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 as a host material in an electroluminescent device. The novel compound can effectively improve the efficiency of the device and reduce the voltage of the device, and can provide better device performance. An electroluminescent device comprising the compound and a compound composition comprising the compound are also disclosed.

Description

Technical Field

[0001] This invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound having the structure of Formula 1, and an organic electroluminescent device comprising the compound and a compound composition. 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 layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. 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 light-emitting 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 fabrication on 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] WO2021230714A discloses an organic optical compound having the following structure. As can be seen from the disclosed general formula structure, the triazine structural unit in its compound structure is connected to the 1 position of dibenzofuran via L1, but compounds in which the triazine structural unit is connected to the 2, 3, and 4 positions of dibenzofuran via L1 are not disclosed or taught.

[0009] KR1020200072211A discloses an organic optical compound having the following structure. As can be seen from the disclosed general formula structure, the triazine structural unit in its compound structure must be directly connected to dibenzofuran and similar structures through a single bond, but it does not disclose or teach compounds formed by connecting the triazine group to dibenzofuran and similar structures through a linking group.

[0010] KR1020190135707A discloses an organic electroluminescent device, the light-emitting layer of which comprises two main bodies, one of which has a general structure of [formula missing]. The application discloses in a specific structure This application did not study or focus on compounds with both naphthyl-phenyl and specifically substituted dibenzofuran and similar structures on the triazine structural unit.

[0011] However, many of the main materials reported so far still have room for improvement. To meet the industry’s ever-increasing demands, especially for higher device efficiency and lower drive voltage, new materials still need further research and development. Summary of the Invention

[0012] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the above-mentioned problems. These compounds can be used as host materials in organic electroluminescent devices, and these novel compounds can provide better device performance.

[0013] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0014]

[0015] Where Z is selected from O, S, or Se;

[0016] X1 to X8 are selected from C, CR each time they appear, either identically or differently. x Or N, one of X1 to X3 is selected from C and connected to L, and one of X1 to X8 is selected from C and connected to Ar1;

[0017] L is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms;

[0018] Y is selected from C, CR each time it appears, either identically or differently. y Or N;

[0019] Ar1 and Ar2, each time appearing, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0020] R x 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 1-20 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 aryl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, 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.

[0021] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of Formula 1, the specific structure of which is shown in the foregoing embodiment.

[0022] According to another embodiment of the present invention, a compound composition comprising the compound having the structure of Formula 1, wherein the specific structure of the compound is as shown in the foregoing embodiments is disclosed.

[0023] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an electroluminescent device, the specific structure of which is shown in the foregoing embodiment.

[0024] The novel compounds with the structure of Formula 1 disclosed in this invention can be used as host materials in electroluminescent devices. These novel compounds can provide higher efficiency and lower voltage, and provide better device performance. Attached Figure Description

[0025] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0026] 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

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] 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 1 The 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.

[0032] 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.

[0033] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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).

[0038] 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.

[0039] 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).

[0040] Definition of the term "substituent group"

[0041] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. 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 group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0059] 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.

[0060] 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.

[0061] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, 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.

[0062] 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.

[0063] 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:

[0064]

[0065] 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:

[0066]

[0067] 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:

[0068]

[0069] 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:

[0070]

[0071] According to one embodiment of the present invention, a compound having Formula 1 is disclosed:

[0072]

[0073] Where Z is selected from O, S, or Se;

[0074] X1 to X8 are selected from C, CR each time they appear, either identically or differently. x Or N, one of X1 to X3 is selected from C and connected to L, and one of X1 to X8 is selected from C and connected to Ar1;

[0075] L is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms;

[0076] Y is selected from C, CR each time it appears, either identically or differently. y Or N;

[0077] Ar1 and Ar2, each time appearing, are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0078] R x R yEach 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 aryl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, 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.

[0079] According to one embodiment of the present invention, Z is selected from O or S.

[0080] According to one embodiment of the present invention, Z is selected from O.

[0081] According to one embodiment of the invention, X1 to X8 are selected from C or CR each time they appear, either identically or differently. x And / or Y is selected from C or CR each time it appears, either the same or different. y , where R x 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 aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0082] According to one embodiment of the present invention, R x R y Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0083] According to one embodiment of the present invention, Ar1 and Ar2 are selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms each time they appear.

[0084] According to one embodiment of the invention, Ar1 and Ar2 are selected from the group consisting of phenyl, naphthyl, biphenyl, phenanthrene, terphenyl, triphenylene, and combinations thereof, each time they appear.

[0085] According to one embodiment of the invention, L is selected from the group consisting of phenylene, naphthylene, biphenylene, phenanthrene, and combinations thereof each time it appears.

[0086] According to one embodiment of the present invention, one of X5 to X8 is selected from C and is connected to Ar1.

[0087] According to one embodiment of the present invention, X8 is selected from C and is connected to Ar1.

[0088] According to one embodiment of the present invention, X2 is selected from C and connected to L.

[0089] According to one embodiment of the present invention, at least one of X1 to X8 is selected from N, and / or at least one of Y is N.

[0090] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds A-1 to A-150, and the specific structures of compounds A-1 to A-150 are given in claim 9.

[0091] According to one embodiment of the present invention, the hydrogen in the structure of compounds A-1 to A-150 is partially or completely replaced by deuterium.

[0092] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0093] anode,

[0094] cathode,

[0095] And an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of Formula 1, the specific structure of which is shown in any of the foregoing embodiments.

[0096] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is the light-emitting layer, and the compound is the host material.

[0097] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer contains at least one phosphorescent material.

[0098] According to one embodiment of the present invention, the phosphorescent material is a metal complex, and the metal complex has M(L) a )m (L b ) n (L c ) q The general formula;

[0099] M is selected from metals with a relative atomic mass greater than 40;

[0100] L a L b L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b L can be optionally linked to form a multidentate ligand;

[0101] L a L b L c They can be the same or different; 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 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;

[0102] L a It has the structure shown in Equation 2:

[0103]

[0104] in,

[0105] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0106] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0107] Rings D and E via U a and U b Condensation;

[0108] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0109] R d R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0110] V1-V4 are selected from CR each time they appear, either identically or differently. v Or N;

[0111] R dR e R v Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 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. alkyl, 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;

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

[0113] L b L c Each occurrence may be selected from any of the following structures, either identically or differently:

[0114]

[0115] in,

[0116] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0117] 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 ;

[0118] 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 ;

[0119] Ra 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 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. alkyl, 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;

[0120] The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0121] In this paper, adjacent substituents R d R e R v The ability to optionally connect to form a ring is intended to indicate the presence of a substituent R. d Substituent R e Substituent R v When, adjacent substituent groups, such as adjacent substituent R d Substituents R between and adjacent e Substituents R between and adjacent v Substituents R between and adjacent d With R e Substituents R between and adjacent d With R vBetween and adjacent substituents R e With R v Between these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... d Substituent R e Substituent R v At the same time, these substituent groups may not be connected to form a ring.

[0122] In this paper, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 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.

[0123] According to one embodiment of the present invention, in formula 2, R d R e R v At least one or two sets of adjacent substituents are linked to form a ring. For example, two substituents R d The connection forms a ring, or two substituents Re The connection forms a ring, or two substituents R v Linkage to form a ring, or substituent R d With substituent R e The links between them form a ring, or the substituent R d With substituent R v The links between them form a ring, or the substituent R e With substituent R v The two substituents R are connected to form a ring or a ring. d The two substituents R connect to form a ring. e The connection forms a ring, or two substituents R d The two substituents R connect to form a ring. v The connection forms a ring, or two substituents R e The two substituents R connect to form a ring. v Linkage forms a ring, substituent R e With substituent R v The two substituents R are linked to form a ring. v Linkage to form a ring, or substituent R d With substituent R v The two substituents R are linked to form a ring. v The connection forms a loop; R d R e R v A similar situation occurs when more adjacent substituents are linked to form a ring.

[0124] According to one embodiment of the present invention, in the device, the phosphorescent luminescent material is a metal complex, and the metal complex has M(L) a ) m (L b ) n The general formula;

[0125] M is selected from metals with a relative atomic mass greater than 40;

[0126] L a L b The first and second ligands, respectively, coordinate with M; L a L b They can be selectively linked to form multidentate ligands;

[0127] m is 1, 2, or 3; n is 0, 1, or 2; the sum of m and n equals the oxidation state of 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;

[0128] L aIt has the structure shown in Equation 2:

[0129]

[0130] in,

[0131] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0132] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0133] Rings D and E via U a and U b Condensation;

[0134] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0135] R d R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0136] V1-V4 are selected from CR each time they appear, either identically or differently. v Or N;

[0137] R d R e R v Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 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. alkyl, 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;

[0138] Adjacent substituent R d R e R vThey can be arbitrarily connected to form a loop;

[0139] The ligand L b It has the following structure:

[0140]

[0141] R1 to R7 are each independently selected from the group consisting of: 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, and substituted or unsubstituted groups having 2-20 carbon atoms. The group includes alkenyl groups, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0142] According to one embodiment of the present invention, in the device, wherein the ligand L b It has the following structure:

[0143]

[0144] Wherein, at least one of R1-R3 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 heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 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 heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0145] According to one embodiment of the present invention, in the device, wherein the ligand L b It has the following structure:

[0146]

[0147] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, 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 heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, 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 heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

[0148] According to one embodiment of the present invention, in the device, wherein the ligand L b It has the following structure:

[0149]

[0150] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.

[0151] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0152] According to one embodiment of the present invention, the phosphorescent material is an Ir complex and has Ir(L) a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a (L) b )2、Ir(L a )2(L c ) or Ir(L a (L) c Any of the structures shown in )2.

[0153] According to one embodiment of the present invention, wherein L a It has the structure shown in Formula 2 and contains at least one structural unit selected from the group consisting of a 6-membered 6-membered aromatic ring, a 6-membered 6-membered heteroaromatic ring, a 6-membered 5-membered aromatic ring and a 6-membered 5-membered heteroaromatic ring.

[0154] According to one embodiment of the present invention, wherein L a It has the structure shown in Formula 2 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0155] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. a The L a Each time it appears, choose either the same or different one from any of the following groups of structures:

[0156]

[0157]

[0158] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. b The L b Each time it appears, choose either the same or different one from any of the following groups of structures:

[0159]

[0160]

[0161] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] According to another embodiment of the present invention, a compound composition comprising a compound represented by Formula 1, wherein the specific structure of the compound is as shown in any of the foregoing embodiments is disclosed.

[0168] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an electroluminescent device, the specific structure of which is shown in any of the foregoing embodiments.

[0169] Combination with other materials

[0170] 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.

[0171] 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.

[0172] 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.

[0173] Material synthesis examples:

[0174] 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:

[0175] Synthesis Example 1: Synthesis of Compound A-1

[0176]

[0177] Under nitrogen protection, intermediate 1 (2.3 g, 6.2 mmol), intermediate 2 (2.9 g, 6.2 mmol), tris(dibenzylacetone)dipalladium (0.28 g, 0.31 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-phos, 0.25 g, 0.62 mmol), potassium carbonate (1.7 g, 12.4 mmol), and solvent (toluene / ethanol / water = 280 / 70 / 70 mL) were added to a three-necked flask and reacted overnight at 100 °C. After the reaction was complete, the mixture was cooled to room temperature and filtered to obtain a solid. The crude product was recrystallized from toluene to give a white solid compound A-1 (2.8 g, yield: 65%). The product was identified as the target product with a molecular weight of 677.2.

[0178] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0179] Device Example 1

[0180] First, the glass substrate, which has an 80 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate was achieved sequentially on the ITO anode via thermal vacuum. Compounds HT and HI were co-deposited as a hole injection layer (HIL) with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the compound A-1 of the present invention as the first main body, compound A as the second main body, and compound RD as the dopant are co-deposited as an emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited as an electron transport layer (ETL) with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0181] Device Example 2

[0182] The implementation of Device Example 2 is the same as that of Device Example 1, except that compound B is used instead of compound A in the light-emitting layer (EML).

[0183] Device Comparison Example 1

[0184] The implementation of Comparative Example 1 is the same as that of Example 1, except that compound C is used instead of compound A-1 of the present invention as the main component in the light-emitting layer (EML).

[0185] Device Comparison Example 2

[0186] The implementation of Comparative Example 2 is the same as that of Example 1, except that compound D is used instead of compound A-1 of the present invention as the main component in the light-emitting layer (EML).

[0187] Device Comparison Example 3

[0188] The implementation of Comparative Example 3 is the same as that of Example 1, except that compound E is used instead of compound A-1 of the present invention as the main component in the light-emitting layer (EML).

[0189] Device Comparison Example 4

[0190] The implementation of Comparative Example 4 is the same as that of Example 2, except that compound C is used instead of compound A-1 of the present invention as the main body in the light-emitting layer (EML).

[0191] 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.

[0192] Table 1. Partial device structures of the device embodiments and comparative examples.

[0193]

[0194]

[0195] The material structure used in the device is shown below:

[0196]

[0197]

[0198] Table 2 lists the results at a constant current of 15 mA / cm². 2 Under the conditions, the maximum emission wavelength (λ) of the device embodiment and the device comparative example was measured. max ), power efficiency (PE) and voltage.

[0199] Table 2 Device Data

[0200] Device ID max (nm) ​ PE [Im / W] Voltage [V] Example 1 619 21.36 3.69 Example 2 619 19.17 4.16 Comparative Example 1 619 20.65 3.92 Comparative Example 2 618 20.38 3.95 Comparative Example 3 618 20.84 3.87 Comparative Example 4 619 18.39 4.30

[0201] discuss:

[0202] As can be seen from the data in Table 2, the maximum emission wavelength of Example 1 is basically consistent with that of Comparative Examples 1, 2, and 3. Regarding power efficiency, Comparative Examples 1, 2, and 3 have already achieved very high levels of power efficiency, at 20.65 lm / W, 20.38 lm / W, and 20.84 lm / W, respectively. However, it is noteworthy that the compound of the present invention further improves the power efficiency of Example 1, with a maximum increase of 4.8%. Regarding operating voltage, although the comparative compounds can provide a low operating voltage of approximately 3.9V, the compound of the present invention can further reduce the voltage of Example 1, with a maximum reduction of 5.8%.

[0203] Furthermore, a comparison of the data from Example 2 and Comparative Example 4 further demonstrates that, when used together with another second host compound B as a host material, the compounds of the present invention also exhibit higher power efficiency and lower operating voltage compared to compound C, indicating the broad applicability of the compounds of the present invention. In summary, the results show that the compounds of the present invention can improve device efficiency and reduce device voltage, demonstrating the unique advantages of the compounds of the present invention.

[0204] 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. Compounds having Formula 1: ， in, Z is selected from O, S, or Se; X1 through X8 are selected from C or CR each time they appear, either identically or differently. x X2 is selected from C and connected to L, and one of X1 to X8 is selected from C and connected to Ar1; L is selected from substituted or unsubstituted aryl groups having 6 carbon atoms; Y is selected from C or CR each time it appears, either identically or differently. y ; Ar1, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-12 carbon atoms, either identically or differently; Ar2, each time it appears, is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, either identically or differently. R x 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 1-6 carbon atoms; The substituted aryl group having 6-12 carbon atoms and the substituted alkyl group having 1-6 carbon atoms refer to the aryl group or alkyl group being substituted by one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl group having 1-6 carbon atoms, and combinations thereof.

2. The compound of claim 1, wherein, Z is selected from O or S.

3. The compound of claim 2, wherein, Z is selected from O.

4. The compound of claim 1, wherein X1 to X8, each time appearing, are selected from C or C, either identically or differently. x And / or Y is selected from C or CR each time it appears, either the same or different. y ,in, R x R y Each time it appears, it is selected from the following groups, either the same or different: hydrogen, deuterium, halogen.

5. The compound of claim 4, wherein R x R y Each time it appears, it is selected from the following groups, either the same or different: hydrogen, deuterium.

6. The compound of claim 1, wherein, Ar1 and Ar2, each time appearing, are selected from substituted or unsubstituted aryl groups having 6-12 carbon atoms, either identically or differently.

7. The compound of claim 6, wherein, Ar1 and Ar2 are selected from the following groups, either identically or differently, each time they appear: phenyl, naphthyl, biphenyl.

8. The compound of claim 1, wherein one of X5 to X8 is selected from C and is connected to the Ar1.

9. The compound of claim 8, wherein X8 is selected from C and is connected to the Ar1.

10. The compound of claim 1, wherein the compound is selected from the group consisting of: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； Optionally, the hydrogen in the structures of compounds A-1 to A-36, A-48 to A-52, A-60 to A-70, A-86 to A-90, A-101 to A-104, A-111 to A-116, A-131 to A-133, A-136 to A-141 may be partially or completely replaced by deuterium.

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

12. The electroluminescent device of claim 11, wherein the organic layer is a light-emitting layer and the compound is a host material.

13. The electroluminescent device of claim 12, wherein the organic layer is a light-emitting layer, and the light-emitting layer comprises at least one phosphorescent material.

14. A compound composition comprising any one of the compounds of claims 1 to 10.

15. An electronic device comprising the electroluminescent device according to any one of claims 11 to 13.

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