] Table 1. Photoluminescence spectral data of the compounds
[0343] Fluorescent materials <![CDATA[λ max-PL-1 (nm)]]> <![CDATA[FWHM- PL-1 (nm)]]> BD-3-4 461 18.14
[0344] Device Examples
[0345] Device Example 1
[0346] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -7 In the case of Torr, deposition was performed sequentially on the ITO anode via thermal vacuum evaporation at a rate of 0.2–2 Å / s. Compounds HT and HI were co-deposited (weight ratio 97:3) as the hole injection layer (HIL), with a thickness of [missing information]. The vapor-deposited compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. The vapor-deposited compound P-21 was used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the first host compound N-3-2, the second host compound P-25, compound Pt27, and compound BD3-4 were co-deposited (weight ratio 34.9:52.1:12:1) as the emissive layer (EML), with a thickness of [missing information]. Compound N-3-2 was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited (weight ratio 40:60) as an electron transport layer (ETL), with a thickness of [missing information]. Finally, vapor deposition A thick layer of LiF was used as the electron injection layer, and it was deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover and desiccant to complete the device.
[0347] Device Example 2
[0348] The fabrication method of Device Example 2 is the same as that of Device Example 1, except that compound Pt27 is replaced by compound Pt29 in the light-emitting layer (EML).
[0349] Device Comparison Example 1
[0350] The device comparative example 1 was prepared in the same manner as device example 1, except that compound BD3-4 was replaced with compound BD in the light-emitting layer (EML).
[0351] Device Comparison Example 2
[0352] The fabrication method of Comparative Example 2 was the same as that of Comparative Example 1, except that the first host compound N-3-2, the second host compound P-25, and compound BD3-4 were co-deposited in the light-emitting layer (EML) as the light-emitting layer (weight ratio 39.6:59.4:1). ).
[0353] Device Comparison Example 3
[0354] The fabrication method of Comparative Example 3 was the same as that of Comparative Example 1, except that the first host compound N-3-2, the second host compound P-25, and compound Pt27 were co-deposited in the light-emitting layer (EML) as the light-emitting layer (weight ratio 35.1:52.9:12). ).
[0355] Device Comparison Example 4
[0356] The fabrication method of Comparative Example 4 was the same as that of Comparative Example 2, except that the first host compound N-3-2, the second host compound P-25, and compound Pt29 were co-deposited in the light-emitting layer (EML) as the light-emitting layer (weight ratio 35.1:52.9:12). ).
[0357] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.
[0358] Table 2 Partial device structures of device embodiments and device comparison examples.
[0359]
[0360] The material structure used in the device is shown below:
[0361]
[0362] At 10mA / cm 2 The CIE values of the embodiments and comparative examples were measured, and the maximum emission wavelength (λ) was measured. max The full width at half maximum (FWHM) and external quantum efficiency (EQE) are shown in Table 3.
[0363] Table 3 Device Data
[0364]
[0365]
[0366] discuss:
[0367] The only difference between Example 1 and Comparative Example 1 is the fluorescent luminescent material used in the luminescent layer. Example 1 uses the fluorescent luminescent material containing two boron atoms, as represented by Formula 1, selected in this invention, while Comparative Example 1 uses a fluorescent luminescent material containing one boron atom, commonly used in the prior art. As can be seen from the data in Table 3, compared to Comparative Example 1, the maximum emission wavelength of Example 1 remains unchanged, but the full width at half maximum (FWHM) is narrowed by 1 nm. More importantly, the external quantum efficiency of Comparative Example 1 is already at a high level; compared to Comparative Example 1, the external quantum efficiency of Example 1 is further significantly improved by 16.2%, which is quite remarkable.
[0368] Example 2 uses metal complexes with different structures as phosphorus photosensitizers. As shown in Table 3, Example 2 also has excellent device performance. Compared with Comparative Example 1, the maximum emission wavelength of Example 2 remains unchanged, the full width at half maximum (FWHM) is narrowed by 0.8 nm, and more importantly, the external quantum efficiency is greatly improved by 14.4%, demonstrating excellent device performance.
[0369] The only difference between Example 1 and Comparative Example 2 is that the emitting layer of Example 1 uses the metal complex selected in this invention as a phosphorescent sensitizer to sensitize the fluorescent emitting material selected in this invention, while the emitting layer of Comparative Example 2 only uses the fluorescent emitting material of this invention and does not use the metal complex as a phosphorescent sensitizer. As shown in Table 3, the maximum emission wavelengths of Example 1 and Comparative Example 2 are consistent, indicating that the light emitted by the device in Example 1 originates from the fluorescent emitting material. However, compared to the ordinary fluorescent emitting device of Comparative Example 2, Example 1 of this invention has a substantially comparable narrow half-width, and more importantly, the external quantum efficiency of Example 1 is increased by as much as 119.2%.
[0370] The only difference between Example 1 and Comparative Example 3, and between Example 2 and Comparative Example 4, is that the emitting layers of Examples 1 and 2 simultaneously used the metal complex and fluorescent emitting material selected in this invention, and the devices emitted fluorescence. In contrast, the emitting layers of Comparative Examples 3 and 4 only used the metal complex and did not use the fluorescent emitting material, and the devices emitted phosphorescence. As shown in Table 3, compared to the phosphorescent devices of Comparative Examples 3 and 4, the sensitized fluorescent devices of Examples 1 and 2 have a similarly narrow half-peak width. More importantly, compared to Comparative Example 3, the external quantum efficiency of Example 1 was significantly improved by 24.9%, and compared to Comparative Example 4, the external quantum efficiency of Example 2 was significantly improved by 22.6%.
[0371] In summary, this invention achieves excellent device performance by using a fluorescent luminescent material with a specific structure represented by Formula 1 in the luminescent layer, combined with a metal complex with a specific structure represented by Formula 2. This results in a narrow half-width at half-maximum and, in particular, higher external quantum efficiency, thus demonstrating broad application prospects.
[0372] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.
Claims
1. 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 Formula 1, rings A, B, C, D and E are each independently selected from unsaturated carbon rings having 5-30 carbon atoms or unsaturated heterocycles having 3-30 carbon atoms. Y1 is selected from N, P, CR', SiR' or GeR' each time it appears; Y2 and Y3 are selected from O, S, NR', PR', CR'R', SiR'R' or GeR'R' each time they appear; when two R's exist at the same time, the two R's are the same or different; L1, L2, and L3 are selected from the following groups, either identically or differently, each time they appear: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof; n1, n2, n3 are selected from 0 or 1 each time they appear, either in the same or different ways. R a1 R a2 R a3 R a4 R a5 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R', R L1 R a1 R a2 R a3 R a4 R a5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R', R L1 R a1 R a2 R a3 R a4 R a5 They can be arbitrarily connected to form a loop; Wherein, the second compound has M(L) a (L) b It has the general formula and the structure represented by Equation 2: In Equation 2, M is selected from metals with a relative atomic mass greater than 40; Ring F, ring G, and ring H are each independently selected from unsaturated carbon rings having 5-30 carbon atoms, unsaturated heterocycles having 3-30 carbon atoms, or combinations thereof; ring I is selected from unsaturated heterocycles having 1-30 carbon atoms. A1 and A4 are each independently selected from single bonds, O, S, Se, (SiR) q R q ) y PR q NR q , (CR q R q ) y , substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof; y is selected from 1, 2, 3, 4 or 5 each time it appears; K1-K4 are each independently selected from a single bond, O or S; X1-X3 are each independently selected from C or N; R n Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution; R q R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R q R n They can be arbitrarily connected to form a loop; Where R has the structure represented by Equation 2-1: In Formula 2-1, ring M and ring W are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof. X5 and X6 are selected from C or N each time they appear, either the same or different. X7 is selected from CR” or N each time it appears, either the same or different. "*" indicates the connection position of Equation 2-1; R m R w Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution; R m R w The letter "R" is selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R m R w They can be arbitrarily connected to form a ring.
2. The organic electroluminescent device as described in claim 1, wherein, In Formula 1, rings A, B, C, D and E are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-30 carbon atoms or heteroaromatic rings having 3-30 carbon atoms. Preferably, the rings A, B, C, D and E are selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 3-18 carbon atoms each time they appear; More preferably, the rings A, B, C, D, and E, when appearing in the same or different forms, are selected from benzene rings, pyridine rings, naphthyl rings, phenanthrene rings, anthracene rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, dibenzofuran rings, benzothiophene rings, dibenzothiophene rings, dibenzoselenene rings, cyclopentadiene rings, furan rings, thiophene rings, thiophene rings, or combinations thereof.
3. The organic electroluminescent device as described in claim 2, wherein, The first compound has a structure represented by Formula 1-1: Among them, Y1 is selected from N, P, CR', SiR' or GeR' each time it appears; Y2 and Y3 are selected from O, S, NR', PR', CR'R', SiR'R' or GeR'R' each time they appear; when two R's exist at the same time, the two R's are the same or different. L1, L2, and L3 are selected from the following groups, either identically or differently, each time they appear: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof; n1, n2, n3 are selected from 0 or 1 each time they appear, either in the same or different ways. R a2 R a3 R a4 R a5 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R', R L1 R a1 R a2 R a3 R a4 R a5 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituents R', R L1 R a1 R a2 R a3 R a4 R a5 They can be arbitrarily connected to form a ring.
4. The organic electroluminescent device as described in claim 3, wherein, Y1 is selected from N, P or CR'; Y2 and Y3 are selected from O, NR', PR' or CR'R' each time they appear; Preferably, Y1 is selected from N; Y2 and Y3 are selected from O or NR' each time they appear, either the same or different.
5. The organic electroluminescent device as described in claim 3, wherein, L1, L2, or L3 is selected from single bonds; Preferably, n1 and n2 are both 0, n3 is 1, and L3 is a single bond.
6. The organic electroluminescent device as described in claim 3, wherein, The first compound has a structure represented by formula 1-1-1: Among them, L1, L2, L3, L4, and L5 are selected from the following groups each time they appear, either identically or differently: single bond, O, S, Se, SiR. L1 R L1 NR L1 PR L1 , substituted or unsubstituted vinylenes, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, and combinations thereof; n1, n2, n3, n4, and n5 are selected from 0 or 1 each time they appear; R a2 R a3 R a4 R a5 R a6 R a7 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R L1 R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R L1 R a1 R a2 R a3 R a4 R a5 R a6 R a7 They can be arbitrarily connected to form a loop; Preferably, n1 and n2 are selected from 0, and n3, n4, and n5 are selected from 1; More preferably, L3, L4, and L5 are all selected from single bonds.
7. The organic electroluminescent device as described in claim 6, wherein, The R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-12 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-6 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-12 carbon atoms, substituted or unsubstituted amino groups having 0-12 carbon atoms, and Its combination; Preferably, the R a1 R a2 R a3 R a4 R a5 R a6 R a7 Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, trimethylgermanyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthracene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.
8. The organic electroluminescent device as described in claim 6, wherein, The R a1 R a2 R a3 R a4 R a5 R a6 R a7 At least one of them, each time appearing identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Preferably, the R a1 R a2 R a3 R a4 R a5 R a6 R a7 At least one of them, each time appearing, is selected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 cyclic carbon atoms, substituted or unsubstituted heteroalkyl having 1-6 carbon atoms, substituted or unsubstituted aryl having 6-24 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alksilyl having 3-6 carbon atoms, substituted or unsubstituted arylsilyl having 6-12 carbon atoms, substituted or unsubstituted alkylgermanium having 3-6 carbon atoms, substituted or unsubstituted arylgermanium having 6-12 carbon atoms, substituted or unsubstituted amino having 0-12 carbon atoms, and combinations thereof; More preferably, the R a1 R a2 R a3 R a4 R a5 R a6 R a7 At least one of them, each time appearing, is selected from the group consisting of: deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, trimethylgermanyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, naphthyl, phenanthryl, anthracene, indyl, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.
9. The organic electroluminescent device as claimed in claim 1, wherein, The first compound is selected from the group consisting of the following structures: Optionally, the hydrogen in the above structure can be partially or completely replaced by deuterium.
10. The organic electroluminescent device as claimed in claim 1, wherein, The maximum emission wavelength λ of the photoluminescence spectrum of the first compound max-PL-1 The wavelength range is 450nm to 500nm. Preferably, the maximum emission wavelength λ of the photoluminescence spectrum of the first compound is... max-PL-1 The wavelength range is 450nm to 470nm. More preferably, the maximum emission wavelength λ of the photoluminescence spectrum of the first compound is... max-PL-1 The wavelength range is 455nm to 465nm.
11. The organic electroluminescent device as claimed in claim 1, wherein, The full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound PL-1 Less than or equal to 45nm; Preferably, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 35nm; More preferably, the full width at half maximum (FWHM) of the photoluminescence spectrum of the first compound is... PL-1 Less than or equal to 25nm.
12. The organic electroluminescent device as claimed in claim 1, wherein, In Equation 2, the metal M is selected from the group consisting of Cu, Ag, Au, Zn, Ru, Rh, Pd, Os, Ir and Pt; Preferably, the metal M is selected from Pt or Pd; More preferably, the metal M is selected from Pt.
13. The organic electroluminescent device as claimed in claim 1, wherein, In Formula 2, ring F, ring G, and ring H are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-30 carbon atoms, or heteroaromatic rings having 3-30 carbon atoms; ring I is selected from unsaturated heterocycles having 3-30 carbon atoms each time it appears. Preferably, ring F, ring G, and ring H are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms; ring I is selected from unsaturated heterocycles having 3-18 carbon atoms each time it appears; More preferably, ring F, ring G, and ring H are each independently selected from benzene rings, pyridine rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, dibenzofuran rings, benzothiophene rings, dibenzothiophene rings, dibenzoselenene rings, cyclopentadiene rings, furan rings, thiophene rings, or thiophene rings; and ring I is selected from imidazole carbene rings or benzoimidazole carbene rings each time it appears.
14. The organic electroluminescent device as claimed in claim 1, wherein, In Equation 2, K1-K4 are selected from single bonds.
15. The organic electroluminescent device as claimed in claim 1, wherein, The second compound has a structure represented by one of formulas 3-1 to 3-18: In this case, A4 is selected from single bonds, O, S, Se, (SiR) each time it appears, either the same or different. q R q ) y PR q NR q , substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof; y is selected from 1, 2 or 3 each time it appears, either identically or differently. U1-U 20 Each time it appears, it is selected from CR in the same or different ways. n Or N; R u Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution; R N R q R n and R u Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R N R q R n and R u They can be arbitrarily connected to form a loop; Where R has the structure represented by Equation 2-1: In Formula 2-1, ring M and ring W are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof. X5 and X6 are selected from C or N each time they appear, either the same or different. X7 is selected from CR” or N each time it appears, either the same or different. "*" indicates the connection position of Equation 2-1; R m R w Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution; R m R w The letter "R" is selected, in the same or different manner, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R m R w They can be arbitrarily connected to form a loop; Preferably, the second compound has a structure represented by formula 3-1 or formula 3-2; More preferably, the second compound has a structure represented by Formula 3-2.
16. The organic electroluminescent device as claimed in claim 15, wherein, The A4 is selected from a single bond, O, or S; Preferably, A4 is selected from O.
17. The organic electroluminescent device as claimed in claim 15, wherein, The U1-U 20 Each time it appears, it is selected from CR in the same or different ways. n And the R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and combinations thereof; Preferably, the R n Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazole, indolyl, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.
18. The organic electroluminescent device as claimed in claim 15, wherein, U1-U 20 At least one of them is selected from CR each time it appears, either identically or differently. n ; and the R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. , substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Preferably, U3 is selected from CR n And the R n Choose from the group consisting of: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... The following are substituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms. More preferably, U3 is selected from CR n And the R n Choose from the following groups: n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, partially or fully deuterated n-butyl, partially or fully deuterated isobutyl, partially or fully deuterated tert-butyl, partially or fully deuterated cyclopentyl, partially or fully deuterated cyclohexyl, partially or fully deuterated neopentyl, and combinations thereof.
19. The organic electroluminescent device as claimed in claim 1 or 15, wherein, The R has a structure represented by Equation 2-1-1: In Equation 2-1-1, M1 to M5 are each independently selected from CR. m Or N; W1 to W4 are each independently selected from CR w Or N; R m and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R m R w They can be arbitrarily connected to form a loop; Preferably, R has a structure represented by Equation 2-1-2: In Equation 2-1-2, M1 to M 10 Each independently selected from CR m Or N; W1 to W3 are each independently selected from CR w Or N; R m and R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; More preferably, at least one of W1 to W3 is selected from CR each time it appears, either identically or differently. w And the R w Each time it appears, it is selected from the group consisting of the same or different groups: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted groups having Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms.
20. The organic electroluminescent device as claimed in claim 1, wherein, The second compound has Pt(L) a (L) b The structure is represented by ) where L a and L b These are the first and second ligands that coordinate with Pt, respectively, and the L a Choose freely L a 1-1 to L a 1-25 and L a 2-1 to L a Groups consisting of 2-6, wherein L b Choose freely L b 1-1 to L b 1-8 and L b 2-1 to L b Groups consisting of 2-22: The L a 1-1 to L a 1-25 and L a 2-1 to L a In the structure 2-6, "#" indicates a relationship with L. b The location of the connection; the L b Choose freely L b 1-1 to L b 1-8 and L b 2-1 to L b Groups consisting of 2-22: The L b 1-1 to L b 1-8 and L b 2-1 to L b In the structure 2-22, " "Indicates L" a The location of the connection; Preferably, the second compound is selected from the group consisting of Pt1 to Pt83, wherein Pt1 to Pt83 have Pt(L) a (L) b The structure represented by ) and the L a and the L b These correspond to the structures shown in the table below: Optionally, hydrogen in the Pt1 to Pt83 structures can be partially or completely replaced by deuterium.
21. The organic electroluminescent device as claimed in claim 1, wherein, The organic layer is a light-emitting layer, the first compound is a fluorescent light-emitting material, and the second compound is a phosphorescent photosensitizer; Preferably, the light-emitting layer comprises a first host compound and a second host compound; More preferably, the first and second main compounds are each independently selected from compounds containing at least one of the following chemical groups: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
22. A display device comprising the organic electroluminescent device according to any one of claims 1-21.
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