Organic Electroluminescent Materials and Devices

Abstract

An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is a compound having a structure of Formula 1. The compound can be used as a host material in an electroluminescent device. These novel compounds can improve the efficiency of the electroluminescent device and can provide better device performance. An electroluminescent device and a composition are also disclosed.

Description

Technical Field

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound having the structure of Formula 1, and an organic electroluminescent device and a composition comprising the compound. Background Art

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between a cathode and an anode. Since OLEDs are a self-emitting solid state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.

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

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain light-emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can become polymer OLEDs.

[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.

[0007] The emission color of OLEDs can be achieved through the structural design of the light-emitting materials. OLEDs can include one or more light-emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desired to have a more saturated emission spectrum, higher efficiency, and longer device lifetime.

[0008] CN111320612A discloses an organic electroluminescent compound, an organic optical compound having the following structure Group A must contain at least one N atom (heteroaryl). It does not disclose or teach the application of connecting an aryl group to the nitrogen atom of benzocarbazole.

[0009] WO2021132982A1 discloses an organic electroluminescent compound, an organic optical compound having the following structure

[0010] wherein R 1 is an amino structure, that is, an amino group must be bonded to the benzonaphtho-fused five-membered heterocyclic nucleus in its compound. The introduction of the amino group with strong electron-donating properties will greatly change the charge transport properties of its compound. It does not disclose or teach the application of connecting only neutral groups or p-type groups to the benzocarbazole nucleus structure.

[0011] KR20200056589A discloses an organic electroluminescent compound, an organic optical compound having the following structure

[0012] The triazine in the general formula compound it discloses is respectively connected to carbazole and the 6-5-6 fused ring, but it does not disclose or teach the application of the compound formed by connecting triazine and its similar structures at specific positions of a specific benzocarbazole structure.

[0013] However, there is still room for improvement in the numerous host materials reported at present. To meet the increasing demands of the industry, especially for performance requirements such as higher device efficiency, longer device life, and lower driving voltage, new materials still need further research and development. Summary of the Invention

[0014] The present invention aims to provide a series of compounds having the structure of formula 1 to solve at least part of the above problems. The compounds can be used as host materials in organic electroluminescent devices. These new compounds can improve the efficiency of electroluminescent devices and provide better device performance.

[0015] According to an embodiment of the present invention, a compound having the structure represented by formula 1 is disclosed:

[0016]

[0017] wherein, Ar is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

[0018] X 1 to X 9 are the same or different each time they appear and are selected from N or CR x ,

[0019] X 10 to X 14Each occurrence is the same as or different from and is selected from N or CR, and X 10 to X 14 at least one of which is N;

[0020] L is each occurrence the same as or different from and is selected from a single bond or a substituted or unsubstituted arylene having 6 - 30 carbon atoms;

[0021] R, R x Each occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0022] Adjacent substituents R, R x can optionally be connected to form a ring.

[0023] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode; the organic layer contains the compound shown in the above embodiment.

[0024] According to another embodiment of the present invention, a composition is also disclosed, which contains the compound shown in the above embodiment.

[0025] The novel compound having the structure of Formula 1 disclosed by the present invention can be used as a host material in an electroluminescent device. These novel compounds can improve the efficiency of the electroluminescent device and can provide better device performance. Description of the Drawings

[0026] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the compounds and compositions disclosed herein.

[0027] Figure 2Another schematic diagram of an organic light-emitting device that can contain the compounds and compositions disclosed herein. Detailed Description

[0028] OLEDs can be fabricated on various substrates such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. Device 100 can 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 and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704B2, the entire content of which is incorporated herein by reference.

[0029] There are more examples of each of these layers. For example, U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -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. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety, and include a composite cathode having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of blocking layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of the protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0030] The above-described layered structure is provided by way of non-limiting examples. The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve the desired emission spectrum.

[0031] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0032] The OLED also requires a encapsulation layer, such as Figure 2 Schematically and non-limitingly shows the organic light-emitting device 200, which Figure 1 Differently, an encapsulation layer 102 can also be included above the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function 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 outside the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0033] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) with the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0034] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0035] As used herein, "top" means farthest from the substrate, and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" "on" the second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer "contacts" the second layer, there can be other layers between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed" "on" the anode.

[0036] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0037] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0038] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistics limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0039] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay of the triplet state, the fraction of the singlet excited state that is refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.

[0040] The characteristics of E-type delayed fluorescence can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0041] Definition of substituent terms

[0042] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0043] Alkyl – As used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.

[0044] Cycloalkyl – As used herein, includes cyclic alkyls. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyls include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0045] Heteroalkyl – As used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyls include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0046] Alkenyl - As used herein, it encompasses straight-chain, branched-chain, and cyclic olefin groups. The alkenyl can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0047] Alkynyl - As used herein, it encompasses straight-chain alkynyl groups. The alkynyl can be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylene, phenylpropyne, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylacetylene are preferred. Additionally, the alkynyl can be optionally substituted.

[0048] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fluoranthene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl include phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 4-p-terphenyl, 3-p-terphenyl, 2-p-terphenyl, 4-m-terphenyl, 3-m-terphenyl, 2-m-terphenyl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-4-p-terphenyl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 2,5-dimethylphenyl, mesityl, and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0049] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. 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. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrothienyl. Additionally, the heterocyclic group may be optionally substituted.

[0050] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Heteroaryl also refers to heteroaromatic group. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole, and their nitrogen analogs. Additionally, the heteroaryl may be optionally substituted.

[0051] Alkoxy - As used herein, it is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyl-oxy, ethoxyethyl-oxy, methoxymethyl-oxy and ethoxymethyl-oxy. Additionally, the alkoxy can be optionally substituted.

[0052] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0053] Aralkyl - As used herein, it encompasses alkyl substituted by aryl. The aralkyl can be an aralkyl having 7 to 30 carbon atoms, preferably an aralkyl having 7 to 20 carbon atoms, more preferably an aralkyl having 7 to 13 carbon atoms. Examples of aralkyl include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, 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 aralkyl can be optionally substituted.

[0054] Alkylsilyl – As used herein, it encompasses a silicon group substituted with an alkyl group. The alkylsilyl can be an alkylsilyl having 3 - 20 carbon atoms, preferably an alkylsilyl having 3 to 10 carbon atoms. Examples of the alkylsilyl include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, methyl-di-tert-butylsilyl. Additionally, the alkylsilyl can be optionally substituted.

[0055] Arylsilyl – As used herein, it encompasses a silicon group substituted with at least one aryl group. The arylsilyl can be an arylsilyl having 6 - 30 carbon atoms, preferably an arylsilyl having 8 to 20 carbon atoms. Examples of the arylsilyl include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-tert-butylsilyl. Additionally, the arylsilyl can be optionally substituted.

[0056] Alkylgermyl – As used herein, it encompasses a germanium group substituted with an alkyl group. The alkylgermyl can be an alkylgermyl having 3 - 20 carbon atoms, preferably an alkylgermyl having 3 to 10 carbon atoms. Examples of the alkylgermyl include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tri-tert-butylgermyl, triisobutylgermyl, dimethyl-tert-butylgermyl, methyl-di-tert-butylgermyl. Additionally, the alkylgermyl can be optionally substituted.

[0057] Arylgermyl – As used herein, it encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermyl can be an arylgermyl having 6 - 30 carbon atoms, preferably an arylgermyl having 8 to 20 carbon atoms. Examples of the arylgermyl include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyl-tert-butylgermyl. Additionally, the arylgermyl can be optionally substituted.

[0058] In terms such as azadibenzofuran and azadibenzothiophene, the term "aza" means that one or more C-H groups in the corresponding aromatic moiety are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and all such analogs are determined to be included within the terms described herein.

[0059] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following group is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl group, substituted ester group, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl group, ester group, sulfinyl, sulfonyl, and phosphino can be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0060] It should be understood that when a molecular moiety is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a moiety (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or a linking moiety are considered equivalent.

[0061] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or fully replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Due to enhancing the efficiency and stability of the device, the replacement of other stable isotopes in the compounds may be preferred.

[0062] In the compounds mentioned in the present disclosure, polysubstitution refers to the range including disubstitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist at multiple available substitution positions on its connecting structure, and the substituent existing at multiple available substitution positions can be of the same structure or different structures.

[0063] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, 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.

[0064] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0065]

[0066] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0067]

[0068] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0069]

[0070] In addition, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be construed to mean that, when one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following formula:

[0071]

[0072] According to one embodiment of the present invention, a compound having a structure represented by Formula 1 is disclosed:

[0073]

[0074] wherein Ar is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

[0075] X 1 to X 9 is the same or different each time it appears and is selected from N or CR x ,

[0076] X 10 to X 14 is the same or different each time it appears and is selected from N or CR, and at least one of X 10 to X 14 is N;

[0077] L is the same or different each time it appears and is selected from a single bond or substituted or unsubstituted arylene groups having 6 to 30 carbon atoms;

[0078] R, R x is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 ring atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl groups having 6 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0079] Adjacent substituents R, R x can optionally be linked to form a ring.

[0080] In this embodiment, adjacent substituents R, R x can optionally be linked to form a ring, which is intended to mean that any one or more of the adjacent substituent groups, for example, between adjacent substituents R, between adjacent substituents R x can be linked to form a ring. Obviously, these adjacent substituent groups may also not be linked to form a ring.

[0081] In this embodiment, when each occurrence of said R x is the same or different and is selected from substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted acyl, substituted carbonyl, substituted carboxyl group, substituted ester group, substituted sulfinyl, substituted sulfonyl or substituted phosphino group, any one of said alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl group, ester group, sulfinyl, sulfonyl and phosphino group is substituted by one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl having 1 - 20 carbon atoms, unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, unsubstituted heteroalkyl having 1 - 20 carbon atoms, unsubstituted heterocyclic group having 3 - 20 ring atoms, unsubstituted aralkyl having 7 - 30 carbon atoms, unsubstituted alkoxy having 1 - 20 carbon atoms, unsubstituted aryloxy having 6 - 30 carbon atoms, unsubstituted alkenyl having 2 - 20 carbon atoms, unsubstituted alkynyl having 2 - 20 carbon atoms, unsubstituted aryl having 6 - 30 carbon atoms, unsubstituted heteroaryl having 3 - 30 carbon atoms, unsubstituted alkylsilyl having 3 - 20 carbon atoms, unsubstituted arylsilyl having 6 - 20 carbon atoms, unsubstituted alkylgermyl having 3 - 20 carbon atoms, unsubstituted arylgermyl having 6 - 20 carbon atoms, acyl, carbonyl, carboxyl group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0082] According to one embodiment of the present invention, in Formula 1, said R, R x , Ar are selected from neutral or p-type groups, such as hydrogen, deuterium, alkyl, aryl, and heteroaryl (such as carbazole), etc., but strong electron-donating groups such as arylamine groups are not suitable for selection.

[0083] According to one embodiment of the present invention, wherein X 1 to X 9 is the same or different each time it appears and is selected from CR x .

[0084] According to one embodiment of the present invention, wherein at least one of X 1 to X 9 is selected from N.

[0085] According to one embodiment of the present invention, wherein said R x is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;

[0086] Adjacent substituents R x can optionally be connected to form a ring.

[0087] In this embodiment, adjacent substituents R x can optionally be connected to form a ring, which is intended to mean that any adjacent substituents R x can be connected to form a ring. Obviously, these adjacent substituents R x can also not be connected to form a ring at all.

[0088] According to one embodiment of the present invention, wherein the compound has a structure represented by one of Formula 1-a to Formula 1-g:

[0089]

[0090] wherein Ar is selected from substituted or unsubstituted aryl having 6-12 carbon atoms; X 10 to X 14 is the same or different each time it appears and is selected from N or CR, and at least one of X 10 to X 14 is N;

[0091] L is the same or different each time it appears and is selected from the group consisting of: a single bond, substituted or unsubstituted arylene having 6-30 carbon atoms;

[0092] R x1 is the same or different each time it appears and represents mono-substitution, multi-substitution or no substitution;

[0093] R, R x1 Each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, and combinations thereof;

[0094] Adjacent substituents R, R x1 can optionally be linked to form a ring.

[0095] As used herein, adjacent substituents R, R x1 can optionally be linked to form a ring, which is intended to mean that any adjacent substituents R can be linked to form a ring, and any adjacent substituents R x1 can be linked to form a ring. Obviously, any adjacent substituents R, R x1 may also not be linked to form a ring.

[0096] According to one embodiment of the present invention, wherein said R x1 Each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof; and when said R x1When the same or different each time selected from substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic group, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl or substituted heteroaryl, any one of the alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, aryl and heteroaryl is substituted by one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclic group having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0097] Adjacent substituents R x1 Can optionally be connected to form a ring.

[0098] In this context, adjacent substituents R x1 Can optionally be connected to form a ring, which is intended to mean that any adjacent substituents R x1 Can be connected to form a ring. Obviously, any adjacent substituents R x1 Can also not be connected to form a ring.

[0099] According to an embodiment of the present invention, wherein the R x1 Each time the same or different is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano group, methyl, ethyl, tert-butyl, phenyl, biphenyl, triphenylene, naphthyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl, pyridyl, and combinations thereof.

[0100] According to an embodiment of the present invention, wherein three of X 10 to X 14 Are N.

[0101] According to an embodiment of the present invention, wherein X 10 , X 12 And X 14 Are N.

[0102] According to one embodiment of the present invention, each occurrence of R is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;

[0103] Adjacent substituents R can optionally be joined to form a ring.

[0104] In this context, adjacent substituents R can optionally be joined to form a ring, which is intended to mean that any adjacent substituents R can be joined to form a ring. Obviously, it is also possible that none of the adjacent substituents R are joined to form a ring.

[0105] According to one embodiment of the present invention, at least one of the Rs is the same or different each time it occurs and is selected from deuterium, halogen, cyano, substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0106] According to one embodiment of the present invention, at least one of the Rs is the same or different each time it occurs and is selected from deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, naphthyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl, pyridyl, and combinations thereof.

[0107] According to one embodiment of the present invention, Ar is selected from the structures represented by one of Formula 2-a to Formula 2-c:

[0108]

[0109] wherein Y is the same or different each time it occurs and is selected from CR y ;

[0110] R yEach occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, and combinations thereof;

[0111] wherein represents the position in the structure of said Ar that is connected to the N atom in Formula 1.

[0112] According to one embodiment of the present invention, wherein said R y Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, and combinations thereof.

[0113] According to one embodiment of the present invention, wherein said Ar is phenyl, biphenyl or naphthyl.

[0114] According to one embodiment of the present invention, wherein each occurrence of said L is the same or different and is selected from a single bond or substituted or unsubstituted arylene having 6 - 24 carbon atoms.

[0115] According to one embodiment of the present invention, wherein each occurrence of said L is the same or different and is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylenylene, trinaphthylene.

[0116] According to one embodiment of the present invention, wherein each occurrence of said L is the same or different and is selected from the group consisting of:

[0117]

[0118] According to an embodiment of the present invention, wherein the hydrogen in L-1 to L-8 is partially or completely replaced by deuterium.

[0119] According to an embodiment of the present invention, wherein the compound has a structure represented by Formula 1-1 or Formula 1-2:

[0120]

[0121] Wherein, R y represents, each time it appears, the same or different, mono-substituted, multi-substituted or unsubstituted;

[0122] R y represents, each time it appears, the same or different, and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, and combinations thereof;

[0123] R represents, each time it appears, the same or different, and is selected from substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0124] In this embodiment, any adjacent substituents R y do not connect to form a ring.

[0125] According to an embodiment of the present invention, wherein in Formula 1-1 or Formula 1-2, the R y represents, each time it appears, the same or different, and is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0126] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound 1 to Compound 288. For the specific structures of Compound 1 to Compound 288, refer to the claims.

[0127] According to one embodiment of the present invention, in the Compound 1 to Compound 288, the hydrogen can be partially or completely replaced by deuterium.

[0128] According to one embodiment of the present invention, an electroluminescent device is also disclosed, which includes:

[0129] an anode,

[0130] a cathode,

[0131] and an organic layer disposed between the anode and the cathode, the organic layer containing a compound having a structure of Formula 1, and the specific structure of the compound is as shown in any of the foregoing embodiments.

[0132] According to one embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the compound is a host material.

[0133] According to one embodiment of the present invention, in the device, the light-emitting layer further includes at least one phosphorescent material.

[0134] According to one embodiment of the present invention, in the device, the phosphorescent material is a metal complex and has a general formula of M(L a ) m (L b ) n (L c ) q ;

[0135] wherein, M is selected from metals with a relative atomic mass greater than 40;

[0136] L a , L b , L c are respectively the first ligand, the second ligand, and the third ligand coordinated with the M; L a , L b , L c can optionally be connected to form a multidentate ligand; for example, any two of L a , L b , and L c can be connected to form a tetradentate ligand; or for another example, L a , L b , and L c can be connected to each other to form a hexadentate ligand; or for yet another example, L a , L b , L c are not connected and thus do not form a multidentate ligand;

[0137] L a 、L b 、L c may be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of m, n and q is equal to the oxidation state of said M; when m is greater than or equal to 2, multiple Ls a may be the same or different; when n is 2, two Ls b may be the same or different;

[0138] L a has the structure shown in Formula 3:

[0139]

[0140] wherein,

[0141] ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0142] ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0143] ring D and ring E are fused via U a and U b ;

[0144] U a and U b are the same or different each time they appear and are selected from C or N;

[0145] R d ,R e are the same or different each time they appear and represent single-substituted, multi-substituted or unsubstituted;

[0146] V 1 -V 4 are the same or different each time they appear and are selected from CR v or N;

[0147] R d ,R e ,R vEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0148] Adjacent substituents R d , R e , R v can optionally be joined to form a ring;

[0149] L b , L c Each occurrence is the same as or different from and is selected from any one of the following structures:

[0150]

[0151] Wherein,

[0152] R a , R b and R c Each occurrence is the same as or different from and represents mono-substitution, multi-substitution, or no substitution;

[0153] X b Each occurrence is the same as or different from and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0154] X c and X d Each occurrence is the same as or different from and is selected from the group consisting of: O, S, Se and NR N2 ;

[0155] R a , R b , Rc , R N1 , R N2 , R C1 and R C2 is each independently selected, each time it appears, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0156] Said ligand L b , L c In the structure of, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be connected to form a ring.

[0157] In this context, adjacent substituents R d , R e , R v can optionally be connected to form a ring, which is intended to mean that when there are substituents R d , substituent R e , substituent R v , among which adjacent substituent groups, such as between adjacent substituents R d , between adjacent substituents R e , between adjacent substituents R v , between adjacent substituents R d and R e , between adjacent substituents R d and R v , and between adjacent substituents R e and R v , any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, when there are substituents Rd and the substituent R e and the substituent R v When this is the case, none of these substituent groups may also be connected to form a ring.

[0158] In this embodiment, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be connected to form a ring, which is intended to represent adjacent substituent groups among them. For example, between two substituents R a , between two substituents R b , between two substituents R c , between the substituent R a and R b , between the substituent R a and R c , between the substituent R b and R c , between the substituent R a and R N1 , between the substituent R b and R N1 , between the substituent R a and R C1 , between the substituent R a and R C2 , between the substituent R b and R C1 , between the substituent R b and R C2 , between the substituent R a and R N2 , between the substituent R b and R N2 , and between R C1 and R C2 , any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may also not be connected to form a ring.

[0159] According to an embodiment of the present invention, in the device, where the phosphorescent light-emitting material is a metal complex, the metal complex has the general formula M(L a ) m (L b ) n ;

[0160] M is selected from metals with a relative atomic mass greater than 40;

[0161] L a , L bThe first ligand and the second ligand coordinated with the M respectively; L a and L b can optionally be connected to form a polydentate ligand;

[0162] m is 1, 2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of m, n and q is equal to the oxidation state of the M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, two L b can be the same or different;

[0163] L a has the structure shown in Formula 3:

[0164]

[0165] wherein,

[0166] ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0167] ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0168] ring D and ring E are fused via U a and U b ;

[0169] U a and U b are the same or different each time they appear and are selected from C or N;

[0170] R d , R e are the same or different each time they appear and represent mono-substituted, multi-substituted or unsubstituted;

[0171] V 1 -V 4 are the same or different each time they appear and are selected from CR v or N;

[0172] R d , R e , R vEach occurrence is the same as or different from each other and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0173] Adjacent substituents R d , R e , R v can optionally be joined to form a ring;

[0174] wherein the ligand L b has the following structure:

[0175]

[0176] wherein, R 1 to R 7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0177] In one embodiment of the present invention, in the device, wherein the ligand L b has the following structure:

[0178]

[0179] wherein, R 1 -R 3 at least one or two of which are selected from 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, or combinations thereof; and / or R 4 -R 6 at least one or two of which are selected from 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, or combinations thereof.

[0180] In one embodiment of the present invention, in the device, wherein the ligand L b has the following structure:

[0181]

[0182] wherein, R 1 -R 3 at least two of which are each independently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or R 4 -R 6 at least two of which are each independently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0183] In one embodiment of the present invention, in the device, wherein the phosphorescent material is an Ir complex, a Pt complex or an Os complex.

[0184] In one embodiment of the present invention, in the device, wherein the phosphorescent material is an Ir complex and has Ir(L a )(L b )(L c ), Ir(L a ) 2 (L b ), Ir(L a ) 2 (Lc ) or Ir(L a )(L c ) 2 The structure shown by any one of them.

[0185] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of a 6-membered fused 6-membered aromatic ring, a 6-membered fused 6-membered heteroaromatic ring, a 6-membered fused 5-membered aromatic ring, and a 6-membered fused 5-membered heteroaromatic ring.

[0186] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline, and aza-phenanthrene.

[0187] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L a , the L a each occurrence is arbitrarily selected from the group consisting of the following structures:

[0188]

[0189]

[0190] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains a ligand L b , the L b each occurrence is the same or different and is selected from the group consisting of the following structures:

[0191]

[0192] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0193]

[0194]

[0195]

[0196] According to one embodiment of the present invention, the light-emitting layer further comprises at least one host material, and the at least one host material has an H 1 -L 1 -Ar 1 structure, wherein H 1 has a structure represented by Formula 4:

[0197]

[0198] In Formula 5, Z 1 -Z 3 and Z 6 -Z 8 are each independently selected from CR z1 or N each time they appear, and two substituents R 4 of Z 5 and Z z2 are connected to form a ring each time they appear, and Z 4 and Z 5 are each independently selected from CR z2 ; and

[0199] L 1 is selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0200] Ar 1 is selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a substituted or unsubstituted amino having 0-20 carbon atoms;

[0201] R z1Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0202] R z2 Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0203] Adjacent substituents R z1 ,R z2 can optionally be joined to form a ring.

[0204] In this example, "*" represents the position in the structure of the H 1 that is connected to the L 1 .

[0205] In this embodiment, adjacent substituents R z1 , R z2 can optionally be joined to form a ring, which is intended to represent a group of adjacent substituents. For example, between adjacent substituents R 1 -Z 3 , between adjacent substituents R z1 in Z 6 -Z 8 , between adjacent substituents R z1 in Z 3 , between the substituent R z1 in Z 4 and the substituent R z2 in Z 3 , between the substituent R z1 in Z 5 and the substituent R z2 in Z 6 , between the substituent R z1 in Z 4 and the substituent R z2 in Z 6 , and between the substituent R z1 in Z 5 and the substituent R z2 in Z

[0206] According to one embodiment of the present invention, in the formula 4, two substituents R 4 in Z 5 and Z z2 are joined to form a ring, and the ring has at least 6 ring atoms.

[0207] According to one embodiment of the present invention, in the formula 4, two substituents R 4 in Z 5 and Z z2 are joined to form a ring, and the ring has at least 7 ring atoms.

[0208] According to one embodiment of the present invention, the at least one host material has the structure of H 1 -L 1 -Ar 1 , where H 1 has a structure represented by any one of formulas 4-1 to 4-8:

[0209]

[0210] In formulas 4-1 to 4-8, Z 1 -Z 3, Z 6 -Z 8 is the same as or different from each occurrence and is selected from CR z1 or N, Z h1 -Z h8 is the same as or different from each occurrence and is selected from CR zh or N, Z m is selected from CR zm or N, Z n is selected from CR zn R zn , O, S or NR zn ;

[0211] L 1 is selected from a single bond, a substituted or unsubstituted alkylene having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3-20 carbon atoms, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof;

[0212] Ar 1 is selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a substituted or unsubstituted amino having 0-20 carbon atoms;

[0213] R z1 , R zh , R zm , R zn is the same as or different from each occurrence and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl having 6-20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, a substituted or unsubstituted arylgermyl having 6-20 carbon atoms, a substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0214] adjacent substituents R z1, R zh , R zm , R zn can optionally be linked to form a ring.

[0215] In this embodiment, adjacent substituents R z1 , R zh , R zm , R zn can optionally be linked to form a ring, which is intended to represent adjacent substituent groups therein. For example, between adjacent substituents R 1 -Z 3 , between adjacent substituents R z1 in Z 6 -Z 8 , between adjacent substituents R z1 , between adjacent substituents R zh , between adjacent substituents R zh and R zm , between adjacent substituents R zn , and between adjacent substituents R zh and R zn , any one or more of these substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups can also not be linked to form a ring.

[0216] According to another embodiment of the present invention, a composition is also disclosed, which comprises a compound represented by Formula 1. The specific structure of the compound is as shown in any of the foregoing embodiments.

[0217] In combination with other materials

[0218] The materials for specific layers in organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0219] The materials described herein as being specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080-0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0220] 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 received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art, including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc., by methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art, including but not limited to evaporation machines produced by AngstromEngineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc., by methods well known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and test methods and can obtain the inherent data of the samples determinately and without interference, the above relevant content will not be elaborated further in this patent.

[0221] Examples of material synthesis:

[0222] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0223] Synthesis Example 1: Synthesis of Compound 6

[0224] Step 1: Synthesis of Intermediate 2

[0225]

[0226] Under nitrogen protection, intermediate 1 (30 g, 93.5 mmol), o-bromophenylboronic acid (22.5 g, 112.2 mmol), tetrakis(triphenylphosphine)palladium (3.2 g, 2.8 mmol), potassium carbonate (25.8 g, 187 mmol), and solvent (toluene / ethanol / water = 280 / 70 / 70 mL) were added to a three-necked flask and reacted overnight at 80 °C. After the reaction was completed, it was cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography (eluent: PE) to obtain intermediate 2 as a yellow solid (2.8 g, yield: 72%).

[0227] Step 2: Synthesis of intermediate 3

[0228]

[0229] Under nitrogen protection, intermediate 2 (22 g, 93.5 mmol), triphenylphosphine (52.7 g, 201.3 mmol), and o-dichlorobenzene (150 mL) were added to a three-necked flask and reacted overnight at 200 °C. After the reaction was complete, it was cooled to room temperature, and the crude product was purified by column chromatography (eluent: PE / DCM = 2 / 1) to obtain intermediate 3 as a white solid (18 g, yield: 65%).

[0230] Step 3: Synthesis of intermediate 4

[0231]

[0232] Under nitrogen protection, intermediate 3 (7 g, 23.6 mmol), iodobenzene (5.8 g, 28.3 mmol), copper(I) chloride (237.6 mg, 2.4 mmol), potassium carbonate (9.8 g, 70.8 mmol), 18-crown-6 (633.6 mg, 2.4 mmol), 1,10-phenanthroline (432 mg, 2.4 mmol), and N-methylpyrrolidone (NMP, 80 mL) were added to a three-necked flask and reacted overnight at 180 °C. It was cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and column chromatography purification (eluent: PE / EA = 20:1) gave intermediate 4 as an off-white solid (6 g, yield: 68%).

[0233] Step 4: Synthesis of intermediate 5

[0234]

[0235] Under nitrogen protection, intermediate 4 (5.8 g, 15.5 mmol) was dissolved in dry tetrahydrofuran (50 mL), and then n-butyllithium (7.4 mL, 18.6 mmol) was slowly added dropwise at -78 °C. The reaction was carried out under these conditions for 1 hour. Then, triisopropyl borate (5.7 g, 30.1 mmol) was slowly added dropwise at -78 °C. After the addition was completed, the temperature was slowly raised to room temperature and the reaction was carried out overnight. After the reaction was completed, water was slowly added dropwise to quench the reaction. The mixture was extracted with dichloromethane, the organic phase was washed with water, dried over anhydrous sodium sulfate and concentrated to remove the solvent. Purification by column chromatography (eluent: PE / EA = 10:1) gave intermediate 5 as a gray solid (5.5 g, yield: 85%).

[0236] Step 5: Synthesis of compound 6

[0237]

[0238] Under nitrogen protection, intermediate 5 (3 g, 7.1 mmol), 2-chloro-4-(dibenzofuran-1-yl)-6-phenyl-[1,3,5]triazine (2.8 g, 7.8 mmol), tetrakis(triphenylphosphine)palladium (410 mg, 0.36 mmol), potassium carbonate (2.0 g, 14.2 mmol), and solvent (toluene / ethanol / water = 40 / 10 / 10 mL) were added to a three-necked flask and reacted at 100 °C overnight. After the reaction was completed, it was cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, concentrated to remove the solvent, and the crude product was purified by column chromatography (eluent: PE / DCM = 4:1) to give compound 6 as a yellow solid (2.7 g, yield: 63%). The product was confirmed to be the target product with a molecular weight of 614.2.

[0239] Synthesis Example 2: Synthesis of compound 7

[0240]

[0241] Under nitrogen protection, intermediate 5 (3 g, 7.1 mmol), intermediate 6 (3.4 g, 7.8 mmol), tetrakis(triphenylphosphine)palladium (410 mg, 0.36 mmol), potassium carbonate (2.0 g, 14.2 mmol), and solvent (toluene / ethanol / water = 40 / 10 / 10 mL) were added to a three-necked flask and reacted at 100 °C overnight. After the reaction was completed, it was cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, concentrated to remove the solvent, and the crude product was purified by column chromatography (eluent: PE / DCM = 4:1) to give compound 7 as a yellow solid (2.4 g, yield: 63%). The product was confirmed to be the target product with a molecular weight of 690.2.

[0242] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0243] Device Example 1

[0244] First, clean the glass substrate, which has an indium tin oxide (ITO) anode with a thickness of 80 nm, and then treat it with UV ozone and oxygen plasma. After treatment, dry the substrate in a nitrogen-filled glove box to remove moisture, and then mount the substrate on a substrate holder and load it into a vacuum chamber. The following specified organic layers are deposited on the ITO anode sequentially by thermal vacuum at a vacuum of about 10 -8 Torr at a rate of Compound HI is used as the hole injection layer (HIL) with a thickness of Compound HT is used as the hole transport layer (HTL) with a thickness of Compound EB is used as the electron blocking layer (EBL) with a thickness of Then, the compound 6 of the present invention as the host and the compound RD as the dopant are co-evaporated to be used as the emitting layer (EML) with a thickness of Compound HB is used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and lithium 8-hydroxyquinolate (Liq) are co-evaporated as the electron transport layer (ETL) with a thickness of Finally, deposit The thickness of lithium 8-hydroxyquinolate (Liq) as the electron injection layer (EIL), and deposit of aluminum as the cathode. Then transfer the device back to the glove box and encapsulate it with a glass cover to complete the device.

[0245] Device Comparative Example 1

[0246] The implementation of Device Comparative Example 1 is the same as that of Device Example 1, except that compound A is used instead of the compound 6 of the present invention as the host in the emitting layer (EML).

[0247] The detailed device layer structure and thickness are shown in the following table. For the layer where more than one material is used, it is doped with different compounds in the recorded weight ratio.

[0248] Table 1 Device Structures of Device Examples and Comparative Examples

[0249]

[0250] The material structures used in the device are as follows:

[0251]

[0252]

[0253] Table 2 lists the maximum emission wavelengths (λ 2 ), current efficiency (CE), and external quantum efficiency (EQE) of the device examples and device comparative examples measured under the condition of a constant current of 15 mA / cm max ).

[0254] Table 2 Device Data

[0255] Device ID <![CDATA[λ max (nm)]]> CE [cd / A] EQE [%] Example 1 623 19.3 21.6 Comparative Example 1 624 17.9 20.3

[0256] Discussion:

[0257] As can be seen from the data in Table 2, the maximum emission wavelengths of Example 1 and Comparative Example 1 are basically the same; in terms of current efficiency, Example 1 is 1.4 cd / A higher than Comparative Example 1, with an increase of 7.8%; in terms of external quantum efficiency, Example 1 is 1.3% higher than Comparative Example 1, with an increase of 6.4%. From the above data, it can be known that after modification at a specific position of benzocarbazole, the steric hindrance of the compound of the present invention is greater than that of Compound A, resulting in a decrease in the planarity of the molecule and a reduction in the π-π stacking between molecules. This difference in structure makes the compound of the present invention have higher device efficiency. It proves the more excellent performance of the compound of the present invention.

[0258] Device Example 2

[0259] The implementation mode of Device Example 2 is the same as that of Device Example 1, except that in the emitting layer (EML), Compound 6 of the present invention and Compound B (the weight ratio of Compound 6 to Compound B is 49%:49%) are used to replace Compound 6 of the present invention as the host.

[0260] Device Example 3

[0261] The implementation mode of Device Example 3 is the same as that of Device Example 2, except that in the emitting layer (EML), Compound 7 of the present invention is used to replace Compound 6 of the present invention.

[0262] Device Comparative Example 2

[0263] The implementation mode of Device Comparative Example 2 is the same as that of Device Example 2, except that in the emitting layer (EML), Compound A is used to replace Compound 6 of the present invention.

[0264] The detailed device layer structures and thicknesses are shown in the following table. For the layers where more than one material is used, they are doped with different compounds in the recorded weight ratios.

[0265] Table 3 Partial Device Structures of Device Examples and Comparative Examples

[0266]

[0267]

[0268] The material structures newly used in the device are as follows:

[0269]

[0270] Table 4 lists the maximum emission wavelengths (λ 2 ), current efficiency (CE), and external quantum efficiency (EQE) of the device examples and device comparative examples measured under the condition of a constant current of 15 mA / cm max 2).

[0271] Table 4 Device Data

[0272] Device ID <![CDATA[λ max (nm)]]> CE [cd / A] EQE [%] Example 2 624 20.3 23.3 Example 3 624 20.0 22.9 Comparative Example 2 624 19.1 21.8

[0273] Discussion:

[0274] As can be seen from the data in Table 4, the maximum emission wavelengths of Examples 2 and 3 and Comparative Example 2 are the same; in terms of current efficiency, Examples 2 and 3 are increased by 6.3% and 4.7% respectively compared with Comparative Example 2; in terms of external quantum efficiency, Examples 2 and 3 are increased by 6.5% and 5.1% respectively compared with Comparative Example 2. The above comparison shows that the compound of the present invention still has higher device efficiency in the multi-host system, and once again proves the more excellent performance of the compound of the present invention.

[0275] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not intended to be limiting.

Claims

1. A compound having a structure represented by Formula 1: Wherein, Ar is selected from the structures represented by one of Formula 2-a, 2-d, 2-e, 2-f: Y is the same as or different from each occurrence and is selected from CR y ; R y each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; X 1 to X 9 selected from CR x ; X 11 is selected from CR, where R is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, X 13 is selected from CR, where R is selected from substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms; and X 10 、X 12 and X 14 is N; The heteroatoms in the heteroaryl are selected from the group consisting of O, S, and N; L is selected from a single bond; R x each occurrence is the same as or different from one another and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof; The substituents in the alkyl, aryl, and heteroaryl are one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, and combinations thereof.

2. The compound according to claim 1, Wherein, The compound has a structure represented by Formula 1-a: Wherein, it is selected from the structures represented by one of Formula 2-a, 2-d, 2-e, 2-f: Y is the same as or different from each other every time it appears and is selected from CR y ; R y each independently selected, each time it appears, from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and combinations thereof; X 11 is selected from CR, where R is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, X 13 is selected from CR, where R is selected from substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms; and X 10 、X 12 and X 14 is N; The heteroatoms in the heteroaryl are selected from the group consisting of O, S, and N; L is selected from a single bond; R x1 each occurrence independently represents mono-substitution, poly-substitution or no substitution, which may be the same or different; R x1 each occurrence independently selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, and combinations thereof; The substituents in the alkyl, aryl, and heteroaryl are one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, and combinations thereof.

3. The compound according to claim 2, Wherein, Said R x1 is the same as or different from each other every time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, and combinations thereof.

4. The compound according to claim 1, Wherein, X 11 is selected from CR, wherein R is selected from phenyl, biphenyl, triphenylene, naphthyl, fluorenyl, and combinations thereof, X 13 is selected from CR, wherein R is selected from dibenzothienyl, dibenzofuranyl, pyridyl, and combinations thereof.

5. The compound according to claim 1, wherein the Ar is selected from the structures represented by one of Formula 2-a, 2-d, 2-e, 2-f: Wherein, Y is the same as or different from each occurrence and is selected from CR y ; R y Each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen.

6. The compound according to claim 5, Wherein, The Ar is phenyl or biphenyl.

7. The compound according to claim 1, Wherein, The compound is selected from the group consisting of the following structures: Wherein, optionally, the hydrogen in Compound 6 to Compound 22, Compound 28 to Compound 30, Compound 32 to Compound 46, Compound 84, Compound 90 to Compound 92, Compound 163 to Compound 179, Compound 202, Compound 203, Compound 221, Compound 225, Compound 231, Compound 235 can be partially or completely replaced by deuterium.

8. An electroluminescent device, which Comprises: An anode, A cathode, And an organic layer disposed between the anode and the cathode; Wherein the organic layer contains the compound according to any one of claims 1-7.

9. The device according to claim 8, Wherein, In the electroluminescent device, the organic layer is a light-emitting layer, and the compound is a host material.

10. The device according to claim 9, Wherein, The light-emitting layer further contains at least one phosphorescent material.

11. The device according to claim 10, Wherein, The phosphorescent luminescent material is a metal complex and has the general formula of M(L a ) m (L b ) n (L c ) q . Wherein, M is selected from metals with a relative atomic mass greater than 40; L a 、L b 、L c are respectively the first ligand, the second ligand and the third ligand coordinated with the M; L a 、L b 、L c can optionally be connected to form a polydentate ligand; L a 、L b 、L c are the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of m, n and q is equal to the oxidation state of said M; when m is greater than or equal to 2, multiple Ls a are the same or different; when n is 2, two Ls b are the same or different; L a has the structure shown in Formula 3: Wherein, Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring D and ring E are fused via U a and U b to be fused; U a and U b each occurrence being the same as or different from C or N; R d ,R e each occurrence independently represents unsubstituted, mono-substituted, or poly-substituted, identically or differently, every time it appears; V 1 -V 4 each occurrence being the same as or different from, independently selected from CR v or N; R d ,R e ,R v each occurrence is the same as or different from each other and is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Adjacent substituents R d , R e , R v can optionally be linked to form a ring; L b 、L c each occurrence being the same as or different from each other and independently selected from any one of the following structures: Wherein, R a ,R b and R c each independently represents, when it appears each time, mono-substitution, poly-substitution, or no substitution; X b each occurrence independently is the same as or different from and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d each occurrence of which is the same as or different from and is independently selected from the group consisting of O, S, Se and NR N2 ; R a ,R b ,R c ,R N1 ,R N2 ,R C1 and R C2 each occurrence is independently selected from the group consisting of: Hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; The ligand L b and L c in the structure, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring; The substituents in the alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino are one or more selected from deuterium, halogen, unsubstituted alkyl having 1 - 20 carbon atoms, unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, unsubstituted heteroalkyl having 1 - 20 carbon atoms, unsubstituted heterocyclic group having 3 - 20 ring atoms, unsubstituted aralkyl having 7 - 30 carbon atoms, unsubstituted alkoxy having 1 - 20 carbon atoms, unsubstituted aryloxy having 6 - 30 carbon atoms, unsubstituted alkenyl having 2 - 20 carbon atoms, unsubstituted alkynyl having 2 - 20 carbon atoms, unsubstituted aryl having 6 - 30 carbon atoms, unsubstituted heteroaryl having 3 - 30 carbon atoms, unsubstituted alkylsilyl having 3 - 20 carbon atoms, unsubstituted arylsilyl having 6 - 20 carbon atoms, unsubstituted alkylgermyl having 3 - 20 carbon atoms, unsubstituted arylgermyl having 6 - 20 carbon atoms, unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

12. A composition comprising the compound according to any one of claims 1 - 7.

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