Organic light-emitting device and display assembly thereof
By using a combination of a second organic material with a specific high triplet energy level and a first organic material with a small energy level difference in organic electroluminescent devices, the problems of reduced efficiency and short lifetime of phosphorescent OLED devices are solved, achieving more efficient charge balance and energy transfer, and improving device performance.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-11-24
- Publication Date
- 2026-04-07
AI Technical Summary
Existing phosphorescent OLED devices exhibit rapid efficiency degradation at high brightness levels, blue color unsaturation, short device lifetime, and challenges in charge balance and energy transfer, all of which affect device performance.
A second organic material with a specific high triplet energy level is used in the second organic layer, and a combination of first and second organic materials with a specific small energy level difference is used in the first organic layer to form a directly contacted organic layer structure, so as to regulate the exciton luminescence characteristics in the luminescent layer.
It significantly improves device efficiency and lifespan at low voltages, resulting in superior overall performance.
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Figure CN121815892A_ABST
Abstract
Description
TECHNICAL FIELD
[0001] The present invention relates to an organic electronic device, such as an organic light emitting device. More in particular, it relates to an organic electroluminescent device comprising a first organic layer and a second organic layer in direct contact with the light emitting layer, and a display assembly. BACKGROUND
[0002] Organic electronic devices include, but are not limited to, the following kinds: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
[0003] In 1987, Tang and Van Slyke at Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). Upon biasing the device, green light emitted from the device. 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 light emitting layers between the cathode and anode. Since OLEDs are self-emissive solid state devices, they offer great potential for display and lighting applications. In addition, the intrinsic properties of organic materials, such as their flexibility, can make them well suited for special applications, such as fabrication on 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] In recent years, simplifying the structure of organic light-emitting diode (OLED) devices to reduce manufacturing costs and improve production efficiency has become a research focus. However, challenges remain in phosphorescent OLED devices regarding device voltage, luminous efficiency, and lifetime. A major challenge in phosphorescent OLED devices is achieving efficient charge balance and energy transfer. Optimizing the hole transport region to balance charge transport and achieve more efficient energy transfer, thereby resulting in superior device performance, is a pressing research topic. Summary of the Invention
[0009] The present invention aims to provide a series of novel organic electroluminescent devices to solve at least some of the aforementioned problems. The novel organic electroluminescent device comprises a first organic layer, a light-emitting layer, and a second organic layer disposed between the two. By using a second organic material with a specific high triplet energy level in the second organic layer, and a combination of a first organic material and a second organic material with a specific small energy level difference in the first organic layer, the novel simplified structure of the organic electroluminescent device of the present invention can effectively control the luminescence characteristics of excitons in the light-emitting layer, achieving significantly improved efficiency or lifetime while maintaining low voltage, and thus obtaining superior overall device performance.
[0010] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0011] anode;
[0012] cathode;
[0013] A light-emitting layer disposed between the anode and the cathode;
[0014] And a first organic layer and a second organic layer disposed between the anode and the light-emitting layer;
[0015] The first organic layer comprises a first organic material and a second organic material, and the second organic layer comprises a second organic material.
[0016] Among them, the LUMO energy level of the first organic material is LUMO 第一有机材料 The HOMO level of the second organic material 第二有机材料 The LUMO 第一有机材料 -HOMO 第二有机材料 <0.418eV
[0017] The triplet energy level of the second organic material is greater than or equal to 2.60 eV;
[0018] The first organic layer is in direct contact with the second organic layer, and the second organic layer is in direct contact with the light-emitting layer.
[0019] According to another embodiment of the present invention, a display component comprising an organic electroluminescent device, the structure of which is shown in the foregoing embodiments.
[0020] The novel organic electroluminescent device disclosed in this invention comprises a first organic layer, a light-emitting layer, and a second organic layer disposed between the two. By using a second organic material with a specific high triplet energy level in the second organic layer and a combination of a first organic material and a second organic material with a specific small energy level difference in the first organic layer, the novel simplified organic electroluminescent device of this invention can effectively control the light emission characteristics of excitons in the light-emitting layer. While maintaining a low voltage, it can achieve significantly improved efficiency or lifetime, and obtain superior overall device performance. Attached Figure Description
[0021] Figure 1 This is a schematic diagram of the bottom-emission organic electroluminescent device disclosed in this paper.
[0022] Figure 2 This is a schematic diagram of a typical top-emitting OLED device 200.
[0023] Figure 3 This is a schematic diagram of a typical stacked OLED device 300. Detailed Implementation
[0024] OLED devices can be fabricated on various substrates, such as glass, plastic, and metal. An OLED device may include an anode layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emissive layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), and a cathode layer. OLED devices 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.
[0025] 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.
[0026] 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.
[0027] 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.
[0028] OLEDs also require an encapsulation layer 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.
[0029] 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.
[0030] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0031] 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.
[0032] 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.
[0033] As used in this article, the term "single-layer device" refers to a device having a single light-emitting layer (or multiple consecutive light-emitting layers) and a single set of hole and electron transport layers between a pair of anodes and cathodes. Such a device with a single light-emitting layer (or multiple consecutive light-emitting layers) and its associated transport layers is called a "single-layer device".
[0034] As used in this article, the term "stacked device" refers to a device structure with multiple light-emitting layers between a pair of anodes and cathodes, each of which has its own independent hole transport layer and electron transport layer. Each light-emitting layer and its associated hole transport layer and electron transport layer constitute a light-emitting unit. These light-emitting units are connected by charge generation layers. A device with multiple light-emitting units is called a "stacked device".
[0035] A schematic diagram of a typical stacked OLED device 300 is shown below. Figure 3As shown, it includes an anode layer 301, a first light-emitting unit 302, a charge-generating layer (CGL) 303, a second light-emitting unit 304, and a cathode layer 305. The first light-emitting unit 302 and the second light-emitting unit 304 may comprise a series of organic layers from a hole injection layer to an electron injection layer; the light-emitting layers of the first light-emitting unit 302 and the second light-emitting unit 304 may be the same or different. The charge-generating layer (CGL) 303 typically comprises an n-type CGL containing an n-type material and a p-type CGL containing a p-type material. A buffer layer may be further added between the n-type CGL and the p-type CGL, as described in patent application CN112687811A. If the stacked device is a top-emitting device, a capping layer (CPL, not shown in the figure) may also be added above the cathode layer 305. Figure 3 The diagram shows a two-unit stacked device. A third light-emitting unit and a second charge-generating layer can be added to form a three-unit stacked device. The fabrication of stacked OLED devices is well-known in the industry and will not be elaborated upon here.
[0036] 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.
[0037] 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).
[0038] 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.
[0039] 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 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).
[0040] Definition of the term "substituent group"
[0041] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0042] 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.
[0043] 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.
[0044] 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.
[0045] 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.
[0046] 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.
[0047] 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.
[0048] Heterocyclic groups or heterocycles – 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. In addition, the heterocyclic group can be optionally substituted.
[0049] 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.
[0050] 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.
[0051] 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.
[0052] 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.
[0053] 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.
[0054] 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.
[0055] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The 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.
[0056] 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.
[0057] 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.
[0058] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. 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 group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.
[0059] 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.
[0060] 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.
[0061] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, 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.
[0062] 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.
[0063] 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:
[0064]
[0065] 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:
[0066]
[0067] 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, as exemplified by the following formula:
[0068]
[0069] 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:
[0070]
[0071] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0072] anode;
[0073] cathode;
[0074] A light-emitting layer disposed between the anode and the cathode;
[0075] And a first organic layer and a second organic layer disposed between the anode and the light-emitting layer;
[0076] The first organic layer comprises a first organic material and a second organic material, and the second organic layer comprises a second organic material.
[0077] Among them, the LUMO energy level of the first organic material is LUMO 第一有机材料 The HOMO level of the second organic material 第二有机材料 The LUMO 第一有机材料 -HOMO 第二有机材料 <0.418eV
[0078] The triplet energy level of the second organic material is greater than or equal to 2.60 eV;
[0079] The first organic layer is in direct contact with the second organic layer, and the second organic layer is in direct contact with the light-emitting layer.
[0080] According to one embodiment of the present invention, the light-emitting layer includes a light-emitting dopant material, the light-emitting dopant material is a blue phosphorescent light-emitting dopant material, and the maximum emission wavelength of the blue phosphorescent light-emitting dopant material is 430nm to 480nm.
[0081] According to one embodiment of the present invention, the maximum emission wavelength of the blue phosphorescent doped material is 450 nm to 470 nm.
[0082] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.410eV.
[0083] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.400eV.
[0084] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.390eV.
[0085] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.380eV.
[0086] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥-2.0eV.
[0087] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥-1.5eV.
[0088] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥-1.0eV.
[0089] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥0eV.
[0090] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥0.1eV.
[0091] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 -HOMO 第二有机材料 ≥0.2eV.
[0092] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 ≤-5.150eV.
[0093] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 ≤-5.200eV.
[0094] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 ≥-7.0eV.
[0095] According to one embodiment of the present invention, wherein the LUMO 第一有机材料 ≥-6.0eV.
[0096] According to an embodiment of the present invention, the first organic material has a structure represented by Formula 1:
[0097]
[0098] In Equation 1,
[0099] W1 and W2 are selected from NR each time they appear, either in the same or different ways. N1 CR C1 R C2 , O, S or Se;
[0100] V1 and V2 are selected from O, S or Se each time they appear, either the same or different.
[0101] R1, R2, R N1 R C1 and R C2 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoyl, azirane, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with 1-20 carbon atoms. Alkoxy groups with 6 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alksilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, and combinations thereof;
[0102] R1, R2, R N1 R C1 and R C2 At least one of them is a group having at least one electron-withdrawing group;
[0103] In Formula 1, adjacent substituents R1, R2, R N1 R C1 and R C2 They can be arbitrarily connected to form a ring.
[0104] In this paper, adjacent substituents R1, R2, R N1 R C1 and R C2 They can be optionally linked to form a ring, intended to represent any adjacent set of substituents, such as adjacent substituents R1 and R2. N1 Adjacent substituents R2 and R N1 Adjacent substituent RC1 and R C2 Any one or more of these adjacent substituent groups can connect to form a ring. Obviously, any adjacent substituent groups may also not connect to form a ring.
[0105] According to one embodiment of the present invention, the Hammett constant of the electron-withdrawing group is greater than or equal to 0.05, preferably greater than or equal to 0.3, and more preferably greater than or equal to 0.5.
[0106] The electron-withdrawing group of the present invention has a Hammett constant greater than or equal to 0.05, and has a strong electron-withdrawing ability. It should be noted that the Hammett constant includes the Hammett para constant and / or the Hammett meta constant. As long as either the para constant or the meta constant is greater than or equal to 0.05, it can be used as the preferred electron-withdrawing group of the present invention.
[0107] According to one embodiment of the invention, the electron-withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, having Alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 cyclic carbon atoms, heteroalkyl groups having 1-20 carbon atoms, aralkyl groups having 7-30 carbon atoms, alkoxy groups having 1-20 carbon atoms, aryloxy groups having 6-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alksilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and combinations thereof.
[0108] According to one embodiment of the present invention, the electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazine, and combinations thereof.
[0109] According to one embodiment of the present invention, W1 and W2, each time they appear, are selected from the group consisting of the following structures, either identically or differently:
[0110]
[0111] The asterisk (*) indicates the position where the W1 and W2 groups are connected to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring, or dehydrobenzodiselenazole ring in Formula 1.
[0112] According to one embodiment of the present invention, W1 and W2 are
[0113] According to one embodiment of the invention, R1 and R2, each time appearing, are selected from the group consisting of: hydrogen, deuterium, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, and unsubstituted aromatic having 6-30 carbon atoms. The group consisting of an unsubstituted heteroaryl group having 3-30 carbon atoms, and any one of the following groups substituted by one or more of the following groups: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 cyclic carbon atoms, alkoxy having 1-20 carbon atoms, alkenyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof.
[0114] According to one embodiment of the invention, R1 and R2, each time appearing, are selected from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, vinyl groups substituted with one or more of CN or CF3, and vinyl groups substituted with CN. Or one of the substituted ethynyl, dimethylphosphoxy, diphenylphosphoxy, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted by one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazine, diphenylborane, oxaboxanthracene, and combinations thereof.
[0115] According to one embodiment of the present invention, R1 and R2 are selected from the group consisting of the following structures each time they appear, either identically or differently:
[0116]
[0117]
[0118]
[0119] in, The R1 and R2 groups indicate the positions where they are attached to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring, or dehydrobenzodiselenazole ring in Formula 1.
[0120] According to one embodiment of the present invention, R1 and R2 are the same.
[0121] According to one embodiment of the present invention, the first organic material is selected from the group consisting of compounds 1 to 182; said compounds 1 to 182 have a structure represented by formula 1-1:
[0122]
[0123] Wherein, the two V structures in Formula 1-1 are identical, and the V, W1, W2, R1, and R2 are respectively selected from the atoms or groups shown in the table below;
[0124]
[0125]
[0126]
[0127] According to one embodiment of the present invention, the concentration of the first organic material in the first organic layer is ≥5%.
[0128] In this embodiment, the concentration of the first organic material refers to the percentage of the weight of the first organic material in the first organic layer relative to the total weight of the first organic layer.
[0129] According to one embodiment of the present invention, the concentration of the first organic material in the first organic layer is ≥10%.
[0130] According to one embodiment of the present invention, the triplet energy level of the second organic material is greater than or equal to 2.70 eV.
[0131] According to one embodiment of the present invention, the triplet energy level of the second organic material is greater than or equal to 2.80 eV.
[0132] According to one embodiment of the present invention, the triplet energy level of the second organic material is less than or equal to 3.10 eV.
[0133] According to one embodiment of the present invention, the triplet energy level of the second organic material is less than or equal to 3.00 eV.
[0134] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 ≤-5.100eV.
[0135] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 ≤-5.200eV.
[0136] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 ≤-5.300eV.
[0137] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 ≤-5.400eV.
[0138] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 ≤-5.450eV.
[0139] According to one embodiment of the present invention, the light-emitting layer further includes a host material, the host material having a triplet energy level greater than or equal to 2.60 eV, and the host material being the same as or different from the second organic material.
[0140] According to one embodiment of the present invention, the light-emitting layer further includes a host material, wherein the triplet energy level of the host material is less than or equal to 3.10 eV.
[0141] According to one embodiment of the present invention, the light-emitting layer further includes a host material, which is the same as the second organic material.
[0142] According to one embodiment of the present invention, in the organic electroluminescent device, the first organic layer, the second organic layer and the light-emitting layer all contain the same second organic material.
[0143] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 Greater than or equal to -7.0 eV.
[0144] According to one embodiment of the present invention, wherein the HOMO 第二有机材料 Greater than or equal to -6.0 eV.
[0145] According to one embodiment of the present invention, the second organic material has a structure represented by Formula 2:
[0146]
[0147] In Equation 2,
[0148] a and c are each independently selected from 0, 1, 2, 3, 4 or 5;
[0149] m is selected from 1, 2, 3, 4, or 5;
[0150] b and d are each independently selected from 0, 1, 2 or 3, and b + d is greater than or equal to 1;
[0151] X is selected from C, CR each time it appears, either identically or differently. x Or N;
[0152] Z is selected from CR each time it appears, either the same or different. x Or N;
[0153] A is selected from C, CR each time it appears, either identically or differently. x Or N;
[0154] K is selected from CR each time it appears, either the same or different. x Or N;
[0155] Y is selected from C, CR each time it appears, either identically or differently. y Or N;
[0156] The R x and R y 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;
[0157] Adjacent substituent R x and R y They can be arbitrarily connected to form a ring.
[0158] In this embodiment, when a is 0 and b is 1, 2, or 3 in Equation 2, it indicates that the carbazole ring or azacarbazole ring containing X in Equation 2 does not exist. In this case, the carbazole ring or azacarbazole ring containing Z in Equation 2 will be directly connected to the ring containing Y. That is, the structure of Equation 2 is as follows: Similarly, when c is 0 and d is 1, 2, or 3, it indicates that the carbazole ring or azacarbazole ring containing A in Equation 2 does not exist. In this case, the carbazole ring or azacarbazole ring containing K in Equation 2 will be directly connected to the ring containing Y, that is, the structure of Equation 2 is as follows: For example, when a and c are 0, and b and d are 1, the structure of equation 2 is as follows:
[0159] In this paper, adjacent substituents R x and R y They can be optionally linked to form a ring, intended to represent any adjacent set of substituents, such as two adjacent substituents R. x Two adjacent substituents R y Adjacent substituent R x and R y Any one or more of these adjacent substituent groups can connect to form a ring. Obviously, these any adjacent substituent groups can also remain unconnected to form a ring.
[0160] According to one embodiment of the present invention, in Equation 2, b and d are each independently selected from 0 or 1, and b+d is greater than or equal to 1.
[0161] According to one embodiment of the present invention, in Equation 2, b is 1 and d is 0 or 1.
[0162] According to one embodiment of the present invention, in Formula 2, a and c are each independently selected from 0, 1 or 2.
[0163] According to one embodiment of the present invention, in Formula 2, a and c are each independently selected from 0 or 1.
[0164] According to one embodiment of the present invention, in Equation 2, a+b is greater than or equal to 2.
[0165] According to one embodiment of the present invention, in Formula 2, m is selected from 1, 2 or 3.
[0166] According to one embodiment of the present invention, in Formula 2, m is selected from 1 or 2.
[0167] According to one embodiment of the present invention, in Formula 2, X is selected from C or CR each time it appears, either identically or differently. x Z is selected from CR each time it appears, either the same or different. x A is selected from C or CR each time it appears, either identically or differently.x K is selected from CR each time it appears, either the same or different. x And the R x 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 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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.
[0168] According to one embodiment of the present invention, in Formula 2, X is selected from C or CR each time it appears, either identically or differently. x Z is selected from CR each time it appears, either the same or different. x A is selected from C or CR each time it appears, either identically or differently. x K is selected from CR each time it appears, either the same or different. x The R x Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and combinations thereof.
[0169] According to one embodiment of the present invention, in Formula 2, X is selected from C or CR each time it appears, either identically or differently. x Z is selected from CR each time it appears, either the same or different. x A is selected from C or CR each time it appears, either identically or differently. x K is selected from CR each time it appears, either the same or different. x The R x Each time it appears, it is selected from the group consisting of the following groups, either the same or different: hydrogen, deuterium, fluorine, cyano, indolyl, carbazole, triazine, and combinations thereof.
[0170] According to one embodiment of the present invention, in Formula 2, Y is selected from C or CR each time it appears, either the same or different. y The R y 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.
[0171] According to one embodiment of the present invention, in Formula 2, Y is selected from C or CR each time it appears, either the same or different. y The R y Each time it appears, it is selected from the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, and combinations thereof.
[0172] According to one embodiment of the present invention, in Formula 2, Y is selected from C or CR each time it appears, either the same or different. y The R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indene, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, triazine, and combinations thereof.
[0173] According to one embodiment of the present invention, the second organic material is selected from the group consisting of compounds HT1-1 to HT1-13, compounds HT2-1 to HT2-21, compounds HT3-1 to HT3-21, and compounds HT4-1 to HT4-18.
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181] According to one embodiment of the present invention, the luminescent doped material is a metal complex and has a structure represented by Formula 3:
[0182]
[0183] In Equation 3, metal M is selected from metals with a relative atomic mass greater than 40;
[0184] Ring F, ring G, ring H and ring I are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 1 to 30 carbon atoms, or combinations thereof;
[0185] e is selected from 0 or 1;
[0186] A1-A4 are selected from single bonds, O, S, Se, (SiR”R”) each time they appear, either identically or differently. y ,PR”,NR”,(CR”R”) 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;
[0187] Z1-Z4 are selected from C or N each time they appear, either identically or differently;
[0188] K1-K4 are selected from single bonds, O or S, each time they appear, either the same or different.
[0189] R n Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0190] R”, 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;
[0191] Adjacent substituents R”, R n Substituents can be optionally linked to form rings.
[0192] According to one embodiment of the present invention, at least one of rings F, G, H and I comprises an imidazole ring or an imidazole carbene ring.
[0193] According to one embodiment of the present invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
[0194] According to one embodiment of the present invention, in Equation 3, e is 0, and M is selected from Pt or Pd.
[0195] According to one embodiment of the present invention, the luminescent doped material has a structure represented by one of Formulas 4-1 to 4-20:
[0196]
[0197]
[0198]
[0199] in,
[0200] A4 is selected from single bonds, O, S, Se, (SiR”R”) each time it appears, either identically or differently. y , PR, NR, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl 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.
[0201] U1-U 20 Each time it appears, it is selected from CR in the same or different ways. n Or N;
[0202] R u Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0203] R, R', R”, R u and R nEach 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;
[0204] Adjacent substituents R, R', R", R u and R n They can be arbitrarily connected to form a ring.
[0205] In this paper, adjacent substituents R, R', R'', R'' are... u and R n They can be optionally linked to form a ring, intended to represent any adjacent set of substituents, such as adjacent substituents R and R'. u Adjacent substituents R' and R n "Two adjacent substituents R", "two adjacent substituents R" n Adjacent substituents R and R n Adjacent substituents R” and R n Any one or more of these adjacent substituent groups can connect to form a ring. Obviously, these any adjacent substituent groups can also remain unconnected to form a ring.
[0206] According to one embodiment of the present invention, the luminescent doped material has a structure represented by Formula 4-1 or Formula 4-2.
[0207] 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 nEach 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.
[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 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.
[0209] According to one embodiment of the present invention, wherein, in formulas 4-1 to 4-20, the substituent R has a structure represented by formula 5:
[0210]
[0211] In Formula 5, rings T, M, and W are selected, either identically or differently, from unsaturated carbon rings having 5-30 carbon atoms, unsaturated heterocycles having 3-30 carbon atoms, or combinations thereof.
[0212] Z5-Z8 are selected from C or N each time they appear, either identically or differently;
[0213] "*" indicates the connection position of Equation 5;
[0214] R t R m Each occurrence being the same or different indicates monosubstitution, polysubstitution, or no substitution;
[0215] R w Each occurrence, whether identical or different, is represented by single substitution or multiple substitution;
[0216] R t R m and R wEach 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;
[0217] There is at least one R on the ring W in Equation 5. 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;
[0218] Adjacent substituent R t R m R w They can be arbitrarily connected to form a ring.
[0219] In this paper, adjacent substituents R t R m R w They can be optionally linked to form a ring, intended to represent any adjacent set of substituents, such as adjacent substituents R. t and R w Adjacent substituent R w and R m Two adjacent substituents R t Two adjacent substituents R m and the two adjacent substituents R w Any one or more of these adjacent substituent groups can connect to form a ring. Obviously, these any adjacent substituent groups can also remain unconnected to form a ring.
[0220] According to one embodiment of the present invention, the luminescent doped material has Pt(L) a (L) b The structure represented by ) is L a and L b These are the first and second ligands that coordinate with metallic Pt, respectively, and the L a Choose from the following groups:
[0221]
[0222]
[0223]
[0224] The L a The "#" in the structure indicates that the structure is related to L. b The location of the connection;
[0225] The L b Choose from the following groups:
[0226]
[0227]
[0228] The L b In the structure Indicates with L a The position of the "#" in the text;
[0229] In the structure, "t-Bu" represents tert-butyl, "i-Pr" represents isopropyl, and "Ph" represents phenyl.
[0230] According to one embodiment of the present invention, the luminescent doping material is selected from the group consisting of compounds Pt1 to Pt83; the compounds 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:
[0231]
[0232]
[0233] According to one embodiment of the present invention, the light-emitting layer comprises a second host material.
[0234] According to one embodiment of the present invention, the second body material has a structure represented by any one of Formulas 6 to 8:
[0235]
[0236] In Equation 6, Z 11 To Z 13 Each time it appears, it is selected from CR in the same or different ways. 14 Or N, and Z 11 To Z 13 At least one of them is N;
[0237] 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.
[0238] In equation 7 or equation 8, Z 14 Each time it appears, it is selected from CR in the same or different ways. 14 Or N, and at least one Z 14 Let N be the number of people in the group.
[0239] Z 15 Each time it appears, it is selected from O or S, either the same or different.
[0240] R 11 -R 14Each 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;
[0241] Adjacent substituent R 14 They can be arbitrarily connected to form a ring.
[0242] According to one embodiment of the present invention, in Equation 6, Z 11 To Z 13 At least two of them are N.
[0243] According to one embodiment of the present invention, in Equation 6, Z 11 To Z 13 All are N.
[0244] According to one embodiment of the invention, in Formula 6, L is selected from the group consisting of the same or different groups of the following 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.
[0245] According to one embodiment of the present invention, in Formula 6, L is selected from the group consisting of the same or different groups of the following each time it appears: single bond, phenylene, biphenylene, fluorene, triphenylene, furanyl, thiophene, dibenzofuranyl, dibenzothiophene, and combinations thereof.
[0246] According to one embodiment of the present invention, wherein R 11 To R 14Each 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 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.
[0247] According to one embodiment of the present invention, wherein R 11 To R 14 Each time it appears, it is selected from the same or different groups of the following: 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.
[0248] According to one embodiment of the present invention, wherein R 11 To R 14 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, triazine, triphenylsilyl, and combinations thereof.
[0249] According to one embodiment of the present invention, the second host material is selected from compounds N-1-1 to N-1-60.
[0250] The group consisting of compounds N-2-1 to N-2-35:
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258] According to one embodiment of the present invention, the hydrogen in the structure of compounds N-1-1 to N-1-53, N-1-58, N-2-1 to N-2-32, and N-2-36 to N-2-39 can be partially or completely replaced by deuterium.
[0259] According to one embodiment of the present invention, the first organic layer is in direct contact with the anode.
[0260] According to one embodiment of the present invention, the organic electroluminescent device is a top-emitting device.
[0261] A typical top-emitting OLED device 200 structure diagram is shown below. Figure 2 As shown, the figures are not necessarily drawn to scale. The OLED device 200 includes an anode layer 201, a hole injection layer (HIL) 202, a hole transport layer (HTL) 203, an electron blocking layer (EBL) 204, a light-emitting layer (EML) 205, a hole blocking layer (HBL) 206, an electron transport layer (ETL) 207, an electron injection layer (EIL) 208, a cathode layer 209, and a capping layer (CPL) 210. The anode layer 201 is a material or combination of materials with high reflectivity, including but not limited to Ag, Ti, Cr, Pt, Ni, TiN, and combinations of the above materials with ITO and / or MoOx (molybdenum oxide), typically with a reflectivity greater than 50%; preferably, with a reflectivity greater than 80%; more preferably, with a reflectivity greater than 90%. The cathode layer 209 should be a translucent or transparent conductive material, including but not limited to MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or combinations thereof, with a transparency generally greater than 30%; preferably, the transparency is greater than 50%. The hole injection layer 202 can be a single material layer, such as the commonly used HATCN; the hole injection layer 202 can also be a hole transport material doped with a certain proportion of p-type conductive dopant, usually with a doping ratio not exceeding 5%, commonly between 1% and 3%. The light-emitting layer 205 typically also includes at least one host material and at least one light-emitting material. The electron transport layer 207 can be a single layer of Yb, LiQ, or LiF, or it can be formed by co-evaporation of two or more materials. The organic electroluminescent device of the present invention can be a simplified top-emitting device, i.e., without the electron blocking layer 204.
[0262] According to one embodiment of the present invention, the organic electroluminescent device is a single-layer device or a multilayer device.
[0263] According to one embodiment of the present invention, the organic electroluminescent device is a stacked device and includes a first light-emitting unit and a second light-emitting unit, and a charge-generating layer disposed between the first light-emitting unit and the second light-emitting unit; the charge-generating layer includes an n-type charge-generating layer and a p-type charge-generating layer; the second light-emitting unit is disposed on the first light-emitting unit and includes the first organic layer and the second organic layer, and the first organic layer is in direct contact with the p-type charge-generating layer. According to one embodiment of the present invention, a display component is also disclosed, which includes an organic electroluminescent device, the specific structure of which is shown in any of the foregoing embodiments.
[0264] In this invention, a Prism F98 fluorescence spectrophotometer manufactured by Shanghai Prism Technology Co., Ltd. was used to measure the photoluminescence (PL) spectrum data of the phosphorescent doped material. The test material was prepared with HPLC-grade toluene to a concentration of 1×10⁻⁶. -5 A mol / L solution was prepared by purging nitrogen gas to remove oxygen for 5 minutes, and then excited with light at a wavelength of 350 nm at room temperature (298 K) and its emission spectrum was measured. Compound Pt27 was found to have a maximum PL emission wavelength of 460 nm using this method, indicating it is a blue phosphorescent material.
[0265] The electrochemical properties of the compounds used in this invention (e.g., the LUMO energy level of the first organic material and the HOMO energy level of the second organic material) were all determined by cyclic voltammetry (CV). The tests were conducted using a CorrTest CS120 electrochemical workstation manufactured by Wuhan CorrTest Instruments Co., Ltd., employing a three-electrode system: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. Anhydrous DCM was used as the solvent, and 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte to prepare 10... -3 For the mol / L solution, nitrogen gas was bubbled into the solution for 10 min to remove oxygen before the test. Instrument parameter settings: scan rate 100 mV / s, potential interval 0.5 mV, test window -1 V to 1 V.
[0266] In this paper, the triplet energy level (T1) is determined at ultra-low temperatures using the long-lived properties of triplet excitons. Specifically, the test compound is dissolved in 2-methyltetrahydrofuran solvent to prepare 10 -5 A solution of concentration M was prepared, placed in a quartz tube, then placed in a Dewar flask and cooled to 77K. The solution of the analyte was then irradiated with a 350nm light source to measure the phosphorescence spectrum. The spectra were measured using a spectrophotometer, model F98, manufactured by Shanghai Lingguang Technology Co., Ltd.
[0267] The vertical axis of the phosphorescence spectrum represents phosphorescence intensity, and the horizontal axis represents wavelength. After taking the minimum value λ1 (nm) of the peak on the shorter wavelength side of the phosphorescence spectrum, this wavelength value is substituted into the following conversion formula F1 to calculate the triplet energy level of the compound to be tested.
[0268] Conversion formula F1: T1(eV)=1240 / λ1
[0269] Table 1 shows the HOMO energy level data and triplet (T1) energy level data of some compounds determined by the above method, as well as the LUMO energy level data of some compounds.
[0270] Table 1 Energy level data for some compounds
[0271]
[0272] As shown in Table 1, the T1 energy levels of compounds HT-A and HT-B are both less than 2.6 eV, indicating that their T1 energy levels are low, lower than those of the phosphorescent host material. Therefore, when using compounds HT-A or HT-B as the EBL or the HTL in direct contact with the EML, it will be difficult to effectively block excitons from entering the hole transport region. This will significantly reduce the probability of exciton recombination and luminescence in the emissive layer, leading to low device efficiency. On the other hand, compounds HT2-8 and HT1-4 have T1 energy levels greater than 2.6 eV, exhibiting higher T1 energy levels. Thus, when using compounds HT-A or HT-B as the hole transport layer (HTL, the second organic layer), it is not necessary to set up an additional electron blocking layer (i.e., the HTL is in direct contact with the EML), which can effectively control exciton recombination and luminescence within the emissive layer, thereby ensuring high device efficiency.
[0273] It is also worth noting that both HT2-8 and HT1-4 possess relatively deep HOMO levels (HOMO). HTM Ensuring good hole injection capability in the hole injection layer (HIL, the first organic layer) when simultaneously using it is a significant challenge. For the commercially available p-type doped compound PD-A, its LUMO level (LUMO...) PD Although it is already quite deep, the difference between the HOMO level and the HOMO level of HT2-8 and HT1-4 is still large, and the LUMO level is relatively low. PD -HOMO HTM The Δ value is greater than or equal to 0.42 eV, therefore, it is difficult to guarantee good hole injection capability when PD-A is doped into compound HT-A or compound HT-B as a hole injection layer (first organic layer). Compounds 70, 73, and 72 all have deeper LUMO energy levels and stronger oxidation capabilities, with a maximum energy level difference Δ of only 0.404 eV (less than 0.418 eV) compared to HT2-8 and HT1-4. They can be well doped, thus exhibiting excellent hole injection capability, and therefore can yield organic electroluminescent devices with excellent performance in terms of voltage, efficiency, and / or lifetime. The following device examples further verify the excellent performance of the organic electroluminescent device of the present invention.
[0274] 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.
[0275] Example 1: Fabrication of an organic electroluminescent device 100, such as Figure 1 As shown.
[0276] First, a 0.7mm thick glass substrate is used, on which a pre-patterned design is applied. A thick indium tin oxide (ITO) substrate was used as the anode 101. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and ultraviolet ozone. Subsequently, the substrate was dried in a glove box to remove moisture and then placed on a support and transferred to a vacuum chamber. The organic layer specified below was applied at a vacuum degree of approximately 1 × 10⁻⁶. -6 In the case of Torr, The deposition rate was achieved sequentially on the anode via vacuum thermal evaporation: first, compounds HT2-8 and 73 were simultaneously deposited as a hole injection layer (HIL, weight ratio 90:10). )102, vapor-deposited compound HT2-8 is used as a hole transport layer (HTL, )103, then simultaneously deposited compounds HT2-8, N-2-39, and Pt27 as luminescent layers (EML, weight ratio 52.8:35.2:12), )105, vapor-deposited compound N-2-39 as a hole blocking layer (HBL, )106, compounds ET and Liq were co-deposited as an electron transport layer (ETL, weight ratio 40:60, 107, vapor deposition A thick layer of LiF was used as the electron injection layer (EIL) 108. Finally, metallic aluminum was deposited as the cathode. )109. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.
[0277] Example 2:
[0278] The preparation method of Example 2 is the same as that of Example 1, except that compound 72 is used instead of compound 73 in HIL.
[0279] Example 3:
[0280] The preparation method of Example 3 is the same as that of Example 1, except that compound 70 is used instead of compound 73 in HIL.
[0281] Example 4:
[0282] The preparation method of Example 4 is the same as that of Example 1, except that compounds HT1-4 and 73 are simultaneously vapor-deposited as hole injection layers (HIL, weight ratio 90:10). )102, and vapor-deposited compound HT1-4 as a hole transport layer (HTL, )103.
[0283] Example 5:
[0284] The preparation method of Example 5 is the same as that of Example 4, except that compound 72 is used instead of compound 73 in HIL.
[0285] Comparative Example 1:
[0286] The preparation method of Comparative Example 1 was the same as that of Example 1, except that compound PD-A was used instead of compound 73 in HIL.
[0287] Comparative Example 2:
[0288] The preparation method of Comparative Example 2 is the same as that of Example 4, except that compound PD-A is used instead of compound 73 in HIL.
[0289] Comparative Example 3:
[0290] Comparative Example 3 was prepared using the same method as Example 1, except that compounds HT-B and 73 were simultaneously vapor-deposited as a hole injection layer (HIL, weight ratio 90:10). )102, and vapor-deposited compound HT-B as a hole transport layer (HTL, )103.
[0291] Comparative Example 4:
[0292] Comparative Example 4 was prepared using the same method as Example 1, except that compounds HT-A and 73 were simultaneously vapor-deposited as hole injection layers (HIL, weight ratio 90:10). )102, and vapor-deposited compound HT-A as a hole transport layer (HTL, )103.
[0293] Comparative Example 5:
[0294] The preparation method of Comparative Example 5 was the same as that of Comparative Example 4, except that compound 70 was used instead of compound 73 in HIL.
[0295] The detailed structure and thickness of the organic layers in the device are shown in Table 2. The layers use more than one material and are obtained by doping different compounds in the stated weight ratios.
[0296] Table 2. Device structures of partial organic layers in Examples 1-5 and Comparative Examples 1-5.
[0297]
[0298] The material structure used in the device is as follows:
[0299]
[0300]
[0301] Table 3 summarizes the HOMO levels (HOMO) of the hole transport materials used in Examples 1-5 and Comparative Examples 1-5. HTM ), LUMO level of p-type conductive doped material (LUMO PD And the energy level difference between the two, LUMO PD -HOMO HTM (Δ) data, and device performance. Among these, the maximum emission wavelength (λ) max The voltage, power efficiency (PE), and external quantum efficiency (EQE) are all measured at a current density of 10 mA / cm². 2 The device lifetime (LT95) was measured to be 80 mA / cm. 2 The time it takes for the device brightness to decay to 95% of the initial brightness under the current density drive is used for comparison. For a more intuitive comparison, the LT95 of Comparative Example 3 is set to 100%. The LT95 data of Examples 1-5 and Comparative Examples 1-2 and 4-5 are all converted relative to Comparative Example 3.
[0302] Table 3. Energy level data and device performance of some materials in Examples 1-5 and Comparative Examples 1-5.
[0303]
[0304] discuss:
[0305] As can be seen from the data in Table 3, the maximum emission wavelength of Examples 1-5 and Comparative Examples 1-5 is 461 nm, which belongs to blue phosphorescent devices.
[0306] In the HIL of Comparative Example 1, because the LUMO level (-5.037 eV) of the PD-A is relatively shallow, the energy level difference between its LUMO level and the HOMO level of HT2-8 is large (Δ = 0.539 eV). Therefore, although a commercially available PD-A was used in the HIL, the hole injection efficiency of Comparative Example 1 was still low. Thus, although it achieved a very high EQE, its voltage was also very high, which seriously affected the device's lifespan and had no practical value. In contrast, the HIL of Example 1 used a device with a deeper LUMO level (LUMO... 第一有机材料 The first organic material compound 73 (with a voltage of -5.276 eV) is used as a p-type conductive dopant (PD) and is doped in a substrate with a deep HOMO energy level (HOMO). 第二有机材料 In the hole transport material HT2-8 (with a voltage of -5.576 eV), the energy level difference between the two is small (Δ = LUMO). PD -HOMO HTM =LUMO 第一有机材料 -HOMO 第二有机材料 =0.300eV), which can very effectively promote hole injection. Therefore, Example 1 has superior performance compared to Comparative Example 1: its voltage is significantly reduced by 2.7V; its power efficiency is significantly improved by 46%; although the EQE is lower than that of Comparative Example 1, it still achieves an extremely high EQE level of 19.3%; and most importantly, its lifetime LT95 is significantly improved by 85%. Data comparison shows that, due to the use of a high-T1 second organic material in the second organic layer (HTL), and the use of a first organic material (PD) and a second organic material (HTM) that meet a specific energy level difference in the first organic layer (HIL), the organic electroluminescent device of the present invention achieves lower voltage, very high efficiency, and significantly improved device lifetime, achieving superior overall device performance.
[0307] In Examples 2 and 3, first organic material compounds 72 and 70, which are different but both satisfy the LUMO energy level requirement and have a small energy level difference Δ with compound HT2-8 (Δ being 0.348 eV and 0.404 eV, respectively), were used. Compared with Comparative Example 1, the voltages of Examples 2 and 3 were reduced by 2.4 V and 2.0 V, respectively; the power efficiency was significantly improved by 39% and 26%, respectively; and more importantly, the lifetime LT95 was significantly improved by 89% and 96%, respectively. This again demonstrates the significant advantages of the organic electroluminescent device of the present invention due to the selection of first and second organic materials that meet specific conditions, enabling better overall device performance.
[0308] Similarly, in Examples 4 and 5, different first organic material compounds 73 and 72 (Δ = 0.181 eV and 0.229 eV, respectively) were used, but both LUMO levels met the requirements and had a small energy level difference Δ with compound HT2-8. Compared to Comparative Example 2, the voltages of Examples 4 and 5 were significantly reduced by 1.1 V and 1.0 V, respectively; the power efficiency was significantly improved by 19% and 20%, respectively; and the lifetime LT95 was significantly improved by 18% and 22%, respectively. This again demonstrates the significant advantages of the organic electroluminescent device of the present invention due to the selection of first and second organic materials that meet specific conditions, and enables better overall device performance.
[0309] In Comparative Examples 3 and 4, compounds HT-A and HT-B were used in the HIL and the HTL in direct contact with the EML. Although a small energy level difference Δ between them and compound 73 resulted in good hole injection, leading to very low device voltage and long device lifetime, the low triplet energy levels of compounds HT-A and HT-B prevented effective exciton blocking, making it difficult to achieve high device efficiency. In contrast, Examples 1 and 4 used second organic materials HT2-8 and HT1-4 with specific high triplet energy levels in the first and second organic layers, which effectively blocked excitons. The device efficiency of Examples 1 and 4 was significantly improved compared to Comparative Examples 3 and 4: while the PE maintained the high level of Comparative Examples 3 and 4 or even improved significantly, the EQE was significantly improved, with an increase of 5.2% to 9.6%. Furthermore, because the first and second organic materials used in the first organic layer had a specific small energy level difference, Examples 1 and 4 also maintained a low voltage level and long device lifetime that were basically equivalent to Comparative Examples 3 and 4, achieving superior overall device performance. Similarly, although the voltage of Example 3 was higher and the PE was lower than that of Comparative Example 5, it was still at the low voltage and high PE level. More importantly, the EQE of Example 3 was significantly improved by 11.3% compared to Comparative Example 5, and the lifetime was significantly improved by 5.8%, thus achieving better overall device performance.
[0310] In summary, the organic electroluminescent device disclosed in this invention uses a combination of a first organic material and a second organic material with a specific energy level difference. At the same time, the second organic material has a high triplet energy level, which allows for effective control of the exciton luminescence characteristics in the light-emitting layer without setting an EBL. While maintaining a low voltage, it can achieve significantly improved efficiency or lifetime, resulting in superior overall device performance.
[0311] 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; A light-emitting layer disposed between the anode and the cathode; And a first organic layer and a second organic layer disposed between the anode and the light-emitting layer; The first organic layer comprises a first organic material and a second organic material, and the second organic layer comprises a second organic material. Among them, the LUMO energy level of the first organic material is LUMO 第一有机材料 The HOMO energy level of the second organic material is HOMO 第二有机材料 The LUMO 第一有机材料 -HOMO 第二有机材料 <0.418eV The triplet energy level of the second organic material is greater than or equal to 2.60 eV; The first organic layer is in direct contact with the second organic layer, and the second organic layer is in direct contact with the light-emitting layer.
2. The organic electroluminescent device as described in claim 1, wherein, The light-emitting layer includes a light-emitting dopant material, which is a blue phosphorescent dopant material, and the maximum PL emission wavelength of the blue phosphorescent dopant material is 430nm to 480nm. Preferably, the maximum emission wavelength of the blue phosphorescent doped material is 450 nm to 470 nm.
3. The organic electroluminescent device as described in claim 1, wherein, The LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.410eV; preferably, the LUMO 第一有机材料 -HOMO 第二有机材料 ≤0.400eV.
4. The organic electroluminescent device as described in claim 1, wherein, The LUMO 第一有机材料 ≤-5.150eV; preferably, the LUMO 第一有机材料 ≤-5.200eV.
5. The organic electroluminescent device as described in claim 1, wherein, The first organic material has a structure represented by Formula 1: In Equation 1, W1 and W2 are selected from NR each time they appear, either identically or differently. N1 CR C1 R C2 , O, S or Se; V1 and V2 are selected from O, S or Se each time they appear, either the same or different. R1, R2, R N1 R C1 and R C2 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoyl, azirane, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with 1-20 carbon atoms. Alkoxy groups with 6 to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alksilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6 to 20 carbon atoms, and combinations thereof; R1, R2, R N1 R C1 and R C2 At least one of them is a group having at least one electron-withdrawing group; In Formula 1, adjacent substituents R1, R2, R N1 R C1 and R C2 They can be arbitrarily connected to form a ring.
6. The organic electroluminescent device as claimed in claim 1, wherein the concentration of the first organic material in the first organic layer is ≥5%, preferably, the concentration of the first organic material in the first organic layer is ≥10%.
7. The organic electroluminescent device as described in claim 1, wherein, The triplet energy level of the second organic material is greater than or equal to 2.70 eV, preferably greater than or equal to 2.80 eV.
8. The organic electroluminescent device as described in claim 1, wherein, The HOMO 第二有机材料 ≤-5.400eV, preferably, the HOMO 第二有机材料 ≤-5.450eV.
9. The organic electroluminescent device as claimed in claim 1, wherein, The second organic material has a structure represented by Formula 2: In Equation 2, a and c are each independently selected from 0, 1, 2, 3, 4 or 5; m is selected from 1, 2, 3, 4, or 5; b and d are each independently selected from 0, 1, 2 or 3, and b + d is greater than or equal to 1; X is selected from C, CR each time it appears, either identically or differently. x Or N; Z is selected from CR each time it appears, either identically or differently. x Or N; A is selected from C, CR each time it appears, either identically or differently. x Or N; K is selected from CR each time it appears, either the same or different. x Or N; Y is selected from C, CR each time it appears, either identically or differently. y Or N; The R x and R y 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 x and R y They can be arbitrarily connected to form a ring.
10. The organic electroluminescent device as described in claim 2, wherein, The luminescent doped material is a metal complex and has a structure represented by Formula 3: In Equation 3, metal M is selected from metals with a relative atomic mass greater than 40; Ring F, ring G, ring H and ring I are selected, in the same or different ways, from unsaturated carbon rings having 5 to 30 carbon atoms, unsaturated heterocycles having 1 to 30 carbon atoms, or combinations thereof; e is selected from 0 or 1; A1-A4 are selected from single bonds, O, S, Se, (SiR”R”) each time they appear, either identically or differently. y ,PR”,NR”,(CR”R”) 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; Z1-Z4 are selected from C or N each time they appear, either identically or differently; K1-K4 are selected from single bonds, O or S, each time they appear, either the same or different. R n Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R”, 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 substituents R”, R n Substituents can be optionally linked to form rings.
11. A display component comprising the organic electroluminescent device according to any one of claims 1-10.
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