Organic electroluminescent material and device thereof
By using a compound with a structure of Formula 1, the limitations of carrier transmission capability and lifetime of triazine-type materials in optoelectronic devices are solved, and an efficient and long-life organic electroluminescent device is achieved.
Patent Information
- Application Number
- CN202310941557.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-07-28
- Publication Date
- 2025-02-14
AI Technical Summary
The existing triazine organic semiconductor materials have limitations in carrier transmission capabilities and lifetimes in optoelectronic devices, which limit their application potential.
Compounds with a specific structure of Formula 1 are used as the main material, electron transport material or hole blocking material of the organic electroluminescent device to improve the overall performance of the device.
Low driving voltage, high device efficiency and significantly improved device life are achieved, and carrier transmission capabilities are improved.
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Figure CN119431339A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a compound having a structure of Formula 1, an organic electroluminescent device comprising the compound, and a compound composition comprising the compound. Background Art
[0002] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an aromatic amine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.
[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and VanSlyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.
[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.
[0008] Triazine organic semiconductor materials are widely used in OLEDs due to their superior photoelectric properties, redox properties, and stability.
[0009] CN114163424A discloses an organic compound having the following structure and an organic light-emitting device comprising the compound: Wherein U is selected from O, S or Se; m+n is greater than or equal to 1; R x Having a structure represented by Formula 2: Wherein L3 is independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof. In the specific compounds disclosed in the application, most of L3 is a single bond or an unsubstituted phenylene group, which shows that it does not focus on compounds with substituents on the phenylene group between triazine and carbazole. The application does not disclose or teach the effect of the change of the substitution position of the phenyl group on the phenylene group connected to the triazine on the device performance, and does not disclose or teach the unexpected unique advantages of the compound in which the phenyl group substituted on the phenylene group connected to the triazine is in the para position.
[0010] KR20220070148A discloses an organic compound having the following structure and an organic light-emitting device comprising the compound: Where n+m+l≥1, and Donor1 to Donor3 are mutually independent carbazole derivatives. The compound of the application contains at least three carbazole groups and at least one cyano group. In the specific compounds disclosed, the connecting groups connecting triazine and carbazole are mostly phenylene, pyridylene or pyrimidylene, etc., and only one compound is disclosed in which the connecting group between triazine and carbazole is biphenylene: However, the biphenylene linking group between the carbazole group and the triazine in the compound is also substituted with a cyano group. The application does not disclose or teach a compound without a cyano group on the biphenylene linking group between the carbazole group and the triazine and its application in an organic electroluminescent device. In addition, the application focuses on the application of the compound as a delayed fluorescence luminescent material in an electroluminescent device, and does not disclose or teach the effect of the compound as other materials (such as a host material) on the device performance.
[0011] However, the triazine organic semiconductor materials reported so far have certain limitations in carrier transport capacity and lifetime in optoelectronic devices. Therefore, the application potential of this type of material deserves further in-depth research and development. Summary of the invention
[0012] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least part of the above problems. The compounds can be applied to organic electroluminescent devices and can improve the comprehensive performance of the devices, such as having low driving voltage, high device efficiency, and significantly improved device life.
[0013] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:
[0014]
[0015] in,
[0016] U is selected from O, S or Se;
[0017] X1-X2 are selected from CR in the same or different ways each time they appear x or N, X3-X4 are each independently selected from C, CR x or N, and one of X3 and X4 is selected from C and connected to Cz;
[0018] Cz has a structure represented by Formula 1-1:
[0019] Y1-Y5 are selected from CR y or N;
[0020] Each time Z1-Z8 appears, they are selected from CR in the same or different way. z or N;
[0021] a is an integer selected from 1 to 7;
[0022] Each occurrence of V1-V8 is selected from C, CR v or N; wherein one of V1-V4 is selected from C and connected to L1, and a of the remaining three of V1-V4 and V5-V8 is selected from C and connected to L2;
[0023] R xeach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0024] R y , R z and R v The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0025] Ar is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0026] L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0027] Adjacent substituent R x can optionally be linked to form a ring;
[0028] Adjacent substituent R y can optionally be linked to form a ring;
[0029] Adjacent substituent R z can optionally be linked to form a ring;
[0030] Adjacent substituent R v Can optionally be linked to form a ring.
[0031] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compound of formula 1 described in the above embodiment.
[0032] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the compound of formula 1 described in the above embodiment.
[0033] The present invention discloses a series of compounds having the structure of Formula 1. The compounds can be used as host materials, electron transport materials or hole blocking materials in organic electroluminescent devices, and can improve the comprehensive performance of the devices, such as low driving voltage, high device efficiency, and significantly improved device life. BRIEF DESCRIPTION OF THE DRAWINGS
[0034] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.
[0035] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION
[0036] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.
[0037] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.
[0038] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.
[0039] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
[0040] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0041] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.
[0042] The materials and structures described herein may also be used in other organic electronic devices listed above.
[0043] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.
[0044] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0045] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
[0046] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0047] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.
[0048] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).
[0049] Definition of Substituent Terms
[0050] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.
[0051] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
[0052] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.
[0053] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbons in an alkyl chain substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl may be optionally substituted.
[0054] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.
[0055] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.
[0056] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl. In addition, the aryl group may be optionally substituted.
[0057] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.
[0058] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.
[0059] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.
[0060] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.
[0061] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,
[0062] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.
[0063] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.
[0064] Alkylgermanyl - As used herein, alkyl substituted germanyl is contemplated. The alkylgermanyl may be an alkylgermanyl having 3-20 carbon atoms, preferably an alkylgermanyl having 3 to 10 carbon atoms. Examples of alkylgermanyl include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyltert-butylgermanyl, methyldi-tert-butylgermanyl. In addition, the alkylgermanyl may be optionally substituted.
[0065] Arylgermanyl - as used herein, encompasses germanyl substituted with at least one aryl or heteroaryl group. The arylgermanyl may be an arylgermanyl having 6 to 30 carbon atoms, preferably an arylgermanyl having 8 to 20 carbon atoms. Examples of arylgermanyl include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyltert-butylgermanyl. In addition, the arylgermanyl may be optionally substituted.
[0066] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.
[0067] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, Substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups refer to any one of alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylgermanyl groups, arylgermanyl groups, amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, sulfinyl groups, sulfonyl groups and phosphino groups, which may be substituted by one or more of deuterium, halogen groups, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted alkyl groups having 1 to 20 carbon atoms, Cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms , unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.
[0068] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.
[0069] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
[0070] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.
[0071] In the compounds mentioned in the present disclosure, unless clearly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0073]
[0074] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0075]
[0076] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to a further distant carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
[0077]
[0078] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
[0079]
[0080] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:
[0081]
[0082] in,
[0083] U is selected from O, S or Se;
[0084] X1-X2 are selected from CR in the same or different ways each time they appear x or N, X3-X4 are each independently selected from C, CR x or N, and one of X3 and X4 is selected from C and is connected to Cz shown in Formula 1;
[0085] Cz has a structure represented by Formula 1-1:
[0086] Y1-Y5 are selected from CR y or N;
[0087] Each time Z1-Z8 appears, they are selected from CR in the same or different way. z or N;
[0088] a is an integer selected from 1 to 7;
[0089] Each occurrence of V1-V8 is selected from C, CR v or N; wherein one of V1-V4 is selected from C and connected to L1, and a of the remaining three of V1-V4 and V5-V8 is selected from C and connected to L2;
[0090] R xeach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0091] R y , R z and R v The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0092] Ar is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
[0093] L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
[0094] Adjacent substituent R x can optionally be linked to form a ring;
[0095] Adjacent substituent R y can optionally be linked to form a ring;
[0096] Adjacent substituent R z can optionally be linked to form a ring;
[0097] Adjacent substituent R v Can optionally be linked to form a ring.
[0098] In this context, “the adjacent substituent R x "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R x can be connected to form a ring, for example, any two adjacent substituents R x can be connected to form a ring with 6-24 ring atoms, or any two adjacent substituents R x can be connected to form a ring with 6-12 ring atoms, or any two adjacent substituents R x can be connected to form a six-membered ring. Obviously, any adjacent R x They can also not be connected to form a ring.
[0099] In this context, “the adjacent substituent R y "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R y can be connected to form a ring, for example, any two adjacent substituents R y can be connected to form a ring with 6-24 ring atoms, or any two adjacent substituents R y can be connected to form a ring with 6-12 ring atoms, or any two adjacent substituents R y can be connected to form a six-membered ring. Obviously, any adjacent R y They can also not be connected to form a ring.
[0100] In this context, “the adjacent substituent R z "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R z can be connected to form a ring, for example, any two adjacent substituents R z can be connected to form a ring with 6-24 ring atoms, or any two adjacent substituents R z can be connected to form a ring with 6-12 ring atoms, or any two adjacent substituents R z can be connected to form a six-membered ring. Obviously, any adjacent R z They can also not be connected to form a ring.
[0101] In this context, “the adjacent substituent R v "can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R v can be connected to form a ring, for example, any two adjacent substituents R v can be connected to form a ring with 6-24 ring atoms, or any two adjacent substituents R v can be connected to form a ring with 6-12 ring atoms, or any two adjacent substituents R v can be connected to form a six-membered ring. Obviously, any adjacent R v They can also not be connected to form a ring.
[0102] In Formula 1, V1-V8 are selected from C, CR v or N; wherein one of V1-V4 is selected from C and connected to L1, and a of the remaining three of V1-V4 and V5-V8 is selected from C and each is connected to L2. For example, when a is 1, one of V1-V4 is selected from C and connected to L1, and one of the remaining three of V1-V4 and V5-V8 is selected from C and connected to L2. For example, when a is 2, there are 2 L2 in the compound of formula 1, one of V1-V4 is selected from C and connected to L1, and 2 of the remaining three of V1-V4 and V5-V8 are selected from C and connected to 2 L2 respectively. For example, for compound A-105 For example, V3 is selected from C and connected to L1 (in this case, a single bond), a is 1, and V8 is selected from C and connected to L2 (in this case, a phenylene group).
[0103] In Formula 1, one of X3 and X4 is selected from C and connected to Cz. That is, X3 is selected from C and connected to Cz shown in Formula 1, or X4 is selected from C and connected to Cz shown in Formula 1.
[0104] According to one embodiment of the present invention, the compound of the structure of Formula 1 contains only one carbazole structure or azacarbazole structure or carbazole fused ring structure or azacarbazole fused ring structure. The carbazole structure or azacarbazole structure or carbazole fused ring structure or azacarbazole fused ring structure is shown in the structure of Formula 1, that is, Cz shown in the structure of Formula 1.
[0105] According to one embodiment of the present invention, wherein said R x , R y , R z , R v , L1, L2 and Ar do not contain a carbazole structure, an azacarbazole structure, a carbazole condensed ring structure or an azacarbazole condensed ring structure.
[0106] According to one embodiment of the present invention, wherein said R x The carbazole structure, the azacarbazole structure, the carbazole condensed ring structure, or the azacarbazole condensed ring structure is not contained.
[0107] According to one embodiment of the present invention, wherein said R v The carbazole structure, the azacarbazole structure, the carbazole condensed ring structure, or the azacarbazole condensed ring structure is not contained.
[0108] According to an embodiment of the present invention, L1 does not contain a carbazole structure, an azacarbazole structure, a carbazole condensed ring structure, or an azacarbazole condensed ring structure.
[0109] According to an embodiment of the present invention, Ar does not contain a carbazole structure, an azacarbazole structure, a carbazole condensed ring structure, or an azacarbazole condensed ring structure.
[0110] According to one embodiment of the present invention, the U is selected from O or S.
[0111] According to one embodiment of the present invention, wherein said U is selected from O.
[0112] According to one embodiment of the present invention, each time Z1-Z8 appears, it is selected from CR z .
[0113] According to one embodiment of the present invention, each occurrence of Y1-Y5 is identical or different and is selected from CR y .
[0114] According to one embodiment of the present invention, each occurrence of X1-X2 is identically or differently selected from CR x , X3-X4 are each independently selected from C or CR x , and one of X3 and X4 is selected from C and connected to Cz.
[0115] According to one embodiment of the present invention, each time V1-V8 appears, it is selected from C or CR in the same or different manner. v .
[0116] According to one embodiment of the present invention, wherein L1, L2 each time appear, are identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.
[0117] According to one embodiment of the present invention, wherein L1 and L2 are identically or differently selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms each time they appear.
[0118] According to one embodiment of the present invention, wherein said L1 is selected from a single bond.
[0119] According to one embodiment of the present invention, wherein the L2 is selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
[0120] According to one embodiment of the present invention, each time L1 and L2 appear, they are identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, or a combination thereof.
[0121] According to one embodiment of the present invention, L1 and L2 are selected from a single bond or a phenylene group the same or different when they appear each time.
[0122] According to one embodiment of the present invention, the L2 is selected from phenylene.
[0123] According to one embodiment of the present invention, wherein said R x , R y , R z and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; wherein the adjacent substituents R x can be optionally linked to form a ring, with adjacent substituents R y can be optionally linked to form a ring, with adjacent substituents R z can be optionally linked to form a ring, with adjacent substituents R v Can optionally be linked to form a ring.
[0124] According to one embodiment of the present invention, wherein said R x , R y , R z and R v The group consisting of hydrogen, deuterium, 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, and combinations thereof is selected at each occurrence, either identically or differently.
[0125] According to one embodiment of the present invention, each occurrence of Ar is identically or differently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.
[0126] According to one embodiment of the present invention, each time Ar appears, it is identically or differently selected from the following 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 carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridyl, and combinations thereof.
[0127] According to one embodiment of the present invention, wherein a is selected from 1, 2, 3 or 4, a among V5-V8 is selected from C and connected to L2.
[0128] According to one embodiment of the present invention, one of V1-V4 is selected from C and connected to L1, a is 1, and one of V5-V8 is selected from C and connected to L2.
[0129] According to one embodiment of the present invention, wherein the V3 is selected from C and connected to the L1, a is 1, and the V8 is selected from C and connected to the L2.
[0130] According to one embodiment of the present invention, wherein U is O, one of V1-V4 is selected from C and connected to L1.
[0131] According to one embodiment of the present invention, wherein U is S, V4 is selected from C and connected to L1.
[0132] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-852, and the specific structures of Compound A-1 to Compound A-852 are shown in Claim 9.
[0133] According to one embodiment of the present invention, hydrogen in Compound A-1 to Compound A-852 can be partially or completely replaced by deuterium.
[0134] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising:
[0135] anode,
[0136] cathode,
[0137] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula 1, and the specific structure of the compound having a structure of Formula 1 is shown in any of the above embodiments.
[0138] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a host compound.
[0139] According to one embodiment of the present invention, the organic layer is an electron transport layer, and the compound is an electron transport compound.
[0140] According to one embodiment of the present invention, the organic layer is a hole blocking layer, and the compound is a hole blocking compound.
[0141] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the compound is a main compound, and the light-emitting layer further comprises a second main compound, wherein the second main compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylate, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
[0142] According to one embodiment of the present invention, the second host compound comprises at least one chemical group selected from the group consisting of benzene, carbazole, indolecarbazole, fluorene, silylfluorene, and combinations thereof.
[0143] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 2 or Formula 3:
[0144]
[0145] in,
[0146] Each occurrence of T is selected from C, CR t or N;
[0147] G is selected, identically or differently, from C(R g )2. NRg , O or S; when multiple R g When multiple R g Same or different;
[0148] L T Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0149] R t , R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0150] Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof;
[0151] Adjacent substituent R t , R g Can optionally be linked to form a ring.
[0152] In this context, “the adjacent substituent R t , R g "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R t Between the two substituents R g Between, the substituent Rt and R g Any one or more of these adjacent substituent groups may be connected to form a ring. Obviously, none of these substituents may be connected to form a ring.
[0153] According to one embodiment of the present invention, the second host compound has a structure represented by one of Formula 2-a to Formula 2-j, Formula 3-a to Formula 3-f:
[0154]
[0155]
[0156] in,
[0157] Each occurrence of T is selected from CR t or N;
[0158] G is selected, identically or differently, from C(R g )2, NR g , O or S;
[0159] L T Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
[0160] Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof;
[0161] R t and R gEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
[0162] Adjacent substituent R t , R g Can optionally be linked to form a ring.
[0163] According to one embodiment of the present invention, in Formula 2-a to Formula 2-j, Formula 3-a to Formula 3-f, T is selected from CR the same or different each time it appears. t .
[0164] According to one embodiment of the present invention, in Formula 2-a to Formula 2-j, Formula 3-a to Formula 3-f, T is selected from CR the same or different each time it appears. t Or N, and at least one T is selected from N, for example, one T or two Ts are selected from N.
[0165] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compound PH-1 to compound PH-114:
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177] According to one embodiment of the present invention, the organic layer is a light-emitting layer, the compound is a host compound; the light-emitting layer further comprises a first metal complex having M(L a ) m (L b ) n (L c ) q The general formula of
[0178] The metal M is selected from metals with a relative atomic mass greater than 40;
[0179] L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the metal M, respectively, and the ligand L a , L b , L c Can be the same or different;
[0180] Ligand L a , L b , L c can optionally be linked to form a multidentate ligand;
[0181] m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c Can be the same or different;
[0182] Ligand L a It has a structure represented by formula 4:
[0183]
[0184] Ring C1 and Ring C2 are identically or differently selected at each occurrence from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
[0185] Q1 and Q2 are selected from C or N at each occurrence, identically or differently;
[0186] A1 and A2 are selected, identically or differently, at each occurrence from a single bond, O or S;
[0187] L 11 Each occurrence is identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 5 to 30 carbon atoms, and combinations thereof; when two R' are present at the same time, the two R's are identical or different;
[0188] R 11 and R 12 Each occurrence of the same or different means mono-, poly- or no-substitution;
[0189] R', R 11 and R 12 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0190] The adjacent substituents R', R 11 and R 12 can optionally be linked to form a ring;
[0191] Ligand L b and L cEach occurrence is identically or differently selected from monoanionic bidentate ligands.
[0192] In this embodiment, "the adjacent substituents R', R 11 and R 12 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, adjacent substituents R', adjacent substituents R 11 Between adjacent substituents R 12 Between, and adjacent substituents R 11 and R 12 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0193] According to one embodiment of the present invention, the ligand L b and L c Each occurrence is identically or differently selected from the group consisting of:
[0194]
[0195] in,
[0196] R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0197] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;
[0198] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;
[0199] R a , R b , R c , R N1 , R N2 , R C1 and R C2The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0200] Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
[0201] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and RC1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be linked to form a ring. For example, The adjacent substituent R a , R b Can be optionally linked to form a ring, which can form one or more of the following structures including but not limited to:
[0202] or Wherein W is selected from O, S, Se, NR w or CR w R w ; wherein said R w , R a ', R b ' is defined in the same way as R a Obviously, these substituents may not be connected to form a ring.
[0203] According to one embodiment of the present invention, the first metal complex has Ir(L a ) m (L b ) 3-m The general structure of the formula 4-1 is:
[0204]
[0205] in,
[0206] m is 0, 1, 2 or 3; when m is 2 or 3, multiple L a The same or different; when m is 0 or 1, multiple L b Same or different;
[0207] Each occurrence of T1-T6 is the same or different selection from CR T or N;
[0208] R a , R b and R d Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;
[0209] R a , R b , R d and R T The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
[0210] Adjacent substituent R a , R b can optionally be linked to form a ring;
[0211] Adjacent substituent R d , R T Can optionally be linked to form a ring.
[0212] In this embodiment, "the adjacent substituent R a , R b "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between, and the substituent R a and R b Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0213] In this embodiment, "the adjacent substituent R d , R T "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R T Between the two substituents Rd Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.
[0214] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T , and the R T is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0215] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T , and the R T Selected from fluorine or cyano.
[0216] 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 is selected from fluorine or cyano, the other R T The group is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0217] According to one embodiment of the present invention, each occurrence of T1-T6 is the same or different selection from CR T .
[0218] According to one embodiment of the present invention, each time T1-T6 appears, it is selected from CR 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.
[0219] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compound GD1 to compound GD76:
[0220]
[0221]
[0222]
[0223]
[0224]
[0225] According to one embodiment of the present invention, hydrogen in the compounds GD1 to GD76 can be partially or completely replaced by deuterium.
[0226] According to an embodiment of the present invention, the organic electroluminescent device emits green light.
[0227] According to an embodiment of the present invention, the organic electroluminescent device emits white light.
[0228] According to one embodiment of the present invention, a compound composition is also disclosed, which comprises a compound represented by Formula 1; the compound is shown in any of the aforementioned embodiments.
[0229] Combination with other materials
[0230] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0231] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of luminescent dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.
[0232] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.
[0233] Material synthesis example:
[0234] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:
[0235] Synthesis Example 1: Synthesis of Compound A-105
[0236] Step 1: Synthesis of Intermediate C
[0237]
[0238] In a three-necked round-bottom flask, add intermediate A (22.2g, 106.0mmol), intermediate B (17.7g, 106.0mmol), cesium carbonate (Cs2CO3, 69.1g, 212.0mmol) and 200mL N,N-dimethylformamide (DMF) in sequence. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. Pour the reaction solution into a large amount of water, add ethyl acetate for extraction, collect the organic phase, and concentrate under reduced pressure to obtain a crude product. The crude product is slurried with anhydrous ethanol to obtain a white solid intermediate C (26.7g, 74.9mmol) with a yield of 70.7%.
[0239] Step 2: Synthesis of Intermediate E
[0240]
[0241] In a three-necked round-bottom flask, add intermediate C (18.9 g, 53.0 mmol), intermediate D (9.5 g, 77.9 mmol), Pd (PPh3) 4 (2.4 g, 2.1 mmol), K2CO3 (14.6 g, 106.0 mmol), 160 mL of toluene, 40 mL of EtOH and 40 mL of H2O. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution was separated, the aqueous phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 10:1 to 8:1) to obtain a white solid intermediate E (16.8 g, 47.5 mmol) with a yield of 89.6%.
[0242] Step 3: Synthesis of Intermediate F
[0243]
[0244] In a three-necked round-bottom flask, add intermediate E (16.8 g, 47.5 mmol), biboric acid pinacol ester (18.1 g, 71.3 mmol), Pd2(dba)3 (0.87 g, 0.95 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3·HBF4, 0.87 g, 0.95 mmol), potassium acetate (KOAc, 9.3 g, 95.0 mmol) and 150 mL 1,4-dioxane. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction system is filtered through diatomaceous earth, and the filtrate is concentrated under reduced pressure to obtain a crude product. The crude product is purified by silica gel column chromatography (PE / DCM=5:1 to 2:1) to obtain a white solid intermediate F (18.0 g, 40.4 mmol) with a yield of 85.0%.
[0245] Step 4: Synthesis of Intermediate H
[0246]
[0247] In a three-necked round-bottom flask, add intermediate F (17.8 g, 40.0 mmol), intermediate G (11.8 g, 52.0 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and Na2CO3 (8.48 g, 80.0 mmol) to a mixed solvent of THF (256 mL) and H2O (64 mL). Under N2 protection, heat to reflux. After 7 h, confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution was separated, the aqueous phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM=6:1 to 3:1) to obtain a yellow solid intermediate H (12.4 g, 24.4 mmol) with a yield of 60.9%.
[0248] Step 5: Synthesis of Intermediate K
[0249]
[0250] In a three-necked round-bottom flask, add intermediate I (7.0 g, 20.0 mmol), intermediate J (3.5 g, 24.0 mmol), Pd(PPh3)4 (0.693 g, 0.6 mmol), K2CO3 (9.5 g, 68.7 mmol) to a mixed solvent of 1,4-dioxane (100 mL) and H2O (25 mL). Under nitrogen protection, heat and reflux overnight. After the reaction is completed, stop heating and cool to room temperature. Separate the reaction solution, extract the aqueous phase with DCM, and combine the organic phases. Dry the organic phase with anhydrous Na2SO4, filter, and concentrate under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to obtain a white solid intermediate K (5.9 g, 19.4 mmol) with a yield of 97.0%.
[0251] Step 6: Synthesis of Intermediate L
[0252]
[0253] In a three-necked round-bottom flask, intermediate K (5.9 g, 19.4 mmol), biboronic acid pinacol ester (7.4 g, 29.1 mmol), Pd(OAc)2 (0.22 g, 0.97 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 0.93 g, 1.94 mmol), potassium acetate (KOAc, 4.75 g, 48.5 mmol) were added to 1,4-dioxane (100 mL). Under nitrogen protection, the mixture was heated to reflux overnight. After the reaction was completed, heating was stopped and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth to obtain a filtrate, which was concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (PE / DCM = 5:1 to 1:1) to obtain a white solid intermediate L (5.3 g, 13.4 mmol) with a yield of 69.1%.
[0254] Step 7: Synthesis of Compound A-105
[0255]
[0256] In a three-necked round-bottom flask, add intermediate L (3.95g, 10.0mmol), intermediate H (5.09g, 10.0mmol), Pd(PPh3)4 (0.23g, 0.2mmol), K2CO3 (2.76g, 20.0mmol) to a mixed solvent of toluene (40mL), EtOH (10mL), and H2O (10mL). Under nitrogen protection, heat and reflux overnight. After the reaction is completed, stop heating, cool to room temperature, filter the reaction solution under reduced pressure, and rinse the obtained solid with water and methanol in turn. The crude product was purified by column chromatography (PE / DCM=10:1 to 2:1) to obtain a light yellow solid (4.66g, 6.28mmol) with a yield of 62.8%. The product was confirmed to be the target product A-105 with a molecular weight of 741.3.
[0257] Synthesis Example 2: Synthesis of Compound A-126
[0258] Step 1: Synthesis of Intermediate N
[0259]
[0260] In a three-necked round-bottom flask, add intermediate I (7.0 g, 20.0 mmol), intermediate M (3.5 g, 24.0 mmol), Pd(PPh3)4 (0.693 g, 0.6 mmol), K2CO3 (9.5 g, 68.7 mmol) to a mixed solvent of 1,4-dioxane (100 mL) and H2O (25 mL), and heat under reflux overnight under nitrogen protection. After the reaction is completed, stop heating and cool to room temperature. Separate the reaction solution, extract the aqueous phase with DCM, and combine the organic phases. Dry the organic phase over anhydrous Na2SO4, filter, and concentrate under reduced pressure to obtain a crude product. The crude product is purified by column chromatography (PE / DCM=10:1 to 3:1) to obtain a white solid intermediate N (5.9 g, 19.4 mmol) with a yield of 97.0%.
[0261] Step 2: Synthesis of intermediate O
[0262]
[0263] In a three-necked round-bottom flask, intermediate N (5.9 g, 19.4 mmol), biboronic acid pinacol ester (7.4 g, 29.1 mmol), Pd(OAc)2 (0.22 g, 0.97 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 0.93 g, 1.94 mmol), potassium acetate (KOAc, 4.75 g, 48.5 mmol) were added to 1,4-dioxane (100 mL). Under nitrogen protection, the mixture was heated to reflux overnight. After the reaction was completed, heating was stopped and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth to obtain a filtrate, which was concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (PE / DCM = 5:1 to 1:1) to obtain a white solid intermediate O (5.3 g, 13.4 mmol) with a yield of 69.1%.
[0264] Step 3: Synthesis of Compound A-126
[0265]
[0266] In a three-necked round-bottom flask, add intermediate O (3.95g, 10.0mmol), intermediate H (5.09g, 10.0mmol), Pd(PPh3)4 (0.23g, 0.2mmol), K2CO3 (2.76g, 20.0mmol) to a mixed solvent of toluene (40mL), EtOH (10mL), and H2O (10mL). Under nitrogen protection, heat and reflux overnight. After the reaction is completed, stop heating, cool to room temperature, filter under reduced pressure, and rinse the obtained solid with water and methanol in turn to obtain a crude product. The crude product is purified by column chromatography (PE / DCM=10:1 to 2:1) to obtain a light yellow solid (4.86g, 6.55mmol) with a yield of 65.5%. The product is confirmed to be the target product A-126 with a molecular weight of 741.3.
[0267] Synthesis Example 3: Synthesis of Compound A-611
[0268] Step 1: Synthesis of Intermediate Q
[0269]
[0270] In a three-necked round-bottom flask, add intermediate P (60.0 g, 199.4 mmol), intermediate D (29.2 g, 239.2 mmol), Pd (PPh3) 4 (2.3 g, 2.0 mmol), K2CO3 (55.0 g, 398.8 mmol), 400 mL toluene, 100 mL EtOH and 100 mL H2O in sequence. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is separated, the aqueous phase is extracted with DCM, and the organic phases are combined. The organic phase is dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain a crude product. The crude product is purified by silica gel column chromatography (PE) to obtain a colorless oily intermediate Q (47.3 g, 188.4 mmol) with a yield of 94.5%.
[0271] Step 2: Synthesis of intermediate R
[0272]
[0273] In a three-necked round-bottom flask, add intermediate Q (47.3 g, 188.4 mmol), diboronic acid pinacol ester (62.2 g, 244.9 mmol), Pd(dppf)Cl2 (2.8 g, 3.77 mmol), KOAc (37.0 g, 376.8 mmol) and 600 mL 1,4-dioxane. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction system is filtered through diatomaceous earth to obtain a filtrate, and the filtrate is concentrated under reduced pressure to obtain a crude product. The crude product is purified by silica gel column chromatography (PE / DCM=5:1 to 2:1) to obtain a white solid intermediate R (46.0 g, 154.3 mmol) with a yield of 81.9%.
[0274] Step 3: Synthesis of Intermediate S
[0275]
[0276] In a three-necked round-bottom flask, add intermediate R (20.9g, 70.0mmol), intermediate G (20.6g, 91.0mmol), Pd(PPh3)4 (0.8g, 0.7mmol), Na2CO3 (14.8g, 140.0mmol), 280mL THF and 70mL H2O in sequence. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution was separated, the aqueous phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM=10:1 to 8:1) to obtain a white solid intermediate S (22.0g, 60.8mmol) with a yield of 86.9%.
[0277] Step 4: Synthesis of intermediate T
[0278]
[0279] In a three-necked round-bottom flask, add intermediate S (2.9 g, 8.0 mmol), intermediate O (3.2 g, 8.0 mmol), Pd (PPh3) 4 (0.19 g, 0.16 mmol), K2CO3 (2.2 g, 16.0 mmol), 40 mL toluene, 10 mL EtOH and 10 mL H2O in sequence. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. A large amount of solid precipitated in the reaction solution, filtered, and the obtained solid was washed with water and ethanol in turn to obtain a crude product. The crude product was recrystallized from toluene and washed with ethanol to obtain a white solid intermediate T (4.6 g, 7.7 mmol) with a yield of 96.3%.
[0280] Step 5: Synthesis of Compound A-611
[0281]
[0282] In a three-necked round-bottom flask, add intermediate T (4.6g, 7.7mmol), intermediate B (1.54g, 9.24mmol), cesium carbonate (5.02g, 15.4mmol) and 50mL DMF in sequence. Under N2 protection, heat and reflux overnight. Confirm the end of the reaction by TLC, stop heating, and cool to room temperature. Pour the reaction solution into a large amount of water, precipitate a large amount of solid, and filter under reduced pressure to obtain a crude product. The crude product is purified by silica gel column chromatography (PE / DCM=10:1 to 3:1) to obtain a light yellow solid (3.2g, 4.3mmol), with a yield of 55.8%. The product is confirmed to be the target product A-611, with a molecular weight of 741.3.
[0283] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0284] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiment is only an example and should not be construed as limiting. A person skilled in the art can reasonably improve the preparation method of the following embodiment based on the prior art. For example, the ratio of various materials in the light-emitting layer is not particularly limited. A person skilled in the art can reasonably select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer material, 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%. In addition, the main material can be one or two materials, and 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.
[0285] Device Embodiment
[0286] Device Example 1
[0287] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8Compound HT and compound HT1 were co-deposited as a hole injection layer (HIL, weight ratio 97:3) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound PH-23 was used as an electron blocking layer (EBL) with a thickness of Then, compound GD2 was doped into compound PH-23 and compound A-105 of the present invention, and co-evaporated to form an emitting layer (EML, weight ratio 6:56:38) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, weight ratio 40:60) with a thickness of Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) was evaporated as an electron injection layer, and 120 nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
[0288] Device Example 2
[0289] The preparation method of device example 2 is the same as that of device example 1, except that the present compound A-126 is used in the light emitting layer (EML) instead of the present compound A-105.
[0290] Device Example 3
[0291] The preparation method of device example 3 is the same as that of device example 1, except that the compound A-611 of the present invention is used in the light emitting layer (EML) instead of the compound A-105 of the present invention.
[0292] Device Comparison Example 1
[0293] The preparation method of device comparative example 1 is the same as that of device example 1, except that compound C-1 is used in the light emitting layer (EML) instead of compound A-105 of the present invention.
[0294] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.
[0295] Table 1 Partial device structures of device embodiments 1 to 3 and comparative example 1
[0296]
[0297]
[0298] The structure of the materials used in the device is shown below:
[0299]
[0300] Table 2 shows that at 15 mA / cm 2 The CIE data, driving voltage, external quantum efficiency (EQE), current efficiency (CE) and power efficiency (PE) of Examples 1-3 and Comparative Example 1 were measured at a constant current density; and at 80 mA / cm 2 Device lifetime measured at constant current density (LT97).
[0301] Table 2 Device data of Examples 1 to 3 and Comparative Example 1
[0302]
[0303] As can be seen from the data in Table 2, the voltage of Comparative Example 1 is at a low voltage level, while Example 1 is also at a low voltage level like Comparative Example 1, and compared with Comparative Example 1, the EQE of Example 1 is increased by 4.0%, the CE is increased by 4.2%, and the PE is increased by 4.8%. More importantly, the device life is unexpectedly greatly increased by 15.3 times. The structural difference between Example 1 and Comparative Example 1 is only the difference in the position of the phenyl substitution on the phenylene connected between the carbazole group and the triazine fragment in the main compound. The phenyl substituent on the phenylene connected to triazine in the present compound A-105 is in the para position with the triazine, while the phenyl substituent on the phenylene connected to triazine in the comparative compound C-1 is in the meta position with the triazine. This shows that compared with the compounds in the prior art where the phenyl substituent on the phenylene connected to triazine is connected to the triazine in the meta position, the compound having a specific structure of Formula 1 of the present invention can maintain low voltage and improve device efficiency when applied to electroluminescent devices, especially can achieve unexpected and significant improvement in device life, and can improve the overall performance of the device.
[0304] In addition, the compound A-126 and the compound A-611 of the present invention are used in Example 2 and Example 3, respectively. As in Example 1, Example 2 and Example 3 also have low driving voltage, high device efficiency (EQE, CE, PE) and unexpectedly greatly improved device life. The excellent performance and unique advantages of the compound having a structure represented by the specific formula 1 of the present invention are once again demonstrated.
[0305] In summary, the compounds of the present invention are applied to organic electroluminescent devices, which can improve the comprehensive performance of the devices, especially can greatly increase the life of the devices, and have broad application prospects.
[0306] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.
Claims
1. A compound having a structure of Formula 1: in, U is selected from O, S or Se; X1-X2 are selected from CR in the same or different ways each time they appear x or N, X3-X4 are each independently selected from C, CR x or N, and one of X3 and X4 is selected from C and connected to Cz; Cz has a structure represented by Formula 1-1: Y1-Y5 are selected from CR y or N; Each time Z1-Z8 appears, they are selected from CR in the same or different way. z or N; a is an integer selected from 1 to 7; Each occurrence of V1-V8 is selected from C, CR v or N; wherein one of V1-V4 is selected from C and connected to L1, and a of the remaining three of V1-V4 and V5-V8 is selected from C and connected to L2; R x each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R y , R z and R v The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; L1 and L2 are identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituent R x can optionally be linked to form a ring; Adjacent substituent R y can optionally be linked to form a ring; Adjacent substituent R z can optionally be linked to form a ring; Adjacent substituent R v Can optionally be linked to form a ring.
2. The compound of claim 1, wherein said U is selected from O or S; preferably, said U is selected from O.
3. The compound of claim 1, wherein each occurrence of Z1-Z8 is identically or differently selected from CR z ; and / or Y1-Y5 are selected from CR y .
4. The compound of claim 1, wherein each occurrence of X1-X2 is identically or differently selected from CR x , X3-X4 are each independently selected from C or CR x , and one of X3 and X4 is selected from C and connected to Cz; and / or V1-V8 is selected from C or CR each time it appears, either identically or differently v .
5. The compound of claim 1, wherein each occurrence of L1, L2 is identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Preferably, L1, L2 are identically or differently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted pyridylene, or a combination thereof at each occurrence; More preferably, L1, L2 are identically or differently selected from a single bond, or a substituted or unsubstituted phenylene group at each occurrence.
6. The compound of any one of claims 1 to 5, wherein R x , R y , R z and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof; wherein the adjacent substituents R x can be optionally linked to form a ring, with adjacent substituents R y can be optionally linked to form a ring, with adjacent substituents R z can be optionally linked to form a ring, with adjacent substituents R v can optionally be linked to form a ring; Preferably, R x , R y , R z and R v The group consisting of hydrogen, deuterium, 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, and combinations thereof is selected at each occurrence, either identically or differently.
7. The compound according to any one of claims 1 to 6, wherein Ar is selected from, at each occurrence, the same or different, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, or a combination thereof; Preferably, Ar is selected from the group consisting of 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, and combinations thereof, at each occurrence, the same or different.
8. The compound of claim 1, wherein one of V1-V4 is selected from C and is connected to L1, a is 1, and one of V5-V8 is selected from C and is connected to L2; Preferably, wherein the V3 is selected from C and connected to the L1, a is 1, and the V8 is selected from C and connected to the L2.
9. The compound of claim 1, wherein the compound is selected from the group consisting of Compound A-1 to Compound A-852: in, Optionally, hydrogen in the compounds A-1 to A-852 can be partially or completely replaced by deuterium.
10. An organic electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 9.
11. The organic electroluminescent device as claimed in claim 10, wherein the organic layer is a light-emitting layer and the compound is a host compound; or the organic layer is an electron transport layer and the compound is an electron transport compound; or the organic layer is a hole blocking layer and the compound is a hole blocking compound.
12. The organic electroluminescent device according to claim 11, wherein the organic layer is a light-emitting layer, the compound is a host compound, the light-emitting layer further comprises a second host compound, the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof; Preferably, the second host compound comprises at least one chemical group selected from the group consisting of benzene, carbazole, indolecarbazole, fluorene, silylfluorene, and combinations thereof.
13. The organic electroluminescent device according to claim 12, wherein the second host compound has a structure represented by Formula 2 or Formula 3: in, Each occurrence of T is selected from C, CR t or N; G is selected, identically or differently, from C(R g )2. NR g , O or S; when multiple R g When multiple R g Same or different; L T Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; R t , R g Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Ar1 and Ar2 are identically or differently selected at each occurrence from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof; Adjacent substituent R t , R g Can optionally be linked to form a ring.
14. The organic electroluminescent device according to claim 11, wherein the organic layer is a light-emitting layer, the compound is a host compound, the light-emitting layer further comprises a first metal complex, and the first metal complex has M(L a ) m (L b ) n (L c ) q The general formula of The metal M is selected from metals with a relative atomic mass greater than 40; L a , L b , L c are the first ligand, the second ligand and the third ligand coordinated with the metal M, respectively, and the ligand L a , L b , L c Can be the same or different; Ligand L a , L b , L c can optionally be linked to form a multidentate ligand; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of m, n, q is equal to the oxidation state of metal M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c Can be the same or different; Ligand L a It has a structure represented by formula 4: Ring C1 and Ring C2 are identically or differently selected at each occurrence from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; Q1 and Q2 are selected from C or N at each occurrence, identically or differently; A1 and A2 are selected, identically or differently, at each occurrence from a single bond, O or S; L 11 Each occurrence is identically or differently selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 5 to 30 carbon atoms, and combinations thereof; when two R' are present at the same time, the two R's are identical or different; R 11 and R 12 Each occurrence of the same or different means mono-, poly- or no-substitution; R', R 11 and R 12 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The adjacent substituents R', R 11 and R 12 can optionally be linked to form a ring; Ligand L b and L c are selected, identically or differently at each occurrence, from monoanionic bidentate ligands; Preferably, the ligand L b and L c Each occurrence is identically or differently selected from the group consisting of: in, R a and R b Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 The group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.
15. A compound composition comprising the compound according to any one of claims 1 to 9.
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