Organic electroluminescent device and electronic apparatus thereof
Patent Information
- Application Number
- CN202510305222.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-14
- Publication Date
- 2026-09-22
AI Technical Summary
该申请关注的是单一化合物的结构改变所带来的性能变化,更具体的,其关注的是在咔唑上进行特定氘代的具有式1结构的三嗪类化合物的特殊效果,但该申请并不关注其化合物与其他具有何种结构的化合物组合应用时能带来器件性能的进一步提升,尤其未公开或教导三嗪与三亚苯骨架通过咔唑取代的亚苯基相连的化合物与咔唑类化合物搭配应用时所带来的器件性能的提升
[0039]本发明提供的有机电致发光器件,通过选择具有特定式1结构的第一化合物搭配具有特定式2结构的第二化合物组合应用,提升了器件的综合性能,尤其是使得包含其的器件在寿命方面表现出了独特的优势,具有广泛的应用前景。
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Figure CN122803576A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent devices. More particularly, it relates to an organic electroluminescent device comprising a first compound having the structure of Formula 1 and a second compound having the structure of Formula 2, a composition comprising the first compound and the second compound, and an electronic device comprising the organic electroluminescent device. Background Technology
[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.
[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and VanSlyke 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). 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] Triazine organic semiconductor materials are widely used in OLEDs due to their superior photoelectric properties, redox properties, and stability.
[0009] US2022389018A1 discloses an organic electroluminescent device whose light-emitting layer comprises a structure having Formula 1. The first compound and having the structure of formula 2 The application discloses a wide range of second compounds having a triazine-triphenylene skeleton, and most of the specific structures disclosed are compounds in which triazine and triphenylene are linked through a dibenzofuran / thiophene ring. It only discloses one compound in which triazine and triphenylene are linked through a carbazole-substituted phenylene group. The triphenylene group and carbazole group in this compound are ortho-substituted on the triazine-substituted triphenylene group. This application does not disclose or teach compounds in which carbazole and triphenylene are in other relative positions (such as meta or para) on the triazine-substituted triphenylene group, nor does it teach the different effects that compounds with this special structure can produce when used in combination with compounds with carbazole and similar structures, and their impact on device performance.
[0010] CN119384416A discloses a compound having the structure of Formula 1 and an organic light-emitting device comprising the compound: Specifically, at least one of R1 to R8 is deuterium. This application focuses on the performance changes resulting from structural modifications of a single compound, and more specifically, on the particular effects of triazine compounds having the structure of Formula 1 with specific deuteration on carbazole. However, this application does not focus on the further performance improvements that can be achieved when these compounds are combined with other compounds having any structure, especially the performance improvements that can be achieved when compounds with a triazine skeleton linked to a triphenylene skeleton via a carbazole-substituted phenylene group are combined with carbazole compounds.
[0011] Currently reported triazine-based organic semiconductor materials exhibit limitations in carrier transport capability and lifetime in optoelectronic devices. Besides developing novel compounds targeting triazine-based organic semiconductor materials, finding compound combinations with better performance match to further improve device performance is also a pressing issue for those skilled in the art. Summary of the Invention
[0012] The present invention aims to provide a series of organic electroluminescent devices comprising a first compound having a specific formula 1 structure and a second compound having a specific formula 2 structure to solve at least some of the aforementioned problems. The organic electroluminescent devices can significantly improve the overall performance of the devices, for example, by having low driving voltage and / or high device efficiency, and in particular, by achieving an unexpectedly significant increase in device lifetime.
[0013] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
[0014] anode,
[0015] cathode,
[0016] And an organic layer disposed between the anode and the cathode, the organic layer comprising at least one first compound and at least one second compound;
[0017] Wherein, the first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2:
[0018]
[0019] in,
[0020] V1-V4 are selected from C and CR each time they appear, either identically or differently. v Or N, and one of V1-V4 is selected from C and connected to L;
[0021] V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N;
[0022] Z1-Z3 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z3 is selected from C and connected to L;
[0023] Z4 is selected from CR z Or N;
[0024] X1-X8 are selected from CR each time they appear, either the same or different. x Or N;
[0025] L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.
[0026] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0027] R v R z and R xEach 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;
[0028] Adjacent substituent R v They can be arbitrarily connected to form a ring;
[0029] Adjacent substituent R x They can be arbitrarily connected to form a ring;
[0030] Adjacent substituent R z They can be arbitrarily connected to form a ring;
[0031]
[0032] Ar1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0033] L T It is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.
[0034] T is selected from CR each time it appears, either the same or different. t Or N;
[0035] R tEach 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;
[0036] Adjacent substituent R t They can be arbitrarily connected to form a ring.
[0037] According to another embodiment of the present invention, a compound composition is also disclosed, comprising a first compound having the structure of Formula 1 as described in the foregoing embodiments and a second compound having the structure of Formula 2.
[0038] According to another embodiment of the present invention, an electronic device comprising the organic electroluminescent device or compound composition described in the foregoing embodiments is also disclosed.
[0039] The organic electroluminescent device provided by the present invention improves the overall performance of the device by combining a first compound having a specific formula 1 structure with a second compound having a specific formula 2 structure. In particular, the device containing the compound exhibits unique advantages in terms of lifetime and has broad application prospects. Attached Figure Description
[0040] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the organic electroluminescent devices and compound compositions disclosed herein.
[0041] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the organic electroluminescent devices and compound compositions disclosed herein. Detailed Implementation
[0042] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.
[0043] 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.
[0044] 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.
[0045] 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.
[0046] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.
[0047] 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.
[0048] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0049] 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.
[0050] 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.
[0051] 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.
[0052] 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).
[0053] 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.
[0054] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
[0055] Definition of the term "substituent group"
[0056] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0057] 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.
[0058] 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.
[0059] 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.
[0060] 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] 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.
[0066] 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.
[0067] 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.
[0068] 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.
[0069] 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.
[0070] 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.
[0071] 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.
[0072] 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.
[0073] 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.
[0074] 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.
[0075] 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.
[0076] 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.
[0077] 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.
[0078] 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:
[0079]
[0080] 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:
[0081]
[0082] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:
[0083]
[0084] 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:
[0085]
[0086] According to one embodiment of the present invention, an organic electroluminescent device is disclosed:
[0087] anode,
[0088] cathode,
[0089] And an organic layer disposed between the anode and the cathode, the organic layer comprising at least one first compound and at least one second compound;
[0090] Wherein, the first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2:
[0091]
[0092] in,
[0093] V1-V4 are selected from C and CR each time they appear, either identically or differently. v Or N, and one of V1-V4 is selected from C and connected to L;
[0094] V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N;
[0095] Z1-Z3 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z3 is selected from C and connected to L;
[0096] Z4 is selected from CR z Or N;
[0097] X1-X8 are selected from CR each time they appear, either the same or different. x Or N;
[0098] L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.
[0099] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0100] R v R z and 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, 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;
[0101] Adjacent substituent R v They can be arbitrarily connected to form a ring;
[0102] Adjacent substituent R x They can be arbitrarily connected to form a ring;
[0103] Adjacent substituent R z They can be arbitrarily connected to form a ring;
[0104]
[0105] Ar1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0106] L T It is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.
[0107] T is selected from CR each time it appears, either the same or different. t Or N;
[0108] R t 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;
[0109] Adjacent substituent R t They can be arbitrarily connected to form a ring.
[0110] In this paper, "adjacent substituent R" v "Can be optionally linked to form a ring", "adjacent substituents R" x "Can be optionally linked to form a ring", "adjacent substituents R" z "Can be optionally connected to form a loop" is intended to represent V1 to V 12 Any two adjacent substituents R v Between; any two adjacent substituents R from X1 to X8 x Between; any two adjacent substituents R from Z1 to Z4 z Between these substituents, one or more groups can connect to form a ring.
[0111] In this paper, "adjacent substituent R" t "Can be optionally linked to form a ring" is intended to represent any two adjacent substituents R t One or more sets of substituents can be linked together to form a ring.
[0112] Preferably, one or more of the aforementioned substituents can be linked to form a carbocyclic ring (which may be aromatic or non-aromatic) or a heterocyclic ring (which may be aromatic or non-aromatic); more preferably, they can be linked to form a carbocyclic ring or heterocyclic ring having 6-24 ring atoms; even more preferably, they can be linked to form a carbocyclic ring or heterocyclic ring having 6-12 ring atoms; and even more preferably, they can be linked to form a benzene ring or an indole ring. Obviously, any adjacent substituents may not be linked to form a ring.
[0113] According to one embodiment of the invention, unless explicitly defined that adjacent substituents can optionally link to form a ring, adjacent substituents in the compound cannot link to form a ring. For example, in the structure of Formula 1, adjacent substituent R z With R x The links are not connected to form a loop, R x It does not form a ring with the substituents on L.
[0114] According to one embodiment of the present invention, the first compound contains only one substituted or unsubstituted carbazole group.
[0115] According to one embodiment of the present invention, the first compound has a different structure from the second compound.
[0116] According to one embodiment of the present invention, V2 is selected from C and is connected to L in Formula 1.
[0117] According to one embodiment of the present invention, Z2 is selected from C and is connected to L in Formula 1.
[0118] According to one embodiment of the present invention, the first compound has a structure represented by formula 1-1:
[0119]
[0120] V1, V3-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N;
[0121] Z1, Z3, and Z4 are selected from CR each time they appear, either identically or differently. z Or N;
[0122] X1-X8 are selected from CR each time they appear, either the same or different. x Or N;
[0123] L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.
[0124] Ar appears in the same or different forms, selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0125] R v R z and 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, 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;
[0126] Adjacent substituent R v They can be arbitrarily connected to form a ring;
[0127] Adjacent substituent R x They can be arbitrarily connected to form a ring;
[0128] Adjacent substituent R z They can be arbitrarily connected to form a ring.
[0129] According to one embodiment of the present invention, V1-V4 are selected from C or CR each time they appear, either identically or differently. v V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v; and / or Z1-Z3 are selected from C or CR each time they appear, either identically or differently. z Z4 is selected from CR each time it appears, either the same or different. z ; and / or X1-X8 are selected from CR each time they appear, either identically or differently. x .
[0130] According to one embodiment of the invention, L, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms containing one or more heteroatoms selected from O, S, Se, Si, P, Ge and B, or combinations thereof.
[0131] According to one embodiment of the invention, L, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, or combinations thereof.
[0132] According to one embodiment of the invention, L, each time it appears, is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or combinations thereof.
[0133] According to one embodiment of the invention, L is selected from single bonds or phenylene groups each time it appears, either identically or differently.
[0134] According to one embodiment of the present invention, L1, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.
[0135] According to one embodiment of the invention, L1, each time it appears, is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, or combinations thereof.
[0136] According to one embodiment of the invention, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.
[0137] According to one embodiment of the invention, Ar, each time it appears, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.
[0138] According to one embodiment of the present invention, R v R z and 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, 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
[0139] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, halogen, 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
[0140] According to one embodiment of the present invention, R v R z and R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, cyano, and combinations thereof.
[0141] According to one embodiment of the present invention, at least one of X1-X8 is selected from CR x The R xEach occurrence, whether identical or different, is selected from: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.
[0142] According to one embodiment of the present invention, at least one of X5, X6, and X7 is selected from CR. x The R x Each occurrence, whether identical or different, is selected from: deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.
[0143] According to one embodiment of the present invention, at least one of X5, X6, and X7 is selected from CR. x The R x Each occurrence, whether identical or different, is selected from: deuterium, halogens, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.
[0144] According to one embodiment of the present invention, the first compound is selected from the group consisting of compounds A-1 to A-273, the specific structures of which are given in claim 9.
[0145] According to one embodiment of the present invention, the hydrogen in compounds A-1 to A-273 may be partially or completely replaced by deuterium.
[0146] According to one embodiment of the present invention, the second compound has a structure represented by formula 2-1 or formula 2-2:
[0147]
[0148] in,
[0149] T and T' are selected from C and CR each time they appear, either identically or differently. t Or N; In Equation 2-1, one of T is selected from C and connected to L2; one of T' is selected from C and connected to L2;
[0150] T is selected from CR each time it appears, either the same or different. t Or N;
[0151] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S; when multiple Rs exist simultaneously g At that time, multiple R g Same or different;
[0152] L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted alkylene with 1-20 carbon atoms, substituted or unsubstituted cycloalkylene with 3-20 carbon atoms, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, or combinations thereof.
[0153] R t R g Each time it appears, it is selected from the group consisting of, either identically or differently, 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 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... 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;
[0154] Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0155] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.
[0156] In this paper, "adjacent substituent R" t R g"Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R t Between the two substituents R g Between, substituent R t and R g Between these adjacent substituent groups, any one or more can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.
[0157] According to one embodiment of the present invention, the second compound has a structure represented by one of formulas 2-a to 2-j and 3-a to 3-f:
[0158]
[0159]
[0160] in,
[0161] T, T', T” are selected from CR each time they appear, either identically or differently. t Or N;
[0162] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S; when multiple Rs exist simultaneously g At that time, multiple R g Same or different;
[0163] L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted alkylene with 1-20 carbon atoms, substituted or unsubstituted cycloalkylene with 3-20 carbon atoms, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, or combinations thereof.
[0164] R t R gEach time it appears, it is selected from the group consisting of, either identically or differently, 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 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... 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;
[0165] Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0166] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.
[0167] According to one embodiment of the present invention, the second compound is selected from those having structures represented by formula 2-h and formula 3-e.
[0168] According to one embodiment of the present invention, L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted aryl group having 6-20 carbon atoms, substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, or a combination thereof.
[0169] According to one embodiment of the present invention, L T L T ', L2 each time it appears is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or a combination thereof.
[0170] According to one embodiment of the present invention, L T L T', L2 appears in the same or different ways, selected from single bonds or phenylene.
[0171] According to one embodiment of the present invention, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.
[0172] According to one embodiment of the invention, Ar1 and Ar2, each time they appear, are selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
[0173] According to one embodiment of the present invention, G is selected from NR each time it appears, either identically or differently. g 、O or S.
[0174] According to one embodiment of the present invention, G is selected from NR each time it appears, either identically or differently. g ;R g Each time it appears, it is selected from the group consisting of, either identically or differently, 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 alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, hydroxyl groups having 0-20 carbon atoms, and combinations thereof.
[0175] According to one embodiment of the present invention, G is selected from NR each time it appears, either identically or differently. g ;R g Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.
[0176] According to one embodiment of the present invention, T, T', T" are selected from CR each time they appear, either identically or differently. t The R tEach time it appears, it is selected from the group consisting of, either identically or differently, 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 alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, hydroxyl groups having 0-20 carbon atoms, and combinations thereof.
[0177] According to one embodiment of the present invention, at least one R t Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, cyano, mercapto, hydroxyl, and combinations thereof.
[0178] According to one embodiment of the present invention, at least one hydrogen atom in the structure of the first compound and / or the second compound is replaced by deuterium.
[0179] According to one embodiment of the present invention, the hydrogen in the first compound and / or the second compound can be partially or wholly replaced by deuterium.
[0180] According to one embodiment of the present invention, the deuteration rate of the first compound and / or the second compound is 5%-100%.
[0181] According to one embodiment of the present invention, the deuteration rate of the first compound and / or the second compound is 30%-100%.
[0182] According to one embodiment of the present invention, the deuteration rate of the first compound and / or the second compound is 50%-100%.
[0183] In this embodiment, the "deuteration rate of the compound" refers to the percentage of the number of deuterium atoms in the compound structure relative to the total number of hydrogen and deuterium atoms in the compound structure.
[0184] According to one embodiment of the present invention, the second compound is selected from the group consisting of PH-1 to PH-246, the specific structures of which are given in claim 15.
[0185] According to one embodiment of the present invention, the hydrogen in compounds PH-1 to PH-246 may be partially or completely replaced by deuterium.
[0186] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the first compound and the second compound are host materials.
[0187] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the first compound and the second compound are host materials; the light-emitting layer further comprises at least one metal complex having M(L) a ) m (L b ) n (L c ) q The general formula;
[0188] Metal M is selected from metals with a relative atomic mass greater than 40;
[0189] L a L b and L c The first, second, and third ligands, respectively, coordinate with the metal M. a L b L c They can be the same or different;
[0190] L a L b and L c They can be selectively linked to form multidentate ligands;
[0191] m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different; when q is 2, the two Ls c They can be the same or different;
[0192] ligand L a It has the structure shown in Equation 4:
[0193]
[0194] When ring A1 and ring A2 appear, they are selected, either identically or differently, from substituted or unsubstituted aromatic rings having 5-30 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-30 ring atoms, or combinations thereof;
[0195] P1 and P2 are selected from C or N each time they appear, either in the same or different ways.
[0196] D1 and D2 are selected from single bonds, O or S, each time they appear, either the same or different.
[0197] L1' is selected from the group consisting of: single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 5-30 carbon atoms, and combinations thereof; when two R's are present, the two R's may be the same or different;
[0198] a1 is selected from 0 or 1;
[0199] R 11 and R 12 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0200] R 11 R 12 R', each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0201] Adjacent substituent R 11 R 12 R' can be arbitrarily connected to form a loop;
[0202] ligand L b and L c Each occurrence is selected from monoanionic bidentate ligands, either identically or differently.
[0203] In this embodiment, "adjacent substituent R" 11 R 12 "R' can optionally connect to form a ring" is intended to denote adjacent substituent groups, for example, two substituents R11 Between the two substituents R 12 Between, between the two substituents R', and between the substituents R 11 and R 12 Between, substituents R' and R 11 Between, substituents R' and R 12 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0204] According to one embodiment of the present invention, the ligand L b and L c Each occurrence is either identical or different from the group consisting of the following structures:
[0205]
[0206] in,
[0207] R a and R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0208] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;
[0209] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;
[0210] R a R b R c R N1 R N2 R C1 and R C2Each 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;
[0211] Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.
[0212] In this embodiment, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent Ra and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 Between these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to: Where W is selected from O, S, Se, NR w or CR w R w ; wherein R w R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.
[0213] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears.
[0214] According to one embodiment of the invention, the metal M is selected from Pt or Ir each time it appears.
[0215] According to an embodiment of the present invention, the metal complex has M(L) a1 ) j (L b1 ) k The general formula structure, wherein the metal M is selected from metals with a relative atomic mass greater than 40;
[0216] L a1 L b1 The first and second ligands, respectively, coordinate with M; L a1 L b1 They can be selectively linked to form multidentate ligands;
[0217] j is 1, 2, or 3; k is 0, 1, or 2; the sum of j and k equals the oxidation state of M; when j is greater than or equal to 2, multiple L a1 They can be the same or different; when k is 2, the two L'sb1 They can be the same or different;
[0218] The L a1 It has the structure shown in Equation 4-1:
[0219]
[0220] in,
[0221] Ring F1 is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
[0222] Ring F2 is selected from 5-membered heteroaryl rings or 6-membered heteroaryl rings;
[0223] Rings F1 and F2 are fused together via U1 and U2;
[0224] U1 and U2 are selected from C or N each time they appear, either in the same or different ways.
[0225] R f1 R f2 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0226] F is selected from CR each time it appears, either the same or different. f Or N;
[0227] R f1 R f2 R f Each time it appears, it is selected from the group consisting of, either identically or differently, 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 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... 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;
[0228] Adjacent substituent Rf1 R f2 R f They can be arbitrarily connected to form a loop;
[0229] The ligand L b1 It has a structure as shown in Equation 4-2:
[0230]
[0231] Among them, R 21 To R 27 Each is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2- Alkynyl groups with 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.
[0232] In this paper, adjacent substituents R f1 R f2 R f The ability to optionally connect to form a ring is intended to indicate the presence of a substituent R. f1 Substituent R f2 Substituent R f When, adjacent substituent groups, such as adjacent substituent R f1 Substituents R between and adjacent f2 Substituents R between and adjacent f Substituents R between and adjacent f1 With R f2 Substituents R between and adjacent f1 With R f Between and adjacent substituents R f2 With R fBetween these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... f1 Substituent R f2 Substituent R f At the same time, these substituent groups may not be connected to form a ring.
[0233] According to an embodiment of the present invention, in formula 4-2, R 21 -R 23 At least one of them is selected from 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, or combinations thereof; and / or R 24 -R 26 At least one of them is selected from 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 heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
[0234] According to an embodiment of the present invention, in formula 4-2, R 21 -R 23 At least two of them are selected from 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, or combinations thereof; and / or R 24 -R 26 It contains at least two alkyl groups selected from 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 heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
[0235] According to an embodiment of the present invention, in formula 4-2, R 21 -R 23 At least two of them, each time appearing identically or differently, are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or R 24 -R 26 At least two of them, each time appearing identically or differently, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
[0236] According to an embodiment of the present invention, the metal complex has Ir(L a1 )2(Lb1 The general formula structure of ).
[0237] According to one embodiment of the present invention, the metal complex is an Ir metal complex and includes ligand L. a1 The L a1 It has the structure shown in Formula 4-1 and contains at least one structural unit selected from the group consisting of a 6-membered 6-membered aromatic ring, a 6-membered 6-membered heteroaromatic ring, a 6-membered 5-membered aromatic ring and a 6-membered 5-membered heteroaromatic ring.
[0238] According to one embodiment of the present invention, the metal complex is an Ir metal complex and includes ligand L. a1 The L a1 It has the structure shown in Formula 4-1 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.
[0239] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 4-3:
[0240]
[0241] in,
[0242] Metal M is selected from metals with a relative molecular mass greater than 40 each time it appears, either the same or different.
[0243] Each time rings A1-A4 appear, they are selected from substituted or unsubstituted aromatic rings having 6-30 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-30 ring atoms, or combinations thereof;
[0244] Each occurrence of L1'-L4' is selected from the following groups, either identically or differently: single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 5-30 carbon atoms, and combinations thereof; when two R's are present simultaneously, the two R's are identical or different;
[0245] Each occurrence of a1-a4, whether identical or different, is selected from 0 or 1;
[0246] P1-P4 are selected from C or N each time they appear in the same or different ways;
[0247] D1-D4 appearing in the same or different ways each time are selected from a single bond, O or S;
[0248] R 11 -R 14 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0249] R 11 -R 14 R', each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0250] Adjacent substituent R 11 -R 14 R' can be optionally connected to form a loop.
[0251] In this embodiment, "adjacent substituent R" 11 -R 14 "R' can optionally connect to form a ring" is intended to indicate adjacent substituent groups, for example, adjacent substituents R 11 Between, adjacent substituents R 12 Between, adjacent substituents R 13 Between, adjacent substituents R 14 One or more of these substituents can connect to form a ring, either between the substituents R' and between adjacent substituents R'. It is also possible that these substituents do not connect to form a ring.
[0252] According to one embodiment of the present invention, the metal complex has Ir(L) a ) m (L b ) 3-m The general formula structure, and by
[0253] The structure represented by Equation 4-4:
[0254]
[0255] in,
[0256] m can be 0, 1, 2, or 3; when m is 2 or 3, multiple L a Same or different; multiple L when m is 0 or 1 b Same or different;
[0257] T1-T6 each time appear in the same or different selections from CR T Or N;
[0258] R a R b and R d Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0259] R a R b R d and R T 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, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0260] Adjacent substituent R a R b They can be arbitrarily connected to form a loop;
[0261] Adjacent substituent R d R T They can be arbitrarily connected to form a ring.
[0262] In this embodiment, "adjacent substituent R" a R b"Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R a Between two adjacent substituents R b Between, and adjacent substituents R a and R b Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0263] In this embodiment, "adjacent substituent R" d R T "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R T Between two adjacent substituents R d Between, and adjacent substituents R d and R T Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.
[0264] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T And the R T It is selected from 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, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.
[0265] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T And the R T It is either fluorine or cyanide.
[0266] According to one embodiment of the present invention, at least one of T1-T4 is selected from CR T And the R T It is either fluorine or cyanide.
[0267] According to one embodiment of the present invention, at least two of T1-T6 are selected from CR T And one of the R T It is either fluorine or cyano, and the other R T It is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.
[0268] According to one embodiment of the present invention, T1-T6 are selected from CR each time they occur, either identically or differently. T Or N, and at least one of T1-T6 is selected from N, for example, one or two of T1-T6 are selected from N.
[0269] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds GD1 to GD77:
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276] According to one embodiment of the present invention, the hydrogen in the compounds GD1 to GD77 can be partially or completely replaced by deuterium.
[0277] According to one embodiment of the present invention, the organic electroluminescent device emits green light.
[0278] According to one embodiment of the present invention, the organic electroluminescent device emits white light.
[0279] According to one embodiment of the present invention, the metal complex is doped in the first compound and the second compound, and the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
[0280] According to one embodiment of the present invention, the metal complex is doped in the first compound and the second compound, and the metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.
[0281] According to one embodiment of the present invention, a compound composition is also disclosed, comprising a first compound having a structure represented by Formula 1 and a second compound having a structure represented by Formula 2; the first compound and the second compound are as shown in any of the foregoing embodiments.
[0282] According to one embodiment of the present invention, an electronic device is also disclosed, which includes an organic electroluminescent device or compound composition as described in any of the foregoing embodiments.
[0283] Combination with other materials
[0284] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0285] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0286] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in 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 samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.
[0287] Material synthesis examples:
[0288] The preparation method of the first compound of this invention is not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:
[0289] Synthesis Example 1: Synthesis of compound A-2
[0290] Step 1: Synthesis of intermediate C
[0291]
[0292] In a three-necked round-bottom flask, intermediate A (3.84 g, 22.00 mmol), intermediate B (6.10 g, 20.00 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.46 g, 0.40 mmol), K2CO3 (5.52 g, 40.00 mmol), 120 mL toluene, 30 mL EtOH, and 30 mL H2O were added sequentially. The mixture was heated under reflux overnight under nitrogen protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was separated, and the aqueous phase was extracted with DCM. The organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 30:1 to 8:1) to give a white solid intermediate C (6.60 g, 18.50 mmol), with a yield of 92.50%.
[0293] Step 2: Synthesis of intermediate D
[0294]
[0295] In a three-necked round-bottom flask, intermediate C (6.60 g, 18.50 mmol), pinacol diboronate (6.11 g, 24.05 mmol), palladium acetate (Pd(OAc)2, 0.21 g, 0.93 mmol), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (X-Phos, 0.88 g, 1.85 mmol), and potassium acetate (KOAc, 3.60 g, 37.00 mmol) were added to 1,4-dioxane (100 mL). The mixture was heated to reflux overnight under nitrogen protection. Heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 8:1 to 3:1) to give a white solid intermediate D (7.60 g, 16.95 mmol), with a yield of 91.62%.
[0296] Step 3: Synthesis of intermediate G
[0297]
[0298] In a three-necked round-bottom flask, intermediates D (4.48 g, 10.00 mmol), E (2.68 g, 10.00 mmol), Pd(PPh3)4 (0.23 g, 0.20 mmol), K2CO3 (2.76 g, 20.00 mmol), 40 mL toluene, 10 mL EtOH, and 10 mL H2O were added sequentially. The mixture was heated under reflux overnight under nitrogen protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was separated, and the aqueous phase was extracted with DCM. The organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 10:1 to 3:1) to give a white solid intermediate G (4.80 g, 8.67 mmol), with a yield of 86.70%.
[0299] Step 4: Synthesis of compound A-2
[0300]
[0301] In a three-necked round-bottom flask, intermediate G (4.80 g, 8.67 mmol), intermediate H (1.88 g, 11.27 mmol), cesium carbonate (5.65 g, 17.34 mmol), and 50 mL of N,N-dimethylacetamide (DMAc) were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction solution was poured into a large volume of water, precipitating a large amount of solid. The solid was filtered under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a pale yellow solid (3.00 g, 4.28 mmol), with a yield of 49.37%. The product was identified as the target product A-2, with a molecular weight of 700.3.
[0302] Synthesis Example 2: Synthesis of compound A-22
[0303] Step 1: Synthesis of compound A-22
[0304]
[0305] In a three-necked round-bottom flask, intermediate G (4.43 g, 8.00 mmol), intermediate I (2.14 g, 8.80 mmol), cesium carbonate (5.21 g, 16.00 mmol), and 50 mL of N,N-dimethylacetamide (DMAc) were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction solution was poured into a large volume of water, precipitating a large amount of solid. The solid was filtered under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a pale yellow solid (4.30 g, 5.53 mmol), with a yield of 69.13%. The product was identified as the target product A-22, with a molecular weight of 776.3.
[0306] Synthesis Example 3: Synthesis of compound A-29
[0307] Step 1: Synthesis of compound A-29
[0308]
[0309] In a three-necked round-bottom flask, intermediate G (4.43 g, 8.00 mmol), intermediate L (2.14 g, 8.80 mmol), cesium carbonate (5.21 g, 16.00 mmol), and 50 mL of N,N-dimethylacetamide (DMAc) were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction solution was poured into a large volume of water, precipitating a large amount of solid. The solid was filtered under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a pale yellow solid (4.40 g, 5.66 mmol), with a yield of 70.75%. The product was identified as the target product A-29, with a molecular weight of 776.3.
[0310] Synthesis Example 4: Synthesis of Compound A-36
[0311] Step 1: Synthesis of compound A-36
[0312]
[0313] In a three-necked round-bottom flask, intermediate G (4.43 g, 8.00 mmol), intermediate M (2.14 g, 8.80 mmol), cesium carbonate (5.21 g, 16.00 mmol), and 50 mL of N,N-dimethylacetamide (DMAc) were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction solution was poured into a large volume of water, precipitating a large amount of solid. The solid was filtered under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a pale yellow solid (4.30 g, 5.53 mmol), with a yield of 69.13%. The product was identified as the target product A-36, with a molecular weight of 776.3.
[0314] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0315] The second compound used in this invention can be obtained by referring to preparation methods in the prior art, for example, by referring to CN114599647A, WO2023282602A1, CN117222638A, and CN117044425A. The preparation methods will not be repeated here. The above-listed documents are merely exemplary, and those skilled in the art can easily obtain other documents.
[0316] The fabrication method of the electroluminescent device is not limited. The fabrication method in the following embodiments is merely an example and should not be construed as limiting. Those skilled in the art can reasonably improve the fabrication method of the following embodiments based on the prior art. For example, the proportion of various materials in the light-emitting layer is not particularly limited. Those skilled in the art can reasonably select within a certain range based on the prior art. For instance, based on the total weight of the light-emitting layer materials, the main material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the main material can account for 90%-99%, and the light-emitting material can account for 1%-10%; or the main material can account for 94%-99%, and the light-emitting material can account for 1%-6%. Furthermore, the main material can be one or two materials, wherein the ratio of the two main materials to the main material can be 100:0 to 1:99; or, the ratio can be 80:20 to 20:80; or, the ratio can be 60:40 to 40:60.
[0317] Device Examples
[0318] Device Example 1
[0319] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, the ITO anode was sequentially evaporated at a rate of 0.1-2 Å / s via thermal vacuum evaporation. Compounds HT and HT1 were co-deposited as a hole injection layer (HIL, weight ratio 97:3) with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound PH-1 was used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the second compound PH-113, the first compound A-2, and compound GD1 of the present invention are co-deposited as the luminescent layer (EML, weight ratio 47:47:6), with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL, weight ratio 40:60), with a thickness of [missing information]. Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer, and a 120 nm thick layer of aluminum was deposited as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.
[0320] Device Example 2
[0321] The preparation method of device example 2 is the same as that of device example 1, except that compound PH-115 is used instead of compound PH-113 in the light-emitting layer (EML).
[0322] Device Example 3
[0323] The preparation method of device Example 3 is the same as that of device Example 1, except that compound PH-1 is used instead of compound PH-113 in the light-emitting layer (EML), compound A-22 is used instead of compound A-2, and the weight ratio of compound PH-1:compound A-22:GD1 is 52:42:6.
[0324] Device Example 4
[0325] The preparation method of device example 4 is the same as that of device example 3, except that compound A-29 is used instead of compound A-22 in the light-emitting layer (EML).
[0326] Device Example 5
[0327] The preparation method of device example 5 is the same as that of device example 3, except that compound A-2 is used instead of compound A-22 in the light-emitting layer (EML).
[0328] Device Example 6
[0329] The preparation method of device example 6 is the same as that of device example 3, except that compound A-36 is used instead of compound A-22 in the light-emitting layer (EML).
[0330] Device Comparison Example 1
[0331] The preparation method of Comparative Example 1 is the same as that of Example 1, except that only compound A-2 and compound GD1 are co-deposited to form the light-emitting layer (EML), and the weight ratio of compound A-2 to compound GD1 is 94:6.
[0332] Device Comparison Example 2
[0333] The preparation method of Comparative Example 2 is the same as that of Example 1, except that compound C-1 is used instead of compound A-2 in the light-emitting layer (EML).
[0334] The detailed device layer structure and thickness are shown in Table 1 below. The layers used are made of more than one material, and are obtained by doping different compounds in the weight ratios specified herein.
[0335] Table 1. Partial device structures of Device Examples 1 to 6 and Comparative Examples 1 and 2.
[0336]
[0337]
[0338] The structure of the materials used in the device is shown below:
[0339]
[0340]
[0341] Table 2 shows the results at 15 mA / cm 2 CIE data of the device measured at constant current density, drive voltage (V), external quantum efficiency (EQE); and at 80 mA / cm². 2 Device lifetime (LT95) measured at constant current density.
[0342] Table 2 Device data for Examples 1 and 2 and Comparative Examples 1 and 2
[0343] Example 1 (0.339,0.638) 3.37 23.84 83 Example 2 (0.340,0.637) 3.34 23.89 118 Comparative Example 1 (0.346,0.631) 3.76 17.26 11 Comparative Example 2 (0.339,0.637) 3.53 23.53 40
[0344] Examples 1 and 2 are devices comprising specific compound combinations of the present invention (a first compound having a specific formula 1 structure and a second compound having a formula 2 structure). Table 2 shows that devices 1 and 2 exhibit superior overall performance compared to comparative examples 1 and 2 that do not contain the specific compound combinations of the present invention. Specifically:
[0345] Comparative Example 1 is a device that uses only a first compound (A-2) with a specific Formula 1 structure as the main component. As shown in Table 2, the device performance of Comparative Example 1 still has room for improvement. The inventors of this invention were pleasantly surprised to discover through experiments that when an indole-carbazole second compound with a specific Formula 2 structure is combined with a triazine first compound with a specific Formula 1 structure and applied to the device, a significant improvement in device performance can be achieved. Specifically, compared to Comparative Example 1, the driving voltage of Examples 1 and 2 decreased by 0.39V and 0.42V, respectively; the EQE increased by 38.12% and 38.41%, respectively. More importantly, the device lifetime of Examples 1 and 2 increased significantly by 6.55 times and 9.73 times, respectively. This data demonstrates that, compared to devices using only a triazine compound with a Formula 1 structure as the main component, the combination of a carbazole compound with a Formula 2 structure and a specific triazine compound with a Formula 1 structure in this invention can further balance the transport of electrons and holes in the device, resulting in a significant improvement in device performance, especially a breakthrough in lifetime.
[0346] Comparative Example 2 is a device comprising a combination of compounds not found in this invention (a non-inventive first compound C-1 and an inventive second compound PH-113). As shown in Table 2, compared to Comparative Example 2, Example 1 also achieved a reduction in voltage and an increase in efficiency; in particular, its lifetime was 2.08 times that of Comparative Example 2. This data demonstrates that, compared to other devices using a first compound without a specific Formula 1 structure combined with a second compound having a Formula 2 structure, the device using a triazine compound with a specific Formula 1 structure combined with a carbazole compound with a Formula 2 structure exhibits unique advantages and superior overall performance. In particular, the device in Example 2, employing a deuterated indole carbazole second compound with a Formula 2 structure combined with a triazine compound with a Formula 1 structure, demonstrated extremely excellent performance and an exceptionally long device lifetime.
[0347] The above data demonstrates from multiple perspectives that the triazine-based first compound with a specific Formula 1 structure and the carbazole-based second compound with a Formula 2 structure selected in this invention are more compatible in terms of performance. The resulting compound combination can further balance the transport of electrons and holes in the device, thereby significantly improving the device performance, especially achieving a significant improvement in device lifetime.
[0348] In addition to the aforementioned combination of an indolecarbazole second compound having the structure of Formula 2 with the first compound of the present invention having the structure of Formula 1, the inventors of the present invention further tested other devices comprising combinations of a bicarbazole second compound having the structure of Formula 2 and a first compound having the structure of Formula 1. The results showed that they also exhibited excellent device performance. Specifically:
[0349] Table 3 shows the results of Examples 3 to 6 at 15 mA / cm². 2 CIE data of the device measured at constant current density, external quantum efficiency (EQE), and at 80 mA / cm². 2 Device lifetime (LT95) measured at constant current density.
[0350] Table 3 Device data for Examples 3 to 6
[0351] Example 3 (0.339,0.637) 23.90 53 Example 4 (0.340,0.636) 24.20 65 Example 5 (0.340,0.636) 24.00 49 Example 6 (0.340,0.636) 24.00 54
[0352] The data in Table 3 show that the devices in Examples 3-6, which contain the triazine first compound of the present invention having a specific structure of Formula 1 combined with the bicarbazole second compound having a structure of Formula 2, also exhibit excellent overall performance. For example, Example 5 differs from Comparative Example 1 only in that Example 5 uses a combination of the second compound (PH-1) having a structure of Formula 2 and the first compound (A-2) having a structure of Formula 1, while Comparative Example 1 uses the first compound alone as the main material. As can be seen from the data in Tables 2 and 3, Example 5 has higher efficiency and lifespan, with the lifespan even reaching 4.5 times that of Comparative Example 1, demonstrating excellent overall performance.
[0353] Furthermore, the inventors of this invention used a second compound (PH-1) having the structure of Formula 2 in combination with various first compounds having different structures with the framework of Formula 1 in device examples 3, 4, and 6. Table 3 shows that they all exhibited extremely excellent overall performance, even demonstrating further improvements in efficiency and lifetime. In particular, in Example 4, when the first compound of this invention with aryl substituents at specific positions was used in combination with a bicarbazole-based second compound having the structure of Formula 2, the device lifetime showed a surprisingly significant breakthrough improvement, even reaching 5.91 times that of Comparative Example 1, demonstrating broad application prospects and value.
[0354] In summary, the combination of a triazine-based first compound with a specific structure of Formula 1 and a carbazole-based second compound with a structure of Formula 2, selected in this invention, can reduce device driving voltage, improve device efficiency, and significantly extend device lifespan, resulting in superior device performance and unexpected unique advantages. This provides the industry with an excellent material combination for the organic layer of devices.
[0355] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.
Claims
1. An organic electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising at least one first compound and at least one second compound; Wherein, the first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2: in, V1-V4 are selected from C and CR each time they appear, either identically or differently. v Or N, and one of V1-V4 is selected from C and connected to L; V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N; Z1-Z3 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z3 is selected from C and connected to L; Z4 is selected from CR z Or N; X1-X8 are selected from CR each time they appear, either the same or different. x Or N; L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; R v R z and 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, 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 v They can be arbitrarily connected to form a ring; Adjacent substituent R x They can be arbitrarily connected to form a ring; Adjacent substituent R z They can be arbitrarily connected to form a ring; Ar1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; L T It is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. T is selected from CR each time it appears, either the same or different. t Or N; R t 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 t They can be arbitrarily connected to form a ring.
2. The organic electroluminescent device as described in claim 1, wherein, V2 is selected from C and connected to L in Equation 1.
3. The organic electroluminescent device as described in claim 1, wherein, The first compound has a structure represented by Formula 1-1: V1, V3-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N; Z1, Z3, and Z4 are selected from CR each time they appear, either identically or differently. z Or N; X1-X8 are selected from CR each time they appear, either the same or different. x Or N; L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. Ar appears in the same or different forms, selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; R v R z and 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, 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 v They can be arbitrarily connected to form a ring; Adjacent substituent R x They can be arbitrarily connected to form a ring; Adjacent substituent R z They can be arbitrarily connected to form a ring.
4. The organic electroluminescent device as described in claim 1, wherein, V1-V4 are selected from C or CR each time they appear, either identically or differently. v V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v ; and / or Z1-Z3 are selected from C or CR each time they appear, either identically or differently. z Z4 is selected from CR each time it appears, either the same or different. z ; and / or X1-X8 are selected from CR each time they appear, either identically or differently. x .
5. The organic electroluminescent device as described in claim 1 or 3, wherein, L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof. Preferably, L and L1 are selected, each time they appear, from the same or different single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, or combinations thereof.
6. The organic electroluminescent device according to any one of claims 1-5, wherein, Ar and Ar1, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof; Preferably, Ar and Ar1, each time they appear, are selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.
7. The organic electroluminescent device according to any one of claims 1-6, wherein, R v R z and 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, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof. Preferably, R v R z and R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, cyano, and combinations thereof.
8. The organic electroluminescent device according to any one of claims 1-7, wherein, At least one of X1-X8 is selected from CR x The R x Each time it appears the same or different, it is selected from: deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms, substituted or unsubstituted heteroaryl with 3-20 carbon atoms, cyano, and combinations thereof; Preferably, at least one of X5, X6, and X7 is selected from CR. x The R x Each time it appears the same or different, it is selected from: deuterium, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms, substituted or unsubstituted heteroaryl with 3-20 carbon atoms, cyano, and combinations thereof; More preferably, at least one of X5, X6, and X7 is selected from CR. x The R x Each occurrence, whether identical or different, is selected from: deuterium, halogens, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.
9. The organic electroluminescent device as claimed in claim 1, wherein, The first compound is selected from the group consisting of compounds A-1 to A-273, and the specific structures of compounds A-1 to A-273 are as follows: Optionally, the hydrogen in compounds A-1 to A-273 can be partially or completely replaced by deuterium.
10. The organic electroluminescent device as claimed in claim 1, wherein, The second compound has a structure represented by formula 2-1 or formula 2-2: in, T and T' are selected from C and CR each time they appear, either identically or differently. t Or N; T is selected from CR each time it appears, either the same or different. t Or N; G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S; when multiple Rs exist simultaneously g At that time, multiple R g Same or different; L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted alkylene with 1-20 carbon atoms, substituted or unsubstituted cycloalkylene with 3-20 carbon atoms, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, or combinations thereof. R t R g Each time it appears, it is selected from the group consisting of, either identically or differently, 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 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... 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; Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Adjacent substituent R t R g They can be arbitrarily connected to form a ring.
11. The organic electroluminescent device of claim 1, wherein the second compound has a structure represented by any one of formulas 2-a to 2-j and 3-a to 3-f: in, T, T', T” are selected from CR each time they appear, either identically or differently. t Or N; G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S; when multiple Rs exist simultaneously g At that time, multiple R g Same or different; L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted alkylene with 1-20 carbon atoms, substituted or unsubstituted cycloalkylene with 3-20 carbon atoms, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, or combinations thereof. R t R g Each time it appears, it is selected from the group consisting of, either identically or differently, 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 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... 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; Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Adjacent substituent R t R g They can be arbitrarily connected to form a loop; Preferably, the second compound is selected from structures represented by formula 2-h and formula 3-e.
12. The organic electroluminescent device as claimed in claim 10 or 11, wherein, L T L T ', L2 each time it appears is the same or different selected from single bond, substituted or unsubstituted aryl group having 6-20 carbon atoms, substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, or a combination thereof; Preferably, L T L T ', L2 each time it appears is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or a combination thereof; More preferably, L T L T ', L2 appears in the same or different ways, selected from single bonds or phenylene.
13. The organic electroluminescent device as described in claim 10 or 11, wherein, G is selected from NR each time it appears, either the same or different. g , O or S; Preferably, G is selected from NR each time it appears, either identically or differently. g ;R g Each time it appears, it is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, hydroxyl groups having 0-20 carbon atoms, and combinations thereof. More preferably, R g Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.
14. The organic electroluminescent device according to any one of claims 11-13, wherein, T, T', T” are selected from CR each time they appear, either identically or differently. t The R t Each time it appears, it is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, hydroxyl groups having 0-20 carbon atoms, and combinations thereof. Preferably, at least one R t Each time it appears, it is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, cyano, mercapto, hydroxyl, and combinations thereof.
15. The organic electroluminescent device as claimed in claim 1, wherein, The second compound is selected from the group consisting of PH-1 to PH-246, and the specific structures of PH-1 to PH-246 are shown below: In the compounds PH-1 to PH-246, the hydrogen can be partially or completely replaced by deuterium.
16. The organic electroluminescent device of claim 1, wherein the organic layer is a light-emitting layer, and the first compound and the second compound are host materials; the light-emitting layer further comprises at least one metal complex having M(L) a ) m (L b ) n (L c ) q The general formula; Metal M is selected from metals with a relative atomic mass greater than 40; L a L b and L c The first, second, and third ligands, respectively, coordinate with the metal M. a L b L c They can be the same or different; L a L b and L c They can be selectively linked to form multidentate ligands; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different; when q is 2, the two Ls c They can be the same or different; ligand L a It has the structure shown in Equation 4: When ring A1 and ring A2 appear, they are selected, either identically or differently, from substituted or unsubstituted aromatic rings having 5-30 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-30 ring atoms, or combinations thereof; P1 and P2 are selected from C or N each time they appear, either in the same or different ways. D1 and D2 are selected from single bonds, O or S, each time they appear, either the same or different. L1' is selected from the group consisting of: single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 5-30 carbon atoms, and combinations thereof; when two R's are present, the two R's may be the same or different; a1 is selected from 0 or 1; R 11 and R 12 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R 11 R 12 R', each time appearing, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R 11 R 12 R' can be arbitrarily connected to form a loop; ligand L b and L c Each occurrence may be the same or different from a monoanionic bidentate ligand; Preferably, the ligand L b and L c Each occurrence is either identical or different from the group consisting of the following structures: in, R a and R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ; R a R b R c R N1 R N2 R C1 and R C2 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 a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.
17. A compound composition comprising a first compound and a second compound; in, The first compound has a structure represented by Formula 1, and the second compound has a structure represented by Formula 2: in, V1-V4 are selected from C and CR each time they appear, either identically or differently. v Or N, and one of V1-V4 is selected from C and connected to L; V5-V 12 Each time it appears, it is selected from CR in the same or different ways. v Or N; Z1-Z3 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z3 is selected from C and connected to L; Z4 is selected from CR z Or N; X1-X8 are selected from CR each time they appear, either the same or different. x Or N; L, L1, each time appearing, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; R v R z and 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, 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 v They can be arbitrarily connected to form a ring; Adjacent substituent R x They can be arbitrarily connected to form a ring; Adjacent substituent R z They can be arbitrarily connected to form a ring; Ar1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; L T It is selected from single bonds, substituted or unsubstituted alkylene groups having 1-30 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-30 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. T is selected from CR each time it appears, either the same or different. t Or N; R t 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 t They can be arbitrarily connected to form a ring.
18. An electronic device comprising an electroluminescent device as claimed in any one of claims 1-16, or a compound composition as claimed in claim 17.
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