Organic electroluminescent material and device thereof

Abstract

Organic electroluminescent materials and devices thereof are disclosed. These organic electroluminescent materials are compounds having the structure of Formula 1. These novel compounds can be applied in organic electroluminescent devices, such as as host materials or transport materials (e.g., electron transport materials), providing better device performance, especially improved device lifetime. An organic electroluminescent device comprising this compound and a compound composition comprising this compound are also disclosed.

Description

Technical Field

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

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

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

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

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

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

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] CN113993863A discloses an organic compound with the following formula and an organic light-emitting device containing said compound: Wherein N-Het is a C2 to C60 heterocyclic group, either substituted or unsubstituted, containing one or more N atoms; Z1 is a C6 to C60 aryl group, either substituted or unsubstituted, or represented by chemical formula A. Where X1 represents O, S, and CR. 11 R 12 or NR 13 The application further discloses the following compounds: This application does not disclose or teach compounds having the structure of Formula 1, nor their application in organic electroluminescent devices.

[0009] WO2020009381A1 discloses an organic compound of the following formula and an organic light-emitting device comprising said compound: Where X1 to X5 each appear in the same or different ways, representing N or CR, and one of X1 to X5 is N; A is a substituent represented by the following formula 2: Wherein Y is selected from O, S, or CR3R4. This application further discloses the following compounds: This application discloses compounds having a structure of Formula 2 and a triazine connected by a bridging group containing a pyridyl group, but does not disclose or teach compounds having a structure of Formula 1, or their application in organic electroluminescent devices.

[0010] CN113260615A discloses an organic compound with the following formula and an organic light-emitting device comprising said compound: Where X is O, S, or NR 21 Ar is a substituted or unsubstituted aryl, heteroaryl, or amino group; N-Het is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing one or more N atoms. This application further discloses the following compounds: This application only discloses compounds having a benzodibenzofuran (thiophene or carbazole) skeleton structure, and does not disclose or teach such compounds having a dibenzofuran (thiophene or carbazole) skeleton structure, especially not the compounds having the structure of Formula 1 in this application, and their application in organic electroluminescent devices.

[0011] WO2019132632A1 discloses an organic compound of the following formula and an organic light-emitting device comprising said compound: Among them, Ar 1 Aryl groups, C6 to C60, with or without substitution; 2 and Ar 3 All are selected from any of the following structures: Where X is O or S. This application further discloses the following compounds: This application only discloses compounds containing two dibenzofurans (or thiophenes) and does not disclose or teach compounds containing fluorene groups, especially compounds having the structure of Formula 1, or their applications in organic electroluminescent devices.

[0012] CN111247650A discloses an organic light-emitting device, wherein the organic layer comprises an organic compound having the following general structural formula: In this compound, at least one of X1 to X3 is N, and the remainder is CH. The application further discloses the following compounds: This application does not disclose or teach compounds having the structure of Formula 1, especially compounds having substituents at specific positions on dibenzofurans, particularly compounds having the structure of Formula 1 in this application, and their applications in organic electroluminescent devices. Summary of the Invention

[0013] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the problems mentioned above. These novel compounds can be applied in organic electroluminescent devices, for example, as host materials, transport materials (e.g., electron transport materials) in organic electroluminescent devices, and can provide better device performance, especially improved device lifetime.

[0014] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0015]

[0016] X is selected from O, S, or Se;

[0017] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0018] Y1-Y5 are selected from CR each time they appear, either the same or different. y Or N;

[0019] Z1-Z8 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z4 is selected from C and connected to L2;

[0020] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0021] L1, each time it appears, is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0022] L2 is selected, in the same or different ways, from single-bonded, substituted or unsubstituted aryl groups with 6-30 carbon atoms each time it appears;

[0023] R, R x and R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0024] R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The group includes alkynyl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0025] Adjacent substituents R can optionally connect to form a ring;

[0026] Adjacent substituent R z They can be arbitrarily connected to form a loop;

[0027] Adjacent substituent R y They can be optionally linked to form carbon rings or heterocycles containing one or more of N, Si, P, Ge, and B atoms.

[0028] According to another 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 at least one layer of the organic layer comprises the compound described in the foregoing embodiments.

[0029] According to another embodiment of the present invention, a compound composition comprising the compounds described in the foregoing embodiments is also disclosed.

[0030] This invention discloses a series of compounds having the structure of Formula 1. These novel compounds can be applied in organic electroluminescent devices, providing better device performance, especially improved device lifetime, and significantly enhancing the overall performance of the device. Attached Figure Description

[0031] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0032] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. Detailed Implementation

[0033] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0034] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a 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 also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0035] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0036] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0037] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0038] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0039] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0040] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0041] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0042] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0043] 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: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0044] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0045] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0046] Definition of the term "substituent group"

[0047] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0048] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0049] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0050] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0051] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups 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, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0052] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 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, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0053] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-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-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0054] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. 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, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. 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 ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0055] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0056] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0057] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0058] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0059] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 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, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0060] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0061] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0062] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

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

[0064] In this disclosure, unless otherwise defined, the term "substituted alkyl", "substituted cycloalkyl", "substituted heteroalkyl", "substituted heterocyclic", "substituted aralkyl", "substituted alkoxy", "substituted aryl", "substituted alkenyl", "substituted alkynyl", "substituted heteroaryl", "substituted alkylsilyl", "substituted arylsilyl", "substituted alkylgermanium", "substituted arylgermanium", "substituted amino", "substituted acyl", "substituted carbonyl", "substituted carboxyl" are used interchangeably. Acid group, substituted ester group, substituted sulfinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine. One or at least two of these groups may be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having 3-20 carbon atoms. Cycloalkyl groups with 1-20 carbon atoms, unsubstituted heteroalkyl groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

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

[0066] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0067] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0068] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0069] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0070]

[0071] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0072]

[0073] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0074]

[0075] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0076]

[0077] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0078]

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

[0080] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0081] Y1-Y5 are selected from CR each time they appear, either the same or different. y Or N;

[0082] Z1-Z8 are selected from C and CR each time they appear, either identically or differently. z Or N, and one of Z1-Z4 is selected from C and connected to L2;

[0083] Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0084] L1, each time it appears, is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0085] L2 is selected, in the same or different ways, from single-bonded, substituted or unsubstituted aryl groups with 6-30 carbon atoms each time it appears;

[0086] R, R x and R zEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0087] R y Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. The group includes alkynyl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0088] Adjacent substituents R can optionally connect to form a ring;

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

[0090] Adjacent substituent R yThey can be optionally linked to form carbon rings or heterocycles containing one or more of N, Si, P, Ge, and B atoms.

[0091] In this document, "adjacent substituents R can optionally connect to form a ring" is intended to mean that two adjacent substituents R can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0092] In this paper, "adjacent substituent R" z "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, any two substituents R z Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0093] In this paper, "adjacent substituent R" y "Can be optionally linked to form a carbocyclic ring or a heterocyclic ring containing N, Si, P, Ge, and B atoms" is intended to indicate adjacent substituent groups, for example, any two substituents R y Between these substituent groups, any one or more of them can be linked to form a ring, which can be a carbocyclic ring (aromatic or non-aromatic) or a heterocyclic ring (aromatic or non-aromatic), and the heterocyclic ring contains at least one or more of N, Si, P, Ge, and B atoms. Obviously, these substituents may also not be linked to form a ring.

[0094] According to one embodiment of the present invention, the adjacent substituent R y They can be optionally linked to form carbon rings.

[0095] According to one embodiment of the present invention, wherein adjacent substituents R y They can be optionally linked to form aromatic carbon rings.

[0096] According to one embodiment of the present invention, the adjacent substituent R y They can be arbitrarily linked to form aromatic rings.

[0097] According to one embodiment of the present invention, X is selected from O or S.

[0098] According to one embodiment of the present invention, X is O.

[0099] According to one embodiment of the present invention, X1-X6 are selected from CR each time they appear, either identically or differently. x .

[0100] According to one embodiment of the present invention, X1-X6 are selected from CR each time they appear, either identically or differently. xOr N, and at least one of X1-X6 is selected from N, for example, one or two of X1-X6 are selected from N.

[0101] According to one embodiment of the present invention, Z1-Z8 are selected from C or CR each time they appear, either identically or differently. z And one of Z1-Z4 is selected from C and connected to L2.

[0102] According to one embodiment of the present invention, Z3 or Z4 is selected from C and connected to L2.

[0103] According to one embodiment of the present invention, Z1-Z8 are selected from C and C respectively each time they appear, either identically or differently. z Or N, and one of Z1-Z4 is selected from C and connected to L2; wherein at least one of Z1-Z8 is selected from N, for example, one or two of Z1-Z8 are selected from N.

[0104] According to one embodiment of the present invention, L1 is selected, in the same or different ways, from single-bonded, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0105] According to one embodiment of the present invention, L1 is selected, in the same or different ways, from single-bonded, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, or combinations thereof.

[0106] According to one embodiment of the invention, L1, each time it appears, is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, or combinations thereof.

[0107] According to one embodiment of the invention, L1 is selected from single bonds, or substituted or unsubstituted phenylenes, each time it appears.

[0108] According to one embodiment of the present invention, L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms each time it appears.

[0109] According to one embodiment of the present invention, L2 is selected from single bonds, substituted or unsubstituted aryl groups having 6-12 carbon atoms each time it appears.

[0110] According to one embodiment of the invention, L2 is selected, each time it appears, from the same or different single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or a combination thereof.

[0111] According to one embodiment of the invention, L2 is selected from single bonds, or substituted or unsubstituted phenylenes, each time it appears.

[0112] According to one embodiment of the present invention, R x R y R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0113] According to one embodiment of the present invention, R x R y R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.

[0114] According to one embodiment of the present invention, R x R y R z Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, cyano groups, and combinations thereof.

[0115] According to one embodiment of the present invention, R x R y R z Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

[0116] According to one embodiment of the invention, R is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, and combinations thereof.

[0117] According to one embodiment of the invention, R is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, and combinations thereof, each time R appears.

[0118] According to one embodiment of the invention, R is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups having 6-12 carbon atoms, and combinations thereof, each time it appears.

[0119] According to one embodiment of the invention, R, each time appearing, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.

[0120] According to one embodiment of the invention, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0121] According to one embodiment of the invention, Ar is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, or combinations thereof.

[0122] According to one embodiment of the invention, Ar, each time it appears, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and combinations thereof.

[0123] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds A-1 to A-566, wherein the specific structures of compounds A-1 to A-566 are shown in claim 9.

[0124] According to one embodiment of the present invention, the hydrogen in compounds A-1 to A-566 can be partially or completely replaced by deuterium.

[0125] 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 at least one layer of the organic layer comprises a compound as described in any of the preceding embodiments.

[0126] According to one embodiment of the present invention, the organic layer containing the compound is an electron transport layer, and the compound is an electron transport compound.

[0127] According to one embodiment of the present invention, the organic layer containing the compound is a light-emitting layer, the compound is a host compound, and the light-emitting layer contains at least a first metal complex.

[0128] According to an embodiment of the present invention, the first metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0129] Metal M is selected from metals with a relative atomic mass greater than 40;

[0130] ligand L a L b and L c The first ligand, second ligand, and third ligand, respectively, are coordinated with the metal M, and ligand L is... a L b and L c They can be the same or different;

[0131] ligand L a L b and L cThey can be optionally linked to form polydentate ligands; for example, L a L b and L c Any two of them can be connected to form a tetradentate ligand; for example, L a L b and L c They can connect to form hexadecantal ligands; or, for example, L a L b and L c They are not connected and therefore do not form multidentate ligands;

[0132] m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q equals the oxidation state of metal M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different; when q is 2, the two Ls c They can be the same or different;

[0133] ligand L a It has the structure shown in Equation 2:

[0134]

[0135] When ring C1 and ring C2 appear in the same or different ways, they are selected from aromatic rings having 5-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof;

[0136] Q1 and Q2 are selected from C or N each time they appear, either the same or different.

[0137] R 11 and R 12 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0138] R 11 and R 12Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0139] Adjacent substituent R 11 R 12 They can be arbitrarily connected to form a loop;

[0140] ligand L b and L c Each occurrence may be the same or different, selected from monoanionic bidentate ligands.

[0141] According to one embodiment of the present invention, wherein the ligand L b and L c Each occurrence is either identical or different and selected from the group consisting of the following structures:

[0142]

[0143] in,

[0144] R a and R b Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0145] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0146] X c and X dEach time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0147] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0148] Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0149] In this embodiment, "adjacent substituent R" a R b R c R N1 R N2 R C1 and R C2 "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a Between the two substituents R b Between, substituent R a and R b Between, substituent Ra and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, and R C1 and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0150] According to one embodiment of the present invention, the first metal complex has Ir(L a ) m (L b ) 3-m The general formula structure, and by

[0151] The structure represented by Equation 3:

[0152]

[0153] in,

[0154] m can be 0, 1, 2, or 3; when m is 2 or 3, multiple L a Same or different; multiple L when m is 0 or 1 b Same or different;

[0155] T1-T6 each time appear in the same or different selections from CR T Or N;

[0156] R a R b and R d Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0157] R a R b R d and R TEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0158] Adjacent substituent R a R b They can be arbitrarily connected to form a loop;

[0159] Adjacent substituent R d R T They can be arbitrarily connected to form a ring.

[0160] In this embodiment, "adjacent substituent R" a R b "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R a Between the two substituents R b Between, and substituent R a and R b Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0161] In this embodiment, "adjacent substituent R" d R T "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R T Between the two substituents R d Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0162] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T And the R T It is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.

[0163] According to one embodiment of the present invention, at least one of T1-T6 is selected from CR T And the R T Selected from fluorine or cyano groups.

[0164] According to one embodiment of the present invention, at least two of T1-T6 are selected from CR T And one of the R T Selected from fluorine or cyano, another R T It is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.

[0165] According to one embodiment of the present invention, T1-T6 are selected from CR each time they occur, either identically or differently. T Or N, and at least one of T1-T6 is selected from N, for example, one or two of T1-T6 are selected from N.

[0166] According to one embodiment of the present invention, the first metal complex is selected from the group including but not limited to GD1 to GD76, wherein the specific structures of GD1 to GD76 are as follows:

[0167]

[0168]

[0169]

[0170] According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a second host compound, the second host compound comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0171] According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a second host compound, the second host compound comprising at least one chemical group selected from the group consisting of benzene, carbazole, indolecarbazole, fluorene, silylfluorene, and combinations thereof.

[0172] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by Formula 3:

[0173]

[0174] in,

[0175] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0176] T is selected from C and CR each time it appears, either identically or differently. t Or N;

[0177] R t Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0178] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0179] Adjacent substituent R t They can be arbitrarily connected to form a ring.

[0180] In this paper, "adjacent substituent R" t "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, any two substituents R t Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0181] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by Formula 4:

[0182]

[0183] in,

[0184] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;

[0185] T is selected from C and CR each time it appears, either identically or differently. t Or N;

[0186] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0187] R t R gEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0188] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0189] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.

[0190] In this paper, "adjacent substituent R" t R g "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two substituents R t Between, two substituents R g Between, substituent R t and R g Between these adjacent substituent groups, one or more can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.

[0191] According to one embodiment of the present invention, in formulas 3 and 4, T is selected from C and CR each time it appears, either identically or differently. t .

[0192] According to one embodiment of the present invention, in Formula 3, T is selected from C, CR each time it appears, either the same or different. t Or N, and at least one of them is selected from N, for example, one T or two T are selected from N.

[0193] According to one embodiment of the present invention, in Equation 4, T is selected from C, CR each time it appears, either the same or different. t Or N, and at least one of them is selected from N, for example, one T or two T are selected from N.

[0194] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by one of formulas 3-a to 3-j:

[0195]

[0196] in,

[0197] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0198] T is selected from CR each time it appears, either the same or different. t Or N;

[0199] R t Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0200] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0201] Adjacent substituent R t They can be arbitrarily connected to form a ring.

[0202] According to one embodiment of the present invention, in formulas 3-a to 3-j, T is selected from CR each time it appears, either identically or differently. t .

[0203] According to one embodiment of the present invention, in formulas 3-a to 3-j, T is selected from CR each time it appears, either identically or differently. t Or N, and at least one of them is selected from N, for example, one T or two T are selected from N.

[0204] According to one embodiment of the present invention, the second host compound in the organic electroluminescent device has a structure represented by one of formulas 4-a to 4-f:

[0205]

[0206] in,

[0207] G is selected from C(R) each time it appears, either identically or differently. g 2. NR g , O or S;

[0208] T is selected from CR each time it appears, either the same or different. t Or N;

[0209] L T Each occurrence is the same or different of a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof.

[0210] R t R gEach time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms;

[0211] Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0212] Adjacent substituent R t R g They can be arbitrarily connected to form a ring.

[0213] According to one embodiment of the present invention, in formulas 4-a to 4-f, T is selected from CR each time it appears, either identically or differently. t .

[0214] According to one embodiment of the present invention, in formulas 4-a to 4-f, T is selected from CR each time it appears, either identically or differently. t Or N, and at least one of them is selected from N, for example, one T or two T are selected from N.

[0215] According to one embodiment of the present invention, the second host compound is selected from the group consisting of, but not limited to, the following compounds:

[0216]

[0217]

[0218]

[0219] According to one embodiment of the present invention, the organic electroluminescent device emits green light.

[0220] According to one embodiment of the present invention, the organic electroluminescent device emits white light.

[0221] According to one embodiment of the present invention, the first metal complex is doped in the compound and the second compound, and the first metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0222] According to one embodiment of the present invention, the first metal complex is doped in the compound and the second compound, and the first metal complex accounts for 3% to 13% of the total weight of the light-emitting layer.

[0223] According to one embodiment of the present invention, a compound composition comprising the compounds described in any of the foregoing embodiments is disclosed.

[0224] According to one embodiment of the present invention, an electronic device is disclosed, which includes the organic electroluminescent device described in any of the foregoing embodiments.

[0225] Combination with other materials

[0226] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0227] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of hosts, a variety of light-emitting dopants, transport layers, barrier layers, implantation layers, electrodes, and other possible layers. These combinations of materials are 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 herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0228] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0229] Material synthesis examples:

[0230] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0231] Synthesis Example 1: Synthesis of compound A-6

[0232] Step 1: Synthesis of Intermediate B

[0233]

[0234] In a three-necked round-bottom flask, A (15.0 g, 54.9 mmol), pinacol diborate (20.9 g, 82.5 mmol), Pd(dppf)Cl2 (0.81 g, 1.1 mmol), KOAc (10.8 g, 110 mmol), and 200 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a white solid intermediate B (15.0 g, 46.8 mmol), in 85.2% yield.

[0235] Step 2: Synthesis of intermediate D

[0236]

[0237] In a three-necked round-bottom flask, B (8.97 g, 28.0 mmol), C (12.7 g, 42.0 mmol), Pd(PPh3)4 (1.62 g, 1.4 mmol), Na2CO3 (5.9 g, 56.0 mmol), 160 mL THF, and 40 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, the aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate D (5.0 g, 10.87 mmol), in 38.8% yield.

[0238] Step 3: Synthesis of compound A-6

[0239]

[0240] In a three-necked round-bottom flask, D (5.0 g, 10.87 mmol), E (4.23 g, 11.41 mmol), Pd(PPh3)4 (0.25 g, 0.22 mmol), K2CO3 (3.0 g, 21.74 mmol), 60 mL toluene, 15 mL EtOH, and 15 mL H2O were added sequentially. The mixture was heated to reflux overnight under nitrogen protection. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The crude product was subjected to silica gel column chromatography (PE / DCM = 10:1 to 2:1) to give a white solid (6.0 g, 8.98 mmol), with a yield of 82.6%. The product was identified as the target product A-6, with a molecular weight of 667.3.

[0241] Synthesis Example 2: Synthesis of compound A-7

[0242] Step 1: Synthesis of intermediate G

[0243]

[0244] In a three-necked round-bottom flask, F (5.0 g, 18.38 mmol), pinacol diborate (7.0 g, 27.57 mmol), Pd(dppf)Cl2 (0.27 g, 0.37 mmol), KOAc (5.4 g, 55.14 mmol), and 100 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate G (2.8 g, 8.74 mmol), in 47.6% yield.

[0245] Step 2: Synthesis of intermediate H

[0246]

[0247] In a three-necked round-bottom flask, G (4.5 g, 14.0 mmol), C (4.23 g, 14.0 mmol), Pd(PPh3)4 (0.33 g, 0.28 mmol), KHCO3 (2.8 g, 28.1 mmol), 80 mL THF, and 20 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 4:1) to give a white solid intermediate H (2.6 g, 5.66 mmol), in 40.4% yield.

[0248] Step 3: Synthesis of compound A-7

[0249]

[0250] In a three-necked round-bottom flask, H (2.6 g, 5.66 mmol), E (2.1 g, 5.66 mmol), Pd(PPh3)4 (0.13 g, 0.11 mmol), K2CO3 (1.56 g, 11.3 mmol), 80 mL toluene, 10 mL EtOH, and 10 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. Recrystallization from toluene / acetonitrile yielded a white solid (3.4 g, 5.1 mmol), with a yield of 90.1%. The product was identified as the target product A-7, with a molecular weight of 667.3.

[0251] Synthesis Example 3: Synthesis of compound A-8

[0252] Step 1: Synthesis of intermediate J

[0253]

[0254] In a three-necked round-bottom flask, I (27.3 g, 100.0 mmol), pinacol diborate (50.8 g, 200.0 mmol), Pd(dppf)Cl2 (1.5 g, 2.0 mmol), KOAc (19.6 g, 200.0 mmol), and 200 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate J (28.0 g, 87.4 mmol), with a yield of 87.4%.

[0255] Step 2: Synthesis of intermediate K

[0256]

[0257] In a three-necked round-bottom flask, J (9.0 g, 28.1 mmol), C (8.5 g, 28.1 mmol), Pd(PPh3)4 (0.97 g, 0.84 mmol), KHCO3 (5.6 g, 56.2 mmol), 160 mL THF, and 40 mL H2O were added sequentially. The mixture was heated to reflux overnight under N2 protection. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 4:1) to give a white solid intermediate K (5.2 g, 11.3 mmol), in 40.2% yield.

[0258] Step 3: Synthesis of compound A-8

[0259]

[0260] In a three-necked round-bottom flask, K (2.6 g, 5.66 mmol), E (2.1 g, 5.66 mmol), Pd(PPh3)4 (0.13 g, 0.11 mmol), K2CO3 (1.56 g, 11.3 mmol), 80 mL toluene, 10 mL EtOH, and 10 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (2.9 g, 4.2 mmol), with a yield of 74.2%. The product was identified as the target product A-8, with a molecular weight of 667.3.

[0261] Synthesis Example 4: Synthesis of compound A-12

[0262] Step 1: Synthesis of intermediate M

[0263]

[0264] In a three-necked round-bottom flask, J (10.0 g, 31.3 mmol), L (11.9 g, 39.4 mmol), Pd(PPh3)4 (1.8 g, 1.6 mmol), Na2CO3 (6.6 g, 62.6 mmol), 160 mL THF, and 40 mL H2O were added sequentially. The mixture was heated to reflux under N2 protection. After 10 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 4:1) to give a white solid intermediate M (6.7 g, 14.6 mmol), with a yield of 46.5%.

[0265] Step 2: Synthesis of compound A-12

[0266]

[0267] In a three-necked round-bottom flask, M (4.8 g, 10.4 mmol), E (4.1 g, 11.0 mmol), Pd(PPh3)4 (0.60 g, 0.52 mmol), K2CO3 (4.3 g, 31.3 mmol), 120 mL toluene, 30 mL EtOH, and 30 mL H2O were added sequentially. The mixture was heated under reflux overnight under nitrogen protection. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and the solvent was removed by rotary evaporation under reduced pressure. The solid was recrystallized from toluene / ethanol to give a white solid (5.3 g, 7.9 mmol), with a yield of 76.3%. The product was identified as the target product A-12, with a molecular weight of 667.3.

[0268] Synthesis Example 5: Synthesis of compound A-138

[0269] Step 1: Synthesis of intermediate O

[0270]

[0271] In a three-necked round-bottom flask, N (9.9 g, 25.0 mmol), pinacol diborate (9.5 g, 37.5 mmol), Pd(dppf)Cl2 (0.55 g, 0.75 mmol), KOAc (4.9 g, 50.0 mmol), and 80 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N2 protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 4:1) to give a white solid intermediate O (8.1 g, 18.2 mmol), in 72.9% yield.

[0272] Step 2: Synthesis of intermediate P

[0273]

[0274] In a three-necked round-bottom flask, O (8.0 g, 18.1 mmol), C (8.7 g, 29.0 mmol), Pd(PPh3)4 (1.0 g, 0.87 mmol), Na2CO3 (3.8 g, 36.2 mmol), 96 mL THF, and 24 mL H2O were added sequentially. The mixture was heated to reflux overnight under nitrogen protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, the aqueous phase was extracted with DCM, and the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 3:1) to give a white solid intermediate P (4.0 g, 6.8 mmol), in 37.8% yield.

[0275] Step 3: Synthesis of compound A-138

[0276]

[0277] In a three-necked round-bottom flask, P (3.7 g, 7.4 mmol), E (2.4 g, 7.4 mmol), Pd(PPh3)4 (0.37 g, 0.32 mmol), K2CO3 (2.2 g, 16.0 mmol), 60 mL toluene, 15 mL EtOH, and 15 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and ethanol. The solid was then recrystallized from toluene / ethanol to give a white solid (4.3 g, 5.4 mmol), with a yield of 73.0%. The product was identified as the target product A-138, with a molecular weight of 791.3.

[0278] Synthesis Example 6: Synthesis of compound A-230

[0279] Step 1: Synthesis of intermediate R

[0280]

[0281] In a three-necked round-bottom flask, I (10.0 g, 36.61 mmol), Q (6.3 g, 40.27 mmol), Pd(PPh3)4 (0.85 g, 0.73 mmol), K2CO3 (10.1 g, 73.22 mmol), 100 mL toluene, 25 mL EtOH, and 25 mL H2O were added sequentially. The mixture was heated to reflux overnight under nitrogen protection. Heating was stopped, and the mixture was cooled to room temperature. The layers were separated, and the aqueous phase was extracted multiple times with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE) to give a white solid intermediate R (10.8 g, 35.43 mmol), with a yield of 96.8%.

[0282] Step 2: Synthesis of intermediate S

[0283]

[0284] In a three-necked round-bottom flask, R (10.8 g, 35.43 mmol), pinacol diborate (14.0 g, 55.11 mmol), Pd(OAc)₂ (0.17 g, 0.73 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 0.70 g, 1.47 mmol), KOAc (7.21 g, 73.48 mmol), and 100 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, the filtrate was concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (PE / DCM = 5:1 to 2:1) to give a white solid intermediate S (13.1 g, 33.05 mmol), in 90.0% yield.

[0285] Step 3: Synthesis of intermediate U

[0286]

[0287] In a three-necked round-bottom flask, S (9.2 g, 23.2 mmol), T (7.87 g, 34.8 mmol), Pd(PPh3)4 (1.07 g, 0.93 mmol), KHCO3 (5.81 g, 58.0 mmol), 160 mL THF, and 40 mL H2O were added sequentially. The mixture was heated to reflux under N2 protection. After 4 h, TLC was used to confirm the end of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 6:1 to 4:1) to give a white solid intermediate U (6.3 g, 13.7 mmol), with a yield of 59.0%.

[0288] Step 4: Synthesis of compound A-230

[0289]

[0290] In a three-necked round-bottom flask, U (4.6 g, 10.0 mmol), E (3.7 g, 10.0 mmol), Pd(PPh3)4 (0.35 g, 0.30 mmol), K2CO3 (2.76 g, 20.0 mmol), 40 mL toluene, 10 mL EtOH, and 10 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (4.7 g, 7.04 mmol), with a yield of 70.4%. The product was identified as the target product A-230, with a molecular weight of 667.3.

[0291] Synthesis Example 7: Synthesis of compound A-410

[0292] Step 1: Synthesis of intermediate W

[0293]

[0294] In a three-necked round-bottom flask, V (6.0 g, 17.1 mmol), 3-biphenylboronic acid (3.70 g, 18.81 mmol), Pd(PPh3)4 (0.59 g, 0.51 mmol), K2CO3 (4.72 g, 34.2 mmol), 56 mL toluene, 14 mL EtOH, and 14 mL H2O were added sequentially. The mixture was heated to reflux overnight under N2 protection. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The organic phase was collected, and the aqueous phase was extracted multiple times with DCM. 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 = 50:1) to give a colorless oily intermediate W (5.6 g, 15.8 mmol), with a yield of 92.3%.

[0295] Step 2: Synthesis of intermediate X

[0296]

[0297] In a three-necked round-bottom flask, W (6.0 g, 17.47 mmol), pinacol diboronate (6.65 g, 26.2 mmol), Pd(OAc)₂ (0.08 g, 0.35 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (X-Phos, 0.33 g, 0.67 mmol), KOAc (3.43 g, 34.94 mmol), and 87 mL of 1,4-dioxane were added sequentially. The mixture was heated to reflux overnight under N₂ protection. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction mixture 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 to 2:1) to give a white solid intermediate X (4.71 g, 10.55 mmol), with a yield of 60.4%.

[0298] Step 3: Synthesis of intermediate Y

[0299]

[0300] In a three-necked round-bottom flask, J (10.0 g, 31.2 mmol), T (8.5 g, 37.5 mmol), Pd(PPh3)4 (1.1 g, 0.98 mmol), Na2CO3 (6.6 g, 62.4 mmol), 240 mL THF, and 60 mL H2O were added sequentially. The mixture was heated to reflux overnight under nitrogen protection. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature. The liquid phase was separated, and the aqueous phase was extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 8:1 to 4:1) to give a pale yellow solid intermediate Y (6.9 g, 18.0 mmol), in 57.7% yield.

[0301] Step 4: Synthesis of compound A-410

[0302]

[0303] In a three-necked round-bottom flask, X (4.5 g, 10.0 mmol), Y (3.8 g, 10.0 mmol), Pd(PPh3)4 (0.35 g, 0.30 mmol), K2CO3 (2.76 g, 20.0 mmol), 40 mL toluene, 10 mL EtOH, and 10 mL H2O were added sequentially. The mixture was heated under N2 protection and refluxed overnight. TLC was used to confirm the completion of the reaction. Heating was stopped, and the mixture was cooled to room temperature and filtered under reduced pressure. The resulting solid was washed successively with water and methanol. The solid was then recrystallized from toluene / acetonitrile to give a white solid (5.9 g, 8.8 mmol), with a yield of 88.0%. The product was identified as the target product A-410, with a molecular weight of 667.3.

[0304] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0305] Device Examples

[0306] Device Example 1

[0307] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 Under the condition of Turbo evaporation, ITO anodes were sequentially deposited by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound PH-23 was used as the electron blocking layer (EBL). Then, compound GD23 was doped into compound PH-23 and compound A-8 of the present invention and co-deposited as the light-emitting layer (EML). Compound H2 was used as the hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as the electron transport layer (ETL). Finally, a 1 nm thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer, and a 120 nm thick layer of aluminum was deposited as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0308] Device Example 2

[0309] The preparation of device example 2 is the same as that of device example 1, except that compound A-12 is used instead of compound A-8 in the light-emitting layer (EML).

[0310] Device Example 3

[0311] The fabrication of device example 3 was the same as that of device example 1, except that compound A-230 was used instead of compound A-8 in the light-emitting layer (EML).

[0312] Device Example 4

[0313] The fabrication of device example 4 was the same as that of device example 1, except that compound A-410 was used instead of compound A-8 in the light-emitting layer (EML).

[0314] Device Example 5

[0315] The fabrication of device example 5 was the same as that of device example 1, except that compound A-7 was used instead of compound A-8 in the light-emitting layer (EML).

[0316] Device Example 6

[0317] The fabrication of device example 6 was the same as that of device example 1, except that compound A-6 was used instead of compound A-8 in the light-emitting layer (EML).

[0318] Device Comparison Example 1

[0319] The fabrication of Comparative Example 1 was the same as that of Example 1, except that compound C-1 was used instead of compound A-8 in the light-emitting layer (EML).

[0320] Device Comparison Example 2

[0321] The fabrication of Comparative Example 2 was the same as that of Example 1, except that compound C-2 was used instead of compound A-8 in the light-emitting layer (EML).

[0322] Device Comparison Example 3

[0323] The fabrication of Comparative Example 3 was the same as that of Example 1, except that compound C-3 was used instead of compound A-8 in the light-emitting layer (EML).

[0324] Device Comparison Example 4

[0325] The fabrication of Comparative Example 4 was the same as that of Example 1, except that compound C-4 was used instead of compound A-8 in the light-emitting layer (EML).

[0326] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0327] Table 1. Device structures of Examples 1 to 6 and Comparative Examples 1 to 4

[0328]

[0329] The material structure used in the device is shown below:

[0330]

[0331]

[0332] Table 2 shows the results at 15 mA / cm 2 CIE data, external quantum efficiency (EQE), and current efficiency (CE) measured under constant current; and at 80 mA / cm². 2 Device lifetime (LT97) measured under constant current.

[0333] Table 2 Device data for Examples 1 to 6 and Comparative Examples 1 to 4

[0334]

[0335]

[0336] discuss:

[0337] In Examples 1, 3, and Comparative Example 1, the phosphorescent dopant GD23 was doped into compounds A-8 and A-230 of the present invention, respectively, and into compound C-1 of the non-present invention. The main difference between compounds A-8, A-230, and C-1 is that fluorene and triazine are linked by different groups. In compound A-8, fluorene and triazine are directly bonded; in compound A-230, fluorene and triazine are linked by a phenylene group; and in compound C-1, fluorene is linked to triazine by a pyridylene group. Compared with Comparative Example 1, the EQE and CE of Examples 1 and 3 were improved, especially the device lifetime, which was significantly improved by 103.7 times and 51.2 times, respectively. Meanwhile, the devices in Examples 2 and 4 used compounds A-12 and A-410 of the present invention. Compared with Comparative Example 1, their EQE and CE were improved, and their device lifetime was significantly improved by 83.2 times and 97.7 times, respectively. The compounds of Formula 1 of the present invention have a direct bond and an arylene group between the fluorene group and the triazine group. Compared with compounds containing a heteroarylene group as a bridging group between the fluorene and the triazine group, they have higher efficiency and longer device life when applied to organic electroluminescent devices.

[0338] In Example 5 and Comparative Example 2, the phosphorescent dopant GD23 was doped into compound A-7 of the present invention and compound C-2 of a non-present invention, respectively. The difference between compound A-7 and compound C-2 is only that an aryl substituent is present at the 1-position of the dibenzofuran group. Compared with Comparative Example 2, the EQE and CE of Example 5 are comparable, but its device lifetime is improved by 57.2%. This demonstrates that the compounds of the present invention having specific substituents at specific positions on the dibenzo five-membered ring exhibit longer device lifetimes when applied to organic electroluminescent devices compared to compounds without substituents on the dibenzo five-membered ring.

[0339] In Example 5 and Comparative Example 3, the phosphorescent dopant GD23 was doped into compound A-7 of the present invention and compound C-3 of a non-present invention, respectively. The only difference between compound A-7 and compound C-3 is that the dimethylfluorenyl group is replaced with a dibenzofuranyl group. The EQE and CE of Example 5 are the same as those of Comparative Example 3, but its device lifetime is significantly improved by 8.7 times. This demonstrates that the compounds of the present invention having the structure of Formula 1 have a dibenzo five-membered ring-triazine-fluorenyl backbone, which, compared to compounds containing a dibenzofuran-triazine-dibenzofuran backbone structure, exhibits a longer device lifetime when applied to organic electroluminescent devices.

[0340] In Example 6 and Comparative Example 4, the phosphorescent dopant GD23 was doped into compound A-6 of the present invention and compound C-4 of the non-present invention, respectively. The main difference between compound A-6 and compound C-4 is that compound C-4 forms an oxygen-containing heterocycle at the 1-position of the dibenzofuran group. The EQE and CE of Example 6 are the same as those of Comparative Example 4, but its device lifetime is significantly improved by 1.5 times. This demonstrates that compounds of the present invention having a specific substituent at a specific position of the dibenzo five-membered ring exhibit a longer device lifetime when applied to organic electroluminescent devices compared to compounds with an oxygen-containing heterocycle substituent at the 1-position of the dibenzo five-membered ring.

[0341] In summary, the compounds of this invention, when applied to organic electroluminescent devices, can improve the electron-hole transport balance of the material. Compared to using compounds not of this invention, the device efficiency (EQE and CE) is comparable to or even improved, while the device lifetime is unexpectedly significantly increased, thus greatly improving the overall performance of the device. This is of great help to the industry.

[0342] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A compound having the structure shown in Formula 1: X is selected from O; X1-X6are the same or different at each occurrence and are selected from the group consisting of CR x ; Y1-Y5are the same or different at each occurrence and are selected from the group consisting of CR y ; Z1-Z8are the same or different at each occurrence and are selected from C or CR z , and one of Z1-Z4is selected from C and is attached to L2; Ar is selected, either identically or differently, from substituted or unsubstituted aryl groups having 6-12 carbon atoms; L1 is selected from a single bond; L2 is selected from single bonds or phenylene in each occurrence, either identically or differently. R y , R x , and R z are the same or different at each occurrence selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms, a cyano group, and combinations thereof; R is selected from the group consisting of the following, either identically or differently each time it appears: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-6 carbon atoms; Substituted alkyl, substituted aryl, refers to any one of the alkyl or aryl groups being replaced by one or at least two groups selected from deuterium, halogen, unsubstituted alkyl having 1-6 carbon atoms, unsubstituted aryl having 6-12 carbon atoms, cyano, and combinations thereof.

2. The compound of claim 1, wherein L2 is selected from phenylene each time it appears, either identically or differently.

3. The compound of claim 1, wherein L2 is selected from single bonds each time it appears, either identically or differently.

4. The compound of claim 1, wherein R x R y R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, cyano groups, and combinations thereof.

5. The compound of claim 1, R x R y R z Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, cyano, and combinations thereof.

6. The compound of claim 1, wherein R, each time it appears, is selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, and combinations thereof.

7. The compound of claim 1, wherein R, each time appearing, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, and combinations thereof.

8. The compound of claim 1, wherein Ar, each time appearing, is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

9. A compound, wherein, The compound is selected from the group consisting of: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Optionally, the hydrogen in the above compounds can be partially or completely replaced by deuterium.

10. An organic electroluminescent device, comprising: An anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer comprises a compound according to any one of claims 1-9.

11. The organic electroluminescent device as claimed in claim 10, wherein, The organic layer containing the compound is a light-emitting layer, and the compound is the host compound.

12. A composition comprising the compound of any one of claims 1-9.

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