Organic electroluminescent material and device thereof

Abstract

Disclosed are organic electroluminescent materials and devices thereof. The organic electroluminescent material is a compound having a structure of Formula 1, in particular, Formula 1 has a specific boron-containing polycyclic fused ring skeleton. These novel compounds can be used as light-emitting materials in organic electroluminescent devices, achieving desired green light emission, having excellent performance, and having potential application prospects as excellent light-emitting materials. Also disclosed are an organic electroluminescent device comprising the compound and a composition comprising the compound.

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 organic electroluminescent devices and compound compositions 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 electrode 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] KR1020210043468A discloses a compound having the following structure. Where A1 and A2 are carbon rings or heterocycles, and Y is selected from single bonds, CR... j R k SiR l R m , O, S or NR n It was also made public. The specific structures are not disclosed or taught, nor are compounds with specific substituents introduced on a polycyclic skeleton or specific rings introduced on the skeleton disclosed or taught, nor are the unique advantages that compounds with such specific structures can have.

[0009] Currently, materials with boron-containing multi-element fused rings typically exhibit a bluer luminescence, which limits their application in wide color gamut displays. However, green light is an important type of luminescent material, and developing green luminescent materials with superior performance based on this framework remains of great significance and importance. Summary of the Invention

[0010] 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 are capable of green light emission. These novel compounds possess excellent properties and have the potential to become excellent green luminescent materials.

[0011] According to one embodiment of the present invention, a compound is disclosed having a structure represented by Formula 1:

[0012]

[0013] Wherein, X is selected from O, S, Se, NR each time it appears, either the same or different. x or CR x And at least one X is selected from O, S, Se or NR. x ;

[0014] Cy1, Cy2 and Cy3 are each independently selected from unsaturated carbon rings having 5 to 30 carbon atoms or unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof;

[0015] Each time Z appears, it is selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR, or GeR, either the same or different.

[0016] R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0017] R, R xR1, R2, and R3, each time appearing, are 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 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, -BR'R', and combinations thereof;

[0018] Furthermore, when Cy1 is selected from a benzene ring, at least one R1 is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

[0019] The R', each time appearing, is 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 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;

[0020] Adjacent substituents R', R x R1, R2, and R3 can be arbitrarily connected to form a loop.

[0021] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising: 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 a compound having the structure of Formula 1, the specific structure of which is shown in the foregoing embodiments is also disclosed.

[0023] The present invention discloses compounds having the structure of Formula 1, which are capable of emitting green light. These compounds possess excellent properties and have the potential to become excellent green luminescent materials. Attached Figure Description

[0024] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0025] 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

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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).

[0037] 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.

[0038] 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).

[0039] Definition of the term "substituent group"

[0040] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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:

[0063]

[0064] 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:

[0065]

[0066] 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:

[0067]

[0068] 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:

[0069]

[0070] According to one embodiment of the present invention, a compound is disclosed having a structure represented by Formula 1:

[0071]

[0072] Wherein, X is selected from O, S, Se, NR each time it appears, either the same or different. x or CR x And at least one X is selected from O, S, Se or NR. x ;

[0073] Cy1, Cy2 and Cy3 are each independently selected from unsaturated carbon rings having 5 to 30 carbon atoms or unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof;

[0074] Each time Z appears, it is selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR, or GeR, either the same or different.

[0075] R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0076] R, R x R1, R2, and R3, each time appearing, are 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 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, -BR'R', and combinations thereof;

[0077] Furthermore, when Cy1 is selected from a benzene ring, at least one R1 is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

[0078] The R', each time appearing, is 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 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;

[0079] Adjacent substituents R', R x R1, R2, and R3 can be arbitrarily connected to form a loop.

[0080] In this paper, in Equation 1, This indicates that the five-membered ring including X is an aromatic five-membered ring.

[0081] According to one embodiment of the present invention, X is selected from O, S, and NR each time it appears, either identically or differently. x or CR x And at least one X is selected from O, S or NR. x .

[0082] According to one embodiment of the present invention, X is selected from NR each time it occurs, either identically or differently. x or CR x And at least one X is selected from NR x .

[0083] According to one embodiment of the present invention, the ring Cy1, ring Cy2, and ring Cy3 are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms, heteroaromatic rings having 3-18 carbon atoms, or combinations thereof.

[0084] According to one embodiment of the present invention, wherein the ring Cy1, ring Cy2 and ring Cy3 are each independently selected from benzene ring, pyridine ring, naphthyl ring, phenanthrene ring, anthracene ring, indene ring, fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, dibenzothiophene ring, dibenzoselenene ring, cyclopentadiene ring, furan ring, thiophene ring, thiophene ring, pyrrole ring, or combinations thereof.

[0085] According to one embodiment of the present invention, the ring Cy1 is selected from an aromatic ring having 6-18 carbon atoms or a heteroaromatic ring having 3-18 carbon atoms.

[0086] According to one embodiment of the present invention, the ring Cy1 is selected from benzene ring, pyridine ring, naphthyl ring, phenanthrene ring, anthracene ring, fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, benzothiophene ring, dibenzoselenene ring, furan ring, thiophene ring, thiophene ring, pyrrole ring, or combinations thereof.

[0087] According to one embodiment of the present invention, the compound has a structure represented by any one of formulas 2-1 to 2-21:

[0088]

[0089]

[0090] Among them, Z is selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR or GeR each time it appears;

[0091] X and X1 are selected from O, S, Se, or NR each time they appear, either identically or differently. x ;

[0092] L1 is selected from O, S, Se, BR”, NR”, PR”, P=OR”, P=SR”, AsR”, As=OR”, As=SR”, CR”R”, SiR”R” or GeR”R” each time it appears; when two R” exist at the same time, the two R” are the same or different;

[0093] Each time A1 appears, it is selected from CR1 or N, and in Formulas 2-1 to 2-7, at least one A1 is selected from CR1, and the R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; each time A2 appears, it is selected from CR2 or N, each time A3 appears, it is selected from CR3 or N, and each time A4 appears, it is selected from CR4 or N.

[0094] R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution;

[0095] R, R” R x R1, R2, R3, and R4, each time appearing, are 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 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, 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, -BR'R', and combinations thereof;

[0096] The R', each time appearing, is 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 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;

[0097] Adjacent substituents R', R'', R x R1, R2, R3, and R4 can be optionally connected to form a loop.

[0098] According to one embodiment of the present invention, the compound has a structure represented by any one of formula 2-1, formula 2-11, formula 2-12, formula 2-13 and formula 2-14.

[0099] According to one embodiment of the present invention, the compound has a structure represented by any one of formulas 2-11, 2-12, 2-13 and 2-14.

[0100] According to one embodiment of the present invention, X is selected from O, S, or NR. x .

[0101] According to one embodiment of the present invention, X is selected from NR. x .

[0102] According to one embodiment of the present invention, X1 is selected from O, S or NR. x .

[0103] According to one embodiment of the present invention, X1 is selected from NR. x .

[0104] According to one embodiment of the present invention, L1 is selected from O, S, Se, BR”, NR”, P=OR”, CR”R” or SiR”R”; the R” is selected from the group consisting of: 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0105] According to one embodiment of the present invention, L1 is selected from O, S, NR”, CR”R” or SiR”R”; the R” is selected from the group consisting of: 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, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0106] According to one embodiment of the present invention, Z is selected from B, N, P, P=O or P=S each time it appears.

[0107] According to one embodiment of the present invention, Z is selected from B, N or P.

[0108] According to one embodiment of the present invention, Z is selected from N.

[0109] According to one embodiment of the present invention, in formulas 2-1 to 2-21, at least one of A1-A4 is selected from N.

[0110] In this embodiment, since there are multiple A1s, at least one A1 can be selected from N; similarly, since there are multiple A2s, at least one A2 can be selected from N; since there are multiple A3s, at least one A3 can be selected from N; since there are multiple A4s, at least one A4 can be selected from N.

[0111] According to one embodiment of the present invention, in formulas 2-1 to 2-21, A1 is independently selected from CR1, A2 is independently selected from CR2, A3 is independently selected from CR3, and A4 is independently selected from CR4.

[0112] According to one embodiment of the invention, wherein R1, R2, R3 and R4, each time appearing, are 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 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 amino groups having 0-20 carbon atoms, cyano groups, isocyano groups, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.

[0113] According to one embodiment of the present invention, at least two or three of R1, R2, R3, and R4 are selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, pyridyl, naphthyl, phenanthryl, anthracene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene The following are compounds: pyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino, and combinations thereof; and in formulas 2-1 to 2-7, at least one R1 is selected from the group consisting of: phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, pyridyl, naphthyl, phenanthryl, anthraceneyl, indole, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzothiophenyl, dibenzoselenophenyl, diphenylamino, dibenzofuranylphenylamino.

[0114] According to one embodiment of the invention, at least one of R1, R2, R3, and R4, when appearing in each instance, is selected from the group consisting of: 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 alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted aryl groups having 6-30 carbon atoms. The substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, the substituted or unsubstituted alkylsilyl group having 3-20 carbon atoms, the substituted or unsubstituted alkylgermanyl group having 3-20 carbon atoms, the substituted or unsubstituted amino group having 0-20 carbon atoms, cyano group, isocyano group, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from the substituted or unsubstituted aryl group having 6-30 carbon atoms or the substituted or unsubstituted heteroaryl group having 3-30 carbon atoms.

[0115] According to one embodiment of the invention, at least one of R1, R2, R3 and R4, each time appearing, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-12 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, cyano groups, and combinations thereof; and in formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.

[0116] According to one embodiment of the invention, at least one of R1, R2, R3 and R4, each time appearing, is selected from the group consisting of: deuterium, fluorine, cyano, substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 cyclic carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl having 6-30 carbon atoms or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0117] According to one embodiment of the invention, at least one of R1, R2, R3, and R4, when appearing each time, is selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, pyridyl, naphthyl, phenanthryl, anthracene, indole, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl. Benzothiophene, dibenzothiophene, dibenzoselenophene, diphenylamino, dibenzofuranylphenylamino, and combinations thereof; and in formulas 2-1 to 2-7, at least one R1 is selected from the group consisting of: phenyl, biphenyl, terphenyl, tetraphenyl, triphenylene, tetraphenylene, pyridyl, naphthyl, phenanthryl, anthraceneyl, indene, fluorenyl, indolyl, carbazole, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, dibenzoselenophene, diphenylamino, dibenzofuranylphenylamino.

[0118] 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, 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 alkenyl 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 aralkyl groups having 7-30 carbon atoms, and combinations thereof.

[0119] 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 the following: 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.

[0120] 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 the following: 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.

[0121] According to one embodiment of the present invention, the maximum emission wavelength range of the compound in the photoluminescence spectrum (PL) is 500 nm-580 nm.

[0122] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds BN1 to BN560, wherein the specific structures of compounds BN1 to BN560 are described in claim 9.

[0123] According to one embodiment of the present invention, the hydrogen in compounds BN1 to BN560 can be partially or completely replaced by deuterium.

[0124] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula 1, the specific structure of which is shown in any of the foregoing embodiments.

[0125] According to one embodiment of the present invention, the organic layer is a light-emitting layer, and the compound is a light-emitting material.

[0126] According to one embodiment of the present invention, the organic electroluminescent device emits green light.

[0127] According to one embodiment of the present invention, the light-emitting layer comprises at least a first host material.

[0128] According to one embodiment of the present invention, the light-emitting layer comprises at least a first host material and a second host material.

[0129] According to one embodiment of the present invention, the first host material has a structure represented by formula PH-1, formula PH-2, or formula PH-3:

[0130]

[0131] Among them, Y1 is selected from CR each time it appears, either the same or different. y Or N;

[0132] Y2 is selected from C, CR each time it appears, either identically or differently. y Or N;

[0133] L, each time it appears, is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0134] Ar 21 Ar 22 Ar 31 Ar 32 Ar 33 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, either in the same or different manner.

[0135] 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 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;

[0136] Adjacent substituent R y They can be arbitrarily connected to form a ring.

[0137] In this paper, adjacent substituents R y They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, adjacent substituent R. y These substituents can connect to form a ring. Obviously, these substituents can also remain unconnected to form a ring.

[0138] According to one embodiment of the present invention, the first main material is selected from the group consisting of compounds 1-1-1 to 1-1-104, compounds 1-2-1 to 1-2-100, and compounds 1-3-1 to 1-3-110: the specific structures of wherein compounds 1-1-1 to 1-1-104, compounds 1-2-1 to 1-2-100, and compounds 1-3-1 to 1-3-110 are described in claim 12.

[0139] According to one embodiment of the present invention, the hydrogen in compounds 1-1-1 to 1-1-104, 1-2-1 to 1-2-100 and 1-3-1 to 1-3-110 can be partially or completely replaced by deuterium.

[0140] According to one embodiment of the present invention, the second host material has a structure represented by the formula NH-1:

[0141]

[0142] Among them, L 11 To L 13 Each time it appears, it 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 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0143] Ar 11 To Ar 13 Each time it appears, it is 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, either identically or differently.

[0144] According to one embodiment of the present invention, the second host material is selected from the group consisting of compounds B-1 to B-243, wherein the specific structures of compounds B-1 to B-243 are described in claim 12.

[0145] According to one embodiment of the present invention, the hydrogen in compounds B-1 to B-243 can be partially or completely replaced by deuterium.

[0146] According to one embodiment of the present invention, the light-emitting layer comprises at least one metal complex.

[0147] According to one embodiment of the present invention, the metal complex is a phosphorus photosensitizer.

[0148] According to one embodiment of the present invention, the metal complex has M(L) a ) m (L b ) n (L c ) q The general formula;

[0149] M is selected from metals with a relative atomic mass greater than 40;

[0150] L a L b and L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b and L c They can be selectively linked to form multidentate ligands;

[0151] L a L b and Lc 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 Same or different; when n is 2, the two L b Same or different; when q is 2, the two L c Same or different;

[0152] L a Each occurrence may be selected from the structure shown in Equation 2, either identically or differently:

[0153]

[0154] in,

[0155] Ring A 11 And Ring A 12 Selected from aromatic rings having 6-30 ring atoms, heteroaromatic rings having 5-30 ring atoms, or combinations thereof;

[0156] T1 and T2 are selected from C or N each time they appear, either in the same or different ways.

[0157] K 11 and K 12 Each occurrence is either identical or different and selected from single bonds, O, S, or NR. k ;

[0158] L 31 Each time it appears, select the group consisting of the following, either identically or differently: single key, BR L11 CR L11 R L11 NR L11 O, SiR L11 R L11 PR L11 S, GeR L11 R L11 Se, substituted or unsubstituted vinylene, ethynylene, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, and combinations thereof; when two R are present simultaneously L11 At that time, two R L11 Same or different;

[0159] a1 is selected from 0 or 1;

[0160] R 11 and R 12 Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0161] R L11 R 11 R12 and R k 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;

[0162] Adjacent substituent R L11 R 11 and R 12 They can be arbitrarily connected to form a loop;

[0163] L b and L c Each occurrence may be selected from any of the following structures, either identically or differently:

[0164]

[0165]

[0166] in,

[0167] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0168] 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 ;

[0169] X c and X dEach time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0170] 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;

[0171] 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.

[0172] In this paper, adjacent substituents R L11 R 11 and R 12 They can be optionally linked into rings, intended to indicate the presence of substituent R. L11 Substituent R 11 Substituent R 12 When, adjacent substituent groups, such as adjacent substituent R L11 Substituents R between and adjacent 11 Substituents R between and adjacent 12 Substituents R between and adjacent L11 With R11 Substituents R between and adjacent L11 With R 12 Between and adjacent substituents R 11 With R 12 Between these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... L11 Substituent R 11 Substituent R 12 At the same time, these substituent groups may not be connected to form a ring.

[0173] 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.

[0174] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds RD1 to RD214 and compounds GD1 to GD185, wherein the specific structures of compounds RD1 to RD214 and compounds GD1 to GD185 are described in claim 13.

[0175] According to one embodiment of the present invention, the hydrogen in the structures of compounds RD1 to RD214 and compounds GD1 to GD185 can be partially or completely replaced by deuterium.

[0176] According to another embodiment of the present invention, a compound composition is also disclosed, comprising the compound having the structure of Formula 1, the specific structure of which is shown in any of the foregoing embodiments.

[0177] Combination with other materials

[0178] 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.

[0179] 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 light-emitting dopants disclosed herein can be used in combination with a variety of host layers, transport layers, barrier layers, injection 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.

[0180] 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.

[0181] Material synthesis examples:

[0182] The preparation method of the compounds of this invention is not limited. Those skilled in the art can select appropriate raw materials and process routes according to the synthesis objectives. Those skilled in the art can also prepare the compounds according to the following schematic synthesis route:

[0183] Synthesis route:

[0184] Step 1:

[0185]

[0186] In step one, intermediates 1 and 2 are coupled using the Suzuki reaction to obtain intermediate 3, where ring A represents a five-membered heteroaromatic ring, Hal1 is Cl, Br, etc., Hal2 is Cl, Br, I, OTf, etc., and Hal3 is Br, I, etc. The reaction conditions for the Suzuki reaction are well known to those skilled in the art; for example, common palladium metal reagents such as palladium acetate and Pd2(dba)3 are commonly used. Ligands are typically phosphine ligands such as PtBu3, X-phos, Xantphos, S-phos, DPPF, BINAP, Ruphos, etc. Bases are typically inorganic bases such as potassium phosphate, potassium carbonate, sodium carbonate, and cesium carbonate. Solvents are typically mixtures of common organic solvents such as toluene, dioxane, or xylene with water. Generally, the reaction concentration is 0.01-0.5 [M], and the reaction temperature is between 80°C and 180°C.

[0187] Step Two:

[0188]

[0189] In step two, intermediates 3 and 4 undergo carbon-nitrogen coupling reactions such as the Ullmann reaction and the Buchwald reaction to obtain intermediate 5, where Hal1 is Cl, Br, etc., and Hal3 is Br, I, etc. The reaction conditions for the Buchwald reaction are well known to those skilled in the art. For example, in the above formula, common palladium reagents [Pd] are typically used, such as palladium acetate, Pd2(dba)3, etc.; ligands are typically organophosphine ligands, such as P(tBu)3, X-phos, Xantphos, S-phos, DPPF, BINAP, Ruphos, etc.; bases are typically organic or inorganic bases, such as sodium tert-butoxide, lithium tert-butoxide, potassium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate, etc. Solvents are typically common organic solvents such as toluene, tert-butylbenzene, or xylene; generally, the reaction concentration is 0.01-0.5 [M], and the reaction temperature is between 90°C and 180°C.

[0190] Step 3:

[0191]

[0192] In step three, intermediate 5 is metallized at a specific aryl position using a lithium metal reagent, followed by lithium-boron metal exchange with a boron reagent, and then a tandem borane-friedel-Crafts reaction with a Bronsted base to obtain the target compound. A Lewis acid may also be added to promote the reaction.

[0193] The reaction conditions for metallization and Friedel-Crafts reactions are well known to those skilled in the art. For example, the metallization reaction can directly utilize lithium metal reagents to perform a lithium-halogen exchange reaction at the Hal3 position to achieve lithiation. Common lithium metal reagents include alkyl lithiums such as methyllithium, n-butyllithium, sec-butyllithium, and tert-butyllithium, or lithium diisopropylaminolithium and lithium tetramethylpiperidide, with the amount of lithium metal reagent typically being 2-5 equivalents. Boron reagents typically use boron trichloride or boron tribromide, with the amount of boron reagent typically being 3-6 equivalents. Brønsted bases typically use organic bases such as N,N-diisopropylethylamine, triethylamine, and 2,2,6,6-tetramethylpiperidin, with the amount typically being 5-10 equivalents. Under normal circumstances, the reaction concentration is 0.01-0.5 [M], and the reaction temperature is between -78°C and 180°C.

[0194] To promote the reaction, Lewis acids, such as AlCl3, BF3·OEt2, BCl3, BBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, etc., can be added.

[0195] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can improve it to obtain other compound structures selected in this invention.

[0196] The compounds of this invention have a specific polycyclic structure design that allows for different degrees of regulation of the emission color, enabling the desired green light emission. To further verify the emission effect, the maximum emission wavelength and energy level of some compounds of this invention were calculated using DFT calculations.

[0197] The DFT calculation method used in this invention:

[0198] Using the B3LYP hybrid functional and the 6-311G** effective nuclear potential basis set within the Gaussian software package, and simulating the THF solvent environment with the SMD solvation model, DFT calculations were performed on the compounds of this invention and comparative compounds. The HOMO values, LUMO values, and singlet emission wavelengths λ (nm) of the compounds were obtained, and the data are recorded and presented in Table 1:

[0199] Table 1 DFT Calculation Results

[0200]

[0201]

[0202] The structures of the relevant compounds are as follows:

[0203]

[0204] discuss:

[0205] As shown in Table 1, the compounds of this invention, due to their specific Formula 1 structure, can achieve the desired green light emission. Compared with compound A, the main difference between compounds BN352, BN314, BN347, BN312, BN388, and BN318 is that the Cy1 ring is a specific heteroaryl ring, and their emission wavelengths are all significantly red-shifted by 20–70 nm compared to the comparative compound A. This red-shift effect is unexpected. Compared with compound B, compounds BN349, BN350, BN527, and BN318 also exhibit green light emission. N528 also introduces a heteroaryrheic ring at a specific position. Calculation results show that, compared with compound B, the maximum emission wavelength of the compounds of the present invention is unexpectedly redshifted by 40-75 nm. In addition, the HOMO energy level values ​​of the compounds of the present invention are comparable to or shallower than those of the comparative compounds, indicating that the compounds of the present invention may have hole trapping capabilities comparable to or stronger than those of the comparative compounds. Strong hole trapping capabilities are beneficial for the metal complexes of the present invention to achieve excellent performance in devices, such as low voltage, high device efficiency, and long device lifetime.

[0206] In summary, the compounds of the present invention with the specific formula 1 structure have successfully achieved a significant redshift in emission wavelength. More importantly, the compounds of the present invention have the potential to become excellent green light materials, greatly enriching the fluorescent luminescent material system and the emission color range, demonstrating the excellent performance and broad potential application prospects of the compounds of the present invention with the specific formula 1 structure.

[0207] 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 a structure represented by Formula 1: in, X is selected from O, S, Se, N, NR each time it appears, either identically or differently. x or CR x And at least one X is selected from O, S, Se or NR. x ; Cy1, Cy2 and Cy3 are each independently selected from unsaturated carbon rings having 5 to 30 carbon atoms or unsaturated heterocycles having 3 to 30 carbon atoms, or combinations thereof; Each time Z appears, it is selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR, or GeR, either the same or different. R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution; R, R x R1, R2, and R3, each time appearing, are 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 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, -BR'R', and combinations thereof; Furthermore, when Cy1 is selected from a benzene ring, at least one R1 is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms; The R', each time appearing, is 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 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; Adjacent substituents R', R x R1, R2, and R3 can be arbitrarily connected to form a loop.

2. The compound of claim 1, wherein X is selected from O, S, NR each time it appears, either identically or differently. x or CR x And at least one X is selected from O, S or NR. x ; Preferably, X is selected from NR each time it appears, either identically or differently. x or CR x And at least one X is selected from NR x .

3. The compound of claim 1, wherein, The ring Cy1, ring Cy2 and ring Cy3 are each independently selected from five-membered unsaturated carbon rings, aromatic rings having 6-18 carbon atoms or heteroaromatic rings having 3-18 carbon atoms, or combinations thereof; Preferably, the rings Cy1, Cy2, and Cy3 are each independently selected from benzene rings, pyridine rings, naphthyl rings, phenanthrene rings, anthracene rings, indene rings, fluorene rings, indole rings, carbazole rings, benzofuran rings, dibenzofuran rings, benzothiophene rings, dibenzothiophene rings, dibenzothiophene rings, dibenzoselenene rings, cyclopentadiene rings, furan rings, thiophene rings, thiophene rings, pyrrole rings, or combinations thereof.

4. The compound of claim 1, wherein, The compound has a structure represented by any one of Formulas 2-1 to 2-21: Among them, Z is selected from B, N, P, P=O, P=S, As, As=O, As=S, SiR or GeR each time it appears; X and X1 are selected from O, S, Se, or NR each time they appear, either identically or differently. x ; L1 is selected from O, S, Se, BR”, NR”, PR”, P=OR”, P=SR”, AsR”, As=OR”, As=SR”, CR”R”, SiR”R” or GeR”R” each time it appears; when two R” exist at the same time, the two R” are the same or different; Each time A1 appears, it is selected from CR1 or N, and in Formulas 2-1 to 2-7, at least one A1 is selected from CR1, and the R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; each time A2 appears, it is selected from CR2 or N, each time A3 appears, it is selected from CR3 or N, and each time A4 appears, it is selected from CR4 or N. R1, R2, and R3 appearing in the same or different ways each time indicate monosubstitution, polysubstitution, or no substitution; R, R” R x R1, R2, R3, and R4, each time appearing, are 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 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, 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, -BR'R', and combinations thereof; The R', each time appearing, is 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 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; Adjacent substituents R', R'', R x R1, R2, R3, and R4 can be arbitrarily connected to form a loop; Preferably, the compound has a structure represented by any one of Formula 2-1, Formula 2-11, Formula 2-12, Formula 2-13 and Formula 2-14; More preferably, the compound has a structure represented by any one of Formula 2-11, Formula 2-12, Formula 2-13 and Formula 2-14.

5. The compound of claim 4, wherein, Z is selected from B, N, P, P=O, or P=S each time it appears; Preferably, Z is selected from B, N, or P; More preferably, Z is selected from N.

6. The compound of claim 4, wherein, In Equations 2-1 to 2-21, at least one of A1-A4 is selected from N.

7. The compound of claim 4, wherein, The R1, R2, R3, and R4, each time appearing, are 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 aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, cyano groups, isocyano groups, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; Preferably, at least one of R1, R2, R3, and R4, when appearing in the same or different manner, is selected from the group consisting of: 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 alkenyl 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 amino groups having 0-20 carbon atoms, cyano groups, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; More preferably, at least one of R1, R2, R3 and R4, each time appearing, is selected from the group consisting of: deuterium, fluorine, cyano, substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 cyclic carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof; and in Formulas 2-1 to 2-7, at least one R1 is selected from substituted or unsubstituted aryl having 6-30 carbon atoms or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

8. The compound of claim 4, wherein, 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, 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 alkenyl 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 aralkyl groups having 7-30 carbon atoms, and combinations thereof; Preferably, the R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl 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, and combinations thereof; More preferably, the R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: 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.

9. The compound of claim 1, wherein, The compounds are selected from the group consisting of compounds BN1 to BN560: Optionally, the hydrogen in compounds BN1 to BN551 can be partially or completely replaced by deuterium.

10. An organic electroluminescent device, comprising: anode, cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer comprises any one of 1-9 compounds.

11. The organic electroluminescent device as claimed in claim 10, wherein, The organic layer is a light-emitting layer, and the compound is a light-emitting material; Preferably, the organic electroluminescent device emits green light.

12. The organic electroluminescent device as claimed in claim 11, wherein, The light-emitting layer comprises at least a first host material or the light-emitting layer comprises at least a first host material and a second host material; Preferably, the first host material has a structure represented by formula PH-1, formula PH-2, or formula PH-3: Among them, Y1 is selected from CR each time it appears, either the same or different. y Or N; Y2 is selected from C, CR each time it appears, either identically or differently. y Or N; L, each time it appears, is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar 21 Ar 22 Ar 31 Ar 32 Ar 33 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, either in the same or different manner. 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 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; Adjacent substituent R y They can be arbitrarily connected to form a loop; The second main material has a structure represented by the formula NH-1: Among them, L 11 To L 13 Each time it appears, it 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 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. Ar 11 To Ar 13 Each time it appears, it is 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, either identically or differently. More preferably, the first host material is selected from the group consisting of compounds 1-1-1 to 1-1-104, compounds 1-2-1 to 1-2-100, and compounds 1-3-1 to 1-3-110. Optionally, the hydrogen in the structures of compounds 1-1-1 to 1-1-104, 1-2-1 to 1-2-100, and 1-3-1 to 1-3-110 can be partially or completely replaced by deuterium; The second host material is selected from the group consisting of compounds B-1 to B-243: Optionally, the hydrogen in the structure of compounds B-1 to B-243 may be partially or completely replaced by deuterium.

13. The organic electroluminescent device of claim 11, wherein the light-emitting layer comprises at least one metal complex; Preferably, the metal complex is a phosphorus photosensitizer; More preferably, the metal complex is selected from the group consisting of compounds RD1 to RD214 and compounds GD1 to GD185: Optionally, the hydrogen in the structures of compounds RD1 to RD214 and compounds GD1 to GD185 may be partially or completely replaced by deuterium.

14. A compound composition comprising the compound as described in any one of claims 1-9.

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