Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure shown in a formula 1, and the compound can be used as an electron blocking material, a hole transport material or a main body material in an organic electroluminescent device. According to the compound, the efficiency or the service life of the device can be remarkably improved while the low voltage of the organic light-emitting device is maintained, and better comprehensive performance of the device can be provided. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

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 light-emitting device and a compound 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 light-emitting device that included an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as an electron-transporting 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 the cathode and the 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 in the fabrication of 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 small singlet-triplet energy gaps, making it possible for excitons to return from triplets to singlets. 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 precise structures, small molecules can have large molecular weights. Dendrimers with well-defined structures 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 turn into polymer OLEDs.

[0006] There are various OLED manufacturing methods. Small molecule OLEDs are usually fabricated 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 solvents, small molecule OLEDs can also be fabricated 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 color 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, more saturated emission spectra, higher efficiency, and longer device lifetimes are desired.

[0008] The performance of organic electroluminescent devices, such as efficiency and lifespan, is significantly related to the balance of carrier concentrations in the light-emitting layer. By designing the molecular structures of charge transport materials and carrier blocking materials, the balance of carrier concentrations in the light-emitting layer can be more reasonably regulated. Currently, the existing materials that can be used in the hole transport layer still have various problems, such as short lifespan, low efficiency, and poor comprehensive performance.

[0009] CN106883145 discloses a compound with a structure, and the compound structure must contain an acenaphthylene fragment, and the compound is applied as a hole transport material in an electroluminescent device. This application does not disclose compounds with other structures, nor does it disclose or teach the influence of the compound as other materials on the device performance.

[0010] With the increasing demand for the performance of organic electroluminescent devices in the industry, OLED materials with excellent properties such as low voltage, high efficiency, and long lifespan still need to be further studied and developed. Summary of the Invention

[0011] The present invention aims to provide a series of novel triarylamine compounds containing specific conjugated polycycles represented by Formula 1 to solve at least part of the above problems. The compounds can be used in organic electroluminescent devices, such as electron blocking materials and hole transport materials. When these novel compounds are applied to organic electroluminescent devices, they can significantly improve the device efficiency or lifespan while maintaining low voltage, providing better comprehensive device performance.

[0012] According to an embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0013]

[0014] In Formula 1,

[0015] Ar 1 and Ar 2 each occurrence is independently selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, or a combination thereof;

[0016] L, L 1 ,L 2 each occurrence is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms, or a combination thereof;

[0017] X 1 -X 5 each occurrence is independently selected from C, CR x1or N, and X 1 -X 5 One of which is selected from C and is linked to L; X 6 -X 10 Each occurrence is the same as or different from and is selected from CR x2 or N;

[0018] Y 1 -Y 8 Each occurrence is the same as or different from and is selected from CR y or N;

[0019] R x1 R x2 R y Each occurrence of R is the same as or different from 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 alkynyl 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, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0020] Adjacent substituents R x1 Can optionally be linked to form a ring;

[0021] Adjacent substituents R x2 Can optionally be linked to form a ring;

[0022] Adjacent substituents R y Can optionally be linked to form a ring;

[0023] Adjacent substituents R can optionally be linked to form a ring.

[0024] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound described in the foregoing embodiment.

[0025] According to another embodiment of the present invention, a compound composition is also disclosed, and the compound composition contains the compound described in the foregoing embodiment.

[0026] The present invention discloses a series of compounds simultaneously containing a specific conjugated polycycle and a triarylamine structure represented by the formula 1 structure. The compounds can be used in organic light-emitting devices, for example, as an electron blocking material, a hole transporting material, etc., and can improve the performance of organic light-emitting devices. For example, while maintaining a low voltage, the device efficiency or lifespan can be significantly improved, and the comprehensive performance of the device can be enhanced. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 is a schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein.

[0028] Figure 2 is another schematic diagram of an organic light-emitting device that can contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0029] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 Schematically and non-limitingly shows an organic light-emitting device 100. The figure is not necessarily drawn to scale, and some layer structures in the figure can also be omitted as needed. The 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. The 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, and the entire content of the above patent is incorporated herein by reference.

[0030] 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 doped with F at a molar ratio of 50:1 4m-MTDATA of -TCNQ, 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. U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties, disclose examples of cathodes that include a composite cathode having a thin metal layer such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of the blocking layer 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 entireties. Examples of the injection layer 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.

[0031] 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 layers of different light-emitting materials to achieve the desired emission spectrum.

[0032] 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.

[0033] The OLED also requires a encapsulation layer, such as Figure 2 Schematically and non-limitingly shows an 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.

[0034] Devices fabricated in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) incorporating the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination 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.

[0035] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0036] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless the first layer is "in contact with" the second layer, other layers can be present between the first and second layers. For example, even though various organic layers are present between the cathode and the anode, the cathode can still be described as "disposed on" the anode.

[0037] 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.

[0038] 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.

[0039] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can be exceeded by delayed fluorescence by more than 25% of the spin statistical limit. 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).

[0040] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the 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 known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of the singlet excited state refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of electro-generated excitons.

[0041] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-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 highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (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) with an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0042] Definition of substituent terms

[0043] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0044] 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.

[0045] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl, 1 - adamantyl, 2 - adamantyl, 1 - norbornyl, 2 - norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, and 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0046] Heteroalkyl - as used herein, heteroalkyl is formed by replacing one or more carbons in an alkyl chain with heteroatoms 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 heteroalkyl 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.

[0047] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - 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.

[0048] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylacetylenyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0049] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-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-tetraphenylyl. Additionally, the aryl can be optionally substituted.

[0050] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and 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 can be optionally substituted.

[0051] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups having 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Heteroaryl also refers to heteroaromatic group. The heteroaryl can 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 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and their nitrogen - containing analogues. Additionally, the heteroaryl can be optionally substituted.

[0052] Alkoxy - As used herein, it is represented by - O - alkyl, - O - cycloalkyl, - O - heteroalkyl or - O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocycloalkyl 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, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0053] 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.

[0054] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0055] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0056] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0057] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0058] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0059] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. 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. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0060] In the present disclosure, unless otherwise defined, when any one of the following terms is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, 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, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, 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 heterocycloalkyl 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, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0061] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered equivalent.

[0062] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0063] Among the compounds mentioned in the present disclosure, multiple substitution refers to the range including double substitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates multiple substitution (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.

[0064] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally connect to form a ring, otherwise adjacent substituents in the compound cannot connect to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally connect to form a ring, which includes both the case where adjacent substituents can connect to form a ring and the case where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including 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.

[0065] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0066]

[0067] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0068]

[0069] The expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away connecting to each other through a chemical bond to form a ring, which can be exemplified by the following formula:

[0070]

[0071] In addition, the expression that adjacent substituents can optionally connect to form a ring is also intended to be considered as referring to, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0072]

[0073] According to an embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0074]

[0075] In Formula 1,

[0076] Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof;

[0077] L, L 1 , L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;

[0078] X 1 -X 5 are each independently selected from C, CR x1 or N, and one of X 1 -X 5 is selected from C and is connected to L; X 6 -X 10 are each independently selected from CR x2 or N;

[0079] Y 1 -Y 8 are each independently selected from CR y or N;

[0080] R x1 , R x2 , R y, each occurrence of R 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 alkynyl 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;

[0081] Adjacent substituents R x1 can optionally be linked to form a ring;

[0082] Adjacent substituents R x2 can optionally be linked to form a ring;

[0083] Adjacent substituents R y can optionally be linked to form a ring;

[0084] Adjacent substituents R can optionally be linked to form a ring.

[0085] As used herein, "adjacent substituents R x1 can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, two adjacent substituents R x1 can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring.

[0086] As used herein, "adjacent substituents R x2 can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, two adjacent substituents R x2 can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring.

[0087] As used herein, "adjacent substituents R y can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups on the same six-membered ring, for example, Y1 -Y 4 Two adjacent substituents R in y can be connected to form a ring, and / or Y 5 -Y 8 Two adjacent substituents R in six of y can be connected to form a ring. Obviously, these substituents may also not be connected to form a ring at all.

[0088] In this article, "adjacent substituents R can optionally be connected to form a ring" is intended to mean a group of adjacent substituents among them. For example, two adjacent substituents R can be connected to form a ring. Obviously, these substituents may also not be connected to form a ring at all.

[0089] According to an embodiment of the present invention, wherein the R x1 and R x2 cannot be connected to form a ring.

[0090] According to an embodiment of the present invention, wherein the R and R y cannot be connected to form a ring.

[0091] According to an embodiment of the present invention, wherein the R x1 , R x2 , R y are the same or different each time they appear and are 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 alkynyl 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 group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

[0092] According to an embodiment of the present invention, wherein the compound has a structure represented by Formula 1-1 or Formula 1-2:

[0093]

[0094] Ar 1 and Ar 2 each occurrence is the same as or different from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof;

[0095] L, L 1 , L 2 each occurrence is the same as or different from a single bond, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 30 carbon atoms, or a combination thereof;

[0096] X 1 -X 5 each occurrence is the same as or different from CR x1 or N; X 6 -X 10 each occurrence is the same as or different from CR x2 or N;

[0097] Y 1 -Y 8 each occurrence is the same as or different from CR y or N;

[0098] R x1 , R x2 , R y , each occurrence of R is the same as or different 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 alkynyl 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;

[0099] adjacent substituents Rx1 can optionally be connected to form a ring;

[0100] Adjacent substituents R x2 can optionally be connected to form a ring;

[0101] Adjacent substituents R y can optionally be connected to form a ring;

[0102] Adjacent substituents R can optionally be connected to form a ring.

[0103] According to an embodiment of the present invention, wherein the L, L 1 , L 2 each occurrence is the same or different and is selected from a single bond, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof.

[0104] According to an embodiment of the present invention, wherein the L, L 1 , L 2 are the same or different and are selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylenofluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenophenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, or a combination thereof.

[0105] According to an embodiment of the present invention, wherein the L, L 1 , L 2 are the same or different and are selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, or a combination thereof.

[0106] According to an embodiment of the present invention, wherein the L, L 1 , L 2 are both selected from a single bond.

[0107] According to an embodiment of the present invention, wherein the X 1 -X 5 each occurrence is the same or different and is selected from CR x1 , the X 6 -X 10 each occurrence is the same or different and is selected from CR x2 .

[0108] According to one embodiment of the present invention, wherein said Y 1 -Y 8 is the same as or different from each occurrence and is independently selected from CR y .

[0109] According to one embodiment of the present invention, wherein said X 1 -X 5 is the same as or different from each occurrence and is independently selected from CR x1 , and said X 6 -X 10 is the same as or different from each occurrence and is independently selected from CR x2 ; and said Y 1 -Y 8 is the same as or different from each occurrence and is independently selected from CR y .

[0110] According to one embodiment of the present invention, wherein said R x1 , R x2 , R y is the same as or different from each occurrence and is independently selected from 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, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or a combination thereof.

[0111] According to one embodiment of the present invention, wherein said R x1 , R x2 , R y is the same as or different from each occurrence and is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, or a combination thereof.

[0112] According to one embodiment of the present invention, wherein said R x1 , R x2 , R y is the same as or different from each occurrence and is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, or a combination thereof.

[0113] According to one embodiment of the present invention, wherein said R is the same as or different from each occurrence and is independently selected from 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, or a combination thereof.

[0114] According to one embodiment of the present invention, each occurrence of R is the same or different and is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0115] According to one embodiment of the present invention, each occurrence of R is the same or different and is selected from methyl, phenyl, or a combination thereof.

[0116] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is the same or different and is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.

[0117] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is the same or different and is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted silylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, or a combination thereof.

[0118] According to one embodiment of the present invention, wherein the Ar 1 and Ar 2 Each occurrence is the same or different and is selected from the group consisting of G1 to G120:

[0119]

[0120]

[0121]

[0122] According to one embodiment of the present invention, wherein at least one of the Ar 1 or Ar 2 is selected from a substituted or unsubstituted fluorenyl group.

[0123] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound 1 to Compound 2024, Compound C1 to Compound C131. For the specific structures of Compound 1 to Compound 2024 and Compound C1 to Compound C131, refer to Claim 10.

[0124] According to an embodiment of the present invention, in the structures of Compounds 1 to 2024 and Compounds C1 to C131, the hydrogen can be partially or completely replaced by deuterium.

[0125] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes: an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound described in any of the foregoing embodiments.

[0126] According to an embodiment of the present invention, in the organic electroluminescent device, the organic layer is an electron blocking layer, a hole transporting layer, or a light emitting layer.

[0127] According to an embodiment of the present invention, wherein the organic layer is an electron blocking layer, and the compound is an electron blocking material.

[0128] According to an embodiment of the present invention, wherein the thickness of the electron blocking layer is between 1 nm and 500 nm.

[0129] According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, and the compound is a host material.

[0130] According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes: an anode, a cathode, a hole injection layer, a hole transporting layer, an electron blocking layer, and a light emitting layer, and the electron blocking layer contains the compound described in any of the foregoing embodiments.

[0131] According to an embodiment of the present invention, wherein the electron blocking layer is in direct contact with the hole transporting layer; the electron blocking layer is in direct contact with the light emitting layer.

[0132] According to an embodiment of the present invention, the hole transporting layer contains a hole transporting material, and the hole transporting material contains a mono-triarylamine compound or a bis-triarylamine compound.

[0133] According to an embodiment of the present invention, wherein the organic layer contains a light emitting layer, and the light emitting layer contains a phosphorescent material.

[0134] According to an embodiment of the present invention, the light emitting layer contains a phosphorescent material.

[0135] According to an embodiment of the present invention, wherein the phosphorescent material is a metal complex, and the metal complex has the general formula of M(L a ) m (L b ) n (L c ) q of the general formula;

[0136] Among them, the metal M is selected from metals with a relative atomic mass greater than 40;

[0137] L a 、L b and L c are the first ligand, the second ligand, and the third ligand coordinated with the metal M respectively, and L a 、L b 、L c can be the same or different;

[0138] L a 、L b and L c can optionally be connected to form a polydentate ligand;

[0139] m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c can be the same or different;

[0140] The ligand L a has the structure shown in Formula 3:

[0141]

[0142] Among them,

[0143] Ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0144] Ring F is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0145] Ring D and Ring F are fused via U a and U b ;

[0146] U a and U b are the same or different each time they appear and are selected from C or N;

[0147] R d ,R f are the same or different each time they appear and represent mono-substitution, multi-substitution, or no substitution;

[0148] U 1 -U 4 are the same or different each time they appear and are selected from CR u or N;

[0149] R d ,R f ,R uEach 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0150] Adjacent substituents R d , R f , R u can optionally be joined to form a ring;

[0151] Ligand L b , L c Each occurrence is the same or different and is selected from the group consisting of the following structures:

[0152]

[0153] wherein,

[0154] R a , R b and R c Each occurrence is the same or different and represents mono-substitution, multi-substitution, or no substitution;

[0155] X b Each occurrence is the same or different and is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0156] X c and X d Each occurrence is the same or different and is selected from the group consisting of: O, S, Se and NR N2 ;

[0157] R a , R b, R c , R N1 , R N2 , R C1 and R C2 are each independently selected, each time they appear, 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 alkynyl 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;

[0158] Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be joined to form a ring.

[0159] As used herein, adjacent substituents R d , R f , R u can optionally be joined to form a ring, which is intended to mean that when there are substituents R d , substituent R f , substituent R u , among which adjacent substituent groups, such as between adjacent substituents R d , between adjacent substituents R f , between adjacent substituents R u , between adjacent substituents R d and R f , between adjacent substituents R d and R u , and between adjacent substituents R f and R uAmong them, any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, when there are substituents R d , substituent R f , substituent R u , these substituent groups may also not be connected to form a ring.

[0160] In this embodiment, the 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 the adjacent substituent groups among them. For example, between two substituents R a , between two substituents R b , between two substituents R c , between substituent R a and R b , between substituent R a and R c , between substituent R b and R c , between substituent R a and R N1 , between substituent R b and R N1 , between substituent R a and R C1 , between substituent R a and R C2 , between substituent R b and R C1 , between substituent R b and R C2 , between substituent R a and R N2 , between substituent R b and R N2 , and between R C1 and R C2 , any one or more of these substituent groups can be connected to form a ring. For example, the adjacent substituents R a , R b in can optionally be connected to form a ring, which can form one or more of the following structures including but not limited to: Among them, W is selected from O, S, Se, NR w or CR w R w ; where the R w , R a ’, Rb The definition of ’ is the same as that of R a Obviously, these substituents may also not be connected to each other to form a ring.

[0161] According to an embodiment of the present invention, in Formula 3, two R f are connected to form a ring.

[0162] According to an embodiment of the present invention, in Formula 3, two R f are connected to form a 5-membered unsaturated carbon ring, a 5-membered heteroaryl ring or a 6-membered aryl ring.

[0163] According to an embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaryl ring, and ring F is a benzene ring or a 6-membered heteroaryl ring.

[0164] According to an embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaryl ring, and ring F is a 5-membered heteroaryl ring or a 5-membered unsaturated carbon ring.

[0165] According to an embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaryl ring, and ring F is a benzene ring or a 6-membered heteroaryl ring, and two R f are connected to form a ring, which is a 6-membered aryl ring or a 6-membered heteroaryl ring.

[0166] According to an embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaryl ring, and ring F is a 5-membered heteroaryl ring or a 5-membered unsaturated carbon ring, and two R f are connected to form a 6-membered aryl ring or a 6-membered heteroaryl ring.

[0167] According to an embodiment of the present invention, in Formula 3, at least two of U 1 -U 4 are selected from CR u , and the two R u are connected to form a ring.

[0168] According to an embodiment of the present invention, in Formula 3, U 3 and U 4 are selected from CR u , and the two R u are connected to form a ring.

[0169] According to an embodiment of the present invention, in Formula 3, U 3 and U 4 are selected from CR v , and the two R u are connected to form a 6-membered aryl ring or a 6-membered heteroaryl ring.

[0170] According to an embodiment of the present invention, in Formula 3, R d , R f , Ru At least one or two sets of adjacent substituents are connected to form a ring. For example, two substituents R d are connected to form a ring, or two substituents R f are connected to form a ring, or two substituents R u are connected to form a ring, or the substituent R d and the substituent R f are connected to form a ring, or the substituent R d and the substituent R u are connected to form a ring, or the substituent R f and the substituent R u are connected to form a ring, or two substituents R d are connected to form a ring while two substituents R f are connected to form a ring, or two substituents R d are connected to form a ring while two substituents R u are connected to form a ring, or two substituents R f are connected to form a ring while two substituents R u are connected to form a ring, the substituent R f and the substituent R u are connected to form a ring while 2 substituents R u are connected to form a ring, or the substituent R d and the substituent R u are connected to form a ring while 2 substituents R u are connected to form a ring; R d 、R f 、R u have a similar situation when more sets of adjacent substituents are connected to form a ring.

[0171] According to an embodiment of the present invention, wherein the ligand L b has the following structure:

[0172]

[0173] Wherein, R Ⅰ to R ⅦEach 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 alkynyl 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.

[0174] According to one embodiment of the present invention, wherein R Ⅰ -R Ⅲ at least one of which is selected from 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, or combinations thereof; and / or R Ⅳ -R Ⅵ at least one of which is selected from 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, or combinations thereof.

[0175] According to one embodiment of the present invention, wherein R Ⅰ -R Ⅲ at least two of which are the same or different each time they appear and are selected from 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, or combinations thereof; and / or R Ⅳ -R Ⅵ at least two of which are the same or different each time they appear and are selected from 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, or combinations thereof.

[0176] According to one embodiment of the present invention, wherein RⅠ -R Ⅲ At least two of them are the same or different each time they appear and are selected from a substituted or unsubstituted alkyl group having 2-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2-20 carbon atoms, or a combination thereof; and / or R Ⅳ -R Ⅵ At least two of them are the same or different each time they appear and are selected from a substituted or unsubstituted alkyl group having 2-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2-20 carbon atoms, or a combination thereof.

[0177] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is an Ir complex, a Pt complex or an Os complex.

[0178] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent light-emitting material is an Ir complex and has Ir(L a )(L b )(L c ), Ir(L a ) 2 (L b ), Ir(L a )(L b ), 2 , Ir(L a ), 2 (L c ), or Ir(L a )(L c ) 2 Any of the structures shown.

[0179] According to an embodiment of the present invention, wherein the ligand L a has a 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.

[0180] According to an embodiment of the present invention, in the organic electroluminescent device, the ligand L a has a 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.

[0181] According to an embodiment of the present invention, in the electroluminescent device, the ligand L a is the same or different each time it appears and is selected from any one of the groups consisting of the following structures:

[0182]

[0183]

[0184]

[0185] According to an embodiment of the present invention, in the electroluminescent device, the ligand L b is the same or different each time it appears and is optionally selected from any one of the group consisting of the following structures:

[0186]

[0187] According to an embodiment of the present invention, wherein, in the electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] According to an embodiment of the present invention, a compound composition is disclosed, which comprises the compound described in any one of the foregoing embodiments.

[0199] In combination with other materials

[0200] The materials for specific layers in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the devices. 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.

[0201] The materials described herein as being specific layers useful 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.

[0202] In the examples of material synthesis, unless otherwise specified, 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 chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeters from Shimadzu, fluorescence spectrophotometers 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 being affected, the above relevant content will not be elaborated further in this patent.

[0203] Examples of material synthesis:

[0204] 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:

[0205] Synthesis Example 1: Synthesis of Compound 1817

[0206] Step 1: Synthesis of Intermediate B

[0207]

[0208] Under nitrogen protection, intermediate A (10.6 g, 35.57 mmol) was added to THF (450 mL), and the temperature was lowered to -72 °C. n-Butyllithium (n-BuLi, 2.5 M, 15.65 mL, 39.13 mmol) was dropped into the reaction solution, and the reaction was carried out at -72 °C for 4 hours. Intermediate SM1 (10.2 g, 39.13 mmol) and THF (30 mL) were dropped into the reaction solution, and the reaction was carried out at -72 °C for half an hour, and then the reaction was continued at room temperature for half an hour. The reaction solution was quenched with saturated ammonium chloride aqueous solution, extracted with ethyl acetate, and concentrated under reduced pressure to obtain intermediate B, which was directly used in the next step without further purification.

[0209] Step 2: Synthesis of intermediate C

[0210]

[0211] Intermediate B was added to acetic acid (AcOH, 150 mL) / concentrated HCl (40 mL), and the reaction was refluxed for 6 hours. The reaction was monitored by TLC and was found to be complete. The reaction solution was poured into ice water, filtered, the filtrate was concentrated and purified by column chromatography to obtain intermediate C (11.5 g, overall yield of two steps 70%).

[0212] Step 3: Synthesis of compound 1817

[0213]

[0214] Under nitrogen protection, intermediate SM2 (2.39 g, 5.95 mmol), intermediate C (2.5 g, 5.41 mmol), and sodium tert-butoxide (t-BuONa, 1.10 g, 11 mmol) were added to a 500 mL two-necked reaction flask, and toluene (160 mL) was added. Pd(OAc) 2 (24.3 mg, 0.108 mmol) and SPhos (2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl, 177 mg, 0.432 mmol) were added, and the temperature was raised to 120 °C, and the reaction was carried out overnight. The reaction solution was filtered through diatomaceous earth, washed thoroughly with dichloromethane, the filtrate was concentrated and purified by column chromatography to obtain the product compound 1817 (2.77 g, yield 65.4%). The product was confirmed to be the target product with a molecular weight of 783.39.

[0215] Synthesis Example 2: Synthesis of compound 1823

[0216] Step 1: Synthesis of compound 1823

[0217]

[0218] Under nitrogen protection, the intermediate SM3 (2.25 g, 4.29 mmol), intermediate C (1.8 g, 3.9 mmol), and sodium tert-butoxide (768 mg, 8 mmol) were added to a 500 mL two-neck reaction flask, toluene (160 mL) was added, and Pd 2 (dba) 3 (36 mg, 0.039 mmol) and SPhos (80 mg, 0.195 mmol) were added. The temperature was raised to 120 °C and the reaction was carried out overnight. The reaction solution was filtered through diatomaceous earth, washed thoroughly with dichloromethane, the filtrate was concentrated and purified by column chromatography to obtain the product compound 1823 (2.0 g, yield 56.4%). The product was confirmed to be the target product with a molecular weight of 907.42.

[0219] 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.

[0220] The preparation method of the organic electroluminescent device is not limited. The preparation method of the following device examples is only an example and should not be construed as a limitation. Those skilled in the art can reasonably improve the preparation method of the following device examples based on the prior art.

[0221] Device Example

[0222] Device Example 1: Preparation of an organic electroluminescent device.

[0223] First, a 0.7 mm thick glass substrate with pre-patterned thick indium tin oxide (ITO) as the anode was used. After washing the substrate with deionized water and detergent, the ITO surface was treated with oxygen plasma and UV ozone. Subsequently, the substrate was dried in a glove box to remove moisture and loaded into a holder and transferred into a vacuum chamber. The following specified organic layers were deposited on the anode layer by vacuum thermal evaporation in sequence at a rate of -6 under a vacuum of about 10 Torr: First, compound HT-1 and compound HT-2 were co-evaporated as the hole injection layer (HIL, weight ratio 98:2, thickness ), compound HT-1 was evaporated as the hole transport layer (HTL, thickness ), the compound 1817 of the present invention was evaporated as the electron blocking layer (EBL, thickness ), and then compound RH and compound RD were co-evaporated as the emitting layer (EML, weight ratio 98:2, thickness ). Compound HB was evaporated as the hole blocking layer (HBL, thickness ), the compounds ET and Liq are co-deposited as the electron transport layer (ETL, weight ratio 40:60, thickness ), and Liq with a thickness of is thermally evaporated as the electron injection layer (EIL). Finally, metal Al is thermally evaporated as the cathode (Cathode, thickness ). Then, the device is transferred back to the glove box and encapsulated with a glass cover slip to complete the device.

[0224] Device Example 2

[0225] The preparation method of Device Example 2 is the same as that of Device Example 1, except that Compound 1823 of the present invention is used instead of Compound 1817 of the present invention in the electron blocking layer.

[0226] Device Comparative Example 1

[0227] The preparation method of Device Comparative Example 1 is the same as that of Device Example 1, except that Compound EB-1 is used instead of Compound 1817 of the present invention in the electron blocking layer.

[0228] Device Comparative Example 2

[0229] The preparation method of Device Comparative Example 2 is the same as that of Device Example 1, except that Compound EB-2 is used instead of Compound 1817 of the present invention in the electron blocking layer.

[0230] Device Comparative Example 3

[0231] The preparation method of Device Comparative Example 3 is the same as that of Device Example 1, except that Compound EB-3 is used instead of Compound 1817 of the present invention in the electron blocking layer.

[0232] The detailed device layer structures and thicknesses are shown in Table 1 below. For the layers in which more than one material is used, they are doped with different compounds in the recorded weight ratios.

[0233] Table 1 Partial device structures of Examples 1-2 and Comparative Examples 1-3

[0234]

[0235] The material structures used in the device are as follows:

[0236]

[0237]

[0238] Table 2 summarizes and shows the device performances of Examples 1-2 and Comparative Examples 1-3. Among them, the voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) are measured at a current density of 15 mA / cm 2 .

[0239] Table 2 Device Data of Examples 1-2 and Comparative Examples 1-3

[0240]

[0241] Discussion:

[0242] Compound 1817 and Compound 1823 of the present invention used in Examples 1 and 2 are compounds represented by Formula 1 that contain both a specific conjugated polycycle and a triarylamine structure. Compound EB-1, Compound EB-2, and Compound EB-3 used in Comparative Examples 1 to 3 do not have the specific conjugated polycycle of this application and are a type of known compounds that can be used as electron blocking materials.

[0243] As can be seen from the data in Table 2, when comparing Example 1 with Comparative Example 1, the voltage of Example 1 remains comparable, both at a low voltage level. At the same time, the current efficiency is increased by 17.8%, the power efficiency is increased by 15.6%, and the external quantum efficiency is increased by 13.4%. This shows that the compound represented by Formula 1 of the present invention, which contains both a specific conjugated polycycle and a triarylamine structure, can provide better device performance when applied to the device compared to Comparative Example Compound EB-1 that does not have the specific conjugated polycycle of this application.

[0244] When comparing Example 1 with Comparative Example 2, with the voltage being comparable, the current efficiency, power efficiency, and external quantum efficiency all have a small increase. More importantly, the lifetime of Example 1 is 20 times that of Comparative Example 2 (40 hours vs. 2 hours, LT95 lifetime measured under the condition of a current density of 80 mA / cm 2 ). This shows that the compound represented by Formula 1 of the present invention, which contains both a specific conjugated polycycle and a triarylamine structure, can provide better device performance when applied to the device.

[0245] When comparing Example 2 with Comparative Example 3, the voltage is reduced by 0.2 V, the current efficiency is significantly increased by 30.6%, the power efficiency is greatly increased by 36.1%, and the external quantum efficiency is greatly increased by 35%. Moreover, based on the already high lifetime of Comparative Example 3, the lifetime of Example 2 is further significantly increased by 47.6% (62 hours vs. 42 hours, LT95 lifetime measured under the condition of a current density of 80 mA / cm 2 ). This kind of increase is very rare. It once again shows that the compound represented by Formula 1 of the present invention, which contains both a specific conjugated polycycle and a triarylamine structure, has more excellent performance when applied to an organic electroluminescent device compared to the comparative example compounds that do not have the specific conjugated polycycle of this application.

[0246] In summary, when the compound with the structure of Formula 1 according to the present invention is applied to an organic electroluminescent device, it can significantly improve the current efficiency, power efficiency, and external quantum efficiency while maintaining a low voltage, or significantly improve the device lifetime, achieving a substantial improvement in comprehensive performance. This indicates that the triarylamine compound containing a specific conjugated polycycle according to the present invention has excellent properties and unique advantages of low voltage and high efficiency / long lifetime, predicting its broad prospects in commercial applications.

[0247] 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: In Formula 1, Ar 1 and Ar 2 each occurrence is the same or different and is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof; L, L 1 , L 2 each occurrence being the same or different and being selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; X 1 -X 5 is the same as or different from each occurrence and is selected from C, CR x1 or N, and X 1 -X 5 one of which is selected from C and is connected to L; X 6 -X 10 is the same as or different from each occurrence and is selected from CR x2 or N; Y 1 -Y 8 each occurrence being the same as or different from, independently selected from CR y or N; R x1 ,R x2 ,R y , each occurrence of R 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, 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 alkynyl 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; Adjacent substituents R x1 may optionally be linked to form a ring; Adjacent substituents R x2 can optionally be linked to form a ring; Adjacent substituents R y can optionally be linked to form a ring; Adjacent substituents R can optionally be joined to form a ring.

2. The compound according to claim 1, wherein the compound has a structure represented by Formula 1-1 or Formula 1-2: Ar 1 and Ar 2 each occurrence is the same as or different from, and is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; L, L 1 , L 2 each occurrence is the same as or different from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof; X 1 -X 5 each occurrence is the same as or different from and is selected from CR x1 or N; X 6 -X 10 each occurrence is the same as or different from and is selected from CR x2 or N; Y 1 -Y 8 each occurrence being the same or different and independently selected from CR y or N; R x1 ,R x2 ,R y , each occurrence of R is the same as or different from one another 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 alkynyl 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 x1 may optionally be joined to form a ring; Adjacent substituents R x2 can optionally be linked to form a ring; Adjacent substituents R y can optionally be linked to form a ring; Adjacent substituents R can optionally be joined to form a ring.

3. The compound according to claim 1, wherein, Said L, L 1 , L 2 each occurrence of which is the same as or different from and is independently selected from a single bond, a substituted or unsubstituted arylene having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene having 3-20 carbon atoms, or a combination thereof; Preferably, the L, L 1 , L 2 is the same as or different from each other and is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylenefluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenophenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted pyrenylene, or a combination thereof; More preferably, said L, L 1 , L 2 is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, or a combination thereof each time it appears; Most preferably, said L, L 1 , L 2 are all selected from single bonds.

4. The compound according to claim 1, wherein, said X 1 -X 5 is the same as or different from each occurrence and is independently selected from CR x1 ; said X 6 -X 10 is the same as or different from each occurrence and is independently selected from CR x2 ; and / or said Y 1 -Y 8 is the same as or different from each occurrence and is independently selected from CR y .

5. The compound according to claim 1, wherein, Said R x1 , R x2 , R y is the same as or different from each other each time it appears and is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof; Preferably, said R x1 , R x2 , R y is the same as or different from each other each time it appears and is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, or a combination thereof.

6. The compound according to claim 1, wherein, Each occurrence of R is the same or different and is selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof; Preferably, each occurrence of R is the same or different and is selected from a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, or a combination thereof; More preferably, each occurrence of R is the same or different and is selected from methyl, phenyl, or a combination thereof.

7. The compound according to claim 1, wherein, Said Ar 1 and Ar 2 are each independently selected, each time they appear, from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof; Preferably, the Ar 1 and Ar 2 are each independently selected, each time they appear, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or a combination thereof.

8. The compound according to claim 1, wherein, said Ar 1 or Ar 2 each occurrence being the same as or different from one another and selected from the group consisting of G1 to G102:

9. The compound according to claim 1, wherein, The Ar 1 or Ar 2 wherein at least one is selected from substituted or unsubstituted fluorenyl groups.

10. The compound according to claim 8, wherein, The compound is selected from the group consisting of Compound 1 to Compound 2024, and Compound C1 to Compound C131; wherein, Compound 1 to Compound 2024 have a structure represented by Formula 2, wherein, Ar 1 , Ar 2 are each independently selected from the groups listed in the following table: The specific structures of Compound C1 to Compound C131 are as follows: wherein, "Ph" in the compound represents a phenyl group; Optionally, the hydrogen in the structures of Compound 1 to Compound 2024, and Compound C1 to C131 can be partially or completely replaced by deuterium.

11. An organic electroluminescent device, which comprises: An anode, A cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1-10.

12. The organic electroluminescent device according to claim 11, wherein, The organic layer is an electron blocking layer, a hole transporting layer or a light emitting layer; Preferably, the organic layer is an electron blocking layer and the compound is an electron blocking material.

13. A compound composition comprising the compound according to any one of claims 1-10.

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