Organic electroluminescent material and device thereof

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound having a structure of Formula 1, which can be used in an organic electroluminescent device, for example, as a host material, a transport material, etc. These compounds can improve the electron and hole transport balance ability of the material, make the organic electroluminescent device have a longer device lifetime, and can provide better device performance. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

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 complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). 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] US2016293853A1 discloses an organic compound having the following structure and an organic light-emitting device comprising said compound: Where G can be selected from the following structures: Where n2 is selected from 0 or 1, when n2 is 0, L 3 It does not exist; Z 1 Z 2 and Z 4 To Z 8 Z 17 To Z 32 Each is independently selected from N and CR6; Ar 2 Selected from aryl and heteroaryl groups. This application discloses the following compounds in their specific structures: This application does not disclose or teach hexapentahexafused ring-carbazole compounds with specific substitutions and their effects on device performance.

[0009] CN112961145A discloses an organic compound having the following structure and an organic light-emitting device comprising the compound: Where X is O or S; Z1-Z6 may be the same or different, and each is independently CH or CR1; R1 is the group shown in Formula 2: Furthermore, at least one of Z1-Z6 contains a group represented by Formula 2; R3 is a C6-C30 aryl or a C5-C30 heteroaryl; R2 and R4 may be the same or different, each independently being hydrogen, a C6-C30 aryl, or a C5-C30 heteroaryl; L is a single bond or a phenylene bond; Y1-Y4 are independently CH or CD. This application discloses the following compounds in their specific structures: This application discloses compounds with bicarbazole structures linked to specific fused ring structures, and their applications in organic electroluminescent devices. This application does not disclose or teach hexa-penta-hexa-fused ring bicarbazole compounds with specific substitutions and their effects on device performance.

[0010] WO2018230860A1 discloses an organic compound having the following structure and an organic light-emitting device comprising said compound: Where R is C, either substituted or unsubstituted. 6-60 Aryl;Cy has the following fused ring structure: A is a structure fused with two adjacent rings as follows: B has the following ring structure: The following compounds are disclosed in this application: The application does not disclose or teach hexapentahexafused ring-carbazole compounds with specific substitutions and their effects on device performance.

[0011] WO2015178732A1 discloses an organic electroluminescent device, wherein the light-emitting layer comprises a first host compound having the following structure: Where X is O or S; Ar1 ​​represents a substituted or unsubstituted (C6-C30) aryl group; L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group. The application discloses the following compounds in their specific structures: This application does not disclose or teach hexapentahexafused ring-carbazole compounds with specific substitutions and their effects on device performance.

[0012] WO2018174679A1 discloses an organic electroluminescent device, wherein at least one organic layer comprises an organic compound having the following structure: Wherein N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing at least one N; L is a straight bond, a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene; a is an integer selected from 1 to 3. The application discloses the following compounds in specific structures: The application does not disclose or teach the use of hexapentapenta-hexafused cyclic carbazole compounds with specific substitutions and their effects on device performance.

[0013] Currently reported bicarbazole-based organic semiconductor materials exhibit limitations in carrier transport capability and lifetime in optoelectronic devices. Therefore, the application potential of these materials warrants further in-depth research and development. Summary of the Invention

[0014] This invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the aforementioned problems. These compounds can be used in organic electroluminescent devices, for example, as host materials, transport materials, etc. These novel compounds improve the electron-hole transport balance of materials, providing better device performance.

[0015] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0016]

[0017] in,

[0018] X is selected from O, S, or Se;

[0019] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0020] U1-U8 are selected from C and CR each time they appear, either identically or differently. u Or N; where one of U5-U8 is selected from C and connected to L1;

[0021] V1-V8 are selected from C and CR each time they appear, either identically or differently. v Or N; where one of V1-V4 is selected from C and connected to L1;

[0022] R y Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0023] L1 and L2, each time they appear, are selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0024] 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;

[0025] R x R y R u and R v 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;

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

[0027] Adjacent substituent R y They can be arbitrarily connected to form a loop;

[0028] Adjacent substituent R u and R v They can be arbitrarily connected to form a ring.

[0029] 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.

[0030] According to another embodiment of the present invention, a compound composition comprising the compounds described in the foregoing embodiments is also disclosed.

[0031] This invention discloses a novel compound having the structure of Formula 1, wherein the compound has a hexa-penta-hexafused ring-bicarbazole skeleton and a substituted phenyl group at a specific position of the hexa-penta-hexafused ring group. When applied to organic electroluminescent devices, this compound can improve the electron-hole transport balance, providing better device performance, such as increased device efficiency and lifetime. Attached Figure Description

[0032] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0033] 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

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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).

[0045] 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.

[0046] 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).

[0047] Definition of the term "substituent group"

[0048] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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, fenene, fluorene, pyrene, etc. 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'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in 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.

[0065] 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", and "substituted carboxylic acid" are used interchangeably. The substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl groups. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms. Cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, and unsubstituted alkyne groups having 6-30 carbon atoms. Aryl, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof with 0-20 carbon atoms.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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:

[0071]

[0072] 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:

[0073]

[0074] 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:

[0075]

[0076] 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:

[0077]

[0078] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0079]

[0080] in,

[0081] X is selected from O, S, or Se;

[0082] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0083] U1-U8 are selected from C and CR each time they appear, either identically or differently. u Or N; where one of U5-U8 is selected from C and connected to L1;

[0084] V1-V8 are selected from C and CR each time they appear, either identically or differently. v Or N; where one of V1-V4 is selected from C and connected to L1;

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

[0086] L1 and L2, each time they appear, are selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0087] 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;

[0088] R x R y R u and R vEach 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;

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

[0090] Adjacent substituent R y They can be arbitrarily connected to form a loop;

[0091] Adjacent substituent R u and R v They can be arbitrarily connected to form a ring.

[0092] In this paper, "adjacent substituent R" x "Can be optionally linked to form a ring" is intended to represent any two adjacent substituents R. x They can be connected to form a loop. It is obvious that any adjacent R... x They can also be left unconnected to form a loop.

[0093] In this paper, "adjacent substituent R" y "Can be optionally linked to form a ring" is intended to represent any two adjacent substituents R. y They can be connected to form a loop. It is obvious that any adjacent R... y They can also be left unconnected to form a loop.

[0094] In this paper, "adjacent substituent R" u R v "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, two adjacent substituents R uBetween two adjacent substituents R v Between, and adjacent substituents R u and R v Between these substituent groups, any one or more of them can be connected to form a ring. Obviously, it will be apparent to those skilled in the art that these adjacent substituent groups may also not be connected to form a ring.

[0095] According to one embodiment of the present invention, X is selected from O or S.

[0096] According to one embodiment of the present invention, X is O.

[0097] According to one embodiment of the present invention, X1-X6 are selected from CR each time they appear, either identically or differently. x .

[0098] According to one embodiment of the present invention, U1-U8 are selected from C or CR each time they appear, either identically or differently. u And one of U5-U8 is selected from C and connected to L1.

[0099] According to one embodiment of the present invention, V1-V8 are selected from C or CR each time they appear, either identically or differently. v And one of V1-V4 is selected from C and connected to L1.

[0100] According to one embodiment of the present invention, the first compound has a structure represented by formula 1-a:

[0101]

[0102] in,

[0103] X is selected from O, S, or Se;

[0104] X1-X6 are selected from CR each time they appear, either the same or different. x Or N;

[0105] U1-U5, U7, and U8 are selected from CR each time they appear, either identically or differently. u Or N;

[0106] V1, V2, and V4-V8 are selected from CR each time they appear, either identically or differently. v Or N;

[0107] R y Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted.

[0108] L1 and L2, each time they appear, are selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0109] 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;

[0110] R x R y R u and R v 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;

[0111] Adjacent substituent R x They can be arbitrarily connected to form a loop;

[0112] Adjacent substituent R y They can be arbitrarily connected to form a loop;

[0113] Adjacent substituent R u and R v They can be arbitrarily connected to form a ring.

[0114] According to one embodiment of the present invention, U1-U8 are selected from C, CR each time they appear, either identically or differently. uOr N, and at least one of U1-U8 is selected from N, for example, one or two of U1-U8 are selected from N.

[0115] According to one embodiment of the present invention, V1-V8 are selected from C, CR each time they appear, either identically or differently. v Or N, and at least one of V1-V8 is selected from N, for example, one or two of V1-V8 are selected from N.

[0116] According to one embodiment of the present invention, X1-X6 are selected from CR each time they appear, either identically or differently. x Or N, and at least one of X1-X6 is selected from N, for example, one or two of X1-X6 are selected from N.

[0117] 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.

[0118] According to one embodiment of the invention, Ar, each time it appears, is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, or combinations thereof.

[0119] According to one embodiment of the invention, Ar is selected from substituted or unsubstituted biphenyls each time it appears.

[0120] According to one embodiment of the invention, Ar is selected from substituted or unsubstituted meta-biphenyls each time it appears.

[0121] According to one embodiment of the invention, L1 and L2, each time they appear, are selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0122] According to one embodiment of the invention, L1 and L2, each time they appear, are selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or combinations thereof.

[0123] According to one embodiment of the present invention, L1 and L2 are selected from single bonds, phenylene, biphenylene or naphthylene each time they appear.

[0124] According to one embodiment of the present invention, R u R v R x and R y 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 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0125] According to one embodiment of the present invention, R u R v R x and R y Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, fluorine, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, and combinations thereof.

[0126] According to one embodiment of the present invention, R u R v R x and R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, and combinations thereof.

[0127] According to one embodiment of the present invention, X1-X3 are selected from CR each time they appear, either identically or differently. x .

[0128] According to one embodiment of the present invention, R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. The group includes substituted or unsubstituted alkynyl groups having 2-20 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, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0129] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of: 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, or combinations thereof.

[0130] According to one embodiment of the present invention, R x Each time it appears, it is selected from hydrogen or deuterium, either the same or different.

[0131] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds A-1 to A-399, and the specific structures of compounds A-1 to A-399 are given in claim 10.

[0132] According to one embodiment of the present invention, the hydrogen in the A-1 to A-399 structures is partially or completely replaced by deuterium.

[0133] 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 above embodiments.

[0134] According to one embodiment of the present invention, the organic layer containing the compound is a light-emitting layer, and the compound is a first host compound, the light-emitting layer further comprising at least a first metal complex.

[0135] 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;

[0136] Metal M is selected from metals with a relative atomic mass greater than 40;

[0137] L a L b and L c The first, second, and third ligands, respectively, coordinate with the metal M. a L b L c They can be the same or different;

[0138] L a L b and L c They can be selectively linked to form multidentate ligands;

[0139] m is 1, 2, or 3; n is 0, 1, or 2; q is 0, 1, or 2; the sum of m, n, and q 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;

[0140] ligand L a It has the structure shown in Equation 2:

[0141]

[0142] When ring C1 and ring C2 appear, they are selected, either identically or differently, from substituted or unsubstituted aromatic rings having 5-30 ring atoms, substituted or unsubstituted heteroaromatic rings having 5-30 ring atoms, or combinations thereof;

[0143] Q1 and Q2 are selected from C or N each time they appear, either the same or different.

[0144] R1 and R2 appearing the same or different each time indicate monosubstitution, polysubstitution, or no substitution;

[0145] R1 and R2, each time appearing, are 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... 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;

[0146] Adjacent substituents R1 and R2 can optionally be linked to form a ring;

[0147] ligand L b and L c Each occurrence may be the same or different, selected from monoanionic bidentate ligands.

[0148] In this embodiment, "adjacent substituents R1, R2 can optionally connect to form a ring" is intended to indicate that any one or more of adjacent substituent groups, such as adjacent substituents R1, adjacent substituents R2, and adjacent substituents R1 and R2, can connect to form a ring. Obviously, these substituents may also not connect to form a ring.

[0149] According to one embodiment of the present invention, the ligand L b and L c Each occurrence is either identical or different and selected from the group consisting of the following structures:

[0150]

[0151]

[0152] in,

[0153] R a and R b Each occurrence, whether identical or different, indicates single substitution, multiple substitution, or no substitution;

[0154] 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 ;

[0155] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0156] 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;

[0157] 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.

[0158] In this embodiment, "adjacent substituent R" a R b R c RN1 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 adjacent substituents R a Between two adjacent substituents R b Between, adjacent substituents R a and R b Between, adjacent substituents R a and R c Between, adjacent substituents R b and R c Between, adjacent substituents R a and R N1 Between, adjacent substituents R b and R N1 Between, adjacent substituents R a and R C1 Between, adjacent substituents R a and R C2 Between, adjacent substituents R b and R C1 Between, adjacent substituents R b and R C2 Between, adjacent substituents R a and R N2 Between, and adjacent substituents 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.

[0159] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt each time it appears.

[0160] According to one embodiment of the present invention, the metal M is selected from Pt or Ir each time it appears.

[0161] 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 the structure represented by Equation 3:

[0162]

[0163] in,

[0164] m can be 0, 1, 2, or 3; when m is 2 or 3, multiple La Same or different; multiple L when m is 0 or 1 b Same or different;

[0165] T1-T6 each time appear in the same or different selections from CR t Or N;

[0166] R a R b and R d Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0167] R a R b R d and R t 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, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0168] Adjacent substituent R a R b They can be arbitrarily connected to form a loop;

[0169] Adjacent substituent R d R t They can be arbitrarily connected to form a ring.

[0170] 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 adjacent substituents R a Between two adjacent substituents R bBetween, and adjacent substituents 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.

[0171] 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 adjacent substituents R t Between two adjacent 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.

[0172] 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.

[0173] 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 either fluorine or cyanide.

[0174] 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 It is either fluorine or cyano, and the other 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.

[0175] 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.

[0176] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of:

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] According to one embodiment of the present invention, the light-emitting layer further comprises a second host compound having a structure represented by Formula 4:

[0184]

[0185] in,

[0186] E1-E6 are selected from C or CR each time they appear, either identically or differently. e Or N, and at least two of E1-E6 are N, at least one of E1-E6 is C, and connected to E5;

[0187]

[0188] in,

[0189] Each time Z appears, the same or different choices are made from the group consisting of O, S, Se, N, NR', CR'R', SiR'R', GeR'R' and R'C=CR'; when two R's exist simultaneously, the two R's can be the same or different.

[0190] p is 0 or 1, r is 0 or 1;

[0191] When Z is selected from N, p is 0 and r is 1;

[0192] When Z is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R', GeR'R' and R'C=CR', p is 1 and r is 0.

[0193] L, each time it appears, is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-20 carbon atoms, or combinations thereof.

[0194] Z1-Z8 are selected from C and CR each time they appear, either identically or differently. z Or N;

[0195] R e , R' and R zEach 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;

[0196] Adjacent substituent R e ,R',R z They can be arbitrarily connected to form a loop;

[0197] "*" represents the connection position between Equation 4 and Equation 5.

[0198] In this embodiment, "adjacent substituent R" e ,R',R z "Can be optionally linked to form a ring" is intended to indicate that adjacent substituent groups therein, for example, adjacent substituent R e Between, between adjacent substituents R', between adjacent substituents R z Between, and adjacent substituents R' and 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.

[0199] According to one embodiment of the present invention, E1-E6 are selected from C and CR each time they appear, either identically or differently. e Or N, and three of E1-E6 are N, and at least one of E1-E6 is CR. e And the R e Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0200] "And / or Z is selected from O, S, N or NR each time it appears, either the same or different";

[0201] And / or at least one or at least two of Z1-Z8 are selected from CR z And the R z Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 5-30 carbon atoms, or combinations thereof;

[0202] And / or L, each time appearing, is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0203] According to one embodiment of the present invention, Z1-Z8 are selected from C, CR each time they appear, either identically or differently. z Or N, and at least one of Z1-Z8 is selected from N, for example, one or two of Z1-Z8 are selected from N.

[0204] According to one embodiment of the present invention, the second host compound is selected from the group consisting of:

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] According to one embodiment of the present invention, the hydrogen in the H-1 to H-99 structures is partially or completely replaced by deuterium.

[0215] According to one embodiment of the present invention, the first metal complex is doped in the first host compound and the second host compound, and the weight of the first metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.

[0216] According to one embodiment of the present invention, the first metal complex is doped in the first host compound and the second host compound, and the weight of the first metal complex accounts for 3%-13% of the total weight of the light-emitting layer.

[0217] According to one embodiment of the present invention, a compound composition comprising the compounds described in any of the above embodiments is disclosed.

[0218] Combination with other materials

[0219] 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.

[0220] 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 light-emitting dopants, substrates, transport layers, blocking 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.

[0221] 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.

[0222] Material synthesis examples:

[0223] 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:

[0224] Synthesis Example 1: Synthesis of Compound A-1

[0225] Step 1: Synthesis of Intermediate B

[0226]

[0227] In a 100 mL three-necked round-bottom flask, intermediate A (6.0 g, 16.2 mmol), CuBr2 (11.94 g, 53.5 mmol), 1,4-dioxane (20 mL), DMF (20 mL), and water (10 mL) were added. The mixture was purged three times with N2 and heated under 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 system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 50:1) to give a white solid intermediate B (3.5 g, 10.8 mmol), with a yield of 66.7%.

[0228] Step 2: Synthesis of compound A-1

[0229]

[0230] In a 100 mL three-necked round-bottom flask, add intermediate B (3.9 g, 12.0 mmol), intermediate C (4.1 g, 10.0 mmol), Pd2(dba)3 (0.92 g, 1.0 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (S-phos, 0.41 g, 1.0 mmol). t BuONa (1.9 g, 20.0 mmol) and xylene (50 mL) were purged three times with N2 and heated under 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 system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1) to give a white solid compound A-1 (4.0 g, 6.2 mmol), with a yield of 62.0%. The product was identified as the target product with a molecular weight of 650.2.

[0231] Synthesis Example 2: Synthesis of compound A-6

[0232]

[0233] In a 100 mL three-necked round-bottom flask, add intermediate B (2.3 g, 7.2 mmol), intermediate D (2.8 g, 8.7 mmol), Pd2(dba)3 (0.66 g, 0.7 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (S-phos, 0.30 g, 0.7 mmol). t BuONa (1.4 g, 14.4 mmol) and xylene (40 mL) were purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1) to give a white solid compound A-16 (3.4 g, 4.7 mmol), with a yield of 65.3%. The product was identified as the target product with a molecular weight of 726.3.

[0234] Synthesis Example 3: Synthesis of Compound A-95

[0235] Step 1: Synthesis of intermediate G

[0236]

[0237] In a 250 mL three-necked round-bottom flask, intermediates E (8.0 g, 22.9 mmol), F (5.9 g, 29.7 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), K2CO3 (9.5 g, 68.7 mmol), 1,4-dioxane (100 mL), and H2O (25 mL) were added. The mixture was heated under nitrogen protection and refluxed overnight. Heating was stopped, and the mixture was cooled to room temperature. 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 = 15:1) to give a white solid intermediate G (7.0 g, 19.7 mmol), with a yield of 86.1%.

[0238] Step 2: Synthesis of compound A-95

[0239]

[0240] In a 100 mL three-necked round-bottom flask, add intermediate G (4.3 g, 12.0 mmol), intermediate C (4.1 g, 10.0 mmol), Pd2(dba)3 (0.92 g, 1.0 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (S-phos, 0.41 g, 1.0 mmol). t BuONa (1.9 g, 20.0 mmol) and xylene (50 mL) were purged three times with N2 and heated under N2 protection under reflux overnight. The reaction was confirmed by TLC spotting, heating was stopped, and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (PE / DCM = 5:1) to give a white solid compound A-95 (4.6 g, 6.3 mmol), with a yield of 63.0%. The product was identified as the target product with a molecular weight of 726.3.

[0241] Device Examples

[0242] Example 1

[0243] 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... -8Under 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 H1 was used as the electron blocking layer (EBL). Then, compound GD1 was doped into compound H-1 and compound A-1 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.

[0244] Example 2

[0245] The preparation of Example 2 was the same as that of Example 1, except that compound A-6 was used instead of compound A-1 in the light-emitting layer (EML).

[0246] Comparative Example 1

[0247] Comparative Example 1 was prepared in the same manner as Example 1, except that compound C-1 was used instead of compound A-1 in the light-emitting layer (EML).

[0248] Comparative Example 2

[0249] Comparative Example 2 was prepared in the same manner as Example 1, except that compound C-2 was used instead of compound A-1 in the light-emitting layer (EML).

[0250] Comparative Example 3

[0251] Comparative Example 3 was prepared in the same manner as Example 1, except that compound C-3 was used instead of compound A-1 in the light-emitting layer (EML).

[0252] Comparative Example 4

[0253] Comparative Example 4 was prepared in the same manner as Example 1, except that compound C-4 was used instead of compound A-1 in the light-emitting layer (EML).

[0254] 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.

[0255] Table 1. Partial device structures of Examples 1 to 2 and Comparative Examples 1 to 4

[0256]

[0257] The material structure used in the device is shown below:

[0258]

[0259]

[0260] Table 2 shows the results at 15 mA / cm 2 CIE data, drive voltage, external quantum efficiency (EQE), current efficiency (CE), and power efficiency (PE) measured under constant current; and at 80 mA / cm 2 Device lifetime (LT95) measured under constant current.

[0261] Table 2 Device data for Examples 1 to 2 and Comparative Examples 1 to 4

[0262]

[0263]

[0264] discuss:

[0265] As shown in Table 2, compared with Comparative Example 1, the voltage of Example 1 remained basically the same, but EQE increased by 25.1%, CE increased by 26.6%, PE increased by 27.7%, and the device lifetime increased significantly by 3.40 times. These results indicate that, among compounds with a hexa-penta-hexa-fused-ring bicarbazole skeleton, compared with Comparative Example 1 where the 9-position of the hexa-penta-hexa-fused-ring group is a triazine group, Example 1 of the present invention, with a phenyl substituent at the 9-position of the hexa-penta-hexa-fused-ring group, can significantly improve the device efficiency (EQE, PE, and CE) and lifetime, comprehensively enhancing the overall performance of the device.

[0266] Compared to Comparative Example 2, the device efficiency (EQE, PE, and CE) of Example 1 was improved. More importantly, in terms of device lifetime, Example 1 showed a significant improvement of 337.5 times compared to Comparative Example 2. These results indicate that, in compounds having a hexa-penta-hexa-fused-ring-bicarbazole skeleton, compared to Comparative Example 2, where the hexa-penta-hexa-fused-ring group is further fused with a phenyl group, Example 1 of the present invention, with a phenyl substituent at position 9 of the hexa-penta-hexa-fused-ring group, can significantly improve device lifetime.

[0267] Compared to Comparative Example 3, the voltage of Example 1 was slightly lower, while the device efficiency (EQE, PE, and CE) remained essentially the same, but the device lifetime was increased by 1.88 times. These results indicate that, in compounds having a hexa-penta-hexafused ring-bicarbazole skeleton, Example 1, with an aryl substituent at position 9 of the hexa-penta-hexafused ring group, significantly improves device lifetime compared to Comparative Example 3, which had no substitution of the hexa-penta-hexafused ring group.

[0268] Compared to Comparative Example 4, Example 1 showed a 4.4% reduction in voltage, with EQE and CE remaining essentially the same, a 5.2% increase in PE, and a 12% improvement in device lifetime. These results demonstrate that, in compounds with a hexa-penta-hexa-fused-ring bicarbazole skeleton, Example 1, with a phenyl substituent at the 9-position of the hexa-penta-hexa-fused-ring group, significantly improves device lifetime compared to Comparative Example 4, where the 3-position of the hexa-penta-hexa-fused-ring group is phenyl-substituted.

[0269] As can be seen from the above, the compound A-1 used in Example 1 can provide superior device performance. Based on this, the compound structure was further improved to obtain the compound A-6 used in Example 2, which has different substituents on the bicarbazole group. Example 2 has the same excellent device efficiency (EQE, PE and CE) as Example 1, and in terms of device lifetime, the device lifetime of Example 2 is improved by 35.1% on the basis of the higher device lifetime of Example 1.

[0270] The above results indicate that, compared with existing technologies that have a heteroaryl or fused structure at a specific position of the hexapentahexa-carbazole skeleton, compounds of the present invention with a specific substitution at a specific position of the hexapentahexa-fused ring group can improve device performance, especially significantly improve device lifetime, and ultimately improve the overall performance of the device.

[0271] In summary, the compounds of this invention, when applied to organic electroluminescent devices, can improve the balance between electron and hole transport, enhance the overall performance of the devices, and significantly extend the device lifespan, thus demonstrating broad application prospects.

[0272] 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: in, X is selected from O or S; X1-X6 are selected from CR x ; U1-U8 are selected from C or CR each time they appear, either identically or differently. u ; U6 is selected from C and connected to L1; V1-V8 are selected from C or CR each time they appear, either identically or differently. v V3 is selected from C and connected to L1; R y Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. L1 and L2 are selected from single bonds; Ar is selected, either identically or differently, from substituted or unsubstituted aryl groups having 6-30 carbon atoms; R x R y R u and R v 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 alkyl groups having 1-20 carbon atoms; The compound mentioned is not from the group consisting of the following compounds: ， ； The alkyl or aryl group is unsubstituted or substituted by one or more alkyl groups selected from deuterium, halogens, unsubstituted alkyl groups having 1-20 carbon atoms, or unsubstituted aryl groups having 6-30 carbon atoms.

2. The compound of claim 1, wherein X is O.

3. The compound of claim 1, wherein, Ar is selected, either identically or differently, from substituted or unsubstituted aryl groups having 6-20 carbon atoms.

4. The compound of claim 3, wherein Ar, each time it appears, is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorene.

5. The compound of claim 1, wherein, R u R v R x and R y 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 alkyl groups having 1-20 carbon atoms; Ar, each time it appears, is selected from substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene.

6. The compound of claim 1, R u R v R x and R y Each time it appears, it is selected from the following groups, either the same or different: hydrogen, deuterium, fluorine.

7. The compound of claim 1, wherein, X1-X3 are selected from CR each time they appear, either the same or different. x The R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-12 carbon atoms.

8. The compound of claim 7, wherein R x Each time it appears, it is selected from hydrogen or deuterium, either the same or different.

9. A compound, wherein, The compounds are selected from the group consisting of the following compounds: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Optionally, the hydrogen in the structures A-2 to A-5, A-7 to A-20, A-219 to A-230, A-291 to A-310, A-351 to A-353, A-387 to A-389, and A-391 to A-393 is partially or completely replaced by deuterium.

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

11. The organic electroluminescent device of claim 10, wherein the organic layer comprising the compound is a light-emitting layer, and the compound is a first host compound, and the light-emitting layer further comprises at least a first metal complex.

12. The organic electroluminescent device of claim 11, wherein the light-emitting layer further comprises a second host compound.

13. A compound composition comprising the compound according to any one of claims 1-9.

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