Organic electroluminescent materials and devices

Abstract

Disclosed are organic electroluminescent materials and devices thereof. The organic electroluminescent materials are compounds having a structure of Formula 1. These novel compounds can be applied to electroluminescent devices to provide better device performance, such as an increase in device life. Also disclosed are an electroluminescent device containing the compound and a compound composition containing the compound.

Description

Technical Field

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

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

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

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

[0005] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

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

[0007] The luminescent color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency and longer device life. Triazine organic semiconductor materials are widely used in OLEDs due to their superior optoelectronic properties, redox properties, stability, etc.

[0008] JP2017107992A discloses an organic compound having the following general structural formula and an organic light-emitting device comprising the compound: Wherein, X is oxygen or sulfur, R1 to R5 are independently hydrogen, alkyl, cyano or fluorine, and the disclosed specific structures are This application does not study or pay attention to the influence of R1 to R5 being aromatic groups on device performance.

[0009] KR20180068869A discloses an organic photoelectric device, wherein the light-emitting layer comprises two main bodies, one of which has a general structure of wherein R1 to R4 are independently hydrogen, C 6-60 Aryl, C 2-60 A heterocyclic group or a wherein Z1 to Z5 are independently N or CR6, R6 is selected from hydrogen, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C 2-60 Heteroaryl; R5 is C 2-60 A heterocyclic group or a And at least one of R1 to R5 is of the formula The application discloses the following compounds in specific structures: This application does not study and pay attention to the influence of the biphenyl group at the 6-position connecting the 4-biphenyl group and dibenzofuran on the device performance.

[0010] CN110268036A discloses an organic photoelectric device, wherein the light-emitting layer includes a compound having the following general structure: It is further disclosed that the compound has The application discloses the following compounds in the specific structure: This application focuses on compounds having substitution at the 8-position of dibenzofuran or substitution at both the 6-position and the 8-position, but does not study or pay attention to the effect of no substitution at the 8-position of dibenzofuran on device performance.

[0011] KR20180061075A discloses an organic compound having the following general structural formula and an organic light-emitting device comprising the compound: Wherein, X is O or S; A is or at least one Substituted C 6-60 Aryl or C2-60 heteroaryl containing 1 to 3 heteroatoms selected from N, O and S. The application discloses the following compounds in the specific structure: The application does not disclose compounds in which the substituents on the dibenzo five-membered heterocyclic ring are non-cyano substituted compounds, nor does it study or pay attention to the influence of the substituents on the dibenzo five-membered heterocyclic ring being non-cyano substituted aromatic groups on device performance.

[0012] CN108884086A discloses an organic compound having the following general structural formula and an organic light-emitting device comprising the compound: Wherein, Py is a substituted or unsubstituted C containing one nitrogen atom. 4-60 Heteroaryl, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-60 aryl, or a substituted or unsubstituted C2-60 heteroaryl containing 1 to 3 heteroatoms selected from N, O and S. It is further disclosed that the compound has the following structure: The application discloses the following compounds in specific structures: This application does not disclose or study compounds in which the substituents on the dibenzo five-membered heterocyclic ring are heteroaryl groups that do not contain nitrogen and their effects on device performance.

[0013] WO2019164218A1 discloses an organic compound having the following general structural formula and an organic light-emitting device comprising the compound: Wherein, W, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. The following compounds are disclosed in the specific structure: The application does not disclose compounds in which the substituents on the dibenzo five-membered heterocyclic ring are non-cyano substituted compounds, nor does it study or pay attention to the effect of the substituents on the dibenzo five-membered heterocyclic ring being non-cyano substituted aromatic groups on device performance.

[0014] WO2019231226A1 discloses an organic electronic device, wherein the light-emitting layer comprises two main bodies, one of which has the following general structure: Where X 2 For NL 7 -Ar 9 , O, S or CR'R", further disclosed that the host material has the following general formula: The following compounds are disclosed in the specific structure: This application does not study and pay attention to the compounds in which the 6-position of the diphenyl five-membered heterocyclic ring is an aromatic group and the 1-position triazine substituent is a (hetero) aromatic group substituted by a non-condensed ring heteroaryl group and its influence on the device performance. Summary of the invention

[0015] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the above problems. These novel compounds can be applied to organic electroluminescent devices and can provide better device performance, such as an increase in device life.

[0016] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0017]

[0018] in,

[0019] X is selected from O, S or Se;

[0020] n is selected from 1, 2, 3, 4 or 5;

[0021] X1-X5 are selected from CR in the same or different way each time they appear. x or N;

[0022] X6 is CH or CD;

[0023] W1-W4 are selected from CR in the same or different manner each time they appear. w or N;

[0024] Each time Z1-Z5 appears, they are selected from CR in the same or different way. z or N;

[0025] Ar is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0026] R and R y Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0027] R x , R w and R zEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0028] R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted An aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0029] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0030] Adjacent substituents R, R y and R w Can optionally be linked to form a ring.

[0031] 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, wherein the organic layer includes the compound described in the above embodiment.

[0032] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises the compound described in the above embodiment.

[0033] The present invention discloses a series of compounds having the structure of Formula 1. These novel compounds can be applied to organic electroluminescent devices and can provide better device performance, such as improving the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0035] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. DETAILED DESCRIPTION

[0036] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0037] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0038] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0039] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0040] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0041] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0042] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0043] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0044] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0045] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0046] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0047] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0048] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0049] Definition of Substituent Terms

[0050] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0051] Alkyl - as used herein, includes straight chain and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0052] Cycloalkyl - as used herein, includes cyclic alkyl. Cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, cycloalkyl can be optionally substituted.

[0053] Assorted alkyl - as used herein, assorted alkyl comprises one or more carbons in the alkyl chain and is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom and boron atom and is replaced by heteroatoms. Assorted alkyl can be an assorted alkyl with 1 to 20 carbon atoms, preferably an assorted alkyl with 1 to 10 carbon atoms, more preferably an assorted alkyl with 1 to 6 carbon atoms. The example of assorted alkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. Additionally, heteroalkyl groups can be optionally substituted.

[0054] Alkenyl - as used herein, encompasses straight chain, branched and cyclic olefin groups. Alkenyl can be an alkenyl containing 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, alkenyl groups may be optionally substituted.

[0055] Alkynyl - as used herein, encompasses straight chain alkynyl. Alkynyl may be an alkynyl containing 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl may be optionally substituted.

[0056] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0057] Heterocyclic or heterocyclic - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothioxolyl. Additionally, the heterocyclyl group may be optionally substituted.

[0058] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0059] Alkoxy-as used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy can be optionally substituted.

[0060] Aryloxy - as used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as above. Aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, aryloxy can be optionally substituted.

[0061] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0062] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0063] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyltert-butylsilyl, methylditert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0064] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0065] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be replaced by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted The invention also includes but is not limited to substituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0066] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0067] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0068] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0069] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0070] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

[0074] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0075]

[0076] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0077]

[0078] in,

[0079] X is selected from O, S or Se;

[0080] n is selected from 1, 2, 3, 4 or 5;

[0081] X1-X5 are selected from CR in the same or different way each time they appear. x or N;

[0082] X6 is CH or CD;

[0083] W1-W4 are selected from CR in the same or different manner each time they appear. w or N;

[0084] Each time Z1-Z5 appears, they are selected from CR in the same or different way. z or N;

[0085] Ar is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0086] R and R y Each occurrence, identically or differently, indicates mono-, poly- or non-substitution;

[0087] R x , R w and R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0088] R yEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted An aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0089] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0090] Adjacent substituents R, R y and R w Can optionally be linked to form a ring.

[0091] In this embodiment, "the adjacent substituents R, R y and R w "can be optionally linked to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R y Between the two substituents R w Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0092] According to one embodiment of the present invention, X is selected from O or S.

[0093] According to one embodiment of the present invention, wherein X is O.

[0094] According to an embodiment of the present invention, at least one of X1-X5 is N.

[0095] According to one embodiment of the present invention, X1-X5 are selected from CR x , where R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 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.

[0096] According to one embodiment of the present invention, R x Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and combinations thereof.

[0097] According to an embodiment of the present invention, at least one of W1-W4 is N.

[0098] According to one embodiment of the present invention, W1-W4 are selected from CR w , where R w Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 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.

[0099] According to one embodiment of the present invention, R wEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and combinations thereof.

[0100] According to an embodiment of the present invention, at least one of Z1-Z5 is N.

[0101] According to one embodiment of the present invention, Z1-Z5 are selected from CR Z , where R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 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.

[0102] According to one embodiment of the present invention, R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and combinations thereof.

[0103] According to one embodiment of the present invention, R and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms.

[0104] According to one embodiment of the present invention, R and R yEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and combinations thereof.

[0105] According to one embodiment of the present invention, R x , R Z Each occurrence is identically or differently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, or a combination thereof.

[0106] According to one embodiment of the present invention, R y , R w and R at each occurrence is identically or differently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted vinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, or a combination thereof.

[0107] According to one embodiment of the present invention, Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms.

[0108] According to one embodiment of the present invention, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, and combinations thereof; optionally, the hydrogen in the above groups can be partially or fully deuterated.

[0109] According to one embodiment of the present invention, Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, triphenylene, or a combination thereof; optionally, the hydrogen in the above groups can be partially or fully deuterated.

[0110] According to one embodiment of the present invention, n is selected from 1, 2 or 3.

[0111] According to one embodiment of the present invention, n is selected from 1 or 2.

[0112] According to one embodiment of the present invention, the compound is selected from the group consisting of compound A-1 to compound A-497, wherein the specific structures of compound A-1 to compound A-497 are described in claim 8.

[0113] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound described in any one of the aforementioned embodiments.

[0114] According to one embodiment of the present invention, the organic layer in the organic electroluminescent device is a light-emitting layer, the compound is a host compound, and the light-emitting layer contains at least a first metal complex.

[0115] According to one embodiment of the present invention, the first metal complex in the organic electroluminescent device has a structure represented by Formula 2:

[0116]

[0117] in,

[0118] The metal M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt;

[0119] A is selected, at each occurrence, identically or differently, from a substituted or unsubstituted aromatic ring having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;

[0120] L is selected from the group consisting of a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene having 5 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 5 to 30 carbon atoms, and combinations thereof at each occurrence; when two R' are present at the same time, the two R' are the same or different;

[0121] m is selected from 0 or 1 each time it appears, the same or different; when m=0, A and A are not connected;

[0122] Each occurrence of E is identically or differently selected from C or N;

[0123] X a each occurrence is identically or differently selected from a single bond, O or S;

[0124] R″ represents mono-, poly- or unsubstituted;

[0125] R', R" are each identically or differently 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 heterocyclyl 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 cycloalkyl having 6-30 carbon atoms, atom, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0126] Adjacent substituents R', R" may be optionally linked to form a ring.

[0127] In this embodiment, "adjacent substituents R', R" can be optionally connected to form a ring" is intended to mean that adjacent substituent groups, for example, between two substituents R', between two substituents R", between two substituents R' and R", any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents may not be connected to form a ring.

[0128] In this embodiment, when m is 0, it means that the corresponding L does not exist. For example, when there is an m that is 0, then formula 2 is When both m are 0, equation 2 is When the three m are 0, equation 2 is

[0129] According to one embodiment of the present invention, in Formula 2, at least one A is selected from a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms.

[0130] According to one embodiment of the present invention, in Formula 2, at least one A is selected from substituted or unsubstituted benzimidazole, benzoxazole, benzothiazole, and The dotted line coordinates with M.

[0131] According to one embodiment of the present invention, in Formula 2, at least one A is selected from a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms.

[0132] According to one embodiment of the present invention, in Formula 2, at least one A is selected from substituted or unsubstituted pyridine, and is coordinated with M through N of pyridine.

[0133] According to one embodiment of the present invention, in Formula 2, at least one, at least two, or at least three m's are not 0.

[0134] According to one embodiment of the present invention, in Formula 2, L is a single bond.

[0135] According to one embodiment of the present invention, in Formula 2, at least one X a It is O or S.

[0136] According to one embodiment of the present invention, in Formula 2, at least one X a It's O.

[0137] According to one embodiment of the present invention, the first metal complex has M(L a ) f (L b ) g (L c ) h The general formula, where L a It has the structure shown in Formula 3:

[0138]

[0139] in,

[0140] The metal M is selected, at each occurrence, identically or differently, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt;

[0141] L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the metal M, respectively. a , L b and L c can optionally be linked to form a multidentate ligand; for example, L a , L b and L c Any two of can be connected to form a tetradentate ligand; for example, L a , L b and L c can be connected to each other to form a hexadentate ligand; or for example, L a , L b , L c None of them are connected so as not to form a multidentate ligand;

[0142] f is selected from 0, 1, 2 or 3, g is selected from 0, 1, 2 or 3, h is selected from 0, 1 or 2;

[0143] When f is 2 or 3, multiple L a The same or different; when g is 2 or 3, multiple L b The same or different; when h is 2, the two L c Same or different;

[0144] Each occurrence of Q is the same or different and is selected from O, S, Se, NR q , CR q R q and SiR q R q When there are two R q When two R q Same or different;

[0145] Each time U1-U8 appears, it is selected from C, CR u or N; at least one of U5-U8 is C, and Connected, where "*" indicates the connection position;

[0146] U5, U6, U7 or U8 is connected to the metal M via a metal-carbon bond or a metal-nitrogen bond;

[0147] Each occurrence of V1-V4 is the same or different selection from CR v or N;

[0148] R q , R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0149] Adjacent substituent R q , R u and R v can optionally be linked to form a ring;

[0150] Among them, L b and L c Each occurrence is identically or differently selected from any one of the following groups:

[0151]

[0152]

[0153] in,

[0154] R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

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

[0156] R a , R b , R c , R N1 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0157] Adjacent substituent R a , R b , Rc , R N1 , R C1 and R C2 Can optionally be linked to form a ring.

[0158] In this context, “the adjacent substituent R q , R u and R v "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R q Between the two substituents R u Between the two substituents R v Between the two substituents R u and R v Between the two substituents R u and R q Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0159] In this embodiment, "the adjacent substituent R a , R b , R c , R N1 , R C1 and R C2 "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent R b and R C2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0160] According to an embodiment of the present invention, at least one of V1-V4 is N, for example, at least one or two Ns.

[0161] According to an embodiment of the present invention, at least one of U1-U8 is N, for example, at least one or two Ns.

[0162] According to another embodiment of the present invention, the ligand L a Having a structure represented by Formula 3a:

[0163]

[0164] in,

[0165] Each occurrence of Q is the same or different and is selected from O, S, Se, NR q , CR q R q and SiR q R q When there are two R q When two R q Can be the same or different;

[0166] Each occurrence of U1-U4 and U7-U8 is the same or different from CR u or N;

[0167] R v Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0168] R q , R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0169] Adjacent substituent R q , R u and R v Can optionally be linked to form a ring.

[0170] According to another embodiment of the present invention, the ligand L a Each occurrence is identically or differently selected from the structure represented by any one of the following structures:

[0171]

[0172] in,

[0173] Each occurrence of Q is the same or different and is selected from O, S, Se, NR q , CR q R q and SiR q R q When there are two R q When two R q Can be the same or different;

[0174] R u and R v Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0175] R q , R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0176] Adjacent substituent R q , R u and R v Can optionally be linked to form a ring.

[0177] According to another embodiment of the present invention, the first metal complex has a structure represented by Formula 4:

[0178]

[0179] in,

[0180] f is 0, 1, 2 or 3; when f is 2 or 3, multiple L a Same or different; when f is 0 or 1, multiple L b Same or different;

[0181] U4 is selected from CR each time it appears the same or different u or N;

[0182] Each occurrence of U1-U3 and U7-U8 is the same or different selection from CR u ;

[0183] R a , R b and R v Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0184] R a , R b , R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0185] Adjacent substituent R a , R b , R u and R v Can optionally be linked to form a ring.

[0186] According to one embodiment of the present invention, in Formula 3a and Formula 4, at least one of U1-U8 is selected from CR u , and R u It's cyano.

[0187] According to one embodiment of the present invention, in Formula 3a and Formula 4, at least one of U2-U4 is selected from CR u , and R u It's cyano.

[0188] According to one embodiment of the present invention, in Formula 3a and Formula 4, one of U3 and U4 is selected from CR u , and R u It's cyano.

[0189] According to one embodiment of the present invention, in Formula 3a and Formula 4, one of U2-U4 is selected from CR u , and R u is cyano; and at the same time, one of U1-U4 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 aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0190] According to one embodiment of the present invention, in Formula 3a and Formula 4, U4 is CR u , and R u is a substituted or unsubstituted phenyl group; and U3 is CR u , and R u It's cyano.

[0191] According to one embodiment of the present invention, in Formula 3a and Formula 4, U3 is CR u , and R u is a substituted or unsubstituted phenyl group; and U4 is CR u , and R u It's cyano.

[0192] According to one embodiment of the present invention, in Formula 3a and Formula 4, U3 is CR u , and R u is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; and U4 is CR u , and R u It's cyano.

[0193] According to one embodiment of the present invention, in Formula 3a and Formula 4, at least one of U1-U8 is selected from CR u , and R u It's fluorine.

[0194] According to one embodiment of the present invention, in Formula 3a and Formula 4, U3 is selected from CR u , and R u is fluorine; at the same time U1 is selected from CR u , and R u It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0195] In this embodiment, "the adjacent substituent R a , R b , R u and R v "can optionally be linked to form a ring" is intended to mean that adjacent groups of substituents, for example, two substituents R a Between the two substituents R b Between the two substituents R u Between the two substituents R v Between, the substituent R a and R b Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0196] According to one embodiment of the present invention, R u and R v Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring 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, and combinations thereof.

[0197] According to one embodiment of the present invention, at least one R u It is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0198] According to one embodiment of the present invention, at least one R u It's fluorine.

[0199] According to one embodiment of the present invention, at least one R u It's cyano.

[0200] According to one embodiment of the present invention, there are at least two R u , and one of the R u It is fluorine, another R uThe group is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0201] According to one embodiment of the present invention, there are at least two R u , and one of the R u is cyano, another R u The group is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0202] According to one embodiment of the present invention, wherein L a Each occurrence is selected from the group consisting of L a1-1 -L a1-114 , L a2-1 -L a2-83 , L a3-1 -L a3-73 and L a4-1 -L a4-82 The group consisting of L a1-1 -L a1-114 , L a2-1 -L a2-83 , L a3-1 -L a3-73 and L a4-1 -L a4-82 The specific structure is described in claim 17.

[0203] According to one embodiment of the present invention, wherein L b Each time it appears, choose the same or different one from L b1 -L b227 The group consisting of L b1 -L b227 The specific structure is described in claim 18.

[0204] According to one embodiment of the present invention, wherein L c Each time it appears, choose the same or different one from L b1 -L b227 The group consisting of L b1 -L b227 The specific structure is described in claim 18.

[0205] According to one embodiment of the present invention, the first metal complex has Ir(L a )2L b or IrLa (L b )2, where L a Each time it appears, choose the same or different one from L a1-1 -L a1-114 , L a2-1 -L a2-83 , L a3-1 -L a3-73 and L a4-1 -L a4-82 The group composed of L b Each time it appears, choose the same or different one from L b1 -L b227 The group consisting of a1-1 -L a1-114 , L a2-1 -L a2-83 , L a3-1 -L a3-73 and L a4-1 -L a4-82 The specific structure is described in claim 17, L b1 -L b227 The specific structure is described in claim 18.

[0206] According to one embodiment of the present invention, the first metal complex has Ir(L b )3 or Ir(L b )2L c or IrL b (L c )2, where L b Each time it appears, choose the same or different one from L b1 -L b227 The group composed of L c Each time it appears, choose the same or different one from L b1 -L b227 The group consisting of L b1 -L b227 The specific structure is described in claim 18.

[0207] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of GD1-1 to GD1-87, GD2-1 to GD2-84, GD3-1 to GD3-75, GD4-1 to GD4-86, GD5-1 to GD5-85, GD6-1 to GD6-46 and GD7-1 to GD7-28, wherein the specific structures of GD1-1 to GD1-87, GD2-1 to GD2-84, GD3-1 to GD3-75, GD4-1 to GD4-86, GD5-1 to GD5-80, GD6-1 to GD6-37 and GD7-1 to GD7-28 are described in claim 19.

[0208] According to one embodiment of the present invention, the light-emitting layer in the organic electroluminescent device further comprises a second main compound, and the second main compound comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylate, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0209] According to one embodiment of the present invention, the light-emitting layer in the organic electroluminescent device further comprises a second host compound, and the second host compound comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolecarbazole, fluorene, silylfluorene, and combinations thereof.

[0210] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by Formula 5:

[0211]

[0212] in,

[0213] L T Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0214] Each occurrence of T is selected from C, CR t or N;

[0215] R tEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0216] Ar1 is identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof at each occurrence;

[0217] Adjacent substituent R t Can optionally be linked to form a ring.

[0218] In this context, “the adjacent substituent R t can be optionally connected to form a ring”, is intended to mean that the substituent R t Any one or more of the adjacent substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0219] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by one of Formula 5-a to Formula 5-j:

[0220]

[0221] in,

[0222] L T Each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

[0223] Each occurrence of T is selected from C, CR t or N;

[0224] R t Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0225] Ar1 is identically or differently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof at each occurrence;

[0226] Adjacent substituent R t Can optionally be linked to form a ring.

[0227] According to an embodiment of the present invention, at least one of all Ts is selected from N, for example, one or two are N.

[0228] According to one embodiment of the present invention, a compound combination is also disclosed, which comprises the compound described in any of the aforementioned embodiments.

[0229] Combination with other materials

[0230] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0231] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of hosts, a variety of light-emitting dopants, transport layers, barrier layers, injection layers, electrodes, and other possible layers. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0232] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0233] Material synthesis example:

[0234] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0235] Synthesis Example 1: Synthesis of Compound A-1

[0236] Step 1: Synthesis of Intermediate C

[0237]

[0238] In a three-necked round-bottom flask, add A (24.4g, 116.5mmol), B (23.3g, 128.2mmol), Pd (PPh3) 4 (2.69g, 2.33mmol), Na2CO3 (24.7g, 223.0mmol) to ethylene glycol dimethyl ether (400mL), H2O (200mL), and heat under reflux overnight under nitrogen protection. After the reaction is complete, stop heating and cool to room temperature. Stand and separate, extract the aqueous phase with DCM several times, combine the organic phases, dry over anhydrous Na2SO4, filter, and concentrate under reduced pressure. The crude product is purified by column chromatography (PE / DCM = 2:1) to obtain a white solid intermediate C (30.7g, 115.1mmol) with a yield of 98.8%.

[0239] Step 2: Synthesis of Intermediate D

[0240]

[0241] In a single-mouth round-bottom flask, C (30.7 g, 115.1 mmol) was dissolved in DCM (300 mL), and BBr3 (109.6 g, 437.4 mmol) was slowly added to the system at 0°C. After the addition was completed, the temperature was gradually raised to room temperature and the reaction was allowed to proceed overnight. After the reaction was complete, the reaction solution was slowly poured into water, extracted several times, the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (PE / EA=4:1) to obtain a white solid intermediate D (26.8 g, 112.3 mmol) with a yield of 97.6%.

[0242] Step 3: Synthesis of Intermediate E

[0243]

[0244] In a three-necked round-bottom flask, add D (26.8 g, 112.3 mmol) and K2CO3 (38.8 g, 138.21 mmol) to DMF (360 mL), protect with nitrogen, heat to 140 ° C, and react overnight. After the reaction is complete, stop heating, cool to room temperature, pour the reaction solution into a large amount of water, add DCM, extract several times, combine the organic phases, dry over anhydrous Na2SO4, filter, and concentrate under reduced pressure. The crude product is purified by column chromatography (PE / EA = 5:1) to obtain white solid intermediate E (22.6 g, 103.4 mmol) with a yield of 92.0%.

[0245] Step 4: Synthesis of Intermediate F

[0246]

[0247] In a single-mouth round-bottom flask, E (22.6g, 103.4mmol) and pyridine (17.8g, 224.6mmol) were dissolved in DCM (400mL). Trifluoromethanesulfonic anhydride (38.0g, 134.8mmol) was slowly added to the system at 0°C. After the addition was completed, the system gradually warmed to room temperature and reacted overnight. After the reaction was complete, the reaction solution was poured into water, extracted several times, the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM=30:1) to obtain a white solid intermediate F (23.6g, 67.3mmol) with a yield of 65.1%.

[0248] Step 5: Synthesis of Intermediate G

[0249]

[0250] In a three-necked round-bottom flask, add F (11.4 g, 32.5 mmol), 4-biphenylboronic acid (7.72 g, 39.0 mmol), Pd (PPh3) 4 (0.75 g, 0.65 mmol), K2CO3 (9.0 g, 65.0 mmol) to toluene (140 mL), EtOH (35 mL), H2O (35 mL), and heat under reflux overnight under nitrogen protection. After the reaction is complete, stop heating and cool to room temperature. Stand and separate, extract the aqueous phase with DCM several times, combine the organic phases, dry over anhydrous Na2SO4, filter, and concentrate under reduced pressure. The crude product is purified by column chromatography (PE / DCM = 40:1 → 15:1) to obtain a white solid intermediate G (9.6 g, 27.06 mmol) with a yield of 83.3%.

[0251] Step 6: Synthesis of Intermediate H

[0252]

[0253] In a three-necked round-bottom flask, G (9.6 g, 27.06 mmol), biboronic acid pinacol ester (10.3 g, 40.58 mmol), Pd (OAc) 2 (0.18 g, 0.81 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3.HBF4, 0.60 g, 1.62 mmol), KOAc (5.3 g, 54.12 mmol) were added to 1,4-dioxane (110 mL), nitrogen was protected, and the mixture was heated under reflux overnight. After the reaction was complete, the heating was stopped, the mixture was cooled to room temperature, the reaction solution was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was purified by column chromatography (PE / DCM = 4:1 → 2:1) to obtain a light yellow solid intermediate H (8.5 g, 19.04 mmol) with a yield of 70.4%.

[0254] Step 7: Synthesis of Compound A-1

[0255]

[0256] In a three-necked round-bottom flask, H (4.0 g, 8.96 mmol), I (3.08 g, 8.96 mmol), Pd (PPh3) 4 (0.31 g, 0.27 mmol), K2CO3 (2.48 g, 17.92 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL), and the mixture was heated under reflux overnight under nitrogen protection. After the reaction was complete, the heating was stopped, the mixture was cooled to room temperature, and the mixture was filtered under reduced pressure. The obtained solid was washed with water and methanol in turn. The solid was recrystallized from toluene / acetonitrile to obtain a white solid (4.8 g, 7.65 mmol) with a yield of 85.3%. The product was confirmed to be the target product A-1 with a molecular weight of 627.2.

[0257] Synthesis Example 2: Synthesis of Compound A-19

[0258] Step 1: Synthesis of compound A-19

[0259]

[0260] In a three-necked round-bottom flask, H (3.36 g, 7.53 mmol), J (3.16 g, 7.53 mmol), Pd (PPh3) 4 (0.26 g, 0.226 mmol), K2CO3 (2.08 g, 15.06 mmol) were added to toluene (36 mL), EtOH (9 mL), and H2O (9 mL), and the mixture was heated under reflux overnight under nitrogen protection. After the reaction was complete, the heating was stopped, the mixture was cooled to room temperature, and the mixture was filtered under reduced pressure. The solid was washed with water and methanol in turn. The solid was recrystallized from toluene to obtain a white solid (4.3 g, 6.11 mmol) with a yield of 81.1%. The product was confirmed to be the target product A-19 with a molecular weight of 703.3.

[0261] Synthesis Example 3: Synthesis of Compound A-27

[0262] Step 1: Synthesis of Intermediate K

[0263]

[0264] In a multi-mouth round-bottom flask, add F (6.6g, 18.82mmol), 3-biphenylboronic acid (4.47g, 22.57mmol), Pd (PPh3) 4 (0.653g, 0.56mmol), K2CO3 (5.19g, 37.61mmol) to toluene (64mL), EtOH (16mL), H2O (16mL), and heat under reflux overnight under nitrogen protection. After the reaction is complete, stop heating and cool to room temperature. Stand and separate, extract the aqueous phase with DCM several times, combine the organic phases, dry over anhydrous Na2SO4, filter, and concentrate under reduced pressure. The crude product is purified by column chromatography (PE / DCM = 100:1→40:1) to obtain a white solid intermediate K (6.0g, 16.91mmol) with a yield of 89.8%.

[0265] Step 2: Synthesis of Intermediate L

[0266]

[0267] In a three-necked round-bottom flask, K (6.0 g, 16.91 mmol), biboronic acid pinacol ester (7.73 g, 30.44 mmol), Pd (OAc) 2 (0.19 g, 0.85 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3.HBF4, 0.623 g, 1.69 mmol), KOAc (3.32 g, 33.83 mmol) were added to 1,4-dioxane (85 mL), nitrogen was protected, and the mixture was heated under reflux overnight. After the reaction was complete, the heating was stopped, the mixture was cooled to room temperature, the reaction solution was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 8:1 → 1:1) to obtain a white solid intermediate L (4.8 g, 10.75 mmol) with a yield of 63.6%.

[0268] Step 3: Synthesis of Compound A-27

[0269]

[0270] In a three-necked round-bottom flask, add L (3.3 g, 7.4 mmol), I (2.54 g, 7.4 mmol), Pd (PPh3) 4 (0.256 g, 0.20 mmol), K2CO3 (2.04 g, 14.8 mmol) to toluene (32 mL), EtOH (8 mL), H2O (8 mL), and heat under reflux overnight under nitrogen protection. After the reaction is complete, stop heating, cool to room temperature, filter under reduced pressure, and rinse the obtained solid with water and methanol in turn. The solid is then recrystallized from toluene / acetonitrile to obtain a white solid (3.0 g, 4.8 mmol) with a yield of 64.9%. The product is confirmed to be the target product A-27 with a molecular weight of 627.2.

[0271] Synthesis Example 4: Synthesis of Compound A-45

[0272] Step 1: Synthesis of Compound A-45

[0273]

[0274] In a three-necked round-bottom flask, add L (3.3 g, 7.4 mmol), J (3.1 g, 7.4 mmol), Pd (PPh3) 4 (0.257 g, 0.22 mmol), K2CO3 (2.0 g, 14.8 mmol) to toluene (32 mL), EtOH (8 mL), H2O (8 mL), and heat under reflux overnight under nitrogen protection. After the reaction is complete, stop heating, cool to room temperature, filter under reduced pressure, and rinse the obtained solid with water and ethanol in turn. The solid is then recrystallized from toluene / acetonitrile to obtain a white solid (4.1 g, 5.8 mmol) with a yield of 78.8%. The product is confirmed to be the target product A-45 with a molecular weight of 703.3.

[0275] Synthesis Example 5: Synthesis of Compound A-3

[0276] Step 1: Synthesis of intermediate M

[0277]

[0278] In a three-necked round-bottom flask, G (2.5 g, 7.06 mmol) was dissolved in THF (80 mL). Under nitrogen protection, sec-butyl lithium (1 M, 8.5 mmol) was slowly added to the system at -78 °C. After the addition was complete, the reaction was kept at low temperature for 1 hour. 1 mL of deuterium chloride aqueous solution (20%) was added, and the temperature was slowly raised to room temperature and the reaction was allowed to proceed overnight. After the reaction was completed, the solvent was removed under reduced pressure, and the solid was recrystallized from ethanol to obtain a white solid intermediate M (2 g, 5.63 mmol) with a yield of 80%.

[0279] Step 2: Synthesis of Intermediate N

[0280]

[0281] In a three-necked round-bottom flask, M (4.4 g, 12.4 mmol), biboronic acid pinacol ester (4.72 g, 18.6 mmol), Pd (OAc) 2 (56 mg, 0.25 mmol), 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (SPhos, 204 mg, 0.5 mmol), KOAc (3.65 g, 37.2 mmol) were added to 1,4-dioxane (125 mL), nitrogen was protected, and heated to reflux overnight. Stop heating, cool to room temperature, filter the system through diatomaceous earth, and concentrate the filtrate under reduced pressure. The crude product was purified by column chromatography (PE / DCM = 2:1) to obtain a white solid intermediate N (2.2 g, 4.9 mmol) with a yield of 40%.

[0282] Step 3: Synthesis of compound A-3

[0283]

[0284] In a three-necked round-bottom flask, N (2.2 g, 4.9 mmol), I (1.69 g, 4.9 mmol), Pd (PPh 3) 4 (114 mg, 0.1 mmol), K 2 CO 3 (1.36 g, 9.8 mmol) were added to toluene (40 mL), EtOH (5 mL), and H 2 O (5 mL), and the mixture was heated under reflux overnight under nitrogen protection. After the reaction was complete, the heating was stopped, the mixture was cooled to room temperature, and the mixture was filtered under reduced pressure. The obtained solid was washed with water and methanol in turn. The solid was recrystallized from toluene / acetonitrile to obtain a white solid (2.8 g, 4.46 mmol) with a yield of 91%. The product was confirmed to be the target product A-3 with a molecular weight of 628.2.

[0285] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0286] Device Embodiment

[0287] Device Example 1

[0288] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8In the case of 1000 Å / s, the ITO anode is sequentially evaporated by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound H1 is used as an electron blocking layer (EBL). Then compound GD4-59 is doped in compound H1 and compound A-1 of the present invention, and co-evaporation is used as a light-emitting layer (EML). Compound H2 is used as a hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-evaporated as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0289] Device Example 2

[0290] Device Example 2 was prepared the same as Device Example 1, except that Compound A-19 was used instead of Compound A-1 in the emissive layer (EML).

[0291] Device Example 3

[0292] Device Example 3 was prepared the same as Device Example 1, except that Compound A-27 was used instead of Compound A-1 in the emissive layer (EML).

[0293] Device Example 4

[0294] Device Example 4 was prepared the same as Device Example 1, except that Compound A-45 was used instead of Compound A-1 in the emissive layer (EML).

[0295] Device Example 5

[0296] The preparation of Device Example 5 was the same as that of Device Example 1, except that Compound GD2-81 was used in the emission layer (EML) instead of Compound GD4-59, and H1:A-1:GD2-81=56:38:6.

[0297] Device Example 6

[0298] The preparation of Device Example 6 was the same as that of Device Example 1, except that Compound GD2-82 was used in the emission layer (EML) instead of Compound GD4-59, and H1:A-1:GD2-82=56:38:6.

[0299] Device Example 7

[0300] The preparation of Device Example 7 was the same as that of Device Example 1, except that Compound GD2-18 was used in the emission layer (EML) instead of Compound GD4-59, and H1:A-1:GD2-18=56:38:6.

[0301] Device Example 8

[0302] The preparation of Device Example 8 was the same as that of Device Example 1, except that Compound GD2-83 was used in the emission layer (EML) instead of Compound GD4-59, and H1:A-1:GD2-83=56:38:6.

[0303] Device Example 9

[0304] The preparation of Device Example 9 was the same as that of Device Example 1, except that Compound GD2-84 was used in the emission layer (EML) instead of Compound GD4-59, and H1:A-1:GD2-84=56:38:6.

[0305] Device Comparison Example 1

[0306] The preparation of device Comparative Example 1 was the same as that of device Example 1, except that compound C-1 was used instead of compound A-1 in the emission layer (EML).

[0307] Device Comparison Example 2

[0308] The preparation of device Comparative Example 2 was the same as that of device Example 1, except that compound C-2 was used instead of compound A-1 in the emission layer (EML).

[0309] Device Comparison Example 3

[0310] The preparation of device Comparative Example 3 was the same as that of device Example 1, except that compound C-3 was used instead of compound A-1 in the emission layer (EML).

[0311] Device Comparison Example 4

[0312] The preparation of device Comparative Example 4 was the same as that of device Example 1, except that compound C-4 was used instead of compound A-1 in the emission layer (EML).

[0313] Device Comparison Example 5

[0314] The preparation of device Comparative Example 5 was the same as that of device Example 1, except that compound C-5 was used instead of compound A-1 in the emission layer (EML).

[0315] Device Comparison Example 6

[0316] The preparation of device Comparative Example 6 was the same as that of device Example 1, except that compound C-6 was used instead of compound A-1 in the emission layer (EML).

[0317] Device Comparison Example 7

[0318] The preparation of device Comparative Example 7 was the same as that of device Example 1, except that compound C-7 was used instead of compound A-1 in the emission layer (EML).

[0319] Device Comparison Example 8

[0320] The preparation of device Comparative Example 8 was the same as that of device Example 1, except that compound C-8 was used instead of compound A-1 in the emission layer (EML).

[0321] The detailed device layer structure and thickness are shown in the table below. For layers using more than one material, different compounds are doped in the weight ratios recorded.

[0322] Table 1 Device structures of device embodiments and comparative examples

[0323]

[0324]

[0325] The material structure used in the device is shown below:

[0326]

[0327]

[0328] Table 2 shows that at 15 mA / cm 2 CIE data and current efficiency measured under constant current; and at 80mA / cm 2 Device lifetime measured at constant current (LT95).

[0329] Table 2 Device data of Examples 1 to 9 and Comparative Examples 1 to 8

[0330]

[0331]

[0332] discuss:

[0333] In Examples 1 to 4 and Comparative Example 1, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-1 of the present invention, respectively. Compared with Comparative Example 1, the device current efficiency of Examples 1 to 4 is equivalent to that of the Comparative Example, but their device lifespans are increased by 31.9%, 34.6%, 35.6% and 59.4%, respectively. This indicates that the aryl-substituted compound having a phenyl group substituted at the 6-position of the dibenzopentacyclic ring of the present invention has a longer device lifespan when applied to an electroluminescent device, compared with the compound having only a phenyl group substituted at the 6-position.

[0334] In Examples 1 to 4 and Comparative Example 2, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-2 of the present invention, respectively. Compared with Comparative Example 2, the device current efficiency of Examples 1 to 4 is equivalent to that of the Comparative Example, but their device lifespans are increased by 44.8%, 47.7%, 48.9% and 75.0%, respectively. This indicates that the compounds of the present invention having a bi(hetero)aryl substitution on the triazine have a longer device lifespan when applied to electroluminescent devices, compared with the compounds having a single aryl substitution on the triazine.

[0335] In Examples 1 to 4 and Comparative Example 3, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-3 of the present invention, respectively. Compared with Comparative Example 3, the device current efficiency of Examples 1 to 4 is equivalent to that of the Comparative Example, but their device lifespans are increased by 40.9%, 43.8%, 44.9% and 70.4%, respectively. This indicates that the compound of the present invention having a para-connected bi(hetero)aryl group on triazine has a longer device lifespan when applied to an electroluminescent device than the compound having a meta-connected bi(hetero)aryl group on triazine.

[0336] In Examples 1 to 4 and Comparative Example 4, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-4 of the present invention, respectively. Compared with Comparative Example 4, the device current efficiency of Examples 1 to 4 is equivalent to that of the Comparative Example, but their device lifespans are increased by 33.8%, 36.6%, 37.6% and 61.8%, respectively. The compound having a bi(hetero)aryl substitution at the 6th position of the dibenzopentacyclic ring of the present invention has a longer device lifespan when applied to an electroluminescent device, compared with the compound having a bi(hetero)aryl substitution at the 8th position of the dibenzopentacyclic ring.

[0337] In Examples 1 to 4 and Comparative Example 5, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-5 of the present invention, respectively. Compared with Comparative Example 5, the device current efficiency of Examples 1 to 4 is improved, and their device lifespans are improved by 27.9 times, 28.5 times, 28.8 times and 34 times, respectively. It is shown that the (hetero)aryl substituted compound having a phenyl substitution at the 6-position of the dibenzo pentacyclic heterocycle of the present invention has a longer device lifespan when applied to an electroluminescent device than the (hetero)aryl substituted compound having a heteroaryl substitution at the 6-position of the dibenzo pentacyclic heterocycle.

[0338] In Examples 1 to 4 and Comparative Example 6, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-6 of the present invention, respectively. Compared with Comparative Example 6, the device current efficiency of Examples 1 to 4 is improved, and their device lifespans are improved by 81.0%, 84.7%, 86.1% and 118.8%, respectively. It is shown that the compound having a (hetero) aromatic group substituted with a non-cyano substituted phenyl group of the present invention has a longer device lifespan when applied to an electroluminescent device, compared with the compound having a (hetero) aromatic group substituted with a cyano substituted phenyl group.

[0339] In Examples 1 to 4 and Comparative Example 7, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-7 of the present invention, respectively. Compared with Comparative Example 7, the device current efficiency of Examples 1 to 4 is equivalent to that of the comparative example, but their device lifespans are increased by 19.1%, 21.5%, 22.4% and 43.9%, respectively. It is shown that the compound of the present invention having a terminal six-membered (hetero)aryl substituted on the triazine has a longer device lifespan when applied to an electroluminescent device, compared with the compound having a terminal condensed ring heteroaryl substituted on the triazine.

[0340] In Examples 1 to 4 and Comparative Example 8, the phosphorescent dopant GD4-59 is doped in the compounds A-1, A-19, A-27, A-45 of the present invention and the non-compound C-8 of the present invention, respectively. Compared with Comparative Example 8, the device current efficiency of Examples 1 to 4 is equivalent to that of the comparative example, but their device lifespans are increased by 39.4%, 42.2%, 43.3% and 68.5%, respectively. It is shown that the (hetero)aryl substituted compound having a phenyl substitution at the 6-position of the dibenzo pentacyclic heterocyclic ring of the present invention has a longer device lifespan when applied to an electroluminescent device, compared with the compound having a condensed ring (hetero)aryl substituted at the 6-position of the dibenzo pentacyclic heterocyclic ring.

[0341] In Examples 5 to 9, different phosphorescent dopants were used to dope the compound A-1 of the present invention, and the devices all showed higher current efficiency and longer lifespan, indicating that the compound of the present invention can be matched with a wide range of phosphorescent dopants and obtain excellent device performance.

[0342] In summary, when the compound of the present invention is used as the main material of the light-emitting layer, the electron and hole transport balance ability of the material is improved. Compared with the case where the compound not of the present invention is used as the main material of the light-emitting layer, the device performance is improved, wherein the current efficiency of the device is equivalent to or improved to that of the comparative example, and the life of the device is significantly improved. This is of great help to the industry.

[0343] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure of Formula 1: in, X is selected from O or S; n is selected from 1 or 2; X1-X5 are selected from CR in the same or different way each time they appear. x ; X6 is CH or CD; W1-W4 are selected from CR in the same or different manner each time they appear. w ; Each time Z1-Z5 appears, they are selected from CR in the same or different way. z ; Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms; R and R y Each occurrence, identically or differently, indicates mono-, poly- or non-substitution; R x each occurrence being identically or differently selected from the group consisting of: hydrogen, deuterium; R z is selected, at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, phenyl; R w , R y and R, at each occurrence, is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted vinyl, substituted or unsubstituted aryl having 6 to 12 carbon atoms; The substituted alkyl, substituted vinyl, and substituted aryl are substituted by one or more selected from deuterium and halogen; Two substituents R can be optionally connected to form a monocyclic aromatic ring. y can be optionally connected to form a monocyclic aromatic ring, two adjacent substituents R w can be optionally linked to form a monocyclic aromatic ring; The compound is not 2. The compound according to claim 1, wherein X is O.

3. The compound according to claim 1 or 2, wherein X1-X5 are selected from CR in the same or different way each time they appear. x , and Z1-Z5 are selected from CR Z , where R x Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium; R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, phenyl.

4. The compound according to claim 1 or 2, wherein R x Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium; R z Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, fluorine.

5. The compound of claim 1 or 2, wherein the substituted alkyl, substituted vinyl, substituted aryl is substituted by one or more deuterium.

6. The compound according to claim 1 or 2, wherein W1-W4 are selected from CR in the same or different manner each time they appear. w , where R w , R and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted vinyl, substituted or unsubstituted aryl having 6 to 12 carbon atoms.

7. The compound according to claim 1 or 2, wherein R w , R and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, vinyl, and substituted or unsubstituted aryl having 6 to 12 carbon atoms.

8. The compound of claim 1 or 2, wherein R w , R and R y is selected, on each occurrence identically or differently, from hydrogen, deuterium, fluorine, substituted or unsubstituted vinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl.

9. The compound according to claim 1 or 2, wherein Ar is selected from substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms; wherein R x Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium; R z Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms; R w , R and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms.

10. The compound of claim 1 or 2, wherein Ar is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene; optionally, the hydrogen in the above groups can be partially or fully deuterated.

11. The compound according to claim 1 or 2, wherein n is selected from 1.

12. The compound according to claim 1, wherein The compound is selected from the group consisting of:

13. An organic electroluminescent device, comprising: An anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to any one of claims 1 to 12.

14. The organic electroluminescent device according to claim 13, wherein: The organic layer is a light-emitting layer, the compound is a host compound, and the light-emitting layer at least contains a first metal complex.

15. The organic electroluminescent device according to claim 14, wherein: The light-emitting layer also contains a second main compound, which contains at least one chemical group selected from the following group: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylate, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, and azaphenanthrene.

16. The organic electroluminescent device according to claim 15, wherein: The second host compound comprises at least one chemical group selected from the group consisting of benzene, carbazole, indolecarbazole, fluorene, and silylfluorene.

17. A compound combination comprising the compound according to any one of claims 1 to 12.

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