Organic electroluminescent compound and use thereof

Abstract

This invention provides a compound and its applications. The compound of this invention has a structure represented by H-L-E, wherein H has the structure shown in Formula 1 or Formula 2. The compound of this invention can be used as the host material of the light-emitting layer in organic electroluminescent devices, exhibiting significantly reduced evaporation temperature, better thermal stability, effectively reduced energy consumption, improved device efficiency, and reduced device driving voltage.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to an organic electroluminescent compound, an organic electroluminescent device containing the compound, and applications of the compound. Background Technology

[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (COPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LEGS), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline aluminum layer as both an electron transport layer and a light-emitting layer. Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and Van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gaps, making it possible for excitons to return from the doublet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing. Various OLED manufacturing methods exist. Small-molecule OLEDs are typically manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods such as spin coating, inkjet printing, and nozzle printing. Small-molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0006] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0007] Currently reported main materials still have room for improvement. To meet the industry's ever-increasing demands, especially for higher device efficiency, longer device lifespan, and lower drive voltage, new materials still require further research and development. Summary of the Invention

[0008] The purpose of this invention is to provide a series of nitrogen-containing heterocyclic compounds to solve at least some of the aforementioned problems. The compounds of this invention can be used as host materials in organic electroluminescent devices. These compounds exhibit significantly reduced evaporation temperatures, better thermal stability, and effectively reduced energy consumption, which is more beneficial for the device fabrication process. Furthermore, they can effectively improve device efficiency, reduce device drive voltage, and provide better device performance.

[0009] In a first aspect, the present invention provides an organic compound having an HLE structure, wherein H has a structure represented by Formula 1 or Formula 2:

[0010]

[0011] In Formula 1 or Formula 2, A1, A2 and A3 are selected from N or CR each time they appear, and ring A, ring B and ring C are selected from unsaturated carbon rings with 5-18 carbon atoms or unsaturated carbon heterocycles with 3-18 carbon atoms each time they appear.

[0012] R X Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0013] E has a structure represented by Equation 3:

[0014]

[0015] In Formula 3, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, either identically or differently; and when Ar1 and Ar2 are selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, Ar1 and Ar2 have a substituent R. Ar ;R Ar The same or different occurrences each time indicate single or multiple substitution;

[0016] Z1 to Z3 are each independently selected from N or CR Z And at least one of Z1 to Z3 is N;

[0017] L has a structure represented by Equation 4:

[0018] In Formula 4, ring D is selected from aryl groups having 6-30 carbon atoms or heteroaryl groups having 3-30 carbon atoms;

[0019]

[0020] R n Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0021] L1 is selected from a single bond, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof; and when L1 is selected from a substituted aryl group having 6-30 carbon atoms or a substituted heteroaryl group having 3-30 carbon atoms, L1 has a substituent R. m ;R m The same or different occurrences each time indicate single or multiple substitution;

[0022] R, R x R n R m R Z RAr Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted groups having 6-30 carbon atoms. Aryloxy groups, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0023] Adjacent substituent R x R can be arbitrarily connected to form a loop;

[0024] Adjacent substituent R n R m They can be arbitrarily connected to form a loop;

[0025] The asterisk (*) indicates the position where L and H are connected. This indicates the position where L and E are connected.

[0026] In a second aspect, the present invention also provides a luminescent material composition comprising the organic compound and dopant material described in the first aspect of the present invention.

[0027] This invention does not impose a specific limitation on the type of dopant material; any luminescent material known in the art, such as phosphorescent material, may be used as the dopant material. The dopant material described in this invention may be one or more types.

[0028] In some embodiments, the doped material is a metal complex, such as a complex of Ir, Pt, or Os.

[0029] Thirdly, the present invention provides an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises an organic compound as described in the first aspect of the present invention, or the organic layer comprises a luminescent material composition as described in the second aspect of the present invention.

[0030] The organic layer described in this invention is a light-emitting layer. Preferably, the main material of the light-emitting layer contains the organic compound described in the first aspect of this invention.

[0031] Fourthly, the present invention provides a display component comprising the electroluminescent device described in the third aspect of the present invention.

[0032] Fifthly, the present invention provides the use of the compound described in the first aspect or the composition described in the second aspect in the preparation of electroluminescent devices.

[0033] The organic compound described in the first aspect of this invention can be used as the host material of the light-emitting layer in an electroluminescent device.

[0034] Compared with existing technologies, the beneficial effects of this invention are as follows: The compounds disclosed in this invention, especially those with a bis-indole fused aza-macrocyclic structure and triazine or similar structures linked at specific positions, can be used as host materials in electroluminescent devices. The compounds of this invention have electron transport units with triazine-like structures and hole transport units with bis-indole fused aza-macrocyclic structures linked to the electron transport units at specific positions. This molecular structure design, where hole transport units and electron transport units are linked at specific positions, gives these compounds a unique spatial structure, resulting in unexpected effects. These novel compounds exhibit significantly reduced evaporation temperatures, better thermal stability, and effectively reduced energy consumption, which is more beneficial for device fabrication. Furthermore, they effectively improve device efficiency and provide better device performance. Attached Figure Description

[0035] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds disclosed herein.

[0036] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the compounds disclosed herein.

[0037] The attached figures are labeled as follows:

[0038] 100, First organic light-emitting device; 101, Substrate; 110, Anode; 120, Hole injection layer; 130, Hole transport layer; 140, Electron blocking layer; 150, Light-emitting layer; 160, Hole blocking layer; 170, Electron transport layer; 180, Electron injection layer; 190, Cathode; 102, Encapsulation layer; 200, Second organic light-emitting device. Detailed Implementation

[0039] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. The specific embodiments described herein are for illustrative purposes only and are not intended to limit the scope of the invention in any way.

[0040] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0041] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, including composite cathodes having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputtered-deposited ITO layer, are disclosed in their entirety in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. The principle and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated herein by reference in its entirety. The above-described layered structure is provided by non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0042] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise one or more layers. OLEDs also require an encapsulation layer, such as... Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference. Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) of such devices. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptops, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0043] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0044] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned furthest from the substrate. Other layers may exist between the first and second layers unless specified as being in "contact" with the second layer. For example, the cathode may be described as being "disposed" on the "anode" even if various organic layers exist between the cathode and anode. As used herein, "solution-handleable" means capable of being dissolved, dispersed, transported, and / or deposited from a liquid medium in the form of a solution or suspension.

[0045] When ligands are believed to directly contribute to the photosensitivity of the emitting material, they can be called "photosensitive." When ligands are believed not to contribute to the photosensitivity of the emitting material, they can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitizing ligands. It is believed that the internal quantum efficiency (IQE) of fluorescent OLEIs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: p-type delayed fluorescence and E-type delayed fluorescence. p-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0046] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0047] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔES-T). Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces a small ΔES-T. These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0048] Definition of the term "substituent group"

[0049] The term “halogen or halide” as used in this article includes fluorine, chlorine, bromine, and iodine.

[0050] As used herein, the term "alkyl" includes both straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isolaryl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Furthermore, the alkyl group may optionally be substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0051] As used herein, the term "alkenyl" includes a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with one or more carbon-carbon double bonds. An alkenyl group can be a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with 2-20 carbon atoms and having one or more carbon-carbon double bonds, preferably an alkenyl group with 2-12 carbon atoms, including but not limited to vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, isobutenyl, butadienyl, 1-pentenyl, 2-pentenyl, isopentenyl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl, or 1,3,5-hextrienyl, etc. Furthermore, the alkenyl group may optionally be substituted.

[0052] As used herein, the term "cycloalkyl" includes cyclic alkyl groups. A cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0053] As used herein, the term "heteroalkyl" refers to an alkyl chain in which one or more carbon atoms are substituted with heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. Heteroalkyl groups can be of 1 to 20 carbon atoms, preferably of 1 to 10 carbon atoms, and more preferably of 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminolactone, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisolactone, tert-butyldimethylsilyl, triethylsilyl, triisolactone, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisolactone. In addition, heteroalkyl groups may be optionally substituted.

[0054] The terms "carbocyclic group" and "carbocyclic" used in this article are used interchangeably to refer to non-aromatic saturated or partially unsaturated monocyclic or polycyclic systems composed of carbon atoms as ring atoms, including aromatic rings composed of carbon atoms as ring atoms. Furthermore, the carbocyclic group may be optionally substituted.

[0055] The term "heterocyclic group" as used herein is used interchangeably with "heterocycle," "carbon heterocycle," and "carbon heterocyclic group," and includes both aromatic and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-18 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacycloyl, dioxahexacycloyl, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiopyrroleyl. Furthermore, the heterocyclic group may optionally be substituted.

[0056] The term "aryl or aromatic group" as used herein includes both non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may optionally be substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0057] As used herein, the term "heteroaryl" includes non-fused and fused heteroaryl groups with 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, iso Quinoline, cyclophosphine, quinazolin, quinoxaline, naphthidine, phthalazine, pteridine, guarbenzine, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0058] As used herein, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group may optionally be substituted.

[0059] As used herein, the term "aryloxy group" is denoteed by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. An aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, aryloxy groups may optionally be substituted.

[0060] As used herein, the term "aralkyl" encompasses aryl-substituted alkyl groups. Aralkyl groups can 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-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0061] As used herein, the term "alkylsilyl or silyl" encompasses silyl groups substituted with groups listed in the above alkyl groups, such as methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, etc.

[0062] As used in this article, the term "arylsilyl" refers to a group consisting of any of the aforementioned aryl and silyl groups.

[0063] As used herein, the term "aza" in terms such as "azadibenzofuran" and "azadibenzothiophene" refers to a cyclic aromatic segment in which one or more CH groups are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0064] In this disclosure, unless otherwise defined, when any of the terms consisting of the group consisting of, for example, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alksilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphinyl, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alksilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl, which may be one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, and unsubstituted... The substituted cycloalkyl group having 3-20 carbon atoms, the unsubstituted heteroalkyl group having 1-20 carbon atoms, the unsubstituted heterocyclic group having 3-20 carbon atoms, the unsubstituted aralkyl group having 7-30 carbon atoms, the unsubstituted alkoxy group having 1-20 carbon atoms, the unsubstituted aryl group having 6-30 carbon atoms, the unsubstituted alkenyl group having 2-20 carbon atoms, the unsubstituted alkynyl group having 2-20 carbon atoms, the unsubstituted aryl group having 6-30 carbon atoms, the unsubstituted heteroaryl group having 3-30 carbon atoms, the unsubstituted alksilyl group having 3-20 carbon atoms, the unsubstituted arylsilyl group having 6-20 carbon atoms, and the unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.

[0065] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0066] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds may be preferred due to their ability to enhance device efficiency and stability. In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions in its linkage structure. The substituent present at multiple available substitution positions can be of the same structure or different structures.

[0067] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the resulting ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0068] In this invention, the statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other by chemical bonds to form a ring, as exemplified by the following formula:

[0069]

[0070] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0071]

[0072] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent bonds at the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0073]

[0074] The organic compound of the first aspect of the present invention has an HLE structure, wherein H has a structure represented by Formula 1 or Formula 2:

[0075]

[0076] Among them, A1, A2, and A3 are selected from N or CR each time they appear the same or different; ring A, ring B, and ring C are selected from unsaturated carbon rings with 5-18 carbon atoms or unsaturated heterocarbon rings with 3-18 carbon atoms each time they appear the same or different.

[0077] R XThe same or different occurrences each time indicate single substitution, multiple substitution, or no substitution.

[0078] E has a structure represented by Equation 3:

[0079]

[0080] In Formula 3, Ar1 and Ar2, each time they appear, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, either identically or differently; and when Ar1 and Ar2 are selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, Ar1 and Ar2 have a substituent R. Ar ;R Ar The same or different occurrences each time indicate single or multiple substitution;

[0081] Z1 to Z3 are each independently selected from N or CR Z And at least one of Z1 to Z3 is N;

[0082] L has a structure represented by Equation 4:

[0083] In Formula 4, ring D is selected from aryl groups having 6-30 carbon atoms or heteroaryl groups having 3-30 carbon atoms;

[0084]

[0085] R n Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0086] L1 is selected from a single bond, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof; and when L1 is selected from a substituted aryl group having 6-30 carbon atoms or a substituted heteroaryl group having 3-30 carbon atoms, L1 has a substituent R. m ;R m The same or different occurrences each time indicate single or multiple substitution;

[0087] R, R x R n R m R Z R ArEach time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted groups having 6-30 carbon atoms. Aryloxy groups, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0088] Adjacent substituent R x R can be arbitrarily connected to form a loop;

[0089] Adjacent substituent R n R m They can be arbitrarily connected to form a loop;

[0090] The asterisk (*) indicates the position where L and H are connected. This indicates the position where L and E are connected.

[0091] It should be noted that in this invention, adjacent substituents R x The fact that R can be optionally linked to form a ring can mean that adjacent substituents R can be optionally linked to form a ring, or it can mean that there are multiple R on ring A. X When, the adjacent substituent R X The elements can be arbitrarily connected to form a loop, or it can represent the presence of multiple R elements on loop B. X When, the adjacent substituent R X The elements can be arbitrarily connected to form a loop, or it can be represented that there are multiple R elements on the loop C. X When, the adjacent substituent R X They can be optionally connected to form a ring, and can also represent adjacent substituents R and R. X They can be optionally connected to form a ring; obviously, to those skilled in the art, adjacent substituents R and R X Alternatively, they may not connect to form a ring. In this case, adjacent substituents R do not connect to form a ring, and / or adjacent substituents R X It also does not connect to form a ring, and / or adjacent substituents R and R X They also do not connect to form a loop.

[0092] In this paper, adjacent substituents R n ,R m The ability to optionally connect to form a ring can be represented by the presence of a substituent R. n ,R m When, adjacent substituent groups, such as substituent R n , and R m One or more of them can connect to form a ring. It is obvious that when a substituent R is present... n ,R m In this case, adjacent substituent groups may not be connected to form a ring.

[0093] According to some embodiments of the present invention, in Formula 1 or Formula 2, the rings A, B, and C, each time they appear, are selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms.

[0094] According to some embodiments of the present invention, in Formula 1 or Formula 2, the rings A, B, and C are selected from 5-membered unsaturated carbon rings, 6-10-membered aromatic rings, or 5-15-membered heteroaromatic rings each time they appear.

[0095] According to some embodiments of the present invention, in Formula 1 or Formula 2, rings A, B, and C are selected from 6-10 membered aromatic rings or 5-15 membered heteroaromatic rings each time they appear. In some specific embodiments, in Formula 1 or Formula 2, rings A, B, and C are selected from benzene rings, naphthyl rings, fluorene rings, furan rings, thiophene rings, pyridine rings, pyrimidine rings, pyridazine rings, pyran rings, pyrrole rings, imidazole rings, pyrazole rings, oxazole rings, thiazole rings, dibenzofuran rings, dibenzothiophene rings, or carbazole rings each time they appear. In some specific embodiments, rings A and B are each independently selected from benzene rings, naphthyl rings, fluorene rings, dibenzofuran rings, and dibenzothiophene rings. In some specific embodiments, ring C is a benzene ring. In some embodiments, rings A, B, and C are all benzene rings.

[0096] According to some embodiments of the present invention, wherein the H, each time it appears, is selected from structures represented by formulas 1-1 to 1-4 and 2-1 to 2-4:

[0097]

[0098]

[0099] Where: R, Rx, A1, A2 and A3 are defined as in Equation 1 or Equation 2;

[0100] X1 to X 10Each occurrence is either identically or differently selected from N or CRx; Y and Z each occurrence is either identically or differently selected from NR. x O and S.

[0101] According to some embodiments of the present invention, in the structures represented by formulas 1-1 to 1-4 and 2-1 to 2-4, R and R X Each time it appears, it is selected from the group consisting of, in the same or different ways, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic alkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphin groups, and combinations thereof.

[0102] According to some embodiments of the present invention, in the structures represented by Equations 1, 1-1 to 1-4 and 2, 2-1 to 2-4, R and R X Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0103] According to some embodiments of the present invention, in the structures represented by Equations 1, 1-1 to 1-4 and 2, 2-1 to 2-4, R and R X Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, amino, hydroxyl, mercapto, and combinations thereof.

[0104] According to some embodiments of the present invention, in the structures represented by Equations 1, 1-1 to 1-4 and 2, 2-1 to 2-4, R and R XEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted butenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, amino, hydroxyl, mercapto, and combinations thereof.

[0105] In some specific embodiments, in the structures represented by Formula 1, Formula 1-1 to Formula 1-4, and Formula 2, Formula 2-1 to Formula 2-4, R is selected from hydrogen or deuterium. X Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, vinyl, propenyl, butenyl, phenyl, naphthyl, biphenyl, anthracene, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, amino, hydroxyl, mercapto, and combinations thereof.

[0106] According to some embodiments of the present invention, in the structures represented by Equations 1, 1-1 to 1-4 and 2, 2-1 to 2-4, R and R X At least one of them is selected from deuterium, substituted or unsubstituted aryl group having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl group having 3-30 carbon atoms.

[0107] According to some embodiments of the present invention, in the structures represented by Equations 1, 1-1 to 1-4 and 2, 2-1 to 2-4, R and R X At least one of them is selected from deuterium, phenyl, biphenyl, naphthyl or pyridyl.

[0108] According to some embodiments of the present invention, in the structures represented by Formula 1, Formula 1-1 to Formula 1-4 and Formula 2, Formula 2-1 to Formula 2-4, the substituent R between A1 and A2 can optionally be connected to form a carbon ring having 5-18 carbon atoms, or a heterocyclic carbon ring having 3-18 carbon atoms; preferably a 5-membered carbon ring, an aromatic ring having 6-18 carbon atoms, or a heterocyclic aromatic ring having 3-18 carbon atoms; more preferably a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a furan ring, a thiophene ring, a fluorene ring, a silylfluorene ring, or combinations thereof.

[0109] According to some embodiments of the present invention, the compound of formula 1 is selected from the structures shown in formula 1-1 above. According to some embodiments of the present invention, the compound of formula 2 is selected from the structures shown in formula 2-1 above.

[0110] According to some embodiments of the present invention, in the structure represented by Formula 1-1 or Formula 2-1, any two or more substituents R in A1 to A3 are connected to form a 5-10 membered ring. According to some embodiments of the present invention, in the structure represented by Formula 1-1 or Formula 2-1, each substituent R in X1 to X4... x Between them, any two or more can be connected to form a 5-10 member ring. According to some embodiments of the present invention, in the structure represented by formula 1-1 or formula 2-1, each substituent R in X5 to X7 x Between these elements, any two or more can be connected to form a 5-10 element ring. According to some embodiments of the present invention, in the structure represented by Equation 1-1 or Equation 2-1, X8 to X... 10 Each substituent R in x Between any two or more elements, any two or more can be connected to form a 5-10 element ring.

[0111] According to some embodiments of the present invention, the compound has the structure shown in Formula 1-a or Formula 2-a:

[0112]

[0113] In Equations 1-a and 2-a, rings A, B, R, and R x The definitions are the same as those in Equation 1 and Equation 2.

[0114] According to some preferred embodiments of the present invention, the compound has the structure shown in Formulas 1-1-1 to 1-1-5, or Formulas 2-1-1 to 2-1-5:

[0115]

[0116]

[0117] In equations 1-1-1 to 1-1-5 and 2-1-1 to 2-1-5 above, R and R X The definitions are the same as in Equation 1-1 or Equation 2-1; preferably, R and R X Each is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, phenyl, naphthyl, anthracene, phenanthrene, biphenyl, terphenyl, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, and combinations thereof;

[0118] In Equations 1-1-3, 1-1-5, 2-1-3, and 2-1-5, X is selected from O, S, and CR. a R b , where R a and R bEach group is independently selected from one or more of the following groups: hydrogen, deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, deuterated cycloalkyl having 3-10 carbon atoms, halocycloalkyl having 3-10 carbon atoms, alkoxy having 1-10 carbon atoms, aryl having 6-15 carbon atoms, deuterated aryl having 6-15 carbon atoms, haloaryl having 6-15 carbon atoms, aryloxy having 6-15 carbon atoms, heteroaryl having 3-15 carbon atoms, deuterated heteroaryl having 3-15 carbon atoms, haloheteroaryl having 3-15 carbon atoms, heteroaryloxy having 3-15 carbon atoms, and combinations thereof.

[0119] According to some embodiments of the present invention, the H is selected from the group consisting of the following structures each time it appears:

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] According to some embodiments of the present invention, the hydrogen in the compounds represented by structures H-1 to H-108 may be partially or completely replaced by deuterium.

[0127] According to some embodiments of the present invention, in Formula 4, ring D is selected from aryl groups having 6-18 carbon atoms, or heteroaryl groups having 3-18 carbon atoms, and combinations thereof. In some specific embodiments, ring D is selected from phenyl, naphthyl, biphenyl, terphenyl, anthracene, phenanthryl, fluorenyl, triphenylene, carbazole, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, furanyl, thiophene, and combinations thereof.

[0128] According to some embodiments of the present invention, in Formula 4, L1 is selected from substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof. In some specific embodiments, L1 is selected from single bonds, substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, and combinations thereof. In some embodiments, L1 is a single bond.

[0129] According to some embodiments of the present invention, in formula 4, R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-15 carbon atoms, substituted or unsubstituted aroxy groups having 6-15 carbon atoms, substituted or unsubstituted aryl groups having 6-15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-15 carbon atoms.

[0130] In some preferred embodiments, ring D is a benzene ring. In some preferred embodiments, ring D is a naphthalene ring.

[0131] In some specific embodiments, L has the structure shown in Equations 4-1 to 4-4:

[0132]

[0133] In some implementations, R n It is selected from hydrogen, deuterium, alkyl groups having 1-6 carbon atoms, cycloalkyl groups having 3-8 carbon atoms, alkoxy groups having 1-6 carbon atoms, aryl groups having 6-12 carbon atoms, heteroaryl groups having 5-12 carbon atoms, and aryloxy groups having 6-12 carbon atoms.

[0134] In some implementations, R n It is selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthyl, and biphenyl.

[0135] According to some embodiments of the invention, L in the compound is selected from the group consisting of: substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted furanylene, substituted or unsubstituted thiopheneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted carbazolylene, and combinations thereof.

[0136] According to some embodiments of the present invention, wherein each occurrence of L is selected from the group consisting of:

[0137]

[0138]

[0139] In the structures represented by L-1 to L-17, "*" indicates the position connected to H. Indicates the position connected to E.

[0140] According to some embodiments of the present invention, the hydrogen in the structures L-1 to L-17 can be partially or completely replaced by deuterium.

[0141] According to some embodiments of the present invention, in Formula 3, at least two of Z1, Z2, and Z3 are N. In some specific embodiments, Z1 and Z2 are both N. In some specific embodiments, Z1 and Z3 are both N. In some specific embodiments, Z2 and Z3 are both N. In some specific embodiments, Z1, Z2, and Z3 are all N.

[0142] In some embodiments, E has the structure shown in Equation 3-1:

[0143]

[0144] The definitions of Ar1 and Ar2 are the same as in Equation 3.

[0145] According to some embodiments of the present invention, in Formula 3, Ar1 and Ar2 are selected, in the same or different ways, from aryl groups having 6-18 (e.g., 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18) carbon atoms, and heteroaryl groups having 3-18 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18) carbon atoms.

[0146] According to some embodiments of the present invention, in Formula 3, Ar1 and Ar2, each time they appear, are selected from phenyl, biphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, carbazoleyl, pyridyl, pyrimidinyl, and combinations thereof. In some embodiments, at least one of Ar1 and Ar2 is phenyl. In some embodiments, Ar1 is phenyl, and Ar2 is either phenyl or dibenzofuranyl.

[0147] According to some embodiments of the present invention, Ar1 and Ar2 are each independently replaced by one or more substituents R. Ar Replaced by, R Ar Selected from: deuterium, halogen, cyano, alkyl groups having 1-10 carbon atoms, aryl groups having 6-15 carbon atoms, and combinations thereof.

[0148] In some specific embodiments, Ar1 and Ar2, each time they appear, are selected from the group consisting of: phenyl, deuterated phenyl, methyl phenyl, fluorophenyl, tert-butylphenyl, trideuterated methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, carbazoleyl, N-phenylcarbazole, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.

[0149] According to some embodiments of the present invention, E is selected from the group consisting of the following structures each time it appears, either identically or differently:

[0150]

[0151]

[0152]

[0153] According to some embodiments of the present invention, the hydrogen in the structures of E-1 to E-40 can be partially or completely replaced by deuterium.

[0154] According to some embodiments of the present invention, in the compound, H is selected from the group consisting of structures H-1 to H-108, L is selected from the group consisting of structures L-1 to L-17, and E is selected from the group consisting of structures E-1 to E-40, wherein, optionally, the hydrogen in the compound can be partially or completely replaced by deuterium.

[0155] According to some embodiments of the present invention, the compound is selected from the group consisting of compounds C1 to C584; the compounds C1 to C584 have an HLE structure, wherein H, L and E respectively correspond to structures selected from the table below:

[0156] For compounds C1 to C108: H corresponds to the structures shown above as H-1 to H-108, respectively; L is L-1 for all compounds and E is E-1 for all compounds.

[0157] Compounds C109 to C216: H corresponds to the structures shown above as H-1 to H-108, respectively; L is L-1 and E is E-16.

[0158] Compounds C217 to C324: H corresponds to the structures shown above H-1 to H-108 respectively, L is L-2 and E is E-1;

[0159] Compounds C325 to C432: H corresponds to the structures shown above as H-1 to H-108, respectively; L is L-1 and E is E-16.

[0160] Compounds C433 to C470: E corresponds to the structures shown in E-2 to E-40 above (excluding E-16), H is H-1, and L is L-1;

[0161] Compounds C471 to C508: E corresponds to the structures shown above as E-2 to E-40 (excluding E-16), H is H-7, and L is L-1;

[0162] Compounds C509 to C546: E corresponds to the structures shown above (excluding E-16) from E-2 to E-40 respectively, H is H-1 and L is L-2;

[0163] Compounds C547 to C584: E corresponds to the structures shown above (excluding E-16) from E-2 to E-40 respectively, H is H-7 and L is L-2.

[0164] According to some embodiments of the present invention, the compound is selected from compounds C1 to C584 in which hydrogen is partially or completely replaced by deuterium.

[0165] The luminescent material composition provided in the second aspect of the present invention comprises the compound described in the first aspect and at least one doping material.

[0166] According to some embodiments of the present invention, the doped material has M(L) a ) m (L b ) n (L c ) q The structure represented; where L a L b L c These are the first, second, and third ligands that coordinate with metal M, respectively; L a L b L c Can be selectively linked to form multidentate ligands; L a L b L c They can be the same or different; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L... a They can be the same or different; when n is 2, the two Lb can be the same or different.

[0167] In some embodiments, the ligand La has a structure as shown in Formula 5:

[0168]

[0169] Among them, ring E is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0170] Ring F is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0171] Y a Y b Each time it appears, it is selected from CR in the same or different ways. Y Or N;

[0172] X1, X2, X3, and X4 are selected from CR each time they appear, either identically or differently. xx Or N;

[0173] R d1 and R e1 Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted; and R d1 and R e1 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted aroxy groups having 6-30 carbon atoms. Substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; optionally, R d1 and R e1 Any two or more of them are connected to form a ring.

[0174] In some embodiments, the ligand L b Selected from at least one of the following structures:

[0175]

[0176] R a R b and R c Each occurrence, whether identical or different, indicates single substitution, multiple substitution, or no substitution;

[0177] X bEach time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0178] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted groups having 6-30 carbon atoms. The aryl group, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfinyl group, sulfonyl group, phosphinyl group, and combinations thereof having 0-20 carbon atoms;

[0179] Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0180] In some embodiments, the ligand Lc has the structure represented by Formula 6:

[0181]

[0182] R1 to R7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted groups having 6-30 carbon atoms. The aryl group, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof having 0-20 carbon atoms.

[0183] In some embodiments, at least one of R1-R3 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof. In some embodiments, at least one of R4-R6 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0184] In some embodiments, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof. In some embodiments, at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0185] In some embodiments, the metal M is selected from Ir, Pt, or Os. In some embodiments, the metal M is selected from Ir.

[0186] In some embodiments, the doped material is selected from any one of the structures shown in Ir(La)(Lb)(Lc), Ir(La)2(Lb), Ir(La)2(Lc), and Ir(La)(Lc)2.

[0187] The electroluminescent device provided in the third aspect of the present invention includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer comprises the compound described in the first aspect or the light-emitting material composition described in the second aspect.

[0188] In some embodiments, the host material of the light-emitting layer contains the compound described in the first aspect.

[0189] In some embodiments, the electroluminescent device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0190] The fourth aspect of the present invention provides a display component comprising the electroluminescent device described in the third aspect.

[0191] The fifth aspect of this invention provides the use of the compound described in the first aspect or the composition described in the second aspect in the preparation of electroluminescent devices.

[0192] In some embodiments, the compound described in the first aspect of the present invention is used as the host material of the light-emitting layer in an electroluminescent device.

[0193] The materials for specific layers in organic light-emitting devices described in the following embodiments of the present invention can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122M, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0194] Materials described herein for use in specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of host layers, delivery layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273M, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0195] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Agilent liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimation apparatuses, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0196] Material synthesis examples:

[0197] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0198] Synthesis of intermediate H-1:

[0199]

[0200] The synthesis route is as follows:

[0201]

[0202] Specific synthesis steps:

[0203] (1) Under nitrogen atmosphere, N-phenylindole (0.155 mol), 1-iodo-2-nitrobenzene (0.217 mol), anhydrous potassium carbonate (0.466 mol), and palladium acetate (0.0075 mol) were added to a three-necked flask. 500 mL of dioxane was added, and the mixture was heated to reflux and reacted for 14 h. After the reaction was complete, the mixture was cooled to room temperature, washed with water until neutral, and the solvent was removed. The mixture was purified by silica gel chromatography (heptane / dichloromethane) to obtain 28.8 g of H-1-1 yellow powder, with a yield of 58%.

[0204] (2) Under nitrogen atmosphere, compound H-1-1 (0.0917 mol) and triphenylphosphine (0.275 mol) were added to a three-necked flask. The mixture was heated to 160 °C and reacted for 5 h. The temperature was then lowered to 100 °C and 250 mL of toluene was added. After stirring, anhydrous zinc chloride (0.458 mol) was added. After stirring for half an hour, the mixture was filtered. The filtrate was passed through a silica gel column, washed with toluene, concentrated to dryness, and then crystallized with ethanol. 20.9 g of yellow solid H-1-2 was obtained, with a yield of 80.5%.

[0205] (3) Under nitrogen atmosphere, 200 mL of DMAc, compound H-1-2 (0.0741 mol), o-fluorobromobenzene (0.111 mol), and anhydrous cesium carbonate (0.222 mol) were added to a three-necked flask, and the mixture was heated to 150 °C and reacted for 18 h. After the reaction was completed, the cesium carbonate was removed through a silica gel funnel, the filtrate was dried to remove the solvent, and purified by silica gel chromatography (elution with heptane / dichloromethane) to obtain 27.3 g of solid H-1-3, with a yield of 84%.

[0206] (4) Under nitrogen atmosphere, 150 mL of toluene, 100 mL of ethanol, and 100 mL of water were added to a three-necked flask. Compound H-1-3 (0.0625 mol) was added, along with 2-chloro-6-nitrobenzinol boron ester (0.0937 mol), anhydrous potassium carbonate (0.125 mol), and tetrakis(triphenylphosphine)palladium (0.000625 mol). The temperature was raised to 80 °C, and the reaction was allowed to proceed for 6 h. After the reaction was complete, 300 mL of water was added, and the mixture was separated. The aqueous phase was extracted with toluene, and the organic phase was concentrated and purified by silica gel chromatography (elution with heptane / dichloromethane). 25.6 g of solid H-1-4 was obtained, with a yield of 80%.

[0207] (5) Under nitrogen atmosphere, 25.6 g of compound H-1-4 (0.050 mol), palladium acetate (0.0025 mol), 32.5 g of cesium carbonate, 50 mL of DMAc, and 200 mL of xylene were added to a three-necked flask. The mixture was stirred and heated to 130 °C for 18 h. After the reaction was complete, 200 mL of water was added, followed by extraction with 200 mL of toluene. After removing the organic phase, ethanol was added to crystallize, yielding 17.84 g of yellow solid H-1-5, with a yield of 75%.

[0208] (6) Compound H-1-5 (0.0373 mol) and triphenylphosphine (0.112 mol) were added to a three-necked flask, and the temperature was raised to 160 °C and reacted for 5 h. After the reaction was completed, the temperature was lowered to 100 °C, 200 mL of toluene was added, and after stirring, anhydrous zinc chloride (0.186 mol) was added. The mixture was stirred for half an hour, filtered, and the filtrate was passed through a silica gel column. After drying the column chromatography solution, ethanol was added to crystallize the solution, and 14.3 g of yellow solid H-1 was obtained, with a yield of 86%.

[0209] Synthesis of intermediate H-7:

[0210]

[0211] Specific synthesis steps:

[0212] (1) Under nitrogen atmosphere, a mixture of 2-bromobenzonitrile (1 mol), aniline (1.5 mol), Pd₂(dba)₃ (0.05 mol), tri-tert-butylphosphine (0.1 mol), and Cs₂CO₃ (2 mol) with 1,4-dioxane (1 L) was added to a three-necked flask and heated at 95 °C for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added and stirred, and the mixture was separated. The organic solution was concentrated. Purification by silica gel chromatography (using heptane / dichloromethane as eluent) yielded 128 g of a yellow solid, with a yield of 71%.

[0213] (2) Under nitrogen atmosphere, 500 mL of dry DMF was added to a three-necked flask, followed by compound 1-1 (0.257 mol). The temperature was lowered to below 0 °C, and then 0.276 mol of 60% NaH was added. The mixture was stirred at 0 °C for 30 min, followed by the addition of a mixed solution of 0.25 mol of 2-iodobenzyl bromide and DMF over half an hour. The reaction was allowed to proceed for 3 h after the addition was complete. After the reaction was complete, 20 mL of anhydrous ethanol was added dropwise while maintaining the temperature at 0 °C. The reaction solution was then poured into 2 L of water, resulting in the precipitation of a large amount of white solid. The solid was filtered, and the filter cake was washed with water to obtain 73 g of white solid, with a yield of 65%.

[0214] (3) Under nitrogen atmosphere, 500 mL of chlorobenzene, compound 1-2 (0.178 mol), potassium tert-butoxide (0.39 mol), and anhydrous copper sulfate (0.009 mol) were added to a three-necked flask, and the mixture was reacted at 90 °C for 18 h. After the reaction was completed, the mixture was cooled to room temperature, and 200 mL of water was added to the reaction system. The mixture was stirred and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was concentrated and purified by silica gel chromatography (heptane / dichloromethane as eluent) to obtain 31.6 g of a yellow solid, with a yield of 63%.

[0215] (4) Under nitrogen atmosphere, 500 mL of DMAc, compound 1-3 (0.106 mol), o-fluorobromobenzene (0.137 mol), and anhydrous cesium carbonate (0.266 mol) were added to a three-necked flask, and the mixture was heated to 150 °C and reacted for 18 h. After the reaction was completed, the cesium carbonate was removed through a silica gel funnel, the filtrate was dried to remove the solvent, and purified by silica gel chromatography (elution with heptane / dichloromethane) to obtain 32.5 g of solid, with a yield of 70%.

[0216] (5) Under nitrogen atmosphere, 150 mL of toluene, 100 mL of ethanol, and 100 mL of water were added to a three-necked flask. Compound 1-4 (0.0743 mol) was added, along with 2-chloro-6-nitrobenzinol boron ester (0.111 mol), anhydrous potassium carbonate (0.149 mol), and Pd(PPh3)4 (0.00074 mol). The temperature was raised to 80 °C, and the reaction was allowed to proceed for 6 h. After the reaction was complete, 300 mL of water was added, and the mixture was separated. The aqueous phase was extracted with toluene, and the organic phase was concentrated and purified by silica gel chromatography (elution with heptane / dichloromethane). 32.5 g of solid was obtained, with a yield of 80%.

[0217] (6) Compound 1-5 (0.0632 mol), cesium carbonate (0.19 mol), and palladium acetate (0.003 mol) were added to a three-necked flask under nitrogen atmosphere. 40 mL of DMAc and 350 mL of xylene were also added, and the mixture was heated to 130 °C and reacted for 18 h. After the reaction was complete, 500 mL of water and 200 mL of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted with toluene, and the organic phase was desolvated. Ethanol was added, and the mixture was recrystallized to give 23 g of a yellow solid, with a yield of 76%.

[0218] (7) Compound 1-6 (0.048 mol) and triphenylphosphine (0.144 mol) were added to a three-necked flask. The mixture was heated to 110 °C to melt the compounds, and stirring was started. The mixture was then heated to 160 °C and reacted for 5 h. After the reaction was completed, the temperature was lowered to 100 °C, 200 mL of toluene was added, and anhydrous zinc chloride (0.241 mol) was added. The mixture was stirred for 0.5 h, filtered, and the toluene in the filtrate was passed through a column to remove the solvent. The residue was then crystallized from ethanol to obtain 17.2 g of a yellow solid, with a yield of 80%.

[0219] Example 1: Synthesis of compound C1

[0220]

[0221] The synthetic route is as follows:

[0222]

[0223] (1) In a 2L dry three-necked flask under nitrogen protection, 2-chloro-4,6-diphenyl-1,3,5-triazine (26.7g, 0.1mol), o-fluorophenylboronic acid (15.4g, 0.11mol), potassium carbonate (41.4g, 0.3mol), and tetraphenylphosphine palladium (1.16g, 1mmol), 250mL toluene, 200mL ethanol, and 200mL water were added sequentially. The mixture was heated to 100℃ and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, washed with 500mL of water, and the resulting solid was filtered. The solid was then dissolved in 700mL of toluene and passed through a silica gel-alumina fast column. The filtrate was concentrated to at least the amount of solvent, filtered, and the solid was obtained. The solid was then slurried with a small amount of toluene for 2 hours and filtered again to obtain 27.80g of E-1-M1, with a yield of 85%.

[0224] (2) Under nitrogen atmosphere, compound H-1 (0.01 mol), compound E-1-M1 (0.011 mol), anhydrous cesium carbonate (0.03 mol), and 50 mL DMAc were added to a three-necked flask. The mixture was stirred and heated to reflux for 18 h. After the reaction was complete, the mixture was cooled to room temperature, and 100 mL of water and 200 mL of dichloromethane were added to the system. The mixture was separated, and the aqueous phase was extracted with dichloromethane. The organic phase was then desolvated, and purified by silica gel chromatography (elution with heptane / dichloromethane) to give 4.4 g of compound C1 as a yellow solid, with a yield of 58.6%.

[0225] Product MS (m / e): 752; 1 H NMR (400MHz, CDCl3): δ8.45-8.36(m,4H),8.18-8.12(m,1H),8.08-8.02(m,1H),7.97(dd,1H),7.79-7.71(m,2H) ,7.70-7.61(m,3H),7.59(dd,1H),7.56-7.45(m,11H),7.45-7.37(m,3H),7.38-7.34(m,2H),7.34-7.25(m,3H).

[0226] Example 2: Synthesis of compound C7

[0227]

[0228] The synthesis route is as follows:

[0229]

[0230] Under nitrogen atmosphere, compound H-7 (0.01 mol), compound E-1-M1 (0.011 mol), anhydrous cesium carbonate (0.03 mol), and 50 mL of DMAc were added to a three-necked flask. Stirring was started, and the mixture was heated to reflux and reacted for 18 h. After the reaction was complete, the mixture was cooled to room temperature, and 100 mL of water and 200 mL of dichloromethane were added. The mixture was separated, and the aqueous phase was extracted with dichloromethane. The organic phase was then desolvated, and purified by silica gel chromatography (eluting with heptane / dichloromethane) to give 4.5 g of compound C7 as a yellow solid, with a yield of 59.6%.

[0231] Product MS (m / e): 752. 1 H NMR (400MHz, CDCl3): δ8.62(dd,1H),8.21–8.14(m,2H),8.01(d,1H),7.79(td,1H),7.77–7.57(m,7H),7.50 (ddd,4H),7.40(d,1H),7.36–7.25(m,6H),7.28–7.15(m,5H),7.12–7.06(m,1H),6.96(t,2H),6.77(d,1H).

[0232] Example 3: Synthesis of compound C109

[0233]

[0234] The synthesis route is as follows:

[0235]

[0236] Specific synthesis steps:

[0237] The target compound C109 was obtained by replacing 2-chloro-4,6-diphenyl-1,3,5-triazine with 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine, with other starting materials and procedures as described in Example 1. MS (m / e) of the product: 842.

[0238] Example 4: Synthesis of compound C115

[0239]

[0240] The synthesis route is as follows:

[0241]

[0242] Specific synthesis steps:

[0243] Intermediate E-1-M1 was replaced with intermediate E-16-M1, and other starting materials and procedures were followed as in Example 1 to obtain the target compound C115. MS (m / e) of the product: 842; 1 H NMR (400MHz, CDCl3): δ8.45–8.37(m,2H),8.32(dd,1H),8.08(dd,1H),7.98(ddd,2H),7.87–7.77(m,2H),7.74-7.57(m,7H),7.54–7.28(m,19H).

[0244] Examples 5-8

[0245] Based on the synthesis schemes of Examples 1 to 4, four other compounds were synthesized, as detailed in Table 1 below.

[0246] Table 1

[0247]

[0248]

[0249] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0250] Device Example 1

[0251] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate is achieved sequentially on the ITO anode via thermal vacuum. Simultaneously, the deposited compounds HT and NDP-9 are used as a hole injection layer (HIL), with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the compound 1 of the present invention, which is the main component, and the compound RD, which is the dopant, are co-deposited as an emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL) with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0252] Device Examples 2 to 8

[0253] The method is the same as in Device Example 1, except that in the light-emitting layer (EML), the compounds C7, C109, C115, C217, C223, C325 and C331 of the present invention listed in Table 2 are used instead of compound C1 as the main material.

[0254] Device Comparison Example 1

[0255] The implementation of Comparative Example 1 is the same as that of Example 1, except that compound A is used instead of compound 1 of the present invention as the main material in the light-emitting layer (EML).

[0256] The material structure used in the device is shown below:

[0257]

[0258]

[0259] Table 2 lists the values ​​at 15 mA / cm 2 Under the given conditions, the current efficiency (CE), maximum wavelength (λmax), and external quantum efficiency (EQE) were measured. To better illustrate the data comparison, the CE and EQE data of Comparative Example 1 were set to 100%. The CE and EQE data of Examples 1 to 8 were all converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 2.

[0260] Table 2 Device Data:

[0261]

[0262] discuss:

[0263] As shown in Table 2, the maximum wavelength of Comparative Example 1 and Examples 1-8 remained essentially unchanged. At 15 mA / cm² 2The EQE of Examples 1 to 8, measured at current density, was 10% to 19% higher than that of Comparative Example 1; the CE of Examples 1 to 8 was 12% to 24% higher than that of Comparative Example 1, showing a significant improvement. The data indicate that the examples exhibit superior luminous efficiency compared to the comparative examples. Specifically, the compounds of this invention, which are formed by connecting hole transport units with dihydroindole and indole aziridine macrocyclic structures to electron transport units with triazine or similar structures, show different device performance compared to Comparative Example A due to the change in the hole transport unit core. Unexpectedly, this results in excellent device performance, leading to higher current efficiency and external quantum efficiency, and a significant improvement in device performance. This demonstrates the unique advantages of the compounds of this invention.

[0264] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A compound having a structure represented by HLE, wherein L is selected from the group consisting of: Optionally, the hydrogen in the structures L-1 to L-3 described above can be partially or completely replaced by deuterium; "*" indicates the position where L and H are connected. Indicates the position where L and E are connected; H is selected from the group consisting of the following structures: Optionally, hydrogen in the structure above can be partially or completely replaced by deuterium; E is selected from the group consisting of the following structures: Optionally, the hydrogen in the above structure can be partially or completely replaced by deuterium.

2. The compound according to claim 1, characterized in that, The compounds are selected from the group consisting of the compounds shown in the table below; the compounds have an HLE structure, wherein H, L, and E are respectively selected from the following structures: Optionally, the hydrogen in the compounds in the table above can be partially or completely replaced by deuterium.

3. A luminescent material composition comprising the compound according to any one of claims 1-2 and at least one dopant material.

4. The luminescent material composition according to claim 3, characterized in that, The doped material is a phosphorescent material.

5. The luminescent material composition according to claim 3, characterized in that, The doped material has M(L) a ) m (L b ) n (L c ) q The structure represented; where L a L b L c These are the first, second, and third ligands that coordinate with metal M, respectively; L a L b L c Can be selectively linked to form multidentate ligands; L a L b L c They can be the same or different; m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L... a They can be the same or different; when n is 2, the two Lb can be the same or different. The ligand La has the structure shown in Formula 5: Among them, ring E is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring F is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring; Y a Y b Each time it appears, it is selected from CR in the same or different ways. Y Or N; X1, X2, X3, and X4 are selected from CR each time they appear, either identically or differently. xx Or N; R d1 and R e1 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; R Y R xx R d1 and R e1 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted aroxy groups having 6-30 carbon atoms. Substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; optionally, R d1 and R e1 Any two or more of them are connected to form a ring; ligand L b Selected from at least one of the following structures: R a R b and R c Each occurrence, whether identical or different, indicates single substitution, multiple substitution, or no substitution; X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ; R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted groups having 6-30 carbon atoms. The aryl group, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfinyl group, sulfonyl group, phosphinyl group, and combinations thereof having 0-20 carbon atoms; The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a loop; The ligand Lc has the structure represented by Equation 6: R1 to R7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, and substituted or unsubstituted groups having 6-30 carbon atoms. The aryl group, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, substituted or unsubstituted arylsilyl group having 6-20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphin group, and combinations thereof having 0-20 carbon atoms.

6. The luminescent material composition according to claim 5, characterized in that, At least one of R1-R3 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

7. The luminescent material composition according to claim 5, characterized in that, At least two of R1-R3 are selected from alkyl groups having 1-20 carbon atoms (substituted or unsubstituted), cycloalkyl groups having 3-20 cyclic carbon atoms (substituted or unsubstituted), heteroalkyl groups having 1-20 carbon atoms (substituted or unsubstituted), or combinations thereof.

8. The luminescent material composition according to claim 5, characterized in that, R4-R6 includes at least two selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

9. The luminescent material composition according to claim 3, characterized in that, Metal M is selected from Ir, Pt, or Os.

10. The luminescent material composition according to claim 3, characterized in that, Metal M is selected from Ir.

11. The luminescent material composition according to claim 3, characterized in that, The doped material is selected from any one of the structures shown in Ir(La)(Lb)(Lc), Ir(La)2(Lb), Ir(La)2(Lc), and Ir(La)(Lc)2.

12. An electroluminescent device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer comprising a compound according to any one of claims 1-2 or a light-emitting material composition according to any one of claims 3-11.

13. The electroluminescent device as described in claim 12, characterized in that, The main material of the light-emitting layer contains the compound according to any one of claims 1-2.

14. The electroluminescent device as described in claim 12, characterized in that, The electroluminescent device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

15. A display component comprising the electroluminescent device according to any one of claims 12-14.

16. The use of the compound according to any one of claims 1-2 or the composition according to any one of claims 3-11 in the preparation of electroluminescent devices.

17. The application as described in claim 16, characterized in that, The compound is used as the host material for the light-emitting layer in electroluminescent devices.

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